I’ve Been in Venture Capital for Two Months. Here’s What Still Makes No Sense

Leah Fessler
The Startup
Published in
7 min readDec 22, 2020

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Tryna see the forrest through the trees

People often ask me how I got into VC. It’s a difficult question to answer because the truth isn’t sexy or fun. Getting hired in VC was a winding, frustrating, and often draining process during which I repeatedly convinced myself this wasn’t the path I wanted to take, then reignited interest. I’m happy to share the nitty gritty with anyone who asks. While I was lucky to have a few investors believe in me, more often than not, interview processes left me exhausted and underwhelmed.

When I wasn’t “looking,” the opportunity to join NextView Ventures arrived. Getting an offer was a tremendous privilege; I do not take it lightly, and I know my gain was the loss of other candidates who were likely equally if not more qualified. Now two months into the job, I’ve spent a good deal of time reflecting on what would be helpful to share about my early days in venture. There are many resources available on how to get into venture, and millions of “what I’ve learned in my first 60 days as a VC” posts. Instead of contributing to the noise, I decided to get real and share what I’m still struggling with. Which is a lot!

Non-partner venture roles are not easy. They’re high pressure, often no- or low carry, and quite vague. You enter not knowing what you’re supposed to do, and you’re rarely presented with a manual. I tend to gauge my professional confidence based on how frequently I use the word “should” — a trick I learned in therapy. My therapist flags when I’m speaking about what I “should” be doing or feeling, as opposed to what I am doing, feeling, or thinking. After two months in venture, I’m saying “should” a lot.

I share this reality not to downplay my abilities or the support of my team — which is amazing. Nor am I embarrassed by my “should”-ing; it’s a sign that I’m pursuing an opportunity that makes me uncomfortable, and that’s a sign I’m learning. Those who aren’t should-ing have either been at this way longer than I have, or they’re lying. I don’t enjoy being bored, and believe that life is too short to stay professionally comfortable.

I’m being honest about my insecurities and confusions because after cutting my teeth at Bridgewater Associates, one of the most radically transparent workplaces, and building a journalism…

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Leah Fessler
The Startup

Investor at NextView Ventures. Journalist. Thinking about gender, equality, and pugs. Formerly at Chief, Quartz, Slow, Bridgewater Associates, Middlebury.