Just read Glenn's post on execs who've previously had success now getting involved in new startups, and Allen's post on what he calls the "community CEO" (referring specifically to Jason Calacanis getting back into the game with Mahalo). Both are about execs who've done well for themselves and now getting back in the game. (Reminds me of one of my favorite Yvon Chouinard quotes -- “only from the extremes of comfort and leisure do we return willingly to adversity”. )
I’m generally skeptical of execs AND founders who have already made a ton of money, and want to get back in the game. Why? I’ve witnessed too many highly comfortable individuals *want* to get back into the startup world because they remember the good days and they’re bored, but bail when they begin to remember just how hard it is to build a company. The more $ they made, the harder they’ve forgotten how to WORK.
Startups are hard, whether it’s your first or fourth. In my opinion, you’ve gotta have something driving you past the point where you consider giving up — the “eye of the tiger”. Maybe it’s pure competitive drive, maybe you just can’t stand the thought of having to get a “job”, or maybe you just have to show some assholes that you’re better than them.
Whatever it is, if you don’t have that drive and especially if you’ve already made your money — you’re far more likely to fail/bail when the shit starts to fly. If you do have that drive, then you can often bail yourself out of any situation (bad idea, for instance) and figure out the path to success.