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...
Jan 22, 2026•19 min
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...
Jan 13, 2026•20 min
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. Grow your business: https://sweatystartup.com/ev...
Jan 04, 2026•19 min
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: https://sweatystartup.com/events Book: https://www.amazo...
Dec 26, 2025•19 min
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 fo...
Dec 17, 2025•20 min
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 busi...
Dec 14, 2025•1 hr 41 min
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...
Dec 08, 2025•18 min
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: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/dp/006338762X Newsletter: https://www.nickhuber.com/newsletter...
Nov 28, 2025•10 min
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 inter...
Nov 18, 2025•32 min
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 b...
Nov 08, 2025•22 min
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: https://sweatystartup.com/events Book: https://www.amazon.com/Swea...
Oct 29, 2025•18 min
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: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/...
Oct 19, 2025•18 min
Oct 09, 2025•17 min
Brandon and I dive deep into what it actually takes to build real businesses that last. We talk about hiring global talent, keeping overhead lean, scaling across multiple companies, and why most people overcomplicate everything. This conversation is packed with practical insights from two guys who have been through the fire and figured out how to win by keeping it simple and moving fast. Grow your business: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring...
Sep 30, 2025•23 min
I sat down with Shawn Nelson to talk about what it really takes to build something that lasts. We covered everything from spotting talent in the wild to shaking every tree to raise capital. I share the story of recruiting one of my best hires in a freezing Walmart parking lot and how that same mindset applies to building wealth through sweaty startups. If you're serious about business and tired of startup fantasy, this one's worth your time. Grow your business: https://sweatystartup.com/events B...
Sep 20, 2025•24 min
In this episode, I sit down with Greg Isenberg to talk about the types of businesses most people overlook. We get into sweaty startups, firewood delivery, nanny recruiting, Christmas light installs and how some of them quietly turn into million-dollar companies. I also share why I've spent over six figures on domains and why that's one of the best investments I've ever made. If you're trying to figure out where the real opportunities are, this one will give you a blueprint. Grow your business: h...
Sep 10, 2025•21 min
In this episode, I sat down with Zuby to talk about the deeper side of entrepreneurship, confidence, culture, and what it means to build a meaningful life in today's world. We got into AI hype vs reality, why the health system is failing men, the societal pressure against family, and how confidence, not intelligence, is often the key to success. If you're thinking long term about wealth, health, or raising a family, this one's worth your time. Grow your business: https://sweatystartup.com/events...
Aug 31, 2025•22 min
I joined Rohit to break down the real path to building wealth through business. We talked about picking the right boring business, building confidence when no one gives you permission, and why consistency beats intelligence every time. This is for anyone ready to stop analyzing and start taking action. Grow your business: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/dp/006338762X Newsletter: https://www.nickhuber.com/newsletter My Companies: Of...
Aug 22, 2025•15 min
Justin and I break down how to build real wealth starting with just 10K and no pedigree. We walk through starting boring businesses, raising capital with nothing but grit, and scaling through smart delegation and structure. We also get into how I acquired Somewhere.com and why building a media engine isn't just about attention, it's about leverage. If you're serious about business and want to skip the noise, this one's worth your time. Grow your business: https://sweatystartup.com/events Book: h...
Aug 13, 2025•18 min
Hannes Hennche and I break down why entrepreneurship isn't for everyone and what separates the winners from the ones who burn out. We talk about delegation, building leverage, and why following your passion is usually a trap. If you've ever wondered who should be running a business, how to build a team that doesn't rely on you for every decision, and why $50/hour work with no skill beats chasing unicorns, this episode is for you. Grow your business: https://sweatystartup.com/events Book: https:/...
Aug 02, 2025•18 min
In this episode, Taylor Avakian and I break down how leverage across every part of my business, from owning multiple companies to using AI to boost performance. We talk about how to structure a team, build a system that scales, and why most people fail at delegation and hiring. It's a real look at what it takes to grow without getting buried in the process. Grow your business: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/dp/006338762X Newslette...
Jul 24, 2025•17 min
In this episode, Taylor Avakian and I break down how leverage across every part of my business, from owning multiple companies to using AI to boost performance. We talk about how to structure a team, build a system that scales, and why most people fail at delegation and hiring. It's a real look at what it takes to grow without getting buried in the process. Grow your business: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/dp/006338762X Newslette...
Jul 24, 2025•17 min
Louis Shulman and I break down what it really takes to build a business that prints cash. We talk sales hiring delegation finding the right market and avoiding the traps that keep most people stuck. No theory just practical lessons from the trenches. Grow your business: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/dp/006338762X Newsletter: https://www.nickhuber.com/newsletter My Companies: Offshore recruiting – https://somewhere.com Cost segreg...
Jul 15, 2025•18 min
In this episode, I sat down with Simon Turner to unpack what real entrepreneurship actually looks like, beyond the social media fluff and one of the best ways to buy your time back. We talked about buying boring businesses, earning leverage through discipline, how everyday operators build extraordinary wealth and private aviation. Grow your business: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/dp/006338762X Newsletter: https://www.nickhuber.co...
Jul 04, 2025•15 min
In this episode, I sat down with Travis Chappell to talk about the real game of entrepreneurship, one that doesn't start with passion, but with leverage, discipline, and picking battles you can actually win. We got into why boring businesses outperform flashy ones, why real estate isn't passive, and how I ended up buying a $52 million company without anyone's permission. If you've ever been told to follow your dreams and hope it works out, this conversation will show you a more honest and more e...
Jun 21, 2025•16 min
In this clip, I sat down with Seth Stevens to talk about what it really takes to build something great. We covered why waiting for permission is a trap, how I went from broke and overlooked to building a much larger net worth and the truth about what successful people actually do to buy back their time. Grow your business: https://sweatystartup.com/events Book: https://www.amazon.com/Sweaty-Startup-Doing-Boring-Things/dp/006338762X Newsletter: https://www.nickhuber.com/newsletter My Companies: O...
Jun 11, 2025•19 min
In this episode, I sat down with Nick Hulewsky to break down the real story behind why I walked away from a secure win and went all in on building the hardest business of my career. We covered how I bought out my partner, why outsourcing talent changed everything for me, and what it actually takes to raise money and scale a company when you're betting on yourself. I shared what most people get wrong about hiring, the pressure of managing other people's money, and where I think AI is headed in al...
May 30, 2025•16 min
Most people are playing the wrong game. I used to think everyone should start a business. I don't think that anymore. In this episode with Al Elliot, we talked about why chasing the wrong career or business can leave you miserable, even if you win. I shared the story of a friend who did everything right, top law school, high-paying job, but realized he hated his life. We talked about how to pick the right game, why trying to change the world too early is a losing move, and how spotting real tale...
May 16, 2025•17 min
In this episode, Nick Huber and Adam Lush (@MindBranches) discuss life, business, and success during a live X.com Spaces conversation. They pull back the curtain on why most people underestimate their stress tolerance, how confidence is built by doing hard things, and why pride is the silent killer of great decisions. Nick explains why trying to invent something revolutionary is usually a losing game and why doing the simple things exceptionally well is the real path to wealth. Throughout this l...
May 13, 2025•1 hr 31 min
In this episode, Chris Koerner and I talk about what it actually takes to build something meaningful. Not the social media version. The real version. We talk about taking punches in business, dealing with hate online, and why most people have no clue what their stress limit really is. We talk about how real confidence comes from doing hard things and why most networking is a waste of time. We break down the role of a CEO, why delegation is a skill you earn, and why pride can ruin everything. No ...
May 09, 2025•15 min
