I chatted with Brian Wolfe, an expert on M&A from all levels - he worked as a partner at a big law firm for 17 years, helping to close huge deals. Now he's in the world of ETA (entrepreneurship through acquisition). He helps searchers get s...

I chatted with Jeremy Yamaguchi, an entrepreneur who's built many empires in home services: with home cleaning first, then lawncare, and now pool services. We talk about the economics of the home service business models he's worked in, how he a...

Today I sit down with Chris Edwards, who bought a flooring business in Steamboat Springs, Colorado. He bought the business for $1.7 million, grew revenue by 50%, and doubled SDE (seller discretionary earnings). He then exited the business after...

Esteban Reyes talks with me about how he's built and sold 3 companies, and how he invests in other startups through his VC fund. His first business was a software company that helped banks identify fraud. He eventually signed over 400 banks as ...

Rafael Quinn is the co-founder of Alternative Holdings, a holding company with 9 portfolio companies in a variety of industries. In this interview, Rafael explains how he started a holdco by accident nearly 15 years ago. Rafael and his partner ...

Today I speak with Moses Kagan, a real estate investor and operator in Los Angeles. Moses goes over some specific real estate deals he's done, including how he got started with a rundown, half-renovated apartment building in east Los Angeles. M...

In this interview I chat with logistics entrepreneur Craig Fuller, who owns a data company and dozens of media properties related to logistics and transportation. Over the last few years, he's acquired a portfolio of print magazine publications...

Mike Beckham built Simple Modern into a $200 million/year e-commerce brand. I chat with him about how he got started, another business ventures he had (including talking his brother out of buying $1 million of Bitcoin in 2012).Mike teac...

In today’s episode Boring Businesses, I’m joined by Khai Nguyen, Founder of Powers Gymnastics, the largest multi-vertical acquisition firm in U.S. youth sports, and investor in several companies like OpenSea, Kraken Digital Asset Exchange, and ...

Ankur Nagpal sold his business, Teachable, for $250 million. Now, he's focused on making people aware of tax optimization strategies (inspired by what he wish he know when starting his business).I asked Ankur how he knew when to sell hi...

David Rodnitzky sold his agency for $65 million - and then bought it back for $5 million. And then he sold it again for way more than $65 million. Listen to this fascinating conversation about how to scale a marketing agency, how m...

Jameson Haslam left his banking & private equity career to start a boring, home deck business in San Diego. He's already grown it to $1.5 million in annual revenue in a couple years. We talk about why he chose a boring business, how he sold...

In today’s episode Boring Businesses, I’m joined by Josh York, founder and CEO of GymGuyz, the largest in-home and on-site personal training company in the world.Josh’s entrepreneurial journey is a testament to relentless grit, vision, ...

When buying a business, should you keep the old owner on or hire your own operator?The short answer is we've done both. In this video, I go into some examples and the nuances of when keeping the old owner on won't work. Let me know if y...

Today I'm answering questions from the audience. "How do I sell my business for the most money possible?" is one of the most common questions I get. Since I've bought 20+ companies at Enduring Ventures, I have a long list of criteria I look for...

I spoke with Aaron Harper, who's turning a boring business into a national franchise. He found Rolling Suds, a pressure washing business that does $2 million in annual revenue with 37% margins, and has sold 200+ franchise territories in less th...

I spoke with Johnny Robinson, an expert on the home cleaning business model. One of the biggest takeaways was how Johnny bought a $250k/year business for just $1k down with a creative deal structure that others can replicate. He also talked me ...

I talked with Dr. Peter Boulden, the owner of 8 dental practices in Atlanta. He taught me his strategies for shifting from a solo practitioner dentist to the developer and owner of 8 dental practices (and still growing).Highlights:<...

I talked with Eric Pacifici, founder of SMB Law Group LLP. His team has closed $950 million in SMB acquisitions last year alone, after founding the firm only a couple years ago. Eric grew his firm with a combination of his connections from work...

Today I chat with Shannon Jean, an entrepreneur who made most of his money buying and flipping electronic goods. We talk about the 10+ businesses he's started, how to raise kids in an entrepreneurial environment, and why you shouldn't follow yo...

John Caple is a partner & co-founder at Hidden Harbor Capital Partners. In this episode, we chat about John's investment strategy, operating principles, which industries he likes to invest in, and much more. John's firm focuses heavily on o...

Chris Koerner considers himself “addicted” to entrepreneurship. And the facts back him up: he has built and sold multiple 7-8 figures businesses in his lifetime – and doesn’t plan to stop any moment soon.  In today’s e...

Nick Huber sold his service business for 7 figures and now owns a self-storage portfolio with 42 facilities and over 1 million square feet.In today’s episode of Boring Businesses, I’m joined by Nick Huber, Founder of the Sweaty Startup,...

In today’s episode of Boring Businesses, I’m joined by Codie Sanchez, Founder of Contrarian Thinking, to explore the best (and less risky) ways to make a million dollars in 2024, what you should focus on as a business owner, why building an onl...

Cole Zucker bootstrapped Green Creative, a commercial-grade LED lighting company, to $40M+ in annual sales before successfully exiting the business. In today’s episode of Boring Businesses, I’m joined by Cole Zucker, former Co-Foun...