I love the early days: small teams with unique and clear insight about the future. Often there are raw edges, and much is not yet figured out. Partnering closely with these early teams to help realize their long term ambitions is the great pleasure of our business.
One of my good friends from MIT dropped out to join Dropbox when the team was just a handful of people. At the time, I had little awareness of Dropbox, Y Combinator or startups in general, much less any appreciation for why one would drop out of school. That was kind of a wakeup call.
My interests…everything, really. I’m fascinated by new platforms: the internet, mobile devices, and whatever’s next.
I chose to go to MIT to study math, but I also spent as much time as possible in the computer science and economics departments. In retrospect, I would have shifted the weighting more toward computer science, but training in math has turned out to be a surprisingly helpful tool for better thinking.
Junior year I started hacking on projects with a couple of classmates. Eventually our efforts evolved into a company called Hotspots - funded by Y Combinator and other angels - where our focus was on building analytics tools for streaming data.
Hotspots was acquired by Twitter in 2012, and we spent the next couple of years building analytics for Twitter ads. It was a fascinating experience to see the company scale from about a hundred million to billions in revenue and an IPO.
In general, I’m highly skeptical of what’s popular. It’s an automatic response that is not always productive, but overall I’ve found it to be helpful as the seed for independent thought.