The Sweaty Startup

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 es...

In this episode, I break down exactly how I went from running smaller businesses to acquiring a company at scale without giving up control. I share how I built my audience, why I went all in on Somewhere instead of cashing out, and how I structured a nearly $30M deal where investors got paid first but had zero decision-making power. I talk about the pressure of using other people's money, what I l...

In this episode, I break down how I think about hiring A players, why I move quickly on low performers, and how I build teams that can operate without me. I talk about why most leaders overcomplicate things, how slow decisions and poor standards drive great people away, and why focusing on simple, proven execution is what actually wins in business. Grow your business:   https://sweatystartup.com/e...

Chris and I talked about where real confidence comes from and why you cannot fake it. I shared how doing hard things builds confidence, why networking only works after you create real value, and how most people get this backwards. We also got into leadership, why you cannot delegate too early, and my honest thoughts on AI and where it actually adds value in business today. Grow your business:   ht...

Ryan and I talked about what actually separates people who build successful businesses from those who stay stuck thinking about it. We got into the mindset that drives real entrepreneurs, why urgency and action matter more than perfect planning, and how most people misunderstand networking. I shared the lesson a mentor taught me early in my career about sales being at the center of everything in b...

Austin and I talked about what entrepreneurship actually looks like when you start from nothing. I shared how my first business began by simply trading my time for money and why learning sales is the foundation of building any company. We discussed the early hustle behind Storage Squad, including chalk marketing on college campuses and hiring great people in unexpected places, along with the momen...

In this episode with Peter, I break down what really happened behind the scenes after buying Somewhere and scaling Bolt Storage through one of the most chaotic real estate markets in years. We talk about the pressure that comes with raising outside capital, why discipline in underwriting saved us when rates doubled, and how slowing down in storage led me to double down on building a global talent...

In this conversation with Roohi, I break down why most entrepreneurs are chasing the wrong game. We talk about starting with the end in mind, setting a personal cash flow number, and building boring businesses that actually stack the odds in your favor. I explain why speed is your only real advantage as a founder, how momentum compounds over time, and why making 30K a month in a proven business be...

In this episode with Chris and Chris, I talk about overcoming doubt, building irrational confidence, and using fear setting to make hard decisions less scary. We unpack lessons from chaotic early business seasons, anxiety filled moments, and the mindset shift toward extreme ownership that changed everything for me. We also cover leverage through hiring, auditing your time, focusing on sales and ma...

Jamie and I talked about why struggle is not something to avoid but something to embrace. We got into parenting, confidence, health, balance, and why giving yourself permission matters more than waiting for approval. We discussed what a good life actually looks like, how pressure shapes better people, and why playing the long game across generations is more meaningful than chasing status or shortc...

Nick Aufenkamp and I dug into the real reasons most entrepreneurs end up overwhelmed, broke, or miserable. We talked about delegation, generational wealth, and why the "boring" businesses often lead to the most freedom. I shared how I built leverage through international hiring, what I look for when choosing a game worth playing, and why long-term stress and sacrifice only make sense if you're cha...

Trevor and I talked through how I build real businesses by choosing better odds instead of chasing hype. I shared how I started from zero, tested demand with simple tactics, and why boring proven ideas beat trying to be the one in a thousand startup. We also covered pricing, firing bad customers, using data over ego, and why business never gets easier, you just get stronger. From building companie...

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...

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...

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 wh...

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....

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...

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 go...

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 execu...

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, an...

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...

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 escapi...

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 conversat...

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 believe...

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 i...