I left a16z to go build

Lessons from four years investing at a top VC

I left a16z to go build.

I came here almost four years ago now off of a cold email. I’ve done many different things: learned consumer investing from some of the best, spun out to establish the games fund, and built out a16z speedrun as part of the founding team from the very beginning. I’ve been an investor, salesperson, invite tsar, software PM, program manager, growth hacker, product advisor, and therapist. It’s been the most challenging and fulfilling way to spend my late 20s.

As for what’s next, I’ve been thinking about founding a company for a while and wanted to take the jump. But it wasn’t until recently that I stumbled upon a stellar idea and opportunity, one that fits with my roots and passion for science, consumer, and biotech… where I started my career as a biomedical engineer many years ago. We’ll be in stealth for a while but if you’re building in the bio or consumer health space I’d love to chat.

However, the purpose of this essay is to serve less as a memoir and more a source of knowledge. The goal being to condense four years of learning at a16z and convey some of that hard earned wisdom to you: the reader, whether you’re a founder, executive, student, or part time technophilosopher. Some of these lessons are simple, and may even seem trite, but the simplest of lessons are often the hardest to internalize.

So with that, here are five life lessons I learned from a16z.

Don’t follow your passions

The worst advice I’ve gotten is to “find what you’re passionate about.” First of all… what does that even mean? I love science but hated working in pharma. I love golf but would never become a professional golfer. Passions are helpful guideposts but don’t let them blind you.

What brought me to California and a16z was my passion for gaming, but what I learned here is that it makes it easy to miss the forest for the trees if you’re too passionate. It can lead you astray, blind you to reality. Gaming is a great industry and I thoroughly enjoyed my time there, but I didn’t accept the truth that it’s going through a long bear market because of how capital intensive it is, how oversupplied it is, and how much demand there is for consumer attention. The structure of the market makes it much more challenging (but not impossible) to be great.

The other factor is opportunity cost. For a while, I stubbornly resisted learning about AI because it felt too consensus and too hypey. Better to be contrarian than hop on the bandwagon I thought. I came across the country to work in games after all! But my passion made me emotionally contrarian rather than rationally contrarian. And in fact, it made me late to what I now believe is a generational and fundamental shift in technology which was a critical mistake as a venture capitalist.

What I really needed to figure out is what I’m really good at, where my skills are, and how to apply that to the market. Where does the world need me?

I would contend that if you’re really good at something that gives way more satisfaction than anything else. It is important to have an underlying reason for action of course, which could be passion but could be something else. Status, competition, money, family… whatever it is, having some deep desire and something on the line makes you work harder to win and be maximally competent.

I lost that motivation at one point, the “dawg” in me. That’s because I was passionate about gaming, and that was the whole reason I had moved across the country and left everything I knew in NYC. But my passion wasn’t panning out. So what now? I wasn’t doing this for the money, and I didn’t care about the status. It was a weird feeling to be in a dream job but feel the drive fading.

So I had to find other reasons for action, ones that were durable. A few that resonate with me:

• Helping founders, my people, succeed. Nothing better than seeing the team you work hard with and care about so much do well.

• Competition. I’ve been playing games since I was a kid because I love to win, and that drive is still inherently there to this day. Even if I lose, it’s fun to play against extremely competent and intelligent opponents.

• Solving interesting problems. As a former engineer, I miss challenging intellectual problems that stretch my thinking and allow me to fundamentally understand how things work at a deep level.

• Motivating and guiding others. I write these blogs to help the not-so-strangers on the internet, and feel a lot of joy when people tell me I’ve helped them in some small way.

That’s why I’m going back to biotech to become a founder. Because I have a personal history with diabetes and Alzheimer’s in my family, I’m technical from years in the biomedical field, and if I can get this product to market I’ll help a lot of people in a meaningful way. It’s not necessarily a passion, but a mission I care about and can execute on. Losing my passion made me rethink why and how to become uniquely great at something.

