The Sweaty Startup

Mikk and I sat down to talk about what it really means to build a business that supports the life you want instead of trapping you in a cycle of stress and burnout. I walked him through the lessons I've learned from operating service companies, investing in real estate, and hiring globally to lower overhead. We got into how I've used boring, simple businesses to build leverage, why momentum is the most dangerous drug in entrepreneurship, and how I protect my time so I can focus on what matters. We also talked about content, writing the book, and the pressure that comes with growing a holdco while staying grounded. This episode is about discipline, delayed gratification, and building a system that gives you real freedom.

Matt and I talked about the kind of businesses that actually build wealth and why most people overlook them chasing trends that never pay off. I shared my story from Storage Squad to Somewhere and broke down how trading time for money is still the best place to start. We talked about the real odds of success, what Silicon Valley gets wrong, how to think about leverage, and when to finally hire so you can get back to doing high-value work.

Cody and I dug into the real side of entrepreneurship, what it actually takes to build wealth without chasing shiny ideas. I shared why I walked away from the tech startup fantasy and leaned into simple businesses that solve real problems. We talked through the ten minute drill, how I evaluate opportunity in any town, and why people waste years building businesses with zero demand. I broke down why your first business is about reps and skill acquisition, not money, and how boring work like tree removal or survey work can set you up for financial freedom faster than chasing passive income. This is a full breakdown of how to think like an operator, what the real wealthy people actually do, and why momentum is everything.

This is the full conversation I had with James Laidlaw about how he walked away from a high-paying commission job and built InHome Golf from scratch. We broke down how he scaled a golf simulator business during COVID, reinvested everything back into growth, and navigated the chaos that comes with explosive customer demand. Here's a photo of my simulator setup that James's company installed for me. https://x.com/sweatystartup/status/2011208892353851779 & Here's 22 other things that have that materially improved my quality of life: https://x.com/sweatystartup/status/2012556557674791016?s=20 If you want to reach out to James, email him at James@inhomegolf.com If you've ever thought about leaving your job or building a business of your own, this episode shows you what it actually looks like behind the scenes. Big thanks to James for joining the show. Check out InHome Golf here.

Brian and I got into what it really takes to make progress when you're stuck in a job, a business, or a mindset that's not working. We talked about how people overanalyze and under-execute, why momentum matters more than motivation, and the mindset shifts that helped me stop chasing the perfect idea and start stacking wins. I shared the story of how I built my early businesses, how I tested ideas without overcommitting, and how you can take control of your career path by doing common things uncommonly well. This one is for anyone who feels like they're waiting for permission to start.

Corey and I got into what actually matters when you're building a business and a life. We talked about what true wealth looks like beyond the money, why health and time freedom matter more than status, and how I'm thinking about the next 10 years. I broke down how I approach business growth, the truth about AI and electricity, and what most entrepreneurs get wrong about lifestyle creep. We also got into some honest talk about luck, operating skill, and why doing simple things well beats chasing the next big thing.

Jules and I talked about what building real wealth actually looks like and how most people completely misunderstand what it takes. I walked through the early days of Storage Squad, the financial mistakes that nearly broke me, and the pressure of borrowing millions before I knew what I was doing. We got into how one boring self-storage deal changed the entire trajectory of my life, why simple execution beats revolutionary ideas, and how I've kept my personal burn rate low even as my income scaled. This episode is about the long game, how momentum compounds, and why the most important number in your life isn't your net worth, it's your monthly freedom number.

I broke down my full trajectory from broke college kid to owning a portfolio of companies bringing in hundreds of thousands a month. I shared the hardest moments, crying on a Boston sidewalk after wrecked trucks and bad reviews, and why most people underestimate how brutal the stress can get. We got into the financial whiplash that comes with entrepreneurship, how I think about lifestyle creep, and why I still live like it could all vanish. I also walked through how I reinvested everything after my first seven-figure refinance, how I think about net worth vs cash flow, and what it actually costs to run my life, including the plane. If you want the unfiltered version of how I built this, this episode is it.

Jared and I got into the real truth behind why most people struggle to build a real business. I walked him through how I learned to operate, how I built my hiring systems, and why delegation and simple execution beat complicated ideas every single time. We talked about the mistakes entrepreneurs make when they overthink instead of taking action, how I built teams inside my portfolio companies, and why international hiring changed everything for me. I also broke down how I evaluate markets, how I test demand in ten minutes, and why most people should start with boring businesses before they even think about buying a company. This is the most honest breakdown of what actually works and what never does.

In this episode, I sat down with Andrew Giancola to talk about what actually builds wealth, ownership, leverage, and playing long-term games. We got into the mindset shifts that helped me go from a service business to raising tens of millions of dollars, and how Andrew made the leap from financial stress to financial freedom. This conversation is packed with lessons for anyone serious about escaping the treadmill and building something that lasts.

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.

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 multiple companies, why I spend 350k a year on my personal media team, and how building a brand on X completely accelerated my career. This episode is about unreasonable ambition, calculated risk and making moves even when nobody gives you permission.

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 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 Will Smith for having me on, follow him here: https://x.com/whentheresawill Check out more of his work here: https://acquiringminds.co/episodes Also shoutout to Niklas James from Minds Capital for co-hosting this conversation with Will. https://x.com/NiklasWJ In the intro, I mentioned that you should check out this episode from Acquiring Minds that came out just before Thanksgiving, episode 407 with Linh Tran. He quit corporate, bought a small HVAC business, scaled it, and now makes over $5M a year with a CEO running it for him.

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.

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.

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.

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.

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.

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.