1. You learn how to ask the right questions. Anyone can ask questions. But learning how to ask the right questions — to use questions as a mechanism to uncover the hidden truth in a company’s business model, or the trade-off’s in an engineer’s architecture, that comes with training. VCs spend a huge amount of their time asking questions, and thus learn the craft of asking the right questions. This skill has been enormously valuable to me as I transitioned to Pinterest.
2. You learn how to read people. In my first performance review at Bessemer, people judgment was one of my weaknesses. I’d now say it’s one of my strengths. As a VC, you’re constantly meeting founders and building your pattern recognition for reading people. This skillset is particularly useful when you’re in a business or corporate development role, but as with asking the right questions, it’s one of those horizontal skills that will serve you anywhere.
3. You learn how to learn. In VC, you’re constantly ramping up in a new area. Each company you evaluate brings with it its own ecosystem that you need to understand. Similarly, trends in the tech ecosystem turnover so quickly, that if you ever stop adapting and learning, you’ll quickly become a dinosaur and won’t know a Snapchat when you meet one. That drive to constantly learn will help you adapt to new environments and challenges.
There’s a flipside to these three though:
1. In startups, you’ve got to answer the questions. One thing I learned early on at Pinterest is that my muscle for asking questions was a lot stronger than my muscle for answering them. As with asking questions, there’s an art to answering questions well. It’s been good to exercise this skill.
2. You don’t learn how to read an organization. VC firms tend to be smaller partnerships. Although Bessemer was about 45 people when I left, I was never in an office with more than ten people. As Pinterest has grown from 30-odd people when I joined to more than 200, I’ve had to learn how to navigate a company. People who have come from larger companies definitely have a leg up in this regard.
3. You’re not specialized. VCs rarely specialize. Sure – I knew the e-commerce ecosystem cold, met with countless consumer companies, and quite a few adtech companies, but that doesn’t compare to spending several years working at Google. But you’ve got to start somewhere…