Becoming n of 1: a monopoly of the self

There is a focus at a16z on strengths rather than lack of weakness. This was quite a change from both college and McKinsey where the focus was more on becoming well-rounded individuals, especially at my alma mater Columbia where the Common Core encourages students to become a worldly scholar.

But focusing on strengths has several main advantages:

• If you’re at a job, having things that only you can do makes you irreplaceable and gives you more leverage with your bosses

• More broadly, markets are competitive. Commodity skills will degrade in value. So having uniqueness allows you to command a higher valuation (salary) in market

• If you’re a founder, you have the deck stacked against you. Larger companies have more people, more money, and more distribution. So the only way you win is by leveraging your team’s unique talents to gain an edge.

Think of yourself as a startup in the market. The goal is to become a monopoly. This will enable you to have a moat (job security), pricing power (higher salary), and leverage (move where you want and work how you want).

So then, how to become a self-monopoly? I think the best analogy is actually skill trees from old roleplaying games like World of Warcraft or Runescape. You might have stats like strength, charisma, intelligence, wisdom, or luck. These actually map to modern skills pretty well too: maybe you have high strength so you become an athlete or high charisma so you become a comedian or salesperson. The goal is to become “best in class” and have the skills and stats to become a top level player.

But classes come in different types, some are glass cannons and some are a mix. A glass cannon might look like a wizard or brute who’s very high on intelligence or strength respectively. But a blended role might be an assassin or a paladin who’s pretty high on a few different skills. So for the real world that might look like a software engineering savant (wizard) vs. an excellent CEO (paladin).

For me some of the skills were learned, some were realized, and others were unearthed. I had to learn good PM skills from my colleague Josh Lu and consumer investing / psychology / growth hacks from Andrew Chen. I realized that one of my strengths was forming close emotional bonds and trust quickly with founders, which would help me win deals and help the company grow. And to my surprise, I use a lot of the writing skills that were drilled into me in high school and the technical biomedical understanding I learned in college.

So figure out where you are in the market, and decide how you become irreplaceable. The way to do that is to think for yourself instead of letting others dictate for you.

Independence of choice and independence of thought

Most people believe they think for themselves when they actually rely on the decisions of others. You buy the stock that everyone else is talking about even though you know nothing about the company. You work at a job you don’t really like because it’s high status and a lot of other smart people wanted it. You buy a fancy car even though you don’t like driving.

Decision by mimesis: we want and think based on how other people want and think. I’ve been prey to this myself many times. Examples would be my choice to go to McKinsey after college, and even several deals I’ve done here at a16z. And most of the time, people who give you advice are intelligent, thoughtful, and want the best for you.

But this is a mistake.

I understand now why older people prioritize “critical thinking.” It is very challenging to form opinions that are truly your own, synthesizing what other people say but not listening to them blindly. I found this very challenging in early stage investing coming from an engineering background, because there was often very little data to go off of and you were wrong much more often than you were right.

I needed to learn how to get to conviction quickly, gather what data I could from questions, references, and research, and form my own opinions about both the founder and the business. People think about VC as a contrarian business but it’s actually the opposite.

It’s all group think.

In VC there are structural rewards for mimesis. Early stage investors rely on other later stage investors to mark them up if their company does well. And so you’re always guessing what might be “hot” in the market in a year or two. VCs also often get rewarded for winning hot deals that everyone hears about, sometimes regardless of whether the business itself is outstanding. The incentives are strong. That’s what makes this whole VC game challenging, because market consensus and an oversupply of capital means that prices and risk go up.

Slowly developing the ability to think critically for what I believe, having the conviction to take action, and then being willing to back it up in the face of criticism. That’s what I learned. It’s honestly really fucking hard. When you stick your neck out, when other very smart people tell you no, when even your friends question your judgment. That’s when you know whether you have real conviction.

Self-discipline and self-measurement

Two truths. Very simple but very powerful.

