Hi Reader I want to say something most people in the ETA space won't say out loud. Most deals don't fail because of price. They don't fail because of structure. They don't fail because the SBA got difficult or the seller's attorney was unreasonable or the lender added a condition at the last minute. Those things happen. But they're not why deals die. Deals die because buyers don't have a system. They're improvising through one of the most complex, high-stakes, psychologically loaded...
26 days ago • 5 min read
Hi Reader I want to talk about a critical skill you need if you want to be a successful buyer who lands solid deals and, more importantly, actually closes them: "Deal Empathy." Here's what it's all about: Most people think deals fall apart because the numbers don’t work. After sitting through enough closings—and just as many deals that never made it there—I don’t think that’s true. In most failed deals I see, the math was fine. The valuation was defensible. The financing was workable. The...
about 2 months ago • 9 min read
Hi Reader This is important. If you've been reading headlines, then you need to read this issue. There’s a category of risk most business buyers don’t even realize exists. Not a bad seller.Not inflated add-backs.Not a deal that just “didn’t work out.” This is about buying a business that has been systematically overbilling, misbilling, or fabricating revenue—often for years—without the buyer realizing it. The danger isn’t theoretical.It’s active, growing, and concentrated in specific...
3 months ago • 5 min read
THE MOST DANGEROUS “HELP” IN SMB ACQUISITIONS Every week, a buyer sends me the same innocent-sounding question: “The broker sent over their purchase agreement form. They said it’s standard. They said it’ll save time and legal fees. Should we just use it?” This is not a negotiation question. This is a survival question. And the answer is a hard, non-negotiable: No.Not “probably no.”Not “in some cases.” A 100% NO. Because what you’ve just been handed is the deal equivalent of a Trojan Horse —a...
4 months ago • 4 min read
Hi Reader Today I’m going to share a deal structure that’s not for every seller—but when it fits, it can unlock opportunities most buyers never see. It’s not some new universal framework.It’s a niche tactic for a specific kind of off-market owner: They’ve built a solid business, but it’s not “broker-ready.” They’ve thought about retirement, but never made a plan. They don’t need a big payday — the house is paid off, the lifestyle’s comfortable. They’re proud of what they built, a little...
6 months ago • 4 min read
Hi Reader If you've been around business acquisition circles for any period of time you've undoubtedly heard of the "F reorg." It's one of the most powerful buyer tactics but also one of the most misunderstood. After closing upward of 140 deals and helping folks plan many more, I've seen lots of angst about F reorgs: Misunderstanding what it is Bad advice about how to do it Worry about complication Concerns over deal delay Mistakes (including bad ones) when folks other than tax lawyers...
6 months ago • 6 min read
Hi Reader Did you know there's a number more important than "SDE" when it comes to buying a business? That number is "NWC" or Net Working Capital, and whether you don't know what the number is, or you know it but ignore it when structuring your deal, the outcome is the same: You'll run out of money. We're not just talking about running out of money figuratively, but literally. It means you might close on your deal, and technically own a multi-million dollar business, but 30 days in, when you...
7 months ago • 5 min read
Hi Reader Today I’m going to talk about something that comes up frequently in deals I review—seller or key employee dependency. It’s more common than most buyers think, and it’s one of those risks that can quietly derail your first year of ownership if you don’t catch it early. Why should you care? Because you’re not just buying financials. You’re buying continuity.And if the seller (or one key team member) is the glue holding everything together, then you're not buying a system—you’re buying...
8 months ago • 8 min read
The deal looks solid. ✔️ Strong SDE✔️ Clean books✔️ Great reputation Then one line in the CIM rewires your brain: “One customer accounts for 35% of revenue.” Discussions with the seller and your QoE indicate that the issue worsens, with a more accurate estimate of around 50%. You don’t flinch at the numbers.You flinch at the psychology. Because this isn’t just a financial question. It’s existential. 🚫 Most Buyers Walk The common advice? “Too risky. Walk away.” And sometimes, that’s right. But...
9 months ago • 3 min read