My best friend says that the reason I’m an investor and not just a writer is because I really like being right. She’s right, but I’d add that I especially enjoy being right about decisions that I made by following my intuition. These are the kind of gut feelings that you feel in your body before you can explain why with words.

I credit this variety of gut feeling for all the best decisions I’ve made in my life: my best investments, career moves, and marrying my husband. It’s no coincidence that all of these decisions were about people — I strongly believe that all of the most important choices are.

For these reasons, intuition has been of interest to me for a long time. A few notes I’ve collected:

1. Intuitive decisions at their best draw on the sum total wisdom of your lived experience, usually felt as a sensation in your gut or heart. This is distinct from a rational decision (slow, purely cognitive) and an emotional one (fast, reactive, often shows up as FOMO in investing). The main reason people avoid making intuitive decisions is because failures of intuition feel more crushing and personal.
   

2. It seems that you can’t credibly talk about intuition in investing until you’ve proven yours can make a lot of money. Yet that doesn’t mean intuitive decisions aren’t being made all around us — they’re often hiding in plain sight any time an investor passionately waxes poetic about how talented a founder is.
   

3. What’s interesting about intuition is that it’s inherently anti-memetic. Unlike taste, which you can see the direct products of in the world and therefore emulate, intuition is something only one person feels in their body and is thus non-transferable. It won’t earn you cool points to talk about in Silicon Valley, but it could very well be the reason you win.
   

4. Focusing on building your intuition is the closest thing I’ve found to a cheat code to high slope growth. You do this by making a lot of decisions and deeply internalizing a sense of what worked, what didn’t, and why. Creative practices are great starting places to get a hang of this process.
   

5. I believe that there’s a great deal of power in openly expressing your intuitions about a person and speaking from that place. As onlookers we metabolize others’ intuition as authenticity.

My career is a story of being drawn to studying people who were doing the thing they were meant to do. I wanted to know why it worked so well for them, and found through practice that I’m good at helping them become even better at it. Over time, I uncovered what that thing was for me: finding and understanding these quiet, quirky, mission-driven founders I call moths. In doing so, I’ve come to understand myself much better as one too.

I started taking psychology classes at my local community college in my freshman year of high school. I loved them, but found it frustrating how much focus was put on our dysfunction when my interest was with how people — especially outliers — can become great. So I went looking in the real world, studying people I respected up close across 20 jobs before I found investing as the container where I could act on what I see.

What I do today looks a lot like studying how people become great, with feedback loops attached. My goal is to find the most competent weirdos and build relationships with them. I generally meet them through the network of “mothy” people I’ve cultivated over the past five years. I want to have already built trust with them and shown how I can be helpful by the time a select few of these moths start to take off and metamorphose into exactly what their business needs to grow.

My aim is to provide what I’ve found founders find most useful at the idea stage: coaching, money (grants and/or investment dollars), and help on storytelling. The founders who make the most sense for my model are often building in spaces with a higher burden of proof to raise capital at the earliest stages (aka not enterprise AI). Because of this, they live or die by storytelling in the interstitial period between pre-seed and seed. I can help with that.

Two misconceptions can arise here. Either that I find people in the middle of nowhere and teach them how to storytell or that I back founders who need me. Neither are true. To get conviction on a founder, I need to see a path to them winning with or without me. If we decide to work together, my aim is to accelerate their inevitable growth.

I started Moth to create the kind of partner I wished I’d had when I was just out of college. As a moth, I’ve experienced firsthand that our mystery starts to melt away as moths achieve legible success, making us appear sparkly and obviously talented to newcomers. That doesn’t mean we feel like butterflies inside, though. At the core of being a moth is feeling misunderstood, an experience that only tends to intensify from spending time in the spotlight.

Which is why the most valuable thing I can offer isn’t money or coaching — it’s recognition and belief in this certain kind of person. My work is to discern which of the ambitions of these founders genuinely make sense for venture capital, and to resist comparing them to examples set forth by more obvious butterflies. I strive to be specific in my articulations of what makes my founders special and help them learn to trust themselves.

Tenacity is one of my favorite words, and feelings. There’s nothing like being presented with an opportunity to be brave and taking it. It pushes you out of your comfort zone inch by inch until one day you open your eyes and realize you’ve completely changed your position on what you believe you can do.

This past year has been a real test of my tenacity. I went from struggling to raise my second fund to running full force at what I always wanted to build with Moth, but thought I needed to wait several years to actualize.

The truth was that my first fundraise spoiled me. It was anchored by people I respected who had mostly made their own money, and I didn’t have to work that hard to convince them to back me. I assumed Fund II would work the same way — just do it again at a larger scale with some institutional LPs mixed in.

I quickly learned how wrong I was. Raising from capital owners (typically HNWs) versus capital allocators (institutions) is a completely different game, and I didn’t know how to run an institutional fundraise process. After two months of spinning my wheels, I paused, closed on what I’d raised, and deployed it. That gave me time to consider my options.

Once I started to see the signs that I could be leading rounds, I decided it was time to go big or go home. I rebuilt the fund model and through trial and error, taught myself how to sell to capital allocators. It’s been a learning curve, but after a few months of pitching the new strategy I saw it start to work in a big way.

There are a few things that I attribute this shift to. One, I started asking for help, even when I felt intense shame discussing what felt like my personal inadequacies and every fiber of my being wanted to run away. Two, I started taking more responsibility for the situation and made an effort to root out my victim mentality.

Lastly, I practiced my pitch a lot. Both with my target audience (LPs) and with my peers (GPs). Getting Moth and my story to a place where I could say it in my sleep allowed me to show up with more ease in conversation. Being more fully present lets me tap into my genuine excitement for what I’m doing, as well as feel more generative and open to the possibilities of where the conversation could go. Practicing with friends right before important pitches helps kickstart this attitude and show, not tell, where my edge comes from.

Fundamentally, I like the proximity investing gives me to incredible people. I like how much autonomy I have. I like how I can exert my taste on the world through the people I fund. I like learning more about humans every single day. But what I don’t like is fundraising, nor the majority of people who call themselves VCs.

Authenticity and tenacity are my most durable advantages — both in fundraising and in backing founders. I’ve been running Moth Fund long enough to have plenty of data points on the lived reality of doing this job. I intimately know the parts I don’t like but also, crucially, why I choose to stay.

Dear Moth,

I know I’m bad at telling my own story. I kinda just make it up anew every time I’m asked and while I like the way that helps what I say feel less like a pitch, I hate coming out of many of these conversations wishing I’d presented myself better. How do I get better at telling my story?

— Humble Mumble

Dear Humble Mumble,

Up until around 6 months ago, I was extremely resistant to doing the work to become a better teller of my own story. Despite spending a lot of time helping others develop this skill, I felt strongly that making my story easily digestible to others would diminish my authenticity in a way that felt self-serving and wrong.

I’ve mostly gotten over that now, mainly because I realized I basically just wasn’t taking myself seriously. On one hand, I’d gotten decently far in my career without ever learning to pitch myself, which gave me the mistaken sense I might never need to. On the other hand, I didn’t feel very proud of the things I had to talk about and gave way too much detail than anyone wanted because I was so afraid of being misunderstood.

Ironically, this meant that I ended up being misunderstood by people who weren’t like me most of the time. The more the misunderstandings compounded, the more I resisted fixing the problem and took it personally. Their confusion felt like a reflection of my character instead of the obvious storytelling failure that it was.

The turning point was when I finally asked a trusted mentor for help. I presented my story to him and watched as his face twisted in confusion. Here was someone who knew me well, believed in me, and yet was completely confused by the way I was describing myself. Finally it clicked — this was a narrative problem, not a me problem. He helped me discern which details were important and noted compelling through lines he saw in my story, giving me the seeds of confidence I needed to state them out loud to others too.

Now, does it feel comfortable revealing I was hand-picked by lots of important people? No, absolutely not. It feels unnatural and braggy. But not saying it out loud was leaving me stuck in the misunderstanding mud, unable to do anything for anyone. It helps to think about why I’m talking myself up — because by doing so, I’m able to help other exceptional people spend more time doing and less time talking about themselves.

I think most of the resistance people feel to getting better at telling their story is actually just immaturity. Growing up is realizing that we’re all special snowflakes (especially in Silicon Valley) and you can’t expect others to know why you’re special unless you tell them. If you feel rejected or like you did something wrong when your specialness isn’t immediately recognized, you should probably address that belief head-on.

I think if you’re a good person, you should talk more. I also think that you should only spend time refining your story once you’ve done enough things in the world to know who you are. At a bare minimum, I hope you stop self deprecating. That’s not humility, that’s critiquing yourself before others can in order to feel a sense of control.

— Moth

Dear Moth,

I founded a project I really care about a year or so ago and recently hit a bit of a juncture. I need money if I want to continue to work on it and hire people to help me begin the next stage, but I’m apprehensive about raising venture. I’ve seen too many of my founder friends become miserable after raising money — it seems to often take all the joy out of building for them. I like being a founder in the sense that I’m starting something from nothing and catalyzing change, but I don’t like the idea of being financially obligated to build a billion-dollar business. What if that’s not the right path for this project but I only realize that many years from now?

I want to work with my talented friends to make something excellent that helps others in some way. Is that mission compatible with venture? I keep hearing conflicting ideas on what it actually means to take money from investors. My main questions are: what would my investors expect from me? How will my life change? If the investor was a friend first, will this change our relationship? How will they feel if I don’t make them a lot of money? Basically, I’m wondering if raising venture will mean selling my soul. Any advice is greatly appreciated.

— Soul for Sale

Dear Soul for Sale,

It’s a good sign you’re thinking this way. If you weren’t, I’d have some hard news to break to you. But your trepidation could also be a sign that you aren’t ready. Venture is the right financial vehicle for visions that can’t really be actualized any other way — the kind of projects that demand speed and scale in order to survive. I’d first figure out why you’re hesitant about taking this leap. Is venture money actually necessary to get your project where you want it to go? Or do you feel that you need to become a founder? If so, that is generally a bad reason to start a company — exactly the kind that leads to your feeling like you sold a piece of your soul for a few million dollars that isn’t even really yours.

I see people cope with the responsibility that comes with raising venture capital in many ways. Some pretend they don’t care, while secretly feeling a nagging sense of dread about the responsibility they took on to their investors. Others decide to believe that all VC’s are stupid so there’s nothing wrong with wasting their money. While it’s true that venture capitalists have many consistent and exploitable failure modes as a result of investing lots of money with very little information, they’re rarely stupid nor disposable.

Venture cope is often a product of not choosing the right investors to partner with — resulting in an adversarial relationship that stems from your feeling neither trusted nor supported by your investor(s). Avoiding this looks like expectation alignment; asking potential investors how they work, what they want, and why they invest at all. Investors who are betting on your potential to make a great founder are generally less constrictive than those who invested on the belief that you would be exploiting a specific opportunity.

To answer your own question of whether you should raise, you must become really honest with yourself. What are you truly afraid of? Can you get more comfortable with that potentially happening? Are you willing to shapeshift yourself in order to be more marketable to venture capital? Does that feel worth it to do on behalf of this project?

— Moth

I have this core framing I use to categorize people: people persons and idea people. What I’m asking is whether a person is primarily motivated by an interest in people or ideas. Do they do what they do out of a fundamental desire to serve and love humans, or are they more driven by an appetite for new and novel ideas? Effective founders come in both forms, especially if they manage to attract lots of talented people of a similar motivation style. Where a person falls on this spectrum can also shift over time — many founders start out driven by a desire to actualize an idea, then become increasingly people-driven as their company grows (and with it, their sense of responsibility to the people on their team). Regardless, I’ve found that the people vs. idea dichotomy is best posed verbatim — ask a person to simply pick which one they are and explain why.

I’ll provide myself as an example. I’ve always been someone who prefers to observe a given situation before jumping in. I’ve never cared much about becoming the smartest person in the room, but I’d pride myself on picking up on subtleties in the people around me, accurately judging character, and asking good questions. In some ways this quiet, observational approach made me a bit of a blank slate, allowing others to project what they wanted onto me. Because I wanted to belong, I sometimes played along. The best example of this was my Twitter in 2021. I was fascinated by the Silicon Valley social scene I found there and wove myself into it quickly, following the breadcrumbs of validation left for me by people I admired. I got a lot out of that app as I grew up and into myself — I met my husband and several of my best friends there, grew a following for my writing, and began building the network upon which I raised my first fund.

But I increasingly felt a certain amount of dissonance with most of the startup people around me for one simple reason: I’m not technical, nor am I motivated by a driving interest in being at the forefront of ideas. If you haven’t already guessed, I’m a people person. I liked startups because of the unique people working on them and stuck around because I wanted to better understand their motivations, desires, and big visions for the world. Twitter engrossed me for a while because it let me map out who influenced who, who was thinking for themselves, and what the social dynamics and norms of this culture were. I stopped posting a few years ago in order to reconnect with what I actually value — reading people and relationship-building.

How is this relevant to VC, you might ask. While venture capital is often framed as bets on potential futures, all potential futures are revealed to us by outlier people. Those who spot the signs of a person’s future success first (and crucially, act on it by investing in them) stand the most to gain. Very few capital I investors (i.e. ones with LPs) are actually willing to invest in just a person though. It’s a perception problem — talking about the qualities of a founder that make them exceptional (with examples, of course) just doesn’t win you smart points in a typical Silicon Valley conversation, much less in a memo read by those above you. If you want to get a promotion or to raise a lot of LP money, you’re probably wise to stick to talking about ideas.

But say you decide you don’t care about either of those things. Say you’re driven by wanting to be just as rigorous about refining their perspective on people as the best idea-driven investors are about their ideas. From what I’ve seen so far, becoming a better people picker requires spending a lot of time around excellent and unique founders — developing instincts in data-rich environments. But instincts alone aren’t enough. Discernment also requires authenticity; honesty with yourself and others. What are you great at? Where do you trip up? How much can you reasonably give? What are you here to do? These are the kinds of questions I try to answer as I get to know a person. Or my favorite: are you a people or an ideas person? Why?

I grew a lot over the course of Moth Fund I, both personally and professionally. Gaining confidence tends to have that effect. Confidence is what allowed me to see that all the proof points in front of me were pointing to the fact that not fitting the VC mold was exactly what was both winning me my best deals and convincing some LPs to take a chance on me. At the stage I invest, I’m selling my viewpoint to founders in the form of a small check, and I’ve found that the weirder that viewpoint is, the more interesting I am to the type of outlier people I want to back.

Learning to lean into my weirdness has taken many shapes. Mostly it’s looked like embracing what comes to me naturally: I’ve always been much more interested in understanding people than ideas, get immense gratification from building lasting relationships, and consider it a lifelong goal to improve my discernment and refine my taste. This often shows up in how I spend my time: I rarely take pitch meetings (if a founder is fundraising already I probably didn’t get there early enough), always have a creative project I’m actively working on, and spend a significant amount of time striving to understand and translate myself to the page. Cultivating a view of the world that no one else has is an edge I consider critically important to Moth’s success, as well as something that requires continual cultivation and critical refinement.

The type of people I aim to back are weird. Not just any weirdness though — I look for a specific kind of pragmatic strangeness found in outlier people who are striving to see reality clearly and make a lot of money. The pre-seed rounds I specialize in usually boil down to a founder and I choosing to partner with one another because we recognize that each of us brings something unique to the table. To materially benefit from this relationship, I must deeply understand the skills a successful founder needs to possess and invest a diversified portfolio of bets against this continually-refined mental model.

My view of the world is that people develop to different extents. While some become extremely spikey in a way that makes them an incredible founder, most do not. It’s my job to find, build a relationship with, and bet on those who do. In evaluating a person’s fit for venture, I’m aiming to understand the characteristics of their spike, how they source their motivation, their commercial aptitude, and whether they’re an outlier with a unique magnetism that draws other people to want to work with and help them. How this breaks down:

• Spike: I want to understand what a person’s greatest strength is and how that functions doubly as their greatest weakness. When extensively developed, this strength should result in their having hard-won taste as the result of deep competence and expertise in an area.

• Motivation: I look for two things here — obsession with the thing they’re working on, as well as evidence that they’ve had a difficult formative experience and emerged with hard-won proof of their own ability to persevere. I like tenacious underdogs who are determined to change something big.

• Commercial instincts: Here I’m essentially asking whether they’re both capable and motivated to capture the value that they create. Simply put — a successful startup founder needs to be hyper focused on making a lot of money.

• Uniqueness and magnetism: I need to see that the person in front of me is an amalgamation of characteristics that I’ve never seen together before but am personally compelled by. Do I want to work with/for them? Are they a magnet for top talent? Being an outlier with a clear track record of playing their own game generally results in a person possessing a unique gravitational pull.

I’ve learned that when a founder is difficult to pitch on paper, that might mean they’re a good fit for Moth. Investing at this stage and through this lens means that there’s a certain shape to a Moth-like deal — generally pure person bets (usually zero product) and quieter rounds raised quickly in order to buy time/resources/talent so the founder(s) can get back to building and set themselves on a clear track towards raising any kind of seed round they want. One of the main learnings from Fund I was that pre-seed is the best time for my small check to meaningfully contribute to the company’s success while getting enough ownership to continue to be worth something if the valuation skyrockets at later rounds. In practice this means that I avoid popular seed rounds and shamelessly follow my nose for talented people wherever it may lead me — hence the strategic necessity for me to be confident in my taste. I’ll be the first to admit I make mistakes though, which is why I take a 80/20 approach here: 80% of Fund II will be made up of the core pre-seed people bets Moth is becoming known for, while 20% is earmarked for betting on early stage wild cards (i.e. seed rounds I missed or founders who didn’t raise a pre-seed).

Moth Fund is designed around a singular focus on providing pre-seed founders with what they need — aiming to align the incentives for me to take a long-term approach with talented people and invest at the speed of the shared trust we build together. This results in a fund devoted to finding exceptional founders before they’ve been priced by the venture market and being one of the first to do so, using my check (either grant or investment) as a stamp of belief in them and their fit to become a multigenerational founder.

My confidence in this approach stems from my commitment to continually steering myself away from the straight and narrow path. I’m lucky that the path I’m on often intersects with other stubbornly independent and strange humans that I get to learn from and support on their journeys. Investors often ask each other what ideas they’re excited by and my honest answer is something like: I’m excited about specific friend groups, nascent talent diasporas, and a handful of emerging subcultures that are showing signs of following their own curiosity. Moth’s generalist portfolio reflects this focus and will continue to paint a picture of where I find the best talent building at any given time. I’ve accepted that my taste in founders will never be easy to sum up in a few words — betting on outlier people is an inherently moving target. Instead, Moth will always be best understood by looking through its portfolio (now 34 companies) to connect the dots yourself.

Below are some objections I’ve heard against Moth over the past few years and my thinking. Not solicitation in any way.

#1: Moth’s fund size isn’t big enough to get meaningful ownership in companies.

My checks are small and I write a lot of them — my portfolio construction is designed for a straightforward power law distribution where one or a few breakout companies will 10x+ the fund without needing to own a big chunk of any one company. These incentives allow Moth to be highly collaborative with basically all other investors. Over time I plan to prove my right to more ownership but for now, I play where I can punch above my check size’s weight and optimize each fund for outsized returns.

#2: I don’t have the makings of a VC.

It’s a fact that I don’t have a long angel investing track record or pedigree from a top firm. I didn’t found a company and don’t even have aggressive finance girl traits. I went to film school, did a variety of product/design/marketing roles, and discovered a love for investing by becoming a Sequoia scout. What I look for in founders is based on what I’ve observed about the exceptional people I found myself surrounded by — primarily observations about the founders I worked with, consulted for, and became embedded in networks alongside. I became obsessed with understanding and serving these outlier people. Sharing my writing on the subject over the past four years demonstrated that I speak their language — attracting and continuing to build trust with the kind of ambitious future founders I aim to back.

#3: Moth won’t become known for anything if I don’t specialize in a sector.

I want Moth to be known for taste, thoughtfulness, and putting people first. While hot sectors change and business ideas pivot, people continue to be the core atomic unit of this industry. I’d rather get fewer high-quality deals from people who know my taste and can attest to my value as an investor than lots of deals of questionable quality that ask me to x-ray the future and pick the ideas that will win. Focusing on the founders instead means I have very different relationships with/perspective on the ones I do end up backing — I’ve generally known them for longer, understand their strengths/weaknesses, and am considered a peer, confidante, and thought partner.

#4: My access to the best founders in my cohort isn’t a durable edge on which to build a firm.

This is true, but fortunately a fruitful source of dealflow at present and also not all I invest in. I view my proximity to the best founders of my generation as long-term relationships that will prove my ability to pick well over time. I’ve observed how the incentives of this industry reward VCs for optimizing for optionality constantly, translating into noncommittal flaky behavior that creates a terrible experience for founders. The best way to avoid this trap is by aligning myself with long time horizons as a sole decision-maker dedicated to making investing my career. This industry is changing and my approach will evolve with where I have founder PMF.

I’ve been watching Wimbledon lately. The players’ mastery fascinates me — what qualities led them to get so good? Their excellence starts with the presence they bring to every stroke and movement — a powerful quality that often ends up dictating the outcome of the match. Tennis, like all professional competitive sports, is about the pursuit of perfection by athletes who are all at minutely different levels of excellence — winning comes down to a player’s ability to react to each new shot with fresh eyes, steering the game toward their strengths and their opponent’s weaknesses as much as possible.

We see a similar trend in business. At the beginning, a startup’s strength is probably its ability to execute — the company’s speed and capacity to see opportunities clearly without being beholden to the past. Take Microsoft in the 1980s, when Bill Gates made the strategic decision to retain the rights over PC-DOS, setting Microsoft up to capture a great deal of the value accrued at the software layer and effectively commoditizing PCs. I highly doubt Gates knew how smart a move this was, but he was able to make it because Microsoft had next to no incentive to maintain the status quo and shipped fast (why they won the contract with IBM). More impressive is when large companies consistently see, capture, and capitalize on opportunities over decades, playing to their strengths even as those strengths change (Microsoft has done this sporadically, notable for moves like acquiring Forethought aka PowerPoint and more recently, the OpenAI deal). In tennis, this is the equivalent of a player consistently winning matches even as their opponents change and their body ages.

Winning over decades involves stepping back and striving to see clearly, identifying the opportunities your team is uniquely positioned to capture and compound on. I call this discernment. Discerning founders do everything they can to stay rooted in the present — forgiving themselves a thousand times so they can continue to see the bigger picture and act. Discernment is built on the back of countless hours of practice — 10,000 hours, if you ask Malcolm Gladwell. Putting in this time is easier if you simply derive enjoyment from playing the game you’ve chosen. Djokovic put it best: “I can carry on playing at this level because I like hitting the tennis ball.” People who have achieved mastery often speak like this — they believe that they’re doing the thing that they were expressly designed to do, so being present is something to be relished, not avoided.

This sense of destiny and something bigger than yourself is important. Mastery requires a purpose — a solid foundation of your sense of the good life, some degree of felt alignment with it, and the driving belief that the challenge you’re tackling will bring you closer to the ideal you hold. It’s a hunger for the catharsis of fixing something a person feels to be wrong (either inside or outside of themself) coupled with a specific vision for what it would look like for things to be right and the tenacity to do whatever it takes to make that vision real.

Execution, discernment, and purpose are three of the key ingredients to mastery — coupled with a lot of luck around timing and finding the right people to help you. I look for all of these traits in founders. Execution is the most easily observable, made evident by how they approach new problems/info. Discernment can be glimpsed in their reflections — they should have exchanged their innocence for wisdom, not just experience. Purpose usually shows up as main character energy — a sense that this is not someone you’d want to bet against. In searching for these qualities, I’m striving to see clearly too: approaching every founder anew, observing my reactions, and using every interaction to inform my judgment, without haunting or hindering it. I’ve found shared kinship in this pursuit amongst many of the most interesting founders — a fierceness in our collective desire to be very good at what we do and an incessant interest in the craft of becoming better.

By all objective measures, being a venture capitalist is a weird job. The industry is really small (3.4k firms in the US as of 2023), really new (first firm founded in 1946), and largely a game of luck. For the solo capitalist, it’s mostly a sales job within a multi-sided marketplace; you sell your brain to LPs (your customer) and sell your money to founders (your users). Somewhere in there, you need to have made some smart-on-a-ten-year-time-horizon decisions.

I wrote this for a friend who’s new to investing independently and trying to figure out if it’s the right job for him. I don’t have an answer to that question, but what I do have is lots of notes and fresh reflections on what’s surprised me most about operating alone in this weird world of early-stage venture over the past year and a half:

1. If you derive satisfaction from refining a craft, don’t go into venture yet.

2. There are many ways of winning and the best one is entirely new.

3. Create coworkers.

4. You’re all alone with your thoughts.

5. A good fund brand bat signals your people and deters disbelievers.

1. If you derive satisfaction from refining a craft, don’t go into venture yet.

This filters out a ton of people if they’re honest with themselves. The people who should be early-stage investors get their gratification mostly from being of service to others and refining their thinking. They’re usually naturally patient, innately critical, and often a bit obsessive. Harnessing one’s intensity to make winning decisions about people, problems, and the future is the name of the game (and you should know which one of these you’re best at1).

Many people try out careers in venture and then wind up leaving after a year when it stops feeling novel and starts feeling like they’re floating in lonely limbo without any markers of success. That’s because the craft of venture is not for people who derive their satisfaction from external indicators of progress — it’s for people who find the development of their relationships and refinement of their internal model of the world to be motivation enough to keep going.

In the beginning, it’s best to derive your confidence from somewhere outside of your identity as an investor. Any honest person can’t hang their hat on being something they won’t know if they’re good at for five years without feeling like a fraud. It’s wiser to pivot into a venture career after becoming competent using more fast-paced feedback loops — generally from starting or working at a company. The lack of feedback loops in venture is much more tolerable if you have some confidence to stand on while staring into the ambiguous abyss of your investment decisions.

2. There are many ways of winning and the best one is entirely new.

Investing is not really a “job” with a standard set of day-to-day duties. It makes more sense if you think of venture as a business model that can work (aka make money) in many different ways. Here are five individual investor archetypes I’ve noticed can produce outsized returns in the early-stage venture game:

1. Philosopher: hangs one’s reputation on their predictions about the future

2. Hustler: simply outwork everyone else and are great at networking

3. Hawk: most competitive, gets a thrill out of the fight to win a deal 

4. Friend: confidante and coach to founders, often founders’ first call

5. Celebrity: a person widely respected for their work/knowledge/skill

A good archetype for you is whichever one you can sustain the longest. A great archetype for you is one that no one else is doing and you have some sort of signal works. This is why inexperience can be such an asset in early-stage venture — you’re more differentiated at the start.

Some good advice I got: build your fund’s structure and strategy around allowing yourself to invest in whichever way you most enjoy and are naturally good at (admittedly, it will probably get harder and harder to stick to this as your fund scales). A general rule of thumb is that the earlier you invest, the more interested in people you should be. Examples: if you like being a friend to founders and want your fund to function as Switzerland (i.e. not compete with anyone), write small checks. If you like to fight and are naturally hawkish, it might make sense to set yourself up to try to lead rounds. If complex problems and futuristic theories are what get you excited, investing in series A companies that fit into where you see the world going could be quite gratifying. If for some reason you love living in spreadsheets, consider growth investing (and don’t follow literally any of my advice).

3. Create coworkers.

It’s literally impossible for you to do this job alone, but you also are doing it alone. Assigning labels to the abstract working relationships you form (even if the labels only exist in your head) helps quell loneliness by calibrating your expectations of the people around you. A breakdown in basic terms:

1. Peers — these are the people I started investing with and/or raised a fund alongside. We’re all “freshman” and ignorant in different ways. It’s safe to ask each other dumb questions without worrying about losing credibility.

2. Mentors — several years or a decade ahead of me. These are people I respect and can see bits of myself in. I don’t take their advice verbatim because they’re different from me in key ways, but I do turn to them for strategic guidance around what they learned walking a similar path to my own.

3. Funders — these are my LPs and other important people I need to believe in me. They make my job possible, and it’s important I present my best self to them (no dumb questions allowed).

4. You’re all alone with your thoughts.

Sitting on a pile of decisions you have no way of knowing the quality of for a very long time. You should feel a lot of responsibility to the people you took money from. You should probably get an executive coach to work on your relationship with yourself. Time at work ranges from being brutally critical about all the things wrong with a person/idea to being a switched-on salesperson of your money/approach to engulfing yourself in the emotional art of helping and building trust with a person on whom you’ve made a sizable bet.

In many ways, the job of the writer and the job of a VC are quite similar, in that they both ask you to produce an original end product (in the writer’s case, articulated ideas and stories; in the investor’s case, a differentiated portfolio with outsized financial returns) without much of a map for how you get there. The reason professional writers complain about writing so much is that it’s really difficult to wrangle your brain into producing uniquely interesting thoughts all the time, and highly frustrating when you consider it your job to do so. Making good investment decisions is similar; just with the added element of also being highly social. Taking the quality of your self talk seriously seems superfluous but is an investment that will result in better decisions.

5. A good fund brand bat signals your people and deters disbelievers.

A lot of the game of investing is won by getting people to think of you — a sign that you’ve built the kind of moat we call a strong brand. Remember: a fund is just a pile of money with a person on top to sell it. As an investor, putting down stakes in the ground about what you invest in saves you a lot of time in the long run because it allows people to self-select for fit — give reasons for the wrong people to opt-out and the right people to reach out (this is the main function of my publishing this writing).

I’ve been surprised by how much it’s benefited my fund to make Moth’s brand (i.e. what I invest in and look for) difficult to summarize in a sentence. For small early-stage generalist funds like my own, quality matters much more than quantity. Quality deals almost always come from trusted sources who resonate with my taste, not from a list of random companies for which I have no context.

A brand is a promise to show up in the same way time and time again. Good brands are built on being decent and principled with all of the people you interact with. Venture is a tiny world where investors are in the business of selling their brains, relationships, and money. Doing venture solo without losing your mind requires quite a bit of internal motivation, discipline, and a plethora of people you both trust and believe in enough to build your career around. Lastly and of utmost importance: remember that fear of failure fades into the background if you focus on leaving everyone you encounter along the way better than you found them.

PG had a great post back in the day called the Hacker’s Guide to Investors that detailed how to understand, relate to, and work with early-stage venture capitalists. I’ve been thinking about this a lot lately and wanted to tack on a few things, particularly for young people interacting with this corner of finance for the first time.

I’ve noticed that the founders who find raising venture capital awful are often the ones who have trouble separating their personhood from the persona and mentality they need to adopt to successfully fundraise. If this sounds like you, I recommend reading about Kegan’s stages of adult development (specifically stage five, the interconnected mind). More tactically though, here are some fundraising things to know:

1. Fundraising is brain damage, so spend as little time doing it as possible

2. Create an alter ego who you don for fundraising purposes

3. Don’t spend a lot of time with VCs if you don’t need VC $

4. Only talk to investors with decision-making power, preferably angels

5. You know more about your business & domain than 90% of investors

6. Momentum matters and sequencing is smart

7. People don’t belong on pedestals

8. Beware of intellectual dementors and clout demons

9. People will help you if you ask for what you want clearly and concisely

1. Fundraising is brain damage, so spend as little time doing it as possible

Raising money requires you to perform for the money-wielders, distracting you from the real work of building. However, nailing the performance provides a vital ingredient to enable the real work! Minimize time spent performing as an act of self-preservation for your psyche and rootedness in reality (i.e. keep your ego in check).

2. Create an alter ego who you don for fundraising purposes

VCs need to believe that your company could be a billion-dollar business and generally lack imagination — you need to paint a vivid picture of this path for them, starting with the striking protagonist character you play in your company’s story.

Your alter ego should never lie, but it should be completely comfortable showing the fullest expression of your ambition to people who probably intimidate you. Fundraising is a snap judgment game — most VCs are trying to pattern-match you to a founder archetype who already won. They index primarily on IQ, self-belief, experience, and personability (in that order). A general rule of thumb is that to be taken seriously in SV, male founders would benefit from acting warmer, while female founders are taken more seriously when they act colder. Both benefit from acting a little entitled.

3. Don’t spend a lot of time with VCs if you don’t need VC $

Investors at big firms are (probably) not your friends. They will try to make you feel like they are, but at the end of the day they’re unlikely to be loyal to you unless they’re invested. Remember that a VC’s job is to make a diversified portfolio of bets — you are only one. Most founders find being around VCs distracting and draining because they feel pressure to perform the role of ‘impressive person.’ If you can’t immediately capture value from your performance… why waste your energy?

Angels generally don’t expect as much of a performance — especially ones who care about you as a person. They are more personally invested (literally) and are likely to be well-versed in the reality of building companies themselves. Which leads me to…

4. Only talk to investors with decision-making power, preferably angels

Don’t talk to associates or analysts, it will most likely lead nowhere and you’ll be stuck with that person as your designated contact in the firm’s CRM forever.

Do talk to angels, solo GPs who operate like angels, and partners at firms you admire (once it comes time). When talking to investors who make decisions, expect the call to be more conversational in nature (not necessarily a pitch, read the room) and know that if they’re a partner at a firm, the whole point is to get to the next meeting.

How to meet angels/GPs: you probably already know one or two of them (if you don’t, ask the best-connected person you know who they know). Tell the angel/GP about what you’re working on, solicit advice/feedback, and crucially, ask for intros to other investors they like. Repeat this again and again until you’ve built an investor network.

5. You know more about your business & domain than 90% of investors

Which is fine! Just don’t expect the average investor to provide much value beyond money and connections. This makes the 10% of investors who can be legitimately useful to your business worth their weight in gold. Develop litmus tests to identify the valuable ones quickly and avoid wasting your time trying to convince nonbelievers.

6. Momentum matters and sequencing is smart

Remember that our goal here is to spend as little time fundraising as possible — which requires being strategic about the order in which you talk to investors and how you talk about where things stand as you progress through the raise. The combined force of controlling those two variables are what “generates momentum” during your fundraise process. Sequencing investor meetings as follows can help do this:

1. Make a list of all the investors you know and can get introduced to, ordering them by the ones you most want on board to the ones you couldn’t care less about

2. Talk first to a few low-stakes investors at the bottom of your list to practice your pitch and identify common investor questions and critiques you’re going to get

3. If available to you, next get a few investors who already wanted to give you money on board so you have a dollar amount you can say you’ve raised

4. Work your way up your investor list, talking to the investors you most-want-on-board-but-still-need-to-convince last (this optimizes your odds they say yes)

This all goes by much faster if you court investors similarly to how hot girls treat their many potential suitors. If your raise is already a little taken and you exude an air that you don’t need them, mimetically-minded investors become much more interested.

7. People don’t belong on pedestals

You will most likely meet your founder/investor/operator idols at some point in the fundraising process. If you’re anything like me, you will worry intensely about not making a fool of yourself. It will probably go ok, but not as amazing or illuminating as you’d hoped. You might leave and feel a deep sense of lostness set in. This is all very normal. In time you will see them in increasing clarity, often noticing the differences between your and their values and why you would not enjoy living their life at all.

Also: the people on pedestals probably hate being there. It’s lonely, hard to trust that the intentions of the new people around you are pure, and you often feel like you’re constantly letting people down. In the end, idolization hurts everyone involved.

8. Beware of intellectual dementors and clout demons

Intellectual dementors will try to eat your ideas and interestingness — not necessarily to copy you, but to wring your brain dry to amass knowledge themselves. They often play mini IQ games/tests of will in conversation and masquerade as investors while never actually investing. Clout demons are similar, but view people less as brains and more as stepping stones towards supreme social status. The power move to protect yourself from both is to simply abstain from playing their games — give as little info on yourself and your ideas as possible and reflect their questions directly back at them.

9. People will help you if you ask for what you want clearly and concisely

The beautiful thing about this industry is that demonstrated self-belief (“ambition”) will take you far. You just have to know 1) what you want and 2) how to ask.

Knowing what you want requires a lot of upfront soul-searching, followed by strategic and long-term thinking once you’ve committed to a thing (I can’t really demystify this more). Once you’re all in, I highly recommend diligently keeping a list somewhere of the top three things you currently need help with so when people ask, you’re ready.

Knowing how to ask is partly timing and partly tone. You don’t want to make people feel like you’re using them but you do want to use your social capital for things you care about. General rule of thumb: ask for things either 1) after a positive interaction or 2) completely out of the blue with a concisely written and compelling email/text. Tone matters because you don’t want to sound desperate and you do want to show you know how to play the game (write like the founder you most admire talks).

Here’s one last secret: once people start helping you and you start helping people, you all start strongly wanting each other to win. Human brains are funny like that — once we’ve taken action on behalf of something, our brain assigns more value to said thing. Tim Keller: “The feeling of love follows the action of love.” Love is a strong word here, but the point stands — help people help you. Startups are long-term games, so it only makes sense to do them with people you truly want to be around for a very long time.

My main learning after a full year of Moth Fund has been to bet on unabashed capitalists. Having grown up in an area of Northern California dominated by hippies, this was a breed of human I’d barely been exposed to. Where I’m from, capitalism is seen as evil and a system no “morally pure” person succeeds within.

