Having a Conversation With Myself: 2025

Revisiting My Own Ideas

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I’ve been writing consistently now for exactly four complete years. Every week. Including this week, that’s 520K+ words across 208 weeks. By far, one of the most consistent things I’ve ever done.

And each year (2022, 2023, 2024), I’ve ended with the same annual tradition of re-reading everything I’ve written over the course of the year and looking for consistent themes. The only difference is that I’ve always called it “Having a Conversation With Yourself.” This year, I changed it to “Having a Conversation With Myself.” It’s a subtle thing, but feels closer to the core purpose of why I write. I don’t write for you. I write for me. Though I’m happy to have you along for the ride.

Every year, its the most valuable exercise for my writing. I’m consistently surprised by what I find. This year, in particular, I found myself appreciating my writing and ideas. That may sound silly or self-serving, but I’ve always been a fairly self-critical writer. And this year was, candidly, probably my weakest year for writing in terms of quality. But those times when I did write things I was really proud of, I found myself revisiting them with fondness.

So, without further ado, here are the themes I saw popping up in my writing again and again.

Talking To Myself

1. Why I Write: I’ve reflected several times on my particular brand of “panic writing.” But this year, in particular, I found myself appreciating the psychology around why I write and what I gain from it.

2. In A World: This is a small one, but I kept finding myself using this same phrase. “In a world of X, be a Y.” It only happened a few times, but it felt compelling enough to be noteworthy.

3. Adventure Capitalists: This was one of my favorite phrases that I stumbled on, thinking about different characteristics of Adventure Capitalists, or Conviction Capitalists. It’s a theme I hope to spend more time on in the years to come.

4. Noisier Than Ever: Across a broad swath of different meanings, I kept coming back to this idea of noisiness. Noise in terms of competition, media, hype, hucksterisms, and everything in between.

5. Building Things Worth Building: There is this purity in building that I continue to circle around in my writing. It isn’t anti-capitalist, it isn’t anti-VC. It’s an acknowledgement that there are many ways to build a company, but increasingly there seems to be a plethora of energy and pressure towards a particular way of building a company that, to me, is not at all sustainable. The things not worth building.

6. The Job of a Venture Capitalist: A surprise to no one, reflecting on the job of a VC is a consistent trend in my writing. But this year, in particular, I wrote a lot of pieces that felt like they specifically addressed day-to-day questions of a VCs job. Likely, because most of them were literally inspired by conversations with investors earlier in their career.

7. Finding Yourself: Thanks to my reading of “The Courage To Be Disliked” this year, I felt particularly drawn to trying to unpack my own psychology and emotions more so than usual.

8. Nuance, Nuance, Nuance: I’m also always writing about nuance. I believe its one of the most difficult concepts to grasp. And in a world that is getting noisier and more partisan, that nuance is only going to get more elusive.

9. Hyperlegibility: Big thank you to Packy McCormick for introducing me to my “word of the year.” This impacted my thinking about media, cognitive security, the evolution of venture, and tech as a whole. The implications of a particular industry or trend becoming more legible are transformative.

10. Interdependencies: A smaller, but mighty theme that I touched on a handful of times was the criticality of interdependencies. How forces shape each other, whether we like it or not.

11. Future Posts: Another small one, but something else I noticed I did a handful of times was hint at an idea that I’d like to unpack further in the future. Who knows. I’m lousy with ideas for pieces I want to write, but haven’t. But maybe keeping track of these will become fodder for future posts as I flush them out further.

Why I Write

All of this has reinforced for me the power of writing to force reflection on the things I’m thinking about. The number of times I find myself surprised by what I’m writing; that’s the real value of spending time doing this each week. (The Future of Investing 101)

“I’ve also written over and over and over again, reflecting on my own writing process. One of the things that stopped me from writing in the past was the feeling of shouting into the void. On top of that, I had a feeling of perfectionism. If it didn’t feel like a truly good piece, it wasn’t worth publishing. But if I had let that feeling drive me, I would have published maybe 9 pieces in the last 3.5 years.” (Creativity as Connectivity)

“For most of my life I’ve been obsessed with note taking. I often feel the pressure of the knowledge I’ve amassed. Perspectives, playbooks, processes. They all jumble together, and I often feel them tumbling out. When I talk with people, I often say “here’s three threads that makes me think of.” And in those moments when I can share a snippet of thought or recited wisdom, I feel ever so slightly unburdened. Sharing the knowledge both justified why I carried it in the first place, and allowed me to alleviate the load — sharing the responsibility with someone else.” (Don’t Die With Your Music Still In You)

In A World

In a world of consensus conglomerates, be a conviction capitalist. (Conviction Capitalists)

In a world of Content Creators, be a Content Conceptualizer. (A Latticework of Knowledge)

In a world of normativity-seeking systems, anchor yourself in beliefs. (Build What’s Fundable)

Adventure Capitalists

The combination of an emphasis on leanness and increasing attention paid to whose money is being managed all represent a common counterpositioning: these investors don’t want to be asset managers; they want to be adventure capitalists. (Venture Capital Unbundled)

Lovers of the art and history of venture capital remember with reverence stories like Don Valentine investing in Atari. In the book, The Power Law, it tells it so well: “In late 1974, a few weeks after his visit to Atari’s factory, Valentine made a decision. He was not going to invest yet: Atari was too chaotic. But he was not going to walk away: the potential was too terrific. Instead, he would get involved cautiously, in stages, and he would start by rolling up his sleeves and writing an Atari business plan.” That’s the kind of adventure capitalism that used to personify venture capitalists of the Arthur Rock generation. People taking risks alongside founders to help build generational businesses. But now the industry is largely defined by pansy ass asset managers who did banking or consulting to shore up their safety nets before taking “pretend risk” with fungible “LP Daddy” money. (Venture Capital Unbundled)

