I chatted with Steve Keller, who bought two crime scene cleanup companies and sold them for $5.8 million in less than a year. This is one of the most unique business models I've ever seen, and Steve gave me a masterclass on margins, challenges, and how to run a crime scene cleanup business. 1:28 Working as a sports cameraman 3:40 Buying the first business 8:01 The second and larger business 10:09 Running the new business 22:03 How he financed the purchases 26:30 Red flags to watch for ...

I chatted with Jake Wurzak, CEO of DoveHill, a business that develops and invests in hotels. Jake told me about how he invests in hotels, a joint venture that almost went terribly wrong, and he even critiques the hotel we recently bought in Montauk, NY. Highlights: 5:03 Jake's first deal 12:44 A deal that went bad 20:48 Making mistakes (and why they're necessary) 22:10 Hotels as an asset class - What does Jake like about them? 30:07 Investing in an NYC hotel 37:02 Jake reviews Sieva's...

I chatted with Patrick Dichter, owner of Appletree. He walked me through how he purchased his first business, an accounting firm, for $1.3 million, and how he acquired 2 more tuck-in business acquisitions. We go over the wins, like how he's grown topline by 3.5x, and the losses, like how he lost 40% of revenue in one day on one of those tuck-in acquisitions. Patrick also helps business buyers evaluate the quality of earnings in businesses they're looking at, so he gave us some helpful advice...

I chatted with Jeffrey Jaeger, co-founder of Standard Communities. They manage $5 billion in assets with a portfolio of 190 properties. He told me how he got started in the business, how he found his initial niche, and tons of secret tips on how to buy, analyze, and manage real estate. Watch this one if you want to build your own real estate portfolio. 0:00 How he picked apartments over retail, offices, industrial 3:10 A word from Vesto 6:23 Buying 15,000 apartment units & finding a nich...

I chatted with Logan Leslie, CEO of Northern Rock. He owns dozens of automotive shops across the Southeast with more than $150 million + in annual revenue. Logan chatted with me about why he started a holding company, how he did his first deal, and dozens of other lessons from building his empire. Here are some of my favorite parts: 3:53 A message from Vesto 4:55 Why start a holding company? 9:47 Why the automotive industry? 15:08 First acquisition lessons 24:02 How he funded his first ...

I spoked with Bryan Rand, CEO of Rand & Co, who owns 9 platform businesses with $400 million in total revenue. Bryan breaks down how he buys businesses, the wild story of how he started a fuel delivery business, and how he teaches his kids entrepreneurship and investing. My favorite parts: 3:32 How he got started in investing 10:40 Bryan's first deal: Buying a cigar lounge in Atlanta 13:05 Best advice for getting started buying businesses 19:07 Starting a fuel delivery business 36:30 Ba...

I chatted with Aaron Harper, CEO of Rolling Suds Power Washing, about how he scaled a small $2 million/year local business into a 77-location franchise system in just 2 years. Aaron tells me about why the home service wave is coming to an end - and what's next in the "boring business" space: Commercial services. Aaron's franchisees wash office buildings, apartments, and even famous football stadiums. And there's a huge opportunity in commercial services that many are missing right now....

I spoke with Dave Gilbert, a holding company operator who bought two different businesses over the last two years with his partner. First they bought an accounting service for $2.8 million (Note: $3.8m was mentioned during the episode, but $2.8m is the correct figure). Dave walks us through some of the legal considerations of a non-accountant buying an accounting business, including how he expanded the services. Despite all the chaos that comes in the first year of buying a business, Dave and...

Gary Hoover knows more about American Business History than anyone else. He collected over 70,000 books, about half of which were business related, and studied each of them. Gary is a walking encyclopedia when it comes to business history. His expertise and passion is retailing, and he was at the center of the retail universe for most his careers. He'll talk about how he started a book retail chain that got acquired by Barnes & Noble, and his careers at several other prominent retail chai...

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 started, and he's bought some businesses himself - including a rollup of marketing SaaS businesses. Brian gives a masterclass on buying businesses. Highlights: 0:58 Going from lawyer to investor 9:25 Rolling up marketing software businesses 19:33 Selli...

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 acquires pool service companies, and how he's scaled to over $100 million in GMV. Watch this video if you want to build a home service empire. And if you're selling a pool company, contact Jeremy through his website cabanapools.com 0:35 Why Jeremy love...

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 about 3 years, earning himself a 24X return on his invested capital (most of the deal was financed with SBA debt, so he was able to make a large return on his down payment). Highlights: 5:19 Getting into ETA 7:17 Chris' search criteria 9:54 How long ...

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 clients and sold the business - and he didn't even know what venture capital was when he started the business. 0:54 Becoming an Operator & Investor 4:31 Esteban's risk profile when investing 9:32 Going into a new industry (buying schools) 21:28 Eco...

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 started by just buying one company, but soon found more attractive opportunities. 0:29 How he accidentally started a holding company 6:24 The first acquisition 9:25 Why not focus on one industry? 15:21 Structure of his HoldCo & how they get capital...

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. Moses manages hundreds of millions in real estate and has the battle scars to prove it. 0:00 Introductions 0:55 His first deal 12:35 How to find tenants 16:40 Quitting his job 27:20 Math on new acquisitions 30:20 Seeding new real estate operator 35:30 ...

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, including Flying Magazine. But his business model isn't just selling ads; its capturing an interested audience and selling them what they really want directly. One of those things is a fly-in/fly-out community in Tennessee with a runway, resort, sever...

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 teaches entrepreneurship and business to students and others, so watch this entire episode if you want to start a business. Mike will show you the way!0:00 Intro5:17 How did Mike become an entrepreneur?9:10 Mike's entrepreneurship lessons18:22 Entrepreneurial paren...

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 Ignite Tournaments.Khai shares insights from his journey from working on Wall Street to buying and operating 20+ businesses, his approach to building rapport with business owners, and how he built an empire of gymnastics studios across the United States...

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 his business, how the process went, and for some tips on lowering tax bills when selling a business.0:00 Intro0:57 How Ankur sold Teachable9:57 Structure of the Deal11:40 Why he raised VC money 14:45 How he went from retired to running his next business20:29...

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 much you can sell your agency for, and what his margins are. 0:00 Intro3:20 How David sold and re-bought his agency11:05 How much can you sell an agency for?13:50 Fire yourself from jobs before you sell18:03 Raising his prices from $5k to $25k per month22:1...