It can be dangerous to do path-not-taken analysis like that. If he sold it to idiots who ran it into the ground, he might now be saying, "I can't believe I sold my company to those assholes. Worst decision I ever made."
Some years back, The Economist covered a study that showed that half of all mergers destroyed value. And that was in pure dollar terms. A lot of acquirers do things that are financially profitable but still horrific to entrepreneurs.
I was recently talking to somebody who now suspects their company was bought mainly for negotiating leverage with some other companies who wanted the startup destroyed. I'm sure the acquirer came out ahead, but no matter how much I got paid it would have made me sad to see 5 years' labor destroyed. It might be economically more rational to sell my sick dog to a lab, but I'd still rather have it put down and bury it myself.