Samir Kaji had a great piece a few weeks ago called How should LPs think about VC fund size? In it, he makes this point: “The rise of institutional seed funds, the emergence of mega-platforms, and the sheer scale of the industry have turned venture capital into a collection of distinct strategies. Yet many LPs still use a monolithic lens to assess venture capital, which results in the ongoing comparison of “large vs. small” VC funds, which misses the point—these aren’t just different fund sizes; they’re fundamentally different economic products with unique risk-return profiles and business models.” And the problem with that is not that one strategy is good, one strategy is bad. It’s that they’re different. I write all the time about how the stupider game to play is just to not know that you’re playing different games. Instead, the real problem is that one specific strategy is eating the entire conversation. As I wrote about in The Unholy Trinity of Venture Capital, “as venture capital evolves it often tilts not in the direction of what you think it should be, but what the loudest people with the most capital decide they want it to be.“ (Venture Capital Unbundled)

“VCs have, increasingly, started focusing on incremental outcomes rather than ultimate outcomes. Rather than the VCs of old, who are getting their hands dirty, today they’re often just taking an allocator approach. It reminded me of one of Steve Jobs’ lessons he wanted to pass on right before he died: “I hate it when people call themselves “entrepreneurs” when what they’re really trying to do is launch a startup and then sell or go public, so they can cash in and move on. They’re unwilling to do the work it takes to build a real company, which is the hardest work in business. That’s how you really make a contribution and add to the legacy of those who went before. You build a company that will still stand for something a generation or two from now. That’s what Walt Disney did, and Hewlett and Packard, and the people who built Intel. They created a company to last, not just to make money. That’s what I want Apple to be.” A lot of founders might be that way, but nothing could be more true of the majority of venture capitalists.” (The Seven Deadly Sins of Venture Capital)

“Credibility alongside conviction can dramatically overpower likability. The spirit of contrarianism is, most often, framed in terms of the pursuit of something great. In the face of most great accomplishments, there are more important things than being liked.” (Conviction-Led Contrarianism)

So in a world of consensus capital conglomerates, how are you supposed to demonstrate conviction? Simple. You have to avoid playing the game on the field. Unfortunately, if you’re at a firm that is culturally setup to play the game on the field then you’re probably SOL. Either learn to play their game, or get off of their field. But if the pursuit of conviction, even more than scale, is compelling to your soul, then there is an answer. (Conviction Capitalists)

From YC to bulge-bracket venture firms, the pursuit of scale has made slaves to incentives out of a broad swath of participants in tech. The fear of failure has further exacerbated that slavery. We allow our incentives to shape us because of fear. Fear of being poor, being stupid, or of simply being left behind. Fear of Missing Out. That fear leads us down the path of normativity. We assimilate. We seek alikedness. We shave off the rough edges of our individuality until we are smoothed to the grooves of the path of least resistance. But the path of least resistance has no place for contrarian conviction. In fact, it has no place for beliefs of any kind, for fear that your beliefs will take you down paths that the consensus prefers not to go. (Build What’s Fundable)

Noisier Than Ever

One of the obstacles in Finding in modern venture is that it’s SO noisy. No longer is it likely that you would be a founder, just minding your own business, and some scrappy investor tracked you down to your Mom’s garage. If you start something, EVERYONE knows about it. It’s louder than ever. (The Four Pillars of Venture Investing)

“It reminds me an idea about efficient market theory. Increasingly, the public market is becoming more irrational (see: Meme Stocks). Some people think you’re trying to determine what a particular stock price will do. But that’s not quite right. You’re actually trying to determine what you think other people think a stock price will do. The impact of human psychology on the particular investment is a quantifiable delta that can’t be ignored. The same is the most true it could be in venture capital.” (The Four Pillars of Venture Investing)

“Venture capital has become divorced from the long-term outcome of the business and focused on the incidental outcome — entry to exit.” (The Loudest Models)

“Just because the voice is the loudest doesn’t make it the smartest or the most thoughtful or the best or the right one from your strategy.” (When History Rhymes)

“Most firms have fallen into the trap of thinking anything can be a fit if it’s hot.” (When History Rhymes)

“What makes starting something feel hard is not the ability to start, but the weight of the expectations. But you have to stop and ask yourself... why do you have those expectations? And if its because the loudest models with the most capital have been shouting “this is the way” since before you got to high school, then you need to step back and recognize that you’ve been programmed. That expectation of “I need to raise a lot of money to grow super fast to raise a ton more to get really big to hire a ton of people to be a platform to own a huge swath of a massive market...” It’s programmed. It is not reality.” (Building Mighty Small Businesses)

For most people the volume of interactions in the vibe-o-sphere is the biggest argument against participating. I was the same way. Before I started this blog, I was convinced that I would just be shouting into the void. I wasn’t consuming all the content that was being created, why should I add to the noise? But the first thing you realize about creating anything once you start doing it consistently, be it writing, art, poetry, music, videos, or music, is that what it does to you is much more important than what it does to anyone else. Paraphrasing a point that Dwarkesh Patel made about the benefit of doing his podcast: “The real flywheel of the podcast is not compounding audience growth. The real flywheel of any creative endeavor is compounding the creator.“ (The State of Startup Media)

“The overwhelming volume of ideas could also be a symptom of “personal truth,” where everyone thinks their ideas are true vs. the meritocratic Core Truth. But I prefer to believe that, in the end, the quality of ideas will win out. Despite the way we consume our media and the fact that we have become so programmable, ultimately the best ideas can win out. Things like Communism were a bad ideas and, despite a LOT of support, even in the US, it eventually died out (sort of). The holocaust might have had a pretty solid PR team and propaganda machine but the light of history eventually put that idea in its place (sort of). From slavery to horse-drawn carriages, eventually almost every idea gives way to better ideas. That may not always be true, but its the optimistic view of the world I prefer to espouse.” (The State of Startup Media)

