I met the Reddits before we even started Y Combinator. In fact they were one of the reasons we started it.
YC grew out of a talk I gave to the Harvard Computer Society (the undergrad computer club) about how to start a startup. Everyone else in the audience was probably local, but Steve and Alexis came up on the train from the University of Virginia, where they were seniors. Since they'd come so far I agreed to meet them for coffee. They told me about the startup idea we'd later fund them to drop: a way to order fast food on your cellphone.
This was before smartphones. They'd have had to make deals with cell carriers and fast food chains just to get it launched. So it was not going to happen. It still doesn't exist, 19 years later. But I was impressed with their brains and their energy. In fact I was so impressed with them and some of the other people I met at that talk that I decided to start something to fund them. A few days later I told Steve and Alexis that we were starting Y Combinator, and encouraged them to apply.
That first batch we didn't have any way to identify applicants, so we made up nicknames for them. The Reddits were the "Cell food muffins." "Muffin" is a term of endearment Jessica uses for things like small dogs and two year olds. So that gives you some idea what kind of impression Steve and Alexis made in those days. They had the look of slightly ruffled surprise that baby birds have.
Their idea was bad though. And since we thought then that we were funding ideas rather than founders, we rejected them. But we felt bad about it. Jessica was sad that we'd rejected the muffins. And it seemed wrong to me to turn down the people we'd been inspired to start YC to fund.
I don't think the startup sense of the word "pivot" had been invented yet, but we wanted to fund Steve and Alexis, so if their idea was bad, they'd have to work on something else. And I knew what else. In those days there was a site called Delicious where you could save links. It had a page called del.icio.us/popular that listed the most-saved links, and people were using this page as a de facto Reddit. I knew because a lot of the traffic to my site was coming from it. There needed to be something like del.icio.us/popular, but designed for sharing links instead of being a byproduct of saving them.
So I called Steve and Alexis and said that we liked them, just not their idea, so we'd fund them if they'd work on something else. They were on the train home to Virginia at that point. They got off at the next station and got on the next train north, and by the end of the day were committed to working on what's now called Reddit.
They would have liked to call it Snoo, as in "What snoo?" But snoo.com was too expensive, so they settled for calling the mascot Snoo and picked a name for the site that wasn't registered. Early on Reddit was just a provisional name, or so they told me at least, but it's probably too late to change it now.
As with all the really great startups, there's an uncannily close match between the company and the founders. Steve in particular. Reddit has a certain personality -- curious, skeptical, ready to be amused -- and that personality is Steve's.
Steve will roll his eyes at this, but he's an intellectual; he's interested in ideas for their own sake. That was how he came to be in that audience in Cambridge in the first place. He knew me because he was interested in a programming language I've written about called Lisp, and Lisp is one of those languages few people learn except out of intellectual curiosity. Steve's kind of vacuum-cleaner curiosity is exactly what you want when you're starting a site that's a list of links to literally anything interesting.
Steve was not a big fan of authority, so he also liked the idea of a site without editors. In those days the top forum for programmers was a site called Slashdot. It was a lot like Reddit, except the stories on the frontpage were chosen by human moderators. And though they did a good job, that one small difference turned out to be a big difference. Being driven by user submissions meant Reddit was fresher than Slashdot. News there was newer, and users will always go where the newest news is.
I pushed the Reddits to launch fast. A version one didn't need to be more than a couple hundred lines of code. How could that take more than a week or two to build? And they did launch comparatively fast, about three weeks into the first YC batch. The first users were Steve, Alexis, me, and some of their YC batchmates and college friends. It turns out you don't need that many users to collect a decent list of interesting links, especially if you have multiple accounts per user.
Reddit got two more people from their YC batch: Chris Slowe and Aaron Swartz, and they too were unusually smart. Chris was just finishing his PhD in physics at Harvard. Aaron was younger, a college freshman, and even more anti-authority than Steve. It's not exaggerating to describe him as a martyr for what authority later did to him.
Slowly but inexorably Reddit's traffic grew. At first the numbers were so small they were hard to distinguish from background noise. But within a few weeks it was clear that there was a core of real users returning regularly to the site. And although all kinds of things have happened to Reddit the company in the years since, Reddit the site never looked back.
Reddit the site (and now app) is such a fundamentally useful thing that it's almost unkillable. Which is why, despite a long stretch after Steve left when the management strategy ranged from benign neglect to spectacular blunders, traffic just kept growing. You can't do that with most companies. Most companies you take your eye off the ball for six months and you're in deep trouble. But Reddit was special, and when Steve came back in 2015, I knew the world was in for a surprise.
People thought they had Reddit's number: one of the players in Silicon Valley, but not one of the big ones. But those who knew what had been going on behind the scenes knew there was more to the story than this. If Reddit could grow to the size it had with management that was harmless at best, what could it do if Steve came back? We now know the answer to that question. Or at least a lower bound on the answer. Steve is not out of ideas yet.