Certain questions, I’ve found, are in the air at certain times: like celebrity deaths, friends asking the same thing tend to cluster. During my first few weeks of college, it seemed almost everyone I met near-immediately tried to establish whether or not I was still a virgin; in the winter of 2013, people I hadn’t talked to in years started popping back into my life to ask me about living in Detroit. More recently — perhaps because they’re currently reviewing applications for their next batch — I’ve had a few different people independently ask me what I think the most valuable part of Y Combinator is.
Despite the fact that its partners write with ever-increasing frequency about exactly what goes on there, YC has developed a certain mystique over the past decade; by the time we got accepted to the winter 2016 batch, even my least tech-savvy friends seemed to know what it was. And with last October’s New Yorker profile of Sam Altman, YC found its way into the consciousness of my most elderly Manhattan relatives (just in time for them to be impressed by me at Thanksgiving).
People always want to know what YC is really like, what parts of it really make your company tick. Is it the mentorship? The money? The network? The one secret trick to starting a successful company that the partners whisper into your ear, Illuminati-style? Or is YC really just a branding play at this point, the “(YC)” you get to append to your company’s name worth more than everything else they give you put together?
Those things were all valuable for me, of course — without them, Castle would probably be out of business today, the founders all face-down in a ditch somewhere. But the most important impact YC had on me was something that operated on a more subconscious level.
It’s hard to remember today, now that “startup founder” has become so much a part of my identity that I’m often embarrassed to tell people at parties what I do, but when we first started Castle I was breathtakingly insecure about my ability to start a business without immediately falling on my face.
We were living in Detroit, where you didn’t overhear investor pitches at every coffee shop and every third Tinder profile didn’t have “CEO” as the job title, and other than a brief stint doing mostly design work at another startup, I didn’t have any business experience whatsoever. Not only had I never really learned how to use Excel, but, searching to open it for the first time in years, I literally couldn’t locate the application on my computer. (Turns out it’s officially called “Microsoft Excel,” and it’s listed not with the Es but the Ms.)
It was impossible to avoid the nagging thought that while every other startup was a “real startup,” we were just three idiot kids who didn’t know what the hell we were doing, and who were going to embarrass ourselves. Badly.
And then we got into YC — vaunted, mythical, legendary YC. (On our third try, by the way.) This was supposed to be where the best of the best were. And we got there and sure, a few people in our batch were literal rocket scientists or teenagers who’d built Canada’s first self-driving vehicle, but for the most part, all the people there were just… people. Some of them were smarter than us, some of them were dumber than us, and all of them were going through the same things we were.
We’d been at it for over a year, but it wasn’t until then that it truly sunk in for me that this feeling — being a bunch of kids just figuring it out, certain that you’re not a real startup — was what starting a company is like for everyone. I’ve taken to describing this as my Wizard of Oz moment: it turns out we were a real startup all along, and we just didn’t know it!
Now I look back and the whole thing seems so ridiculous — how could I, a wealthy white man, raised not only to feel like I belong in every room but to feel like I deserve to be that room’s center of attention — have been so debilitatingly insecure about the path I’d chosen?
But I was. And more than the network or the money or the mentorship, helping me get over that was what YC really did for me.