Apart from the culture shock, what was college like?
The school where I went wasn’t friendly to failure. It was a meat grinder. When you walked through campus around finals week you saw kids sitting on the ground crying.
Still, it’s the kind of place where you make connections that end up mattering a lot later. You meet people who will go on to start companies in Silicon Valley, or who will become higher-ups at bigger firms. It’s also the kind of place where recruiters track you from freshman year, have dinner with you at department-sponsored events—that sort of thing.
That industry interest made me feel special. And when I became a teaching assistant for a computer science course, that interest intensified. I had to do a work-study as part of my financial aid, and it was either serving food in the cafeteria or teaching computer science. But teaching paid well—fifteen dollars an hour, which blew my mind, since my high school job had paid four dollars an hour plus tips.
Plus the job was super fun, and the industry attention felt great. Big firms would come in and lavish the teaching assistants with gifts—embarrassing gifts. Sometimes we would go buy cheap tricycles and ride them down a steep hill and play a sort of human Mario Kart. Microsoft found out about it and bought us the highest-quality tricycles available. I think it’s actually gotten worse since I’ve left. These days companies send stretch Hummer limos to pick kids up for fancy dinners.So you must’ve been pretty well set up for a job in tech by the time you graduated.
After I graduated I had a few options of places to work. I chose an older, more established company. That ended up being one of the worst decisions I’ve ever made in my life. I spent two years there while my friends were jumping on rocket ships. Then I decided to start a startup with somebody I knew from school.
My cofounder and I had been talking for several months about doing our own thing. In college, everybody was expected to go start a startup—that expectation had been drilled pretty deep into us. We lived in a big house with a bunch of friends, and we turned an extra room into an office. We had a really nice routine. We worked there every day, and tried to prototype things very quickly.
This was around 2009, when mobile apps were taking off. It was the era of “SoLoMo”—“social local mobile.” The iPhone had changed everything: there had been programming platforms for phones before, but they were garbage. Everyone wanted to build something for the App Store. The tech giants were way behind the curve, however—the Facebook mobile app was horrible, for example. It seemed possible that the bigger players just weren’t going to make it on mobile, and that created opportunities for startups like us.
So we tried to build a bunch of different apps. None of them found a huge amount of success. But the last one we tried, a social app for making plans with friends, did well enough to get some attention from TechCrunch and other places in the tech press.
It was fun, but scary. Because we always knew that if one of the tech giants got their shit together, they could eat our lunch if they wanted to. I remember waking up one day and seeing a new product announcement from Facebook that I was convinced would put us out of business. I ran to my cofounder’s room, freaking out. It turned out we were fine. Still, I had that feeling of “Holy shit, we’re fucked” a lot. We lived in constant fear of getting scooped.But you didn’t.
Not exactly. But after a year, we were still living off our savings. It was clear that we either needed to get funding, get a job, or get acquired.
Around this time, we went to an up-and-coming company to ask them whether they would give us access to their private API.1 They said, essentially, “No way. You’re a tiny company that doesn’t matter.” But they also said they’d be interested in acquiring us. We were very surprised to hear that. We didn’t even really know what it meant. But we decided to pursue it.
What they were offering is what Silicon Valley calls a “talent acquisition.” They wanted to buy the company, but they weren’t going to take our technology. They weren’t going to take our code. They just wanted to get the two of us working for them. They put me and my cofounder through an interview process, and it was the same standard interview process I’d already been through before. But at the end of it, they made an offer with a slightly different format. It was clear that we were talking to people who worked in their M&A [mergers and acquisitions] department rather than in recruiting. Those people have the authority to write bigger checks, and they’re supposed to be thinking about what the company is going to need a little further down the line.
We were very green, so we didn’t know what a good offer looked like. But we did know that we should go get at least one competing offer, to see what our options were. So, using our network of contacts from college, we reached out to somebody who had the ear of a few VPs at a bigger company that made similar acquisition offers. We said, “Hey, we have this offer from one of your competitors. They’re moving fast. Can we start a conversation with you?”
Recruiters famously don’t make the process very fast for people. You can do an interview and not hear back for a month, for instance. It’s frustrating for most people
