What I Learned Losing a Million Dollars – A Modern Fairy Tale About Gambling in Business

I don’t read business books much anymore. I used to. Obsessively. At one point, reading felt like a compulsion—an intellectual sugar rush I couldn’t resist. These days, I prefer something sharper: peer-reviewed science, niche blogs, curated newsletters, specialized courses, and a healthy dose of GPT-fueled learning. Less time consuming, more frictionless, and far more adaptable to what I’m actually trying to do—learn and build.

But sometimes a book sneaks through the firewall.

What I Learned Losing a Million Dollars, by Jim Paul, came recommended by Sabin Gilceava.

This is an easy read - more of a business fable than a textbook. The story is compelling, a tale of gambling your way into (and out of) trading and business. It follows a tried-and-true formula: tell the reader simple but intriguing truths, sprinkle in some elementary insights from psychology and statistics, and package it all in a way that makes the reader feel smart. It’s accessible. It's a modern fairy tale - i.e. it’s about money.

It dances with ethical ambiguity. You keep wondering: is the author reflecting or justifying? It is not about value creation, nor business. It's about money, connections, bluffing, image, cheating, misrepresentation, risk, gambling, trading, speculation, money.

In that context, the introductory references to Edison or Ford are ironic. Please. Those men were engineers; they built things. 

That said, the book serves as a good reminder of foundational, state-of-the-art scientific and educational literature from psychology, economics, and statistics. The application of the five stages of grief (from pain management) to business loss is actually quite interesting. But like many books in this genre, it overstays its welcome, and sometimes exagerates with elementary truth until they become false. There’s a point where you realize you’re reading another 10-page explanation of why having a plan is better than not having a plan. And surely, both experience and research suggest that rigidly following an initial plan is usually a mistake, something the author simply ignores. Likewise, the value of objective over subjective decision-making is a repeated theme, in literature as well as in this book. Even though, surprisingly, it’s contradicted in the book’s very conclusion.

One quote stands out as a neat summary of the entire work:

“Most people who think they are investing are speculating. And most people who think they are speculating are gambling.”

Simple. Sharp. That wraps it up.