[SwellJoe]

Startup.

Before this one, I had another one for seven years (at some point it stopped being a startup and became a very modestly successful lifestyle business, which wasn't really what I was aiming for, so I shut it down). And when I get bored with this one, I'll start another.

I've frequently done contract work, on the side, to make ends meet. Even some quite long projects with great small companies--including another startup. But I've always known I would own my own business...since I was a kid. And I've always planned and acted accordingly.

[RobGR]

Just out of curiosity, why did you shut the "very modestly successful lifestyle business" down instead of selling it ? Obviously such businesses are hard to sell to the usual business purchasers (VCs or those business guys who buy franchises or whatever), but you can often find an relative or in-law or local stay-at-home mom who is willing to run it. You might have to be "on call" to consult and help them through problems. Was the business really so specialized that only you could do it ?

Myself, I currently work as a freelance programmer, and do some sys admin work to make ends meet while I try to get my other ideas under way. However, I am going to have to change something, as it is taking up more and more time and making less and less money. If I could get a job as a programmer where they were willing to let me work 2 or 3 days a week for proportionate pay, I think I would take it at this point.

[SwellJoe]

Was the business really so specialized that only you could do it ?

Yes, unless I sold it to someone who was roughly just like me, which narrowed it down to a half dozen people. It was an Open Source based business, and a big part of its appeal was the fact that a well-known developer on the project was the one supporting the systems and software.

Selling it would have taken more time for a questionable payout. I wanted to move on to other things as soon as possible (and while it's taken a little over three years, one of those other things is now able to pay about the same as the old business when I left it).

[nanijoe]

So you moved on to multiple things?

[SwellJoe]

I accepted that what I was doing was no longer making me happy, so I started trying other things.

I notified all of my customers (including a couple of long-term contract customers) that I was leaving the business, and spent a year or so tinkering with other projects that I'd started while running the old company. I knew I had several support contracts still outstanding, so I couldn't do anything serious for another year, anywa...so I spent the time tinkering and thinking about what I would really love working on.

One of them was Virtualmin, and after some thought, I realized it was the thing I enjoyed most--I'd been doing it pretty much entirely for fun, and the only thing preventing me from calling it a business was an assumption that the market was already saturated with products in that space. Turns out I was wrong; the other products in the space are bad enough, and the industry is big enough ($20-$40 billion worldwide depending on who you believe, though hosting is a mostly private equity industry, so very few public numbers exist) that following Paul Buchheit's advice of, "add 'done right' to the end of just about anything", works out fine.

During the tinkering phase, I also started building a simple Ruby on Rails app (yet another "disk space on the web" project, along the lines of Dropbox, though I didn't really solve the client-side, or try to...I was thinking DAV was the solution to that), I spent some time doing the math on a content filtering product I'd developed during the life of the old company (also a big industry, but not one I enjoyed), and thought about a number of other ideas. A wiki, a dating site, and a site for getting Open Source project features developed called Ransomware.com (this one probably would have been the winner had it not been Virtualmin--I still own the domain, and may do something with it for fun in a year or two).

Anyway, the important thing is that once I'd settled on Virtualmin as my next business, I dug in with a vengeance. Everything else was forgotten. In fact, I had to think pretty hard to remember what any of the other ideas and projects I tinkered with were when I started writing this reply.

[raghus]

very... and modestly...? :-)

[SwellJoe]

very... and modestly...?

s/modestly/minimally/, I guess. I had a hard time expressing it concisely. It kept me in food and houses and bought me a 350Z, but I never took vacations, and developed a pathological aversion to the sound of a ringing phone.