1. Great things are built from small steps

2. What isn’t measured won’t improve

I learned these well from my former colleague Jordan Mazer who I respect immensely. We all know that we should have more discipline: wake up earlier, go to the gym every day, watch less brainrot tiktok. But putting it into practice requires much more mental fortitude. What I observed was that every day, Jordan would be at the office at 6AM with a social media post up by 9AM. He didn’t particularly like social media or talking in public, but he knew it generated results: views that resulted in signups for his job board turned into hires at our startups.. So now he has 100K+ followers and tens of thousands of people on his newsletter.

I believe that how you do anything is how you do everything.

It’s important to practice the discipline everywhere in your life. If you skimp at the gym you’ll probably skimp the last few emails at work too. So whether it’s running every day or writing every week or reading on the go, I learned to build up small habits everywhere that I believe will translate to real results.

And the second piece around measurement is equally important. I needed to keep myself accountable. When no one’s watching and it’s just me, especially now that I’m a startup founder. The company is myself. There’s no manager, no boss, and not even any customers yet. So whether you’re using substack analytics or whoop fitness scores, I find it so crucial to be honest with myself on how I’m doing.

In order to do that, you may need to change your attitude.

War-time vs. peace-time

a16z is a very serious place. First class business in a first class way.

I think this seriousness is best embodied in the war and peace metaphor. It was a very stark transition for me coming from Riot, which was most certainly a peace time company when I was there. There’s a pirate themed cafe. There’s a massive PC bang with N64s for Super Smash and Mario Kart driving machines. An excellent top end cafeteria. Statues of all the champions. A typical day might look like: come in at 9, grab a coffee at Bilgewater, work till 12, break for lunch with friends and colleagues, play a game of League, head back to work till 6:30 when dinner is served, and then play a few more games after dinner.

It was embodied in the culture too at Riot. People take work seriously but there’s less urgency. There was a sense of “bringing your whole self to work” because you’ll game together and get to know each other outside of the work context. You’ll care about each other and get to know each other on a deeper, personal level. It was honestly… very nice.

On the flip side, I learned at a16z what it meant to be in “war-time” mode, which has honestly prepared me to become a good founder. High urgency. High standards. Things must get done quickly and flawlessly. Punishment and reproach for getting things wrong. There’s camaraderie for sure but the team functions more like the military in the communications (efficient), structure (hierarchy), and strategy (play to win).

The benefits of having a war-time attitude are clear especially if you’re playing in a very competitive space. You need to have the entire team playing to their strengths and pulling in the same direction to generate the best results, Steve Jobs style. However, it also means that you won’t be as close to your colleagues by design, and the culture itself will be aggressively meritocratic.

The most important piece of the war-time attitude ties into what I mentioned before: generating results. Real results, not fake shit. No KPIs or random PM metrics, but things that move the business forward. Because in war, intentions do not matter. What matters is who won and who created history.

Onwards and Upwards

I’ve made a lot of mistakes here, but the main thing I took away from my four years at a16z was wisdom. The wisdom to know that I was fearful of making decisions and hard choices. The wisdom to find conviction and choose. The wisdom to understand the game I was playing and the wisdom to leave and pursue the next journey.

If there’s one stat on my life character sheet I prioritize about all else, it’s this. Decisiveness. The ability to make choices.

I hope you make good ones too.

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Thanks for reading! If you made it this far, there’s a few things you can do to stay in touch. Also a little easter egg for you from the team for SR001 all the way back in 2023.

• Please consider subscribing to support my work! I plan on writing weekly and will have some paid-only posts that are more in depth.

• I’ll be moving to SF very soon so if you hear of good spots / rooms opening up in Marina / Pac Heights / Russian hill do let me know! SF friends looking forward to seeing you more soon

• If you need career advice, fundraising guidance, or feedback on consumer / growth / healthcare / games, areas where I have a lot of expertise, I’ll be doing a few paid consultations (30 min, 60 min) to pay the bills while I build my startup. If I can be helpful to you feel free to book.