Breaking out of Venture Capital!
There’s lots of talk about how to break into highly selective career paths like Venture Capital. It’s commonplace to hear analogies comparing the odds of becoming a VC to the odds of being selected for a major league sports team (a very cringeworthy analogy in my opinion). For example, in the entire state of Michigan (where I worked as a VC) there were just 80 people who worked in the industry. These positions are seen as golden tickets to rapid career growth and future wealth. This perception has been further cemented by the new term “Gen Z VCs”, which essentially celebrates people whose only work experience is in VC. Variations of this narrative exist for other selective career paths like management consulting, investment banking and product management. This explains why many people are scared to leave these types of jobs and try new things; they fear if they try and return later — even if it’s with a more varied and attractive profile — they won’t be able to get back in or will have to rejoin at a lower level.
These fears are not irrational. That said, no matter where you start your career journey and how grueling your interview process was, your career (and your soul) is going to be hindered if you stop learning. One route to continue growing at a steep curve is to leave your department or company. Better yet, switch industries entirely!
This could not be more true for VC investors who started their careers straight out of school, such as myself. Firstly, leaving VC helps you become a better investor since a huge part of the job is adding value to start-ups; the only way to get an intimate understanding of how to scale a company is to actually do that type of work. Gaining operating knowledge also fixes your investor blind spots. For example, it helps with reading between the lines on things founders promise and project. Most importantly, working at a start-up gives you the ability to authentically empathize with a founder’s journey.
Leaving your job / industry also diversifies the ways in which you can become successful. If you never leave VC, for example, your path to success is probably to wait 5–10 years and hope you get internally promoted after building a track record. If this doesn’t work, you could join another firm, but probably not at a partner level. That’s a very long road where all your eggs are in one basket. Alternatively, let’s say you join a start-up after working in VC. Now you can gain a track record and equity at different start-ups all while growing more attractive to VC hiring managers. I would argue that since VC is such a radically generalist job, if you leave to do almost anything else, you’re going to increase your chance of success in VC and at least double the potential paths to success in your career.
Though this piece is written through a VC lens, my point about leaving your job and/or industry to grow comes from my larger thesis that the most successful leaders in business are generalists, not specialists. In the dynamic world of tech and business no one is an expert on everything. If you have a mix of some sector specific knowledge and incredible soft skills you can make the right calls as a leader. Furthermore, no single job is going to shape you into the future career professional you want to be. You have to create this path yourself based on your learning goals and the future value you hope to create. All of which is to say, whatever industry you work in don’t be afraid to take the plunge and leave your comfy surefire linear path to success. The straightest path probably isn’t the best path and definitely isn’t the most enriching or the most fun. That’s why I broke out of my cushy VC job to try and found a digital health start-up. When that didn’t work out, I decided to join a digital health start-up. The changes have been scary but rewarding. Join me in choosing the winding road! :)
