1) IPO: I had already left and moved on to my next startup when the IPO happened. I put the money in the bank.

2) Acquisition: Stayed with the company for a year until they changed their minds and discarded what we had built, (this was the dotcom era, but we weren't a dotcom). I put the money in the bank.

3) Acquisition: Again, after I left for my next startup. Money went to the bank.

4) Acquisition: Stayed around for 3+ years until the PHBs took over cmopletely. Went to another startup. Put the money in the bank.

I've been amazingly lucky with my startups. Financially, each one made my life more comfortable, built a nest egg, helped pay for my kids' education. I keep saying "this is my last startup", but I keep going back. I am now in a position that I could "retire", but I'm at startup #5. This is my last one, this time for sure. If/when I do retire, I'll still be hacking interesting software, even if it's not for a company.

Out of genuine curiosity, what influenced your decision to put your money into the bank? Personally, I think that's a very smart decision, though I know a lot of people who've gone into the angel investor game to varying degrees of success.

I once fancied the idea of becoming an angel investor (and have made a few very small investments), but then I spoke to a colleague about that path, and he gave me the harsh reality of it. That doesn't mean I still don't fantasize about it, but I know it's a very different skill set than I already have.

Neurotic, obsessive contemplation of worst-case scenarios. Useful trait in a software developer, and it tends to make me conservative financially. But in many other aspects of life I don't recommend it. Also, angel investing doesn't appeal to me.

I bought some toys, but mostly a comfy life and peace of mind.

Oh man. You and I should compare notes (2 IPO, 2 acquisitions here) but I fully agree with you that luck is a big critical factor. People are generally impressed with my background but now on startup 5 or 6 (depending on whether I count my turnaround attempt for boo.com as part of the deal), I still feel that I'm just lucky and need to prove to myself that I can roll out another one.

I'm in the Boston area. If you find yourself in the area, get in touch (jao at geophile dot com)

Darn. Was just up there at Thanksgiving. I'm down in NYC myself. TNLNYC at gmail

Ping me if you ever come down in NYC...

wow! I hope to be able to meet you in person some day :)

The main thing for me was being able to pursue an idea no one would fund. I could self-fund it to the point where it was obvious people wanted it, at which point fundraising is easy.

And having done a few startups, I also had the confidence to not need anyone else to tell me it was a good idea. I just needed to build something customers would pay for. Those can be two very different things.

> I could self-fund it to the point where it was obvious people wanted it, at which point fundraising is easy.

I fall into the same category, except that I didn't bother with fundraising at all.

I knew that not having investors would be a simplification of the business, but I didn't appreciate just how much time it would save.

"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 guess the last para sums it up well. The degree of financial freedom would be something I would look forward to in life.

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.

Thanks! I'll definitely keep that in mind :)

That's impressive. What were all your startups, if you don't mind sharing?

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.

Your answers are going to be heavily biased towards those who got back into the game. Anybody that actually retired after their payday are highly unlikely to be reading HN.

Retirement doesn't exist. What happens is that your values change. Money is not the main driver of your daily work.

I work to:

- make an impact in other people's lives.

- earn respect and recognition.

- do something interesting and challenging.

- learn new skills (I never want to stop learning).

I "could stop anytime I wanted to" but I never do. I don't want to.

> Retirement doesn't exist.

This.

I actually took off but I only lasted 3 months before I was trying out things that turned into my new startup. I'm a failure at lying down with a pina colada on a beach... it drove me up a friggen wall to be honest.

For a long time I realized that there was a cognitive disconnect between what I meant when I said 'retire' and what people heard. This captures the 'after you don't need to please someone else in order to fund your daily life expenses' mode that I think of as 'retirement.' I know I'll be hacking new things and reading interesting papers and writing code right up until the point where the EEEG straightlines :-)

> I know I'll be hacking new things and reading interesting papers and writing code right up until the point where the EEEG straightlines

I haven't started any startups (want to so badly) but this line here resonates a lot with me :)

Going from needing to work to not needing to work is a major readjustment, and not always a positive one. A dream fulfilled means there is no more dream and a need to come up with a new one.

In short my life hasn't changed at all.

Though mine was a relatively small exit in comparison to some of these 9 and ten figure behemoths you hear about.

I thought I would not work for 3 or 4 years, that did not even last three or four months. But I still made time for fun in there too.

I was barely old enough to drink so I spent some time (and money) doing some stupid things (bought a bar once while I was hammered). Then I spent some time helping my dad's company get off the ground and primed for acquisition and now I am on to my 3rd startup.

Life only changed for me in the sense that I have less to worry about. As a whole I am still the same person and I still live basically the same.

I don't live a lavish lifestyle and I budget and save money like everyone else. I own a modest home and I drive a car which in not special (3 series).

I hope that I'll keep working until I am no longer physically capable but the most important thing to me at this point is being happy with what I am doing and spending time with my family and friends.

got into philanthropy

went traveling

did massage school

set up a big art space in LA

tried to set up a media incubator in LA

made some large burningman structures

moved to india

worked in a startup as a coder again

did another incubator

set up another art space

...

I find that not being 'hungry' has reduced my tolerance for spending time on activities which don't seem important. This can make me an awkward partner in some situations because the pursuit of money is a very good unifier.

Getting clarity on what I feel is important has been a much longer and more rewarding process than I expected.

Nice I like what you're up to..Lets set up art spaces :)

I now have the freedom to work on what I want to work on. I can take the time to brainstorm and build whatever I think needs to be built, rather than considering deadlines and having other people demand that I prioritize X or Y. I can take the time to explore avenues that I might otherwise have to scrap simply because of time/budget constraints.

As a coder, it landed me my dream job :)

Nice. But, I've always felt, if there was no time and money restriction, work would move at a lot slower pace than otherwise. Which would in turn impact our ability to launch. Has that happened to you?

Got married, moved temporarily from Oregon to Georgia with my wife. Got a dog, walking him a lot. Meditating a lot. Writing a lot. Working on three startup ideas. Loving life. Clarified what is important to me: being creative, learning, writing, freedom. Looking at building a new type of startup that has a structure that is additive to life and building fun things. I believe it is possible.

I believe it is possible also, good luck!

Moved abroad, traveled a lot, now in a PhD program.

resting & vesting & waiting for my 2 year anniversary

financial freedom, but other than that... no. would like to try it again to see if what happened was luck or skill.

Learned to surf, and started another!

Maybe it'd be different if it actually happens, but I can't imagine starting a second one without learning to surf and traveling the world first.

Living a life of debauchery can happen just as easily with much much less than a million bucks.

Heh, I misread that as "Living a life of douchebaggery" and heartily agreed :)

Well, the type of chicks that'd double up on a dude like me do.

Actually, no. While the money will give you the confidence to get what you want, you'll find that it was the confidence, not the money, that did it. "The Game" by Neil Strauss gives an engineer-friendly algorithm, and is a fascinating read overall.

I agree 100%. The thing is most of the men pulling stunning threesome one night stands are the type of men who unbutton 3 buttons on their shirt and have no trouble getting to a club alone and socializing with every social group in there. That is wether they arrive in a 100k super car or in a 85' Daewoo. Women like money and power, but they appreciate confidence a whole order of magnitude more. This probably applies to courting VC's and selling your product also. Balls is what give's a guy/gal the edge to succeed...

I run a magazine which counts Ross Jeffries (who was in TG) among its contributors.

Check it out :)

http://interestingtimesmagazine.com

Oh, and r/seduction on Reddit is teh shit.