Given her background, that’s not surprising. Dennis just joined the 15-person, San Francisco-based firm from the secondary investment firm 137 Ventures, where she led investments in Planet Labs, Wish and Course Hero. Dennis was also previously the COO of Airtime — Sean Parker’s video chat app — and worked as general counsel at Founders Fund and assistant general counsel at Peter Thiel’s Clarium Capital Management before that. (She also logged time as a litigator at Wilson Sonsini.)
We caught up with Dennis this morning to ask about her evolution from practicing lawyer to practicing venture capitalist, and how she landed at Initialized, an early-stage venture capital firm cofounded six years ago by former Y Combinator partners Garry Tan and Alexis Ohanian. Our chat has been lightly edited for length and clarity.
TC: Congrats on the new gig. How did you wind up at Initialized?
ALD: My friend Eric Woersching had joined as a general partner in January. We worked at Clarium together a number of years ago [Woersching was a financial analyst there] and he reached out to me and we started talking about what Garry — who I’d heard of but didn’t know at the time — was up to.
TC: Your background is interesting. You were a lawyer while you worked for Peter Thiel. How did you make the leap into investing?
ALD: Even at Founders Fund, I was interested in both the investment side and operations side and I’d wanted to move out of my legal role and had the opportunity to do a bit of that as the fund was growing so much during [my time there]. I did have the feeling that to get a fulsome sense of the venture ecosystem, I’d need to see it from the founder’s side; when [Founders Fund cofounder] Sean Parker left to start Airtime, it seemed like a great opportunity for me to get my hands dirty, so to speak.
ALD: Obviously it had a lot of investor interest. It had its own press engine. Operationally, I learned a ton of lessons. I learned that consumer is really hard. [Laughs.] Distribution is very important. Culture and communication is key in terms of making a team cohesive. I also learned the value of a great dev team.
TC: Initialized seemingly has a big team for the amount of money it’s managing.
ALD:. Most of the people have come on in last six or so months. It is really unusual to see an early-stage fund with so much personnel. It’s capital intensive to pay people. It isn’t cheap to live in the Bay Area. But I think it’s a testament to Garry’s vision and leadership that people have been willing to tighten their belts and work on something they find meaningful. I know I want to be a part of this as it’s taking off.
TC: The firm seems very services oriented, which is unusual for its size. How big is its current fund, and how many companies are part of its portfolio?
ALD: Its [current] and third fund is a $125 million fund; we’ve funded 26 or 27 companies [using that capital]. Altogether, across all funds, we have more than 100 active portfolio companies.
TC: Of the 15 employees, how many are general partners?
ALD: There are four — Alina [Libova, who previously ran investments for Tamares Group], Eric, Garry, and Alexis.
TC: And what are meetings like? Do you know yet?
ALD: The team meets on a regular basis, every other week. The firm has also developed robust software that allows everyone to communicate and collaborate and share their opinions about companies.
TC: You’re not practicing law anymore; how does your law degree help you in your new role?
ALD: It’s very helpful in negotiating specific agreements. It’s helpful from a fund formation perspective. Even though I don’t actively practice law and haven’t for the past few years, [a background in law] gives you critical thinking and reading comprehension skills that are broadly applicable in all aspects of life.
And each of us is pitching in wherever we can be helpful. It’s very exciting to be here. It really does feel like a startup.