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The Sweaty Startup

Dec 26, 2025

I sat down with Amy Calandrino to talk about one of the biggest traps in small business, owning a job instead of an asset. We unpacked the real difference between momentum and just being stuck on a treadmill, how real estate can either unlock freedom or bury you, and why most people overcomplicate entrepreneurship. If...


Dec 17, 2025

Tom and I talk about the moment I turned down a multimillion dollar cash-out offer and instead decided to raise twenty million dollars and buy control of Somewhere.com. I walk through how that deal came together, how I borrowed nine million from the founder, structured the investor tranches, and rebuilt the leadership...


Dec 14, 2025

This is the full conversation I had with Will Smith and Niklas James on the Acquiring Minds podcast in April of 2025. We broke down how I bought Somewhere.com, how I run my real estate private equity firm, and how I leverage offshore talent to scale revenue while saving costs.

We discussed how I think about building...


Dec 8, 2025

Nick Lamagna and I sat down to talk about what really happens when you're in the trenches, when the deals are falling apart, the pressure’s on, and you’re questioning everything. We got into the difference between chasing shiny objects and building real wealth through boring businesses, why the best opportunities...


Nov 28, 2025

Elijah and I dive into some of my most controversial takes, things I believe today that most people will agree with in 20 years. From mouth breathing and marriage to AI and heart disease, this episode is packed with stuff nobody’s talking about but probably should be. No fluff, just sharp takes and...