“Now, unfortunately, I have no solutions. The currency of the Attention Economy will continue to be loudness, regardless of the quality of the underlying ideas. We can’t stop that. It’s out of our control. What we can control is the personal commitment we have to what is true. But for those of us who are playing a wildly interconnected game where we’re dependent on forces who have not made the same commitment, and are susceptible to the loudest models? We will find ourselves forced to “play the game on the field” as they say. Whether we like it or not. Truth be damned. (The Volume of Your Inaccuracy)

Propaganda can be used for good or for evil. But a fundamental element of the human experience should be the ability to choose the stories we believe in (I’ll come back to that). If we’re not actively choosing the stories we want to believe in then we’re allowing ourselves to be programmed with someone else’s worldview. And, whether we like it or not, it is getting easier and easier to program people. But the craziest thing about that is that we’ve had decades of warnings and yet done nothing. (The CogSec Chronicles)

The lead-in thus far has been the idea that propaganda has existed since the dawn of humankind. What has changed is the environment in which we are exposed to programmability. The tools are more effective than ever. But the conclusion is not to blame the tools, whether it be deepfakes or AI, nor to blame the masses or the leaders of said herds, be they demagogic con men or brow beating shrill guilt-inducers. Conservatives or liberals. Nor to blame the complexity of a situation for turning you against it. No, your psychosis is yours alone. If you have clinical mental health issues, then see a professional. But for the majority of us that deal simply with the psychosis that is humanity, the accountability stays with you. You are fully capable of choosing to kick against the pricks of your would-be programmers and own your own belief system. But it requires concerted effort. More so today than maybe any other point in human history. (The CogSec Chronicles)

That being said, I am (unfortunately) starting to see a lot less even-minded approaches from VCs when it comes to fiduciary board responsibilities. Many venture firms are, increasingly, negotiating in bad faith and allowing themselves to be driven by nothing other than their own agenda. But not everyone used to have an agenda. Today, venture is SO loud that it requires everyone to pay attention to everything all the time. “We can’t help it!” So, in this brief reflection, my takeaway is that being a good board member requires that near-schizophrenic capability to wear multiple mental hats. Using that compartmentalization is meant to limit how much emotion and personal bias people bring to these transactions. Again, that’s hard for VCs that are drowning in noise in pursuit of signal. But it’s necessary. (Wearing Fiduciary Hats)

And as time went on, I actually felt like that middle ground was one of the most important characteristics about me. I take pride in it. In every sense of the word, I was a centrist. I saw merit on both sides of most arguments and was able to navigate to what I felt like was the right middle ground on most issues. I’ve written before about my approach to that middle. (The Ethos of Nuance)

Building Things Worth Building

“Businesses shouldn’t be ashamed of the ways they make money (unless they’re… you know… illegal or immoral.) Businesses also shouldn’t lie about how they make money. Pretending like you don’t care about advertisers if, in fact, advertisers are the only way your business can survive is disingenuous.” (The Inevitability of Advertising)

“My fear, as I’ve talked about over and over again, is the danger of venture capital’s formula coming from the loudest voices. People with multi-billion dollar funds are shouting from the rooftops: “massive ambition + massive capital = massive outcome.” And for a small percentage of businesses, that can be true. But for the vast majority of entrepreneurs, startups, (and even smaller investors) that does not work. And the danger is that those voices are SO LOUD that they drag a generation of business builders into their very eccentric model, and in the process destroy a generation of businesses that COULD have mattered, but now will never be more than write-offs and disappointments.” (Building Mighty Small Businesses)

“In its wake, this model of listening the loudest models and chasing a very specific strategy has led to a lost generation of potentially great companies. The capital model we have now has been in pursuit of massive generationally ambitious companies. But they’ve been built by sacrificing a generation of startups on the altar of burn rates and high growth. What could those companies have been if they’d been built differently?” (The Seven Deadly Sins of Venture Capital)

“If I were to describe a common thread through all of these nuggets, it’s this: we should all be more aware that our beliefs are fully on display. Whether its the company you choose to criticize, the movies you decide to make, or the stories you decide to tell or believe. They are reflections of your values — of who you are.” (Beliefs, Blockbusters, and Boyhood)

At the same time, conviction is not enough. You can have conviction in something that is deeply untrue. And if you do, eventually you will fall victim to the qualifier of contrarianism. You also have to be right. But when conviction is, as Naval says, “[reasoned] independently from the ground up and [resistant to] pressure to conform,” that is a true contrarianism. Combine that with conviction born out of first-principles and truth-seeking? That is true conviction-led contrarianism. That is the path to real, world-shattering deviance. (Conviction-Led Contrarianism)

I’ve written before about a great monologue from the movie Secondhand Lions. In it, one of the main characters talks about belief: “Doesn’t matter if they’re true. If you want to believe in something then believe in it. Just because something isn’t true that’s no reason you can’t believe in it. Sometimes, the things that may or may not be true are the things that a man needs to believe in the most. That people are basically good. That honor, courage, and virtue mean everything. That power and money, money and power, mean nothing. That good always triumphs over evil. Doesn’t matter if it’s true or not, you see. A man should believe in those things because those are things worth believing in.“ (The CogSec Chronicles)

In a world of consensus-driven scale-focused investors who are solving for incremental outcomes, or attention-centered founders who are most interested in building a brand and getting a bag, be someone who is willing to build an empire. A generational business that will last lifetimes. Because not enough people do that anymore, and that’s conviction. And that conviction comes from having spent obsessive amounts of time thinking about how to solve a particular problem. (Conviction Capitalists)

We need a new commitment to “creative imagination with technical know-how.” A new commitment to Imagineering. A culture of people committed to planning for the future in a way that, rather than trying to force their worldview onto the world, they instead seek to understand the world as it actually is, and then shape the solutions that will work in that reality based on the data available to us. Will that solve every problem and injustice? Absolutely not. But that is the definition of American progress. Solving problems with technological fixes, and then finding technological fixes for the new problems we’ve created. Walt Disney provided a prototype for us that, I believe, could usher in the fundamentally transformative future many of us dream about all the time. If only we are willing to imagineer that future. (In Defense of Disney)

