The argument could be made that 2nd acts in tech rarely go well. See youtube founder getting sued by Kanye and others. There are of course exceptions.
Does anyone know the name of the instagram founders? Not really. They got money but only a little fame. If Evan sells out then maybe he is less known. Gamble but a chance at legendary status.
I guess goals matter. What is "reputation" and what does it mean, except for your future goal execution. If you want to start more companies, meeet more people, retire, etc.
I don't understand "legacy" or "legendary" status at all. Bill Gates may get a footnote in history, but what are you really chasing after for "legendary"? Do most people even know the YouTube founders? Does being a dead artist with legions of fans mean anything?
Now I'm getting existential, but I don't understand your comment on "fame." They should break into movies with their $20MM or so, or music if they so desire "fame."
Does anyone know the name of the instagram founders? Not really. They got money but only a little fame. If Evan sells out then maybe he is less known. Gamble but a chance at legendary status.