Three Offers, Zero Closings— Five Reasons We Failed to Sell Our Business
When it comes to selling a business, most owners have one goal:
💵 Get the highest price possible, all cash, and walk away clean.That was my mindset, too. And it cost me two years of my life, three failed deals, and a CASH FLOWING - PROFITABLE business I ultimately had to shut down due to life circumstances - and NO DEAL.
Here’s the truth: Being rigid about what you want can blind you to something better. There is a great saying I filter all my deal through today:
Our Two-Year Ordeal: What Went Wrong
730+ days on the market
Three buyers. Three contracts. Three full cash offers.
Three emotional gut-punches.
Here’s how it played out:
Buyer #1: Seven months of negotiations died because they wouldn’t honor our anonymity during the transition.
Buyer #2: Seemed solid, but a family emergency pulled them out.
Buyer #3: Six months of back-and-forth, only for them to bail the day before closing.
After that, we were drained. We dropped the price, hoping for a quick exit, and the vultures swooped in. Lowball offers rolled in like junk mail. It was offensive.
Eventually, we pulled the plug, closed the business, and sold off the license. We moved on, but the lessons stuck.
The Real Reasons We Didn’t Sell
Looking back, we didn’t just lose deals—we helped kill them. Here’s how:
We Overpriced the Business.
We marketed it as a 9.5 CAP, but CAP rates mean nothing if interest rates are too high. Debt service ate all the cash flow, and buyers walked.
Our Terms Were a Mess.
We demanded 50% down and stacked on a 10% interest rate for seller financing. It felt fair to us, but it scared buyers away. We could’ve charged 4%, made a healthy return, and closed the deal.
We Rejected Backup Buyers.
Our broker advised us to keep conversations going with other buyers while under contract. We refused, thinking it was dishonest. Turns out, it wasn’t—it was smart.
We Feared Creative Deal Structures.
We didn’t understand how private money lenders could fund down payments or how to handle the SBA loan’s due-on-sale clause. We avoided creative solutions out of fear and ignorance.
We Didn’t Want the Business Back.
We avoided seller financing because we feared the buyer might fail, and we’d be stuck with the business again. In hindsight, even if that happened, we could’ve shut it down and still walked away with a down payment and some cash flow.
The Mindset That Killed Our Deals
Here’s the mindset that sabotaged us:
“I’m not taking less than the max. I’ve poured my blood, sweat, and tears into this business. Don't even bring me offers less than my number.”It’s human to feel that way. But that mindset stops conversations and potential deals dead in their tracks.
Maybe that offer isn’t an insult—it’s a clue. A chance to ask:
What problem is the buyer trying to solve?
What risk are they trying to price in?
Is there a way I can solve that problem and increase the value of the deal?
Buyers have problems, too. If you can help solve theirs, you might end up with a better offer instead of no offer at all.
What We Should Have Done
If I could go back, here’s what I’d do differently:
Price the business based on what buyers care about: cash flow after debt, cash-on-cash return, and NOI.
Structure terms that make the deal easier, not harder.
Use seller financing or creative solutions to create a win-win - this opens you up to a MUCH larger pool of buyers.
Trust the broker’s advice, even when it feels uncomfortable.
Focus on net proceeds, not just hitting a number.
Think about the tax consequences of an all cash offer as opposed to a seller finance deal which spreads the taxes out over years - while also making you far more money than your max offer.
Become a student of deal structure. Talk to other owners, brokers, and sellers and find out everything you can about structuring a win-win deal.
If we had done just two or three of these, we likely would’ve sold for a fair price in a few months—instead of enduring a two-year ordeal.
Why the 20% Succeed
The top 20% of sellers get deals done not because they have better businesses—but because they have better mindsets.
They’re coachable.
They’re flexible.
They listen to buyer feedback and respond with solutions, not ego.
They know how to sell and how to help someone buy.
Final Thought: It’s Not What You Sell For—It’s What You Keep
Selling your business isn’t about getting everything you want. It’s about creating a structure where both sides can win.
A well-structured deal with tax advantages and steady income can put more in your pocket than a higher offer with poor terms and a tax bomb waiting at the finish line.
If I could go back, I wouldn’t just change the price. I’d change the posture, the approach, and the mindset.
That’s the difference between listing a business—and actually selling it.
Today I am partnered on millions worth of RV Parks with the exit planned out of the gate. I am blessed with the ability to help owners keep their parks, value their parks, and sell their parks. My first business exit wasn't the best - but it formed an education I am using to help guide others towards success.
