Failure

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.

Speaking broadly, there are two ways to think about life: passively or actively. Passive philosophy amounts to letting things happen, whereas active is about making things happen. I generally try to stay active. If I want something to happen, I need to make it happen. Sitting around waiting for something to happen or for someone to come along and tell you what to do is passive.

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?

I really wanted to be a founder of a successful startup (where successful to me means the company can pay its own bills, and pay employees well). However the reality hasn’t matched my ambition and I’ve decided to find a job like a regular chump. I assumed that with work ethic, skills, persistence, and plenty of trial and error I could eventually find success. That hasn’t happened, and I’m nowhere close to making that happen. Being good at computers and working hard doesn’t cut it.