I’ve been living in San Francisco for three and half years now. Over this time period, a lot had happened, but I had not shared my experiences with many people. This is my attempt to selfishly document as much as I can remember, both the interesting and the not-so-interesting stories. It’ll likely take many posts over many months, possibly years.
In April 2015, I saw Justin Kan tweet about his new startup, The Drop. It was a house music discovery site, kind of like /r/house but with playback on the site. Justin was one of the startup OGs. He’s the Justin behind justin.tv, which eventually became Twitch and sold to Amazon for close to $1B. He was in the first Y Combinator class ever and eventually became one its partners.
I was living in Boston at the time, a year and half in my first software job. There weren’t many opportunities like this, where you could join a successful entrepreneur’s new gig and learn about startup. I jumped at it, and sent him an email.
Over the next week or so, I did a couple of interviews, and eventually came to San Francisco for a one week trial period.
For some reason, I was expecting to work out of an office. But upon my arrival, I realized that this was actually Justin’s home. He lived in a big house with three units. One was essentially an informal co-working space, where his friends and founders he invested in could work and hang out. Startups he incubated would work there as they’re building out MVPs. Once you got some initial traction, you could raise money and move to a real office. People would share the latest apps they built to get feedback and discuss new startup ideas. This was like Erlich Bachman’s house in Silicon Valley.
The Drop was one of those startups. Justin wanted to build a music company so he convinced his college friend Ranidu Lankage to quit Google and start The Drop together. Ranidu would be the CEO and Justin would fund it and be on the board. Ranidu was a DJ and knew many people in the music industry. It was the perfect fit.
Justin built much of The Drop’s MVP. It was functional, but it wasn’t a great product. During that week, I created a couple of new features and refactored a bunch of code. We sat around a dining room table and listened to the newest songs submitted on the site as we worked. It felt like I was working on a side project with friends.
Soon after returning to Boston, I received the full-time offer. It paid $50,000 less than what I was making, in a city with higher cost of living. However, I was ready to risk it all. It had the potential to change my life trajectory. What’s the worst that could happen? I could always move back to Boston. I started saying goodbye to friends and family. I gave my two weeks notice and told my manager that I was taking on this once in a lifetime opportunity.
On July 12, 2015, I moved to San Francisco.