Part 1: The time that YC said no to us (and why you should never give up)
The first time Gauri and I interviewed for Y Combinator (YC), we knew we weren't getting in. Not just because Gauri and I are women (a historically underrepresented group within startup bootcamps), and not just because we were 10-20 years older than everyone else in the waiting room and yet somehow were the only ones who brought along toys.
We knew we weren't getting in because the room was a "No" even before we opened our mouths. The first question for us was, "Can you shut this thing off?" and I think the last was, "Why wouldn't parents just get their kids an iPad?"
We had eight minutes to convince five startup demigods that our idea was scalable, worth 20,000 of their dollars and a few hours of their time. At that, we failed.
We got over it but not quickly because breakups are hard, even if the people who aren't that into you are just people you sat down with at Bill Knapp's for a senior's only speed date.
A few months later, we were achieving all kinds of milestones and gaining lots of traction but running out of runway at a time when investors were getting fed up with underperforming IOT cos. Funding was getting scarcer by the minute, so an advisor of our said, "Why not try YC again?"
This time, it was Gauri and I who couldn't say no fast enough. We could speculate, but neither of us could isolate exactly what we had done wrong the first time around and besides that, we were a full year older.
But to our absolute shock and amazement, somehow we did apply again. Somehow, we got another interview. And this time, we got in.
Part 2: The time that YC said yes to us (and why you should never give up)
I almost didn't make it to the second YC interview. Audry and I left nearly an hour late for the airport, heavy rains slowed us down to 50 mph, and on top of that Googlemaps had taken us on a wild goose chase through a succession of Detroit neighborhoods, quadrupling our travel time. As I so often do, I missed my flight. And since I was sure we weren't getting into YC anyway, I certainly was in no mood to book another. But somehow Audry convinced me to view the trip as an all expenses paid weekend in the San Francisco Bay, minus the 7 minutes in the interview and the $175 flight rescheduling fee.
I don't know why - maybe because we had more partnerships in place, or maybe just because I didn't try so hard this time, but we got in. And once we found that out, it was hard to get my head around moving to California for three months and leaving all of my friends and family behind to run this crazy experiment. Hard isn't even the word. It was panic inducing.
Yet, I knew YC was exactly what we needed--time to dig into the critical parts of our growing business with only the noise of the greatest sounding board for startups established anywhere, ever.
Someone who had been through YC before I did told me he learned more about business in 90 days there than he did in two years earning his MBA at Wharton. The second I left the campus, I felt the same.
The most important lesson learned at YC was the art of the pitch because at the time we were in fundraising mode. I learned to distill what was a fairly complex phenomenon (messaging platform + expandable cloud content in the body of a toy) into a few key points that would stay with investors long after I stepped out of the room.
YC is very big on measurable growth. I am the kind of person who tries to do everything all at once. YC challenged me to focus on only the things that would truly allow us to scale. Before I answer any email, sit down for an ideation session, vet out prospective parterships, I ask myself if what I am about to do makes us scale. If it doesn't, it's back burner. That's harder to do than it seems but it's beyond critical. Once I started doing it, our growth accelerated.
Hearing founders' stories during the weekly talks was the single most inspiring and motivating YC experience for me. One that really resonated was a now super successful startup founder who when asked what the hardest part of their journey was so far, answered "It was year three, when our youthful optimism had waned, but we hadn't made it big yet. The challenge was continuing to push on." Finally I felt like it was okay that in year three, Toymail was finally having it's "aha" moment. It was literally everything I needed to hear to push on.