This is obviously wrong, something I learned over the last year with every Zoom call I had with a kind capitalist. Cracks started to appear in the story I had been telling myself once I got to know successful entrepreneurs who seemed to not only be good people, but to be extra good actors, using their money to make more positive impact than they could have without it. My takeaway was that capitalism is extremely effective at giving action-oriented people with a vision for how the world could be better the resources they need to scale their ideas to become widely available. To put it simply, I became market-pilled by seeing the market work its magic right in front of me.

But it was the technologists themselves and their positive sum nature that I found myself most fascinated by. In contrast to zero-sum industries such as manufacturing that give capitalism a bad rap with their many negative externalities (namely emissions), it seemed to be a different, much more promising story for positive-sum industries like technology. Over time, I codified three ways of classifying the technologists I met by their actions and altruism — the throughline to all three archetypes being a shared enthusiasm for creative ideas, progress, and creating a better world. Through the process, I became obsessed with understanding the defining aspect of the successful entrepreneur — their commercial aptitude.

Part 1: Types of Technologists

Researchers. The people who come up with big ideas that push progress forward are often researchers. They’re non-commercial and satisfied with their contributions existing only in theory land. Researchers are instrumental at the beginning of a discipline’s creation but generally become less useful as the field matures and commercializes. Researchers are commonly found in academia, gain respect by writing and publishing their ideas, and usually make far better smart friends than they do venture investments. Researchers are often the biggest critics of the commercialization of their ideas — sometimes because they are thinking on longer timespans and other times because they are jealous of others profiting from their work. The best example of the researcher archetype is Alan Turing, one of the pioneers of (theoretical) computer science whose contributions include Turing machines, the Church-Turing thesis, the concept of undecidability, and the Turing test — all of which are still being applied to both research and commercial contexts to this day.

Hackers. These are non-commercial people who like making stuff. They’re executors and craftspeople — the creators of open-source projects who generally capture very little of the value that they create. Hackers are perfectly fine with this — for them, it’s much more about making the idea in their head real than it is about profiting from or growing it. Their technical skill makes them fully capable of building a thing that they materially benefit from, but they don’t want to scale the things they build because of how it changes the way they feel about the work (instead, they often make excellent founding engineers). This is why hackers can be one of the most frustrating archetypes to a venture investor — they’re so close to being a brilliant founder yet their inability or unwillingness to be commercial often limits what they build from ever reaching venture scale. The most infamous hackers are the ones whose anti-capitalist ideologies got them into trouble — namely Aaron Swartz, a co-founder of Reddit with a hacker heart who believed that everyone has a right to access publicly funded research and ultimately died from the consequences of that belief.

Entrepreneurs. The epitome of commerciality is embodied by the entrepreneur. They’re the weird, obsessive, extreme ones who always bias towards action and believe themselves to be outlier enough to win. Entrepreneurs shamelessly want to capture every bit of the value they create and usually believe that doing so will allow them to do even more for the people they’re serving and selling to. They’re the ones who are constantly guessing how much people would hypothetically pay for something and often know a weird amount about the companies they do business with. The best entrepreneurs are excellent at prioritizing what will make them the most money long-term and generally don’t get distracted by irrelevant details or intelligence games like jargon. Jeff Bezos is a great example of this archetype; Amazon has been explicitly hyper-commercial from the start by focusing solely on long-term growth and serving its customers.

Analyzing these archetypes and making calculated bets on where the money will be made is the job of the investor (and within technology, primarily the venture capitalist). Investors are separate from researchers, hackers, and entrepreneurs in that they are critical over creative — yet still share the commercial mindset of the entrepreneur. The work of the investor takes place mainly in their head since their only direct output is their decisions. These are the people who walk into a room and immediately size up square footage and deduce the margins of the business in question. They think about the world in terms of money and are frequently a little impatient. Investors have enough risk tolerance to put their money where their mouth is regarding what they think the future holds on the technological frontier, but not enough conviction to place a single bet on one idea. But at a baseline, they believe they want and deserve to win, unlike researchers and hackers. The investor mindset is best epitomized by Warren Buffet, who Alice Schroeder described as “able to see the essence of a business model as if you see an animal and he sees its DNA. He isn't interested in whether it's furry, all he sees is whether it can run and how well it will reproduce, the two key elements that determine whether its species will survive.” 

Part 2: Zeroing in on the entrepreneurs

Understanding these archetypes is obviously important to venture capitalists. We need to keep tabs on the researchers for a peek into the future, recruit the hackers, and invest in the entrepreneurs. The more interesting question is: what mindset sets the successful entrepreneur apart?

I’d argue it’s chiefly a commercial one — generally developed through sheer experience starting and running businesses. Read the biographies of storied entrepreneurs and you’ll notice a theme: almost all of them learned to make money from an early age. Spending time in finance, being born into an entrepreneurial family, or joining an early-stage startup that gives you a lot of ownership and forces you to think like a business owner with a bottom line also seems to teach this skill. Commercial instincts are the result of exposure, perhaps even more than inherent talent.

The makeup of a successful entrepreneur is a special blend of wanting to make the world better and possessing enough commercial aptitude to figure out a way to do it in a successful and self-sustaining way. I’d argue that the most common motivator for commercial success is a strong desire for autonomy. The benefit of earning your own capital by founding a company is that it enables you to create something independent, lasting, and free from outside influences (in contrast to the reliance nonprofits and the public sector have on external entities).

Another more surface-level characteristic commonly found in successful entrepreneurs is that they’re voraciously curious and find great enjoyment in winning commercially. There’s a reason entrepreneurship at an early age is such a common pattern in those who win — the easiest time to get a taste for what winning feels like (and learn that losing isn’t so bad after all) is while your ego is least sensitive to failure. As people grow older, they’re less willing to try new things and often develop elaborate moral justifications to conceal the fact that they don’t think they’d be capable of making and selling something people want. A fear of failure seems to be the single most limiting factor to both entrepreneurial success and the creation of more entrepreneurs.

This begs the question though, why be commercial in the first place? Well, being commercial is what enables the entire capitalist system to exist. While I’m under no illusion that capitalism always creates good outcomes or successfully factors in all long-term considerations, I still believe it’s the best proven economic and political system we have to organize our society today.

I’ve noticed that most critiques of capitalism seem to be talking more about the product of human nature without any shared moral framework than the aforementioned system itself. Greed and capitalism are grouped together in our societal consciousness as synonymous despite the actuality being that greediness is an independent characteristic of human nature that will exist in any system humans are found. Positive-sum environments like technology are where capitalism shines, letting everyone win by turning something small into something big at breakneck speed. 

Similarly, critiques of commerciality are more often about the aesthetics of the mentality than any real issue with its outcomes. As a society, we generally don’t find successful business people very sympathetic because they don’t share enough of themselves with the world for us to empathize. It’s also true that commercial instincts, taken to their extreme, can lead a person to behave too transactionally. Extremely commercial people often exude an air of wanting to take something from you, which no one likes. 

But most people do want something from you — it’s just on what time scale. Their urgency is what dictates whether the experience will feel good or bad on the receiving end. After all, being transactional on the scale of a human lifetime is how most productive partnerships are structured. Long-term commercial instincts lead a person to think in a positive-sum way — surprisingly similar to the demeanor of capitalist-averse researchers and hackers. The difference is that those with commercial instincts don’t have a complicated relationship with winning within our economic system; they aren’t afraid of materially benefitting from their time and money investments. Warren Buffet said it best: “Success means being very patient, but aggressive when it's time.” It’s only through the prosperity produced by capitalism’s meritocracy that those who win like Buffet can (and do) give back towards causes they care about through philanthropy, strong redistributive tax mechanisms, etc.

At its core, being commercial is a mindset. At a bare minimum, you need to believe you deserve success — or at least, believe you are no less deserving than anyone else. Capitalism is designed to equip charismatic individuals who want to transform the world into a better place with the resources they need to do so. Whether the end they’re motivated by is power, fame, or faith, unabashedly capitalistic entrepreneurs know that wielding money as the tangible product of their work is the most effective means by which to actualize their impact at scale.

Special thanks to the very bright star that is Tara Seshan for clarifying convos and draft reads

Highlights:

• As a thesis-driven, research-centric investment firm, Compound spends most of their time discussing research and developing theses internally. They also use their collective online presences as Rorschach tests for finding people who align with their approach and care about topics they’re discussing at a similar depth.

• Michael defines deep/frontier tech as areas that start as vertical technologies and then gradually become more horizontal — indicating they are now in the next phase of commercialization (e.g. mobile, AI, likely in the future: VR, AR, crypto). These spaces are verticals today but will become platforms tomorrow.

• Three areas in which Compound has been spending significant time lately are robotics, decentralized energy grids, local software, and AI. The firm has been investing in AI for many years and believes that the key question to ask to discern what will win shifted recently from ‘What do you believe that no one else does?’ to ‘What can you believe, consistently ship, and run this marathon as if it’s a sprint for the next few years as capital flushes its way through the system?’”

MM: Hi everybody. Today I’m joined by Michael Dempsey, the managing partner of Compound, a thesis-driven, research-centric investment firm. Prior to founding Compound, Michael worked at the predictive analytics startup CB Insights and at Crane Partners, a multi-strategy hedge fund.

Our conversation covered how Michael views venture capital and frontier technologies, how Compound develops theses, and how he thinks about several of those theses in the areas of robotics, decentralized energy grids, local software, and AI. I hope you enjoy.

MM: Hi, Michael. Welcome to the podcast.

MD: Hey. Thanks for having me.

MM: Of course. By way of introduction, my first question for you is what do you think has informed your outlook on investing and what drew you to venture specifically after spending time researching private markets?

MD: Yeah. I originally got my start at a hedge fund and I was doing a bunch of different types of investing. I was doing long-short and public market investing and then I was doing private equity from Asia to the US, and a lot of stuff we were focusing on around the private equity was these tech companies that were possibly disrupting companies we were buying and helping. I think a lot of that kind of lesson and learning of working with companies that were being very majority owned was really compelling to me relative to public markets where it felt very zero-sum, but I wanted to learn and understand a bit more about how the tech ecosystem worked. As I joined CB Insights pretty early on, got to see just a total funnel of data every day and try and make sense of it all related to private markets and also got to talk to a lot of really interesting people who wanted to understand data on the venture investor side, whatever, and then on the startup side, as we were writing more research-centric reporting, wanted to help educate us on these various spaces.

The thing that I always say was people didn't... It never was clear to me why venture was so kind of consensus-driven. Hedge funds is all about information asymmetry. You think about your best ideas, you work on them, once you have a position on you really kind of then talk about it or venture felt a little bit the opposite. That I think kind of informed a lot of how I've thought about venture and just the right to win and where there were open spaces to develop I guess what we would previously call long-term alpha or long-term edge in investing. I think investing in general is really, really hard, and it should be really hard. I think we lost that the past few years, candidly, but I think that a lot of seeing all of these things across both kind of the public market, private market side, and then on the startup side led me to just think about a very research-driven and kind of thesis-driven way. We call it thesis-driven research-centric investing, but yeah. I think that's probably the main way in which it informed how I wanted to approach investing, and then, I don't know, the past decade has changed a lot of that.

“It never was clear to me why venture was so kind of consensus-driven. Hedge funds are all about information asymmetry. You think about your best ideas, you work on them, once you have a position on you really kind of then talk about it or venture felt a little bit the opposite.”

MM: Yeah. I'm curious to hear more about that. How have you evolved your thinking on both markets and then venture and investment more broadly?

MD: I think probably have come to appreciate market participants more. Mostly the simplistic way of framing that would be at a certain point of time, you realize that you're essentially participating in a market with a bunch of people and you need to understand how those people behave, how they act, and how that impacts a given market. In public markets you have a bunch of different styles of investors who do all sorts of different types of things, fundamentalist, momentum, activism, et cetera. In venture, you have just a bunch of different personalities and these personalities all have different heuristics for what they think make a good company, for what they think make a good founder, and they all have different incentives.

I think the incentives are wildly different across venture than it is in other asset classes where you have big funds that are sitting on large fee structures and the incentive is to index a space, you have small funds that the people managing them are making very little money and their incentive is to try and grow and build a firm and generate outsized returns, and there's a bunch of things in the middle of that. But I think understanding the game you're playing and who you're playing that game with is really important and has changed over time where you have to be realistic and comfortable with the idea that what you view as the best way to do this investing thing is not necessarily the way everyone else will behave, and that matters. I think that's changed a lot for me, and it's also been a point of maturation, of realizing there's a bunch of different ways people invest in venture and all of them are correct and incorrect at the same time.

I think that as that's changed, you also have to be realistic about where people are in their kind of life cycle and how that influences how they behave and what they're willing to do. We talk a lot about firm building versus fund building, as an example. I know we've talked about this one-on-one before as well. Again, just these things change. I think one of the things I believe is over the past few years as markets have corrected, people believe that everything's going to go back to a more responsible area. I think if you just look at who the market participants are and how they've learned how to invest, I'm not entirely sure that responsibility is ingrained in the vast majority of venture investors today. That will mean that the game being played could look very different than what a prior generation might think it should look like. I would say I'm more aligned with the prior generation often than the current.

“One of the things I believe is over the past few years as markets have corrected, people think that everything's going to go back to a more responsible area. I think if you look at who the market participants are and how they've learned how to invest, I'm not sure that responsibility is ingrained in the vast majority of venture investors today.”

MM: Where do you think it's headed? Do you think it's headed more towards where it was a decade ago?

MD: Probably not. I think you'll see consolidation, churn, all the stuff that everyone's talked about. I think that you have compression of returns, which is what happens when any asset class institutionalizes, and I think that likely you'll have a lot of people that maybe have very different frameworks. I've written about a post on this called Get Rich or Die Tryin’ and this idea that people are just continuing to go as far out on the risk curve as possible and doing it in a very kind of chaotic way. I don't think that behavior is going to change.

I think that there's also... There might be talent flows in and out of venture, for example, but that talent might flow from someone being a GP to becoming an LP and how they think about the world will still be the same, and so they'll just allocate capital to people that have a similar viewpoint. So I don't think we have some... I think we have a big reckoning in terms of people's performance is going to get destroyed and that will create more churn. I don't think we have meaningful shifts in behaviors outside of maybe sector-specific or maybe some apathy-specific things where people are like, "Software is late cycle, so I want to do crazy things and go the American dynamism route and things like that." But I don't think it's as Back to the Future-type thing as people are talking about.

MM: Yeah. All these different theses on where the alpha is. What is an opinion of yours about investing that you think the average investor would not agree with?

MD: Yeah. There's a lot. I would say the two that come to mind are we take a very prescriptive approach to investing at Compound. What we do is we look at a bunch of categories, we build collections of futures we believe in, and we have founders fit within those or shatter them. I think there's strong signal to both. We don't think we're geniuses in these areas, we just think we're pretty smart. Most VCs in my entire career are always like, "You are not smarter, better. You need to let founders show you the way of the future," and are very anti this kind of more prescriptive approach. We deeply believe that this is the best way in which we can partner with founders and the best way we can build a view of the world that we can deploy capital against and help our founders by having high context.

“We deeply believe that this is the best way in which we can partner with founders, build a view of the world that we can deploy capital against, and help our founders by having high context.”

The second would probably be I fundamentally don't believe that all founders are good founders, meaning this idea that this person is a great founder because of who they are, no matter what they do, I think is insane. I think it's insane because founder market fit or founder product fit more specifically is very real. I think that especially in this world in which we used to have much less capital to do bridge rounds and the bar for series A was incredibly high, we used to see a much higher velocity of pivots, so this idea of back a founder, let them pivot around, I actually think made more sense. There was also just less capital and way fewer founders. I think now there's just a glut of all of those things, and so what that means is that founders pivot less and also pivot less radically for a given entity. They might shut down their company and start a new one and go raise but cap table might be different, et cetera. So this idea of, "I'm going to back a founder because they're incredible and let them figure out what kind of startup they're going to build," I think is largely insane sans a few people.

MM: It's a very good one. How do you define what you invest in more broadly and what do you think that people often misunderstand about the category that you invest in?

MD: What we invest in at some point was called frontier tech, and that was something we made up at CB Insights. There's now called deep tech. There's a bunch of different definitions of this kind of feeling of company, and I think that that can be defined in two ways and they're kind of mutually exclusive in some ways. One is the framing of where in the commercialization phase is a given technology, and so that's where I think I would say is emerging technologies that have yet to have material commercialization or clear go-to-market paths. Sometimes they're past some sort of singular moment like Oculus and VR, Cruise and AVs or things like that. Typically the way you can kind of think about a lot of these areas is that they start as verticals, and when something is a vertical, it is... A vertical technology, rather. It is early, and when it becomes a more penetrated or more kind of horizontal technology, it is now in the next phase of commercialization. That's mobile, that's AI, I think that will be VR, AR, I think that will be crypto. Those are things that are verticals today, but they become platforms tomorrow.

“Typically the way you can kind of think about a lot of these areas is that they start as vertical technologies and when it becomes a more penetrated or horizontal technology, it is now in the next phase of commercialization. That's mobile, that's AI, I think that will be VR, AR, crypto. Those are verticals today, but they become platforms tomorrow.”

That's one, which is we get to things really early that we find weird and interesting and then we try and learn about them. We have a really strong view that... There's a famous saying like, "The way to learn about things is study them when they're coming apart." We think by studying things as they break down, and we've seen that in AI, we've seen that in crypto twice now, we've seen that in VR, we think that's where you really learn a lot to have kind of a long-term understanding of where value can be captured and accrued over various times in these phases of these technologies. Eventually they reach late cycle and hopefully you've built a defensible brand network effect in that area over decades, but I think for us it's about getting that early and exploiting it over many fund cycles.

The second framing is the type of risk in which you are underwriting at the earliest stage. We're first money in usually to founders, and that means you're doing things that have never been done before is one way to frame it, and that never been done before can be on a science risk side or an engineering risk side. Science risk would be things in bio or healthcare, engineering risk could be both bio, healthcare, AI/ML, robotics, a bunch of other areas as well. That's kind of our definition of the categories and the things that we like.

Your second question was around founders and founder types. I think, again, each of these types of businesses actually necessitate different types of founders where if you are not going to be going to market with customers for a long period of time, like bio companies for example, you maybe have a different profile, maybe you're super high attention to detail, very high-risk tolerance, very high velocity of learning, but not great at outwardly selling or narrative or building your storytelling in the same way. I think that could be one version of a trait. I'd say overall the version is super ambitious, very attention to detail oriented, fairly technical and always an understanding, not necessarily an ability, but always an understanding of what is the bleeding edge of their category, and the ability to as the time between academia and kind of operationalizing technologies compresses more and more, which is something we believe in deeply, that ability to know what's happening and bring it into a company framing I think is really, really important for almost every category we invest in.

MM: Mm-hmm. Yeah. I feel like that's the rarest skill, knowing how to turn it into a company. Do you think that's true?

MD: Yeah. I think it is, but I think my framing and my thinking on this sometimes has evolved based on some categories and founders I've worked with where I generally overbias towards, yes, the founders that can navigate the idea maze in an incredibly thoughtful way and have a very well-trodden path of having a hypothesis, trying to prove that hypothesis correct or not, and then moving on and working through that very quickly.

There's another framing that Cristóbal at Runway talks a lot about, which is... I'm blanking on the name of the actual framework, but the idea is that the way to get the right answer is to have the maximum amount of ideas possible and just put them into the world as quickly as possible and that allows you to actually then find the right answer, not being incredibly slow-moving and thoughtful. I think to his credit and to their team's credit, in AI they've recognized that for a period of time and especially in this moment of time they have. That's a framework that is a little novel to me and a little terrifying to me, but I think that those are very different skillsets of founders of velocity of ideas and being willing to be wrong quickly versus being super methodical and taking tons of data in and forming a view, which is much more where I bias towards, but it's not clear that's actually always the dominant approach.

MM: Yeah. Comes back to founder product market fit. Yeah. Interesting.

MD: Yeah.

MM: Okay. My next question for you, I'm curious what is your process for developing theses for Compound? Maybe mention a few of them and then we can dig deep.

MD: Yeah. We spend way more time reading and thinking and talking about these things internally than anyone else I know. That also means we spend way less time in meetings and attending kind of networking events than a lot of people we know. I don't say that as a like, "We're cool and other people aren't." It's literally like that's just how we prioritize our time. A lot of people do ask, they're like, "Well, how do you guys go about this? How do you read all these things, blah, blah, blah?" It's literally just hard work and time. A lot of that is because we always are reading research. We always are reading weird kind of visions of the future from engineers, researchers, operators, whatever in these R&D groups.

“We spend way more time reading and thinking and talking about these things internally than anyone else I know. That also means we spend way less time in meetings and attending networking events than a lot of people we know.”

We spend... Every few weeks, we have a session called Compound Learning Together where we sit as a team, we bring two to three what I would call 50 to 75% baked ideas with a bunch of research. We send this the night before. We talk through these ideas, and then that kind of creates a flywheel of us figuring out what we need to learn more and to dive deeper on. We do that pretty consistently. Sometimes we invite people from the outside as well. Then I just have an insane apparatus around reading where I have a bunch of things that I'm topic modeling and then having flow into an RSS feed. Really, it's just this perpetual cycle of read, talk, listen, write, learn, and that just kind of continuing to go. That's the process, but a lot of it is like, "How do we get to a point where we have a formed view that allows us to move quickly and talk at a level with a founder that maybe your average investors, a more generalist, kind of wouldn't be able to? How do we make sure we set up our schedules and our time so that we can do that and not go entirely crazy?"

“Every few weeks, we have a session called Compound Learning Together where we bring two to three 50 to 75% baked ideas with a bunch of research. We send this the night before. We talk through these ideas, and then that creates a flywheel of us figuring out what we need to dive deeper on. “

MM: Yeah.

MD: So there's that, and then that kind of feeds forward into like, "Okay, what are versions of the future we believe in, which is what we view our portfolio as a collection of?" That's sometimes also driven by external worldviews. Right now we're spending a bunch of time on energy, as a lot of people are, but more on self-sovereignty and decentralized energy grids as an area. That also is kind of related to another area of local compute and personal cloud computing. I think both of these are formed under a premise of a lack of trust at scale perhaps and more of a desire to have always-on computational systems.

In the energy side, we've done a lot of investing in crypto over the years and generally crypto is at odds with centralized entities. Energy grids is maybe the only one in history I can think of thus far that is net beneficial for the centralized players in the sense that we have very clear understanding that energy infrastructure is not going to keep up with demand in the near term and there has to be something that cracks within that. We've looked at a bunch of ways in which one could kind of invest against this, have value accrue within different types of companies. We also think technological shifts across a bunch of these areas are happening. Those are a few of the areas, and there's a bunch of others like robotics and kind of AI as well that we can talk through.

MM: Neat. Cool. Okay. Starting with decentralized energy grids, I'm curious to hear where you look for opportunities that would make sense for an investment from Compound, specifically venture-backable. I'm curious how you think about that.

MD: Yeah. I think there's steps. The first order step is something like Tesla Powerwall or some of these companies doing other types of engineering through heat from the Earth's core. I'm blanking on some of the names of those companies, but how do you just get sovereign energy broadly, which is fully independent energy? That's a first order thing. It's pretty centralized still, but I think over time what you're going to start to see is, okay, there's financing issues. We backed a protocol on the crypto side that is still stealth that's focusing on bringing renewable energy financing at a certain scale of 5 to 20 kilowatt and sometimes bigger and smaller on chain to enable better liquidity for these assets. That's one where there's a bunch of people who would love to build more renewable energy infrastructure but just don't have the capital and there isn't formed institutionalization of that. If you can bring capital, then that starts some flywheel spinning.

Then I think you have secondarily you'll then have a bunch of technologies that can sit on top of ways in which you securitize, which is what this company is also doing, tokenize the cash flows and build these things into a true alternative scaled asset. That creates a new incentive. Then you'll have broader understanding of what we think is groups of people that don't want to be tied to basically under the thumb of a monopolistic energy and/or utility provider across a bunch of different countries. Theoretically, which this is a very non-consensus, but you could have theoretically those entities themselves, as we talked about, also not wanting to deal with the infrastructure investment and the supporting of a large number of groups of people. You'll have different pockets of ways in which that will manifest, but we think that that generally will point into a broader view of people will want to have the ability to be somewhat self-sufficient across a variety of areas in their homes and/or in pockets of homes in a similar way that communes have operated in certain years. Obviously different but similar.

MM: Yeah. Yeah, that makes a lot of sense. It also leads to the second point you mentioned about local compute and personal cloud computing. I'm curious in that case, kind of a similar theme, what do you think it would actually take for something like that to go mainstream and be desired by the average person?

MD: Yeah. The realistic answer is some really terrible event, and that's the first-order thing that creates lack of trust at scale, and lack of trust is what will lead to more people wanting to have local compute. The second maybe more optimistic version would be a breakthrough in performance driven by whether it's constant retraining of models or something that is economically not possible. One of the things we believe that's really compelling is if you look at housing, there's a bunch of costs built into a home. Today if you wanted to run a fairly large language model or multimodal model generally, you would probably need about $24,000 of compute about, and that's going down pretty materially. But if you bake that into a home purchase and you run a cost curve, it's actually not that crazy to have a compute stack in your home in a similar way that you have a bunch of other core utilities that make your home run, whether that's heating with a boiler room and things like that.

That then opens up a bunch of ideas of like, okay, you can have personal models that consistently retrain, you can have privacy that sits in data that sits in your home versus not, you can have a bunch of systems that need to be managed but without the ability to be shut off. Again, if you have power that can't be shut off maybe then you can have compute that can't be shut off. Then you'll have probably some continual window that shifts across a bunch of different countries on how they view the rights of their citizens. An example in the US would be we have these insane states that believe women shouldn't be able to get abortions and/or they want to impact how people make that decision. You can imagine in a world in which you have a constant on biology monitoring system in your home that is running insights on a bunch of things about you, you might not want that beamed up to the cloud and run on compute somewhere else that could be potentially subpoenaed or taken. You might want that data run locally that you can control who go in and out of it, especially in a world in which possibly there's two to three major AI providers that do that.

We think that there will probably be more and more things that people will want to, either from a lack of trust side or from a performance side, will want to kind of have done locally. Then the last is there could also be some short-term pressure from an ESG perspective on some of the large compute centers and cloud compute centers, but that's something that's more of a short-term issue.

MM: Mm-hmm. How do you go about trying to find founders that are working on this problem?

MD: I just chaotically tweet a lot.

MM: That's good.

MD: Writing, tweeting, asking people like you.

MM: Bat signals.

MD: Yeah. When I go places, this is stuff I'm thinking about. I think in general, all of our online presences are like Rorschach tests for a bunch of people to figure out if they align with you or not and think it's interesting, and we just try and talk to as many people as possible. I've yet to find a way that is more scalable and higher ROI than writing, and so that's the main approach but also talking to the people doing some of the academic research. The thing you realize is not a lot of people care about a lot of the fringes of academia, if you might even want to call it that. These people are usually very willing to talk to you about and love the fact that you're interested in something they've spent years thinking about, but it's totally unscalable. There's no good system for it and we're just banging our heads against the wall until we can find people.

“In general, all of our online presences are Rorschach tests for a bunch of people to figure out if they align with us or not, and we just try to talk to as many people as possible.”

MM: Luckily, that's kind of the name of the game. Yeah. Moving on, I'm curious to hear more about how you think about robotics over the years and what you think is next in that category.

MD: Yeah. We think... Robotics I would say is one of those things that everyone has been promising for years and it's never really worked, and it's also been really misunderstood by a bunch of different types of investors. If you were to look at robotics in the past 10 years, I would say it's largely been a mechanical engineering problem and there's been a bunch of people who wanted it to be an AI problem. What that means is you have to set up systems that are not super intelligent and dynamic but can do things very precisely over and over again, and maybe they can have some simplistic things like computer vision but there isn't material intelligence. There was a wave of companies that tried to do this and largely haven't worked out.

I think what we've seen now is we're at a clear turning point. Our view is we are in... If 2016 was the early kind of transformer days, I think we are there in robotics with a lot of the stuff we're seeing from large language models, a lot of the datasets we've had in a similar way that image recognition had ImageNet. There now are these big datasets being opened for more complex robotic understanding of the world. I think what we're learning is these large multimodal language models do have some form of world model, and we've seen this through some of the work where our portfolio company Wayve has been publishing on being able to say like, "Hey, why did you stop at this light?" It's not just like, "Because I've seen that data a million times." They can reason and understand a bunch of things about the world. I think we are in the phase of it is clear robots are going to be very intelligent and work very well over the next decade plus.

I think what that then means, which is a really hard part to be at, is you have to then think about really a unique and beautiful products. For the first time ever, robotics is as much about technology as it is about product, which is really exciting but, as we do more and more work talking to these people, really terrifying because those people do not talk to each other at all, no one. There is such little overlap. I think a lot of it comes down to how do you ideate around where these things should be, what are the use cases that make sense, and in a world in which it's not all just humanoid robots, how do you build really unique experiences that create tons of value and also maybe are just first of a kind? That's really hard for us to do because we're creative, but we're not that creative.

MM: Yeah. Absolutely. It seems like it'll probably start with niche industries, very specific use cases that you probably would never have even heard of.

MD: Yeah. I think... There's a company called Matician, which we're not investors in but I'm fascinated by, and they're a great example of... Their first product is a autonomous vacuum robot, and it's the obvious thing. Everyone's seen that. That's the only robot that people actively buy today. Their whole thing was like if you apply a new layer of intelligence and understanding, you can do things like point at something on the ground and be like, "Hey, clean up that trash over there." That's a beautiful UI/UX. That's something that is so nuanced and so creative from a product perspective that I think that we just need more and more of those types of conversations happening. It's kind of like the Disney Imagineering vibes of these people that are starting first from a delightful experience lens and then working backwards into what that means and how it looks and how technology plays a role in that. I guess there's the famous Steve Jobs thing also of when someone interrupts him when he's talking about the Mac of saying, "How do the technologies work?" And he basically says he doesn't think about technology that way. I think we need more of that in robotics. Yeah, it's inevitable in my framing and it's just is it three years, five years or seven years? We'll see.

MM: Yeah. It feels like a lot of the paradigms of how we interact with robots, so it's the part that needs to be innovated on. We just don't really have them established yet.

MD: Yeah. I mean, it's all driven by... All of our robotic understanding is driven by science fiction and media.

MM: I was just going to say, yeah, it's like all movies, which is not usually the best.

MD: Yeah.

MM: Some are really cool, but-

MD: It's not.

MM: Yeah.

MD: But it does... I do think what we're going to start to see is more of the... As more paradigms from software-driven AI allow us to be a little bit more creative and think about new types of products that should exist that haven't before, that probably will feed forward a little bit into robotics. I think the difficulty is when you're constrained by the real world and physics, it becomes really hard and your iteration cycles are much slower. But I do think there's going to be a ton of people that have built a bunch of fun digital products in AI and kind of hit a wall of saying, "I've built a bunch of features, but I haven't been able to build a company." The way you can build a really interesting company is you have a physical moat by being great industrial designers as well and all these other things. That's really-

MM: Yeah. Owning your hardware. Yeah.

MD: Yeah. That's a really interesting world to live in. I do think right now it's like the hardware narrative is a little too artistic and not actually venture scale, but we'll get there.

MM: Yeah. Yeah. What ideas do you think that we're still not ready for in robotics or culture-wise?

MD: Ooh. Yeah. I mean, the culture one is always the sex robots and things like that. People love talking about that. I'm like, "Whatever. Sure." Honestly, I think it's just going to end up being... I think there's... The way I would answer that, which isn't a good answer, is it's more about the brain damage that exists within the robotics community of never do in-home robots, agricultural robots only lose money, all these types of things-

MM: Mm-hmm. Interesting.

MD: ... that I think those are the limiting factors more of how do people break out of the modalities either being a six degree of freedom robotic arm or a humanoid and nothing in the middle. I think like that, and then the others are very sensitive but fully automated things. There's a few people working on surgical robots that are not remote controlling the robot, it's entirely autonomous, or childcare robots is a pretty interesting one where it's like of all the things you don't want to be the first user of, putting your child in front of a robot is probably number one. But if the main limiting factor on people over the next decade or two is labor and a need to make more money and likely spend less time with their families for better or for worse, likely for worse, you can imagine a world in which these robotic systems are going to need to push the limits on a bunch of stuff that humans do from an emotional standpoint as well because our time is just going to be more constrained. But again, I'm mostly just trying to spend time with really interesting creative people because this is one of those areas where I definitely don't feel like I have deep conviction outside of simple enterprise use cases where robotic companies could exist.

MM: We just need all the kids to get really into robotics-

MD: It's true.

MM: ... and then come up a new wave of thinking it's the coolest thing to work on.

MD: Honestly, a realtime robotics simulator in Roblox, put that in and-

MM: Yeah. That would do the trick, honestly.

MD: ... how to be physics dependent and you'll be there. Yeah. I think someone will figure something like that out. Yeah.

MM: Good idea. Yeah, that's so cool. You mentioned AI. I'm curious to hear briefly how your and Compound's thinking has evolved on the subject and sector over the years because I know you've been focused on this for a while.

MD: Yeah. I think... There's a framing of all emerging technologies that we have which is that emerging technologies eventually reach a point where there's a net human and/or talent retention and it goes above 100%, right?

MM: Mm-hmm.

MD: So as people leave an industry, more and more people and waves come in to replace them. I think once you see that, that's a clear sign actually ahead of technological breakthroughs of, okay, there's something here. It's kind of like the Chris Dixon framework of studying what smart people are doing on the weekends, but I think it's a little bit deeper of an understanding of these ecosystems. I think if you look at AI, basically once we got the GPU and AlexNet in 2014 and once we got ImageNet being dominated and solved and object recognition being solved, we kind of reached that point of there's a consensus view that AI in some form or machine learning then would be effective and narrowly better than humans.

That created a floodgate of capital and talent that was going to persist, and the talent moved across certain areas. A lot of people in autonomous vehicles churned out because they were like, "I've been working on this for a decade and nothing is changing and I can't do this anymore." But it all stayed around that kind of AI vertical and computer vision and deep learning. I think for us, a lot of it... The evolution kind of moved from understanding that new AI-first products would be created that think about the paradigm of the UI and UX and how that changes with AI. I think Runway is an early example of that where they kind of looked at the bar of everything in Adobe on the side and they were like, "This is insane. There's all these little tabs and tools and that's not how the world should work. You put a text box and things change quite a bit." All the way to a bunch of other companies in the spaces that basically were built around that primitive, and it's a very simple... It's mind and framing.

I think the other thing that we realized early on was the best algorithm is not going to be the thing that wins. I think we've forgotten that. Not we, but collectively the industry has kind of forgotten that over the past few years as the companies with incredible algorithms have risen, namely like Anthropic and OpenAI, but I think that now it's about, okay, how do you think about perpetual value accrual and really this framing that I think a lot about in crypto, weirdly. Crypto teaching AI things is not where I thought I would end up, which is you... Because you're building open source software in crypto and the commoditization curve is effectively instant in a lot of these areas, you have to have an execution ability that is persistent for many years as you're building some form of moats and as the other people who are trying to compete against you in these death by a thousand cut ways die, basically.

I think what that means today in the AI world is it went from "what do you believe that no one else does" to "what can you believe and consistently ship and run this marathon as if it is a sprint for the next few years as capital just flushes its way through the system". I think our framing has kind of shifted in how we think about teams even from before it was like Alex Kendall at Wayve, this wunderkind PhD from the University of Cambridge who's one of the most brilliant people in the world and solved a bunch of these problems around segmentation to today can be really talented product people that understand the bleeding edge of AI but are never going to be the researchers to implement it. They can build a really interesting product that just continues to sprint across as other people do a lot of hard work for them.

“What that means today in the AI world is it went from ‘what do you believe that no one else does’ to ‘what can you believe and consistently ship and run this marathon as if it is a sprint for the next few years as capital flushes its way through the system’”

That's a very simplistic view, but I think more and more teams are like that. Runway was kind of weird because it was an incredible product team but also really talented on the AI side, but I think we are overestimating how legible credentials are in AI and what it actually means to be a talented AI builder. I think the fact that people lean on pedigree so much in this space is probably very wrong and is very much something that should be early commercialization cycle behavior, and if we are in inning three instead of inning one, it's likely a false signal.

MM: Mm-hmm. That's super fascinating. So you look more for really strong product people, basically.

MD: I think it's both, right?

MM: Okay.

MD: You can have a really nuanced view of... We have a company in our portfolio called Orbital Materials and they're a spin-out from DeepMind, and in their case they're the world leaders in foundation models for chemistry. They have a lab and they have a bunch of these really hard go-to-market moats and technology and that's a unique company, but on the software side I do think a lot of it is like how do you have a unique view of what AI can create from a UI/UX and product perspective and how do you know how you can sprint against probably some form of commoditization curve and death by a thousand cuts for the next three years as you build distribution moats, talent flywheels, brand moats, and a bunch of other things?

