Me, I focused on "what can I do" and "what would I buy" - I think a reasonable, though very limiting, starting point.
My first problem was that amazon radically changed the market for storage (I started by selling storage) - my second problem was that sharing pagecache? bad idea. My third problem was that I thought using obsolete hardware was somehow a good idea.
So, uh, yeah. of my major problems, only one, really, was external. the rest were me being stupid. I guess that could fall into the "finding something useful" category. But then, I am mostly filling unserved price niches in existing markets. When I started there were already VPS providers out there; linode was one. I do believe I was the first to switch to xen.
>I say that finding something to create that is useful enough to give a modest one-man income, is a lot easier than finding one giving a multi-billion dollar payout.
I assume it's harder to make the 'big exit' companies... not that I would know. It's certainly a very different game, one that would be /much/ harder for my particular skillset. most 'big exit' companies seem to be more focused on selling to investors than on day to day cashflow. In my industry, if I sold out tomorrow, I'd get the value of my servers, plus about a years revenue. Now, there's no way I'd sell at that price, but that's market for a ISP or hosting company. Compare that to the valuation MySpace got. They got a valuation that assumed myspace would be the dominant social networking site for a long time. The valuations for friendster and facebook both reflected that same assumption. To me, that assumption seems ridiculously irrational.
Now, if you are going for a 'big exit' usually you have more than one founder, and some startup cash from someone else. Certainly, more work is put in, but is any one person's contribution more than what they'd have to contribute to get their own lifestyle business off the ground? I don't know. Once you involve investors, though, and people depending on investor money, you are much more likely to get yourself in a situation where you have no choice but to close the company.
Of course, my negative tone is entirely sour grapes, because my skilset means that I'd be a very minor player in any "swing for the fences" venture, while I can handle my lifestyle business just fine.