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the hard one

What the markets took, and what they taught

July 12, 2025 markets · honesty · the inner work

I’m going to write the thing most people leave off their personal site, because leaving it off would make everything else here a little dishonest.

I have made and lost more money trading than I'm comfortable putting in a number. The making felt like genius. The losing felt like weather. Both feelings were lies, and learning that they were lies cost me more than the money did.

The screen is a slot machine that flatters you

Here is the specific trap, and it’s worth describing precisely because it’s so well-disguised. When you make money trading, the market hands you a story in which you are smart. Not lucky, smart. You read it right. You saw what others missed. The dopamine arrives wearing the costume of validated intelligence, which is the single most addictive costume there is for a certain kind of person, and I am exactly that kind of person.

So you do it again. And for a while it keeps working, which is the worst possible thing that can happen to you, because it deepens the story. You’re not gambling, you tell yourself. Gambling is what other people do. You’re doing analysis. You have a thesis. You have, God help you, a system.

And then the weather changes, and the same screen that crowned you a genius liquidates you in an afternoon, and the story flips instantly to its mirror image: it wasn’t your fault, it was the weather, the manipulation, the bad luck. Both stories, the genius one and the weather one, exist to protect you from the boring truth, which is that you were never as in control as the wins implied or as helpless as the losses claimed.

The market didn’t take my money because I was unlucky. It took my money because I needed it to tell me I was smart, and it charges a fee for that service.

The quit cycles that didn’t take

I “quit” trading several times before I meant it. I’d take a loss, feel the floor drop out, make solemn declarations, move money into stablecoins, feel clean for a week. And then a quiet day would come, and the screen would be right there, and the story, you learned your lesson, you’re disciplined now, just a small position, would start whispering. The relapse always dressed itself up as a return to competence. That’s how I knew, eventually, that it wasn’t about competence at all.

What finally made the difference wasn’t willpower. It was noticing what the urge was actually for. It was never really about the money. It was about wanting a machine to tell me, fast and loud, that I was worth something. Once I could see that clearly, that I was feeding a self-worth problem through a financial instrument, the trade stopped looking like analysis and started looking like what it was. A very expensive way to ask the wrong thing for reassurance.

What it taught

I don’t regret it, exactly, which is a strange thing to be able to say. The losses bought me a lesson I could not have learned cheaper, and the lesson has nothing to do with trading.

It’s this: anything you do to make a machine tell you who you are will eventually bankrupt you. Money, metrics, likes, the chart, the dopamine of a green candle, they’re all the same instrument pointed at the same wound. The market just happens to be the one that sends you an itemized bill.

I build markets now. I think they’re one of the most beautiful pieces of social technology we have. But I hold them at a very particular distance, because I know exactly what they can do to a person who needs them for the wrong reason. The respect I have for them is the respect you have for a thing that once nearly took you apart.

Why it’s here

Because I’d rather you know this about me than not. The clean founder story, serial builder, onchain markets, the frontier, is true, but it’s the polished surface of something that has real scar tissue underneath. The scar tissue is where the actual judgment came from. I trust myself around markets now precisely because I’ve been on the wrong side of my own relationship with them, and I came back with my eyes open.

What the markets took was money and a year of stability. What they taught was worth more, and I only got the second part because I was finally willing to look honestly at the first.