Ed Weeks describes how founders selling their companies often fall into a trap: they agree to stay on, lose motivation, miss earnout targets, and end up with a fraction of the sale price. The real problem isn't laziness but grief at becoming an employee in a business they built.
So, let's draw the actual trap, because once you see it, you can't unsee it. Step 1, you sell. Step 2, you agree to stay on, which feels generous and safe. Step 3, you slowly lose real control, because it is not your company anymore. It is theirs. You just work there. Step 4, with control gone, the motivation goes. That's the vacation. Step 5, motivation gone means the numbers slip, which means you miss the earnout. And step 6, you walk away with a fraction of what the headline number said. The headline price was never the real price. The structure was was the real price, and the structure assumes you stay cooked, hungry, and in the chair for years. The buyer is not betting on your business. He is betting on your stamina. The vacation tells him he's about to win that bet. Here's the human part nobody puts in the pitch deck. I talk to these founders all the time, and when a deal falls apart, it is almost never about the money. It's about this. I had an owner tell me flat out, Ed, I am not reporting to some 28-year-old kid with a spreadsheet who has never made a payroll in his life. That's the real deal killer. These are people who built something with their name on the door. The thing they cannot stomach is becoming an employee in their own house, taking notes from a young associate whose only job is to ask why margins dipped in Q3. So if you are buying, understand that. And if you are selling, understand it about yourself. The vacation is not laziness. It's grief. It's a founder mourning the company that stopped being his the day he signed. The smart move is to see that coming before the ink dries, not after. So here's your homework, and it's the same whether you're buying or selling. One,