I always strain to emphasize that there isn’t necessarily a good or bad way to build a company (sans fraud or other crimes). To each their own. But my concern with this particular hammer / nail mismatch is that it poisons the well for a generation of companies that are NOT going to be worth $10 or $50 billion. The “middle-class” outcomes. And you can say “aim for the moon, you hit the stars,” or whatever. But the way you build a company dictates the outcomes that are available to you. (Momentum != Moat)

A deeper manifestation of a believer missionary is an ideological purist. People who are committed whole-heartedly to what they’re doing, not because it makes sense but because its the only thing that makes sense. Their companies are more than representations of a business model. They’re a representation of world views. (Founder Ideology)

YC is a culprit in that pursuit of a scalable model in an unscalable asset class. a16z is the same. These engines that thrive off of more capital, more companies, more hype, more attention are exacerbating the problem. And in pursuit of the unscalable, they’re trying to build in scalability where it doesn’t belong. The largest, most important outcomes in business building can’t be curated. But in the pursuit of trying to make the company-building formula scalable, the rough edges of important ideas get sanded off. (Build What’s Fundable)

The same is true in tech. This normative mentality of building around consensus-driven ideas is trickling down into millions of lives that will be negatively impacted, both because they will build worse things, but also because they will fail to develop independent thought. That’s not to say that contrarian companies aren’t being built. On the contrary, those are the companies that do work most often. But the long-tail of people are building, while being informed by the zeitgeist of consensus, not the truth-seeking of independence. (Build What’s Fundable)

When you look at successful contrarian examples, many of them have been built by existing billionaires (Tesla, SpaceX, Palantir, Anduril). The lesson from that, I think, isn’t “be a billionaire first then you can have independent thoughts.” It is, instead, to reflect on what other characteristics often lead to those outcomes. And, in my opinion, the other commonality that a lot of those companies have is that they’re led by ideological purists. People that believe in a mission. (Build What’s Fundable)

The key takeaway here is that the only antidote to an increasingly normative culture built around consensus-formation is to inspire the participants of that culture to pursue ideological purity: to believe in something! (Build What’s Fundable)

Technology is not a force for good. Technology, like any amorphous collection of concepts and inanimate objects, is a tool. The people who wield technology dictate whether it yields good or bad outcomes. Incentives are the forces that move people towards particular paths, be they bad or good. But beliefs, if firmly held, can supersede incentives in the pursuit of something more important. My incentives may encourage me to lie, cheat, and steal, because each can enrich me economically. But my beliefs stop me from being a slave to my incentives. They inspire me to live on a higher plane. (Build What’s Fundable)

But there is a better way. In a world of normativity-seeking systems, anchor yourself in beliefs. Find things worth believing in. Even when they’re hard. Even when they’re unpopular. Find beliefs worth dying for. Or better yet, find beliefs worth living for. (Build What’s Fundable)

The Job of a Venture Capitalist

“Just like any act of allocation; you’re allocating a finite resource. And your time is a finite resource. So, as a venture investor, you have a finite amount of time and attention that you have to allocate to finding, picking, winning, or supporting. And you can say “I’m just going to be a good Finder,” but if that’s your approach you better (1) be at a firm with good pickers, winners, and supporters, and (2) be at a firm that is willing to let you just be a good Finder.” (The Four Pillars of Venture Investing)

“Despite the feelings of yearning in the American soul for business ownership, its been trending down. Covid represented enough of an economic upset that we saw a surge in new businesses getting started. That is good news. But the bad news is that this new generation of entrepreneurs is teetering on the edge of being co-opted by a very loud minority of single-minded “hustle hacker” VCs solving for a very specific economic outcome.“ (Building Mighty Small Businesses)

“Now, when you’re a VC with a portfolio. That’s fine. It used to be 3 in 10 would matter, now 1 in 10 matter. That’s fine as long as I find a “one” to matter. But for a huge swath of founders and startup employees, that means that 90%+ of you are getting left on the scrap heap of history with the tattered remains of a business that could have been something special, but instead it was over-burned into a rounding error on somebody’s billion dollar fund math.“ (Building Mighty Small Businesses)

This is, in simplest terms, a lack of product market fit. Venture capital has orchestrated a specific product: “massive ambition + massive capital = massive outcome.” And what this data is indicating is that that product wasn’t a fit for the vast majority of startups who took part in it.” (Building Mighty Small Businesses)

The best founders I have ever interacted with articulate themselves with precision, logical coherence and flow from one idea to another, a focus on the most relevant information without getting distracted by the logical course at hand, and an “earned insight” into the complex issue they’re tackling that gets right to the center of the opportunity. The biggest obstacle in achieving “clarity of thought” when you’re in the earliest days of building a business is the fact that it can be difficult to see clearly something that is non-existant. But that is the exceptional capability of world-class founders. They can see clearly that which does not yet exist. And then they spend exorbitant, God-like amounts of effort and grit willing that thing into existence. When you talk to someone like that about their business, they can see, with immense clarity, what it could become. (Clarity of Thought)

The “let me know how I can be helpful” meme is a deep and rich pool of constructive criticism. Where is the sincerity? Where is the follow through? Why are VCs so criticized? Because the meme sheds light on a truth that most VCs are more interested in the potential of the investment than the potential of the person. (VCs Beyond The Meme)

Ever since I first started writing, I’ve revolved around this idea that “everyone is an allocator of something.” As I’ve kept exploring the idea of allocation, I come back to this definition of investing: “The art and science of allocating finite resources to create an optimal outcome.” Last time I unpacked that quote in relation to everyone being an investor, I made this point: “The reason that line is so broad is because I believe it applies to almost everyone and everything. Everyone is an investor of something because they’re allocating finite things in their lives: money, attention, time, effort, love.” Allocation is an art. It’s a beautiful and impressive thing. Though, unfortunately, it is increasingly less applicable a term to what venture capitalists do. (The Holding Companies of Our Hearts)