I think we're getting to the point of brand moats mattering more and more in AI because the consumer and user, whether that's enterprise or consumer, is getting a little tired of downloading the 50th new AI tool and switching and trying it out where nine months ago we were all like, "This is awesome. I'm doing this. I'll download every AI thing. I'm ready. Any image generation, any tech, whatever." Now I think people are kind of like, "I have my things. I like them." Midjourney is incredible, and you're going to have to do some really amazing stuff to get me to ever get off of Midjourney image generation. DALL-E 3 might be that, I don't know, Imagine might be that, but those brand moats are starting to manifest and that's pretty interesting when you think about what it then means to be a world-class AI company.

MM: Right. It reminds me of what happened to note-taking tools.

MD: Yeah. Yeah. Eventually... Note-taking tools, yeah, eventually you just become this standard and you then have people who try and do niche adjacencies.

MM: There's something for that, but it's just not going to be huge. Yeah.

MD: Yeah.

MM: Interesting. I'm super curious, what do you want Compound to become? What is your long-term vision?

MD: I think the thing that destroys all venture funds and maybe people in venture is scope creep. I think that that is the... You can see that for, I don't know, the past decade plus. So honestly, my answer is what we do at Compound is research-centric, thesis-driven investing. That's our tagline, that's how we talk about it. I think we want to be world-class at that. We want to be world-class at partnering with founders as early as possible and we want to always understand where... And have very defined viewpoints on where we think the world is going and deploy capital against those views with incredible people.

I have very little desire to meaningfully scale the fund size or try and be this multi-stage institution. I want to prove that we're really great at what we do and in a specific type of company, a specific type of founder, with a specific approach. I think to prove you're really great... I think we're doing okay right now, and I think you have to be pretty good for multiple funds. We're on that journey now. It's a pretty simple answer, but I don't want to scope creep into doing other things despite at times in the past few years, you look up and it's like 2021 and you wonder if you're the idiot and everyone else that you thought was dumb is smart. Then you look up in 2023 and you're like, "Maybe I am a silly idiot, but they were idiots too." It becomes like... You just have to be... Venture, there's no feedback loops. You have to very much trust the approach and the inputs at all times. I think we feel really good about our inputs, and we'll see if those outputs pay off for our founders and our investors.

MM: That's a great answer. It's just such a long-term game. Curious to hear more about your philosophy on writing. When do you know it's ready to share? In what form? How have you thought about it?

MD: Yeah. There's a principle called Cunningham's Law, which is the best way to get the right answer on the internet is not to ask a question, it's to post the wrong answer. That is-

MM: Extremely true. Yeah.

MD:... extremely true. Some of it is that, which is like, "I have done all I can and I want to now put this in the world and have people tell me I'm an idiot, and that will make the thought process even better." There is one which is, "I have a view on how something could change or something that's interesting, and I'm starting to hear more people talk about it. I really want to make sure that my view is early and timestamped and there and can be scrutinized." I think some of it is, "I don't see anyone else talking about this thing and I just think we need to." That's another version. Sometimes it's just like, "I am tired of researching something. I don't feel that strongly that my view's great, but it's good enough that from a VC lens, the bar is so unbelievably low I can just fire it out there and hope someone thinks it's interesting."

"‘I have done all I can and I want to now put this in the world and have people tell me I'm an idiot, and that will make the thought process even better.’”

But I think a lot of it is... Time and time again, I just come to realize, especially in venture, there are so many styles and the style of investing we do is both incredibly replicable in the sense of there isn't any... Our moat is how we approach the job. It's not some big tech stack, it's not some algorithm, it's whatever. Also, it's incredibly defensible because people in venture are just miserable at putting the right inputs into long-term oriented things and doing certain types of work and time management and these firms decay over time. Not by them doing anything wrong, it just happens. Our view is just the more we talk about things, the more we dive deep, and the more we can connect with founders, researchers, interesting people, we should try and do that.

We're trying to experiment now with more private centric sharing as well on top of our public stuff. We launched this thesis database, which was more public a year ago, where we are very prescriptive on company types, et cetera, but it's always evolving. But the main thing is we just want people to feel like we have done a good amount of work and thinking on our own, and that I think goes a really long way when you then want to talk to people because they can feel the genuine passion about and the work you've put into something versus pinging some person being like, "Hey, I'm digging into this AI. I'd love to steal 45 minutes of your time to hear how you think about it because you work at OpenAI." Those people are going to be like, "Great. You're the 10th person. Awesome."

MM: Yeah, 100%. I remember a framing that you mentioned, if you don't agree with someone's worldview or something expressing it that way like, "This is how you see the world. This is how I see the world. There's a discrepancy, and that's the reason that I'm not interested in pursuing it further." I think that's a really good way of putting it which you can only do if you've put in the work beforehand.

MD: Yeah. Yeah. I think also just this job is so... So many egomaniacs in venture and just approaching it with this idea that we easily could just be totally wrong. The reality is is the beauty of our structure as a firm is we need to be right to two times every four to five years, which is how long we invest each of our funds, and then we're going to be wrong 30 other times. It's pretty incredible. The thought process really should be just how do you maximize being deep and generative and low ego and high EQ? You might totally go down in flames, but maybe it'll work out. Who knows?

“The thought process should really be just; how do you maximize being deep and generative and low ego and high EQ? You might totally go down in flames, but maybe it'll work out. Who knows?”

MM: Totally. Yeah. Enough shots on goal. My last question, I'm curious to hear more about the inputs that you mentioned you feel good about and what are your favorite ones that you return to and challenge your thinking most or theses?

MD: I'd say the challenge thinking is the team, spending time with Shelby, David, Smac, a bunch of our venture partners, that... Being able to have people that are obsessive about the craft of investing in deep tech and talk about things. I can come with an idea on some deep plant biology thing and Shelby, who's a PhD in plant biology, can be like, "You're an idiot, but also this is an interesting idea." The culture of being able to do that is awesome. I think... So that's one. I'd say we... Again, I kind of mentioned I have a very tuned RSS feed. I'm obsessed with RSS as a concept. It totally died. I still use it all the time where I have a bunch of topics that get automatically brought in from a topic modeling funnel across a bunch of different sources, some of which I don't even know.

“I have a very tuned RSS feed… I still use it all the time where I have a bunch of topics that get automatically brought in from a topic modeling funnel across a bunch of different sources, some of which I don't even know.”

I spend a bunch of time on archive and social sciences research just to see how people are trying to understand the world and from a research and scientific view. Often that's technology, but sometimes it's not. Then there are other areas where people are just forever... Maybe they're a little crazy, maybe they're really deeply thoughtful, but stuff like the Effective Altruism Forum and LessWrong and these random subreddits of people who are just obsessed with thinking is really fun. It's a totally different part of your brain, but it's a level of rigor that we don't get much on tech Twitter, which I also love but it's totally different. Then weirdly I'm a daily active user of Tumblr. I have a very tuned Tumblr feed.

MM: It's great.

MD: I love that for all sorts of random stuff, but Feedly is probably the main thing, that's my RSS reader and everything funnels through that, and then just an insane amount of Twitter. But all those things then funnel into me being able to... I try and send, I don't know, 10 to 15 probably realistically cold emails a week to random people that I think have written something or researched something. Andy Weissman at USV is an incredible investor, very close friend, one of my favorite people in the world, and he, as many people know about him, he just cold emails everyone. He'll read a book and email the author and they'll respond sometimes or watch a movie and find his way to the person who made the movie and just send them a note. He sends super thoughtful, deep emails.

I'm trying to incorporate that more into my learning process because I do think that serendipity, especially when you're a little bit unknown and moderately early in your career, is... You have a right to be able to talk to people or rather people are willing to talk to you a little bit more than once you're more senior or more well-known or viewed as more successful. I think that decays very quickly, and that's what I tell all people early in their careers is people will talk to you just because you're young and early and it's a beautiful thing, and just push on that until they're tired of talking to you.

MM: Yeah. Such good advice. People always think that they lose the student card when they leave school, but they do not.

MD: Yeah. Yeah, exactly. It's insane.

MM: It sounds like you've built a serendipity machine. I really respect that. I think that's great.

MD: An introverted trying to... I don't know if... Yeah. Trying to engineer serendipity, which is not a real thing, but I think it's just trying to find people that you can connect with them on some feeling of how they think about the world and things you care about or whatever. Yeah, I think that's how we met. We just definitely have a view on the depth at which we care about things, which is an insane statement because that's so general, but you feel it so quickly and at times that's why I think places like SF and New York are so special is because you just have really high alignment on a depth of caring about things, and then you can go a layer deeper on what are the things you care about. But just that first order handshake we all make is pretty incredible because it just helps make any topic of conversation more well respected and digested, I guess.

“I think it's just trying to find people that you can connect with them on some feeling of how they think about the world and things you care about… We definitely have a view on the depth at which we care about things”

MM: Yeah. Is it sincerity, earnestness? I don't know what it is.

MD: Yeah. It's like-

MM: Something like that, yeah.

MD: It's like some form of insane optimism, some form of sincerity, some form of we all spend too much time on the internet.

MM: Yeah. Curiosity. 

MD: I haven't quite gotten what it is yet, but it's something.

MM: Lovely. Well, I think that's a great place to wrap up. This has been so lovely, Michael. Really enjoyed it. Thank you so much for coming on the podcast.

MD: Me too. Yeah, thanks for having me. This was great.

Subscribe for more episodes to come: Spotify, Apple, Google, Amazon, and Overcast.

My whole job for this first fund is to bet on promising people. One of the most frequent questions I get as someone surrounded by a lot of young talent is “What makes the founders of your generation different?” While I can offer plenty of high-level platitudes, I’ve found it’s more compelling to put you in our shoes. Picture this:

You grew up online: firstly, on technical forums alongside hobbyists and retired engineers discussing how to build robotic arms for small-scale manufacturing, and secondly, on Twitter. You were always an intensely curious kid with innate talents in math and science and when your life became complicated by your parent’s divorce in grade school, you made good friends with your computer. The forums taught you a lot — leading your rabbit holes to become large-scale projects. You begin a master project that people pay attention to — financially supporting your work, commending your drive, and telling you you’re special. A deep-rooted sense grows within you that you’re destined to do something great.

It was in high school when you discovered Silicon Valley. This was a time when Facebook was already starting to become boomer, Instagram was for girls, and Twitter was where all the interesting technical people spent their time pre-retirement. Twitter externalized the culture of Silicon Valley — its ambitions, ideals, and influences — into a readable daily sitcom complete with protagonists, antagonists, and subplots. You were entranced. You made friends and a name for yourself there through a mix of proactivity, earnest curiosity, and sharing good work that captured the zeitgeist of the time. But after subsuming most of your high school experience, your master project had started to feel sour. After much cajoling from friends who know you well, you finally called the project quits and hung up your tweeting hat your senior year. You’d learned how to play the game well enough to know when you were playing the wrong one.

You go to college in Texas to study electrical engineering. You can do everything, collecting all kinds of impressive short-term jobs for yourself during the summers using thoughtful emails and DMs. You experience your first tragedy and subsequent struggle, leading you to get briefly tangled in the mess that is mental health care today. Like many of your friends, you come away from this experience with yet another reason to feel like our institutions are lying to us (“Why are we told to focus on ourselves when the only thing that worked for me was focusing less on myself and more on the people around me?”). Unlike your friends though, you remain optimistic. Your wisdom and reasons to keep going are hard-won and rooted in faith, not fact. 

You gradually meet all of your heroes. You watch and analyze world-class people at work, taking detailed notes. You’re especially drawn to those who don’t seem to have sacrificed leading a happy life to do great work. You like SF but don’t like NYC. All around you, everything keeps changing — the technologies, where your globe-trotting friends live, what they’re working on. Startups no longer carry with them the sparkly all-encompassing ideology that they once did, and the ones that do frame it ironically. At the same time, one of your projects starts blowing up, bringing in real dollars. You’re briefly tempted to drop out, picking SF’s scene of big dreams over the village you spent all of college building for himself. “What are you learning in school anyway?” the scene murmurs. You think about it and realize you have an answer: you’re learning how to live. You stay put, savoring the last months you have in the comfort of still being a kid.

This is where you stand now, with a whole army of friends on your side and endless options on the table. To name a few: found a company, go into research, or spend time in politics. You see your life as a series of projects and predict you’ll do everything on that list someday. Founding has always been your dream, but you’re discerning — the questions of what, with whom, and when need answers first. In the meantime, you continue building your own independent conviction. You know you’re just getting started.

***

This is what being a future founder feels like today. Unlike the founders of yesteryear (most notably during the 2010s when technology was more widely celebrated for its own sake within Silicon Valley and the industry was far smaller) I’ve noticed that the most promising founders taking their first shots on goal today are defined by:

1. Being prolific in many more areas than ever before by a young age (they think of their career in “eras” and see technology as merely one means by which they can make an impact)

2. Holding hard-won irrational beliefs from an early fall/formative experience (this is what makes them an outlier and gives them a unique POV)

3. Show signs of thinking for themself: abstaining from social media, practicing religion, going to and graduating college despite having other, more advanced professional opportunities available to them

I believe that good founders have been and always will be N’s of 1 — but what constitutes an outlier is dependent on where they stand in relation to all that came before them. While some founder qualities have been consistently beneficial to the formation of Silicon Valley (e.g. curiosity, proactivity, and grand ambitions) other indicators are still emergent that a person is one of a kind. Now that I have placed you in our shoes, I’ll turn it back to you. Who comes to mind?

Essay style inspo thanks to Michael Dempsey

Highlights:

• One commonality between all of the investors at Benchmark is that they’re extremely curious, truth-seeking, and able to quickly spin up on a given topic. Blake in particular has learned to lean into his innate curiosity about what’s happening in weird corners of the web as a way to differentiate himself as an investor.

• Building a unique brand for yourself (perhaps even a pseudonymous one!) makes you relatable and helps generate serendipity online — ideally done within a subculture of the web that contains people who share your interests and understand your intentions.

• Consumer products will increasingly take inspiration from games — especially the way games go about monetization and retention. Games are powerful in the way that they manipulate agency and often succeed by taking advantage of technological and cultural shifts.

MM: Hi everybody. Today I’m joined by Blake Robbins, a principal at Benchmark. Prior to Benchmark, Blake was an investor at Ludlow Ventures. He also co-hosts a podcast on the history of the video game industry called Gamecraft.

Our conversation covered Blake’s unique insights from studying the business of games, how curiosity drives his investing, and his thoughts on being a person online. I hope you enjoy.

MM: Blake, so happy to have you on the podcast.

BR: Oh, thank you for having me. I'm excited to be here.

MM: To kick us off, my first question for you, digging right in, is what would you say are the three big takeaways from your podcast series on gaming?

BR: That's a fun question. For maybe people who haven't listened, I did a podcast with my partner at Benchmark, Mitch Lasky, on gaming history overall and the world of business through a gaming lens. And for me, there are a couple major takeaways. One is, man, I grew up in a very golden period, probably similar to you, of games, but mainly as a player. And I never actually fully understood or appreciated what was going on behind the scenes. I think the other major takeaway for me is just how important business model shifts and distribution innovation was in gaming.

“I think the other major takeaway for me is just how important business model shifts and distribution innovation was in gaming.”

And a lot of people look at the art side of gaming, and that's a lot of what gets the love, for the creative side, but the business side is honestly, if not more important, equally important, to the creative side. And it actually shapes and impacts everything, which obviously sounds very obvious now, but when you look back at it through a real lens, wow, even the shift to free to play or why there was a shift to free to play and why do games get distributed on Steam? All these things is just really amazing.

And then I think the third major takeaway is just Mitch is a legend, and really getting the opportunity to sit down with Mitch and hear his perspective. There's probably two or three other people that went through the same career arc that Mitch did within gaming, and he has such a unique vantage point, and for me, it was just a real blessing and opportunity to just get that perspective and out there in the world. For me, I was having those conversations behind closed walls and we kept talking about we should have this conversation in public because someone will benefit from it, yeah.

MM: Yeah. That's amazing. How have you evolved your thinking since doing the podcast, do you think?

BR: It's funny. I spend a lot of time in games and thinking about games from an investor perspective, and for me, I always wanted to invest in games, but there was a part of me of like, "This is a hit-driven business. This so hard to invest in." All the standard tropes that people say about games. For me, my thinking has evolved and much more of there is real method or reasoning of why these games broke out or why certain companies succeed. And I think that just makes me a better investor, but also just a better thinker of the space. And almost every game I play now, I think through the lens of, "Why is that game number one on the charts?" Or, "Why did this game break through?" And for better or worse, just the analytical side of me now thinks through the lens of the podcast of, "Oh, okay, that's of course the shift that this is taking advantage of or why it's breaking through."

“And for better or worse, just the analytical side of me now thinks through the lens of the podcast of, ‘Oh, okay, that's of course the shift that this is taking advantage of or why it's breaking through.’”

MM: Has it trickled down into investing in other things too, like frameworks that you apply also?

BR: Yeah. Again, it sounds obvious in hindsight, but it's more that business model and distribution, or the innovation around those two things, is so important, not just in gaming, but in almost everything, and catching the wave or understanding how you're going to attack that. It's actually pretty shocking the number of companies you talk to when you push on one of those variables of like, "What are you actually doing to make sure people play your game or use your product?" A lot of people just assume if you build it, they will come and it's just not the reality. And a lot of this is really scrappy. How do you think about taking advantage of the wave that's happening behind you?

“How do you think about taking advantage of the wave that's happening behind you?”

MM: That's super interesting. Where do you and Mitch disagree?

BR: There's a few different places where Mitch and I disagree. I think the biggest is I'm still a pretty big believer in mobile. And I think Mitch is a believer in mobile, but I still think that there's investible opportunities on mobile. I think Mitch is a little bit more burnt out on the flywheel of how you have to spend a bunch of money to acquire users and whether that's sustainable or not. I still think that there are investible opportunities there and I think there's real opportunities. Mitch, I think is a little bit more like, "Nope, this is all just CAC all the way down." Like it's the same as direct to consumer type of CPG products.

I think there's another view which is I probably overweight the importance of streamers and content creators within the world of gaming. I think Mitch respects where those people are and their role within the ecosystem, but I still think that's really the biggest unlock within distribution.

MM: Yeah. Do you think that's going to increase over time, it's suddenly going to become more and more popular?

BR: I think so. My personal view is that over time most games are just going to partner up with the biggest creators, and you're starting to see a little bit of that happen. But you could totally imagine the biggest, I don't know, shooting game in the world, partnering with the best first person shooter streamer, and bringing them in. It's a way to hack community, but also marketing and then get that person to have some upside and have them be an ambassador. And I think that will for sure happen more and more over time, and they're just going to be more deeply integrated, at least for the hardcore type games and more of the core type games. But the other side of this market, I don't know, maybe not, but you also have Mr. Beast in and random mobile games right now, so that also happens.

“You could totally imagine the biggest shooting game in the world, partnering with the best first-person shooter streamer, and bringing them in. It's a way to hack community, but also marketing, and then get that person to have some upside and have them be an ambassador. “

MM: Where did those strategies start, the one of teaming up with the best content creator? Was it the last 10 years, last five years for YouTube?

BR: Yeah, it is probably the last decade. Really League of Legends and Minecraft were the two that benefited the most from it. You could take a very, I don't know, firm view of how games have broken out and you can be like, "Riot and League of Legends broke out because of Twitch and they sort of rose at the same exact time and they were very symbiotic." And then you could also say Minecraft and YouTube really were tied in together as those both really benefited from it, and Roblox is also probably in that same wave with YouTube. It's very strange to think about how those two actually... They all grew with each other and YouTube has greatly benefited from Minecraft, but Minecraft also greatly benefited from Youtube. And both Minecraft and League of Legends weren't necessarily super thoughtful of how they were approaching their creator ecosystem early on. It was much more of the games were great for that and Twitch was a great platform to stream League of Legends and so forth. And now it's become way more.

“YouTube has greatly benefited from Minecraft, but Minecraft also greatly benefited from Youtube. Both Minecraft and League of Legends weren't necessarily super thoughtful of how they were approaching their creator ecosystem early on. It was much more that the games were great for that — Twitch was a great platform to stream League of Legends and so forth.”

Probably the most calculated version of this that we saw was a game called Apex Legends from Electronic Arts. And for their launch, they actually did a massive pay every streamer on Twitch to play for a day. They just blanketed it. It was a very extreme approach, and every streamer who played games on Twitch went and switched to Apex for, I don't know, 48 hours, and it just created so much hype around the game. The game immediately became number one, all this stuff. It actually fizzled out and didn't do that great for the three months after, and then eventually it came back. But they definitely made an explosion on the scene. And I think they took the route of we aren't going to pay for billboards and do the standard TV marketing, we'll just put that budget towards directly to creators. I think that will continue to be a thing over time.

MM: Yeah. It's really meeting the people that they want to meet and will actually buy where they are.

BR: Yeah, it's like getting a trusted person... It's the same as buying radio ads or podcast ads where if you listen to that person all the time, you're just going to naturally have more affinity towards what they say, that they want to sell or buy.

MM: Yeah. It's interesting to see even early stage startups are using this strategy more and more. Synthesis, they employed a first grade or preschool teacher or something to be their ambassador, and it actually does seem to really work. It's like this is the trusted source. They're actually deferring to an expert and bringing them on board and having them tell the story for them.

BR: Yeah, I think that's right. I think a lot of this is marketing today is primarily driven by relatability, and the biggest streamers are just very relatable, not actually relatable maybe day to day, but they feel very relatable. And parasocial relationships are a very real thing, but within these ecosystems.

“I think a lot of marketing today is driven by relatability, and the biggest streamers feel very relatable — parasocial relationships are a very real thing.”

MM: It reminds me of the very good meme of the guy sitting next to a poster of some friends and they're just eating something and he's laughing and he's like, "How it feels to listen to a podcast."

BR: Yes. Yes.

MM: It's very real though.

BR: Yes, no, it is. It is. And I think podcasts in particular is you're basically just a fly on the wall, listening to a conversation. And it's part of why podcasts can be so powerful. You don't need a massive audience, but as long as people listen to them often, they'll think that they know you, Molly, and how you think about things, and that's really powerful. It's a way to scale your thoughts and hopefully this isn't too much work from a editing perspective for you.

MM: Not at all. Yeah, the thoughts can be much less polished and still be more relatable to, as opposed to writing, which I feel used to be the default.

BR: Yeah. Yeah, I think it is harder to have a distinct style in writing. The best are amazing at that, and it's very clear, but for, I don't know, call it the 99% of writers, it just seems like they're regurgitating other facts or just throwing random stuff out there. So I think podcast allows personality to shine through a little bit more clear.

MM: Yep, agreed. Going back to games, my last question for you, I'm just curious, at a high level, where do you see the world of gaming going in the next decade?

BR: Ooh.

MM: Big question.

BR: There's probably a few different thoughts, but my biggest belief within gaming is everything is a game. I think all of life is a game, which might be a really, I don't know, sad way to look at life. But a lot of how I've thought about things is I'll study so I can increase my ability to do better in the world type of thing, or I'll work hard so I can do better, and that translates into actual currencies and whatever. But I think there is leveling up in all of these different pieces. But what that actually translates to, what that means for gaming and business, is I think every consumer product over the next decade will really learn and take inspiration from games. I think games have figured out monetization and retention better than anyone else, at least on the consumer side. There's a lot of people that might be like, "Wow, it's because they're super predatory." And I actually just don't think that's the case. I think you look at something like Strava, and Strava has some real game mechanics within it and that's a net good.

“I think every consumer product over the next decade will really learn and take inspiration from games. I think games have figured out monetization and retention better than anyone else.”

And I think one of the main things that I believe around gaming is games manipulate agency, and that just creates some really powerful things. And that could be a weapon for bad, but in a lot of cases it can be really good. And you look at Duolingo and Duolingo is a game. That's not an actual learning platform today, but still people will go in every single day and take their lessons because it feels like a game. And I think that will just continue to shine through throughout all of consumer. I think within gaming specifically, my view is you're going to have way more of these massive multiplayer games and you're going to live in these worlds. I think games and social will blend a lot more clearly over the next decade in that games understand social better than social companies understand games.

“I think one of the main things that I believe around gaming is games manipulate agency, and that just creates some really powerful things.”

I think all of the execs at social companies are just like, "We know that games are a thing and it actually drives a large portion of our revenue, but we have no idea how to actually make a game or why people are sticking or downloading these games." And I think it's easier to understand the social side of this and that will happen over time. It's going to get very interesting when you have a game... The next major social network, in my opinion, will look closer to a game than the standard Facebook or Instagram.

MM: Interesting. I really like that thesis. Shifting more to thinking about investing and potentially where the investible opportunities are within that shift, my first question for you is actually more along the lines of just being an investor. And it's how do you think about the trade-off between being in a smaller fund with more opportunity to make decisions and to learn from everything that's going on versus being in a bigger fund and reaping the benefits of more of an apprenticeship model where you are closely paired with somebody?

BR: Yeah, so I've been doing venture for, I think, eight years, nine years, something like that at this point. And the first six and a half, seven years, I was at a fund called Ludlow, and that was a $50 million fund, seed fund. And very much we were writing, not a lot of checks, but we were writing a pretty high volume of checks and working with a wide variety of companies, very generalist, probably doing 30 companies per fund. I was there for about two and a half, three funds or something like that. So just a large number of investments. And that was very much like you're just run in to the fire and learn, and we were all learning as a team of three. We didn't know what we didn't know. And that's a really unique learning experience for me, and I wouldn't trade that for the world. I learned everything I know about venture through that lens.

What I think is I reached a point where I was seven years in or six and a half years in, and I knew the world that I was in. I knew a very narrow view of venture, of seed stage, complimentary style investing. And I talked with Benchmark briefly, and Benchmark was just like, "You should come and join us in a principal role." And we talked a lot of what that would look like. And for me, I got the conviction of, "Okay, I'll do this role because I want to learn. I want to learn a different style of investing." And I think there's only so many periods in your career where you can do that, where you can dip your toe into other places and be like, "Okay, I know this one, very narrow view. Let's see another narrow view of venture." And for me it was just such a compelling opportunity to be like, "Wow, these are people I truly respect and are truly amongst the best in the world at their craft." Getting the opportunity to learn from that seems stupid to turn down or to pass up.

And for me, that's how I evaluate it. I think I'm almost two years into that today, and I would say it's one of the best decisions I've ever made just from learning from this group, is they're really special. And I've learned so much, so much that I didn't even think I needed to learn or thought I would learn, all these random things. Mainly soft skills more than anything else. It's hard to actually put into words, the tangible learnings, but for me it's just been incredible. And I think nothing will replace just making investments.

And so when I was evaluating this, I remember talking to a mentor and they're like, "The only thing that matters as an investor is making investments and finding great companies and working with great founders, and I think for the position you're in, keep doing it. You're learning a lot and you're going to learn a lot. But if you ever do reach a point of like, "Wow, maybe my grats have stagnated, or my learnings have stagnated." I think there's always other routes to pursue that." But yeah, that's at least how I've thought about it.

MM: I like that a lot. It reminds me of the explore versus exploit model, too. You explore, you do a lot of investments, then you refine it down and really learn the craft from the very best. I am curious, what are some of the key learnings that you have gleaned from being around Benchmark people and seeing how they think and make decisions?

BR: I think it's just more of the clarity of thought that everyone has at Benchmark is just so unique and rare in that I can sit in at a pitch meeting with them and we'll be sitting there and they'll ask questions. I'll be like, "That's an amazing question. I would've never even thought to ask that question."

We might reach the same conclusion of whether we want to invest in this founder or not, but it usually is just the way that they get there is so systematic or more clear and concise in how they think about these things. That's a really hard thing to actually take away tangibly other than just watching and continuing to learn and observe where they might push.

I think that Benchmark for me is just an absolute obsession with working with founders. That is not scalable in any way. That's why the fund does a small number of investments, but we really work with our companies.

The discipline and obsession with that craft, I just have never seen anywhere else. It's part of what attracted me to join here so much is we really take it seriously, so much so that we believe that we can't just simply increase fund size. That makes us better at our job.

Instead, it's like we need to make a small number of investments and take our board seats very, very seriously, and the role of working with founders very seriously.

For me, it's just been amazing to watch. I've learned so much in how to approach even that and how you manage the relationship between a board member and a founder and make sure that you get what's best for everyone and how you make sure that the company actually succeeds.

MM: Yeah. Great answer. Are there any throughline qualities to all the investors at Benchmark that you think makes them a Benchmark-like investor?

BR: Just an insane amount of curiosity and just actual truth-seeking in a way that they'll go down rabbit holes, or you'll mention something, and they get up to speed in 24 hours because they just spent the past 24 hours just reading all about it and talking to every single person they can.

“[The throughline quality to Benchmark investors is] just an insane amount of curiosity and truth-seeking in a way that they'll go down rabbit holes, or you'll mention something, and they get up to speed in 24 hours because they just spent the past 24 hours just reading all about it and talking to every single person they can.”

I think it's more of there's no ego when it comes to should they know or shouldn't ... How could they learn? I've seen them approach new topics where they're not experts, but they get up to speed so quickly because they're so curious and they want to learn, and they talk to the right people. I think that's just rare.

To maintain that even at the highest level is just really, really rare. They actually are just always trying to meet amazing founders, but also just find the rabbit holes to go down and actually learn.

For me, it's part of why I love this role so much is getting to watch that and getting to do that myself.

MM: Yeah, really interesting. If you could go back in time, what would you tell your 23 to 25-year-old, whichever one you pick, self in regard to career advice and what you wish you'd known?

BR: I think it's more just slow down. I know that sounds strange, but it's a lot of ... This is a long game, and really takes the relationships and friendships. Just enjoy the journey more than anything else.

I think it is really easy when you're 23 and you're in venture to get caught up in the world that you're in and feel like you're in a race or you're comparing yourself to others. Whatever it might be.

For me, it would've just ... Invest more in myself and spend more time just thinking and breathing. Investing in the relationships that I really did want to nurture. I'd probably still say that to my 23-year-old self. I'm 29. I'd still say that to my 29-year-old self today, but I suspect that will forever be my advice to my younger self.

It's just like, man, you should have just slowed down and enjoyed the journey more. I think it's try and just find really amazing people, and your filter of who you spend time with is just really important. Make sure that you're just being really thoughtful about that and why you're polarized or drawn to that person.

MM: Yeah, I think always analyzing, yeah, what is it, these qualities, that keep popping up that makes me drawn to somebody? I feel like that's a very worthwhile inquiry to figure out and take notes on.

BR: Yeah.

MM: Something that's really surprised me about venture is how oftentimes it's learning about unconventional weird things that are not about the macro or venture or something. Anything that will make your perspective interesting and unique and your brain bloom in fascinating ways was actually probably worthwhile for your differentiated edge and making an interesting decision that maybe other people would pass up.

BR: Yes. Yeah, I think that's sort of the thing I love most about venture is there's no right way to do this role. In a lot of ways it might be like you could make an argument that six months of the year you should just be reading and writing and taking one meeting a week. If you told me that was the way that the best investor in the world did it, I actually wouldn't be that shocked. Then there's the other side of some people who want to take a million pitches a week. That's another way to do it.

“You could make an argument that six months of the year you should just be reading and writing and taking one meeting a week. If you told me that was the way that the best investor in the world did it, I actually wouldn't be that shocked. Then there's the other side of some people want to take a million pitches a week.”

I think a lot of this is very individual and trying to get comfort in the way that you think is the best way to perform and best way to work with founders.

For me, a lot of it ... My reflection has always just been the best way for me to use my time is actually really sitting and breathing and going down rabbit holes and following my curiosity.

I think that more of that would've always been good. My 23-year-old self is I had infinite time to do that and I should have been doing that even more instead of taking pointless calls, or whatever it might be.

MM: Yeah. What are some examples of rabbit holes that you've gone down that have led to decisions or investments if you care to share?

BR: It's such a difficult question to answer because, similar to what you were saying, the rabbit holes often will look like they're not related at all.

Or it will seem like it might even be a waste of time, but it can be like, oh, wow, I went down this rabbit hole, I'd learned about this, and that connects to this completely other thing that I would not ... No one rational would be like, "That's connected," but the way my brain works it's like, "Oh, that sort of reminds me of this weird SaaS company. I should go and message them again and see how they're doing."

I think that's more often how it would work for me, where it's just going and exploring and spending time in these weird places, then being like "Oh, wow, okay, I should actually reach out to that company or "I wonder how that company's doing" or "Is there a company in this space" is much more how it works, but it's hard for me to pinpoint exactly the ...

Every investment or every company that I've ever worked with, the journey of how I've ended up to conviction and making that investment is so serendipitous.

Every one of them has their own journey and story. That's also one of the more terrifying but exciting parts of this role is to create serendipity. It's hard to scale that in a lot of ways, but it's also impossible to replicate of how you found some company.

“A lot of what you do it is try to create serendipity.”

It's very strange often. It's not super scalable.

MM: Completely. It reminds me of just putting coins in a slot machine, hoping that some of them will work.

BR: Yeah.

MM: And they often do, but it'll be years later.

BR: Yeah, I think it's a lot of you need to ... What you're doing with this podcast, for example, is for me it's like you're just trying to plant seeds in a bunch of different places and make sure that people think of you.

MM: Yeah, yeah. Exactly.

BR: Or it's like, "Oh, Blake has unique thoughts on gaming. I should send that to him." Whatever that might be, or thinks about this or Molly thinks about this. That's a lot of how I think about at least my public persona is you need to make sure that people understand who you are or why they should even think of you.

MM: Yeah. That reminds me too in shifting more towards how you go about being a person online, which I find very inspirational and really commendable. What is your philosophy on both writing and sharing thoughts online? How has that evolved over time?

BR: It's funny. I was born and raised in Michigan and primarily do this job from Michigan. What that means is how do you actually build relationships or stay top of mind? For me, it was very early on I realized I need to use Twitter. I was like, "Otherwise, no one's ever going to know I exist at all." I just became super active on Twitter early on.

When I look back at my early tweets, I was shameless. I would tweet at insert big name venture capitalists or big name CEO, and I'd be like, "Hey," this is public, I'd be like, "Hey, I'd love to chat. Would you be up for it?" People would jump in and be like, "You should talk with Blake." I'm like, "Oh my gosh, this is crazy that I used to do this."

MM: It works.

BR: Yeah. I mean, look, I was shameless at the time.

MM: Yeah.

BR: I cringe a little bit now, but I joke because it actually worked.

MM: Yep.

BR: For me, Twitter is the town square of venture in tech. I sort of think of it as you need to be active there to make sure people just understand that you're still alive and talking and spending time thinking about things. Otherwise, it's really easy to just be forgotten about.

For me, a lot of it early on was just me actually just sharing my thoughts, just completely raw of what's going on in the world. I would jump into a lot of conversations that I had no reason to be jumping into.

My advice to anyone who ever wants to actually build a brand and an audience on Twitter is just try and add value to a conversation if you can, even if you're not involved in that conversation. That's what I obsessed over when I was in college. I used to just jump into random people's conversations and be like, "Have you seen this one? Have you heard of this? Have you read this?" It created so many interesting conversations over time.

Then as I've ended up in venture, I sort of view it as my public persona has gone through periods of my curiosity, so I've gone deep on creators, I've gone deep on eSports, I've gone deep on gaming. I've gone deep on probably five or six other areas. Depending on when people sort of followed me or started the journey of following me, they might have a very different skewed perspective of where I spend time.

The reality is I'm actually pretty generalist and spend time in a lot of different places, but what I try and do is I try and share my learnings or thoughts or weird crevices of the internet that I find interesting.

Thankfully that's resonated with people, but never explicitly with the goal of actually building an audience. Actually, my unpopular opinion is I think you should cap your following, your followers, at like 15,000.

MM: I think I agree with that, yeah.

BR: I think once you get past a certain threshold ... I think if you take the town square analogy to the extreme, it's like everyone's just walking up to a microphone in the town square. At some point when you get too big of an audience, it starts getting picked up in towns very far over. You're like, "This wasn't intended for you."

“I think if you take the town square analogy to the extreme, it's like everyone's just walking up to a microphone in the town square. At some point when you get too big of an audience, it starts getting picked up in towns very far over. You're like, ‘This wasn't intended for you.’“

MM: We're not even speaking the same language.

BR: Yeah. Yeah, exactly. This was not meant for you. This is meant for the people that know me and understand that I would not say this in a completely out-of-context way.

That can be frustrating and annoying at times. Not that I actually have to deal with it that often, but I'd be lying if I said that wasn't something that's always in the back of my mind when I'm public.

MM: Yeah. It seems like there's always going to be a lot of opportunity for the people that are just focused on contribution and creating serendipity on platforms like this, because it is, it's just not connecting.

BR: Yeah.

MM: Which I always feel like is the same role as venture, a similar muscle, actually.

BR: Yeah.

MM: But I do think that you're very right about that. There is a certain hard cap of which people are no longer really reading it in your voice or the good faith culture voice of the space anymore, and then it gets totally taken in different directions.

