The recent spate of postmortem posts by prospective Y Combinator applicants has got me thinking of my interview experience. In May 2005, my lifelong friend Emmett Shear and I were seniors at Yale. We were working on a website during school called Kiko.com (a domain we purchased for $250, a big investment for us at the time). Our plan for Kiko was to build the world's first AJAX calendar web application, although at the time many of those terms hadn't been coined yet and we just described it as a web calendar with an Outlook style interface. We had big plans for the site: millions of users, possible partnerships with big web mail clients, and a plan to monetize through an advertising system for events (we'd see where you weren't planning anything on your calendar and show you an ad for a concert or movie). I remember that we'd have pipe dream discussions about possibly selling the site to Yahoo, Microsoft or Google eventually, even though we had no idea how that happened in practice.