Sundays with Sam #24: Comparison Despair

The SpaceX IPO, the AI gold rush, and the strange despair of watching someone else win.

Moonshots

Last week, the SpaceX IPO created 4,400 new millionaires. It was supposed to be 4,000 but the 30% pop in the stock ended up taking another 400 or so lucky folks over the line. Another 400 current and former employees may end up with stock worth more than $100 million.

These are absurd numbers. They read less like business news than mythology: a company goes public and, overnight, thousands of engineers, operators, and early employees cross the invisible line between working life and financial freedom.

Good for them. I mean that sincerely. I also understand why news like this makes people feel insane.

There is a particular kind of despair that arrives when the roulette wheel stops and you were sitting on the wrong number. You were working hard. You were doing respectable things. Then one day, people around you become wealthy on a scale that makes your entire plan feel completely inadequate.

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Ordinary Success Has Lost Its Meaning

Deedy Das recently described the vibes in San Francisco as frenetic. He wrote about the divide in outcomes created by AI: the small cohort of people at Anthropic, OpenAI, Nvidia, and the newest AI companies who have crossed into retirement wealth, while everyone outside that circle wonders whether $500,000 a year is Hayek’s road to serfdom.

In certain rooms, success no longer feels like success. It feels like missing the trade. It feels like climbing a ladder and realizing, halfway up, that the ladder was leaning against the wrong building. This is comparison despair: the feeling that someone else’s extraordinary outcome has somehow diminished your own life.

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Theories of Relativity

Humans do not experience prosperity absolutely but relatively. Leon Festinger’s theory of social comparison argued that people evaluate themselves by looking to others, especially when objective standards are unclear.

We do not compare ourselves to everyone, however. We compare ourselves to people close enough to feel relevant. A young founder does not measure himself against Warren Buffett. A software engineer does not wake up furious that Larry and Sergey built Google. Those comparisons are too distant to wound. What hurts is the person who looks roughly like you, went to similar schools, worked in similar rooms, and made one different career decision.

In this light, the SpaceX IPO or the Anthropic secondary market becomes psychological evidence of our own shortcomings. Of a race we’ve somehow unknowingly lost. When someone you can plausibly imagine being suddenly ends up with $30 million and you’re still grinding for 1% of who-the-hell-knows-what, you feel judged. Ashamed. A sense of worthlessness.

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Envy Is A Terrible God

Envy is not always useless. Psychologists distinguish between two types of envy: benign and malicious. Benign envy creates what researchers call a “moving-up” motivation. You see someone with something you want, and the pain pushes you toward improvement.

Malicious envy does something darker. It compels you to tear down vs build up. Richard Smith and Sung Hee Kim describe malicious envy as painful, shaped by inferiority, hostility, and resentment. Research on relative income and well-being suggests that people are influenced not only by how much they have, but by how much they have compared with the people around them. What begins as useful information contorts into indictment. Why them? Why not me?

The hard part about this particular modern moment is that the gaps are so large, so visible, and so sudden. In today’s world, the sudden vaulting of an ostensible peer into mega-wealth becomes metaphysical. It makes prudence look foolish, patience look naive, and hard work look like something you do when you missed the real opportunity. The universe has rendered judgment, and you lost.

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There’s Nothing Wrong With Love

I have friends who were in SPVs for SpaceX and Anthropic. Some will make more from those investments than they made selling their own companies. At other points in life, I may be ahead of them. Then someone else passes everyone. The scoreboard keeps moving.

I’ve thought about this a lot because I am not immune to it. I am human. Beset by the same emotional turbulence as anyone else. There are people who are barely aware of my existence whom I silently compete with every day. They represent something to me: a path I did not take, a potential I have not fulfilled, a version of myself I fear I failed to become. But after enough reflection (and enough economic cycles), I am getting better at quieting the part of me that insists I am losing.

There is a strategy.

