Because the beach gets boring after a while. I sold a company at a young age and had enough money to not have to work for several years. I sat on the beach. I

Because the beach gets boring after a while. I sold a company at a young age and had enough money to not have to work for several years. I sat on the beach. I traveled. I had fun. Then I got tired of it. I really wanted to do something with my life. So I started another company. That one didn't work out as well as I'd hoped, so I collected myself and invested in/became co-owner of another company. That one has done really well. I don't need to start another company to make money. But I'm starting another software company now, and excited to do that. I am less motivated by money, and more motivated/excited to see this dream come to fruition. There are certainly some people for whom the beach doesn't get boring. I absolutely know people who exited for millions, whether as a founder or an early employee, and just retired. They won't be interviewing you, however. The people who decided to start again are the ones who have a kind of genuine excitement for making the world a better place, and their startup is a vehicle for them to do that.