The Sweaty Startup · 2026-07-03 · 16 min
In this episode, I break down why "follow your passion" is some of the worst advice in entrepreneurship and what you should be doing instead if you actually want to make money. I explain how I think about choosing businesses, why boring industries like self storage and service businesses win, and how cash flow gives you leverage to solve bigger problems. I also get into what's happening in real estate right now, why most new investors are getting it wrong, and where real opportunities are opening up as weaker players get pushed out. I share the story behind acquiring Somewhere, raising $20M, and why big opportunities are never comfortable but worth taking. And most importantly, I explain why building wealth is a long term game, not an overnight success story, and how thinking in decades instead of months changes everything.
The Truth About Private Jets (Built on "Boring" Businesses)81 / 100I Raised $30M Without Giving Up Control (How I Bought a Massive Business)Why A Players Leave and How Great Leaders Actually Build TeamsWhy Confidence Comes From Doing Hard Things Not Thinking About ThemWhy Taking Action Beats Networking and Overthinking in Business