It begins with a long-term orientation. It relies on the same basic principles that have always mattered. And it does not require my friends or colleagues to stay in place so I can soothe my own fragile ego.

That strategy is this: play your game. Simple. Easy. Cliché.

But also: timeless. Eternal. True.

My game is Pavilion: building community, and trust, and betting that in a world of infinite AI-generated content, fractured career ladders, and increasingly lonely professional lives, curated human networks become more valuable, not less.

That may be the right game. It may be the wrong game. But it is mine, and I understand why I am playing it.

The work is to keep building without letting someone else’s payout convince me my own path has become small. And when a friend wins, congratulate them quickly, before your insecurity has time to organize itself. Send the text. Make the call. Ask them how it feels. If you cannot be happy for other people, your world gets smaller every time someone else succeeds.

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Getting On the Bus

Comparison despair tells you the future has already been allocated. That is false. It has not been. I have lived through four bubbles now: the first dot-com bubble, the real estate bubble, the post-COVID SaaS bubble, and now AI.

Each one had the same emotional atmosphere. The winners looked obvious after the fact. The latecomers felt foolish. The people standing outside the trade convinced themselves they had missed the only train that mattered. Then the cycle turned, the world kept moving, and new opportunities appeared.

Experience has taught me something simple: there is always more time. Capitalism is an expanding system. It creates new markets, new companies, new assets, new games, and new ways to win. Perpetually and ceaselessly.

You may have missed this bus. You have not missed the bus.

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Go Long

But there is a difference between believing the future is open and pretending exposure is optional. You still have to be long the forces reshaping the world. Since 2000, the QQQ, the ETF that tracks the Nasdaq, has outperformed the S&P roughly 2-1, including the busts. Over long periods of time, the people who stay structurally exposed to technology win. You don’t have to catch every cycle perfectly. You just have to stay close to the compounding curve.

AI makes this logic more extreme. If AGI is partially defined as a system that improves at accelerating rates, the practical question becomes obvious: how do you get long that improvement? How do you make sure some meaningful part of your work, your portfolio, or your operating leverage benefits from the curve?

That is the work now. Not panic. Not envy. Positioning. Build around the shift. Keep enough capital, attention, and flexibility available to participate in the next leg of compounding.

This is what I mean when I say you must be long AGI.

You must be exposed to the forces that will transform work and productivity over the next 10 years. Somehow. Someway.

The best time to plant a tree was 20 years ago. And the second best time is this very moment.

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Comparison Despair

The great lie of comparison despair is that someone else’s success has closed your future.

It has not.

Their winning does not mean you are losing. SpaceX employees becoming millionaires does not prevent you from becoming one. Anthropic employees getting rich does not consume the universe’s remaining supply of upside. That is not how value creation works.

Many people can win.

The way you win is by making yourself useful to other humans, or increasingly, to their agents. The form changes. The principle does not.

So be ambitious.
Be exposed.
Be clear-eyed about AI.

Build something valuable. Make more money than you spend. Deliver value to customers. Stay close to the future. And when your friends win, try as hard as you can to be happy for them.

Someone else’s number came up.

Good for them.

The wheel has not stopped.
The game is still being played.
Keep playing yours.

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Next Week

Vertical Integration. Maybe Claude is going to wipe out every application layer company. But do you want to buy your washing machine from Con Edison? Even in the age of AI, the rule of comparative advantage still holds true. The provision of intelligence can be separated from the products that use it. And we don’t want the vendor risk of being completely dependent on one utility provider. We will need applications, even if they’re in different forms.

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Also On My Mind

A few other things on my mind. Let me know what else you might like me to write about.

• Read the Sebastian Mallaby book about Demis Hassabis then read The Player of Games in Iain Banks Culture series. The history of games. The meaning of the word. Our obsession with playing them and what they teach us about ourselves.

• Related to today’s essay, status and tribes (again). The seats in business class are objectively uncomfortable. But because they’re in front of even more comfortable seats, we love them. We are trained for status seeking.

Thanks for reading.

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