BR: Yeah. My Twitter profile picture is a green gradient. At some point I realized I'd love for something that's more of ... It's just a blob rather than a picture of me.

Even in my old Twitter picture, I don't even remember the last time I had a picture of me, it was probably, I don't know, a 21-year-old version of me. It's like, okay, someone could just look at this, and they're like, "Who's this kid? Why is he tweeting things like he knows what he's talking about?" Or whatever.

It's like I just want to remove all of that. It's just like evaluating my thoughts for who I am and that's it. I don't want some weird, like, okay, this is what this person looks like and now I've assumed that this person has some weird perspective, or I think that they're dumb or smart or whatever, based off of that.

MM: Yeah. People, they really do project a lot up to the small scraps of data points that they get through online.

BR: Yeah. Yeah. They'll latch onto it. Even now, right?

MM: They will.

BR: When I tweet, I'm sure they're like, "Ah, just typical VC tweeting something."

MM: But it's good. I like the green blob. I think it projects the right ethos. It's like, yeah, it's just a faceless, voicing thoughts into the ether.

BR: Yeah, it's ...

MM: It's what the internet used to be.

BR: It's sort of inspired by if I could have been pseudonymous in another life if I could have actually built a brand publicly without ever having to show my face, would I have? For sure.

I think given the role and job that I have, you can't really do that, but what's the next closest thing you can do is don't make it super easy to become a target of, like, here's your face online.

It's at least just be yourself, and you can abstract, so when it does get picked up from another town square a couple of cities over, it's like they don't actually need to know who you are or make some weird biases of who you are.

MM: Yep. Yeah. Do you think that's going to increasingly become the norm online?

BR: I personally think we'll look back at this era of the internet and think that we're all just crazy that we used our real names and our faces online.

“I personally think we'll look back at this era of the internet and think that we're all just crazy that we used our real names and our faces online.”

I think it was a detour of the internet. I think Facebook, after we just created that we went from a shift of you should never have anything online, like when I was a kid. It's like, don't put your name or anything, and then Facebook somehow broke that. It was like, yeah, of course you should have your name and all of your photos and every single thing you've ever liked online

MM: Put everything online. Yeah. Yeah.

BR: I think it will gradually shift back. Maybe there will be a big change of like, oh my gosh, everyone's getting canceled, blah, blah, blah, but I think there is a little bit of like, we're all a little bit crazy for having our real names on the internet, I think.

MM: Yeah. How do you think about this when sharing somewhat, as original, as original can be, thoughts in terms of writing and things like that and actually authoring stuff? When do you go to the page and think something is worth publishing, putting your name behind it, that kind of thing?

BR: Yeah. This is a real curse that has happened to me over time. I'm much more tough on what I put out publicly from a writing perspective in that whatever I put out I want it to be polished and can go through the rigor of the public of, like, yeah, Blake actually knows what he's talking about, or he researched that well.

I actually think it's probably the wrong ... I've overcorrected and I probably would be much better served just putting out my raw thoughts and not having to go through, like, here's the whole background of a space. Instead, it's just like, here's ... Assume that the reader understands the space fairly well and just give my thoughts there.

I think it becomes more tough, at least for me, the deeper you are into your career. Early on I used to write stuff, and, again, I'd look back and I cringe, but it's like at least I was putting stuff out there. I think, again, 23-year-old self, I would tell myself, "Write way more and really solidify your thoughts out there in the world."

MM: Do you think that that will increasingly be the currency that people find serendipity going forward? Because I wonder if Twitter will continue to be the town square and how it will all fit together.

BR: I think it's Twitter and writing, let's just say Twitter and Substack or wherever, these places have become way more noisy.

It's harder to differentiate yourself. For me, I'm always thinking about, well, where do you actually create content that no one else is? Is that the right place to dig in or do you just go and make content where your audience already is? I just always go back to someone who should really create a great YouTube channel around this stuff.

MM: That's the core atomic unit.

BR: Yeah, I just think it's just sort of mind-blowing to me that no one from our world has fully cracked that. I refer to it as smart YouTube.

Most of YouTube is junk food, but there is ... You and I would love to watch normal, smart YouTube stuff.

MM: I do. I love it.

BR: Yeah. I think there's just a big opening. Right now, it's just educational and then documentaries, and then junk food. I think there's somewhere in between all of that.

MM: Yeah, I think that sounds very right, especially short-form video, all that kind of stuff, or shifts.

BR: Yeah, yeah. Yeah. I think someone will nail TikTok as well at some point.

MM: It's surprising how few tech and VC people have gotten this.

BR: Yeah, yeah. It's like zero.

MM: We're all so used to hiding behind a screen or something.

BR: Yeah, exactly. It's probably just who we are as people, just like our personality types.

MM: Yeah, it filters.

BR: Just goes more towards writing.

MM: True. Where do you go to find inspiration? What are your favorite corners of the internet these days?

BR: I spend way too much time on Reddit and TikTok.

MM: Reddit is what Google search used to be.

BR: Yeah. I think it's more of you see ... I don't know. Let's use you go to the coffee subreddit as an example. You go down the rabbit hole of coffee. Again, you would think that's not a deep rabbit hole, but, like, oh my gosh, it is a deep rabbit hole.

MM: So deep, yeah.

BR: You go to the Wikipedia page on the side, or the wiki that they put together, and it's like, here's the buying guide. Here's the 9,000 things of how you should think about this, and then you're like, "Wait, some random person did this for free? What?"

MM: Yeah. It's so in-depth.

BR: "They did this because they're so passionate about this?" Then, by the way, there's probably 200,000 people that go and read that. I was like, "Okay, wait. This is actually crazy."

I just love finding random subreddits, like sub 50,000 members, and being like, "This is a passionate community. What's going on here?" I love also following drama within hobbies or communities.

I think it's just such an interesting look of, okay, why is ... I don't know. I went down a rabbit hole of Warhammer figurines and things like that. It's like, here's all this weird drama that's going on within the space. I'm like, "This is amazing."

MM: It is.

BR: There's probably learnings of why this is happening. Maybe there's a company that gets formed out of this. I don't know, but at the very least, you get to see ... Reddit is, for better or worse, the purest form we have of observing all of the internet and how the hive bind would interact. As long as you acknowledge it is, it's the hive mind.

“Reddit is, for better or worse, the purest form we have of observing all of the internet and how the hive bind would interact.”

You could read an ask Reddit thread to me and I could tell you what the top 10 posts will be, top 10 comments will be, just automatically.

That's how good of a pulse I have on how Reddit thinks, which is scary and bad, but it's become so obvious what people want on Reddit.

I spent a lot of time on Reddit. I go down a lot of rabbit holes on TikTok as well. TikTok as a search platform is really fun and interesting to go and search a weird hobby, like coffee or something. You're like, "Wait, what? Oh my gosh. There's all this amazing content that's out there."

Between that, those two, and then I try and ... I also go down a lot of YouTube rabbit holes as well, but I don't know. It's not systematic at all. It's very just follow whatever breadcrumbs.

MM: Following your curiosity, yeah.

BR: Yeah. Whatever breadcrumbs are out there, I just chase down.

MM: Yeah. It's like quality breadcrumbs, too, I feel like is what you're chasing.

BR: Yeah. Yeah, exactly, exactly. Yeah. It's ideally not junk food, but occasionally do end up with junk food.

MM: Yeah. Yeah. Whole wheat.

BR: Exactly.

MM: Yeah. It reminds me ... I think I feel like one of the best questions to often ask on a topic is always what is the most contested issue currently.

BR: Yeah.

MM: To get at the crux of what is tearing them apart and what is interesting and what people are thinking of. Then you have to fill in so much context to even understand why that is the crux of an issue.

BR: Yes.

MM: But you'd be surprised. Yeah, there are so many things that have hotly-contested debates in aerospace figurines or something like that, and it's like why are there even debates?

BR: Yeah. I mean, it's more of the fact that these people are so passionate about this. It's like these people would all do this as their full-time job if they could, but they're probably working some nine-to-five, or whatever it is.

That's where their real passion is they're sitting and debating the future of some random thing. It's like, "Oh my gosh, that person is amazing.” I also want to go down the rabbit hole of every area that they spend time in. My view is most VCs just default to, I don't know, what do other VCs spend time in and think about? For me, it's much better to just try and observe what's actually happening. You're just like, "Oh, wow, okay, this is a thing. Is it venture-backable? I don't know."

“I also want to go down the rabbit hole of every area that they spend time in… For me, I try to just observe what's actually happening. You're just like, ‘Oh, wow, okay, this is a thing. Is it venture-backable? I don't know.’”

Again, all this weirdly gets connected over time. I try and reach out to a lot of these people. Mainly, I don't know if it's a researcher or if it's a company. It could be really niche, but I try and just build those connections and dots over time so that I can connect them all.

That's the best part of this job is actually connecting all these pieces.

MM: Couldn't agree more. Yeah, it's the most fun.

BR: Yeah.

MM: It's like Reddit and many areas of the internet where people are just completely obsessing over things, it's a really good way to filter for the people that are in the top one or 99 percentile of just being obsessed with a thing.

BR: Yes. Yeah, yeah.

MM: There's probably no better way of finding them in the entire world.

BR: Yeah, exactly. It's just like, "Why are they so obsessed? What's going on here?" As you continue to peel the onion back, it's just like, "Oh, I can see why they're obsessed. Yeah. This is crazy."

MM: Yeah. Really interesting.

BR: Yeah.

MM: Yeah. Yeah. My last question for you in closing is just how do you think that venture and the internet are going to change over the next decade? How is it going to change how we do this job and all this kind of stuff?

BR: I think my view is more and more power to the individual, just that would be my overall theme in that, I think, in direct contradiction to everyone will regret having an online identity of themselves. I also think everyone should really invest in their personal brand and their personal audience.

I think being known for anything is, well, not bad things, but being known for being unique is good. A lot of what I think the next decade on the internet will be about is how you express yourself uniquely and build a personal brand.

“I think being known for being unique is good. A lot of what I think the next decade on the internet will be about is how do you express yourself uniquely and build a personal brand?”

I think there's another piece, which is there's some probably really crazy thesis I could say around AI and how all that evolves and whatever else. I think that'll happen. There's going to be some really crazy stuff that happens around AI, but I don't have a strong enough thesis today to tell you how that evolves. I think it's just more and more value accruing to the individual and rewarding the individual.

MM: Yeah. It's interesting how, yeah, it becomes more and more atomized, but then people still find themselves craving the community and the groups and all that kind of things, rebuild what they've been ripping apart at the institutional seams for a very long time.

I think it's good. It's just like a reorganization. It's kind of, okay, now we're building from first principles. How do we actually want it to be organized and which people want to work together?

BR: Yeah. Yeah, I think that's right. I think it will be very interesting to reflect on 10 years from now, like how the world's changed, because it's just ... If I've learned anything, I can't predict any of this stuff. Instead, it's just trying to observe and pay attention and make sense of it as you can.

MM: Great answer. Wonderful. Well, thank you so much for coming on the podcast.

BR: Thank you.

MM: Blake, it was a pleasure.

BR: This was awesome.

Subscribe for more episodes to come: Spotify, Apple, Google, Amazon, and Overcast.

Highlights:

• The core question behind Universe is ‘how do we empower everyone to build the internet?’ (thus making the web more like NYC and less like suburbia). Making tools in this way is similar to urban planning in that it involves building frameworks and kits that let regular people fill in the blanks.

• The story of technology tells of a shift from institutional to individual power — one person can do so much more than could’ve done several decades ago. Following this trend, technology should increasingly reflect what humans want: to be able to manifest our ideas, explore and live our lives to the fullest, and have meaningful experiences with the people that we love.

• One place to take inspiration when thinking of ideas for a company (a process that naturally forces ideas to become higher fidelity by engaging with reality and what people will pay for) is by looking at the best things that people have made in other industries and endeavoring to understand what made that thing great, how it works, and whether there’s a way to remix the idea in a different environment.

MM: Hi everybody. Today I’m joined by Joe Cohen, the co-founder and CEO of Universe, a mobile-first website builder that aims to empower everyone to build the internet.

Our conversation covered Joe's early enamorment with the internet, his view on technological and cultural progress, the changing role of the digital designer, and advice for young toolmakers. I hope you enjoy.

MM: Hi, Joe, and welcome to the show.

JC: It's great to be here.

MM: Joe is the founder of Universe, which is a magical new way to build websites. My first question for you, Joe, is how did you come to the idea behind Universe, and how do you navigate the idea maze?

JC: I think it's a great way of putting it in terms of the idea maze, because it really has been a maze that's unfolded over almost a decade. I think for me, I grew up in New York, but I like to say that I really grew up on the internet. The internet is where I found my passions, my inspiration, my energy.

I got my first Mac when I was 10 in 2001, and that thing blew my mind. It was Bondi Blue iMac, it looked like it came from outer space. It had the coolest thing on it, which was the internet. It had a web browser, and that opened me up to the world. I'd grown up in a pretty small community, so getting online for me was a revelation. It got me excited about the world. Ever since, I've been living and working and thinking online, but from the beginning I felt like the ways of making things on the internet didn't feel like they were fitted to me and to how my brain works. There are really, I would say, two ways of making things online.

There's writing code, where you have the full capabilities of the web at your fingertips, but you need to bend your brain to work in the way that machine works. You're fitting your ideas into code. By definition, it's an abstraction against those ideas. I found that I can write code, but it's not how I want to think. It's not how I want to spend my time. Then you've got these products that have come around that have built... We call them website builders, and they built these templates for these canned websites that you can then fill in with your own content.

I found that those were frustrating because I couldn't really be creative. I couldn't really make something that was my own. That was a deep-seated idea from when I was a kid, as just a hunch more than a fully baked concept. Then I started my first company which was totally separate. It was in the education tech space. We built a learning management system, a platform for classes online. I realized in building that startup and building that product, even though I have good design sensibilities and know what I want, if I wanted to make a change to our homepage, I'd have to go bug an engineer to do it.

This is eight or so years ago, and I'm thinking, "Man, there must be another way to do this. There must be another way." This is really a design problem, it's not a technology problem. The tech is now here to build alternative ways of building things on the internet that are both open-ended like code, but easy to use like consumer applications. That's possible now.

It became clear that it was possible because of mobile. Mobile was this breakthrough. Mobile wasn't just about phones. It was this idea that for the first time ever, computers would be universal, that my experience of being a little nerdy kid on the internet, that would become mainstream and all the things that nerds do on computers would become mainstream behaviors. That was going to be a revolution.

“Mobile wasn't just about phones. It was about the idea that for the first time ever, computers would be universal — that my experience of being a nerdy kid on the internet would become mainstream and all the things that nerds do on computers would become mainstream behaviors.”

I thought, huh, if you could pair this universal computing platform with an open-ended graphical and visual way of creating the internet, you can change the internet. You can make it something that is a much more democratic and diverse and much more representative of the full spectrum of humanity, of our ideas, of the things you can do with technology. I thought that's what the internet really needed. It needed to reflect back more of the people using it as opposed to just companies in Silicon Valley or people who have technical skills. That really began as the provocation. It was like how could you empower everyone anywhere to build the internet without any technical skills? I was really inspired by some old school products that never broke into the mainstream, but had some really good ideas.

The classic one is HyperCard, which for people in our circles is a touchstone, but I started using HyperCard. I never used it as a kid, it was before my time. But in 2013, I started using it on my modern Mac, and I was totally blown away. I thought, "Wow." For those who don't know what HyperCard is, it's a visual creation tool that allows people to make static pages, but also interactive things. This was in 1987 before the web came out. So a long time ago, over 30 years ago, but the ideas in it were so ahead of their time that I was inspired to take those ideas and put them into the phone. So the initial idea was really a HyperCard for the iPhone. I ended up meeting with Bill Atkinson, the creator of that app, and it was just a super inspiring moment. So, that was the initial inspiration for Universe. Over the years, we've navigated that idea maze.

We've taken iterations and pivots along the way. So the first one was becoming a website builder, not just this HyperCard-y thing. We realized that we needed to make this practical, we needed to make sense to people who weren't into esoteric tools. Then even with the website builder, making it a full-fledge website builder, making it support commerce., and actually now, we're on the precipice of our next pivot in that journey of the idea maze.

I think the question's great because to me, I think the most interesting companies are, or the most interesting projects, are not defined answers. They're really open-ended questions, and the point of the company is to answer that question. So the question at Universe is how do you empower everyone to build the internet? Over time, we get to answer that question in better and better ways as we learn new things, get more resources, build foundational technology. Over time, you should be able to answer that question better and better. That's what we're up to.

“I think the most interesting companies/projects are not defined answers. They're open-ended questions and the point of the company is to answer that question. The question at Universe is ‘how do you empower everyone to build the internet?’”

MM: That's amazing. How would you say that question has evolved over time? Is that something that at the beginning was broader and it got more refined, or is it something that stayed steady?

JC: I think the question has stayed steady. The question of how do you empower everyone to build the internet, that's been the animating question from day one in this 10-year journey, but the answer has changed a lot and will continue to change. It will change in its angle of attack, like how are you empowering everyone? But it also changes in its fidelity. As you immerse yourself in an idea, it gets more high fidelity. It gets more detailed in the picture.

So, that's the biggest change. When you're on the precipice of doing a thing, it's so hazy. It's blurry. Then over time, it gets clearer and clearer and it gets clearer in your head, but also your answer gets clearer. I think that's one of the benefits of doing something as a company, is it forces you to get that clarity. In other contexts that are divorced from a real world thing, you can leave ideas in the idea space. They don't have to engage with reality to get a little bit sharper and more high fidelity.

“One of the benefits of doing something as a company is that it forces you to get that clarity. In other contexts that are divorced from a real-world thing, you can leave ideas in the idea space — they don't have to engage with reality to become sharper and more high fidelity.”

MM: Yeah, and they actually have to prove themselves by having a customer market.

JC: Exactly.

MM: Yeah, super interesting. At a high level, where do you see the future of computing going? How does Universe fit in, and what are the broader trends that you're forecasting?

JC: Well, I think we're recording this in the beginning of April, which is-

MM: Worth time stamping?

JC: It's worth time stamping, because things are changing so quickly, and it's really exciting. It feels like we're at an inflection point moment in technology and computing. It'd be foolish to try and forecast it 100%, because I don't think any of us know where this is all going. That's part of the fun of it.

Look, I think that if we think about what computers are, what software is, at the end of the day, what animates us about this stuff is that these technologies give us US new tools, new tools for doing. What's cool about that is toolmaking and tool using, that's humanity's birthright. That is the thing we do. We make tools, we use them. They allow us to extend our reach, to do things we couldn't have done before. I just had this thought yesterday, it was a dumb thing, but I was on a plane. It was one of those planes where you have to walk up to the fuselage to enter the plane.

There's a ladder. I thought for a second, "Wow, humans created this thing that's so big, it's like a bus that's floating 20 feet above where you stand that you climb into, and then we hurdle through the air across the world." It's just an incredible thing, and that's a tool and it's surpassing our biological limits. But obviously we've been doing that forever, and I think that what we've seen over the past 50 years with computing is really an acceleration of that tradition of toolmaking.

If you think about the past 10 years, we've established a new baseline of tools that are really powerful. We call them apps. Apps are new kinds of tools. They're way more dynamic and they're way more sophisticated than any tool before them. They've now become the baseline for what tools are in the world. I think that we're now on the precipice with these AI technologies and everything else that's happening for a new generation of tools that will just take that to the next level.

I think that these tools will start to feel even more dynamic, even more sophisticated and customized. So, they're just going to accelerate what we've seen. To me, what that means is that for every person, they have their own tools, their own custom interactive tools that allow them to do whatever it is that they want. I think that that's going to just bring up the baseline and be the norm in the future. We're going to look at these kinds of tools like we do with apps today, but I think the implications of that are vast and unknowable in the way that the implications of unleashing apps on the world were completely unknowable 10 years ago.

“What this means is that for every person, they have their own custom interactive tools that allow them to do whatever it is that they want.”

MM: That's a great answer. I love the idea of everyone has their own personal toolkit almost, and they're totally customized to how they work and think. Right now, tools are so one-size-fits-all and it's very limiting. It forces people in directions that not necessarily are the ones that they intended.

JC: I think the key thing there is hackers and nerds, we've customized our tools.

MM: We've had this power for a very long time.

JC: But I think what's exciting is that we now have technology that allows us to customize tools without the user even saying that they want to customize a tool. Just by using it, the tool's becoming custom.

MM: It's a great metaphor. I like that a lot. I'm curious to hear how you think about and conceptualize revolutions and specifically technological ones because it seems like we are definitely in the midst of one right now with AI. But I'm curious how you think about these cycles, and how they interact with culture and all of these broader trends?

JC: Yeah, I want to share this idea with you that I think is worth repeating, which is I have this theory that people often think about the history of computing as a story of computers getting smaller and cheaper and faster. I think that's totally true. We went from mainframes that were instruments of war in the 50s to now a smart computer on your wrist.

MM: Pretty amazing.

JC: That has more computing power than the thing we sent to the moon in the 60s. That's incredible, but I think the more interesting story is the cultural implications. I think really what's happening is we see a pendulum swing of power. I think that the story of computing is actually much more about power than it is about smaller, cheaper, faster technology. What I mean by that is we see a shift from institutional power to individual power, and that really is the story of technology. As a human being today, you can just do so much more than you could've done 10 years ago, 20 years ago, 50 years ago. I think that story is going to continue, and it's really exciting.

“The story of technology is the story of a shift from institutional power to individual power. As a human being today, you can do so much more than you could've done 50 years ago.”

One individual is going to be able to do what 100 people used to not even be able to do. I think that story is going to continue and continue, and I think that the interesting question is which part leads which part? Is the technology leading the way, or is the culture leading the way? What's the cart pulling the horse? In the sense that if you think about the past 10 years post-mobile, we've seen a number of different moments come into play.

Right now, we're in this AI moment, which to me feels different than some of the other ones in the past decade. But I think they're of a kind. Crypto is the last one, and crypto was all about individual power. It was about this idea that you don't need to be relying on large institutions. A decentralized internet that you're in control of, whether it's for finance or creativity, or whatever.

I think AI is also, in that way, giving you just these super tools, these superpowers and abilities. So ultimately, I think the story of computing is this interplay with culture and this over time movement from institutional, large power, to putting that in the people's hands. By the way, I think that has good and bad implications because obviously, the positives are that individuals now have a lot more capabilities, but really powerful technology cuts both ways.

It also gives people who have nefarious intentions a lot more power, so these are two sides of the coin. But ultimately, that's how I contextualize these shifts. I think Kevin Kelly has talked about this a little bit, but he talks about technology having a way, this idea of what does technology want? I do think that there is that effect here.

I think that technology wants a thing, and I think that's really a reflection of what do humans want? What do humans want? We want to be able to manifest our ideas. We want to be able to explore and live our fullest lives, and have meaningful experiences with the people that we love. That's what humans want. We want to have agency and control over our minds, over our ideas, over our lives, over the world, over our corner of the world. So over time, technology will do that. At the end of the day, we, humans create this stuff. It's a reflection of us.

“I think that technology wants a thing, and it’s really a reflection of what humans want. We want to be able to manifest our ideas. We want to be able to explore and live our lives to the fullest and have meaningful experiences with the people that we love. That's what humans want.”

So I think it's often easier to de-personalize technology when we talk about it, but at the end of the day, humans create technology. Humans create this stuff. One of the things I like to say, and one of the things that guides my work is we often talk about things in business and in markets as inevitable. Like markets have an inevitability to them, like, "Oh, yeah, it's inevitable that smartphones would exist or AI would exist," or something like that.

But it's not really inevitable. Even take the iPhone. Yeah, sure, maybe small phones in your pocket would be inevitable, but would the iPhone be inevitable? Would the interface of the iPhone be inevitable? I don't think so. That's because a group of people who had opinions and values got together and made it happen. So, it's a reflection of that, of culture in that way. I think that software and computing creation is just another form of culture. I think the same could be true for music. Maybe rock and roll was inevitable, but were The Beatles inevitable? I don't know, probably not.

I think that it's easy to lose sight because the work that we do does engage with the market, to think that any effort by one person or group of people is inevitable, but it's really not. We do have an opportunity to channel the course of how this stuff works, and futures are path dependent. So, the things that we do can open up whole new fields. That's why I think there's an imperative to bring ideas into the world when you have them, I think to continue charting a future where people have that kind of agency, and are not just passive consumers of the world.

MM: I love that answer. I always think about small groups of people with a very specific intention and taste. It's like the core atomic unit of change. I'm curious how you think about this theory as it intersects with what to build now and where we are in the current cycle?

JC: So maybe I'll make it specific to Universe, because I think it will help frame it. So, Universe is a website builder. It's a website builder that has a totally new kind of interface that allows someone without any technical skill to make something totally custom. We do that with a grid-based interface that's drag and drop and fun and playful and super powerful.

It works on your phone, so you can use it wherever you are in the world. When inspiration strikes, you can make your idea more real, put it out on the internet, get a domain, all this stuff. Really, I would say it's the best DIY tool for building something on the web, but it is DIY. You do have to do it yourself. By doing it yourself, you're basically playing the role of designer.

You're using this thing to design your idea. We have basically built this design tool in your pocket, and I think that the next generation of tools will behave more like agents, like we talked about. So instead of it being a design tool in your pocket, it's going to be a designer in your pocket. You're going to be able to tell this thing what you want, and it's going to make it, and it's not going to make it 100%.

You're going to have to tinker with it and play with it, and you're going to need to say, "Oh, I want it to be a little bit more like that, or a little bit more like this." It becomes a dialogue. So for Universe, that's what we're all about at this moment. We're taking the next step in our journey of this idea maze and saying, "Look, we actually have learned a lot by building the best design tool, for building things on the web, in your pocket available anywhere."

We're going to take those learnings and say, "Actually, how do we make that 100 times easier? Well, we're going to remove the need for you to play designer, and we're going to just do that for you. We're going to do it by understanding who you are and what you want and what your ideas are. We're going to give that form, and it's going to be fun and playful." That's I think the nature of where we're at right now.

I do think we're at the beginning of this renaissance, so I think things will unfold over time, but that's our animating inspiration right now. It's a designer in your pocket. What does that look like? Just think about that. Okay, I'm a teacher. I'm teaching a class on American history. I want to make a website for my class. So, I tell this thing, "Hey, I want to make a website for my American history class. I want it to look like Revolutionary America. Pull in the Constitution as the background."

That kind of conjuring feels possible now in a way that just was a pipe dream five years ago. I think that's incredibly exciting. So, we are embracing that wholeheartedly and thinking about what the Universe mission looks like in that context, the Universe mission being empowering everyone to build the internet. What does it look like in a world where technology now exists to do a lot more of it for you, and to really augment your sensibilities and ideas at a whole other scale? So, that's what we're thinking about.

“What does it look like in a world where technology exists to do a lot more of [your work] for you and augment your sensibilities and ideas at a whole other scale?”

MM: Amazing. How do you make decisions around aesthetics in those types of scenarios where it is so much up to your individual choices of how you program something to whip them up?

JC: So specifically you're asking if we're playing that designer role, how are we making those aesthetic decisions?

MM: Yeah.

JC: Good question.

MM: It sounds hard.

JC: We're still figuring it out, but that's why it's fun.

MM: Yeah, totally.

JC: A good question or a good provocation animates you to think in that way, because actually if you ask GPT-4 to make you a website for a thing, it can do it, and it'll do it by spitting out code, which is not actually a website. You need to go take that and put it into a development environment, host it, all that stuff. But it's going to look like dog shit. At the end of the day, it's going to look like the average website on the internet, which is not very good. So the goal is here to be like a mirror, but a magic mirror, where we refract back a better looking version of you. That's the job of a great designer, so the best designers in the world don't have rigid aesthetics.

They're actually able to understand their client and make something that represents them, and that can represent itself in many different aesthetics and styles, but they're just principles of good design that are at play in all of them. So I think ultimately, you need to break it down. When we say like a web designer, what do we really mean? Well, we mean content, we mean layout, and we mean style. So content is like what you're putting on your website, layout is where it goes, and style is how it looks. We could even break style down into colors, typography, and then decisions around spacing, margin, all of that.

So you really want to break down each of these different components and then think, "Okay, how can you make intelligent decisions based on each one of those things?" So if we just think about color for a second, color's really interesting, because there are colors that objectively work well together and others that don't. You can actually figure that out mathematically. You can figure out what colors work well together, which don't. Color theory, so we want to programmatically use that framework to match to a user's intent.

So for example, if someone says they want a website that looks like the LA Lakers, we should be able to take that, understand what they're saying, and then map it to a harmonic array of colors that might not be my personal aesthetic, but is what the client or the user in this case wants. So I think that's really it. It's like how do you build frameworks that make it so you can't really make a mistake, but everything feels personalized and it doesn't have a very narrowly defined aesthetic. Yeah, that's how I think about it.

MM: I like that. It reminds me of high up on the ladder of abstraction or something, so that the primitives when you put them together like building blocks, they by default look pretty good. Which is a nice way of empowering everyone. I'm curious, how do you see Universe's role as it relates to the web? Is it a steward? Is it a helping hand, a coach?

JC: It's a great question. So I think the web is the greatest thing that humans have ever built, because it's this collaborative creation. It's been built by billions of people interacting together, which is so cool. It's just so cool that to contribute to that, to that thing, and not just contribute by putting a webpage out there, but building this engine that allows other people to put their mark on this corpus and contribute to it.

So to me, the beauty of the web is that it has no single owner, no primary architect or designer. To me, I think my hope is that the internet becomes more and more diverse and more and more interesting and eclectic. The metaphor I like to use is I want it to look more like New York City and less like suburbia. If Facebook represents suburbia, I want to be the anti that, in that way. So we say, "Okay, so what is the role that we play in doing that?" I think ultimately, the way that you nudge towards the future that you want, my bias is to interact at the tooling layer to build tools that enable the kind of future that you want.

“My hope is that the internet becomes more diverse, interesting, and eclectic. I want it to look more like New York City and less like suburbia.”

So I think our role at Universe is really to engage at that layer of the stack, to influence the output by shaping the tooling layer. So I wouldn't say that we're a steward of the web, because I think that's bigger than any one company or thing, but I think that you can influence the arc of the web by making new kinds of tools. I think that there's a responsibility that comes into play, because I actually think a lot of the web is in a pretty crappy place right now. If you use the web on your phone, it's a terrible experience in a lot of cases.

You go to a website, and maybe you're reading an article, and immediately you get a pop-up for some promo or subscription, and you X that out if you can find it. Then you get this thing on the bottom that says accept cookies or not, and there's a banner, and it's just lousy. I think that ultimately, yeah, the user decided they wanted to do that, but the platforms enabled them to do that.

The tooling enabled them to make those decisions, so I think you have a responsibility as a designer of a tool or platform to arc towards positive patterns. So that's the responsibility and that's what I think our input is. I think over time, hopefully we earn the ability to push forward the state of the web, and not just have it represent all of us, but to really push the boundaries of what the internet can look like and the ways that you can experience it.

We right now have a conception of what a website is, but over time, I'd like to broaden that conception. I'd like for a website to be just a lot more. The internet as a canvas technically is extremely broad, and we don't use 1% of what it's actually capable of doing. So over time, I'd like to stretch that. I'd like to stretch what we think of as a website, what we think of as the internet, and really do that by concentrating on the tool layer and opening up people's imagination in that way.

MM: I like that. How do you see the role of the designer changing, where now, the designer is more shaping the tools that allow anyone to design their own thing? Are you making less decisions that are pixel details and it's more higher level choice architecture? I don't know, just curious how you think about that.

JC: That's the role we've been playing for our whole journey, so for as long as we've been building Universe, we've been designing tools for other people to design. You're a meta designer, in that way. That's what attracted me to the problem in the beginning, because my background is as a designer. So to me, the ultimate UI design challenge was making a design tool for the masses.

That was just a really hard thing. How would you do that without a keyboard, without a mouse on a tiny screen? Impossibly difficult design challenge, but that's the appeal of it. You get to then work on that, and out of that came a grid interface and all this stuff, and you learn about oh, when you're working on a phone, you don't have a lot of XY space, you don't have a lot of screen real estate, so you have to use the Z space.

You have to use time as the element to unveil complexity. So you show one thing at a time, so you learn as a meta designer what your tools are, what your ingredients are for shaping decisions. I think we're now in this next era of meta design, and it's really exciting. I think it's blue ocean. We don't really know exactly what the levers are that we have, but yeah, the way I think about it is the terminal point of design is you're making an image.

You're designing a thing that's one of a kind, it's static, and you're sharing that. Maybe you're making a poster. It's one of one, and maybe you're making a website, and a website is fairly static, but if the user changes their view port, they resize their window, or if they look at it on another device, it changes its form, so it has a little more dynamism.

Then you might design an app that actually holds state and it interacts in different ways, so now you're designing in a little bit more of an abstraction. You might use auto layout, but I think that when you're making a thing that lets other people make things, you're exercising a whole other meta level of design. You're really designing frameworks and kits to empower people. I don't think that that exists actually as a discipline, but it should.

“When you're making a thing that lets other people make things, you're working at a whole other meta-level of design. You're designing frameworks and kits to empower people.”

MM: I agree.

JC: That is a whole pattern and school of design. I think the closest thing to it in other fields outside of computing and technology is urban planning. Because in urban planning, you're not designing the finished thing. You're designing a thing that lets other people fill in the blank. I'm biased, but to me, the most successful example of that is the New York City grid, which was not a fact of nature. It was invented. So New York, until the grid, which was unveiled in the 1800s, it was very shoddy and ad hoc. So Lower Manhattan is not on the grid, so it's winding roads, and this burgeoning city, they were just building it as they needed it.

“I think the closest thing to [toolmaking that we have] in other fields outside of computing and technology is urban planning. In urban planning, you're not designing the finished thing. You're designing a thing that lets other people fill in the blanks.”

At some point, they were like, "Okay, this is the capital of the new world. We need to think ahead, we need to come up with a plan." What they did was they laid out a grid on the city, and it was a pretty regular grid, but it had a few interesting nuances to it. One was that bifurcating the grid was Broadway, which cuts on a diagonal, so it intersects with the grid at different points, creating these really interesting parks. So like, Union Square and Madison Square Park, these are these chaos moments in the grid.

You also have Central Park, which took prime real estate and said no, no one owns, and also there are parameters. So for example, no one building can span more than one square block. So you could do anything you want in that square block, but you cannot exceed that block. You can make the ugliest building in the world, but it can only be one block large, and that would mean you need to put together all the parcels on that block. Then they did realize that this grid was not just two-dimensional, it was three-dimensional.

So people were going to build up, and if people built up, if everyone just filled the maximum space, you'd end up in a city that had no light on the ground. They said, "Okay, actually there's an envelope that you need to adhere to in height." So that's why the Empire State Building, for example, tapers as it goes to the top, because that fits the envelope that the city laid out in the 1900s.

So, I just think that's an example of really good city design, because it's laying boundaries and constraints, but it's not filling in every detail. I think an example of inhospitable or inhuman or inorganic city design is, and designers love these people and love the aesthetics of these cities, but they're not actually good, so the Corbusier vision of a city was you'd have these elevated roadways and you'd never need to leave your complex. They were centrally planned, modernist utopias that didn't allow for any individual expression. The designer knew everything, but the reality is that's a cold world that no one wants to actually live in. It has no personality. Brasilia was the manifestation of that idea, and it's an amazingly beautiful city in photographs.

You look at Oscar Niemeyer's designs and these incredible structures and all this stuff, but it's just not a place you want to be. It doesn't have life. It doesn't have that organic-ness. So I think when you're designing systems for creation, when you're designing tools, you're really playing the role of constraint designer and you want to design really good constraints, and then let people do whatever comes to their mind. So, that's how I think about it. By the way, programming language designers do that. That's what they're doing.

MM: Totally. Yeah, they're just using a different medium. It reminds me a lot too of what people coined to be the Ivory Tower type of design, especially in UI design, where it's like Swiss Grid's very perfect, but it's not actually allowing for much expression or people to customize in any way.

It's just a top-down depiction of this is what is good, you must adhere. It makes me think. I think that one of the things that makes Universe really stand out is the very, very broad spectrum of expression that people can have within the tool, and make something that really feels like them. It makes me wonder, what are some of the craziest things that you've seen made with Universe?

JC: Every single day, we see designs that will totally blow your mind.

MM: That's amazing.

JC: I like to talk about it as yeah, it's this vernacular internet. People are breaking a lot of the patterns that we take for granted on how navigation looks, or how you should show off your products. We've got people starting brands. We have this one creator, she goes by Morgue. She's a TikTok influencer with a million followers. Her idea is she wanted to start a clothing line that was super goth, and there were these spiked hoodies.

Her site looks like you enter this portal of goth TikTok, and that's the tenor of her website, and she's gone crazy with it. Then you have people doing choose your own adventure, weird games, so the types of sites themselves maybe, oh, a shoe wear brand or a personal portfolio, but the way that people are doing that is totally different and the aesthetic that they've chosen is off the wall in some ways.

