30 Lessons at 30
This year, I’ve received a lot of outreach from investors leaving their firms to start their own—many times more than any other outreach I get. Usually, they want to talk about the different investors and strategies I’ve studied, and see how they can differentiate theirs. The industry seems to be at a crossroads: prior to this year, the most common question I got was whether people could invest with me (I haven’t taken on any external capital to date, so I haven’t been able to help with this).
As with any investment, one of the first questions I ask is: “What’s different?” For people who are obsessed with edge, moats, and differentiation in businesses, they never seem to have a good answer for themselves.
Earlier this year, I had a realization about my own investing and how it relates to who I am, so I wrote a memo on it and shared it with those who asked. They all asked me to publish it so they could share it with their friends and/or partners, so here it is. It’s different from what I usually publish here because it’s not on a person, a company, or an industry, but how I personally think about investing and how I found my form.
Behind the paywall is the tactical half: how I work and how to reach out if you’d like to explore working together. After a decade and a half of working almost entirely by word of mouth, I’m making room to take on a few more partners on the research front.
Memo
Date: July 20, 2026
Re: 30 Lessons at 30
I turned 30 earlier this year. In the weeks before, I started writing a memo about it. It was one of those 30 lessons at 30 years old type of memos. As cheesy as they are, I’ve always enjoyed reading them, and always wanted to write one of them. I’ve actually done a version: 50 Lessons from 50 Tigers—although I wanted to do a proper birthday one.
As I wrote the lessons, themes began emerging. I changed the essay from 30 lessons to 30 frameworks, with each framework having three sub-lessons. As I agonized (yes, agonized) over each framework, each lesson, I realized there was actually a lot of overlap. I decided, once more, to change the essay. I would compress the lessons from 90 to 3. One for every decade I’d been alive.
I got stuck at four.
The four principles are:
At the end of the day, it’s all about the people.
Think for the long term.
Choose your environments carefully.
Think for yourself.
As I thought about each principle, and the principles as a whole, I realized something: these four principles, in principle, were the same as my investing principles.
I’ve spent nearly two decades studying investors, founders, and operators, building up a latticework of frameworks to guide my investing. However, it wasn’t until the past two years that I finally landed on a framework that worked for me. But it wasn’t just one framework—it was a combination of two frameworks, each made up of a number of sub-frameworks*.
The framework has four components:
Founder mindset.
Reinvestment opportunity.
Market power.
Variant perception.
The realization made me sit up. In a way, the principles seemed to match up perfectly. Almost too perfectly. I wondered: was I overfitting?
I wasn’t. The principles don’t line up perfectly, but they do line up.
It’s all about the people <> Founder mindset.
Think for the long term <> Reinvestment opportunity.
Choose your environments carefully <> Market power.
Think for yourself <> Variant perception.
The life principles are slightly more general, and the investing principles are slightly more specific, but the underlying principles are the same.
There’s a lot of nuance, so let me walk through each pair one by one.
It’s all about the people <> Founder Mindset
Before I get into people, I want to share one word, and one quote, that I love.
The word is sonder: “the profound realization that every random stranger is living a life as vivid, complex, and real as your own.” It’s also, in a sense, what makes a market—two people, two worlds, two different views on the same thing.
The quote is from Before Sunrise: “If there’s any kind of magic in this world, it must be in the attempt of understanding someone, sharing something.” This creates empathy and leadership. It allows for consensus building, for learning. I believe you can learn from anyone, especially those who you most vehemently disagree with.
Put them together, and the result is chemistry. In chemistry, you combine two volatile elements and get something new. Now replace “elements” with “people.” When two people, each with their own worlds, meet and try to understand each other, worlds collide and create new perspectives that neither had alone.
It’s why I’ve found my friendships to be one of the most rewarding aspects of my life. My friends span poets, artists, professional athletes, investors, founders, salespeople, engineers, scientists, and more. Some are disciplined to the minute; others chase serendipity and let it drag them around. I’ve found a few common throughlines: curiosity, adventurousness, and resilience.
I look for versions of the same things when I evaluate founders and management teams: a child-like mind, humor, and obsession. The child-like mind is full of wonder, always learning, and constantly exploring. It is open to the new and unfamiliar, and thinks from first principles. Humor signals intelligence, charisma, and social fluency—a read on culture and people that leading others requires. Finding humor in a difficult situation speaks to perspective and calm. Obsession begets a higher purpose, a willingness to work hard; you can’t be an artisan if you don’t obsess over the smallest of details. With obsession comes focus, which compounds into expertise.
The founder mindset allows an organization to retain the internal energy, focus, and adaptability of a founder, regardless of size. Founders need to continuously evolve—just as the organizations they steward have to.
