Built to Sell Chapter 12: The One Question That Changes Everything
Chapter 12 is called “The Question” and it’s one of the shortest chapters in the book. But it carries maybe the most important lesson for anyone trying to sell a business. You can have perfect financials, a great product, a solid team. And then one simple question at dinner can kill the whole deal.
Fancy Dinner, Simple Trap
Alex gets invited to dinner at Babylon, one of the best restaurants in the city. His broker Peggy Moyles has set up a meeting with RTX Printing, a division of a billion-dollar UK conglomerate. The president Alistair McGrath and his head of business development Simon Tupper are there.
The dinner starts with small talk. Alistair orders scotch. Simon gets a Grey Goose and tonic. Peggy and Alex stick to sparkling water. Smart move on Alex’s part. Though he does end up drinking wine later, which he regrets.
Alex does his homework. He asks questions about RTX’s plans for the US market. He describes his Five-Step Logo Design Process and his sales team. Everything seems to be going well. The steaks arrive. RTX’s shareholders are paying for expensive Napa Valley cabernet. Life is good.
Then the plates get cleared. Coffee is ordered. And Alistair adjusts his chair, looks Alex straight in the eye, and asks the only question that actually mattered the entire evening.
“So Alex, tell me something. Why do you want to sell your business?”
The Wrong Answer
Here’s the thing. Alex prepared for questions about cash flow, profit margins, sales processes. He had numbers ready. He had charts. But this one question, the most obvious and simple question in the world, caught him completely off guard.
His heart races. His face turns red. He stalls by wiping his mouth with a napkin. And then he answers honestly.
“It’s been almost ten years since I started the Stapleton Agency. We’ve had a good run, but I’m ready to spend more time with my kids and do some traveling with my wife.”
Alistair seems satisfied. Conversation moves to sports. Everyone says goodbye on the sidewalk. Alistair and Simon promise to get back to Peggy next week.
Alex thinks it went great. Peggy disagrees.
“I think they’re going to pass.”
Alex is confused. But Peggy has been doing this long enough. She tells him the whole dinner was window dressing. The only moment that counted was Alistair’s question. And Alex gave the wrong answer.
What Buyers Actually Want to Hear
So here’s the problem. Alex told the truth. He wants to sell, take his money, and go enjoy life. That’s reasonable. That’s human. But it’s the worst thing a buyer can hear.
Peggy explains it simply. Nobody wants to buy a ship where the captain is about to jump overboard. Buyers need to feel like you see a future for the business. That you’re excited about what the company could become with their resources. That you’ll stick around for a transition period.
The right answer, according to Peggy, sounds something like this: “I’m proud of what we’ve built. I’d like to create some liquidity for the value I’ve created so far, and I’d like to find a partner that can help us replicate the model in other cities. I want to share in some of the future growth.”
Notice the difference. Both answers are essentially the same situation. Founder wants money and eventually wants out. But the first one sounds like retirement. The second sounds like ambition. Buyers pay premium prices for ambition.
This is not lying. It’s framing. And Peggy is very clear about this. Her job is to get Alex the highest possible price with the largest percentage up front. For that to work, the buyer needs to feel motivated. And motivated buyers need to believe the founder is genuinely excited about what comes next.
The Second Chance
Alex gets another shot. Print Technology Group, the third largest provider of color printers in the US, comes along. Marcus Knightsbridge, their head of business development, puts Alex through a four-hour management presentation. Endless questions about sales cycles, processes, everything.
Then during lunch, when Peggy steps away to the restroom, Marcus asks the same question. “Out of curiosity, why do you want to sell?”
This time Alex is ready.
“We’ve proven the model can work in one city. I’m at a stage of my life personally that I’d like to create some liquidity for the value I’ve created so far, and I’d like to find a partner that can help us replicate the model in other cities and allow me to share in some of the future growth.”
He delivers it without stuttering. Without sounding too rehearsed. His only regret is that Peggy wasn’t there to see it.
The Private Equity Option (and Why Alex Says No)
Meanwhile, the business is doing great. Revenue for the first six months is over $2.4 million. They’ve already put $450,000 on the bottom line and are on track to exceed $1 million in pretax profit for the year.
But Print Technology Group goes quiet. Two weeks of silence after a great meeting. Peggy gets worried and presents a backup plan: Springboard Private Capital Partners, a private equity firm.
The deal would work like this. Springboard buys half the company at three to four times pretax profit. They inject about $1 million into operations. Alex stays on for five more years.
Alex shuts it down immediately. The valuation is too low. The company already generates enough cash to reinvest on its own. And staying on for five years is a nonstarter. He didn’t go through all this work to build a sellable business just to be locked in for half a decade.
Peggy takes it well. “My job is to bring you all of the options, that’s all.”
My Take on This Chapter
I’ve been on the receiving end of “the question” in job interviews many times. “Why do you want to leave your current position?” Same exact dynamic. If you say “I’m tired and want something easier,” nobody will hire you. Even if that’s the honest truth.
What struck me about this chapter is how Alex, a smart guy who built a million-dollar business, got blindsided by the most predictable question in the whole process. He prepared data and numbers but forgot about the human side of the transaction.
Buyers are people. They need to feel good about the deal, not just see good numbers on a spreadsheet. They need to believe the founder isn’t running away from a disaster. They need a story about the future, not just a report on the past.
In my years in IT, I saw this pattern constantly. The best consultants didn’t just deliver good technical work. They sold a vision of where things were going next. The ones who said “here’s what you asked for, I’m done, goodbye” never got called back.
The private equity subplot is interesting too. It shows that not all money is the same. Getting half the value at a lower multiple while being locked in for five years is not the same as getting full value from a strategic buyer who sees growth potential. Alex is right to wait for the right deal, even when the silence from Print Technology Group is making everyone nervous.
Sometimes the best move in a negotiation is patience. And a rehearsed answer to an obvious question.
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