It's amazing what humans will do, because we get to see what people are making and the amount of work people do, and the way our system works is you have this grid and you can have blocks in the grid, and we have sites with tens of thousands of blocks on them, and that means someone's individually putting this stuff in, and creating all kinds of navigation patterns. It's inspiring, just to see what humans are capable of in that way.

MM: Yeah, that's amazing. It's cool too when they reinvent things from first principles that you're like, "I never would've thought, but it actually makes sense."

JC: Exactly.

MM: My last question for you. I'm very curious what advice you would give to an up-and-coming designer who wants to make things that make other things, and is looking out at this world and seeing that everything is changing and where do they even get started?

JC: That's a great question. My two cents on it, I think that the tech world often confuses itself for the whole world, and it's an important part of the world, but it's a really small part of the world. There is so much amazing inspiration out there in many other fields, both historic and present that should be our muse. I think that a valuable way of making something in a burgeoning new category is to look at the best things that people have made in other areas, understand what makes them great, how they work, and see if there’s a way to remix the idea in this new environment.

“I think that a valuable way of making something in a burgeoning new category is to look at the best things that people have made in other areas, understand what makes them great, how they work, and see if there’s a way to remix the idea in this new environment.”

I also think it's just a good tactic for an entrepreneurial designer who wants to make their own mark, because if you think about it, everyone's circling around the same ideas, and the way that you differentiate is by pulling in inspiration from other areas. So I spend a lot of my time pulling from different things, and that's in the arts, it's in music. For example, the original design for Universe, the app, was very much inspired by musical instruments. I realized that-

MM: I love the little noises that it makes when you play with it.

JC: Yeah, exactly. If you think about tools for making music, we don't call them tools, we call them instruments. You don't use an instrument, you play an instrument. I thought, "Huh, I want to make something that feels like play. I want to make something that allows you to build in a way that doesn't feel like work, because that's where you get the most generative, creative work." So I said, "Okay, let me go deep into this world." I have some experience with these things because I'm a DJ. I spin electronic music and there's actually some really good interface design in DJ equipment.

It's all about these analog controls for manipulating to create an experience. The thing with music tools is that they need to keep you in flow. If you break flow as an instrument or a piece of music or equipment, it's all over. You can't make music without being in a flow state. So I just think it's a really good source of inspiration for software UI design. So I was just talking about cities and urban planning, and I think that's a whole wellspring of inspiration. Graphic design itself, Universe and the grid system, we didn't invent grids.

The Swiss graphic designers, that was their whole thing, like Josef Muller-Brockmann, and this whole idea of reducing the complexity of a space by imposing a grid on it opens up a lot of freedom because now you could think beyond that initial blank canvas. So my advice would be intimately familiar with the state of the art of technology, but then go mine the world and go into the weirdest places, the most untrodden places, and figure out how you can put those pieces together to make something unique. They just make a lot of work.

MM: Amazing advice. I love it. Perfect way to end. Well, Joe, thank you so much for coming on the podcast. I really appreciate it, and for all the incredible fodder, and I look forward to seeing what Universe does next.

JC: Cool. Sounds great.

Subscribe for more episodes to come: Spotify, Apple, Google, Amazon, and Overcast.

Highlights:

• Web browsers are one of the highest-margin and widely-used pieces of software today — creating very little incentive for the major players like Google, Apple, and Microsoft to innovate in this area.

• The vision of Arc (Browser’s first product) is to create a thin client layer that allows you to access your tools, files, and tailor-designed browsing environment on any device.

• Browser’s vision and approach are heavily inspired by moments in the history of technology when two ideas/feelings from disparate places were connected in an uncommon way (e.g. Snapchat’s introduction of play back into social media).

MM: Hi everybody. Today I’m joined by Josh Miller, the co-founder and CEO of The Browser Company. Previously Josh was an investor at Thrive Capital, Director of Product at the White House, and the co-founder and CEO of Branch, which was acquired by Facebook.

Our conversation covered web browsers, the future of computing, and The Browser Company’s unique ethos. I hope you enjoy.

MM: Awesome. Hi Josh, welcome to the podcast.

JM: Hi Molly, it's good to be here.

MM: Amazing. By way of introduction, my first question for you is, where were you when you had the idea for Browser?

JM: So there were actually three different moments. I wish there was that shower moment, I really wish, or I wish I could say I dreamed about web browsers when I was seven, but I did not. The first moment was actually I spent two years as a political appointee in the Obama administration and was pretty bummed, to say the least, about the outcome of the election. And I was walking with a mentor and my boss at the time named Jason Goldman and we were talking about the state of technology, the software we had both worked on, and our hopes for the future, and had honestly at the time a very depressing conversation about how truly only the operating systems and platforms have the agency and ability to change how we use software and the internet and technology for the better, for the worse. It's funny, a few years later you see that even with Apple's move with ATT and Facebook, that even Facebook is at the whims, to some extent, of the operating systems and the platforms.

And so at that moment I decided that I did not want to start another company, I never wanted to build an app again and the only thing that would get me to start another company was the opportunity to build a platform or an operating system that could have leverage on changing how we use technology hopefully for the better in ways that aligned with my values. However, I know nothing about inhalable computing or VR contact lenses, so my takeaway at the time was I would not start a company if there's nothing to do here. And there wasn't.

Flash forward two, or three years, I was at a venture capital firm at the time the firm Thrive had invested in Airtable and Slack and GitHub and Figma was flying around the ecosystem and Notion. And I was just unbelievably inspired by all of the creativity and the originality and these fresh takes on these categories of software that I thought were done and boring and could care less about, and all of a sudden I was getting that same tingle in your body that I got when I first used Snapchat or the iPhone from Notion, a Google doc replacement ostensibly. And I was just so inspired by all these pieces of software and they were all desktop-based primarily, and they all relied on the web browser. They were all web apps either because literally you use them in a web browser like Chrome or Safari or because you use them as a Mac app, but the Mac app was actually based on Electron, which itself is just a white-labeled version of Chrome. So they're effectively just web apps and web browsers.

And so in this moment of seeing all of this creativity and redefinition of categories of software that I thought were done and far from inspiring, they all relied on the web browser, but no one was touching the web browser itself. And so that was the first moment that had this thought, "Wait, why isn't someone taking that level of creativity and almost a consumer artistic lens to the web browser when everyone else is reliant on the web browser and doing things in adjacent categories of software?" But that was kind of from a VC lens.

“And so in this moment of seeing all of this creativity and redefinition of categories of software that I thought was done and far from inspiring, they all relied on the web browser, but no one was touching the web browser itself.”

And then the third and final moment was my wife is Swiss and we always go to visit her family up in the mountains in Switzerland every summer and it was on a walk there. I know it sounds cliche, I also wish it wasn't a walk because it sounds like I make it up, but it was indeed a long walk and my feet were hurting, and that's when I made the connection between, wait a minute, if all of the applications and files that we rely on are now in the web browser and then going to be even more in the web browser in the future, then the web browser starts to look more like an operating system or a platform because it's what tools and applications sit on top of and files sit on top of. And wait a minute, if it looks like an operating system and a platform, that is fascinating and doesn't come around every day, especially without having to invent inhalable computing or contact lenses that'll let you see the world.

And so the combination of those three moments over the course of many years is what led to the Browser company. Probably more than you were looking for, but that is the truth.

MM: I love that answer. It's wonderful, all building on each other. I'm also curious when you say that you were wondering why isn't anyone touching the web browser, now many years later, what would you tell yourself? What is the reason?

JM: Money, money, money, money, money. In fact, I think earlier in my career I wasn't really interested in business models and to some extent saw money and capitalism and all of those things as in conflict with creativity and artistry and the things that really got me excited. At Thrive, I learned to become actually very inspired by business models and money and public market and incentives and all of these kinds of businessy money-related topics as a fascinating creative jumping-off point or set of creative constraints and inspiration for radically new ideas.

And so the truth about web browsers is they are one of the highest margins, most lucrative pieces of software imaginable that power billions and billions of dollars in profit for the world's largest technology companies. And that is quite an incentive not to change it too much. So very practically what that means is, yeah, Google at its core is a search engine company and a search ads company and it's a big mature public company that has pressures from Wall Street to continue its growth and uphold its growth. And it views Chrome not really as a web browser, but as a cheap high-leverage way to get traffic for its search engine and search ads.

“And so the truth about web browsers is they are one of the highest margin, most lucrative pieces of software imaginable that power billions and billions of dollars in profit for the world's largest technology companies. And that is quite an incentive not to change it too much.”

And what that practically means is the team at Chrome can be creative and they are and they can be talented and they are, and they can have dreams of what a web browser can be in the future and they do, but at the end of the day they literally need to ab test any change to Chrome against what does this do to searches? Do people search more or less after we make this change? And the answer is they always search less because if you add anything to it, it distracts people from typing in that search box, which is the URL bar, the Browser.

And so this dynamic applies to Apple, which makes money off the safari by getting a check from Google in the same way, it applies to Microsoft, which monetizes Edge in an identical way, with Bing and Bing ads. And so what I would've told myself before was the reason is because the world's largest technology companies make the web browsers and they make a whole lot of high margin revenue from those web browsers in the form of search ads and that's what's really holding back the category more than anything.

MM: How did you convince yourself that all of those risks were worth it to still tackle this space?

JM: This is going to be an unsatisfying answer, it was an emotional decision. It really was actually driven by people. So I'm building this company with my now second-time co-founder Hursh, who I met when I was 20. We built a company together when we were 20, "company" together when we were 20. We've been to each other's weddings, we've seen each other through all major life changes. And at that point in my career, really what I wanted to do was I wanted to work with Hursh again and I wanted to go hire our favorite people that we had worked with, and I wanted to work on something that was ambitious and audacious enough that we could go hire all those people that I dreamed of working with, Dustin Senos, who runs our design team. When I was 20, I met Dustin and he was the coolest person in the tech world for me, like creative, wildly talented designer, engineer, hybrid and so god damn humble given how talented he was. And I'd always been like, "Man, if I could ever actually work with Dustin."

And the combination of Hursh being really excited about this idea and the audacity and the unknowns the ambiguity of it combined with the fact that as we thought about all of the favorite people in our world that we knew and people that we always wanted to work with, we thought, "Wow, every single one of them gets super, super excited by this prompt and the audacity of it." To be totally honest, it was much less that we convinced ourselves rationally and intellectually that we really could do it and much more that kind of the feeling in the gut was it was just really exciting, it just felt like it would be a lot of fun.

And again, there comes with a lot of privilege by the way at that point in my life and career could take the risk of saying it may go horribly wrong and I'll be okay, which wasn't true earlier in my career and isn't true for everyone. But that was honestly the assessment which is like, "This just sounds like it's going to be a lot of fun," and I think I do my best work when I feel that earnest energy and excitement and enthusiasm. And so for better and for worse, I'm much more of a emotion-driven gut decision maker even though I'm not proud of it at all times, and I am rationally we have decided that we can do this thing. And even to this day looking at the Chrome Oregon, it's thousands of people, we're a nicky little startup with 55. I still don't know if we can do it, but I'm having a lot of fun.

MM: I think it attracts incredible people too that are really drawn to that emotional mission. I'm curious too, how would you define what the big grand ambitious moon shot that you guys are building towards is?

JM: I don't expect anyone listening to believe this. I have a two-and-a-half-year-old son, Sebastian. When he is 10, I want him to articulate his first computer as being our product Arc. Just like when I think back to my see-through translucent blue iMac, that was a defining moment in my life, a change in my life. And so our aspiration is for Arc to be a computer of the future.

Now that's weird. So what does it mean that they're going to build like a Chromebook? No, no, no. The big idea is that we're all underestimating the shift to the cloud. And the cloud is kind of this weird corporate public earnings branding, the cloud, it's data centers and servers and Microsoft earnings reports competing with Amazon, AWS. But really what the cloud is saying is our stuff, our digital stuff is all moving off of our local devices and onto the internet out there somewhere. And it's happening to our applications, it's happening to our files, it's happening to everything. If this computer you're recording this on, if you lost it and you got a new computer, you actually wouldn't have lost anything. You'd log back into your new computer and it'd be kind of annoying to log back in and you'd be bummed you lost the resale value of your old computer, but you would have everything right there because none of it's on your computer, it's all out there on the internet.

And so our big idea is if you play that forward five years, 10 years and you think that this will continue, and I think it absolutely will continue now, we already always believe that, but even since we started the company, the rise of LLMs most recently and AI developments, if you're into crypto and blockchain, whatever it is, you're excited about the future of technology, all of the big macro trends even more so are going to push us further to the cloud and the internet. And so if you believe are going to continue to go that way and more devices are going to pop up, Apple's going to release some new device any day now, I can't get in a rental car without it effectively being a computer, I can't use a TV without it having an app store, if you believe that these devices that are connected to the internet are just going to continue to proliferate and come in all shapes and sizes.

Our view is that a computer should not be one of those in a certain screen ratio in a certain shape. Your computer should be this kind of layer, this thin client that sits across all the different commoditized screen sizes and machines that you use that always has your stuff with you wherever you go, all of your tools, all of your files, all the things that matter to you. And our hope is that Arc is that. And so what looks like a browser today, we hope will look back and go, "Oh wait, that was actually a new type of computer," that if you think about the evolution of computers as going from the size of a room to sitting on your desk to sitting on your lap to sitting in your pocket to sitting on your wrist, we think it's going to get invisible where your computer will no longer feel like a piece of hardware at all. It'll be this thing out there in the cloud sitting on top of everything and that's what we hope Arc turns into.

“Your computer should be this kind of layer, this thin client that sits across all the different commoditized screen sizes and machines that you use that always has your stuff with you wherever you go, all of your tools, all of your files, all the things that matter to you.”

And I feel very confident that's going to happen whether or not we do it or not. So that's a unique part. This isn't a, "We're only going to get to markets if we do it," that's not what I'm saying. I'm saying this is definitely, in my opinion, where computing's heading, we want to be the ones that get there first or get there in the most humane, awesome way. But I think that's happening and already happening whether or not The Browser Company exists or not.

MM: How do you think you want your version of this feature to feel different from whatever would happen inevitably or maybe who will rise up to compete?

JM: As you know, I've been personally much more inspired by people and things outside of the tech world than I have in the tech world. I'm a sociology major by background, my dad was a drummer and a screenwriter before later becoming a lawyer. And I like products that make me feel something, whether that's a cultural product like a film or a piece of clothing that really makes me feel a certain way when I wear it. I really like experiences and products that make me and others feel something.

And so if I think about Google products for example... Actually many people would think competing with Google that I have some disdain for Google. I love Google, like Google Maps, fantastic. I love my little pins. My wife and I are about to move to Paris and it's been so fun to place all these little pins on the map and get to explore. So I love Google. Google never makes me feel anything. It's a very utilitarian company. And it makes sense, there's this culture in Silicon Valley of engineering being central and I actually think that's really good. But what comes with engineering disciplines being central is optimizing for solving problems efficiently.

And I think what that leaves out sometimes is some of the more human emotional elements to the software and the technology products we use. And so my hope is that what we can bring to these, we're calling these internet computers, the next evolution of computing that is agnostic to hardware and sits across hardware. If we want to call them internet computers for now, we hope that our internet computer is the one that makes you smile the most, that makes you kind of sigh a breath of fresh air every time you open it like you're home, is the one that just kind of has that feeling of wearing your favorite outfit or getting in your high school car again or going to your childhood bedroom or opening your favorite magazine on a Sunday. That it's not just the utility of whatever that thing is, it's also the kind of intangible qualities on top of it that kind of stir a certain spirit in your body.

And I recognize that may sound overly romantic or self-important or something, but I just want an internet computer that's a lot more human. So I think that answered. You had another question though, what was your second question?

MM: I think that answered it, that's great. Yeah, great. Something I've always really admired about you is how diverse your inspirations are, and James Turrell being one, and just how deeply you seem to appreciate quality in many different fields. I'm curious where that appreciation originates and what have been your primary inspirations in the journey of Browser and how you think it makes it stand out? I think you've already touched on this, but curious to hear how you articulate it.

JM: To be self-aware, when I've listened to podcasts like this and someone talks about their parents or their family, I find it a little hard to relate even though I find it lovely. But to be honest, my parents and my upbringing and the values that they raised me with. My dad's the sort of person who has this belief that we're specks of dust on this earth and everything is made up and that is actually really exciting because if everything's made up, it could be made up again. And so growing up with a dad who is a drummer and a mom who was raised by an artist and just generally kind of West Coast transplant philosophy of, "What are we going to do next? What else is possible?" I came from this tradition and I'm going to somewhere with a blank page, what should we do and see? I was raised in that environment.

I went to an extremely diverse set of schools where oftentimes I was the minority in the classroom and I grew up in urban Los Angeles taking the bus and in the age of LimeWire and the internet coming online. And just I feel like my childhood, both through my parents and my physical and digital surroundings, was one of X exploration and what else can be and what else is possible? I just have always derived so much energy, appreciation and celebration of things that kind of challenge perceptions of what is possible.

And I think one of the things I found over time is that the things that inspire me the most are intersection points, kind of intersections between two things that were never intersected before. And I think honestly, though it's a trope, I think Steve Jobs did this fantastically. What happens if I intersect calligraphy with computers? I know that's an overused example, but I do think it's a good one. Or if you look at what Virgil Ablo did with fashion and streetwear and high fashion and which one is it and what is original and what is it copycat? And James Turrell, as you referenced, merging the idea of astronomy with architecture with interior design with perceptual psychology. I just love people that mash up these different things to make something new and change our perspective of things because of the way my parents raised me, because of where they raised me, because of my childhood. I think it's just something I've always been super fascinated by.

“And I think one of the things I found over time is that the things that inspire me the most are intersection points, kind of intersections between two things that were never intersected before.”

And so that carries through to The Browser Company where when we think about the software we make, I think we look toward inspiration from outside the technology world as much as from inside because the people that I've always looked up to and the people a lot of our people on our team have always looked up to are people that take inspiration from these kind of previously dissimilar places and say, "Wait, what happens when you smash them together? What comes out of it?" It's not always good, we do some weird things that don't always work out. But yeah.

MM: I love that. One of my favorite definitions of creativity is just connecting old ideas from unconventional places in new and interesting ways and it makes it much more straightforward too because then it's like, well it's not actually about knowing the most about a particular thing and trying to find the areas that haven't been touched yet, it's more about just going broader and sourcing inspiration from a lot of different places and then seeing what amalgamation can happen in mind.

JM: Yeah, the thing I think that I've always believed, and I mean it as being very empowering and inspiring, but I think a lot of people think I'm being critical when I say it, is the tech world and the world of people that make software for the internet tend to think it's really special and unique, as if like, "Wow, this has never happened before in human history." And I guess the short version of it is, I agree with what you're saying, which is there are some attributes of the internet and software and computers which are unparalleled and new, but I think things take different shapes and forms, but there are a lot of similar stories and dynamics that play out over history. And so that doesn't mean we shouldn't feel grateful for the time we were born and the place we were born and the opportunity to be at the forefront of things like the internet and now AI, it is really radically different and exciting.

But I also think there's as much to learn from what is not new and what has come before us, as you're saying, as there is to examine the new parts of these phenomena or inventions. And so I think if you believe that, it's super exciting cause it makes you want to dive into history books and read about other industries and read about people who came before you. And again, adopted and updated the new and the current context. But I tend to think, it sounds like you, that the stuff is old as much as it is new, and that's actually really exciting in terms of sources of inspiration and creativity and possibilities.

MM: And it means there's always more to learn too and that it humbles you to know that you can revisit history and see what has been learned about these same patterns before and not just have to reinvent the wheel every time. And I think that that takes a certain amount of almost humility too, of I'm actually not the knight in shining armor.

JM: Yeah, you see with Arc, some of our most people love celebrated product attributes and features and flows... And it's really awesome, it makes our day and week and they say things like, "Wow, look at what Browser Company is doing. Look at this thing in Arc. They're really pushing us forward." And I mean, I live for that, I love that so much. But the truth is a lot of these things are, "Oh, we just borrowed that from movie trailers. We've been doing that for decades. We didn't do anything new, we just actually did a cheap interpretation in many ways of this thing that's been happening for many decades in this other industry." So again, I find that very exciting. But yeah, I think it's as much old in a new light as it is truly new.

MM: Totally. What are some of the companies or people or things happening in technology right now that you think are, other than Browser Company, a good embodiment of this approach of making something old new in a new and interesting way?

JM: Notion for sure. I credit Ivan and that team with honestly rekindling my inspiration and joy of building software. Just there's a purity to what they've been doing and a relentlessness to what they've been doing and an originality to what they've been doing, but also a deep schooling and appreciation for those that came before them and the concepts that came before them, both within software and outside of software and a celebration of that, not hiding that. And so Notion definitely stands out for me.

I mean, it'd be remiss not to mention Apple, a hundred percent, a hundred percent. I can have my issues with the way that the company has grown and matured and different elements that are seeping into their product development process and product experience. But at the end of the day, there's probably no company, technology that has inspired me in the team more than Apple. So again, in many ways an easy answer but also a true answer.

And then I'd say the final one, which not so much anymore is Snapchat, was Snapchat. And I think Snapchat for the playfulness. I think again the way that it can be easy in a conversation like this even to get wrapped up in the seriousness and the philosophy of it all. And I'll never forget, for example, when Snapchat did this marketing campaign where they were coming out with their glasses, I forget what they call them, and they did a vending machine that was a big yellow vending machine that looked like a face and it floated out of the sky from balloons like the Pixar film Up, and it was just so playful you couldn't help but smile. Or I remember when the application first came out and it was yellow, not even a nice shade of yellow, a pretty brutal shade of yellow, like a children's hair salon and the little dancing ghost when you refreshed it, wasn't even a beautiful ghost, it's just a little dancing figurine. And it just made you smile and it was so not self-important and just gave off such a vibe.

And so as much as I cite Notion and Apple, I think those are in many ways very serious brands with very serious missions and mandates and very serious ways of talking about themselves. And I really like that intentionality and spirit and heart, but merged with the ethos, I think a little bit of Evan and Snapchat of, "Let's have fun with it, let's make you giggle, let's make you smile." And I think you can see elements of both in Browser Company and Arc, which are on one hand very aspirational, I think very principled, very bold, and at the same time just having fun with it and not always knowing if we're joking or not and we don't even know how serious we are at times.

And so I don't know if that's the right language, joking and seriousness, but I think, again, talking about merging intersection, I like the intersection of go for it, go for it, go for it, be pure, be principled, look to history, et cetera. And don't take yourself too seriously at the end of the day. Again, my dad's teaching, you're a speck of dust, have fun with it and feel something.

“I like the intersection of go for it, go for it, go for it, be pure, be principled, look to history, et cetera. And don't take yourself too seriously at the end of the day.”

MM: Love that answer. It's interesting too, I feel like Snapchat was a unique time in technology where they could be playful and remind people that, "Hey, technology can be something that is just for personal use, and you and your friends and just playing around." I wonder if Snapchat could have that attitude today, you know what I mean? If they were launched again, I almost think that maybe it would be misconstrued or something because technology is just seen in a different place in our lives and it's become much more ubiquitous. But I feel like Browser is a pretty unique embodiment of both the phase of technology where we're at of we want serious tools that really work and are high quality, but then we also, they don't need to be stodgy or gray and like, I don't know, the Adobe Suite or something like that feels heavy.

JM: Yeah, when I was in my-

MM: For advanced users.

JM: When I started the first company with Hursh, there was a really, really famous kind of media executive, traditional media executive I had the privilege of meeting and I can't even paraphrase it quite honestly, but essentially what he was saying is that the media industry goes back and forth on this pendulum and it just swings from one side to the next. And if you look at the media industry over decades just really consistently goes back and forth in this way. And I do think that applies in many ways to the technology industry as well. You obviously see that in fashion and in music where the next cohort or generation of thing, media company, product, fashion in many ways is a reaction to what came before it kind of refutes and reacts to what came before it.

And I think very similar, I think that applies to technology too. Again, if you think of it as a fashion in many ways or a cultural product, I think a software is a cultural product. I think that's one of the things I really believe is I've used software in the same vein as music or film or clothing. And so I think in that sense, you're absolutely right that could Snapchat do the same thing today and be as effective? No, because a lot has happened. And I think that's even what I was trying to allude to about Apple is Apple in the moment in my life that it inspired me and I think did its best work, it was perfect for that. Two decades later, we're still doing the same PowerPoint format in the presentations and it's starting to feel a little bit meh, and that's not a criticism of them, but I think I'm really inspired by the companies, the constantly and the products and the creators, they constantly kind of push to be a reaction to their old previous self in many ways.

And so to that point, yeah, no, I don't think Snapchat could do the exact same thing today because the fashion has changed, the culture has changed, society has changed, and whatever comes next will be a reaction to that in many ways.

MM: It reminds me of Stewart Brand’s culture cycles, like the different rings and the different speeds that they operate at. I feel like he needs to slot in, I think it has for technology, but software specifically, I feel like it's almost a different pace and it's more between almost fashion and technology's pace.

JM: And by the way, that is the intersection that we're really interested in, in that it's not fair to say to your point, it's truly just like fashion or music or film because those products really are cultural products that are trying to literally share a perspective or tell you something or make you feel certain way, elicit an emotional reaction, entertain you. That's not what a web browser trying to do. It is a tool at the end of the day. It is utilitarian, it does serve a purpose, it has jobs to be done. But at the same time, our view is what we are reaction to is this very utilitarian, maybe boring, maybe drab, maybe inhumane depending on who you are, conception of our interface in digital homes, which are, they all look the same, they all do the same things, they get out of the way, they have no opinion.

Kind of what we're saying is, wait, that's not right either. So we're interested in what if you kind of mash up those two, you intersect those two, what do you get? And I have no doubt if we are really successful, let's say we redo this podcast in five years and our grandest dreams come true, I bet people will start to feel like, "You know what? Will the nice software just chill out? Let's stop having so much personality." And so again, and I think that's an exciting thing. Yeah, I hope that we rise and reinvent ourself in that moment too, so I think the pendulum swings.

MM: Totally. That's great, I like that articulation a lot. Pivoting a little big, I'm just curious, if you could clone yourself so that you could pursue other things in other universes, what would you be pursuing?

JM: I love that question so much. I really want to make a public sculpture park. I think I would make parks in public spaces. I think in a different life maybe it would've been an urban... The only really good grades I got in college were urban design and urban planning classes. And my mom worked as a city employee and my godfather was a city planner and I just love, love physical public spaces. So I'm not sure how much money there is in that or what the job is, but if I could make something that wasn't software, it'd be a public sculpture park in an urban area.

MM: Similar between that and Browser is perhaps spaces to play in and places for people to do their things and express themselves and all of that.

JM: Lay in land and let your mind wander and meet a friend. So put it like this, if I make a bajillion dollars, Elon can take us to Mars and I want to make a really, really lovely park. That's my Mars, a bunch of parks.

“If I make a bajillion dollars, Elon can take us to Mars and I want to make a really, really lovely park. That's my Mars, a bunch of parks.”

MM: That's super great, I love that. Okay, cool. Again, maybe tracing back a little bit, I'm curious to dig deeper into your background because you spent a few years at Thrive and I'm curious how you navigated what you wanted to do next when you were thinking about becoming a founder or an investor, and yeah.

JM: Horribly. I think I navigated it horribly. I mean, obviously I don't mean that literally because I'm very proud of how it turned out and I loved my time at Thrive, but I guess when I say horribly, what I mean, and this maybe just applies to me, whenever I've tried to do something, as in I very intentionally and intellectually and rationally tried to figure something out about my career, it did not go well. And so I would say I joined Thrive initially as an entrepreneur in residence, which is the world's silliest title, but it was a really cool job, and the intention of that role was to take a year and start a new company or do something, figure out my life. And it didn't go well. And that's actually part of the reason I transitioned into being an investor there was, "Well, don't know what I'm going to do still and it's been a year, I should probably get on with it and these people are awesome and this seems really fun."

I think as soon as I let my guard down and didn't try to figure it all out, I figured it all out. And I think that's true, I can't speak for other people, that has been true across my life, personal life with love or it just is always true for me that I just need to get into that state of being relaxed and not so tense and wound up trying to, "Ph, I want to figure go to X, Y, and Z and do this," and just kind of go with the flow and trust in the serendipity of life, which again sounds overly romantic, but I really believe in.

So the best part about Thrive was actually the period after I gave up trying to figure out my professional life and gave into the idea that maybe I was not going to pour my heart and soul into work ever again, I was going to have a job that I had a lot of fun doing every day, and I worked with really talented people and I learned great things, but it didn't necessarily reflect my personal creation and wasn't an expressive medium, which work had been before that. And as soon as I embraced that and let go, I started finding inspiration all around me, again, seeing how, "Wow Robinhood realized that all the public companies that competes with make money off of charging for trades, if we give it away for free..." I found inspiration in all these places that I was never looking and never thought could be inspiring because I just kind of like, yeah, I don't know, went with the flow.

And so yeah, my time at Thrive went horribly in that at first I didn't get out of it what I wanted to get out of it, and quite frankly, I think felt pretty lost professionally even though I was privileged enough to feel lost at a place that paid really well and was a really interesting job. But I don't think I felt totally satisfied and content that I knew what I wanted to do professionally. And as soon as I got there and let go, it all turned out okay. So I'm very grateful for my time there. I learned a lot. Browser Company wouldn't have happened without it.

MM: Awesome. Tracing it back even a little bit further, you spent time with the White House, as you mentioned, as Obama's chief product officer, what do you think Silicon Valley can learn from politics?

JM: I'm not sure learn from politics as much as what my time in Washington taught me from the people that I had the privilege of learning from and getting exposed to was how little I actually knew about how everything in the world works, whether that is people in the United States and the way that they live and what their culture is like and what their day-to-day is like to I thought because I read The Economist on Sundays and the New York Times every day on my phone that I understood our government and political system. It was a very humbling experience for me around my ignorance quite frankly, which again, some may see that as a criticism or bad thing. That was very liberating for me because it kind of like re-stoked that curiosity and hunger.

And so I think Silicon Valley can learn a little bit of humility in many ways. I know you wouldn't think of politicians as being humble and they're not, but the humility of being around people of all shapes and sizes and expertise in an environment where you're just constantly learning about and talking about and working on these really big problems and different shapes and sizes is very humbling. And I think in that humbling is a kind of fire in the belly that comes and a drive to learn and the curiosity.

And then at least for me personally, one of the biggest experiences was if I think about my childhood, I think of logging onto AIM after school or getting my first phone that had games on it or my iMac or Limewire and the internet and how lucky the year I was born in 1990 and what that meant for my childhood and what I came up with. But I think because of that, I forgot that I'm not really a tech person and I don't think most people are tech people, and I think they forget that because it is at the kind of apex of our society economically, culturally, politically. And so there's this gravitational pull towards tech as this thing or this area where it's like now I've come to see it as this sort of horizontal layer across it all.

I think getting myself physically out of the tech world to Washington DC and surrounded by people with backgrounds and experiences and things to teach that were so different to me reminded me I'm not really tech person. I think tech and software and the internet computers, they're interesting tools or means to ends, but the ends that I actually get energized by, nothing to do with software. Just like no one would call themselves an electricity person, no one would identify that way. I think getting myself physically out of it and intellectually out of the tech world reminded me of that personally. And I think the tech world could get a lot if everyone in it thought, "Who am I really? What do I really care about?" And maybe that means I make an app or maybe that means I go on a Y Combinator find, but that's not really someone's identity, I don't think, or I don't think it leads to interesting things when it is.

MM: Why do you think the tech world is like that? Electricians probably aren't like, "I'm an electrician, I buy it, this is a lifestyle," and yet tech has this pervasive one size fits all model that people seem to readily adopt. Is it because there are a lot of young people? What are your thoughts there?

JM: What do you think it is?

MM: I'm not sure. I think it's mostly because a lot of people come at formative times in their life and they're looking for identity, searching for ideology to adopt, and they see people around them doing a certain thing that is prized of high status and they're like, "Well, I'm just going to emulate them." And then it becomes race to see who could be the most impressive in it's very specific dimension, which is productivity and creating value and all of these things, which is mostly incentivized by the venture capital model.

I'm not sure though, I think that there's more to it than that. I think it's also there is a certain sensation of technology, of progress and being at the forefront and the frontier and all of that. And I generally think that's pretty good in terms of actually creating outcomes and pushing things in a positive direction, but I think it might be bad on the individual level often for the people doing it, but good on the whole. It's like what's good for society and what's good for the individual is often different.

JM: First of all, I would read if you wrote about this or a New Yorker essay or whatever if anyone to write this, I hadn't really thought about it.

MM: Please.

JM: But I think if I were to add potential hypotheses on top of your fantastic ones, I'd say there is an optimistic and a cynical take. The optimistic take, which I felt in terms of what I think Washington DC can learn from tech, is there is a set of values and principles imbued in the tech world that I took for granted until I got there. For example, we sold our first company to Facebook, and when I arrived at Facebook, you really felt that it did not matter how old I was, it did not matter what my title was, if I had good ideas, I could manifest those good ideas and those ideas would be as impactful as I thought they could be, the sky was the limit. I could jump levels, I could jump comp, I could be heard, I could be listened to.

And to Zuckerberg's credit for all of his flaws, he created a culture where he, starting with him and everyone else, truly listened no matter who you were in what rank and how long you'd been in the industry. There's a speed at which people work and realize things, there's a level of ambition and audacity to dream. So I think we're in a moment culturally where it's easy, and I do this to kind of boo the tech world and point out its faults, it's a really special set of values and principles that we almost take for granted that I was reminded of when I went to DC. So the optimistic take is because it actually is that special. So the fact that the internet exists or computers exist may not be that anomalous relative to other transitions in the past and we may be too self-important, but I do think there's a cultural aspect to the tech world which is real and is special in many ways though it has second order consequences and are always good. And that has an alert to it.

“And to Zuckerberg's credit for all of his flaws, he created a culture where he, starting with him and everyone else, truly listened no matter who you were in what rank and how long you'd been in the industry. There's a speed at which people work and realize things, there's a level of ambition and audacity to dream.”

And I found myself going back there, I didn't go to a think tank after DC, right? I didn't change industries. I may have not served a company right away, but I went back to the place that dreams really big, moves really fast and celebrates people of all shapes and sizes at its best if they have something special to say. I think you're a great example of this. I'm thinking about our relationship and our background and all the amazing people that I'm sure on is going to be on this podcast with me. No one was like, I met you when you were student at UCLA, but there's this kind of part of the culture. And so that's the optimistic take.

I think the cynical take is it's where the power is and it's where the money is. And I wonder if you would say the same thing about the finance world in the 80s or the 90s. It's actually interesting if I think about college friends and friends of friends and parents of people I know that you could read about them on Wikipedia. They all started a hedge fund or a private equity, I don't even know how these things work or worked, I wonder if it's just, again, nothing is new, this isn't new, this is the power center, this is the money center, that's where people go and those people tend to think they're pretty special.

In the same way that I think I probably look too judgingly whenever I, "Oh, so and so's uncle is a billionaire. What did he do? Oh, he did leverage, buyout, whatever of whatever company." And I'm like, "What a waste of human potential and why does society reward them and make them billionaires when they don't even know...?" And I guarantee you, my son and his friends are going to say that about all these techy people who flipped a bunch of crypto assets.

So anyways, that's all to say the cynical take is there's nothing new to see here. This happened with finance, it happened to be industrialist before it, the power and the money. I think the truth is when I was younger, I definitely loved, and still actually to this day, people who know me the best tell me, I think too much in binaries. The truth is more nuanced and it's a spectrum. So I bet it's a little bit of both than some of the ones you've mentioned too. But those are my two best guesses, one optimistic, one cynical.

“So anyways, that's all to say the cynical take is there's nothing new to see here. This happened with finance, it happened to be industrialist before it, the power and the money.”

MM: I like that. And it's also probably a cycle. Again, it's like something that, we'll feel this way and then it'll go back to being optimistic or pessimistic.

JM: And this goes back to the intersection, the things that inspire me, I love anything that fucks it up. And sorry to curse, but I guess what I mean, I don't mean that in a negative way like burn it down or disrupt. I don't mean it like that, but just every time something new comes along and it's like, "Whoa," I love that feeling, just mixing it up. It's funny, my son has this book that, maybe it's on my mind, it's this book called Mix It Up, you're supposed to go mix it up. There's like one page that's blue paint, next page it's yellow paint and then your next page it's green because you mix it up. I like when we mix things up and I think, yeah, there'll be another transition soon. Yeah.

MM: Makes life interesting, makes the world more interesting. Yeah. Wonderful. Well that is all my questions. Thank you so much for coming on the podcast, Josh.

JM: Thanks for having me, Molly.

MM: It's been an absolute pleasure.

Subscribe for more episodes to come: Spotify, Apple, Google, Amazon, and Overcast.

Highlights:

• The best content is designed for the audience who will get the most impact out of the product — everything from the format, where it shows up, and what it’s trying to make people think and do. The most powerful and trustworthy content usually tells the stories of the people genuinely enjoying and making the most of the product.

