"If you build something that solves a problem that people have (ie. is useful), and you arrange for people get to know about it somehow, then I think you can't help but be successful. But "successful" might not be a goldmine/lottery; it just might be making an adequate living, in a lifestyle business - like a fish n chip shop (as DHH denigrates). I think it's actually quite hard to fail at this, if you are aiming at creating something useful + communicating it."

This is what I'm doing, with some success. Now, if you don't count the net worth growth implicit in how the company is growing, I'm not making what I would be working for other people, but I think I'm a success. I set my own hours, my baseline expenses are covered, and when I hustle, I can make a lot of money. when I don't, like the last few months, well, like I said, my baseline expenses are covered. Also, eh, I've probably grown my reputation enough that my credentials now look better than they would had I spent this effort on college.

I don't know if I agree with the "can't help but be successful" part, though. I poured most of my income and spare time into projects like this for many years before I hit upon a project that actually worked. Now, part of that might be because I'm no superman... my IQ barely makes it into the 98th percentile, which really is kinda dumb. I never went to college, and, uh, I'm pretty lazy. I got a 2.16GPA in one of the worst high schools in the state. I mean, yeah. no two ways about it, I'm lazy.

So yeah, uh, if you are a Paul Graham, maybe starting a lifestyle business is easy. Maybe. but for me, it was a lot of work. Now, it was work that I liked doing; I think I enjoyed building my company more than I would have enjoyed taking the money and buying a porsche (and I'd be able to buy one with the cash I dumped in before it became profitable... two or three if I got a reasonable rate for the time I spent before the company became profitable.)

On the other hand, maybe what you mean is that you can choose to run a lifestyle business in such a way that you don't really fail until you choose to fail. This is what I did. When I ran out of money, I'd do more contracting, or get a full time job. When I was flush, I'd work more on my business. Really, I could have continued spending 3/4th of my income and time on the business for the rest of my life; unlike a startup with investors, there isn't anyone around to say "give it up" - it's just me. as long as I'm willing to work, there will be money.