Study the actual allocators. Not the low-risk, well-diversified, minority equity gamblers like the VCs. Study the allocators building engines to identify the highest quality assets and then bring them into a complex, but potentially high-value AI-driven ecosystem. Those are the allocators who are the real heroes. Those are the allocators who are the real artists. Not VCs. (The Holding Companies of Our Hearts)

However, one of the things that can muddy the waters is how often different parts of a VCs capabilities are at odds with each other. The vast majority of a VC’s time is dedicated to finding, picking, and winning deals, to the point that they often shape their whole world view around the thrill of the chase. And in many cases, that serves them well. Always on to the next deal, with an unquenchable thirst for victory. But there is one particular part of the job that requires a fundamental paradigm shift in how a VC’s brain works: being a board member. (Wearing Fiduciary Hats)

My response was that, while this is a funny joke, its a misunderstanding of the meaning of words. “Underwriting” is just a boring word for a familiar phrase: “what do you have to believe?” I tried to start a conversation with Anjney, but didn’t get a response yet. My question was what was the most common reason he passed on investments. If you say, “quality of founder” then what that means is “I don’t believe this founder is good enough.” In other words? “I can’t underwrite this founder’s ability to succeed.” Everyone “underwrites” variables across every aspect of their life that requires any decision making. I decide not to marry the person I’m dating? I can’t underwrite their ability to be a good partner. I choose not to buy a particular stock? I can’t underwrite that stock’s future value. I opt out of seeing a particular movie? I can’t underwrite that movie’s ability to entertain me. Every decision is made on data and then measured by outcomes. Some times we’re right, sometimes we’re wrong. In everything, we just hope that the quantum of “wrong” doesn’t knock us out of the game. If we underwrite our ability to drive very fast on a wet, slippery road high in the mountains as being “very capable,” we may never get to underwrite anything again if we’re wrong. (Why Bother?)

As an investor investing into that “momentum,” you’re paying up by putting a multiple on revenue that is very unlikely to materialize in the long-term. The burnout we’re likely to see among a number of investors who try and play this game will be because, as Yoni Rechtman at Slow Ventures puts it, “this is a marathon AND a sprint.” Momentum investors are, too often, only focused on the sprint. (Momentum != Moat)

Venture capital, as a career, has these same characteristics of normativity. One of my favorite investors, Ho Nam, was asked what he saw as a meaningful flaw in venture capital as an industry, and he pointed to “career pathing”: “It’s become a profession where you climb the ladder and paint by numbers, which is a good way to mass produce paintings.“ (Build What’s Fundable)

Finding Yourself

“I don’t mean to be combative, counterpositioned, or difficult to talk to just because. Barking in public is being willing to cast off what society expects of you in favor of what YOU expect of you. What do YOU think you should do? I also don’t mean being selfish and just doing whatever you feel like. Barking in public is trusting yourself. Your underlying perspective, code, preferences, values — those should guide how you bark. It means doing things, not because something outside yourself tells you to, but because something greater than yourself tells you to.“ (Barking In Public)

“Each of us has some version of the things we learn that guide our actions. I’ve written before about the moral obligation of wisdom acquisition. In it, I referenced a talk by Charlie Munger: “The acquisition of wisdom is a moral duty. It’s not something you do just to advance in life. And there’s a corollary to that idea that is very important. It requires that you’re hooked on lifetime learning. Without lifetime learning, you people are not going to do very well. You are not going to get very far in life based on what you already know. You’re going to advance in life by what you learn after you leave here.“ (Don’t Die With Your Music Still In You)

In the book The Courage To Be Disliked there is a critical framing about life: every problem is an interpersonal problem. That no matter what internal worry we have, it is always connected to our relationships with other people. “The shadows of other people are always present.” Instead of spending your life constantly worried about that shadow, you have to have the courage to disregard it: “Your unhappiness cannot be blamed on your past or your environment. And it isn’t that you lack competence. You just lack courage. One might say you are lacking in the courage to be happy.” (Conviction-Led Contrarianism)

When we evaluate our lives through the lens of how other people react, we will always be our harshest critic because we have no idea how they will react, so we’re solving for all the possible negative reactions. Rather, we should be acknowledging that sometimes people respond to your “deviance” negatively, not because you’re messed up but because they’re messed up. The reality is that, as Lao Tzu said — “care about what other people think and you will always be their prisoner.” (Conviction-Led Contrarianism)

So. Why did I start a blog post on an investing blog with the prodigal son? Because the prodigal son is the story I think of most when I reflect on regret. Regret is a poison. The sunk cost fallacy of the soul. Regret will, more often than not, lead us to making worse decisions rather than better decisions. (Regret Maximization Sickness)

In any decision we’ve made, we can feel overcome by regret. We realize we are not who we wish we were and we give up. Or we feel like the decisions we make can only make things worse, so why not just maintain the status quo and avoid for meaningful disruptions. So many of the people around me (myself included) seem like we’re going through life enduring a regret maximization framework. Every experience we have, its as if we’re looking to identify any and all regret we can squeeze out of that experience. Pouring salt in the wound, just for good measure. (Regret Maximization Sickness)

“We believe that if we just do a LOT of things quickly enough then in the long-run the bad things won’t matter. But, while I’m not here to pass judgement, I am here to reiterate this point: “You, as a person, are the sum total of all the things you do, think, hear, write, and say.” Life is cumulative. Every choice you make has an impact on your soul. So choose wisely. (A Fungible Worldview)

As I take a moment to reflect this morning I think the takeaway is that no professional accomplishment can fulfill you. They can be rewarding, they can support you financially, there is nothing wrong with them. But as I’ve been reading about in The Courage To Be Disliked, most, if not all, of the problems we deal with in life are interpersonal problems. When we struggle it is often because we are living our lives inauthentically based on what we think others would want us to do or expect us to do. And so we feel stuck. But days like today are for me to reflect on that reality. What does it mean to live authentically? (Seek Sunlight)

It doesn’t take a visionary to be happy for themselves. You got yourself a snack? Sure; anyone can feel that satisfaction. You’ve built yourself a pretty exceptional quality of life for a few decades? We all strive for that. No, the true visionary, the person who sees most clearly what it means to be truly happy; to truly hope for a better world, is the person willing to live, fight, and even die for a world that they will never get to see. (Have Kids. Or Don’t. But Have Kids.)