• Some marketers are artists and others are scientists — but both should know what is grabbing and motivating the most audiences and be able to come up with creative solutions that capitalize on what people are responding to.

• Two marketing skills that will be increasingly valuable in the decade to come are 1) being willing to break the mold and 2) understanding an audience well enough to stay ahead of them and market to the way they make decisions.

MM: Hi everybody. Today I’m joined by Camille Ricketts, the former Head of Marketing at Notion. Previously Camille led content and marketing at First Round Capital, worked in digital services for the White House, and helped manage communications at Tesla.

Our conversation covered content marketing strategies, the unique skills needed by different kinds of marketers, and the areas of the field where humans are still needed. I hope you enjoy.

MM: Hello, Camille, and welcome to the podcast.

CR: Hi, Molly. Thank you so much for having me. I'm excited to be here.

MM: Amazing. My first question for you is how would you define the through line to your career? What threads have you kept pulling?

CR: Oh my gosh. It's a big question. And also one that becomes so much clearer in hindsight.

MM: Yes, absolutely.

CR: I would say that number one, writing. The ability to write something that you feel pretty good about pretty fast, I think, is an underestimated skill, and something that I got very lucky to build through being a journalist, starting from really early on, and then figuring out how that would translate to comms, and then marketing. But I do think knowing how stories are constructed and being just curious about new ways to tell stories has been something that's shown up in everything that I've done.

MM: That's wonderful. How have you seen that evolve throughout your career? Has it been something that you have noticed in the environment around you to be shifting? Or is it more something that you've dug deeper and discovered more historical examples that you've been inspired by?

CR: Oh, that's a great question. I think that, definitely looking historically and being a big reader, and I know that that is advice that is very commonly given to anybody who is excited about writing in whatever form factor or story creation, but truly cannot be over pronounced how valuable it is to see how other stories have been told throughout all remembered time. I think it's one of the reasons that I was a history major in college, even though there was no clear sense of what that was going to lead to professionally. Because history at its core was really about understanding stories about things that had actually happened.

But I think that the number one thing that's changed just during my career has been form factor. Just so many movements in that. Started out as a long-form feature journalist, obviously went deep with that at First Round Review, where we went into tactical storytelling, and often those pieces would be 3,000 to 8,000 words to really get to the essence of what was being relayed. But now, seeing how podcast and video, and shorter, and shorter form video are now being utilized to tell really robust stories and to really convey personality and lifestyle, I think all of that is so interesting. And so, I've really tried to just stay on the edge of what the audience is finding most engaging, depending on which audience you're speaking to.

MM: How do you think about differentiating content in a sea of all these different new content types and everyone is trying to find an edge? What is your secret sauce? You don't have to reveal it.

CR: Well, I think it's going to be not entirely non-obvious when I say it. But I also think that it's a step that can often be glossed over. But it really does start with figuring out who that person is, who you're trying to move with whatever content is you're trying to create. And I say, move because it could be moving them emotionally, it could be mobilizing them to take an action or obviously to make a purchase. Getting them to believe something in particular. So, having a really precise sense of who that person is, and I say, person and not people, because I think it can be a really helpful tool to actually distill it down into what that type of individual is like. And then, figuring out what it is you actually want them to do or how you want them to change. I think that all of those ways that you can move somebody comes down to what change do you want to make and how they think, or how they act, based on what you're telling them.

“I think that all of those ways that you can move somebody comes down to what change do you want to make and how they think, or how they act, based on what you're telling them.”

And so, doing as much thorough research as you possibly can, about not just what those people want, because I think that, oftentimes people don't know exactly what they want, and you end up with broad conclusions around they want to be entertained or they want to be helped in some way.

MM: Yeah.

CR: But focusing more on what they need. So, what are the things that they are actually missing in their lives? What are the things that are continually painful for them, or that they wish they had access to, but don't? Asking enough detailed and nuanced questions to get a sense of those things. I think that the differentiators that a lot of great content then rides on comes out of what gets exposed in those conversations. Yeah.

MM: How do you figure out who is the right person to focus on? Maybe less from a business and marketing perspective, but more, if you are thinking about marketing or reaching the people that you're trying to sell to or convince of something, how do you narrow in enough to get a clear definition of the... The version that will actually have the most impact in the long run, versus just like, "Oh, we have a bunch of different people and they all fall in this broad domain, but we're not really sure which one is going to actually drive the most in terms of just moving the needle for the company."

CR: Right. I think I will start from a business and marketing perspective, to get to some practical clarity. And then, we can romanticize it a little bit.

MM: Perfect.

CR: But, I think that it starts with who is going to understand what you're doing or be so excited about what you're doing so implicitly that they're easy to acquire. And when I say easy to acquire, that doesn't necessarily mean, "Oh, I got them into my funnel." Or, they made a purchase on the website. But, you were able to get them to adhere to whatever it is that you wanted them to do fairly easily and painlessly, because they just got it.

MM: Yeah. True believers.

CR: Yeah, true believers. And then, if you cross-index that with how... Valuable is too mercenary of a word. But how important or impactful those people are going to be for you over time. So whether they are going to be on this journey with you for a long time, whether they're going to get more, and more, and more out of the service, or product, or content you're providing to them. But if you think about, "Okay, who is the easiest to acquire?" Like we said, "Who's also going to get the most impact out of what we're doing and impact us the most?" Then I think you start honing in on who that individual is.

“But if you think about, ‘Okay, who is the easiest to acquire?’ Like we said, ‘Who's also going to get the most impact out of what we're doing and impact us the most?’”

MM: That's lovely. It reminds me of Notion investing in students and examples such as that.

CR: Yeah. Absolutely. And I think that people were always questioning that, because students, by and large... Whenever I would talk about all of our efforts in that direction, I would be told that they churn so fast and they represent no revenue over time.

MM: Right.

CR: But, when we realized how vocally and how enthusiastically they were carrying our message, it became a no-brainer to really invest in and support that audience.

MM: That's lovely.

CR: Yeah.

MM: What are some misconceptions that you think people hold about this type of marketing and really targeting a unique specific individual?

CR: I think that some people go in with wishful thinking about who that person is. Like, "Oh, if only this type of person would be our audience member."

MM: Yeah.

CR: We started out there when I was at First Round, it was really about prospective founders, and could the highest caliber prospective founders in the world raising seed funding be really engaged by the content that we were creating.

MM: Mm-hmm.

CR: I think that that's helpful to know what your ideal is, so that you can craft a strategy that potentially gets you there. But I think that you also have to be realistic about whether that is an audience that you can successfully speak to, with all of the resources and your current position in the market. And maybe it's several moves or a phased approach away. And so, you have to then, I think, be more practical about who that immediate audience is. So that's one misconception, is that, you can't go into it with like, "This is who we want to get and that's what we're going to do."

But rather, be a little bit more thoughtful about what is the most suitable for you in the present day. And then, I think that the other is not necessarily being open-minded enough about channel and form factor. I think, some folks, I've seen this quite a bit across startups, think about content almost entirely as writing. So like, "We're going to have a blog. That's the way that we're going to deliver this information." And there's no backtrack to, "Well, why are people going to come to this destination in order to discover more writing here?"

"Do the people that we want to have engaged with this have the time to read something like this?"

"Do they live somewhere else online or spend an inordinate amount of their time on a different channel that we should be exploiting?" So I think that making assumptions around what content looks like before really understanding that audience and designing for them specifically can be a costly misstep.

“I think that making assumptions around what content looks like before really understanding that audience and designing for them specifically can be a costly misstep.”

MM: Yeah. What companies have you been, or organizations more broadly, have you been inspired by their taking unconventional approaches to content and forming the form factor around who their audience actually is?

CR: I mean, I think that Figma has done just an incredible job with thinking through particularly how events and community can help them tell and amplify a story.

And knowing how designers like to interact with each other and learn from one another. And knowing that they didn't have to bear the burden of always producing content that tells their story, but equipping these community members with enough that they can then amplify it and carry the message on their own.

I think that that's really interesting. And something that we were certainly inspired by at Notion. And tried to do to a large degree as well. I'm trying to think if there's any others where I'm really excited by what they're doing. I mean, there are some that have really capitalized on TikTok and the social aspect of things. One that I've been so impressed by, and this is a really random one, is Duolingo.

I don't know if you call it Duolingo at all on TikTok.

MM: They do do an amazing job.

CR: But it's certainly because it is a consumer audience that they're trying to get excited to not only try the app, but then come back again, and again, and again.

They've really leveraged a specific type of humor in order to do that on TikTok. And I think that that's been far more effective... Or I imagine it's far more effective than writing articles about learning a language.

MM: It's not where their audience can be found most definitely.

CR: Yeah.

MM: Reminds me too, I feel like Browser company's doing an interesting thing with their YouTube videos and stuff like that

CR: They're doing an incredible job. And especially, exposure to the team.

So it's less like, "Oh, these are the people who are designated content creators on the team. But let's widen the aperture on who can tell the story."

And, Nate Parrott over there who's the engineer working on a lot of some of their cool stuff. He's such an incredible performer.

MM: Yeah. He's amazing.

CR: And they also are doing an incredible job building in public. And I think, leveraging content to make that story really clear.

MM: And it displays such an awareness of who their core audience base is, which is mostly people that really do care about craft details and the underlying just methodology of making good software too. And they are actually genuinely curious how decisions get made, and they're showing them out in the open, which is a very rare thing. And usually, it's seen more as a liability. But I think, for them, it really actually makes them much stronger.

CR: Yeah, I think that understanding that their audience is one that wants to be brought along on that journey.

MM: Yeah. Yeah. Totally.

CR: Right. And doesn't just want to be shipped to.

MM: 100%. At what point do you think that companies need to start thinking about content?

CR: Oh. It's different depending on what it is that you're trying to do. It's interesting. I was just in an advisory session this morning with a company that's going after pretty large enterprise clients from the very beginning. And in that case, I'm not sure that content marketing is actually going to be as valuable, particularly if you have very specific types of customers, as going after people very directly.

I do think that it becomes key when you have customers that you want to tell stories about. So I think that that's one of the first types of content that any company should think about pursuing, is, telling stories about people who are successfully using the product.

So whenever that becomes... Just resourcing that you have at your disposal, or some ingredient that you have. I think that putting those stories out there and making sure they're being told in the right way is important.

But increasingly, I think it's really important to pause and think through your own distribution, and whether you have a channel built up enough that the stuff that you create is going to find an audience. And if that's not the case, then I would say, you need to be cautious about overly investing in content. And are there things that you can do in advance of that around borrowing other people's audiences to get to the types of users you should be speaking to, whether that's going on podcasts, or being featured on substacks, or thinking through who the right partners could be to get you in front of those people. And at the same time being like, "Okay, well, if we were going to invest in one particular content channel, would it be social? Would it be a blog? Would it be our YouTube channel?" And, leaning in there, as opposed to taking a broad approach to like, "We should just be doing content, because that is a marketing lever that we've heard about before."

“Can you borrow from other people's audiences to get to the types of users you should be speaking to, whether that's going on podcasts or Substacks?”

Which, I think, is unfortunately a trap that some people fall into.

MM: A 100%. Are there any, in your opinion, underutilized metrics for success in this area? Because there's some more straightforward, "How many users are we actually acquiring through this channel, this content?" Whatever it is. But I'm curious if there's any more longer term metrics that you think are underutilized.

CR: Yeah. So at Notion, we have this metric, which speaks to what you just mentioned, which was blog influence signup. So, that meant if people clicked the signup button after being on a page that had some content on it, just so that we understood that pattern of consumption and signup.

I do think that looking at, and this is for many reasons, but net new visitors to your website and to your content. So how many people are out there who've never been there before who are discovering it, and magnetized enough to come see more? I think, that's really important. So you're understanding how content is aiding your brand awareness growth over time.

And then, the other one I would say is subscribers. So if you don't have a way of having people basically click a button that says, "I'm very interested in seeing more of this." Type of thing. Whether that's following type of content or subscribing to receive an email newsletter or something along those lines, I recommend building something like that in, because those are the people who I think are closer to the easily acquired folks.

And so, you get more of a signal on who they might be. But also, expands your marketable database of people who you could potentially go out to in different ways to try to mobilize them in different directions, whether that's inviting them to events, or sending them more material, or scoring them and sending them to your sales team to see if they should be reached out to in a different way. They are people who've opted into a longer-term relationship with you.

And I think you want to build that list over time.

MM: Would you define them as the potential true believers?

CR: I think that they get you closer. I wouldn't say that they necessarily all will be, because people come from all types of angles when they choose to click subscribe depends. Quick anecdote that I'll share there is at First Round Review, like I said, we were targeting folks who were going to be founders, and raise money, and be interested in potentially working with First Round. But it turned out that a huge swath of the audience that we saw, based on who was subscribing were people at Facebook, and Google, and Netflix. So, the FAANG companies. And we were so curious about why that was happening. And it was folks inside of those companies that were startup curious.

They were always on the cusp of thinking, "Maybe I go do that instead." And we were able to then send them more specific content or invite them into experiences that would meet them where they were, and help them make the decision to perhaps enter the startup ecosystem. So, I think when you do build a subscriber base like this, you're giving yourself that intel, that allows you to be more specific in your marketing approach.

MM: You were serving them entrepreneurship propaganda. I love it.

CR: Exactly. So great. Yeah.

MM: Pivoting a little bit to think more about the people actually doing this work. I'm curious, what you look for in a person when you're looking to hire for a content marketer role or something of the like? What are the qualities that you think are core? And then, which ones can be complimentary and interesting in different ways?

CR: I think that the profile has changed a little bit. Had you asked me this five years ago, I think I would've really emphasized someone who is an incredible writer, somebody who is not just good at compiling the information but has a certain amount of musicality to their writing.

MM: I like that.

CR: And, has a sense of how words need to snap together. And I still think that that is an incredible skillset. And so important, and such a gift, and such an asset. I think that it's an increasingly rare skill to have cultivated. So for anyone out there listening to this who wants to be a content creator, I still think it's worthwhile to build those competencies.

But I think increasingly looking for people who are going to be on the edge of what is grabbing and motivating the most audiences. So, folks who are really in tune with what people are responding to and are able to be creative based on what they're observing in the market.

“I think increasingly looking for people who are going to be on the edge of what is grabbing and motivating the most audiences. So, folks who are really in tune with what people are responding to and are able to be creative based on what they're observing in the market.”

So being able to synthesize a lot of different types of data around what people are watching, what people are responding to, what people make purchases based on. For lack of a better description of this, but understanding the meme-ification of some things.

Not just what memes are popular now, but how memes even originates, and the life of them?

MM: Make something memetic too. Yeah. If someone is able to analyze that, it's such an incredible gift. Yeah.

CR: Absolutely. And then, they're able to construct their own, I think as a result.

MM: Completely. Yes.

CR: Yeah. That's what I would-

MM: Reverse engineer.

CR: ... Yeah. And then, complimentary. I mean, I think that you want to pair people who have a little bit of both of those things. So somebody who is a really amazing storyteller and writing with somebody who is a wonderful visual storyteller. If you do have the ability to synthesize those talents, you can end up with some really magical stuff.

MM: How do you think the role will change and what skills will be required increasingly in the decade to come, or even five years to come?

CR: I do think that there is... And this is what we're seeing with the move towards social commerce. But people who are particularly good at equipping others with story, and amplifying through folks who are specifically chosen and very intentionally partnered with.

So I think, Notion has this truly incredible influencer marketing manager named Lexi Barnhorn. And I think that she is an archetype of someone who I see being the prototypical excellent content creator in the future. Not only is she able to produce her own work, but she also knows who out there in the zeitgeist and the ecosystem she wants to pull in. And then, what information to give them or what access to give them, so that they are able to convey what the company wants to convey on its behalf.

Because, I think over time, we've seen this, where first we had digital advertising as the first wave, and then content marketing emerged, because folks realized that there needed to be a more consultative approach, rather than just advertising. There needed to be more argument around whatever it was that you wanted to sell or get people to do.

And now, I think that type of movement is giving way to, "I don't want to hear that from the company. I want to hear that from the people benefiting from the company."

"I want to hear that from people who have truly used the product and who I can trust on that basis." And so, being a content person who is able to orchestrate that type of feeling, I think is going to be really interesting.

“I think that type of movement is giving way to, ‘I don't want to hear that from the company. I want to hear that from the people benefiting from the company. I want to hear from people who have used the product and who I can trust on that basis.’”

MM: Yeah. It reminds me, it seems like a broad shift from very generalist content to more and more specific. And now, people are looking for... They want to see someone like them, basically.

CR: Yes. Yes.

MM: Showing them exactly how it could be used. And, it's interesting too. Yeah, it feels like the job is, like you said, increasingly one of being partially a talent scout, as well of, finding the people that are really spiky in particular dimensions that you know will resonate with other people like them. And then bringing them in, and giving them just enough to make that spike really appealing in a way that benefits your company.

CR: Yeah.

MM: And that's super interesting and cool too. It means that, it becomes a small town of true believers in a bunch of different ways.

CR: Yeah. And I think that then the responsibility for the person who is doing this is to make all of those people feel increasingly connected to what it is they're doing.

And continuing to get them excited about what's new. And that is a non-trivial skillset and amount of time invested.

Particularly all the research, and then I'll stop rambling about this. I could talk about this all day. But I think-

MM: No, I love it.

CR: ... One of the primary strengths of that strategy is that you can do it internationally, and there's so many companies now that are international or global by default, just because they're self-served, and the internet has no borders, and so people across the world are discovering what it is you're doing, but your marketing team probably can't be talking to all those people all the time.

And if you do have the ability to bring in this village, like you said, of folks on a global scale, then you are able to have a voice in all of these markets that are really interesting, even when you have limited resources yourself.

MM: Yep. Decentralized.

CR: Yeah. But that requires a lot of care, and a lot of research, and a lot of figuring out who the best partners are going to be in all of those places.

MM: Totally. And building trust with them too. Getting them excited, being cheerleaders, but also making sure... Because you're setting them loose to a certain extent, versus the older company doctrine needs to be much more control the narrative. You want it always to be from you. Exactly your PR person should dictate the press releases. And now, it's much more like, "No, actually, we want to hear the authentic versions of the stories of people actually enjoying our thing. And have them just to continue to do it out of their actual real genuine passion for the thing as opposed to us paying them or dictating line by line."

CR: Absolutely. Or being so precious about your trademark, your verbiage, your brand, look, and feel even. It'd be very tough to find a company that takes its brand look and feel more seriously than Notion does.

It's obviously an aesthetic now, that is not just an aesthetic, but a movement. Huge kudos to everybody who's worked on that. But part of what we had to get comfortable with on our influencer strategy were people talking about us in all different ways through all different types of aesthetics. And knowing that the meta-message that all of that was rolling up to was one of just huge global love and passion for this thing.

And that was more important than everything looking just so.

MM: Yep. Reminds me of a fractal of, they'll get different things out of it, and you just have to let them enjoy those little reflections that come off of it.

CR: Yeah. If you're like, "That's not a shade of green." We would've necessarily-

MM: Yeah. How do you think about how strong a brand needs to be in order for that to feel more comfortable and for people to have their own interpretations? Is it putting a very strong stake in the ground? Is there guidelines that you should evolve over time? How have you thought about it?

CR: ... Yeah, I mean, ideally, you have a brand where its identity feels fairly memorable and fairly distinct. That can be hard to do, but I think it is worth iterating on until you feel like you've gotten close to it.

Just because you want people to, when they encounter you out in the world, have an immediate shorthand response to what it is that you're doing.

I know that that's very difficult for early and young companies in particular. For them, I say, get as close as you possibly can to something you love in that way, and then just be as repetitious as you possibly can.

Just be out there constantly the same way, consistently, all of the time. But I don't think that you should worry necessarily about losing your identity as long as you equip these types of partners, these types of influencers with just certain, still pretty flexible, high latitude brand guidelines. So, obviously, you want them to use the same consistent name. You would want to equip them with your branding and make it clear that they can't alter it in certain ways. But truly, when we did it, it was a one or two pager of like, "Please don't do these things."

"But for the most part, have at it.” So, like I said, that balance of like, "Okay. What's really important for people to actually see this thing and then come to our website without any confusion?"

And then, what can we give people that type of flexibility on that they can really be expressive on their own?

MM: I feel like they have some ownership in it. Yeah.

CR: Yeah. Yeah, exactly.

MM: I love the quote that, "A brand is a promise that you keep over time." I think that's very true. Yeah.

CR: Truly, yes. And the consistency, I think, is what lives at the heart of that.

That you just have to show up the same way, not just visually, but in how fast you respond to people, and how informative you are, all of those qualities.

MM: And that's what builds the trust too. Yeah.

CR: Yeah. Yeah, absolutely.

MM: A slightly different question, but I'm curious, how does the role of being a content marketer and just a marketer more broadly that is a little bit more able to flex in different directions, change across the different cycles of a company's lifecycle?

CR: That's interesting. I mean, I think about it in terms of order of operations of what you really need to be doing at any given time over the course of a company's life. And it'll be different depending on whether you're B2C forever, or if you start out B2C, much like Notion did, and then move into the enterprise, or if you're pure enterprise at the beginning. But I think, most companies, regardless of which path they're taking, there need to start with really strong product marketing.

So, being able to invest the revs in all of that user research so that you do know what these people actually want, and need, and what pains you're killing for them, and what gains you're enabling for them, and how your product actually meets them on all of those frontiers.

And then, being able to describe that on a website, let's say. Because I think the website is your home base for being able to get people to make any decisions. So, making sure that your story is really strong in that arena is so important. And, product marketing, positioning work, all of that, it has to start there. And then, has to articulate these value propositions that are actually hitting people where you need to hit them for them to make a decision. So that's one thing, I think. And content marketers, I think, can very easily flex in a product marketing direction.

Because a lot of them are natural researchers, and certainly strong writing skills, and being able to put things into words is the core competency there. So I've seen that like, "Oh, I'm both content and product marketing." Inside of the same individual quite a bit. And then I think, you move into, over time, the sense of scale. So, what are the one to many mechanisms for telling your story? And that's where we go back to what we were talking about before, where it's like, "Oh, what channels are going to actually get in front of the right people all of the time?" What types of content, what types of forms of content are they really going to be moved by? And that's where, I think, content marketers who are a little bit more versatile in how they think about media can be really, really instrumental. And then, if you are operating in the enterprise, I think, then it becomes about repeatable growth and demand generation, and being able to have these more detailed, nuanced conversations with the right types of customers.

And then you see mechanisms, webinars, and that type of thing, lead magnets becoming a little bit more popular, where it's like, "Oh, we created a data report about our particular area of operation. But you need to enter your email so you can download the data report. And then, we're going to use that list of emails to send to sales to see if there's anybody that they should reach out to." That becomes much more of the direction, I think.

MM: That definitely makes sense. What advice have you given to young marketers early in their careers about developing core competencies and figuring out where their little niche is?

CR: Yeah, I think that marketing is such a horizontal discipline. You really, truly do have some people who feel more like artists and some people who feel more like scientists. And knowing where you spike on that continuum is really helpful. And then, surrounding yourself with complimentary people, I think, becomes a big part of the skillset, and being a really excellent partner to the people who are a little bit more your other half in that respect.

“Marketing is such a horizontal discipline. You have some people who feel more like artists and some people who feel more like scientists — knowing where you spike on that continuum is helpful.”

That's something that I definitely spent a lot of time thinking about. And then, I think that you can choose to become industry best world-class in a very specific area. So I do have friends who are some of the best editorial leaders across technology, and that's really where they wanted to go. And they've been able to build toward those moments. And then, there are folks who want to turn that type of trajectory into being a marketing leader. So, being head of marketing, eventually VP, eventually CMO.

And I think for those folks who do want to get on that particular track, gaining the product marketing skillset and spinning your emphasis on content into understanding more of the specifics of that discipline can help you up on that springboard much. I think, product managers become proto-CEOs. A lot of PMs then go on to found their own companies, because they've run a mini organization inside of a company before.

Or they've been responsible for a product. I think that PMs similarly are the ones who assemble a lot of threads across a marketing organization, in order to launch things that feel unified and coherent. Or, who are able to, I think, work across the folks who are owning other areas of marketing and bring them into a united effort. So, they become, I think, the most natural marketing executives at a certain point.

MM: How do you think that the world of marketing and the roles required of it are going to change in the next 5 to 10 years? Other than the content forms. What about the more job duties and things of that sort?

CR: I mean, I think AI is going to shake this up in major ways that it's really hard to-

MM: To comprehend. Yeah.

CR: ... Yeah. Yeah. One thing that I hope doesn't happen is that AI can be used to replicate a lot of the work that gets done in one's early career as a marketer. So, when you're still learning to be an exceptional writer, or still learning how to generate non-obvious, really incisive content.

I do worry that AI is getting better and better at doing that type of work. And so, are we going to allow people to still grow throughout their careers into people who can do things that feel very, very unique? Because I think there's still going to be massive demand for that. So I think that those paths are going to change. I don't know how. But I do hope that there's still opportunities for people. And then I think, honestly, being able to prompt things really expertly, based on human understanding. The human understanding side of marketing is going to be so key.

So I know that there are already products in the work where you're going to be able to, in natural language, say something like, "I need a landing page that's going to really hit on these value propositions for this particular audience." And AI will generate the whole thing for you.

What I think it won't be able to do is get to that degree of understanding about an audience, where you're able to stay ahead of them and market to the way that human beings make decisions, as opposed to what is already known, which I think is what AI is really good at bringing together.

“What I think [AI] won't be able to do is get to that degree of understanding about an audience where you're able to stay ahead of them and market to the way that human beings make decisions, as opposed to what is already known, which I think is what AI is really good at bringing together.”

MM: So it's the people at the frontier.

CR: Yeah.

MM: Hit again. Yeah.

CR: I think people at the frontier, and then people who are just really curious about people. Who really still want to be part user researchers, part storytellers. And, I think that AI is going to kick out just a bunch of stuff that sounds the same.

That follows similar patterns, and it's going to become even more pronounced over the next several years. So pattern breakers. I think people who are going to be pattern breakers are going to be very needed in this industry.

“People who are going to be pattern breakers will continue to be very needed in this industry.”

MM: Yeah. It reminds me too of because there’s more and more founders, just really the people understanding the relationships and breaking the norm in some interesting way. And that leads me to, I'm just curious, what are some of the common mistakes that you see early stage founders making with marketing?

CR: I think, not staying in it themselves long enough is one thing to really understand the story implicitly themselves. It's not something that can really be outsourced.

And I've seen this increasingly that there's this movement or understanding that, founders should stick with founder-led marketing and sales as long as possible, versus hiring somebody to just do it over there, while they figure out the product.

I think that that's really, really important. And it also prevents you from falling into this mindset of, "Oh, if the product is good enough, then it's going to really sell itself. And marketing is just here to maybe pour lighter fluid on it."

But rather, a deeper respect for what it is that marketing can do when it's really invested in.

I think that those are some key things that founders can pay attention to. And then also, not opting into growth too fast before they feel like they've really nailed their positioning and their messaging. I think that there can be so much pressure, so much urgency, so much impetus to be like, "No, we have to acquire users, so I'm going to hire a growth-oriented marketer."

But that person can only work as much magic as your story and foundation is going to enable for them. And then, it can often feel like a misfire, like, "Oh, we hired the wrong person." Even though, that person had very limited ingredients to work with.

MM: So do you think that, founders should be working on the story of the company and defining that magic thing that converts people from the very beginning? When should they make this a top priority?

CR: I think immediately, honestly. Truly, positioning should be one of the tools in your toolbox that even vets whether you're building the right product.

It's not exclusively about how you're going to talk about it, which I think a lot of people think positioning is about, where it's like, "Oh, well, that's the stem cell that becomes our marketing messaging." But I think it's deeper than that, and it's like, "Oh, are we actually building something that people are going to want, and need, and pay for?”

And, if you don't start with that germ of a story, I think, you're going to choose the wrong features to build even over time. So I think immediately, as you're even building the deck that you're going to use to raise your initial round or even tell anybody about what it is you're doing, is that positioning strong enough across all of these areas that you feel like.

MM: How do you test that? How do you get feedback on whether the story is strong and all that? Obviously, there's market demand, but I'm curious if there are other ways that you think are good at introducing a little bit more interestingness and not just a, "Will they buy or not?" More, is this subjectively interesting?

CR: Right. Yeah. I mean, I think you need to ask people who have no skin in the game for you. Right?

MM: That's great.

CR: Go to people who they don't think have skin in the game, but human beings generally to support and be positive with each other, it's just human-

MM: They do. Yes.

CR: ... So whenever anybody is asked for feedback, I think that the human brain just reaches for, "What is the most positive thing that I can say? Because I don't want to hurt this person's feelings."

MM: True.

CR: So not only do you have to find people who have limited skin in your particular game. But, I think you also need to prompt them with setting the scene with like, "Hey, I actually want this to be ragged. I want this to be-

MM: Yeah. Please.

CR: ... "Hard and Varnished. And for you to help me identify edge cases. Be really brutal on whether or not this is a true need.”

I think most people who are listening to this probably have heard the vitamin versus painkiller dichotomy. But, are you building a product that makes life slightly nicer for people? Are you building a product that addresses a genuine problem that people really need solved? And so, asking people, ideally people who you would want to have want this product, who have no need to be nice to you, or sugarcoat things, and be like, "Hey, let me tell you this story. And then, you tell me where there are holes in this."

“Asking people who you would want to have want this product and who have no need to be nice to you, ‘Hey, let me tell you this story and you tell me where the holes are.’”

MM: I like that a lot. Yeah.

CR: Yeah.

MM: Aspirational people too. Yeah.

CR: Aspirational people. Where it's like, "I would really, really want this person to want it."

MM: Totally. Yeah.

CR: And if they're like, "Oh, yeah, I would use it, but I would never pay for it."

MM: It's probably time to go back to the page.

CR: It's time to go back to the drawing board. And that happens so often. And then, I see MVPs being built, where people are going to use it, but as soon as pricing gets introduced there will be a huge drop-off.

MM: Yeah. Definitely. Ghosting.

CR: Yeah.

MM: Yeah. Wonderful. My last question for you, CR, is, I'm just curious, what has been inspiring you lately? Or who do you learn the most from these days?

CR: Oh, gosh. I mean, I'm very engaged with media in general. So, I think people in my life know that I watch all of the movies and all of the TV. I am incredibly inspired by A24.

MM: They are great. Yes.

CR: And I think, not just as a media story, but a brand story, where it used to be that you would go watch a movie for a particular actor, or because the story seemed compelling, and you would be like, oh, incidentally, that's this type of studio's movie. But now people are seeing movies because it's an A24 movie, which has really flipped the script on the entire industry to a certain extent. And I think that they've done that through a lot of what we were talking about around really distinct identity, having a very specific and nuanced point of view on who their audience is.

And what an A24 movie represents, or stands for, or looks like. And then, it's just repeated super consistently.

MM: They've built a credential. If you see the A24 logo, it's a proof point that it's going to be good in a specific and interesting way that you're familiar with, but they'll probably do a weird new spin on it. And they're always pushing the bounds a little bit.

CR: Yeah.

MM: And there's something about that brand promise that they're going to keep making things a little bit weird, but it'll be in a way that feels familiar, I feel like is very appealing actually, and exactly what the movie industry didn't have for a very long time.

CR: Yeah. And I think, one of the most interesting insights there too, is that A24 movies are not for everyone.

MM: Totally.

CR: They're not trying to be broadly popularized. And I think especially in the ecosystem of film and television that exists right now, where it's a lot of superhero movies that are supposed to appeal to the greatest number of people, having that narrower aperture has been their superpower. So for any folks who are like, "Well, what can I actually learn from A24?" Just not feeling like you have to be for everyone in order to be successful.

MM: Totally. Yeah.

CR: Yeah.

MM: I'm really inspired by also how they were really quiet for a really long time at the beginning. They were not trying to become the next new success story on the pages of every paper. They were much more just like, "We're just going to prove through the quality of our output over time that we are doing something interesting, and weird, and different, and then let it grow in the right directions because of the stories, not because of us in the way we're talking about it." It was a very show-not-tell demonstration, which I think was very powerful.

CR: Yeah. I couldn't agree more. So, they are the number one brand I'm looking to right now, where I'm thinking, "How did they do that?" And wanting to be-

MM: Truly. Yeah.

CR:... Yeah. Wonderful.

MM: Well, wonderful. Do you have any parting words for the audience, CR, of things that you are looking forward to, or people should check out?

CR: I mean, I think I'll just say that right now is... Much like people are saying how right now because of just the market conditions, or what's going on with AI, it's such a good time to start a company, because there's so many ingredients to pull on. And also, there's just a lot of auspicious factors going on in the market for brand new things.

MM: Yeah.

CR: And I think that that's true of content as well. That there is this clean slate feeling of, people being really responsive to brand-new, very odd, bizarre, and risky, and surprising, and bold things. And so, it's the perfect time to do something that you feel like is different, and challenging, and new.

MM: I love that.

CR: Yeah.

MM: Wonderful message.

CR: I hope so.

MM: Yeah.

CR: So good luck to everybody out there. Storytelling is such a beautiful art form. And I can't wait to see more of what folks produce.

MM: Me as well. Well, lovely. Thank you so much, Camille, for coming on the podcast. It was a delight.

CR: Thank you so much Molly for having me.

Subscribe for more episodes to come: Spotify, Apple, Google, Amazon, and Overcast.

Highlights:

• Cultures of entrepreneurship are created when the social currency is based on how ambitious your attempts at creating new businesses are as opposed to what credentials you’ve collected. Lowering the social friction to test an idea for a business and making it easier to stop working on it helps expedite the entrepreneurial process of narrowing in on a company-shaped idea that works.

• The internet is the ultimate amplifier of extreme outcomes (variance) because it takes something that might have been observed or participated in by a few hundred/thousand people and makes it potentially accessible to billions of people.

• ARIA is a bet that a new organization with a very different structure and a far greater risk appetite baked into the legislation can help re-accelerate science.

MM: Hi everybody. Today I’m joined by Matt Clifford, the co-founder and CEO of Entrepreneur First, the Chair of ARIA, the UK’s Advanced Research and Invention Agency, and the co-author of the book, How to Be a Founder. 

Our conversation covered the characteristics that define cultures of entrepreneurship, the goals of his work on ARIA, and how the internet functions as a variance amplifier. I hope you enjoy.

MM: Hello Matt and welcome to the podcast.

MC: Thanks so much for having me, Molly.

MM: By way of introduction, my first question for you is, you say that the internet is variance amplifying. Say more about what that means.

MC: Yeah. Well I think the way to think about what it means for the internet to be variance amplifying is probably to step back and say how do we get to the point where there wasn't that much variance to begin with? My sort of basic thesis about the world is something like the world was very, very weird for a long time. Then modernity came along and the main impact of modernity for a couple of hundred of years was to reduce variants. I'll explain what I mean by that for a minute.

And then the internet came along and it just threw a massive bomb in that and we're back to a world of extreme variance amplification. So what do I mean by variants? Well, I basically mean how extreme would you expect the outcome of any given social or economic process to be? And I think we've kind of got used to the idea that we have a set of institutions, certainly in the sort of democratic west as where you and I live, that damper variants, like the way we pick leaders.

Again, sort of if you ignore the last 10 years, it was sort of designed to pick the boring candidates. It was designed to pick the people that would do what the system expected. If you look at what our corporate leaders looked like 20 or 30 years ago, they were sort of satisfying the median desire of Wall Street analysts or the media or whatever, and that was normal because, in general, for most of human history, variance was a pretty dangerous thing. Variance is the thing you try and avoid. Variance is what kills you. And so, modernity did a great job of dampening variance. A lot of the institutions we love dampen variance.

What the internet does is it basically does the opposite. It basically amplifies the most extreme outcomes and a lot of your listeners will be familiar with this idea of it's called the Matthew Effect which sometime is called the rich get richer or where basically anything that attracts some sort of resource like attentional money then attracts more resource like attentional money. The internet just does that on steroids.

“The internet is the ultimate amplifier of extreme outcomes because it takes something that might have been seen or observed or participated in by a few hundred or a few thousand people and makes it potentially accessible to hundreds of millions of billions of people and that increases its variance a lot.”

The internet is the ultimate amplifier of extreme outcomes because it takes something that might have been seen or observed or participated in by a few hundred or a few thousand people and makes it potentially accessible to hundreds of millions of billions of people and that increases its variance a lot.

MM: That's really interesting. I love that description of it. It's also a good articulation of what a power law outcome looks like in the world when it's applied to everything. How does this change in the age of AI specifically — do you think it'll become more pronounced in the future or do you think it will even out over time?

MC: Well, I think one of the most exciting, some would say, terrifying things about where we sit right now, we're recording this in June 2023, is I think what the future of AI looks like is really up for grabs right now. And there are many different ways I think it could end up. But to paint sort of two, maybe not extremes, but two poles of what could happen. I think you can imagine a world where AI ends up being this very centralizing force where we end up with one big AI to paint very crudely. And it turns out that the returns to scale are so huge or the returns to getting to something like AGI first is so enormous that effectively you have one AI that is this the sort of dominant factor in the world.