To be clear—I don’t only evaluate founder-led companies. I want to see these traits in every stakeholder, from the founders to the executives to the employees to the board members. You don’t have to be a founder to think like a founder, but you do have to act like one. Without a founder’s mindset, companies become bloated and inefficient.
One of my favorite examples of an operator with a founder’s mindset is Joy Covey, who was Amazon’s first CFO. I wrote about her here (Joy Covey: The Deep Keel).
Think for the long term <> Reinvestment Opportunity
One of the first books my dad ever gave me was Stephen Covey’s 7 Habits of Highly Effective People. To be honest, I couldn’t tell you what even one of those habits are. But what I did take away was that actions, repeated, become habits, which over time, compound into a successful life.
Now, this doesn’t mean that I believe humans have to be creatures of habit in order to have a successful life. In fact, many of my most meaningful experiences and relationships were the result of one-off, crazy, obviously bad decisions. Sometimes they just seem bad—other times they actually are. Most of my decisions are centered around three things: curiosity, serendipity, and family.
A single reckless yes can compound for a decade the same way a small habit can. So where I’ve landed is this: people say that life is the sum of your experiences—I believe it’s the sum of our decisions. Like music is made up of high notes and low notes, life is made up of good decisions and bad. And like a song comes together from all its notes, a life compounds from all its decisions. Those decisions are how we interact with the world, with other people.
And the world is more malleable than we believe—I’ve seen firsthand people single-handedly will things I thought impossible into existence, whether it be an idea, a relationship, or a company. Some people call this a reality distortion field—I call it calculated delusion. But as Steve Jobs said, “the ones crazy enough to think they can change the world are the ones who do.”
We can change the world through our decisions—and as Admiral McRaven once said, “If you want to change the world, start by making your bed.” The idea is that a small task like making your bed encourages the next, which in turn encourages the next. Small tasks compound. McRaven’s speech went viral—and for good reason. But almost nobody does it, because humans fundamentally struggle to grasp exponentials. Snowballs start small, then accelerate. Little actions compound. When people don’t see immediate results, they often give up. Those who push through, often get to a point where they see rapid growth.
This is equally as true in your life as it is in investing. If you want to feel (and look) good: eat healthy, exercise often, and sleep regularly. If you want to make money, invest wisely, spend carefully, and manage your taxes. Decisions compound. So does capital.
So when evaluating businesses, I look for a strong reinvestment opportunity, where a business can generate strong, predictable free cash flow, earn sustainably high returns on invested capital, and has ample opportunity to deploy that cash at comparably high rates of return. This is generally done through the creation of value, new geographies or business lines, or riding secular shifts that are just taking off. Without strong reinvestment opportunities, a company’s returns will deteriorate and eventually be competed away.
One of my favorite examples of a company with a large reinvestment opportunity is Alphabet. I wrote about it here (Alphabet is Berkshire Hathaway 2.0).
Choose your environments carefully <> Market Power
Mencius’ Mother Moves Three Times is a Chinese idiom about the power of our environments. In it, Mencius is a young boy who mimics the people around him—living next to a cemetery, he mimics gravediggers and professional mourners, digging mock graves and wailing in imitation funeral processions. His mother moves them next to a marketplace, where he mimics street vendors and butchers, haggling and shouting boastful selling tactics. They then move next to a school, where he mimics the teachers and students. This is where they settle down.
This doesn’t mean nurture is more important than nature—it’s that your environment matters just as much as your nature. And unlike nature, you can choose it, from the people around you to where you choose to live to where you choose to work. All of it shapes you.
Some people believe they’re dealt a hand and fated to play it. I’m not saying it’s easy, but it is possible, and that possibility is the American dream. If you’re in a toxic environment, you have two real options: change it or leave it. You can stay, of course—most people do—but staying is a decision too, and the environment compounds against you.
So find a place with positive network effects. Negative ones make leaving even harder. You may not be able to change your environment, but if you don’t try, you definitely won’t.
The same is true in investing—maybe more so. Here’s the uncomfortable part: your environment matters more than your effort inside of it. Meaning which game you choose to play matters more than how well you play it. It shows up at every level. At the highest, for an investor, it’s the strategy: quant, value, growth, macro, equities, credit, venture, private equity or something else.
Stan Druckenmiller has famously said that “People always forget that 50% of a stock’s move is the overall market, 30% is the industry group, and then maybe 20% is the extra alpha from stock picking.” Put differently: 80% of a stock’s move is the environment (market and industry), and only 20% is the pick itself. And even that 20% isn’t really yours; as Druckenmiller adds, stock-picking is full of hidden macro bets. So the environment matters even more than the 80% suggests.
