I like work, don't get me wrong. There's a certain dignity to it, and I'd go bonkers if I wasn't solving problems for somebody. I just don't feel the need to do the traditional 9 to 5 thing. Or the 8:30 to zomg o'clock thing, which is slightly more traditional for Japanese salarymen.

But I'd certainly go for maximum independence so going to work for a company if I don't have to (which presumably I won't have to if I sell a startup) is out of the question. I want to be able to pursue crazy projects that might or might not turn out to give results.

Oh, and I'd crank up on my knowledge of theoretical CS too.

I've looked into outsourcing to other people but find myself too much of a micromanager to get away with it. No-one deserves micromanagement so I avoid it. Everyone else seems to want to turn trivial tasks into big "projects" with budgets to match ;-) - but that's because they're professional coders with standards, whereas if I can use an off the shelf product or bash something messy together in Ruby in 2 hours, I'll do that instead.

Professional coders tend to gasp in horror at my philosophy and I can't blame them. I'm very much of the "duct tape" mentality when it comes to engineering. Thankfully, you can get away with this on your own non-critical projects.. (it's a bit like the welder who doesn't use a mask when doing his own stuff in the garage) but I don't advise it for career programmers because otherwise you'll end up on The Daily WTF every week ;-)

Side note: Having to do significant work in one's areas of weakness/aversion is what makes the initial phases of starting up disproportionately challenging.

I'd most likely do a startup again (and again) at some point, but angel investing could easily become a full time startup.

I'd also spend a lot of time setting up a non-profit that introduced young kids to technology at an early age. I was pretty lucky that my dad got me onto the computer when I was four. There are a lot of kids in bad areas of the world that aren't that lucky.

I guess in short, I want to help give people the same opportunities I had from people that believed in me. With a good amount of money, you can do that on a much larger scale.

http://blogmaverick.com/2008/03/09/my-rules-for-startups/

To me personally, thinking too much about exit strategies in an early phase startup seems like premature optimization. Thinking about what you're going to be doing after you sell a company that's just getting off the ground is bordering on mental autoerotica. It's like debating what you're going to do after you win a gold metal in the olympics when you've just started training. There's so much ground to cover between here and there that it'd be better to focus on making sure you qualify.

I have pondered this route, but it seems that in general, the research community / academia tends to "shun" those that don't do straight undergrad -> research.

I dropped out of my undergrad CS program to do my first startup. That was 15 years ago. When I decided to go back for a PhD two years ago, I still had to complete my undergrad. I'm finishing up this spring and will be starting at a top 10 graduate program in the fall. My grades from 15 years ago were not particularly good and my background is rather unusual. I wasn't sure how I would be viewed as an applicant. This was not a easy year for admissions and I feel I did extremely well.

I know two other people went back to study math after working for a while. One is now a grad student at Brown, the other is a postdoc at MIT.

My credit balance.

Personally, I am i. managing an open source project ii. picking up/tasking the kids to school (generally spending time with the kids) iii. biking regularly to get/stay fit iv. lunches with friends v. looking for the next "thing" I want to get involved in

Ahh .. but you can see I am a little older than you!

The people who do startups like the freedom of working on their own thing. That doesn't extend to just startups. Design video games, or direct a movie, or start a band.

A) Vesting period- after the initial sale, you take on the day job of either (a) doing what you were doing before, if you were properly aligned in incentive structure, or (b) doing something different that they bought your team for. For some, they find that they have now reached a state in corporate America that allows them to vault to the upper echelons of management, while others feel these days don't go by fast enough.

B) Soul-searching/vacation period- for those who don't stay after vesting, some people go and soul-search, Entrepreneur In Residence gigs, live 4-hour workweeks, travel copious amounts, become advisors or investors in other companies, or find their original cadre of friends to start hacking on stuff. Some start dating.

C) Next gig- depending on the riskiness of the individual, they may never sell another startup again and become the circling crew of technology professionals, others will compete with much furor with another startup, while others will forget their hacker roots and take $5M from a big VC firm on an unproven idea.

But if I succeed, I'll probably keep doing what I do now - code, blog and do startup once again.

Then id probably go and see the world and all of its wonders.

b) Setup a "Hey everyone, I got some money, and want to be an angel investor...send me your ideas." page. Invest into a couple of promising startups.

c) Start thinking of something new to do. And then do another startup.

I'd also work less when "not at work", and focus on my family.