When you want to start another startup. You could do that either because the old startup didn't succeed, or because you got acquired and are now finished working for the acquirer, or because although the old startup is doing fine, you decided to leave to do something new. We've had all 3 cases.

It’s unbelievable how candid and forthcoming you are as a business owner (YC being your business).

Is it wrong to assume that the value of YC diminishes with each additional serving? And as a follow-up, do you have any third (or even fourth) time founders?

I don't know. Obviously some of general stuff we talk about, you'd already know, if you'd done it before. But on the other hand maybe there are other advantages you'd be better equipped to extract the second time through. E.g. if I went back to college now I'd be able to learn a lot more than I did at the time.

I think I inderstand. I can now imagine it being sort of like watching a really fast paced and complex movie for the second time. A second viewing may enable you to peel off deeper layers of complexity (that you might have missed the first time around). Also, it can never hurt getting the YC stamp on your venture - again! :-) Thanks for the answer.