Risk Management

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.

Beyond the Cautionary Tale: Survivorship Bias as Strategic Insight # Survivorship bias—our tendency to focus on successful outcomes while overlooking failures—typically enters conversations as a cautionary note. We’ve all witnessed this dynamic: someone celebrates a remarkable success story, only to have another person interject with the observation that “that’s just survivorship bias,” effectively suggesting we should discount the achievement as statistical noise rather than meaningful evidence.

Prediction represents one of the most fascinating aspects of human cognition—our attempt to anticipate future developments based on incomplete information. Throughout my experience with forecasting across various domains, I’ve developed a deep appreciation for both the value and the limitations of predictive thinking. The Prediction Landscape: Successes and Challenges # My forecasting journey includes both successful predictions and notable misses. Among the more accurate assessments were recognizing the transformative potential of software and internet technologies since the 1990s, identifying the market opportunity represented by Airbnb, and appreciating Bitcoin’s disruptive potential. However, even with these successful predictions, timing proved challenging—particularly with cryptocurrency investments where directional accuracy didn’t always translate to optimal entry and exit points.