The first day we all talked about our startups was called “prototype day” and presented as “a 2 minute way to introduce yourselves to your batch mates, talk a little about your startups, and tell each other what you could help with. Don’t stress about it at all, guys!” I made 4 slides with 5 words total, went up there and told our batch mates they should use our product if they had an app, and that although I used to be in HFT they shouldn’t ask me for investment advice.
When I sat down, PG said, “I’m going to say it again- don’t talk too fast.”
Geoff Ralston added, “And don’t drift off without a conclusion.”
After everyone was done, PG said, “You guys should notice that you guys, like investors, favor the serious startups that talk about revenue.”
I was like, “I thought this was a way to introduce ourselves, not a mock pitch towards investors! Why did everyone else clearly spend a ton of time on their presentations and assume their target audience wasn’t their fellow batch mates! Don’t they have companies to run!”
At the bar later, my drunk batch mate came up and said, “Hey, you did good, you rolled with the punches.” At that moment, I decided to win YC.
“What does ‘winning YC’ mean?” Jeremy asked.
“We’ll figure it out!”
A few days later, this resolution disappeared into the swamp of my mind along with everything that wasn’t frantically fighting to surface. There was so much shit happening that demo day nauseously oscillated between seeming ages away and then sickeningly almost upon us. Part of me had believed that if we got into YCombinator, all of our problems would be solved. Spoiler: this didn’t happen. While there were office hours where in a moment of intense optimism one might muse, “Should we be charging each user $400 or do more marketing and charge each one $10?” conversations with users that revealed they had no idea what 90% of your product did would quickly smack us down into realizing we didn’t have the luxury to discuss these types of problems.
Pre-YC, I’d wondered, “I’ve read pg’s essays. I can emulate him somewhat in my brain. Do I really need to give him 7% of my company so I can talk w him for 20 minutes about my company, which I’ve thought about a lot more than he has?” Yes, yes I did. He really is that good. PG actually loves you and wants your startup to do well and is undyingly optimistic that it can succeed despite whatever dumb thing you’re doing. He cares about founders and developers and that’s the reason he’s doing it. Every time I’ve posted to hacker news, he’s emailed accusing me of gaming his algorithms: that’s passion. He’s a fountain of secret data no one else knows and is a genius when it comes to knowing what different groups of people like VC’s or users want. After YC ended, I was talking with pg, “How did you know x would happen?” and he was like, “Duh, I’ve seen more than 520 startups.”
Some people you talk with about your startup and it’s obvious they don’t care about you and aren’t really thinking and are just saying whatever knee-jerk thing the first google hit would say. The YC partners aren’t like that. They are excited / terrified for you and think about your situation. Each partner has their thing they’re amazing at. They’ll walk through your product with you and tell you where it sucks. Our main guy Geoff Ralston told me what to say to different leads. Mike Seibel and Ammon told me about their AB testing dramas. Sam Altman gave me his number and coached me through meetings. Kevin Hale user tested Apptimize and told us exactly what to fix. I still have screenshots of our first iteration that we were so proud of and now find quaint. It’s amazing to have some of the best and most well connected people in the world look at your disgusting fetus of a product and tell you their real opinion.
This summer, my brain was remolded into Apptimize CEO-shape. I started dreaming about Apptimize. Apptimize became the reason I was cutting my nails and working out. My whole life I’d viewed running as extremely boring but now I run 7 or 8 miles every time because it’s an incredibly efficient form of exercise for Apptimize. Apptimize lets me do anything, no matter how boring or painful. Every piece of food I eat is an energy source directed towards Apptimize productivity. Everything I do is because I did linear algebra in my brain and decided the vectors were sufficiently aligned in an Apptimize-beneficial direction compared to the other choices to merit incorporating. Every product, app, technology I see exists in the context of Apptimize and my first reaction is generally how much better it’s going to be once we get our Apptimize mitts on it.
A week before demo day, we had the office hours with Paul Graham where you talk about your demo day outline and he yells at you while wiggling his toes. “Why are you going on and on about product features? You’re certain to cause vc’s to immediately start checking their email.” Despite this help, our rehearsal day speech was insanely bad. PG said, “I only remember 1 factoid from this demo,” before immediately proving he didn’t even remember it accurately (although Jessica did).
I have better UX now- I guess that’s another thing I learned at YC. Demo day was about having UX optimized for a particular kind of user that you don’t normally engage with- a herd of top venture capitalists. PG is a genius at demo day UX design. Every normal person is extremely bad at it (How could any normal person possibly be good at it?). Our presentations were sooo bad before PG got his hands on them. For example, I assumed VC’s wanted to know what our product did. Our product is complicated and technical with numerous benefits and applications which features I spent minutes giving examples of. PG put a stop to that and patiently listened to 10 iterations of our demo until it was pounded into something memorable. We learned to emulate PG better, which was good because we kept changing stuff until the last minute. On demo day, PG (and everyone) was seeing 20% of our presentation for the first time. Luckily, it worked out! He said our demos were “significantly improved even from yesterday.” More than 100 kick-ass investors came up to me and asked about investing, including MC Hammer who also followed me on twitter, meaning now a significant percent of my followers are celebrities named MC Hammer.
We almost didn’t apply to YCombinator because 7% sounded like way too much of my company to give away to a bunch of people whose blogs I already read. I felt I could get the benefit of the advice in other, cheaper ways than giving them a chunk of my company. Like, I already knew a lot of YCombinator alums from MIT so I was already quasi part of the network anyway, right? Wrong! The network is amazing. When we were going through a confusing situation, I emailed a few companies who’d gone through something similar asking for a quick phone call, and it didn’t matter that they were running companies worth hundreds of millions or billions- they called to give me the real story behind what went down.
A month after YCombinator ended, I missed everyone so much I ordered the hoodie and iPhone case and other schwag that I generally eschew. The bonds coalesce after the program ends- we all felt like we didn’t get to know each other well enough during YCombinator because there was so much going on, but now we chat online and meet up in Palo Alto. I feel so inspired every time I talk with my batch mates. If you have an entrepreneurial bone in your body, apply here. YCombinator is awesome and easily worth it.
