The Greater Fool: Why I Chose the Hard Path

There’s a quote from HBO’s The Newsroom that’s always stuck with me:

The greater fool is actually an economic term. The greater fool is a patsy. For the rest of us to profit, we need a greater fool, someone who will buy long and sell short.

Most people spend their lives trying not to be the greater fool; we toss him the hot potato, we dive for his seat when the music stops. The greater fool is someone with the perfect blend of self-delusion and ego to think that he can succeed where others have failed. This whole country was made by greater fools.

— The Newsroom S01E10

I’ve watched that show more times than I can count, and this idea has always resonated with me. I’ve never been afraid to be the “greater fool”—to take risks, to bet on myself, and to try where others hesitate.

The Economics of Risk

Being a greater fool isn’t about blind optimism or reckless abandon. It’s about understanding that meaningful innovation requires someone willing to challenge conventional wisdom. When I started Weaveu - my first real attempt at building something from scratch - most people thought creating a fashion marketplace that connected consumers with boutique tailors was overly complex. They were definitely right, but someone had to try.

The venture never made it past the ideation phase. The technical challenges were beyond our resources, and the market timing wasn’t right. But that “failure” taught me more about feasibility, market research, and the importance of technical validation than any business school ever could.

Learning Through Iteration

Each venture has been a masterclass in being comfortable with uncertainty. Altpack taught me that physical products require different skills than digital ones - and that sometimes knowing what you don’t want to do is as valuable as knowing what you do. Drool showed me that sometimes scaling down is the best way to scale up what truly matters.

When I attempted Learnway and aimed for Y Combinator’s first Fall batch, I knew the odds were against us. Building an AI-powered learning platform in two months while learning full-stack development? Classic greater fool territory. We didn’t get into YC, but that project transformed Drool from a design-only agency into a full-stack development partner.

The Philosophy in Practice

The greater fool mindset isn’t just about taking big swings - it’s about how you approach everyday decisions. When clients at Drool need something we’ve never built before, like the 3D interactive elements for SellScale or the AI-powered personalization for My Drip, the logical response would be to refer them elsewhere. Instead, we figure it out.

This approach led me to teach myself code, dive deep into AI development with Codemap, and now work on Winitiate - a unified platform for freelancers and agencies that might just be ambitious enough to work.

The Compound Effect of Foolishness

Here’s what I’ve learned: being the greater fool compounds. Each “failed” experiment builds capabilities that enable the next one. The T-shirt business taught me about customer acquisition. The design agency taught me about service delivery. The failed YC application taught me about AI development. The AI development taught me about building developer tools.

What looks like a series of disconnected ventures is actually a connected learning journey. Each failure makes the next attempt more informed, more capable, and ironically, less foolish.

Why We Need More Fools

In a world optimized for reducing risk and maximizing certainty, we need people willing to be the greater fool. Not because failure is fun - it’s not - but because someone has to test the boundaries of what’s possible.

If you’re reading this and you’ve ever felt out of place for choosing the unconventional path, for failing more times than you can count, or for believing in possibilities others overlook - you’re in good company.

Here’s to the greater fools.