Two or three months after arriving in Sunnyvale, our startup accelerator program ended and it was time to move on. There was no way I was going to continue living in the suburban town of Sunnyvale, so I started looking for a place in San Francisco. As someone who owned (still owns) a pair of round frame Warby Parker eyeglasses, I had a keen interest in the Mission District. Within five minutes of walking around on a Saturday afternoon, I knew for sure that this was where I wanted to live.
As I soon found out, renting an apartment in SF is no joke. If you're not 100% prepared and ready to sign on the spot, then you lose. In my case, I lost to a 19 year-old wearing an oversized backpack and an Apple employee ID/keycard. It took me one day to understand the rental game, another day to convince my roommates-to-be that they needed to get their shit together and show up, and another day or two sign on an apartment. Our new apartment would go on to become a place of legendary good times as well as legendary drama, and to be known simply as 3027.
In the early days, we joked that our living situation was like the TV show, New Girl — and it kind of was like a sitcom. We were four close friends living in a small, three-bedroom apartment. Two of us (Fraser and I) were business partners, starting a startup from the kitchen table, and the other two (Isaac and Melissa) were recently engaged. Each of us met and became friends in Vancouver, and by sheer fate, we all happened to end up in San Francisco at the same time.
Fraser and I were flying around the country every other week to sales meetings and conferences. Isaac was getting ready to start his MBA. And Melissa was trying to adjust to her new setup in San Francisco. It was a beautiful time in life — at least it was for me.
Among many other things, we discovered the joy of Philz Coffee in the morning, sandwiches at Salumeria for lunch, and Dolores Park on the weekends. We went surfing in Santa Cruz, hiking in Big Sur, rock climbing in Yosemite, skiing in Tahoe, and biking across the Golden Gate Bridge. When we weren't out of town trying to drum up sales, we took investor and partner meetings all over Silicon Valley, at Google, Twitter, Facebook, and a whole bunch of other startups and VCs.
By early 2013 we had found our first paying customer — and it was a big one. Our ideas about who our customers was, how they would use our product, and how much it was worth were being validated. It felt like we had figured out the all important "product-market fit" and we were ready to hit it hard.
More and more, San Francisco felt like an unnatural place for me to be, given that many of our prospective customers were concentrated in New York. Flying back and forth was expensive and annoying, but it wasn't just about geography — it was about culture. San Francisco is the land of tech startups, and New York is the center of fashion, media, and retail. If you're selling to people in that space — and we were — then you need to have a presence there, and you need to look and act the part. At least that was our rationale at the time.