Now I would see that probably ends up being variance dampening for reasons we can get into. I think there's another world where actually you see a lot of what's happening in open source right now, big very large language models being released in open source. You see a proliferation of innovation in that space. You see actually the compute needs for those models which are not fully competitive with say GTP 4, but pretty competitive with GTP 3.5. The compute cost of that is actually really low now. You don't need a huge compute and cluster to train one of those models.

You can imagine a world if that becomes the norm where there are millions or billions of different AIs, all of which are powerful, but there's not that centralizing force. If that world comes to fruition, I think that's a massive variance amplification because then when core insights are discovered, one, you'd expect that to happen in a very distributed way. It's not going to be limited to a small number of biddable people that can be hemmed in by regulation or other social forces. Then, I think, you get a massive explosion of variance amplification.

And to be clear, I should have said this in the answer to the first question, variance itself is neutral. I don't think by itself you can tell which of those is good or bad, except that I would say, you can imagine in the case of a world with a billion AIs, if bad things happen, they could get bad really, really quickly. Clearly, the opposite is also true. Maybe that's one of the best ways to material abundance.

MM: I like that a lot. That's a good answer. What is your take and how do you think about the question of is the rate of progress slowing down?

MC: I think that there are certainly domains that you can point to where pretty unambiguously to me the rate of progress is slowing down or at least when you adjust for the amount of input, the number of people working in them, the amount of capital going into them to pick two, one of which I know something about, one of which I know really nothing about. So I think it's pretty clear that the rate of progress in science adjusted for capital and people is slowing.

It takes more people and more money to get to breakthrough ideas today than it did a few decades ago. And we can talk a little bit about that. That's an area I know a bit about because I'm the chair of this thing called ARIA, which is a UK brand new R&D funding agency that's been given the mandate to try and solve that problem or at least contribute solving that problem.

I think the other one that comes up a lot, at least on Twitter, at least in the circles I hang out with, is it's sort of weird how hard it is to build things today. And if you measure progress, at least in part by the sort of physical assets that we have at our disposal and the ability to make ambitious things that are made of atoms not bits, I think, it's very clear that that has slowed our ability to do that quickly has slowed.

Our mutual friend Patrick Collison has that great page on his website, which I think is just patrickcollison.com/fast, where he just points out a long list of things that physical assets that were built in the past in what today seems ludicrously short periods of time. And we just don't do that today. And that I see as the opposite of progress I suppose. Yeah.

MM: Speaking of ARIA, I'm curious, what was the genesis of your being involved in the mission behind it and what problems are you trying to solve?

MC: Yeah, so ARIA came out of a desire from various people in UK government over the last few years to really look at this question of, is science slowing down? Is the rate of scientific progress slowing down? And if so, what are some of the institutional arrangements that might be able to fix that? Now clearly, one hypothesis is, as you sort of already hinted at, maybe we just used up the low-hanging fruit, maybe it will slow down.

“ARIA is a bet that says that there is something about the institutional apparatus of funding science and the way this happens today that is responsible for this slowdown. By giving a new organization a very different structure and a lot of freedoms, can you create a beacon for what it might look like to re-accelerate science?”

ARIA is a bet that says that there is something about the institutional apparatus of funding science and the way this happens today that is responsible for this slowdown. By giving a new organization a very different structure and a lot of freedoms, which I can talk about because obviously ARIA is small, it's not going to reverse the whole thing, but can you create a beacon for what it might look like to re-accelerate science?

And so, ARIA was set up by Act of Parliament in 2022, just over a year ago, and I always tell people who are considering applying for jobs at ARIA that they should actually read the act because although I would never recommend people read grammar just incredibly short, and this is sort of the beauty of our, IT basically says ARIA exists to fund breakthroughs, scientific breakthroughs for the UK and the world and it can do more or less anything that isn't otherwise illegal in order to get there. So it can do funding, it can do investments, it can do grants, it can do prizes, it can do really anything. It has relative, I should say it's fully funded by governments entirely. A public sector organization has 800 million pounds, which is what, just over a billion dollars I guess. And unlike most public sector organizations, ARIA has the freedom to hire who it wants and pay them what it wants.

“One of the things that I think people who work outside government often miss is that because of the way accountability works in government, if you don't have things like a risk appetite baked into the legislation, then you risk your success being evaluated in the same way that people would evaluate how you would build a bridge. I’d argue that the way you want to approach building a bridge and the way you want to approach funding breakthrough R&D should have a very different risk appetite.”

It can procure in ways that would normally be outside the way that the public sector, at least in the UK procures, it has an explicit risk appetite baked into that act of parliament that says it has to do high-risk things. And these sound like very, maybe particularly from people from Silicon Valley, listen to this be like, these are pretty table stakes stuff. But one of the things that I think people who work outside government often miss is that because of the way accountability works in government, if you don't have things like a risk appetite baked into the legislation, then when you are asked to account in some years in the future for what you did, the risk is that you are evaluated in the same way that people would evaluate how you would build a bridge. And I would argue that the way you want to approach building a bridge and the way you want to approach funding breakthrough R&D should have a very different risk appetite.

So even just little things like saying in the legislation, the point is to make high-risk bets that may not work in pursuit of enormous outcomes, that provides a degree of protection for the executive team of ARIA to really go all in on what they think might work. So sorry, there's a risk of becoming a long answer, but broadly, this legislation was passed last year. I was appointed to be the chair last summer alongside an amazing guy who's our CEO called Ilan Gur, who's executive leadership of the organization. My job is to, I suppose, do the governance but also do the communication back into government to stop any concern from government that they should be getting more stuck into what ARIA does. And broadly what ARIA will do is two things. One, it will fund hopefully breakthrough science and technology through a mechanism not unlike DARPA in the US.

So I don't know if I should say have, we are in the process of hiring program directors who are themselves really talented scientists who otherwise would be leading research themselves and what their role is to take some of this budget and actually come up with a vision of a technology or a capability that they think is on the cusp of being possible. They imagine what it takes to drag that into the present by funding people across science all the way through to engineering to work together to bring it into reality so they're not building a startup. This is stuff that's typically going to be like a decade pre-commercial, but they're bringing a lot of startup mentality to that activity. And what they're trying to do is say, if this were possible, who would I fund and how to make it happen? And so, we're probably going to have sort of 6 to 10 of these programs going, all of which have to be ambitious enough that if they're the only one that succeeds off that portfolio, it's still worth having done the whole thing.

MM: Truly very similar to startups. Yes.

MC: Right, exactly. And I think I have to say credit or maybe premature, but credit to the UK government that they really were willing to recruit people into these two roles, the chair and the CEO, that had a very different ... I have a very different background from the people that typically fund R&D funding bodies in the uk. And I think Ilan has quite a difficult different background as well. He's an entrepreneur, he is a very accomplished scientist, but he is also a deep tech entrepreneur and a founder of deep tech entrepreneurs. And it was a bet on taking quite a different mentality about how you might do this thing and applying it to a core problem in science. And it's very early days, I don't think we can, it will be years before we know if it's really paid off. But I would say the thing I have been paying closest attention to so far is what is the caliber of people we are attracting to our team who want to be part of this? And so far on that, I feel like in terms of talent density, we're in a really exciting place.

MM: That's amazing. Going back to the core problem that ARIA is trying to solve, if you could change anything about the existing institutions that are funding science, aka academia, what would you change?

MC: Yeah. So I think when I step back and I think, what have I learned about talent and outside success from spending the last 12 years at Entrepreneur First helping people build companies. The same themes that I see there are the themes that I see in academia as being the potential, the bottlenecks. And of course there's a little bit of a risk that in all you've got as a hammer, everything looks like a nail. But I think what I would say is the thing I've learned about entrepreneurship and startups is if you're going to just do one thing, probably that thing should be find the most talented people that you can and then remove all the barriers and pursue it from them pursuing their most ambitious idea. That's sort of broadly, if you, obviously there's loads, loads of more nuance to it. And I guess, you and I are pretty aligned mission-wise on that, just find extraordinarily talented people, remove barriers, and encourage them to be the most ambitious version of themselves.

I think if you look at academia, I think the same rule applies. Find extraordinary talented people, remove the barriers and encourage them to be the most ambitious version of themselves. So then the question is, why doesn't that happen already? And for me, the number one answer in academia, and one of the reasons I'm so excited about ARIA is that the thing that stops people being the most ambitious version of themselves is time and time again I hear if I try and do that, I just won't get funded. And that's because of the way, again, painting, I don't know if it's exactly the same in the US although I do hear enough things from friends in the US that have looked at this problem to think it's broadly the same. If you go walk around the really great research labs and the really great universities in the US and the UK and you find ... You go around and just say, who are the smartest postdocs here?

And then you go write a list of those and go talk to those people and you say, "What are you doing so cool? What's your biggest idea?" And then they tell you and then you say, "Well, are you working on that?" And they're like, "Of course not." And you're like, "Why not?" And they're like, "Well, because they would just never get funded to do that. If I wanted to get funded to that first I need to get N number of publications with Y number of citations. And so I'm doing this thing because that will definitely get me the publication. And then by the time I'm like 45, maybe I'll be able to do something close to what I think I should do."

And I find that really worrying and depressing because if you look at the history of science, that's not actually where the breakthroughs have come from in general. They typically come from people making anomalous, controversial, weird bets relatively early in their careers and going all in. And my worry is the thing I would change is making that easier to fund today. And I think we have got to the point where rightly, again, we can go back to variance dampening, variance amplifying. What our funding system does today is it reduces variance. Effectively, no one has consciously set out to say this, but what it effectively does is said, how do we minimize the risk that we fund something really stupid? How do we minimize the risk that there's a headline in one of the newspapers that we spent a hundred million dollars on something that was never going to work? And that's variance damping.

“If you look at the history of science, the breakthroughs have typically come from people making anomalous, controversial, weird bets relatively early in their careers and going all in.”

And in some ways that's a good thing. Accountability does tend to be variance damping, as I said before, it's neutral whether this is a good thing or not. Equally, if you think about the real breakthroughs, the things that have moved civilization on from which we get all the things that we care about, a lot of them looked pretty stupid at the start. A lot of them carried a high risk of a bad headline at best and other risks. And actually, I think what I would do is I would at least create pockets like ARIA that are variance amplifying where you say, "Go all in on your most ambitious idea. We've got your back. If it turns out to be the wrong idea, you're not going to be impoverished. It doesn't end your career. And crucially, we're going to fund many such things such that the thing that does work pays in inverted commas for all the rest."

And so, I totally understand why we probably shouldn't take all global science funding and put it through a variance-amplifying machine. There's a lot of stuff that just has to get done where actually you do want incremental progress. But I think taking a portion of that and saying, "Let's throw it through a variance-amplifying machine," is super valuable in terms of human progress.

MM: It's creating an environment for outliers or something before it ...

MC: Absolutely.

MM: Yeah.

MC: Absolutely. And there are very few, again, going back to the theme you started with, if you think about where outliers really welcome in society there's not that many places. Companies are very dampening machines. Yes, they want big ideas, but they sort of mainly want to deliver predictable earnings per share growth quarter after quarter. And you mainly do that by making incremental improvements. And so, corporations select for competence and skill, but they don't select for variance. They select against variance.

Startups, at least in the first few years, the opposite. And that's why probably you and I find them so exciting is that you're selecting for variance, but it's a dangerous thing to do. That's why so many startups, it's not why so many startups fail, but it's an artifact of the same fundamental uncertainty. And so, again, I just think you are exactly right, just as startups have become, certainly in the US I think increasingly in the UK, the obvious center of gravity for people who consider themselves outliers, it would be great if science felt a bit more like that to more people.

MM: Absolutely. Yeah. It's spreading the extremely ambitious, huge jump changes culture of technology into other areas. Shifting more to speak about your work with EF and entrepreneurship more broadly, what do you think are the highest leverage ways to increase entrepreneurship? And potentially, it sounds like there are a lot of parallels here.

MC: Yeah. Well I think there's a few things. I mean, I think obviously, given what I do and what you do, we're probably somewhat sympathetic to the idea that it is broadly going to be about talent. And I really do believe that. So I think specifically, if you buy what I just said that most mainstream institutions are hostile territory for outlier individuals, then that probably suggests that there are a lot of people who are in those institutions who are uncomfortable and feel dissatisfied and disillusioned and constrained and shackled, all these things who actually would be great founders.

And I think one of my slightly more controversial theses about what Silicon Valley gets wrong is that Silicon Valley is that one place in the world where nearly everyone that you meet has already realized what I just said and already brought out, right? And so, there's a huge selection effect in who Silicon Valley people talk to. And so, I think there's this myth that not everyone but many people in Silicon Valley have, which is that anyone who should be doing this has already figured it out. And the problem with that belief doesn't actually affect, I think, very much Silicon Valley because there is a critical mass of people that have figured it out.

But the problem with that belief is that it basically, and it is the opposite of Silicon Valley nearly every other respect, it basically imposes a scarcity narrative over entrepreneurship rather than abundance narrative. Because it basically says, the supply of great founders is more or less fixed. And we know this because anyone who's not doing it already is not suited to do it. Whereas my mentality is the opposite, I would take an abundance mentality. I would say there are many people who have these successful careers who today probably look very entrepreneurial because they figured out the game and they figured out how to get the promotion and the promotion and the promotion until they're very successful that had you place that same talent, that same ambition in an entrepreneurial environment.

They'd have figured out a different utility function and could have been wild as successful entrepreneurs. And so, one of my beliefs is that, as I said, the supply is not fixed and the number one thing we can do is try and increase the supply. And the number one way we can do that is by effectively providing environments that make it more legible, more acceptable, more celebrated to be a founder. And the thing, again, sorry a long answer, but I've believed this for a long time, that's why I created EF with Alice a long time ago now.

“One of my beliefs is that the supply [of founders] is not fixed and the number one thing we can do is try and increase it by effectively providing environments that make it more legible, more acceptable, and more celebrated to be a founder.”

But it's been pretty cool over the last few years to see some academic evidence for this. So, there's a pretty cool paper that came out couple years ago that I wrote about at the time, which basically looks at what happens in years when banks hire fewer people. And when I say banks, this is a UK context, it's talking about the banks that are the sort of employer of choice for a lot of the most talented people, whether or not they ever thought they wanted to be bankers.

So in the UK, the financial services industry is this massive talent suction machine. And so, what it looks at is when banks just reduce their hiring, what happens? Do more people become founders? And the paper basically has two conclusions. One that I think is really intuitive and one that is not intuitive. The intuitive one is when banks have to hire fewer talent and ambitious people, more people become founders. And those founders are more successful on average than people who became entrepreneurs by choice in the period.

In other words, the exact opposite of what we'd expect if you believe that everyone who is going to figure it out has figured it out already. And I think the reason, I think, that's true is that in reality, we are so constrained and shaped by culture, by the culture we're embedded in and the sort of water we're swimming in that it's hard for us to imagine that because we think of an Elon Musk and we're like, "How could Elon ever ended up being a, I don't know, partner at McKinsey or a managing director at Goldman Sachs?" And I buy it, he specifically probably wouldn't.

But I don't think it's crazy to think that there are lots of people who actually just got so absorbed in the game that they found themselves in that it actually wasn't obvious to them. And so, I believe if we can get a lot more of these lost founders who end up in the wrong system, winning the wrong game, as we often say at EF, then we can increase the supply of really great founders. And that's what we do at EF. We want to be the natural home of people who are like, "Wait a minute, the game I'm playing is not the game I want to win."

MM: I really love that. What strikes me about your approach is it's raising the baseline from bringing more people in who wouldn't otherwise be thinking that way. And then also, encouraging and creating the optimal environments for the Elon Musks and the people who will be outliers. And that seems like a really, really poignant strategy. Instead of focusing on the middle and being like, "Let's just make it incrementally better in small ways," when those people would probably be filtering that way anyways, like you said to Silicon Valley.

MC: Yeah. I think that's right. What I'm absolutely not saying is we should just be cheerleaders for entrepreneurship. Everyone should be an entrepreneur. You're in a bank, you should be an entrepreneur. I'm not saying that at all. Actually, I think, in general, advising people to be founders is terrible. You shouldn't do that. However, at the very upper end of the ambition and talent distribution, there are people who would be great founders. And a lot of the skill we think in what we do at EF is trying to tell the difference between the very smart, the average banker in the UK is very smart. It's a very selected full profession.

It doesn't mean they should be founders. We're trying to find those outliers to use the word you introduced earlier. And our view is that entrepreneurship is a high skill profession. It's for only really exceptional people thrive in as founders. And so, it is really about saying, if you live in a society and a culture that every time you do something well and you excel, it nudges you further towards taking a particular career path. That career path is going to be, I'm not just talking about banks by the way, it's true of all anything that attracts talent. You're going to find these tracked careers are full of people who were actually brilliant but sort of just didn't know that this was an option.

“Tracked careers that attract talent are full of people who are actually brilliant but just didn't know that this was an option.”

And when I look at the very best founders that we've worked with and you're like, "Why didn't you do this sooner?" Very often it's just that, "I didn't know it was an option."

MM: Yeah, 100%. What do you think once they realize it's an option, what are the most common bottlenecks that appear after that they have to overcome to become a great founder?

MC: Yeah. This is not designed to be a pop, but Alice, my co-founder and I wrote a book more or less exactly about this question, which came out last year. It's called How to Be a Founder. And the premise of the book is there's tons of books about startups out there, but they all sort of start from the perspective that you start the company and you want to make it better. Whereas our book starts from the premise of maybe you're not even sure you should make the leap into it. And the reason I bring it up is that whenever I get reader feedback and Alice gets reader feedback on it, it's almost always the bit that people pick out is the bit at the start where we're like, here are five myths that hold people back once it's on their radar.

And I won't go into them all, but I would say in general, a lot of the way that entrepreneurship is depicted in popular culture, in my view, is deeply unhelpful for helping people decide whether this is something they should try. So just to use one example, well, I'll use two because I think they're both very dominant in what we hear. One is this idea of readiness. Like, oh, I'm not ready to be a founder. I now understand I can do it and I think I probably will do it one day, but I'm not ready. Now of course, in the limit that's probably true, right? There's a point at which you shouldn't be.

And experience helps and experience always helps. But this is the problem is that I think in cultures where entrepreneurship is not normal, people get very quickly into this idea that there's like, if only I knew X or if only I had experience doing Y, then I would feel ready and then I would start. And of course, the problem is once you've got X and Y, you discover A and B and there's always something that, yeah, if you had more experience you'd be ready.

And the big thing that we argue at EF in our jobs and in the book is that you shouldn't think of your ability as a founder as some sort of analytical fact about yourself. Something that can be ascertained if you do right, ask the right questions and fill out the right survey. It's nothing like that. Your skill as a founder is developed by the act of getting started. In video game language, it's procedurally generated by the work that you do. And so you're never going to feel ready. If the bar you hold is like, oh, I don't know enough about X. No. Guess what? You and you never will.

In fact, the whole point of startups, the whole reason for startups have an opportunity to exist is because they're dealing in the unknown. If they're dealing in the fully known, a big company would be doing it already. I think this idea of readiness is, I think, is a very corrosive myth for people that is now on their radar. The second one, and I will stop after this when I went to all five, is about just feeling that you need to have the perfect idea. And I think the number of people that would rather weekend after weekend polish a Google doc with a beautiful business plan and idea, rather than just get out there and talk to customers is extraordinary.

And I think there is this, if you look at films and books and TV show sort of depictions of entrepreneurship, there is this idea of the light bulb moment, the fantastic idea that it hits you and then what you want to do. In my experience, approximately zero companies, especially the great ones come from that. They usually start from, you either observe a problem or you build a thing and there's some organic pull on it and the organic pull pulls you into a set of conversations and brings you a set of resources that allows you to imagine the next phase, which in turn gives you a set of conversations and resources which allows you to imagine the next phase.

And it's much more the ambition and vision is a product of getting started rather than what gets you started.

MM: I love that. Are there any stories in particular that you think do a good job of depicting entrepreneurship in an accurate way?

MC: Well, I think one of the reasons, I mean I think there's lots of problems with it, but I think one of the reasons that the film The Social Network had such a big impact is that it does sort of push on two things that are really important and potentially seem contradictory if you've not thought hard about them. One is that Zack is clearly an accidental entrepreneur. He builds something and there is that pull and it brings, again, as I just said, a set of resources that allows him to take to the next level. And he's clearly exceptional. He's clearly an exceptional person.

And I think however many years on it's clear, well 20 years on that, he's clearly exceptional. I mean he's been able to ride that journey. And I think often people think of those two conclusions as opposite. Well, if you're exceptional then you must have got it all figured out on day one. And clearly actually what The Social Network shows us is he wasn't lucky. There's lots of people that could have had the pull and not been equal to the challenge. Equally, he wasn't fully intentional.

I think often when we meet people who are like, I think, I have this feeling that this is what I have to do, I should be a founder. I just don't want to be playing this game of climbing the corporate ladder. They're like, but what I need to do is really either think harder about an idea or I need to go and work in place X in order to learn about what thing Y that I want to work on. It's like, yeah, maybe. But I think, again, we're so influenced by other water we're swimming in.

“We meet people who say: ‘What I need to do is really either think harder about an idea or I need to go and work in place X in order to learn about what thing Y that I want to work on.’ It's like, yeah, maybe, but we're so influenced by other water we're swimming in.”

One of the things I'm proudest of EF is that it creates an environment in which people can just explore. And obviously, a lot of the time when they explore, they don't find anything. And that's obvious natural. Startups are weird and find something that's actually worth spending 10 years of your life on is weird. But if you are still in your job, how on earth are you going to find out whether or not you have the perfect idea? You just can't do it. You almost have to make the choice first that you're going to start exploring and start pulling on threads that interest you in order to be in the water that allows you to make that decision.

MM: It's really well played. It reminds me too, I think that a lot of times when people make excuses about not being ready or needing more experience before they're ready to make the leap, it's really because they're just afraid of failure or getting rejected or messing up. And so anything that you can do to make environments where actually taking shots on goal is more celebrated than just staying stagnant. And it's totally fine to fail as long as you keep trying or make a calculated decision and really learn things from that. But it's hard to do.

And so I’m curious, how do you endeavor to create that culture? Is it just having critical mass of a certain mentality and really building it from the get-go or how have you approached it?

MC: So I think certainly, I think critical mass is a huge, huge benefit. You're absolutely right that people are afraid of failure. And when you really push people on it, it's almost never commercial failure. Maybe 10, 20 years ago people worried about, oh, what if I go bankrupt? I think I literally never hear anyone say that today. What they really mean is social failure. What they really mean is, I'm going to quit this job that I competed for really hard, that impressed my parents and my peers when I got it. And I'm going to go and instead of doing this thing, which even though I hate it, it creates legible achievement points for my immediate circle.

I'm going to do this thing that has no legible achievement points where there is no bath, there's no pray, there's no mark scheme, all these things. And so, I suppose what we have always felt was if you could change the peer group, that would be a massive win. If the people around you are suddenly actually if the social currency rather of the people around you is how ambitious are your attempts rather than did you get the badge? That's a big win.

“The social currency of the people around you is how ambitious are your attempts rather than did you get the badge.”

But also, I think, there was something really special that happens when everyone in the room knows that everyone else in the room gave up something really valuable to be there. And I think what it does is it means that you've already done the hard bit. You've already got the kudos of being the ones that tried. Now I don't think you should valorize trying too much. I think you still got to valorize succeeding. That's important.

But I think there is a thing where you're like, how do you create, it's really short, I think we give people about 12 weeks to decide whether they've got something and for us to make that decision too. How do you maximize the benefit of that 12 weeks? Partly by finding ways to forge bonds really, really quickly. And I think the sense that everyone in that room could be making more money, getting more badges, impressing their parents more, doing something else. It's this shared identity on day one that I think is really, really powerful.

MM: Yeah. Reminds me a lot of small group theory too, filtering for people that have some common thread between them all that ties them together. And there's like some shared values as well.

MC: Yeah. And I think one of the hardest things that we do at EF is help people form co-founding teams from scratch. So start companies with strangers effectively or very nearly strangers. And you, again, talking about conventional wisdom, this was probably, and maybe still is, the bit that experienced people from startups when we got started were like, that's the bit that's never going to work, so you should just drop that bit right now. Yeah, and I totally get why, again, I think there's a lot of selection bias like, of course, if there's never been a systematic attempt to help people start companies with strangers, then if you select on who are the people that I see successfully starting companies, it's going to be people starting companies with people they know. I mean that's just like a very obvious statistical artifact.

But that said, I do think it's true that there is a really hard problem to solve if you are starting a company with a stranger, which is have you any idea whether there's a compatibility there? The controversial bit I believe is that the same question actually applies to start a company with anyone. When someone's like, "Oh, I'm going to start this thing with my best friend from work." I'm like, "Cool, have you ever started a company together before? Because if you haven't, I kind of don't care about any previous experience you have social or work."

Because starting a company is really different from anything else and it's going to put pressures on your relationship and on your ways of working and the demands on you that are totally different. And so, what we realized at EF was the stupidest thing we could do, which is what we did for two years because we largely started doing stupid things, is to try and think of this as an analytical problem where you make people take quizzes or let people sort of spend loads of time getting to know each other and go for drinks together and figure out who they're friends with.

And they'll pick the people that are the closest proxies for the people they would've picked had they been to school or work with these people before. That was turned out to be totally wrong. The thing that turned out to work was to abandon any pretense that this is an analytical exercise, instead just really lower the social friction to just getting started, but also really lower the social friction to just stop it. So, a failed team at EF might last 48 hours in the sense that you're literally like this is a poor people who've all given up something valuable to be here. They've all come to join this community because they're very ambitious and very talented and they want to start companies.

“The thing that turned out to work was to abandon any pretense that this is an analytical exercise and instead just lower the social friction to getting started and stop — a failed team at EF might last 48 hours.”

The opportunity cost for being in a bad team is really, really high. You've only got 12 weeks. And so, all we do now is we say, "Get in your first team in the first few days and start working." And really the only way you should evaluate whether or not this is a good team is are you productive? Are you getting more done than you would expect given what you know about yourself? If you are, keep staying in the team until that's not true. If you're not, break it up, get out, try someone else.

And actually, what we find is that when you lower that friction to getting out of the teams where it's like just norm, everyone knows it's fine if you broke up, everything gets really easy for getting into teams. And so people actually try a lot of things. And so, the one thing that everyone thought, including ours I have to say, will break EF. The idea that the teams will just be really non-resilient after they graduated from us has turned out not to be true. At least, the data I have suggests that EF teams that raise a seed round are less likely to lose a co-founder before series A than at least London based teams that form organically in the wild as it were.

MM: That's amazing. It reminds me of a micro version of the stats on entrepreneurship being mainly just about how many shots on goal you had. It's the same with trying a bunch of different formations of team. Because people, yeah, you don't really know actually how the combination will work and how symbiotic it'll be. And then, at a larger scale when they're actual companies, whether there's a real market in demand there.

MC: Totally. Totally. So much learning by doing, right?

MM: 100%, yeah.

MC: Anyone who tells you otherwise say, "I don't get it." The whole point of working in the realm of deep radical uncertainty is you usually just have to try stuff to learn anything.

MM: And it takes a lot of courage to have that resiliency. Yeah.

MC: Yeah.

MM: At a higher level, I'm curious, if you could change anything about how the government operates or institute any policies that would help encourage entrepreneurship, what would you change? Or what would the policies be?

MC: Yeah, I mean, again, a risk of just having a single theme. I think the single biggest thing that let's take a UK or a US government could do, because they're the places I know the best, is just make it really, really easy for the world's best talent that want to come to those countries, to build companies, to do so. I mean, the US in particular having Silicon Valley is the world's great asset of having, sorry, ecosystem asset, right? I mean, it's just extraordinary.

So if there are tens of thousands, even hundreds of thousands of people who are incredibly talented, adding to that ecosystem will increase the value of the ecosystem. It's the world's best free launch to let them come and do it. And I have to say one thing that has been pretty good in the UK over the last decade is making it easier and easier for entrepreneurs from outside the UK to get visas to come here.

We fed into that a little bit at EF and I think the exceptional talent visa in the UK, I believe is the best visa in the world for founders right now. And it's really good. But I think any government that is serious about entrepreneurship basically just has to have an open door policy when it comes to extreme talent, particularly extreme technical talent and founder talent. But that's sort of harder to define. So that's one. I think, in general, the other things are things about make it really easy to invest in startups, certainly not tax punitive to do so. Make it really easy to be an employee in a startup, particularly when it comes to options.

Basically just make sure the incentives are really, really well aligned for talented and ambitious people to make their bets in this sector versus something else. But ultimately I see these things as talent challenges. Again, hammer, nail, et cetera. But it's striking to me when I look outside the UK, how many countries make it really hard for great people to either move there or stay there. I mean, the craziest ones are where a country will take grad students in technical subjects, give them degrees and then be like, "You can't stay." These are the people that are going to build the things.

To me, that is such low-hanging fruit that almost everything else feels like an afterthought. But I guess if I had to point to other things, and again, bias because it's partly what I do. But I do think investing in fundamental R&D, everything we know about the economics of innovation is that investing in fundamental R&D is really, really good for long-run innovation. And so making sure that you have a really great academic sector, particularly in science and technology, is really worthwhile. Creating the incentives that make it really easy to spin breakthroughs out of universities into companies that don't mean that the founders on day one already own less than half the company and all this stuff. The somewhat low-hanging fruit there as well.

“Investing in fundamental R&D is really, really good for long-run innovation. And so making sure that you have a really great academic sector, particularly in science and technology, is very worthwhile. Creating the incentives that make it easy to spin breakthroughs out of universities into companies.”

But in general, I would say, if you've nailed basic talent access and basic capital incentives, you've probably done 90% of the work.

MM: Yeah. Do you think that there's any areas of improvement in terms of the venture model? Because venture very much is incentivizing the 10X outcomes, these huge innovation outlier outcomes, and that's wonderful. But I think that there are a lot of things that don't fit into that model that I think venture is becoming more self-aware that perhaps they're missing things because of that. But I'm curious to hear your thoughts on that.

MC: Yeah, no, I mean it's a great question. I think it's one of those things where there's a joke about hedge funds that hedge funds aren't really an asset class. They're just a compensation scheme that's been generalized. And there's an element of truth in that. But the serious insight behind that joke is that it is an incredibly valuable thing for an asset class to be legible to capital allocates. So the really great thing about structuring yourself a venture fund, if you want to fund innovation of any kind, is that LPs understand it. And I don't mean that at the level of, oh, do they intellectually get it? I mean, LPs are smart people.

I mean, does it fit into a sell in their grid when it comes to asset allocation? And for large pools of capital, of course they have to view the world somewhat like that grid. They generally are not going to do things that they can't cover systematically. And so, one of the reasons that venture ends up taking on a lot of things that don't really fit very well with venture is because venture's super legible to LPs. And so you can raise money to do it.

“One of the reasons that venture ends up taking on a lot of things that don't fit very well is because venture's super legible to LPs. And so you can raise money to do it.”

I mean, I have learned that both the hard and the, I don't want to say easy way, but in both positive and negative sense that EF is not a very natural fit for a traditional fund structure because so much of what we do to earn the equity we get is not the cash we invest but the work we do. And we spend 10 years trying to retrofit that into a fund structure. And it sort of worked. And we've been lucky to have great LPs and also deliver really great returns to those LPs.

But last year we were able to restructure as a permanent capital vehicle where all the capital we raise from investors now going forward comes into the company. And that allows us to be much more flexible in how we think about our operations as a source of value. It's very hard for a fund to think of operations as a source of value unless the assets under management is so huge that the management fee is a corporate-sized revenue stream. But EF isn't that scale. Very few funds are.

And so, we found that we were very lucky to find investors that resonated with who were at least many of the investors in the funding round that made that possible were not traditional LPs. Some were as well very forward-thinking ones that were very lucky to have. But finding first principles, thesis-driven, pools of capital that are willing to try new structures is hard because, in general, you don't want something to fail because of the structure. Because in the same way that no one got fired for buying IBM, no one actually got fired for buying 2 and 20 with a 10-year closed-ended fund cycle like that. That's right. That's the normal thing.

Sorry, I've sort of slightly got away from where you started, but my broad point would be, in general, if capital is the bottleneck, the hard thing is finding initial investors that can help you validate structures that are not the classic 2 and 20 10-year closed ended fund.

And so I think it's great to see that there's a lot of people that made a lot of money in tech in the last 10, 15 years who are actually really key to do first principles thinking about the right structures for these things. And that's why if you read the list of people that kind of backed EF's series C last year, that allowed us to do this transition to this permanent capital model, it's largely a list of entrepreneurs. It's people like John and Patrick Carlson, Reid Hoffman, Matt Mullenweg, et cetera, et cetera, they're not constrained in the same way that an institutional LP would be. And so I think that's really great.

I would love our billionaires to do more non-traditional structure in the way that they invest because it's what eventually pulls the rest of the capital allocation world towards things that today look quite niche.

MM: It's all about the incentives you design for yourself. It is interesting too because I feel like venture, in general, it's just like a funding model, but then you can do what you will with it, but you do create incentives by the capital you take from and the expectations you set more than anything else.

MC: Yeah. And it will be interesting whether things change a bit. As VC goes through this huge transition of getting used to a non-zero interest rate world because part of the problem has been frankly that it's been too easy to make money in VC. And I mean that in a literal sense, as in people thought they were making money that they were not making. And therefore, things like funding hardware, funding deep tech, funding anything that's going to take a long time, became very, very hard because it felt like the opportunity cost was free money investing in SaaS. It turns out that money was not free.

So you can tell a negative story that maybe things will get worse because there's going to be a general sort of cyclical outflow of capital from VC. But you can tell a story that it will get better or it will get better for stuff that is not mainstream today in that the opportunity, the perceived opportunity, cost of funding weird stuff has actually reduced.

MM: That's a great answer. How do you see the next 10 years of EF playing out and how does it fit in?

MC: Yeah. So we sort of feel like EF is just embarking on the start of its second chapter right now. And it really was that flip to a different structure that enabled it in the ... I think where we've got to is we really believe that the category that we've created is going to be extremely valuable. And the next 10 years are really figuring out what is the scalable model for ensuring that we capture the full benefit of that. And I think what we've come to the conclusion of is that we probably thought about it too much in a top-down way before.

We created this product. By which I mean the system of EF. And then we expanded to other countries by hiring great operators in those countries, giving them the product saying go to the races. And actually, I think, we've just made a big switch in that we now would say the really scarce resources are the people that can build the bottom-up relationships with great talent really early in their career.

It's not a plug-and-play machine. It's not a machine where you crank the handle and kind of good people in, good companies out. If you really want to build needle-moving companies that start by forging incredible relationships very early in people's careers and being genuine career coaches for people as they decide even whether they should be founders, never mind how to be a founder, and then taking them on that journey.

And so, we've done a big restructure at EF over the last year where we've moved away from this top-down model and really gone all in on this idea that we want to create a new career path for people that we will call talent investors. And it's sort of unlike, I think, it's a little bit like being a VC, it's a little bit like being a talent agent. So a little bit like being an operator, but it's really none of these things. It's a new thing, which is finding people that will be the thought partners, counselors, and coaches to the next generation of Patrick Collisons’ and Elon Musks’ and Matt Mullens’ and all these people.

And I think a book I would really recommend to all your listeners is this book that came out, I think, last year called The Power Law by Sebastian Mallaby, which is a history of venture capital. And it's great. There are loads of great things about the book. But the thing I loved about the book is you realize for the first 20 years of what we now call VC, everyone was sort of feeling around in the dark. All the things that are now, like completely rigid structures of VC were off for grabs, and people were feeling around it.

And one thing I often say to people who apply to work at EF as talent investors is we've been doing this for 10 years, but if you look at the history of venture capital 10 years in, no one figured anything out. That's where we are right now. We've done enough to earn the right to be here. But in terms of where we'll be when someone writes the book about talent investing, we're basically equivalent to day one for the first 10 years of the rounding era. And the exciting thing for me is you read that book and you read about the impact that people like Mike Moritz have had on that whole asset class.

And you say, "Who's the Mike Moritz of talent investing?" Well, it's not me. I mean, I hope that my investments today turn out to be great. But my guess is that Mike Morris of talent investing hasn't yet applied to work, but they will. And I think they'll have a comparable impact on talent investing that Mike had on venture capital and that's what I'm excited about the next 10 years, is actually finding the next generation of people that make my track record, which I have to say is actually pretty good, but just by out of water. And that's what I'm really excited about right now.

MM: What a wonderful answer. Well, thank you so much for coming on the podcast, Matt, it was a pleasure to have you.

MC: Molly, thanks so much for having me. I really enjoyed it.

Subscribe for more episodes to come: Spotify, Apple, Google, Amazon, and Overcast.

Highlights:

• In order to increase entrepreneurship, it’s easiest to expand a person’s ambition at the start of their career. This could take the form of giving small sums of money and/or creating more tracked paths that make entrepreneurship (not necessarily at a venture scale!) legible as an option to those that might not be exposed to it.

