Investing

The year is 2025. I’m turning 40 soon, sitting in a cramped 450-square-foot apartment with thin walls, $50,000 in credit card debt, and a credit score of 646. My financial worth: $100 in liquid assets. My net worth: deeply negative. Five years ago, I was worth over $7 million. This isn’t a story about market crashes or economic downturns. This is a story about human fallibility—specifically, mine. If you’re looking for a cautionary tale about greed, overconfidence, and the psychological pitfalls of sudden wealth, welcome. I’ve lived it all so you don’t have to.

Survivorship bias often gets discussed as a cautionary tale. For example, someone might point out a person’s or company’s success, and another will retort with, “But that’s just survivorship bias!” What’s rarely discussed is how to internalize survivorship bias in an actionable way. If you know that most success stories (whether in business, investing, dating, or even the actual lottery) are primarily the result of luck rather than skill, how can you use this information to your advantage?

Life is a series of random walks. Even if you walk the same path every day (in the literal sense), your individual steps on every walk you take are essentially random, and for the most part you aren’t even conscious of them because this is handled by muscle memory. When I say the steps are random, what I mean is that if you could precisely measure every step you take—where your foot lands, how much force you apply with your individual muscles—the data would reveal a pattern from a statistical perspective, but each individual step would follow a normal random distribution. In fact, research on human gait variability confirms this, with studies showing that step-to-step fluctuations follow statistical patterns characteristic of complex systems.

I remember when my first serious girlfriend broke up with me decades ago. Her chief complaint revolved around some recent incident, the details of which have faded from memory, but our conversation remains vivid. I pleaded with her, explaining how she was clouded by recency bias—focusing on the recent negative experience while overlooking all our positive history together.