6 lessons from Y-Combinator, 10 years later

That was our pitch for Kimono Labs at YC demo day in Winter 2014.

With demo day coming up this weekend, I wanted to reflect on what I learned from YC, 10 years on and another company in.

1. The 7 minute espresso rule. Our first meeting with Sam Altman lasted just seven minutes. The batch hadn’t even officially started yet and my cofounder Ryan and I drove down from Mountain View to the tiny SF YC outpost to meet him. Sam was making an espresso when we walked in. He opened with – “have you launched”? We said no, too many bugs. Our product, kimono, made it easy to just point and click to build a web scraper. Our promise was to get you an API in 60 seconds, without writing a single line of code. But, the web is vast, and websites are very different. We needed it to work on a large enough spectrum of sites so that our first users would have a good experience. It worked on just a handful of sites at the time. Sam pushed us to make sure we were launched in less than 2 weeks. We debated, highlighting the complexity of the bugs and the limits of underlying headless browsing technology. The espresso finished brewing, he picked it up, looked at us and said, “well, you better get going then and fix those bugs”. We left, launched within those next two weeks and learned one of the most important lessons that day - speed matters. Ship something you’re embarrassed by.

2. There are no experts. Ryan and I were not prepared for the rapid influx of user on launch day. We did 88 user interviews to validate our product idea, and everyone basically said they wouldn’t use it. We thought they were wrong and built it anyway. It got tons of traffic on day 1. We didn’t sleep in the 48 hours following because our servers and database kept crashing. We hadn’t indexed it properly. We realized we weren’t the experts and needed to hire one. We went over to Michael Seibel’s apartment for advice. Michael smiled and told us about the early days at SocialCam, that eventually became Twitch – experts thought the streaming video problem was too hard to be possible. The answer wasn’t hiring an expert, but hiring someone young, capable and naïve enough to give it an earnest try. So we opted to just figure it out ourselves.

3. Messages in Pizza Boxes. Startups win through incredible customer service, then through product, not the other way around. Seibel told us how SocialCam’s streaming infrastructure went down while a key teammate was unreachable off-grid in a Tahoe cabin for the weekend. Normal people would have waited until Monday. Not Michael. He called a local pizza delivery place and asked the delivery person to send a large pizza with an urgent message in the box to the cabin. Their infrastructure was back up in hours.

4. The Twinkle can matter more than the TAM. Ambition matters just as much as practicality. Before demo day, we were struggling with the end note of our pitch. We knew the value of our product, and had a fanatical and fast-growing user base, but the market size we calculated either seemed so ridiculously big that it was not plausible, or so narrow that it was equally silly. PG and Geoff Ralston sat with us and showed us that if we can really pull it off at scale, it would be bigger than Google. So, we could skip the market size, if we really believed it. PG suggested not talking about market size, but just making sure people could see the twinkle in our eyes when we talked about what you might be able to do with a structured copy of the internet that’s larger than Google’s.

5. You’re always at the Origin. Our demo day was successful beyond our wildest beliefs. Afterwards, Geoff Ralston drew a chart for us on a whiteboard. It was a hockey stick. He asked us where we thought we were. It was a rhetorical question. He said we were at the origin, and that the most important thing is to remember that. Sam Altman doubled down. When he invested in Kimono, he gave us a Zimbabwean Trillion dollar note (the result of extreme hyperinflation in Zimbabwe), as a cautionary reminder that the fundraising and valuation mean nothing. We have channeled this into our culture at Arena with our ritual around neon shoelaces and a pair of neon track spikes hanging on the wall to remind us that we’re at the Olympic starting line, but we don’t have any medals yet. You can read more about our ritual here.

6. High bandwidth discussions with users don’t happen over email. The Collison brothers, who founded Stripe, took user engagement to the next level – so much so that “Collison installation” is part of YC lore. John Collison told us that talking to users was essential because email and chat conversations were not “high bandwidth” enough. He emphasized the importance of what you can learn being with users in person or talking to them over Skype (remember, this was early 2014!). We took this to heart, and spoke to hundreds of users at Kimono regularly over Skype. One power user, Alex Chung, who I met this way, has become a close friend and even attended my wedding in India last year. At Arena, we now go a step further and regularly fly to our users. We over-invest to a degree that is almost crazy in order to be more than a supplier — a true partner to our early customers. YC taught us it’s the only way to understand their problems on the ground and really make sure our products work for them.

   

   Our very official kimono press photos, taken by Ryan’s Mom :)

YC taught us to outsource very little. Own the problem. Own the outcome. And if you do, you get to be stupidly ambitious.

If you’re curious about Kimono (which we later sold to Palantir), here was our launch demo. No-code web scraping before “no code” was even a term: