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Episodes from The Sweaty Startup
The Truth About Private Jets (Built on "Boring" Businesses)
In this episode, I break down the reality behind private jets and why the people who own them aren't who you think. It's not tech founders or venture backed startups. It's operators running simple, "boring" businesses like HVAC, storage, and local services. I share how those businesses create real…
Stop Following Your Passion (Do This If You Actually Want to Get Rich)
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…
I Raised $30M Without Giving Up Control (How I Bought a Massive Business)
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…
Why A Players Leave and How Great Leaders Actually Build Teams
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,…
Why Confidence Comes From Doing Hard Things Not Thinking About Them
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…
Why Taking Action Beats Networking and Overthinking in Business
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…
Why Sales and Simple Service Businesses Still Win in Entrepreneurship
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…
Building Through Chaos: Raising Capital, Buying Somewhere, and Betting on Global Talent
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…
The Cash Flow Game: Playing the Odds in Business and Life
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…
Irrational Confidence, Extreme Ownership and Building Real Leverage
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…
Why Struggle Is the Point
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…
Why Most Entrepreneurs Burn Out and How to Actually Build a Life You Want
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…