Your value system may enable you to be great, while ensuring that family or faith comes first. Your value system may empower you to live for yourself, rather than for the performative satisfaction of others. But ultimately, there is the possibility that your value system will not lead to “greatness” in the eyes of the rest of the world. Are you okay with that? (What Is An Extraordinary Man?)

In the pursuit of answering the question: “What is an extraordinary man?” I’m met with the conclusion that to be extraordinary is to seek out the glory of God. The glory of God is the benefit of other people. If you are consumed by a company “mission” for the sake of having a mission, then you have missed the mark. If you feel entitled to the life force of those around you because you put up your hand and started a company, you are not a good steward of the life force of others. But if you seek to do good. If you seek to make the world better. If you seek to lift up the broken hearted. If you seek to shape the world around you so that others who sit upon that world may sit a little higher, then you have found vision. The mission that you pursue will be worthy of your time and eternal potential. And don’t let anyone tell you that their value system is the only appropriate bar for measuring that mission. Whether it is raising a family, lifting up the sorrowful, demonstrating kindness, or transforming the way the world works with technology. It’s all a function of who you really are and what you really want. (What Is An Extraordinary Man?)

Reflecting on all of this, I’m reminded of a common idea: “You choose every day who you are.” As a founder, an investor, a builder, a husband or father or mother or wife. As a person. The ideological motivations that you have are not defaults. They are choices. Each of these founders (and any other person for that matter) can demonstrate a variety of characteristics that would probably fit into each of these six buckets. It’s not about applying a firm label to any one person. The point of the mental model is to be instructive. Both for investors to evaluate founders, but more importantly for founders to evaluate themselves. (Founder Ideology)

So the question isn’t “how do I win?” Because you can win (and lose) lots of different ways. The question is “who do I want to be IF I win?” Ideology, like beliefs, should be a leading indicator of action. Who you want to be should dictate the type of ideological bent you have as you go throughout your life. (Founder Ideology)

The famous Theodore Roosevelt quote about the “man in the arena” draws a distinction between the critic; the man who points out how the strong man fumbles, and the “doer of deeds.” But the reality is that, in our own life, we play the full cast of characters. Just as we are the man in our own arena, we are also the critic. It is true that the critic doesn’t count. When our “face is marred by dust and sweat and blood,” that is what counts. Roosevelt talks of “those cold and timid souls who neither know victory nor defeat.” But the unfortunate reality is that the only person who knows both our victories and our defeats in their entirety is us. And when we give air to the critic inside of us, we elevate their status. We make them count. When we complain, we muscle out all room to build. To strive and achieve. We take for granted the striving, the effort, the fight we exert because we’re too swallowed up in the intoxication of disappointment porn. (Complaining Is The Mind Killer)

Nuance, Nuance, Nuance

“So often, we default to “well, my in-group thinks Donald Trump is a fascist or the second coming of Jesus Christ, so I should too.” Or “well, Tesla is the carrier of the apocalypse, or humanity’s only future for stock gains, so I’ll go with that.” It’s the path of least resistance. Instead, we should be more willing to embrace nuance. Unpack our beliefs. And say “even though my in-group is bothered by the actions of the CEO of Tesla, electrifying vehicles is a core belief for me as I understand climate change. Therefore, my values will overwhelm my in-group precedents.” (Beliefs, Blockbusters, Boyhood)

The desire to believe things or not believe things based on emotional responses or default in-group beliefs is dangerous. It is how people make the wrong decisions in what they build, fund, believe, or fight for. The lack of critical thinking leads to the death of nuance. I’ve written about nuance before, pointing out that “any staunch beliefs, one way or another, have messy middles filled with nuance that are probably closer to reality.” But heuristics that reinforce in-group adherence and deprioritize critical thinking will fail to appreciate that nuance. (The Burden of Proof)

So... reflecting on my tweet. Was it a shitty thing to say? I don’t think so. Though, like everything about the internet, Twitter is probably the hardest place to articulate nuance. So for anyone my tweet and the doubling-down of this piece has offended, I do apologize. I don’t mean to give offense. And I don’t mean to impugn anyone’s worth or life choices based on my own preferred framework. But I stand by some core beliefs. First, being an investor and builder, at least when it comes to cutting edge technology companies, is an inherently optimistic and hope-filled endeavor. Second, having children is the most hope-filled demonstration you can offer in favor of the future you hope to bring about. Third, I believe that having children is one of the most fundamentally fulfilling experiences you can have in life. If you have the means and opportunity to do so, I would encourage you to find ways to shape the lives of the rising generation. Whether that’s through your own genetic offspring, those you can adopt or foster, or those in your sphere of influence. Because nothing is more satisfying than planting those seeds, the shade of which you will never sit in, but the potential of which you can bask in every day. (Have Kids. Or Don’t. But Have Kids.)

