As a technology dude, I'm always interested to follow and read about technology businesses. I'm less interested in the rare super success stories like Facebook or whatever, but more interested in the smaller to medium success stories about companies that solve a particular problem, do it well, and have a nice niche and sustainable business.
What annoys me about that scene is the focus on the typical Silicon Valley story. Some dude has a clever idea, gets a shit-ton of VC money, works himself and his hires to death, and flames out (or rarely, sells out). It's the Hollywood blockbuster formula of business: Put enough crap out there and hopefully a few of them stick to make back your money. These are not the ideals that the really big success stories, like Google and Amazon, were built on.
That's why I find it inspiring to read the stories about people who build companies by bootstrapping their efforts, without taking outside money. Much of the advice from these folks suggests that you do what you can, with what you have, even if that means doing so in your spare time. In fact, that's the ultimate risk mitigation, because if you can build something after hours and it ends up failing, you still have your day job to fall back on.
The problem is that it's hard. If you're like me and have a low risk tolerance, a natural condition when you have a small mouth to feed, it's likely that you also value your time differently than someone who wants to go all-in. You like to spend time with your kids, make love to your significant other, travel, dine out, do some gardening or knitting, play video games, or whatever. So when you spend your day at your job, no matter what it is, it's really hard to engage in your "second job" at home. It's just hard to have that energy.
I very much fell into my business. While it has never been a quit-your-day-job thing, it has been a don't-need-unemployment thing when I've been laid-off. I never started content sites with the intention of making money, but they definitely fund my career development efforts and equipment purchases. I've found enough time and energy to continue to evolve them, just barely, for a dozen years now.
My next trick is a service that admittedly has a pretty narrow focus, but honestly, if it managed to keep 50 paying customers per month, I'd be happy as a clam. The problem is that I haven't been able to consistently sustain the effort needed to finish it. It's not hard work, it's just work, and work is hard when you spend your first eight hours in a day working. I'm not hitting my deadlines and milestones the way I'd like.
I suppose it's like anything else in life, that if you want it bad enough, you'll go get it. This particular thing has to compete with everything else, and sometimes it loses. Maybe a part of it is that I don't view it as a bigger thing. As I said, I view it as income augmentation, not a replacement for my day job. Perhaps that's the problem? I don't know... I need to go check on my kid.