Founder Characteristics & Traits That Sydney Looks For

5 Jul 2023 · 2 min

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In this interview excerpt, Sydney explains that the most important characteristic she seeks in founders is thoughtfulness. She emphasizes that founders don’t need to have a definitive answer to every question, but they must demonstrate that they have considered the various dimensions of their business and can articulate the pros and cons of different options. Sydney uses the classic marketplace "chicken‑and‑egg" problem as an example, noting that founders often propose overly simplistic solutions. She values founders who acknowledge the complexity of such challenges, recognize the validity of the investor’s concerns, and then propose a nuanced, defensible strategy that could become a sustainable moat for the business.

Could you maybe share some like the kind of characteristics or traits of, you know, some of the best founders that you kind of see that you might look for?
One thing I really look for in founders is just thoughtfulness. I'd say a founder doesn't need to have an answer to every single question I ask. They don't need to have a, yes, this is the only option, this is the truth in this world. But the founder needs to have thought about every aspect of the business. You know, there's, it's very rare that I ask the founder a question they've never thought about before. And so I want to see that thoughtfulness of response that shows that they're considering the pros and cons of the different options. I think one of the pitfalls is sometimes I'll ask a founder about something in the business that's been particularly tricky. And a classic example for marketplaces is chicken and the egg problem. And the founder will respond, well, we'll do this and that will solve, you know, the chicken and the egg problem. Like, we'll, we'll be good. And it's like, actually, this— there's no way that the solution is that simple. There's no way that there's not more to that answer. And so it's okay to say, actually, I think the question that you're bringing up. I think the concern you're bringing up is very valid. And actually, that's part of what makes my business great is if I'm able to solve that, that's a natural moat where I'm able to build the business while others are struggling with this challenge still. And here's how I think is the best way to solve that challenge. So I think I got a little bit lost and went on a rant, but that's one answer to the question.
If only it was that easy with marketplaces, right?
If only, yeah.