I first met Sam Altman on September 24, 2015 at Y Combinator's Mountain View office. I got lucky and was granted an office visit with him before their next round of formal interviews for YC. I arrived (very) early to their Mountain View office and patiently waited for my meeting.
"What are you working on?"
As soon as Sam sat down, I vividly recall him getting right to the point: "What are you working on?" As luck would have it, Sam's mom is a doctor and he immediately understood the pain we're solving in the market. He'd been her IT guy growing up.
He then dropped a bomb on me and hypothesized we could build a company of ten figure significance. If any other person had told me that, I wouldn't have believed it. But here's Sam and YC with 10 unicorns under their belt. "Hell, maybe he's right?"
SEE RELATED: Sam Altman’s Manifest Destiny [The New Yorker]
The meeting ended with Sam asking us to apply to YC. My mind screamed, "of course we're going to apply!" but I kept my cool and said something like, "sure, we'll definitely apply."
Fall Down Six Times, Stand Up Seven
We got to the final interview day for YC and although I gave it my best in the interrogation/interview room, we didn't get in. I felt terrible. I let the team down. But you know what, tomorrow is another day. Get up, dress up, show up. We applied again to their next batch and didn't get accepted to that one either. Other accelerators turned us down too: Launch (once), Alchemist (once), StartX (thrice) and 500 Startups (once). On our second time applying to 500, we got in. And man, we gave it 100 during our time there. We love 500 Startups for giving us the opportunity.
"How can I help you?"
Earlier this month, Sam emailed me from out of the blue with an empty message body and a subject line that read: "how are things going?" Wow, what a pleasant surprise in my Inbox. A few emails later, we arranged a meeting for yesterday afternoon. I arrived a few minutes early at the YC SF office and waited for my meeting. Sam again got to the point quickly: "How can I help you?" I happily brought out my cover letter with bullet points of traction and our fundraising objectives. I also brought out an MRR Linearity Chart and as I was about to dive into our 2017 Sales Plan, he interrupted and said, "The most value I can give is to help you fundraise." Nuff said! In all, it was the best 12-minute meeting I've had yet. Mahalo Sam!
About Y Combinator
Y Combinator is an American seed accelerator, started in March 2005. Fast Company has called YC "the world's most powerful start-up incubator" while Fortune has called Y Combinator "a spawning ground for emerging tech giants."