By Michael Shea | Transworld Business Advisors of Tampa
When it comes to selling a business, everyone talks about the big finish — the signed contract, the wire transfer, the champagne. What doesn’t get talked about enough is just how many deals never make it to the closing table. And after two decades in this business, I can tell you: more deals fall apart than people realize, and often for reasons that could’ve been prevented.
You’d think the hard part is agreeing on price and terms — and sure, that’s critical. But most deals don’t blow up because of the number on the LOI. They die in the weeds. The little things: confusing contract language, personality clashes between advisors, or sellers getting spooked mid-process. I’ve seen everything from attorneys torpedoing deals with overreaching demands to CPAs forgetting they’re not the ones buying or selling the business. The devil really is in the details.
Preparation Is Everything
Let me be blunt: most failed deals trace back to a lack of preparation. Buyers jump in without fully understanding what they want or what they’re willing to pay. They fizzle out after 90 days of looking, frustrated that they haven’t found the perfect fit — often because they weren’t clear about what “perfect” even looks like. And when financing gets tough — which it often does — they bail instead of finding creative ways to get the deal across the finish line.
On the seller side, the biggest killer is ego. Sellers get hung up on what they think their business is worth, not what the market says it’s worth. I call it “valuation by gut feel,” and it’s a fast track to disappointment. Then comes seller’s remorse — especially with family businesses. One week they’re ready to list, the next they’re not answering the phone. Emotional attachment is real, and it needs to be addressed early.
Terms Matter As Much As Price
Here’s something I preach to every seller: it’s not just the number — it’s the structure. Deals die when sellers demand all-cash at closing or refuse to carry a note even when it makes the deal financeable. Flexibility on terms often gets you a higher price and better buyer. Insisting on your way or the highway rarely ends well.
And while the deal is in motion, sellers can’t take their foot off the gas. I’ve watched businesses lose momentum during due diligence because the owner got distracted. Revenue dips, the buyer gets cold feet, and just like that, we’re back to square one.
The Bottom Line
Deals are fragile. They require clear communication, realistic expectations, and a lot of patience. If you’re buying, know your criteria, get your financing lined up, and commit to the process. If you’re selling, be honest about your business’s value, stay engaged, and listen to your advisors — the right advisors.
And sometimes? Sometimes a deal just isn’t meant to be. When it feels like you’re forcing it, you probably are. In those cases, it’s smarter to walk away than waste time and energy. There are always more buyers. There are always more businesses.
Selling a business isn’t just a financial transaction. It’s an emotional one. My job is to help navigate both — and to make sure we’re chasing the deals that can close, not the ones that never will.
Thinking of buying or selling a business in Tampa Bay? Let’s talk. I’m Michael Shea, and I’ve been helping business owners get to the closing table for over 20 years. You can reach me anytime at yourfloridabusinessbroker.com.
Michael Shea represents the Tampa Florida Transworld office. In business since 2005, he has established a reputation as a trusted business broker across Florida’s key markets- from Tampa to Orlando, Melbourne, and more. Over the past two decades, Michael and his team have closed over $1 Billion in sold business volume and presided over more than 450 transactions. His credentials include the IBBA Certified Business Intermediary®, and most recently, the prestigious Certified Exit Planning Advisor® (CEPA) credential.