Your lifespan, healthspan, lifetime happiness and ability to run a company will only go up once you cash out for 4-10 million or more. You've literally solved the money problem at that point.
Why would you risk that on a vanity billion dollar exit?
It is basically the Achilles question, right? Durable since the classics: would you like to live long or die gloriously?
(Like most dichotomies, there are almost certainly options in the solution set not mentioned.)
Also, to rip off Sean Parker's character in "The Social Network", do you want to end up like Roy Raymond, who committed suicide after selling Victoria's Secret on the cheap, watching with regret as it grew into the billions?
Regardless of whatever imperfections the man may have had, he clearly knew how to motivate people. As portrayed in the movie, he seemed to have a powerful effect on Mark and the rest of the Facebook crew.
Do I think our product has potential for more? Yeah, sure (though it's still in development at the moment), but I'd rather have the security of having "enough" than the risk of waiting for a top-dollar offer and ending up with nothing if it never happened.
Which maybe means the start-up scene isn't the best fit for me in the first place, but I love what I do.
Here's a question to test if you really believe the argument you seem to be making:
You have the idea of your lifetime. It's a billion dollar idea. You are looking for a co-founder, and find two amazing prospects.
They are equal in every way (education, drive, interests, etc) except one: Jim spent the past five years working at a startup that he just sold for $20m. Tim spent the past five years working in an office job.
You can only pick one of them. Do you prefer Tim or Jim?
When you're looking for a cofounder, you're naturally biased toward someone with relevant experience, because the whole point of recruiting them is so that they can add value to the business and increase its chance of success. But when you're the initiator, a large portion of your contribution is picking the initial direction of the company, and what it's trying to accomplish. It's quite possible for first-time entrepreneurs to pick more ambitious goals and yet have less of a chance of success than repeat entrepreneurs.