What I Learned Losing a Million Dollars (And Why Taleb Approves)

There are many books about how to make money. There are far fewer about how people actually lose it. What I Learned Losing a Million Dollars, by Jim Paul and Brendan Moynihan, is part confessional, part autopsy, and entirely brilliant. And for those of us who live in the biotech trenches—where fortunes can vaporize faster than dry ice in a heatwave—it’s required reading.

Jim Paul’s story is simple, brutal, and familiar. He was a rising star in the commodities trading world. He made money, got cocky, ignored the signs, and then blew up. Not in a symbolic sense—literally lost everything. A million dollars gone. Not to theft. Not to fraud. But to ego, denial, and a deeply human refusal to cut losses.

Taleb, of course, loves this book. And rightly so. He praises it not because it offers a clever formula for success, but because it catalogues—without flinching—the many, many ways success leads to ruin. It’s an anti-self-help book. A meditation on fragility disguised as a trading memoir. And, unlike most management literature, it doesn’t moralise. It observes.

Paul’s thesis is uncomfortably honest: there are countless ways to make money, but only a few consistent ways to lose it. And nearly all of them involve the psyche. Attachment to ego. Mistaking luck for skill. Chasing validation. Avoiding pain. This isn’t just about markets. It’s about being human.

When I first read it, what struck me most wasn’t the loss. It was the sequence of rationalisations that preceded it. The internal monologue. The refusal to sell because that would mean admitting failure. The adding to losing positions. The false belief that a rebound was inevitable. We’ve all done it. In trading. In relationships. In startups.

Especially startups.

Biotech is the perfect arena for this kind of cognitive trap. The timelines are long. The feedback loops are broken. You can lose money slowly for years, convinced that the inflection point is just around the corner. You double down. You delay bad news. You start to identify with the company. And when it finally implodes, you tell yourself it was unforeseeable.

But it wasn’t.

The real lesson of Paul’s book is not “don’t lose money.” That’s banal. The lesson is: don’t turn financial loss into psychological ruin. Don’t let your identity fuse with your trades. Or your startup. Or your valuation.

Taleb frames this beautifully. He talks about the “Midas curse”—the idea that those who experience success early often develop an illusion of invincibility. They attribute their gains to talent, their losses to bad luck, and slowly begin to believe that the rules don’t apply to them. Until, of course, they do.

In the biotech world, this curse manifests as founder syndrome. Or investor bravado. Or that charming spreadsheet that shows $10bn in revenue in year 7. You stop listening. You over-raise. You over-promise. And somewhere along the way, you forget that the goal is not to win every time. The goal is to stay in the game.

That’s why this book should be on every founder’s desk. Not because it’s comforting—it’s not—but because it shows, in excruciating detail, how easy it is to slide from “strategic conviction” into delusion. And how seductive it is to cling to positions long past their expiry date.

There’s a passage in the book that should be printed above every CFO’s monitor:

“The market doesn’t care about your ego, your narrative, or your cost basis. It just is.”

You could swap out “market” for “board,” “trial result,” or “FDA feedback,” and it would still apply. The universe is not judging you. But it will respond to your mistakes. Quickly, if you're lucky. Slowly, if you're not.

Paul eventually rebuilt his life. But the scars remained. And rather than bury them, he dissected them. That act—of intellectual post-mortem—is what makes this book so valuable. It’s not a how-to. It’s a what not to do. And in a world obsessed with winning, that’s a rarer and more useful guide.

So if you’re a founder, a trader, or just someone who’s ever believed too hard in your own pitch—read this. Not because it will make you smarter. But because it might just make you less stupid.

And that, as Taleb would say, is the foundation of antifragility.