"retired"; got tired of being "retired" after a month; started another company; took it public; tried retiring again; failed at that and started another company; sold it; hung around after sale; moved to help turn around another startup; left that and started another company; sold it; hung around a long time with the acquirer; moved to a competitor of the acquirer and hung around for a couple of years there; left the big company world to start another company; preparing for launch soon...
I guess not much :)
One thing selling did is give me a degree of financial freedom I didn't have before which is a big change. For example, my current startup (Keepskor, currently is stealth mode) is currently completely self-funded and will remain so until we open our doors publicly. I wouldn't be able to do that if I hadn't sold other companies before.
I probably should amend that. The financial freedom is great but it wasn't something I had aspired to when I did startup 1.
I have seen many people strive for the money and make it but then blow through the money quickly and be basically in the same position as the one they started in.
Don't do a startup for the money because if that's your main motivator, it likely won't work out. To anyone who doesn't have the kind of mental illness required to put themselves through life in a startup (anyone who wishes for long hours, continuous stress, a feeling that how much you do is not enough even when you win is probably some form of mental illness but I figured it's easier not to worry about it as I can't change it) probably shouldn't.
That said, if you have an idea that keeps you at night, or a problem that annoys you so much that fixing it is easier than letting it continue annoying you, then go ahead. I am the kind of person that sees something not working and think "I can fix that" which, for some problems, eventually moves to "I HAVE to fix that"... and all my startup entrepreneur friends have the same kind of feeling.
... but yeah, the financial freedom makes things easier. Wealth, however, didn't at first. A lot of money at a young age was really tough to manage. IF you happen to get the lucky gold ticket, don't touch the money for about a year. Just see what MODEST improvements you want to make to your life instead of going out and blowing the money. That way, the money will last longer and ensure that you can live worry free and build the next great startup.
In order:
internet.com (went IPO in 1999, acquired in 2008 (or thereabout, I was no longer involved when it was acquired)
Earthweb (went IPO in 1997, acquired by internet.com in 2000)
Net Quotient (acquired by Applicom in 1999)
Boo.com (crashed and burned in 2000)
Moveablemedia (acquired by HSBC in 2001)
I then did the Wall Street thing for a while, building cool payment stuff for banks and big tech companies.
Last year, I started working on the outline of Keepskor (not fully revealing what it's about except for broad stuff like the fact that it will be in the general space of social, mobile, and include things like localization :) ). Earlier this year, I left the cushy Wall St. job (I felt I was getting overly fat and happy) to focus on this full-time. The core ideas sketched out for Keepskor are still there but the way in which we're interpreting them have radically changed. We've done some market research to validate the core concepts, built a prototype, crashed and burned it, rearchitected and reengineered and are now getting closer to what I consider a solid alpha.
I guess not much :)
One thing selling did is give me a degree of financial freedom I didn't have before which is a big change. For example, my current startup (Keepskor, currently is stealth mode) is currently completely self-funded and will remain so until we open our doors publicly. I wouldn't be able to do that if I hadn't sold other companies before.