What I want is NOT to be more partisan. I stand by what I wrote before: “So often, people trust nuanced tribal group identity and political association without any basis of first principles. I’m not Mormon, or Christian, or Republican, or a Costco member. I am a system of values and beliefs that determine how I act. Group membership should be a lagging indicator of your beliefs, not a leading indicator. When people substitute their own value system with a cookie-cutter platform from their in-group the first thing to die is nuance. I don’t want to be more Republican and, therefore, hold more Republican views anymore than I want to be more Democrat and hold more Democratic views. I’m not looking for world-views. I’m looking for beliefs. What do I believe? What is the right argument? What is the right stance to take? Because in seeking out truth, my hope is that we find healing. The path to progress is paved in the pursuit of truth. I want progress. I want truth.“ (The Ethos of Nuance)

The story is not the glory; its the complicated, messy narrative of all the details we can wrangle together. And being willing to embrace the mess is where exceptional storytelling really lies. “The novelist Richard Powers said the best arguments in the world, and that’s all we do is argue, won’t change a single person’s point of view. The only thing that can do that is a good story. Why? Because a good story is not taking sides. It’s understanding that Achilles has his heel and his hubris to go along with his great strength.” (Tell Better Stories)

As we recover from a Turkey-fueled carbo-load, we can so easily relish the time off from work, codified by football and family time, without sitting back to appreciate the narrative we’ve inherited. Giving thanks for something; but for what? Thanksgiving is a uniquely American holiday, but like many holidays, its narrative has been dulled around the edges. The pilgrims. The first Thanksgiving. Similar to Christmas or Easter, it can be softened by candy and tradition without looking to the deeply enriched narrative at the center. America is the same. In many ways, the narrative of America has been dulled as “bloodless, galant myth.” That softening of the true story behind the myth has left the door open to surprise and disappointment. Here we thought the founding fathers were God-like perfection incarnate; come to find out they owned slaves? And often thought lame things?” Ken Burns says that “we have been burdened by our lack of knowledge of the past, not by any kind of knowledge of it.” Harry Truman said it another way when he supposedly said “the only thing that’s really new is the history you don’t know.” (Tell Better Stories)

I find myself writing this exact line over, and over, and over again. Is there a definitive truth? Or is there simply preferable lies? While there are plenty of different view points, I have to believe in truth; no matter the source. Rather than give way to cynical acceptance of the noble lies around us, I instead choose to embrace nuance; something else I have written about over, and over, and over, and over again. Whether it comes to religion, economics, company building, relationships, or any other aspect of my life. I have to believe that there is truth. Nuanced truth, yes. But truth, nonetheless. In many cases, one of the biggest obstacles is that the nuance is so haze-inducing that it renders the shape of truth completely immaterial. Something feels so complex and nuanced that it loses all definition. (You Sit on a Throne of Lies)

Hyperlegibility

Packy explains hyperlegibility this way: “Information that was once hard to find is now hard to avoid... Hyperlegibility emerges with game theoretical certainty from each of our desire to win whatever game it is you’re playing. In order for the right people and projects to find you, you must make yourself legible to them. To stand out in a sea of people making themselves legible, you must make yourself Hyperlegible: so easy to read and understand you rise to the top.” (The State of Startup Media)

But often, more general truths wield power because people believe in them. A few weeks ago I wrote about this great quote from Game of Thrones: “Power is a curious thing. Three great men sit in a room: a king, a priest, and a rich man. Between them stands a common [mercenary]. Each great man bids the [mercenary] kill the other two. Who lives? Who dies? [The mercenary] has neither crown nor gold nor favor with the gods. He has a sword; the power of life and death. But if it’s swordsmen who rule, why do we pretend kings hold all the power? Power resides where men believe it resides.“ (Conviction-Led Contrarianism)

The very best founders build a conceptual framework right in front of you so that you can easily hang different ideas, questions, and information from that framework. Charlie Munger describes a “Latticework of Mental Models” that he uses to keep track of details of a particular idea: “The first rule is that you can’t really know anything if you just remember isolated facts and try and bang ’em back. If the facts don’t hang together on a latticework of theory, you don’t have them in a usable form. You’ve got to have models in your head. And you’ve got to array your experience, both vicarious and direct, on this latticework of models. You may have noticed students who just try to remember and pound back what is remembered. Well, they fail in school and in life. You’ve got to hang experience on a latticework of models in your head.” (Clarity of Thought)

The truly exceptional are able to gauge the level of context a particular listener has and adjust accordingly. If you’re a complete noob to a space, the presenter is free to offer you a fully-formed network that is born out of their own assumptions, hypotheses, and explorations. But when you interact with someone who has anywhere from a passable to an expert level of understanding, the presenter is also able to take their framework and help anchor it to key concepts that the amateur or expert already has in their own head. (Clarity of Thought)

In many cases, we know the lineage of our ideas; the historicity of our thinking. I may know the book / essay / tweet / song / movie that a particular aspect of my worldview was inspired by. But in the vast majority of cases we do not. We do not know where our programming has forked from. (I Wish I Knew How To Quit Roam Research)

Packy McCormick’s introduced a word into my lexicon that I now use constantly because it is so effectively descriptive of the world around us: hyperlegible. It’s this idea that, because of the access to information via content and cultural nuance via social media, so much of the world around us has become dramatically legible; almost annoyingly so. Think about all these micro cultures that you would have never found in an encyclopedia, but now there are entire TV seasons dedicated to. In a world where the tech industry is so hyperlegible, YC’s original mission of making that industry less opaque is forced to evolve. Where startups used to be the tool of choice for rebels to break barriers, they’ve increasingly become a consensus norming funnel. (Build What’s Fundable)

Starting a startup, doing YC, raising venture, building a “unicorn.” It’s become the new-age version of go to a good school, get a good job, buy a house in the suburbs. It’s normative culture; the tried a true path. Social media and short-form video only exacerbate the programmable normativity because we see these hyperlegible paths. The most dangerous thing about hyperlegible life paths is that they diminish the need for critical thinking across the population. The thinking has been done for you, or so the logic goes. (Build What’s Fundable)

So I’ll leave you with this. Tread carefully. Reflect properly on the stories you buy into, and the stories you tell. The stories you perpetuate. Reflect critically on the implications of the stories you tell and the degree to which you believe them. I believe orange juice makes me feel better when I’m sick. But I wouldn’t try to cure cancer with it. (You Sit on a Throne of Lies)

