About a month ago, I left my job as a data scientist at Remind to join Eastlink Capital. Now, instead of walking 30 minutes to work, I'm taking the Caltrain down the Peninsula to the familiar Palo Alto where I went to school and walking a few minutes from the station across a small creek separating Palo Alto and Menlo Park. Aside from the commute, this job was a huge change. I went from an engineer to business analyst. I went from working at an 80-person startup in your typical warehouse-turned venture capital subsidized cash burning machine to a small fund finding the next billion dollar company. This transition helped me to solidify my perspective on work, which started to take shape when I first joined Remind in 2015.
Remind was an education startup based in San Francisco. I spent most of my time with the growth team (a Silicon Valley jargon for a team that's a mix between product and marketing) and focused generating insights through experimentation that helped the team decide what to build. At the time, the company was about 50 people, and it felt like a teenager's first year in college, with tons of problems to solve and not enough time to do work on everything. In this environment, I quickly had to learn new technical skills applied to new and complex challenges across all parts of the company (e.g. forecasting support tickets, analyzing new user onboarding). I quickly realized that I love being a generalist (vs. a specialist) and that I never would want to learn something to become "expert" in a single area.
Sometime towards the end of 2016 Remind started to feel like a much bigger company, with multiple product areas and a much larger support infrastructure. It was also around this time that my pace of learning slowed to crawl, and the discussion in the company shift from thinking about the problem to "how" and "who" (e.g. politics) and consequently the value changed from generalists to specialists. My output was highly valued, and I was content with Remind, yet I was unhappy. As a highly rational person, I turned to thinking about a set of criteria to evaluate this dissonance, and eventually came up a framework about work itself. I took these ideas from investing (big fan of Warren Buffet) and talking to mentors and my girlfriend.
My philosophy on work
(1) Apply effort to increase the rate of learning, which would compound to a huge dividend over my lifetime. It is an asset which maintains a high level of return on investment year after year. Not learning is like holding cash, which loses value over time due to inflation.
(2) Being uncomfortable with what I am doing. If I am comfortable, then I am probably not taking any risk. No risk = no reward.
(3) Being a generalist over a specialist. Instead of specializing, I prefer a being a generalist with a broad set of skills and knowledge.
I looked at Remind under these lenses and decided it was time to leave.
I landed at a venture capital firm because it more closely aligned with my work philosophy. I am not sure yet if I could be a great investor, but that's part of what make this job so compelling. I'm learning a different set of skills to analyze industries and potential investments, and I find the changing landscape of technology absolute fascinating. Nevertheless, this job is still a test. If there is one thing I took away from Remind, that's to constantly experiment and double down when the right opportunity comes along.