Entrepreneurship

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.

The distinction between growth and grind mindsets deserves serious examination. Growth encompasses a deliberate process of learning, skill acquisition, and personal evolution—typically following an upward trajectory. Grind, by contrast, represents pure exertion, often pushing toward exhaustion and burnout. One approach cultivates sustainable advancement; the other frequently leads to diminishing returns.

I saw a discussion on Reddit about entrepreneurship recently that got me thinking. What’s the point of being an entrepreneur when the odds of success are incredibly low? This is especially true if you’re low on resources or clout. Beyond the Silicon Valley Narrative # The dominant narrative about entrepreneurship has become increasingly narrow: raise venture capital, grow at all costs, aim for a massive exit, and hopefully become a billionaire. It’s the script that’s celebrated in tech publications, glorified by accelerators, and drilled into the minds of computer science graduates.

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.

Starting any company is hard. Startups are even harder. If you want to start a company but don’t have a business idea, then the first step is figuring out what to build. Is this…a startup idea?

I don’t like making predictions, but one prediction I do have is that many future big companies will be what I call “skin in the game startups” (you heard it here first). Having skin in the game simply refers to sharing risk and rewards with a counterparty. In startupland, angel investors have skin in the game: they give money to founders to help them start a business in exchange for equity with the hope that the business will become more valuable in the future. The investor is sharing the risk of the company (by outlaying their money), and if the company does well the investor will eventually reap grand returns.

Make something people want Y Combinator has a famous motto: make something people want. The first reference I could find to that motto was this blog post from Paul Graham.