How I Lost $15 Million
A lot can happen in one year.
In 1996, I sold my first company one year after I launched it.
My cut? $15 million.
I’d gone from zero to $15 million in one year. I felt like I’d won the lottery.
But then, suddenly, a weird thing happened: $15 million felt like chump change.
I start watching these guys make $100 million, $200 million, and I’m thinking, “What’s wrong with me?”
So I started taking on insane risks.
Fast forward a year, I’m at an ATM staring at $143.
I lost everything.
Fifteen million to $143.
How? It’s easier to do than most people think.
You do it by not understanding risk.
Most people don’t understand risk. The world would be a better place if we did understand it.
Risk is the single-most important thing everyone needs to understand.
That’s why I recently had Nate Silver and Maria Konnikova on my podcast.
If you don’t know them, they’re two of the sharpest minds on probability and human behavior.
Nate Silver’s the guy who brought data analysis to politics.
Maria Konnikova took on poker to understand how luck and skill intertwine—she started with zero experience and ended up winning big at the tables.
They both agreed on one thing: most people get it wrong because they don’t separate risk from uncertainty.
They think they’re interchangeable, but they’re not.
Here’s the thing about making decisions: we’re constantly waiting for all the information, that perfect moment of clarity when we finally feel “ready.”
But that moment isn’t coming.
If you want to get good at decision-making, you’ve got to embrace the idea that you'll almost always be working with incomplete information.
Rather than letting that paralyze you, just jump in.
Poker players get this.
They’re used to acting on intuition, piecing together small clues, and accepting the inherent uncertainty of the game. And, really, life isn’t that different.
Try jotting down what you *do* know about a situation next time you’re stuck. Making a list of the known variables can clarify your next move and keep you from getting bogged down by all the unknowns.
BUT there’s a caveat: Start small.
I wish I’d started small after I sold my first company. Instead, I was throwing money everywhere.
Maria’s approach to this was personal.
She talked about how poker shifted her thinking about risk in everyday life, transforming her from a cautious player into someone who could handle a bit more chaos.
It’s not about flipping a switch and suddenly becoming fearless. It’s about easing yourself into risks that push your comfort zone, but don’t paralyze you.
So start small.
If you’re risk-averse, don’t go for the home run on your first swing. Instead, take small risks and build up your tolerance over time.
The experience will help you get comfortable with uncertainty, and over time, you’ll learn to weigh risk versus reward in a way that feels right for you.
One of the biggest takeaways here is to stay process-oriented, not outcome-oriented. It’s so easy to judge a decision by its results, but Maria and Nate argue that’s a mistake.
Even the best decision-making process can lead to a bad outcome—it’s just how probabilities work. When things don’t go your way, don’t immediately think you screwed up.
Instead, focus on whether you made the right decision with the info you had. If you did, that’s a win, regardless of the outcome.
There’s a LOT more tips and tricks like this in the full podcast.
It’ll change the way you view risk EVERYWHERE in your daily life.
