I think the correct lesson is a little different. First, if you do rake in corporate money, and don't spend it all, you'll have a nest egg which gives you so m

I think the correct lesson is a little different. First, if you do rake in corporate money, and don't spend it all, you'll have a nest egg which gives you so much more choice in how you live the rest of your life. Second, if you don't have a nest egg - yeah you can't just gamble that you'll build software-as-a-service and instantly be making enough money to live. As he said, people assumed he'd use freelance to make up the difference. He didn't, but it is an option. Now freelance/contracting can be nearly as corporate as a full-time office job, and it isn't as stable an income, but it can pay really well. For many software engineers three months of full-time contracting could pay for a year's worth of expenses. (Assuming you make choices that align with that goal.) This would let you spend a great deal more time focusing on your business goals, and give you some freedom to fail some of the time.