For Stripe, YC was actually the first firm we took investment from. Doing so was a very easy decision.
Well there ya go.
A 5 million dollar exit and previous YCombinator experience (and the network that comes with that) would by my guess.
Steve Huffman did Reddit through YC and then Hipmunk again. I'm sure you would get an even better deal on the second round, so not sure what the downside is. The upside is still big.
Stripe is also funded by YC.
Thank God that YC backed a company taking on Paypal for consumer 2 business and business 2 business.
About time a YC quality company gets in that space.