Depends on how you define success and failure. I've had 7 failed startups (#8 is in the process of failing at the moment). I consider them all failures because I didn't end up with FU money. Funny thing is startup 6 & 7 really got me close.
Although, even if I won a billion dollar lottery, I'd still move on to startup #9. Half the fun is in the building anyway :-)
Agree that fun is in building the companies. But how long can you afford keep doing it (assuming you have family/commitment)? Success is what i call, you can keep doing what you like, not dependent on money, etc - iow, financial independence.
BTW, would be interesting to know the geographies of people who comment in this thread - say SF Bay Area, TX, MA, etc. That really adds new perspective to this discussion. My 2c.
I live in Oklahoma currently. I have done 5 of the startups in OK, one in CA (SF) and one in Texas.
You make choices in life and there are tradeoffs. I don't have kids nor do I anticipate having any. If they come, so be it. I partially left the Bay Area because I couldn't see even raising a hypothetical family there. That, the sticker shock never completely wore off and I never donned my rose colored glasses either :-)
I can afford to do it until the day I die. I've set myself up rather nicely in that regard. I'd be retired already if it weren't for my startups & first marriage. But being retired in your mid 30s sounds boring as well (I'm in my 40s now). However, I waffle on that position, so take it with a grain of salt.
Although, even if I won a billion dollar lottery, I'd still move on to startup #9. Half the fun is in the building anyway :-)