The same logic runs down through every level. Certain asset classes, such as technology over the past 20 years with its near-zero marginal cost, have carried structural advantages. Within industries, there are further advantages still. And at the company level, Warren Buffett has noted, “The single most important decision in evaluating a business is pricing power.”
When I look for market power, I’m referring to structural characteristics of industries and companies that allow an organization to build and sustainably hold a dominant market position while maintaining market share or margins and generating cash flow. The conditions for market power create the potential for persistent differential returns, even in the face of a fully committed, capable competitor. This comes in the form of competitive advantages such as increasing returns, scale, and counter-positioning. Without market power, competitive forces inevitably arbitrage away any temporary advantages.
The open vs closed source AI debate is a real-time case study in market power. I wrote about it here (The Structural Case for Open-Source AI).
Think for yourself <> Variant Perception
As I said at the start, sonder is one of my favorite words: everyone lives in a different world. It’s what makes a market. So what’s obvious to you may be invisible to someone else, and vice versa. And that’s not nothing: even the people I most vehemently disagree with, whose logic I find holes in, genuinely believe their own reasoning. Almost no one thinks of themselves as the villain. The alternative is worse: they’ve stopped thinking for themselves and are just following orders.
It’s why being yourself is so important. If everyone thought the same, markets wouldn’t exist—and the same is true of people. So rather than trying to be the best, be the only. That doesn’t mean forcing anything. Bees come to a garden you’ve tended; you can’t summon them, but you can do the work that draws them in. You attract what you put out. Go with the flow—but tend the garden.
Learn from others: good artists copy, great artists steal. Most people hear that as license to copy, but the reverse is true—you take the raw material so you can make it your own. You have to. For example, my framework was originally two separate frameworks combined (not to mention the sub-frameworks). Do not, under any circumstance, blindly follow others (i.e., you can borrow investment checklists, but eventually you have to make your own).
In the investment business, where people are paid for their judgment, it’s even more important to be yourself. Only by being yourself can you be consistent and have conviction—in your investing and in who you are.
When it comes to thinking for yourself in investing, people often talk about being contrarian, or having variant perception. But they usually only mean one thing by it: direction.
At its core, variant perception is about seeing what others don’t. There are two types: 1) what you see, and 2) how you read what you see. The first is observation: you notice something others don’t—and in the moment, you can’t quite believe they don’t see something so obvious. If you turn out to be right, they’ll call it brilliance later. The second is interpretation: how you read what you see. It takes three forms: 1) direction (opinion on the opportunity), 2) magnitude (size of the opportunity), and 3) conviction (confidence in the opportunity). Most people think only about direction; few think about the other two, which matter just as much, if not more.
All of these come down to the same willingness: to hold a view the crowd doesn’t. And that’s getting harder. People have CNBC blasting in the background at all times, are constantly on Twitter looking for alpha but finding noise, and have AI summarizing (and hallucinating) everything for them. But when we stop thinking for ourselves, we become sheep. We lose any sense of agency and we stop taking responsibility for our actions. I’ve written about the dangers of outsourcing our thinking here (AI Isn’t Coming for Your Mind. It’s Coming Through It.).
Putting it all together
When I look back on my life, almost all of my decisions have been based on these four principles. Early on, my parents put me in sports programs and had me test into one of the best academic K-12 schools in the world. But from then on, I made my own decisions—not by rejecting the best, but by finding the best of the roads less taken. I transferred to one of the best athletic high schools in the nation. I then chose not the most prestigious college, but the one where I felt I would be most uncomfortable and learn the most. Then I chose not a traditional pathway, but to go abroad and attend one of the most rigorous graduate programs in the world. I dropped out, in a country and a program where dropping out is not celebrated like it is in Silicon Valley, or even the US. I eschewed a regular full-time job, choosing instead to research while pursuing my interests, taking on special projects, internships, or even jobs when I wanted to go deeper into a field.
All of this was to the chagrin of my parents and the confusion of my peers. But none of that was some grand strategy. It was just me being me, looking for the most interesting people, thinking for the long term, choosing my environments carefully, and thinking for myself.
And it’s shown up in my investing too. Two examples of this are my still-private investment memo on Google from May 2025 that made it my largest position, and my now-public thought experiment on SpaceX (SpaceX is building a planetary starter kit). The crux of the latter memo is that while SpaceX is overvalued by any standard valuation method, the more interesting question is why people are willing to pay seemingly irrational prices for it. It wasn’t a stock pitch, but an attempt at understanding that question.
