Interview With Hadley Harris

How and why did you get started in private investing?

It was my co-founder Vic Singh. We went to undergrad together, and after we’d been working for a while, I started hearing about his experiences in VC at RRE. I’d been a developer and worked for tech companies, and I was starting to think about whether I wanted to become a founder myself, but I wasn’t sure if that was what I wanted. So when I heard from Vic about being a VC, I thought it sounded great, and it became an aspirational thing that we wanted to do at some point.

But we started to realize that VC is such an insular ecosystem. Some of the dynamics around this have changed, but at the time, breaking into VC would have meant sucking up to an old white guy for five to 10 years. Instead, we said, “We should start our own VC firm at some point.” A few years later, we decided to actually do it, so we brought in Tim, and then Nihal.

What is the single most important thing you value in an investment opportunity?

At the end of the day, it’s the founders. We’re investing at the seed stage, so a lot of things about the company will change over time, but the founder is the one thing that stays consistent. The more I do this, the more I put weight on finding incredible founders who are a great fit for whatever opportunity they’re going after, and I try not to get too caught up in the noise of the other aspects of the deal.

What are the best innovation themes that you see in the market today?

There are two themes I’m most excited about. The first is web3, particularly the ability for users and communities to own and have governance over the platforms that they’re building and utilizing.

The second is AI and machine learning — there’s not the same buzz around it that there was four or five years ago, but it continues advancing every year, and there’s no reason that’s going to stop. That means there are constantly new opportunities for founders to build something that just wasn’t possible a year ago.

Beyond economic return, what kind of impact do you hope to make with your portfolio?

I optimize for whatever’s most beneficial to the founder and their team. VCs have a split incentive model, where as an investor and board member, they have a fiduciary responsibility to the company, but as an investor who has LPs, we have a responsibility to maximize returns for those LPs. Sometimes those things deviate.

I’ve found that if I focus on the founders and the teams, even in a case where it may deviate from maximizing our returns, that’s only a short-term thing. In the long term, this is an industry where brand and reputation and trust matter, so focusing on the founders is very much in the best interest of our LPs.

What’s the most pressing challenge or pain point in managing your day-to-day private investment activity?

Honestly, it’s just keeping up with inbound opportunities. We’re really fortunate that we have a lot of founders who reach out to us and share their vision, but it’s challenging sometimes keeping up with that. It bothers me to not be responsive.

What is the hardest investment lesson you’ve learned and/or the biggest investment mistake you’ve made?

When we first started investing, we passed on Pinterest. That was obviously a mistake in the sense that it’s become a very large company. It was outside of our investment strategy at the time, and looking back, the thing that’s complicated is that yes, obviously we would have done extremely well had we invested in it, but also, you need to have a strategy. If you become unfocused and don’t stick to your strategy, then you could miss other opportunities that do align with your strategy. I don’t have a comprehensive solution for that, but at the end of day, I lean towards focus rather than breadth.

What are your favorite industry information sources and/or services?

I get a lot of my information on Twitter. (Shameless plug: Follow me: @hadley).

Please leave us a book recommendation.

Thinking in Bets by Annie Duke. It’s written by a poker champion who’s become an investment guru. In poker, there’s this concept of unknowable information, and it’s also true in seed-stage investments, where you have to try to make decisions and learn from the results when there are so many things that are unknowable.

What’s your favorite non-business interest or hobby?

Well, I became a father last year, so that keeps me pretty busy. Aside from child-rearing, I like playing tennis with Nihal and meditating. And until COVID, one thing that’s been a constant in my life is that I love to travel and eat different food around the world.

What’s your take on the private market overall?

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