You missed Sama's awesome post on "How to Get Into Y Combinator" (which is sadly now private) Here are some good sections:<p>For most startups at this stage, the best predictor of success is the founders. So, the most important parts of the application for me are the questions about the founders' backgrounds and the most impressive things they've done. We're looking for evidence that the founders are smart, effective, and determined. If you can't go through your application and point to evidence for all three, that's bad. Don't be shy about telling us why you're good, but don't write a bunch of meaningless marketing speak either.<p>The first question I usually ask is something like "so, why this idea?" I'm happy when founders say things like "we wanted this for ourselves" or "we understand this space better than anyone else because of Y". We ask about parts of the business we have concerns about, like market size, competitive differentiation, growth plans, business model, etc. In particular, I'm interested in seeing how founders react to new information, and if they're flexible while still standing their ground on things they believe in. If I've already thought of everything a founder has to say about his/her company, that's bad.<p>It's important to remember that most investors are optimists by default. We want to believe that we've just found the next Facebook.
Sam invested in Stripe's very first round.<p>His advice has consistently been clear, useful, and correct. He's also gone way beyond the call of duty in helping us on a number of occasions.<p>Though this is only tangentially related to the story, I'll take the chance to say: if you ever happen to have the chance to have Sam invest in your company, I strongly recommend availing of it.
Sam was one of AdGrok's angel advisors. He is <i>intense</i> in person. He talks quickly, and his signal-to-noise ratio made us all take notes during our meetings as fast as we could write and type.<p>As an example, he told us that our company's valuation would fluctuate wildly up and down, that timing our investment rounds was critical to our success, and that valuation is driven as much by hype and gossip as by real value--especially in the early stages. It was all stuff that just rings true to you immediately, but that insight isn't apparent or obvious without experience.<p>(Thanks for the help, Sam!)
We had Sam in our (2nd) YC interview for W12, unfortunately we were rejected but we contacted Sam a few days afterwards and he generously offered to give up his time to sit down with us in his office for a general chat about the interview and to offer some advice on our startup. We really appreciated that.
I have not yet been a part of YC, but know a fair number of YC founders. But among all people I know, I found Sam to be probably the smartest and also very helpful. But more than that, he is both nice but still nudges you towards the right path- which is incredible in my opinion.