"What makes you a top digital influencer?"
I've read through thousands of applications, but at the end of the day there's really only one good answer: Google me.
What follows is an explanation of how I got into Y Combinator by adopting this posture toward life, and how I've earned the dubious honor of being the only non-technical single founder that Y Combinator has ever funded. As a free bonus, I'll throw in a couple YC interview tips that I haven't seen posted anywhere else on the web.
tl;dr What makes me so unique and special? Nothing. I just shipped.
I started this blog the day after I got rejected from Y Combinator.
Why? Because of a story my college rowing coach told me about his own experience as an undergrad. Even though he had been one of the fastest rowers the fall of his freshman year, he wasn't put in the boat for the big race of the season. Apparently they wrote everyone's names on popsicle sticks and moved them around as the way of setting lineups, and when his popsicle stick fell under the table no one had noticed. By the time anyone found out it was too late, and he simply didn't get to race for that season.
Then and there he made a vow that no one would ever lose his popsicle stick again, and he doubled down on his training until he practically was the boat. This was my inspiration. I would start the greatest blog ever, and Paul Graham would never lose my popsicle stick again.
So I started my blog, and within mere weeks my writing was regularly being featured on the front page of HN, Reddit, Delicious, StumbleUpon, etc. I even made the front page of Digg, which even then was virtually impossible.
When I reapplied the first time, I did so with someone who was widely recognized as one of the smartest technical folks on HN. We made the interview round, but then got rejected again.
So I went back to school, finished my degree, and largely forgot about YC proper. After college I participated in Seth Godin's alternative MBA, an experience that practically deserves its own book. As part of this program we each had to start our own business, which is where Swagapalooza came from. This was never meant to be a real business, it was basically something I started because the domain name was available and I thought it would be funny.
The first event was in September 2009, and essentially everything that could have possibly gone wrong did. We even forgot a name tag for Peter Shankman, our keynote speaker.
Imagine my surprise when then next day I discovered a couple dozen blog posts and articles about how much people loved the event. So I quickly came up with a plan to scale this into a real business, and reapplied one last time.
Now you'd probably expect that if Y Combinator accepted me as a non-technical single founder, it must be because I have some sort of extraordinary sales ability, and that I completely killed it during the interview. Nothing could be further from the truth.
Halfway through the interview I discovered that no one actually understood what I was trying to make. I started getting more and more nervous, until eventually I basically just lost my ability to talk and was curled up in a little ball in the interview chair. The ten minutes finished and everyone in the room still had very little understanding of what I was working on, let alone why it was going to be big. They told me the interview was over and I asked if I could play a short video clip of a blogger talking about how much she loved the event. They said no. I turned up the volume and started playing it anyway as I slowly backed away. Jessica looked disappointed.
Later that I night I got a phone call from pg saying, "You probably weren't expecting this call, but..." and the rest is history.
The coach of the Yale rowing team has a saying about high school recruiting: "7:20 2,000m time, 720 SATs. 6:20 2,000m time, 620 SATs."
So far as I can tell, that's essentially what happened here. If you have a track record of shipping, nothing else matters. You can (apparently) flub the interview, have all sorts of stuff go wrong, and still be just fine. If I hadn't had 25+ blog posts and testimonials from people talking about how much they loved the event then I would have been dead in the water, even if I had the best cofounder in the world.
That said, as poorly as my interview went, there are still a few tips I want to share:
- When you get into the interview room, start by explaining what it is you do even if they don't ask you. The YC partners interview so many people that by the time they get to you, everything is a blur. However, perhaps because it's somewhat socially awkward, they're not always the best at admitting this. Even if one of them starts by asking a specific question, it's best to start by explaining the whole idea from scratch. Just pretend it's like The Bourne Identity, and assume that they have zero memory of everything on the application.
- Have a mindmap with the answers to all the questions they might ask. Having a word document with notes is no good, because as soon as you start scrolling through they'll get impatient and just ask another question. Whereas with a good mindmap you can answer every conceivable question in real time, even if you're drawing a complete blank. Here is an example of the mindmap I made for my interview, with the caveat that I've removed most of the answers: alexkrupp.com/yc.html. It's obviously much better if you're able to completely nail every answer without having to glance down at your computer, but it's also really easy to forget two of the four ways you're going to get new users when you're under pressure.
- Basically answer these three questions, regardless of whether or not you get asked them: What does your startup do? How does it scale? How do you get new users? The second question is especially important, because it's what they're looking for in every startup they fund. By the end of the ten minutes they had no idea what I was making, but they sure as hell knew how it was going to scale.