I keep thinking there is a risk dimension here. Build for profit and the worst case scenario is, you have to wait to save enough to have financial independence.

I keep thinking there is a risk dimension here. Build for profit and the worst case scenario is, you have to wait to save enough to have financial independence. Build to flip and worst case is bust, start again. One strategy is lower risk then the other, pick the one you like best. But DHH does make a good point about the special scenario when your startup is indeed the most interesting thing you'll ever work on. Then after you flip it and decide retirement is not for you, you've already sold your best idea. I think that's a rare scenario, there's not much risk of "losing" the idea of your life. Then again, there's not much chance that any particular startup will be sold.