Even so, I was expecting a lot of pushback on it. Instead, I was pleasantly surprised by positive feedback from a wide range of people—retail traders, finance students, first-time founders, and even a few legendary investors you’d recognize if I named them. It wasn’t all positive to be sure—one of the legends, a quality-focused investor, dismissed it as “a fantasy.” But most took something from it, and each took something different: a macro investor focused on the central question, a value investor on the sheer size of the opportunity, a founder on the importance of articulating a big vision. That range, more than anything, is why I think it resonated.
Founder mindset – The piece articulates how to paint a vision, references Elon “the collective,” and decisions that can only be made with a true owner’s mentality.
Reinvestment opportunity – The piece tackles perhaps the only truly infinite market in the world: space. And when thinking for the long term, humans have to become multiplanetary in order to not just thrive, but survive.
Market power – The piece discusses the potential for planetary monopolies. To go where no one else is (new planets) and be vertically integrated.
Variant perception – The question shouldn’t be whether SpaceX is fairly valued, but why so many people buy it at seemingly irrational prices. It’s variant perception on all three axes: direction (space is a real market), magnitude (it’s bigger than people think), and conviction (belief that runs well ahead of the current numbers).
None of this converged because I set out to make it converge; it converged because the life and the investing were both honest expressions of me. That’s the part you can’t reverse-engineer, and it’s the part most investors never reach.
Finding Your Fit
Why do so few investors find their fit? There are a number of reasons, but two stick out: 1) the industry filters it out, and 2) finding it means knowing yourself—which can be deeply uncomfortable.
To me, public equities investing is one of the purest forms of idea expression. You have an idea, you put capital behind it, it plays out according to your thesis or it doesn’t. The market doesn’t care about your feelings. It doesn’t care about your ability to find or strike deals, it doesn’t care if you are an excellent operator, it doesn’t care about how sound your research and logic are.
But you have to be careful, because the market’s verdict is noisy, and it can and will lie to you in your favor. You can be right for the wrong reason—the stock can go up, but not for the reason you believed. This is not sustainable nor is it repeatable. You have to be right for the right reason: the world turned out to be the way you thought it was. Your idea mapped reality. That’s the thing that repeats—not whether you made money or not. Only you can know, and only if you’re honest at exactly the moment you least want to be—when you’ve made money.
But investing isn’t just the expression of a single idea (or a portfolio of ideas), it is, at its core, an expression of who you are. What kind of strategy are you employing? How do you find ideas? What kind of ideas speak to you? Which ideas do you build conviction around? What do you actually care about vs what do you say you care about?
It’s why one of the most interesting questions in investing is around fit. Investors love to talk about edge—whether it’s public equities, venture capital, or anything else. VCs are obsessed with it: product-market fit, founder-market fit, unfair advantages, etc. Public equity investors talk about competitive advantage, moats, differentiation, etc.
But they never turn that question on themselves. Here’s the paradox: investing is one of the most competitive industries in the world, and one of the least differentiated. Most investors are capital providers with no sustainably differentiated strategy—the strategies are largely identical, just described differently. Why?
There are a lot of reasons this is true, not least because it’s an uncomfortable question people prefer to avoid truly facing. But there are some structural reasons too.
Investing is an apprenticeship business—you learn it standing next to someone. It’s incredibly difficult to land a buy-side job, and when you do, you’re often pigeonholed into it. Your job is not to become the best investor, but become the best analyst for your Portfolio Manager. Many analysts I know don’t pitch the best stocks they can, but rather what they think their PM will like. They absorb a style they didn’t necessarily choose, then get pigeonholed in it.
Eventually, these analysts may decide to spin out. Most of the time, it’s because they want to do their own thing. They want to invest on their own terms. This is true whether they’re at a single manager fund or a pod shop. But fundraising is brutal, and “new” strategies are difficult to underwrite. So people end up pitching on the old strategy plus a twist, rather than what is truly the best version of investing you can think of. It’s effectively the same shape wrapped in a new name.
The results are a handful of templates. In public equities, you have the Tiger long-short model, the pod shop risk-management model, the quality long-only model. In venture, you have differentiated deal flow, brand signaling, platform value-add.
Since the strategies are all more or less the same, the key differentiation comes down to you. What makes you unique is what can make your strategy unique. So more important than the strategy is the strategy as an expression of you. When it’s truly yours, you get two things that can’t be bought: consistency and conviction.
