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.

Life offers two fundamental orientations toward experience: we can approach it passively, primarily responding to circumstances as they unfold, or actively, deliberately shaping our circumstances through intentional choice and action. Two Approaches to Living # I’ve found that cultivating an active orientation yields the most fulfilling results in my own experience. This approach centers on taking initiative rather than waiting for external prompts or direction. The active mindset recognizes that meaningful outcomes typically require deliberate action rather than passive anticipation.

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.

I’ve long aspired to build a sustainable, successful startup—one that generates sufficient revenue to support itself and provide meaningful compensation to its team members. However, I’ve reached a point where honest self-assessment has led me to pivot toward employment opportunities rather than continuing down the founder path for now. This journey has offered valuable insights worth sharing, particularly about the gap between startup mythology and actual entrepreneurial reality.

The Value of Attempted Adventures # There’s a fundamental distinction between hypothetical experiences and actual attempts—between wondering what might happen and discovering what does. I’ve developed a core philosophy that shapes my approach to life’s possibilities: attempting something meaningful and falling short creates infinitely more value than perfect execution of the safely achievable or, worse still, the perpetual contemplation of what might have been.