Basecamp was done almost entirely without risk. It was completely self-funded. We treated it as a side-product and a side-project until it could pay the bills. And only then did we make it the main focus of the company.
I absolutely hate risk. I think it’s a misnomer that entrepreneurs somehow are in love with risk and making big gambles and taking big bets. I think that’s probably true for some. It’s certainly not true for me. And I think it’s certainly not true for a large constituency of other successful entrepreneurs.
I think the act of putting yourself in a position where you’re not forced to take on all this risk and bet everything is the hallmark of running things well.
The comments are worth a read too. In particular, I agree with the assertion that if your job doesn’t allow you to have site projects, you should get a new job.