I’ve spent nearly two decades studying investors, founders, and operators, and if I’ve learned one thing, it’s that there’s no single right way to invest. Druckenmiller trades. So does Tepper. Jensen seeks beautiful businesses. Rainwater sought disruption. Moore restructured bankruptcies. Whorton looks for the evergreen. Emery chose fixed income. Pollock is opportunistic. Munger focuses on climate. Loeb goes activist. Collins targeted sustainability. Kravis buys companies outright. Shleifer went global. Volent allocated to investors. Duca avoids complexity; the SFI crew embraces it. Simons turned markets into math. In fact, that’s the whole point of A Letter a Day. None of the best investors play the same game, and none of them could ever play each other’s. Each one found the version that fit.
But most investors never do, and you can see it in how little they can explain about their process. Almost every manager will tell you their biggest mistake was selling a winner too early—and the research backs it up: professional investors’ sell decisions have been shown to systematically underperform even a random-sell benchmark. Ask them how they size a position—outside of quants with hard risk limits, nobody has an honest framework. It’s always “conviction” or “feel.”
That’s not necessarily a bad thing, but it’s worth being honest about. The job is judgment. The flaw is running a strategy you don’t actually believe in, or one that isn’t suited to your personality. When your investing is an honest expression of yourself, only then is it truly sustainable. Because people can fake who they are for a long time, but they can never do it forever, especially if they face difficult times (people say to buy low and sell high, but usually end up buying high and selling low).
So how do you actually find your fit? I’ve only ever seen two ways: 1) truly understand yourself and design a strategy around what you find (both your talents and your limitations), and 2) study widely—read everything, listen to everything, and talk to as many people as you can—and pay attention to what resonates, then assemble your own.
I found mine through the second route. If I had to do it again, I’d go looking for the first one on purpose. It took me over a decade, but I consider myself lucky—most people never find theirs at all.
The One Question
There’s an old parable David Foster Wallace liked to tell. An older fish swims past two younger ones and asks how the water is. They swim on for a while, and eventually one turns to the other and asks: what’s water? The hardest thing to see is the thing you’re swimming in. In investing, that’s your own strategy, the reason you’re drawn to the ideas you’re drawn to. In life, it’s you.
I opened this by defining the word sonder, the work of seeing that everyone else is as real as you are. This is the harder version: seeing yourself clearly enough to know what actually fits. Do that, in your life and in your work, and they stop being two questions.
There’s a million ways to make money. You just need to find what works for you.
*A note on the frameworks
I mentioned earlier that my framework is two frameworks joined—one I learned whole, and one I assembled from pieces:
Fundamental Building Blocks (Cristiano)
Founder Mindset
Reinvestment Opportunity
Market Power
Variant Perception
Observation (Greg)
Interpretation
Direction
Magnitude (Dan)
Conviction (Joe)
The fundamental building blocks—Founder Mindset, Reinvestment Opportunity, Market Power—I learned from Cristiano Souza. He calls them the “drivers of compounding.” My framing is for me.
The first time I heard it, something clicked. The more I thought about it, the more elegant I found it. It was only three characteristics, but you could hold any business up to them. I tried to poke holes. I couldn’t. But the more I applied it, the more I felt something was missing.
His framework is robust for evaluating businesses, but not for knowing when my view differs from the market’s. To him, over a long enough horizon, variant perception matters less; the business compounding is what drives returns. He’s right, of course. But I like to fish in one of the most volatile markets (technology), and I want a higher margin of safety.
Variant perception gives me that. It gives me the conviction to initiate a position when the market thinks it’s all but dead, and it gives me the peace of mind to hold a position when the market is moving against me. Cristiano may not care much for variant perception, but I need it.
This one I had to assemble on my own. Direction was a given—it’s talked about ad nauseam. The rest of the structure above, I only saw over time—through three distinct people.
From Joe Philleo: conviction. You can be contrarian in two ways: 1) Having a different POV than the mainstream, thus making different bets that seem delusional, or 2) Having much more conviction than the mainstream, thus making much larger bets in a way that seems overly aggressive.
Then Dan gave me magnitude. He shared that most people ask only whether they see something the market doesn’t—but that you can also have a variant perception on the size of the opportunity. That’s what most people miss. At first, I thought magnitude was just conviction wearing a different hat; it took me some thinking to realize that they’re not.
Underneath it all is observation itself, which came from my friend Greg. Why are things that sometimes seem so obvious, whether investment-related or not, sometimes so hard for people to observe? Sometimes you look—literally just look—and there it is. And that something can sometimes be everything.
If you’ve made it this far, thank you for reading. This memo was the philosophical half of something I’ve been circling for a while.
Behind the paywall is the tactical half: how I work and how to reach out if you’d like to explore working together. After a decade and a half of working almost entirely by word of mouth, I’m making room to take on a few more partners on the research front.