A while back I read Daniel Tenner's excellent article entitled Taking the Leap. Having run my own modestly successful startup for going on 7 years now, I can say with some authority that he makes excellent points. But one thing about the post bothered me: his advice is most applicable to your first startup. That distinction is critical.
Hacker News idolizes people like Steve Jobs, Elon Musk, and other visionaries who take incredible risks in the face of absurd odds. Their stories are dramatic, and it's delicious to read stories of people who buck the system and succeed. But it is a disservice to the less experienced to omit the beginning to every success story: the small successes they had early in life.
The men who mine asteroids and build electric sports cars don't start with those ventures. To illustrate my point, I'd like to tell a quick story.
Back in 2008, my cofounders and I were going door to door trying to raise a minuscule amount of funding. One of our business advisers gave us an introduction to a successful founder turned angel investor who had just sold his company. Everyone was talking about how successful he was, but over the course of developing a mentorship relationship, we heard about how he got his humble entrepreneurial start. He did it by selling asbestos file folders to legal consultancies at a time when everyone was going digital. The business model was in it's death throes, but he was able to generate enough profit to reinvest it on his next company.
Read that again if you missed it: our visionary angel investor got started selling fireproof file protectors to lawyers who wouldn't need them in a few years.
This sort of story is far from isolated. Success begets success. Elon Musk didn't start with Tesla, he started by selling a $500 computer game called Blastar at the age of 12.
Don't try and shoot the moon on your first startup. Bootstrapping reduces the upside of your ventures, but it also reduces the risk that you'll fail. Daniel Tenner has it right: keep your head down, reduce your burn rate, and if you succeed doing that a few times, Mars, cold fusion, and hover bikes will still be waiting.