Interdependencies

“This is a critical point about the pursuit of contrarian thinking that very few people take the time to appreciate. Despite your most earnest desires, there are instances where your beliefs carry with them dependencies that can dictate whether your ideas are right or wrong. Regardless of the intellectual merits of your beliefs, life is an intricate web of interdependencies that can exert untold control over what we choose to believe. Understanding those dependencies is the only way that you can then discover approaches to thinking independently.“ (Conviction-Led Contrarianism)

“There is a great line from John Maynard Keynes where he says “markets can remain irrational longer than you can remain solvent.” That is a quintessential dependency. If you wanted to invest in a stock because it seemed to have rational upside, the dependency is on a market that is capable of remaining irrational for quite a long time. Potentially, longer than your capital duration. And if thats the case then regardless of the intellectual quality of your perspective, the dependency on an irrational market dictates whether you can be right or wrong.“ (Conviction-Led Contrarianism)

But at its core, the American Experiment was built on a foundation of Enlightenment ideals. Liberty, individual rights, consent of the governed. The initial application of these rights may have been imperfect by a long shot. But that was the starting point. Something markedly different than everything that had come before. Most importantly, in my mind, the Constitution established a framework for self-correction through protest, reform and amendments. And it worked over and over again. Through abolition, civil rights, and suffrage. Name another nation that has managed to balance global power where it COULD do whatever it wanted, but it DIDN’T. Instead, the legacy of the United States has remained one of self-criticism. (An American Optimism)

The principle instilled in me from that formative experience was that life’s balance comes from a combination of working hard enough to be smart, while pausing long enough to ponder. Working too hard led to burnout but never finding time to pause left you imbalanced. (Do Nothing and Do Everything)

Since then, I’ve had plenty of experiences in my life that had worst case scenarios. Things to prepare for, things that don’t always go my way. What I learned from that principle that my mom taught me was that there is value in preparing for the worst and then expecting the best. But the other side of that coin that can be the mind killer is the inclination to languish in the worst of it. To sorrow in lamentations. To complain. (Complaining Is The Mind Killer)

Everything from founding myths to unifying narratives rests on this idea of justification in elaboration. The mythology of the American Founders serves a particular unifying purpose and for that reason, its been allowed to persist; even defended vigorously. There’s a lot that’s been said about memetics and the way ideas percolate. Propaganda during WWII and the Cold War served what most see as both good and evil causes; supporting the American War Effort and propping up both the Socialist and the Communist machines. So much of history is defined by a story’s “right” to be told. But cynicism has been the response of a world warped by manipulation. To me, people’s psyche’s have so often fractured in one of two directions: (1) it’s all a lie, so I don’t believe anything or in anything, or (2) it’s all a lie, so I’ll choose which lie I want to believe. That cannot be the ideal end state. (You Sit On a Throne of Lies)

Future Posts

Succession planning is a whole other interesting topic about venture funds that would be worth unpacking in another post. (Venture Capital Unbundled)

I have a different rant that maybe I’ll write about here someday. But the TLDR is that the majority of Marvel movies have revolved around heroes almost exclusively focused on self-reflection. People look inside themselves and find greatness. But very rarely are the heroes in the Marvel movies seeking redemption. Thunderbolts is a good movie. But in particular I think it’s an important movie for Marvel because it exposes a narrative that is allowed to focus on characters who are seeking redemption without being defined by that journey. (Regret Maximization Sickness)

I’m not a big golf guy, but I immediately became a huge Scottie Scheffler fan. In it, he reflected on how, despite being the number one golfer in the world, it doesn’t fulfill him. It is one of the greatest monologues I’ve seen in a long time. And you had better believe I will be reflecting on it again in a much longer essay. Some of my favorite parts: “I’m not here to inspire somebody else to be the best player in the world, because what’s the point, you know? This is not a fulfilling life. It’s... it’s fulfilling from the sense of accomplishment, but it’s not fulfilling from a sense of, like, the deepest, you know, places of your heart. You know, there’s a lot of people that make it to what they thought was going to fulfill them in life, and then you get there and all of a sudden you get to number one in the world, and they’re like, “What’s the point?” And, you know...I... I really do believe that, because, you know, what is the point? You’re like, “What? Why do I want to win this tournament so bad?” That’s something that I wrestle with on a daily basis. Because if I win, it’s going to be awesome for about 2 minutes, and then we’re going to get to the next week, and it’s going to be like, “Hey, you won two majors this year. How important is it for you to win the FedEx Cup Playoffs?” And it’s just like... we’re... we’re back here again, you know?I love being able to play this game for a living. It’s... it’s one of the greatest joys of my life. But does it fill the deepest, you know, wants and desires of my heart? Absolutely not. You know, that’s why I talk about family being my priority—because it really is. You know, I’m blessed to be able to come out here and play golf. But if my golf ever started affecting my home life, or it ever affected the relationship I have with my wife or with my son, you know, that’s going to be the last day that I play out here for a living.“ (Seek Sunlight)

One paper by Lucas Freund called The Age of the Algorithmic Society unpacks a lot of these ideas around recursive feedback loops, filter bubbles, and echo chambers that can restrict exposure to diverse ideas; almost a form of digital myth-making. Ideas that are built on regurgitations of ideas that were formatted from training data representing combinations of other ideas becomes problematic. This is a broader, fascinating conversation about poststructuralism and how language and discourse may not reflect reality, but rather they construct it. Poststructuralism is the philosophy that explains how truth becomes unstable because it becomes disconnected from facts in favor of vibes. But cogsec is the defense against what happens when that instability is exploited. (The CogSec Chronicles)

Again. I could write a book about the dreamed, yet unfulfilled promises of EPCOT (and many people have). But I’ll leave that for another time. (In Defense of Disney)

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