He's Done 200+ Acquisitions - Here's What The Online Business Acquisition Market Looks Like with Ace Chapman
Buying Online Businesses PodcastShow Notes
Most people think buying businesses is a numbers game. Ace Chapman has done 200+ acquisitions - and he'll tell you the numbers are almost never the point. Ace has been in this game since the dot-com bubble. He almost sold a stock market simulator to a little Nebraska company called Omaha Securities - before it became Ameritrade. He got out of a real estate business right before 2008 hit. He's not lucky. He's built a framework for thinking about business ownership that most acquisition guys never arrive at, no matter how many deals they close. But here's where it gets interesting. Right now, while everyone else is hunting online businesses in the U.S., Ace is doing something completely different - buying offline deals in Latin America, where business brokers don't exist and most owners don't even know selling is an option. Hotels. Spas. Mental health clinics. Panama. Colombia. Argentina. He walked into a hotel recently and heard the front desk pitch his own spa to a guest checking in. In this episode, Jaryd sits down with Ace to unpack why he thinks every business is just inventory - and why holding on too long is the real risk most buyers never talk about. How he structures equity deals so he never has to build anything from scratch. And what a real portfolio actually looks like when you stop confusing operating businesses with wealth. Most buyers are waiting for the market to calm down before they make a move. Ace just went and found a completely different market - one where nobody else is even looking. 🎧 Hit play - this is what 200 acquisitions of hard-won experience actually sounds like in practice.
Episode Highlights [03:33] - Ace explains why retirement is the riskiest first-timer move most people ever make - and why most people don't realize it until it's too late. [11:38] - The mindset shift that changed everything: why buying a business to grow it actually defeats the whole purpose of buying in the first place. [15:45] - Ace reveals why he's moved almost entirely into offline, international deals - and why Latin America is where the real opportunity gap exists right now. [26:00] - The tanning salon roll-up story: how Ace transferred managers between two businesses to fix operations and marketing - without hiring a single new person. [31:00] - The "Chairman Strategy" explained: why Ace treats every business need as an acquisition problem, not a hiring problem. [37:27] - Why every business is going to fail eventually - and why the most rational thing you can do is always be working toward the exit. [39:09] - Ace's reframe that changes how you hold a portfolio: businesses aren't assets to protect. They're inventory.
Key Takeaways ➥ Every business will eventually go out of business - even the best ones. 99% of the original S&P 500 companies are gone. The only question is whether you exit on your terms or theirs. ➥ The real portfolio isn't operating businesses - it's what you build outside them. Royalties, equity positions, brokerage accounts. Ace took a group of royalties public. That's the game after the game. ➥ Stop hiring. Start acquiring. Ace transferred one manager between two tanning salons instead of hiring twice. When he needed marketing, he bought social media accounts in the niche. You don't build what you can buy. ➥ Timing the exit matters as much as building the business. Ace nearly missed the Ameritrade deal in 2001 and almost held through the 2008 real estate crash. After 200+ acquisitions, his rule is simple - you're always working toward the exit. ➥ Go where the buyers aren't. In the U.S., acquisition culture is loud and crowded. In Panama, Colombia, and Argentina, business brokers don't exist. Sellers don't know "multiples" is even a word. That gap is the opportunity.
About Ace Chapman Ace Chapman has been in Micro Private Equity for decades! Buying his first business at 19 with just $3,000, leveraging it into a $70,000 acquisition. Over 25+ years he has personally completed 200+
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