Libsyn Directory

How I Raised Twenty Million to Take Control of a Fifty Million Dollar Company

Release Date: 12/17/2025

How to Win in Business Without Getting Trapped in Your Own Job

The Sweaty Startup

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 you’re serious about building something durable, not just flashy, this conversation is worth your time. Grow your business: Book: Newsletter: My Companies: Offshore recruiting – ...

How I Raised Twenty Million to Take Control of a Fifty Million Dollar Company

The Sweaty Startup

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 team while still running Bolt Storage and RE Cost Seg. We get into why I believed the company could become a publicly traded business and how my media brand helped me raise over forty million for storage, somewhere and other deals. I also explain how I split my time across...

How I Pulled Off a $52M Acquisition | with Acquiring Minds

The Sweaty Startup

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 , 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 teams, why sales is the foundation of all businesses, and why buying a company isn’t a shortcut, it’s a challenge most people aren’t ready for.If you're thinking about buying a business, this episode will show you the side of acquisitions people rarely talk about. Big thanks to...

From Chaos to Capital: How I Built Wealth Through Grit and Smart Bets

The Sweaty Startup

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 aren’t always the loudest, and how who you surround yourself with can either push you forward or keep you stuck. If you’re trying to figure out how to play the long game in business and life, this one’s worth your time. Grow your business: ...

Controversial Takes That Might Save Your Life

The Sweaty Startup

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 honest conversation. Grow your business: Book: Newsletter: My Companies: Offshore recruiting – Cost segregation – Self storage – RE development – Brokerage –...

How I Bought a Business, Built a Global Team, and Survived Internet Hate

The Sweaty Startup

I went from running a student storage company out of college to owning 63 self-storage facilities, building a global team across five continents, and acquiring a multi-million dollar recruiting business. In this episode, I sat down with Will Smith and Niklas from Acquiring Minds to break down how I structure deals, why offshoring changed everything for my operations, and how I think about building in public, despite the hate that comes with it. We also talk through the tradeoffs of chasing internet fame vs. quietly building real businesses. This one goes deep. Grow your business: ...

How Great Founders Build Stress Tolerance and Teams That Win

The Sweaty Startup

Alisa and I dug deep into what separates great founders from the rest. We talked about building stress tolerance like a muscle, hiring people who actually care, and the difference between delegation and abdication. We also got into the trap of chasing arbitrary net worth goals and why most entrepreneurs dramatically overshoot what they really need. This episode is full of real stories, honest takes, and a look at how I think about leadership, wealth, and building companies that last. Grow your business: Book: Newsletter: ...

How to Make Millions as a Solo Operator Without Building a Big Team

The Sweaty Startup

In this episode, I sat down with Rod Santomassimo to talk about building a lean, profitable business without chasing scale for the sake of ego. Rod’s a master at helping solo operators punch above their weight by focusing on systems, discipline, and value. We get into why bigger isn’t always better, how to grow revenue without growing headaches, and the underrated power of operating with clarity and intention. Grow your business: Book: Newsletter: My Companies: Offshore recruiting – Cost...

How Discipline at Home Builds Winners in Business and Life

The Sweaty Startup

Dustin Burnham and I sat down to talk about parenting, leadership, and the hard lessons that shape resilient people. We dug into what it really takes to raise kids who can think for themselves, handle stress, and create value in the world. From letting them feel real consequences to building habits that outlast trends, this one’s about long-term thinking, at home and in business. Grow your business: Book: Newsletter: My Companies: Offshore recruiting – Cost segregation – Self storage...