I was living in my girlfriend’s dorm at the time on Stanford’s campus. At this point, I had been crashing at the school on and off by living under her bunk bed for 7 months. Free food, free gym, free bed, plus her…not sure why I was leaving all that to repeatedly go all the way back to New York to stay in my co-founders parents house with him. Her roommate was an absolute saint who never seemed bothered by me. I had gotten into the habit of sleeping until 2 everyday and missing all the famous people who came to campus for various reasons. Over the last month, I had already missed both Mark Zuckerberg and Elizabeth Holmes speaking.
This time, my girlfriend insisted I go to the YC Startup school class. I had already been working on Shotput for about a year. Our company was basically handling the logistics for kickstarters and startup who did not have the time or energy to deal with warehouses and shipping. I doubted going to this class would help us get in but she insisted.
One day, I woke up at 2 as usual and was halfway to the gym when my girlfriend said we should check out this Y Combinator class called CS183b.
Fineee
We both get to the class a bit late but enough to sit through the lecture by Jawbone. It was a talk about hardware and quite boring to be honest. At the time I was running Shotput.com and we were trying to make an API for logistics to be used by product companies. It sounded like a good lecture because Jawbone was a fitness related product company, although their volumes were probably way too high to even consider us.
But man was it boring. I was on my computer the whole time just trying not to fall asleep.
Finally it ends and I decide I’ll talk to the Jawbone guys and pitch my company. Sure I hadn’t showered in a day or two, but I was wearing a Stanford hoodie so maybe that helped.
So everyone leaves and a few stragglers stick around to talk to the founder making it hard for me to pitch to him. Meanwhile, my girlfriend points out Sam Altman standing around awkwardly in the corner of the room with no one talking to him.
“Talk to Sam” She said.
Up until that month, Paul Graham was head of Y Combinator. I barely had even heard of Sam except as that guy who once wore two popped polo shirts on stage with Steve Jobs. But now he was just named new head of Y Combinator. All the more crazy as today he is swarmed by startup and tech nerds wherever he steps. My girlfriend insisted I go talk to him and I said it didn’t matter. I insisted that unless Paul Graham himself was in the room, I doubt anything I say will help.
“The Jawbone guy has the ability to offer us business, he only has the ability to offer us potential business!” I replied. Oh how wrong I was.
The Jawbone guy was fast leaving and still crowded by some people so she convinced me to give it a shot with Sam. I make some small talk with him. I forget to mention my name, but he’s a friendly guy and super-concise in every interaction. Must be from all the people he talks to on a daily basis. He’s about to leave as well so I quickly say I have one more question:
“Y Combinator has been investing into more and more hardware companies like Jawbone, do they go to anyone to figure out their distribution and fulfillment? Who helps them?” I ask.
“Well…its sort of an informal network…really past alumni just help out the new ones.” He said.
“hmm…that would make a really great start-up. Yeah.” Sam nods and thinks about what he just said.
I jump in. “Actually, we’ve been working on this for over a year! Could we talk to some of the hardware companies in Y Combinator? We want to understand what problems they have.”
Boom.
“Send me an email.” Sam said.
“Oh okay.” Exchange over.
We have a short exchange online. He sends out an email to ALL hardware companies in YC. We get two interested companies within an hour. I let him know and say we will definitely apply to the next Y Combinator batch. He writes back “Why don’t we talk about this upcoming winter one?” We are already over a month late for that application, but hey we aren’t going to refuse.
Inbound leads and a super late interview, this Sam guy sounds pretty darn nice, right? In a strange twist of fate, my cofounder allegedly had the complete opposite with Sam 7 years prior. He actually got a Y Combinator interview back in 2009 with a completely different company and co-founder. I wasn’t there but here’s my understanding from multiple retellings.
Y Combinator was still very early and not famous at all. My cofounder was a fresh-faced 19-year-old with no idea of what to expect from the interview. Naturally, the email sent out for the interview said the dress code was “casual.” My cofounder, interpreting that as business casual, naturally decided to wear a suit. Anyone reading this now probably sees how funny this is.
He gets there and all his heroes end up interviewing him because there aren’t that many partners at the time: Paul Graham, etc. But most importantly, Sam is there. He starts to make fun of Praful’s suit. Sam says, “You look like an MBA.” They end up not funding his idea.
Now I don’t know what it would be like if people I looked up to started making fun of me for what I was wearing, but of the 6 years I have known my cofounder, he hasn’t worn a suit since.
Anyway, the batch is about to start in 5 days. We still have no response if we got the interview and we live in New York, thousands of miles away from San Francisco. We are very skeptical this is going to happen.
With only a few days left, we check our email. They want to interview us 3 days before the batch is supposed to start. They’ll fly us out and give us just enough money to come over. 10 minutes go well and we get access to their funding and resources, not to mention the prestige. Time to start practicing for this interview.