• At the start of your career, focusing on building a real business that makes money can give you the financial freedom and confidence to take bigger, more ambitious swings in the future (both the Collisons and Zuckerberg did this).

• The biggest problem the US is facing health-wise is that the market isn’t flowing freely. In contrast to Silicon Valley where software gives us permissionless innovation with huge outcomes, the health sector is not designed to financially reward those that solve the sector’s most pressing problems adequately to their impact. Ceasing to give crop subsidies would be a good first step in allowing the market to self-correct.

MM: Hi everybody. Today I’m joined by Justin Mares, a serial entrepreneur and investor who founded startups like TrueMed and health brands like Kettle & Fire, Surely, and Perfect Keto.

Our conversation covered strategies to increase entrepreneurship, the ingredients and misconceptions around success as a founder, and the US health crisis. I hope you enjoy.

MM: Hey Justin, and welcome to the podcast.

JM: Thanks for having me. Excited to be here.

MM: Amazing. For my first question: what would you say is the moonshot of your career?

JM: Well, I hope that the moonshot of my career hasn't yet been taken on.

MM: Hasn't been shot yet.

JM: Yeah, exactly, exactly. I always think that when I started my first company, my moonshot was a personal financial goal and then as I've achieved certain things or the companies have grown and my career has gone on, I think that I've increased the scope of my ambitions and so I just hope that that continues to happen to be totally honest.

MM: Yeah, that's a great answer. Expanding the altitude and the magnitude as well.

JM: Yeah, exactly.

MM: What do you think are the threads you've kept pulling throughout your entire career?

JM: I think one of the threads that I maybe unintentionally stumbled on or got into was just what I think is one of the craziest things in the US, which I end up talking a lot about, but I think the just core thing is if you roll the clock back 50 years, our parents and grandparents would basically, chronic disease was basically a sixth of what it is right now. Obesity, overweight was closer to an eighth of what it is right now. Spending on healthcare as a percentage of GDP was 15% of what it's today.

And all of this during a time when people were working out less, and smoking more, you would ask your grandparents or parents, "How do you think about health and wellness and diet and all these sorts of things?" And they'd mostly just be like, "I don't know, I just buy shit at the grocery store that I think tastes good."

And so just in my opinion, I think it is so wild that we have accepted somewhat implicitly that we have a food system and a food environment that makes almost everyone sick, unhappy, unhealthy, all these things. And I think that very, very few people are interested or trying to fix what, in my mind, is this core obvious massive, screaming problem that is almost everyone that is suffering from some sort of metabolic disease, any number of these things.

And so that is the common thread that I feel is the through line through a lot of what I've done is just what are the root causes that are leading to all of this, all of these health and other issues and what are the companies or other solutions that I can try and start to get involved in that hopefully solve some aspect of that problem.

MM: Do you have any sense of what part of your personality is the right fit for this problem? It seems like so many people are passing it on. What about you makes you uniquely suited to try to help solve it?

JM: It's a good question. I don't know. In some ways, I don't know that I am uniquely suited to it. It just sort of is a thing that I feel compelled by and others don't. And so in some ways that's its own thing. But I think that I do have maybe somewhat of an optimizer personality type. And so when I first came across this idea or that what you put in your body actually drives certain health outcomes... It may sound silly, but when I was in college I didn't have the mental model of food and things that you put in your body determine how you feel, how you act, how you look, all these sorts of things, which is like food is I'm hungry and it's fuel.

And I backed the Soylent Kickstarter campaign. I didn't think of it any more than that. And I think that as I understood more deeply the relationship between what you're putting in your body and your physical health, your mental health, your happiness, performance, all these sorts of things, longevity, everything. I just wanted to optimize this thing more and more and more. And as I got more into that, I just kind of realized that there are, in my opinion, shockingly few people that care about this stuff or is interested in this stuff as I am. And I don't really know why that is, honestly. It just seems to be the case.

MM: I like that. Who most inspired you growing up?

JM: It's a good question. I think that there are different people that inspired me in different ways. So my grandfather is probably one of the most inspiring people that I've met from a super high-integrity gentleman, amazing father, amazing parent, amazing husband, just like 10 across the board. When people would talk about gentlemen, my grandfather is like that guy actually and just such a morally good person and I respect the hell out of him for that.

And so he was a real role model in that way. He and my grandma went to prom together, and are happily married 60 years later now. That was a role model in that sense. And then locally, I feel like for whatever reason, I feel like my ambition didn't get triggered for quite a while until I was in college. And so I had some people that were role models. My then girlfriend's dad was the first entrepreneur I ever met and he had total time freedom, which I thought was awesome. And so he was definitely a role model in that sense too.

MM: Cool. That's neat. Was there anyone that bet on you early that elevated your ambition?

JM: Yeah, I mean, certainly. One of the kindest things that someone did for me and why I started this program, which you and I have chatted about called Inflection Grants, is when I was in college I had this opportunity basically, or this sort of crossroads where I was starting a company, it wasn't working and I had very little runway left. I was paying myself $1,000 a month and I had three months of runway with that.

And so, one of my mentors and one of the guys that I got to know when I was in college, I was kind of telling him this and I was just saying, "I don't know if I should just jump ship and not do the startup, go get a job somewhere normal," normal kid graduating college in Pittsburgh meant PNC Bank or Dick's Sporting Goods, not like a cool San Francisco tech startup. A very, very normal corporate thing.

And I was just kind of walking him through, "I don't think this is working. I maybe should just go get a job. Maybe this is not a thing that I'm cut out for." And he made an incredibly kind offer and was like, "You should keep doing the startup thing. You should try and stay in startups and if it doesn't work, I will basically cover six months of your burn or just hire you if what I'm telling you to do doesn't work." And that would've cost him, it was not a crazy amount to him. It was probably like 25 grand given my spending at that time or something like that, maybe less. But for me, that offer, which I never took him up on just was enough where I was like, I can keep going down this weird nebulous, very illegible path and know that I had some sort of security if I really needed to call him up and take him up on that offer. It was wild what that did for my ambition and sort of made me feel okay really going forward from a career standpoint at that point.

“That offer was enough to make me feel like I could keep going down this weird, nebulous, and very illegible path and know that I had some sort of security if I really needed to take him up on it. It was wild what that did for my ambition.”

MM: That's amazing. It's such a psychological trip to create a new baseline.

JM: Totally.

MM: It's almost like baking in what's already baked into a job package too.

JM: Completely, or having great parents or something like that.

MM: Yeah, exactly.

JM: Which I didn't have, but in a way I think that that offer is such a high-leverage thing. It literally cost him $0 and it did unbelievable things for me, which is just so cool.

MM: It's amazing. To that point, I'm curious, what high-leverage initiatives do you want to see happen to empower, especially early career entrepreneurs?

JM: Good question. I think that something like that, the offer that I got is actually pretty compelling. Maybe that should exist maybe in a more informal way or more formal way. I don't know. One of the things that I want to see exist, which I'm sort of working on the side, we're both doing somewhat similar things, although you much more intensely and thoughtfully than I am is started this Inflection Grants program, which is a pretty similar idea of for people who are very earlier in their career, I think that small amounts of money can make a huge difference in unlocking someone's potential.

I often think that if you want to take a 35-year-old with three kids who maybe would be an incredible entrepreneur or should be in Silicon Valley or in some tech hub, it's so expensive to take that person out of the middle of Pennsylvania and bring them to San Francisco, Silicon Valley, transition them into working at Stripe or whatever it is. With an 18-year-old or 16 to 20-year-old, that is so not true. $2,000 can literally change the course of someone's life.

“If you want to take a 35-year-old with three kids who maybe would be an incredible entrepreneur, it's so expensive to take that person out of the middle of Pennsylvania and bring them to San Francisco. With an 18-year-old or 16 to 20-year-old, that is so not true. $2,000 can literally change the course of someone's life.”

And so the leverage you get there I just think is so incredible. I've seen it in my own life. The program that I started called Inflection Grants, we've given almost 40 grants to kids. I don't know if... kids too low, early 22 people, I don't know what you want to call them.

MM: They’re still kids.

JM: But yeah, we've given all those grants and I think that that is a really interesting leverage point. The other thing I would say is in terms of early career entrepreneurs, I think that I've seen a fair number of people, I was probably one of these people myself who knew that I wanted to be an entrepreneur but didn't necessarily have a good idea, network, career experience, anything like that. And "the path to starting something" is so illegible that I think as an ecosystem adding legibility to that or even a more formalized... I don't know if it's a, "Hey, I'm an entrepreneur, come work with me as chief of staff, and then go start your own thing in two years."

I don't know if it's formal incubation programs where you have successful founders that partner with early career entrepreneurs and say, "I'm going to put in my time and own part of this company. You're the guy or girl running it, but you get all this mentorship and advice and deep insight into a market." I don't know if it's something like that. It does feel like there are so many people that want to start things and so many people that take the leap starting something dumb and it feels like there are probably way better pathways towards building things that then exist today.

MM: It feels just not well organized. It just seems like the supply and demand, but it's all over the place. And then there are more credentialed paths like YC that kind of give you some of that curriculum and network and those effects, but the more credentialed they become, the more they attract perhaps a lesser quality of the entrepreneur. Just like there are tradeoffs to everything.

JM: Totally.

MM: I think that there is definitely just a coordination problem in matching these people.

JM: What would you do?

MM: That's a good question. I think some paths should become more legible. The one of chief of staff to founding something, that seems like it would be highly attractive to a lot of people if more people knew about it. That's something that I didn't realize was a pretty common path until I just saw people doing it. And I think that story should be told and actually shaped into a program or something of the like.

But I do think that it's hard to not start selecting for people that are looking for tracked paths once you start making something legible. And so that's a trade-off that I don't know how to balance except for spitting up a lot of different programs that are new and attract the right people at the start and then destroying them quickly and building a new one. That's my working solution is just a minimum viable engine to attract all the nerds and avoid the sociopaths and the mops.

JM: That's interesting.

MM: The David Chapman reference.

JM: Maybe I'm overestimating this just this is sort of my path, but I do think that even if you have a tracked program that starts attracting credentialed people, for someone like me who didn't come from money knew, no one who was in entrepreneurship, didn't even know Silicon Valley was a thing, just getting in the game opened my eyes to a whole world that I didn't realize existed.

MM: Totally.

JM: And I think that having that as, even if it's a little bit of a tracked thing where you get some funnel of people that are sort of clueless and then can learn, oh, this is a game that I can try and learn, do, self-actualize through, I think is probably still underrated. That's my opinion.

MM: Still very much net good, having more people.

JM: Totally.

MM: These things in general. What do you think, other than the 35-year-old who is kind of stuck in a job and now has a lot of obligations, what do you think are the other bottlenecks to entrepreneurship?

JM: That's a good question. I mean there are certain societal ones probably on the margin more people would start a company if there were healthcare things, or there's some sorts of things where for an individual, the risk trade-off of entrepreneurship doesn't make that much sense. I think that's gotten a lot better though with just how many seed and pre-seed funds exist. I think that you can raise a small amount of money, pay yourself for one to two years and get healthcare as part of that. I don't think it's this crazy barrier as much anymore.

I actually think that one of the things that I'm interested in is I think that right now Silicon Valley has done an amazing job exporting the operating system of a Silicon Valley startup and sort of owning the idea of entrepreneurship equals starting or running a venture-backed company. And I think that there's way more opportunity and there should be way more entrepreneurs outside of Silicon Valley starting companies that are maybe not necessarily going to be the next Stripe, but that create jobs and reflect the desires of their local market and industries much better than some massive national chain or whatever.

So I want to see way more. One of the companies I think is so cool is I want to see more companies like Shopify that enable 20,000, 200,000, two million entrepreneurs that can start something at a local level because they have these amazing set of tools. We have one Shopify, but it's enabled hundreds of thousands to millions of entrepreneurs, and that kind of thing is really cool. And I think that I want to see way more tools like that that just enable long-tail entrepreneurship as opposed to just how we get more Silicon Valley-style outcomes, which I'm very less certain of, honestly.

“We have one Shopify, but it's enabled hundreds of thousands to millions of entrepreneurs, and I think that I want to see way more tools like that that enable long-tail entrepreneurship as opposed to just focusing on how we get more Silicon Valley-style outcomes, which I'm very less certain of.”

MM: Skeptical. It's very oversaturated. It's like building platforms that raise the baseline for entrepreneurship of any type or scale.

JM: Totally. I don't know, I'd actually be curious about your thoughts too, but I don't think that we are oversaturated with entrepreneurs in Silicon Valley, but certainly, I meet people that are way smarter than me in Silicon Valley startup world. And I have met way smarter people running B2B SaaS businesses, running businesses that aren't working, running all sorts of things. And I'm like, yes, there's so much more innovation that could be happening, but also this shit is just really hard and we already have a ton of talent running at different venture-backed startup things and most of these things are not going to work. If we 10X that, do we get 10X better outcome? Do we 10X the number of outcomes? I'm not sure. I don't think so.

MM: I mean, we'll see.

JM: Yeah, totally.

MM: It does seem there's something weird about saying that anything less than a multi-generational business is a failure of interest standards. That seems wrong. I mean, it's not wrong for the business model of venture, but the fact that we're so constrained that we only really have that one for a sector that has entrepreneurship of all different scales. There are a lot of medium-sized software businesses that aren't going to be multi-generational Stripe-like companies.

JM: Totally.

MM: But what do we do with them? How do we fund them in a portfolio for a VC firm? They're going to be deemed as a failure. They're going to be like, "Oh, it's the bottom of the curve. Nothing going on there. It's not going to return our whole fund."

JM: Exactly.

MM: Yeah. It's a shame. Have you looked at SEAL notes (Shared Earnings Agreement)? Those are the ones where they're venture investments if you reach a certain threshold.

JM: Oh, yeah.

MM: Then they're a revenue share if you reach a certain threshold.

JM: Yeah, this is the Calm Capital guys thing, right?

MM: Exactly.

JM: Yeah, exactly.

MM: That seems good. That seems like the incentives are actually correctly aligned.

JM: I totally agree. And Bryce Roberts from Indie VC, he's bringing Indie back, which I think is going to be awesome.

MM: Yeah, exactly. Extremely cool.

JM: So I'm super bullish on that type of model as an investor. I'm very bullish on maybe long tail entrepreneurship is what you could call it. I'm also bullish on Silicon Valley. I just don't know the core assumption for me, which is if we 10X the money and 10X the talent in the Silicon Valley ecosystem, do we get 10X the returns? Or 10 times more Uber open AI, whatever. For some reason, I can't totally place a finger on it. I don't think the answer is yes.

MM: Yeah, that sounds right to me too, without a clear reason why. I'm just curious when you're evaluating the entrepreneurs that I agree are pretty plentiful around here, what do you look for in them? What are the qualities that you think make someone successful and how has your thinking on this also evolved as you've grown up?

JM: That's a good question. I think that a lot of... Let me think about this. I think that one thing that I've started to think a lot about is when I was in my early 20s, I feel like it was much harder to evaluate friends that were also in their early 20s who were starting companies because you don't necessarily know what excellence looks like and you're just, for me, was watching a bunch of my peers take random shots because they thought something was a good idea and it hit or it didn't and there was a massive skew in outcomes.

There were certainly people that were smart and worked hard, but I also had friends that were super smart and worked hard and things didn't necessarily work as well. It feels like a much more random game to bet on young people who are figuring themselves out while also trying to figure out what they're working on at the same time.

I feel like now I'm in a position at 33 where I see a bunch of my friends that are also in their late 20s to early 30s working on starting their next thing. And the friends that I've seen do the best and that I get most excited about and that I'm proud to be involved in their companies as an investor or something like that, are almost entirely the friends that are extremely mission-oriented and mission-driven, where you're just like my friend Dylan from Mind Bloom, he started Mind Bloom, first psychedelic therapy company, in 2018. And you talk to that guy and he has an incredible story. He had mental illness on both sides of his family. Went to Penn on a full scholarship, just a really amazing thing. And personally saw his life transform by using psychedelics in an intentional therapeutic way.

“The friends that I've seen do the best and that I'm proud to be involved in are almost entirely the friends that are extremely mission-oriented and mission-driven.”

And so you talk to him and he's just like, "This is going to be a fun thing for 20 years, I believe in the 20-year vision of what psychedelics can do for people." And I have friends that are like that, that are much more mission-oriented toward solving one problem are the ones that are the most interesting to me. And I would be like, I will back and support the first company if that fails, the second company, you just know that they're going to be operating in the same space trying to solve the same problem for probably the rest of their career.

MM: They get closer every time.

JM: Exactly. The people that feel like they're doing their life's work are absolutely my favorite people.

MM: And they're just inspiring to be around too.

JM: Totally. Yeah, it's way more fun.

MM: It's infectious. It's like, damn, I want to be more like that.

JM: Totally. Exactly.

MM: Yeah, that's cool.

JM: How do you evaluate talent at this stage?

MM: How do I evaluate talent? I think I do a lot of pattern matching from the founders that I've worked with that I know to be exceptional and have seen exceptional excellence in action. And so I look for precursor qualities to that. And what that usually boils down to is just are they obsessed with the thing or do they have the capacity to be obsessed with a thing and demonstrated track record of sticking to something for a long time?

A lot of the people that I evaluate are in their early 20s. So it's really like that is the first fork in the road is like, can they stick to something? Because very few can, yet, and that's fine. But I think I like to keep tracking the people that are still exploring, but they're just not clear bets yet. I just don't have enough signal, I think.

But other than that, I think I really like people that are more T-shaped, so they're generally competent and have some background that lends them to interesting insights. Maybe it's an unconventional multidisciplinary thing, but then they also have a core competency. Maybe it's coding, maybe it's business stuff, maybe it's design, whatever it might be. But they have a real reason to be confident and they attract people.

And I just think that competence is like, it's the core unit of respect, and if you don't have it's going to be hard to lead something, especially getting it off the ground. So I look for that too. It's especially rare in young people. And then I was just like, do I like them? That also seems important, especially when you're stuck with them from an investing standpoint for technically 10 years.

JM: Completely. That's really smart.

MM: Okay, another question. I'm just curious, what advice do you give to young budding entrepreneurs that are just beginning to get their first shots and goals? So these people that perhaps are still exploring the idea maze?

JM: Yeah. I have a lot of thoughts here.

MM: Amazing.

JM: One of the things that I think is very true is what you just said about competence is the core unit of respect and being able to recruit people, being able to self-actualize in the world. I think that Silicon Valley, a lot of the advice that Silicon Valley gives around finding a big market, do something you're passionate about. The missionary stuff that I was just talking about, I basically don't think that should apply to people under the age of 26.

MM: Interesting.

JM: If you're an exception, you'll know. If you're a Zuckerberg or Collison, you'll know. But I think for the vast majority of people, and speaking personally, this was certainly true for me. I knew I wanted to be an entrepreneur and I knew that part of the reason I wanted to be an entrepreneur was just to achieve financial freedom and everything.

Everyone you talk to in Silicon Valley is, "No, you should go after X, Y, Z, big ambitious thing. Trying to make a couple of million dollars and having that in the bank account. Horrible idea. How could you not be so ambitious?" I actually think that for most young people that want to be entrepreneurs by far the better path is just trying to make one to five million dollars and get that in a bank account because doing that is fucking hard.

It's like practicing. It's like you have to level up your competence and you can... One to five million dollars, there's a massive, massive number of businesses that you can start by, participate in, do whatever to try and get that number. And by doing that, you will learn so much because in the game. And where I see a lot of, I think young entrepreneurs burnout or struggle is they sort of just spin their wheels on 30 different ambitious ideas that don't go anywhere and then they end up getting a job somewhere. And I think that that is the failure mode that I see among young, super ambitious, talented, wannabe entrepreneurs way more than young people that they've started a business, it's working and they're like, "Oh, I'm trapped in this business forever." I don't think that's a real thing necessarily. Or you can opt out of it at some point.

MM: Totally. And it seems like if you're aiming for something reasonable-ish like that too, it actually gives you real feedback loops on developing a competency. Are you actually doing the thing? And then once you have that as a baseline of knowing you have that cushion, then you can make bigger swings. But the first one has to actually have a loop.

JM: Totally. And exactly. If you are starting a thing that is so hard, it is so unlikely to work, it is almost impossible to develop self-respect and confidence and the learnings if you're doing a thing that doesn't have any positive feedback loops in it, because it's just so hard.

I know that I would like to continue doing ambitious things in my career. Some of the things, like the thing I'm doing now in my new company, there is zero chance that I could have started running or operating this company when I was 22. It would already be dead. We've been around for a year and it just would've been dead already. And I think that I just haven't heard that many people talk about this idea, which I think is true, which is that it is okay and probably good for young, talented, hungry people to just focus on building a business, making a couple of million dollars and then starting their big ambitious thing. And the Collisons actually did this. They sold a company before Stripe.

“I haven't heard that many people talk about this idea, which is that it is okay and probably good for young, talented, hungry people to focus on building a business, making a couple of million dollars, and then starting their big ambitious thing.”

MM: Yeah, that's one of my favorite fun facts.

JM: Yeah, Zuck sold a company before he started Facebook. They just did this when they were 16 and then started the big thing of 20 or whatever. But I do think that this competence cycle and feedback loop, as you're saying, is so important to kick off.

MM: I really like that answer. That's really good. Does that imply perhaps a don't raise venture for your first thing?

JM: It can. I mean, I don't know that I would be that prescriptive about it. I think that for some people it can, but also for some people, one of the best things about Silicon Valley is that wealthy people will give an incredible amount of money, like amounts that would befuddle my parents to 21-year-olds that have no track record, no anything.

And so I think that that in general is a beautiful thing. I do think though, that if you can raise money, it probably also makes a lot of sense to not buy into your own hype, believe the thing. But if you're raising money and you can maybe hire a really talented executive team around you faster and invest in a coach. There are ways that you can work it. I just think the broad thing is I wish that I was more okay with just wanting to make a couple of million dollars when I was just starting my career and not always feeling bad because I wasn't starting X big thing.

MM: 100%. No, I think it's much more attainable and also it makes it harder for you to bullshit yourself into being like, this is a 10-year project type thing… “I don't know if it's working. I have a grand ambition.” But you don't know if anything's working. You're too young to be making those big, huge swings that you’re basically blind on how to do.

JM: Totally. And I think your point is you just don't have feedback loops in many cases when you're doing a 10-year project, you have no feedback loops that entire time for the way that many of these young people are operating these things.

MM: Completely. What do you think are other feedback loops that you can build in for yourself other than trying to build a business at the start of your career with a more realistic scale?

JM: I actually think that working with people that have built or are building businesses that are doing well, that they have experience. I lived and worked with a guy for basically a year who was 38, sold six businesses, and had just done incredibly well. And watching how he operated versus how I would operate, I was just like, "Man, there's such a gap here. I have to learn, and I can learn so much from this guy." And that was really useful.

“I lived and worked with a guy for basically a year who was 38, sold six businesses, and had done incredibly well. Watching how he operated versus how I operated, I was like, ‘Man, there's such a gap here. I have to learn.“

So having a very tight-knit feedback loop, often this is chief of staff or where something like that can come into play. Other things, like one of the things that I did with one of the first companies I started is I was 25, didn't know the industry that I was moving into and decided very intentionally to give a huge advisory grant basically, to one of my first mentors, advisors in this space.

And in return for that, I had breakfast with this guy every week for a year and a half and had this feedback loop of me, a clueless 25-year-old running this company, but had this 41-year-old. I would just bring a bunch of problems to him every Friday. We would chat through it and then I was making decisions the way a 41-year-old seasoned CEO would just in my 25-year-old best attempt at doing that. So I think advisors can be an incredible feedback loop for a lot of this. Those are at least two that really worked well for me.

MM: How did you approach it? Did you just ask him, "Hey, can you, in exchange for this advisory, meet with me on a weekly basis?"

JM: Yeah, I got introduced to him and we had a couple meetings, coffees. I really liked the way he thought. I thought we had a good relationship. There was good chemistry there. And basically I was like, "Hey, will you be an advisor at the company? Would love to have you." And he said, which is true, "Advisory is never worth it." It's almost always true. It's like a big time commitment for a quarter point in the company or something like that.

And so I was like, "Hey, what if I actually make it worth it for you?" And so I gave him, I think it was like 4% of the company and on investing and all these sorts of things, but that 4% was so worthwhile for me.

MM: That's amazing.

JM: Because I just had this crazy feedback loop and it was like getting his CEO brain on my company for a very small slice of the whole thing. It was great.

MM: That's amazing. It also reminds me too of the tacit knowledge of just being with somebody who has done the thing really well and you're picking up on their mannerisms and how they conduct themselves and you're like, that's what excellence looks like. It's a pattern-matching thing.

JM: Yeah, totally. We had him negotiate a contract, a $800,000 contract for us, and got him on the phone.

MM: Really?

JM: He did the whole thing as an advisor.

MM: Oh, that's amazing.

JM: I got to listen in and I was like, "Cool. This is great."

MM: Noted. Noted.

JM: Yeah, exactly.

MM: That's really cool. Shifting a little more to your actual career and the things that you're building, I'm curious about your interest area of health, what do you think is the number one issue of our time health-wise, and how are you working on it?

JM: Good question. I think the underlying issue is that around why the US is getting so unhealthy, why the average person is sick and all these sorts of things, is that the incentives in our food system and in our food environment are such that it is driving unhealthy outcomes. You will have people in healthcare, people in politics, whatever, say I can't believe the amount of chronic disease and obesity, overweight that we're having in the country. Childhood diabetes is at a record level and going up. This is crazy.

Everyone's sort of baffled by it. And then you look at the incentives and you go, okay, corn, soy, wheat are by far the most subsidized crops in the entire food system, which means that where we used to have fruits, vegetables, fresh things, now we have highly subsidized products that make their way into things that they should never be in, like soybean oil that counts for almost like, I think it's 15% of American caloric intake today.

Sugar in the form of high fructose corn syrup has gone up like crazy. Why? Because corn is basically a free input, which means that all of these big food companies are using it. Gluten intolerance and gluten allergies have never been higher. This is because wheat has made its way into everything and in its most processed, broken-down component form. And so you see that and you go, these crop inputs are hyper-subsidized and they're making their way into everything.

You look at the food system as a whole and you walk down the aisles of a supermarket, and it is very true that the products that are worse for you are also the cheapest. And the ones that are good for you are also the most expensive. So there's a financial incentive to eat unhealthy.

And then we operate in a healthcare system that basically makes it so that there are no incentives to preventative care, like 99%. It's literally 99% of all money in healthcare goes towards treating people after they're sick. Less than 1% is towards prevention. And so you just look at this system and it's like there's no incentives for prevention. People that want to be healthy have to come out of pocket. They have to drive to Whole Foods, they have to go to farmer's markets, they have to do all these things. They have to do all this research. If you're a student in a school that wants to be healthy, you literally can't. Most school lunches are just bad for you and there are no other fucking options. It's crazy.

And so, one of the things that blows my mind, I know I'm kind of ranting here, is that school lunches are literally a risk factor for childhood diabetes.

MM: Really?

JM: Yeah.

MM: Oh man.

JM: Yeah. Just growing up in a household where you're suffering from child abuse is a risk factor for trauma later in life, eating fucking school lunches-

MM: The default.

JM: Yeah, the default thing is a risk factor for childhood diabetes, obesity, overweight, all this stuff. And so I just think that not only are the incentives so skewed in the direction of making everyone sick and unhealthy, but our default environment is so bad from a health standpoint that you have to be rich, have time, have money, have the space to think about this stuff in order to escape the average outcome. And today the average outcome is six in 10 Americans have at least one chronic disease, and we have 72% of the country is obese or overweight. That sucks. That's crazy.

MM: That's awful. Designed to fail.

JM: Yeah, exactly. And I think that is structural because we have, and I'll get back to what I'm doing now, but I think that is structural because the incentives are to orient people towards making choices that are bad for them and put them in an environment that outputs bad health as opposed to wellbeing.

And so the company that I'm starting now is called TrueMed. What we're doing basically is there's a category of things called HSA and FSA funds, health savings accounts, flexible spending accounts that are tax-free funds that you can put into that can be spent on health and wellness basically. Traditionally, that's meant health as in pharmaceuticals, it's meant health as in surgeries, pills, prescriptions, and things like this. What we're doing is if you look at the body of evidence, there is way better evidence for exercise, treating certain conditions than there is any known pharmaceutical.

There's way better evidence for changing your diet, meditating, and doing any number of things that we call wellness interventions for driving health outcomes than there is for many classes of drugs and pharmaceuticals. And so what we're doing is we're making it so that health and wellness brands, like the ones I've started, Kettle and Fire, Perfect Keto, some of these Peloton Athletic Greens, a bunch of them can accept HSA and FSA funds and consumers can use these tax-free funds to invest in their wellbeing, not just pay for treatment once they're sick.

So as a consumer, you get to save 30 to 45% by using tax-free funds. As a brand, you get to tap into a new source of consumer funds and actually even the playing field by you spend more money to make an incredibly high-quality healthy product, but you have to charge premium for it. Now by using tax refunds, we're hoping that we can level that playing field a little bit.

MM: That's super cool. It strikes me as a really interesting way to expand a market.

JM: Yeah, totally.

MM: How did you stumble across this problem?

JM: Yeah, so my co-founder and I, one of our investors, advisors is this guy Mark Hyman, who is one of the big early doctors of functional medicine and the like. And so he has been a big proponent and been writing, basically issuing what's called a letter of medical necessity. It's a doctor-issued note that allows someone like you to spend HSA, FSA funds on things that can help treat, alleviate, or prevent a specific disease. And so he's been issuing these letters of medical necessity as they're called to help people get nicer mattresses, buy an exercise bike, spend on supplements, whatever, for many years at his clinic.

And so we basically just, he turned us onto the idea and we were like, oh, you can probably build a payments and telehealth platform on top of this insight, issue these notes at scale once you have consumer information integration and the like. And so we started working on this almost a year ago now.

MM: That's amazing. Such a cool mission. If you could change any one thing about how the food world works, what would it be? And maybe broader than food world — health world in general.

JM: Yeah. I think that kind of back to what we were talking about at the beginning, how our parents and grandparents never thought about this and were healthy by default. That's not really true today. And so I think the thing that has changed and the highest leverage intervention that you could make in this system is not educating people. It's not anything but fixing their environment towards one that structurally outputs healthy people rather than sick people of the default.

And so the things that I would do to fix if I could wave a magic wand I would remove crop subsidies for sure. I think that they’re a huge drain and that they mess up almost everything in the food system.

“If I could wave a magic wand I would remove crop subsidies for sure. I think that they’re a huge drain and that they mess up almost everything in the food system.”

The second thing I would do is probably remove, this is getting very granular, but crop insurance is another thing that basically only benefits big farms. It creates structural incentives for farmers to become bigger and to only grow one type of crop. And when you do that, you basically kill the long tail of small farms that have crop diversity, different diversity of inputs.

And I think that we right now live in a food system that is almost entirely driven and dictated by industrial agriculture, and I think that that is one of the biggest problems that we have in our food system today.

MM: Where would you like to shift the power back to? Is it more like the small farms?

JM: Totally, yeah.

MM: The people, the consumers as well, maybe?

JM: Yeah. I mean, think that unfortunately... I think that consumers ultimately have the power. They're just operating in a system that is against them basically. And I think if you look at, to go deep into the food system, if you look a conventionally grown mono-crop output, let's take a tomato grown in an industrial agriculture farm today, that tomato is going to be somewhere between 60 and 80% less nutrient dense than one that was grown 50 to 60 years ago on a small farm without the use of mostly chemical fertilizers.

I think that the nutrient density in our crops is going way down as a function of how farmers have been incentivized to plant, harvest, and do all this sort of stuff on an industrial scale that is heavily reliant on chemical inputs and fertilizers. And I basically think that orienting our food system towards that model of agriculture was one of the biggest mistakes that we've made as a society from a health and nutrition food standpoint.

And I would like to, again, if I could wave a magic wand, it would be reversing back to the older system we had that has much more diversity, many more small farms, much higher nutrient density, and much less reliance on chemical fertilizers and other sort of petrochemical inputs.

MM: Nice. Yeah, it's like incentive design tweaks too.

JM: Totally.

MM: Yeah. I'm still looking for good books and anything on that, but it can be so heavy when you talk about it in theory. I kind of understand why it doesn't exist. Cool. How do you think that we can get more ambitious people working on the most pressing health problems? Why are they not now?

JM: Good question. I think that one of the great things, and one of the reasons I think Silicon Valley has worked in the last 30 years, 20 years call it, is that the most ambitious people in many ways have been pulled towards playing Silicon Valley, like giant outcomes game because they get richly rewarded at the end of that, whether it's in power, money, both, whatever.

“I think that one of the biggest problems in healthcare and health in general right now is that we fundamentally don't have a market that is free, which means that no one makes a bunch of money solving the problem of health or wellness.”

I think that one of the biggest problems in healthcare and health in general right now is that we fundamentally don't have a market that is free, which means that no one makes a bunch of money solving the problem of health or wellness. And because of that, let's say you wanted to solve any of the food problems that I was just talking about, there's no massive pot of gold at the end of solving the small farmer problem right now.

And I think that one of the fundamental reasons why, and I think that you see this in a lot of domains is whenever you have the consumer that is experiencing the service, not be the one that's also paying for that service, you break how markets work. And I think if you look at healthcare, I can get sick and I get a treatment, but this other nebulous sort of entity will pay from that treatment often through a PRB. And there's just all these different layers, which means that... In my opinion, the feedback mechanism in that market is totally broken, which means that it's really hard for that market to self-correct. And so if you introduce something that is health into the system of today's healthcare, let's say that you had a pill that kept someone healthy forever today and it existed, how would you monetize that thing?

Consumers would have to pay out of pocket for that pill, but that's not how most healthcare spend is allocated right now. Most of it goes through insurers. Most of it goes through this cluster fuck of a healthcare system we have. And so I think that that mechanism being broken means that you keep the most talented people out of that space because the reward mechanisms are very unclear.

And then you just have, and this is probably true in education, you ultimately just have a space that's super broken where the best people are just unwilling or unable to operate in that space because it's not that rewarding. And I think that's the really hard thing.

And something Silicon Valley gets so right, is we have in software permissionless innovation with huge outcomes. And because you have huge outcomes, it attracts more people into it who think, oh, I want that huge outcome, and it's this kind of self-reinforcing cycle.

“Something Silicon Valley gets right is we have permissionless innovation in software with huge outcomes. Because you have huge outcomes, it attracts more people who want that huge outcome and it's a self-reinforcing cycle.”

MM: What would you tweak in the health world and the food world to make this better?

JM: I'm definitely a believer in markets in many ways, and I think that the thing that I would try and fix is to remove this sort of weird insurer-payer provider trilemma that I think creates really bad outcomes. Certainly, again, if I could wave a magic wand, the thing that I think is so crazy that we have in the US today is we have... you basically have someone that we know if you were to take someone who is pre-diabetic or going to likely develop diabetes and put them on a ketogenic diet, help them exercise, fix some stuff about their lifestyle, they will probably save the healthcare system, and insurers one to $4 million over the course of their life. And yet, if you want to give that person 100 to $500 a month stipend to eat better food or whatever, there's not really mechanisms by which you can do that today.

Literally, as an insurer, you cannot do that. I think that that is the thing that is just so wildly messed up is there's no mechanism by which this healthcare system can actually pay for people or give people incentives to do things that are better for them. And then we are left footing these massive bills that come when someone is actually sick. And I just think that that market mechanism or that market is just so broken that there's no self-correcting way that information can pass from, oh, if I do X, if I eat better, if I exercise, whatever, that leads to better health outcomes, which means I'm not spending this pool of money, which means that I'm in a better spot going forward.

MM: It's like the loop has been subverted somewhere along the line.

JM: Completely. Yeah, totally. It's super messed up.

MM: Okay. My last question for you. This has been wonderful. I'm just curious, what has been a book or a movie or something that completely changed how you see the world that you recommend?

JM: I don't know if this is trite or not, but when I was in college, reading The Four-Hour Work Week was the first book where I was like, "Whoa, there's so many different ways that you can do this life thing." On my radar was graduate college and work in corporate finance somewhere, or don't, and go get another job at some other large corporation.

I literally didn't have any other conception of ways to do life beyond that. And that was one of the first books where I was like, "Wow, you could travel. You could start an online business. You could do any number of these things." And so that was one of the very first books that massively opened the aperture of my ambition and thinking of what kind of life I could build.

MM: I love that. I feel like my equivalent was #GIRLBOSS by Sophia Amoruso.

JM: Nice.

MM: Similar kind of thing of just opening my eyes to a completely different lifestyle. And also, it's interesting too that you learn about the person too when they're talking about how they approach and think about things. And there's something about, again, it's kind of like the tacit knowledge of their mindset that gets imported.

JM: Totally.

MM: Well, thank you so much for coming on the podcast, Justin. It's been a delight.

JM: Thank you for having me on.

Subscribe for more episodes to come: Spotify, Apple, Google, Amazon, and Overcast.