The Exchanges

Q What kind of principles other than diligence have you learned from him? Like, what, what would you say, like, seriously carries on into how you view companies or view new trends in the venture capital world?

A Yeah, I think one of the most important things I learned from him is that it's all about the people. I think even, you know, when I was angel investing before joining Kleiner Perkins, I was really enamored by ideas, and I was very thesis driven, uh, and, you know, I had this view of where I thought the, where the world was going, and John Doerr taught me Like look to the founders to tell you where the future is going and really focus on, on the people. Um, and another lesson I learned is like, you know, some company, uh, some VC firms rather, uh, you know, take a more active stance and swapping out CEOs if the company's not performing well. But, uh, something I learned is like, that's usually, it usually doesn't work out. So, you know, you're really, In with this founder for the long haul, uh, and it, which is why it's so important that you're backing the right people.

AI assessment note: “one of the most important things I learned from him is that it's all about the people.”

Q topics to cover today, including lessons from your mentor, John Doerr, the race to a hundred million dollar ARR as the new key milestone for early stage companies, how long journey prices early stage rounds, and what metrics and signals you're looking for for follow-on financing. But to start, you've become famous for this winning founder theory called the Riz and the Tiz. Could you just unpack this for us?

A Uh, yes, of course. So this is kind of how we think about evaluating founders at Long Journey. Uh, literally in our investment committee meetings, uh, we talk about whether or not this founder has the right balance of Riz and Tiz. And what that means, Riz, is charisma, of course, which is, can this person recruit an amazing team? Uh, can they attract downstream funding? Uh, you know, are they gonna be a magnetic leader? We believe that neurodivergence is a superpower, and we look for people that live their lives differently, and I think it also represents an intensity and directness. So we want the balance of both, and we think it kind of takes both to be an amazing founder.

AI assessment note: “what that means, Riz, is charisma... We believe that neurodivergence is a superpower”

Q Are there any specific metrics that are associated with that? I know you said, like, a hundred X.

A That one, the, the proprietary, like that one I think is more vibes based, I will say. Like, what do we know that others don't know because we've had a longer standing relationship with the company? And like, what are others missing that we aren't missing or vice versa? So that's, that's what I mean by like, how proprietary is this? Um, then how de-risked is it? Like how, basically how much progress has the company made and in what areas have been de-risked, especially since Uh, our round of our previous round. Um, is this a public company founder? Like, can we see this founder being, you know, ringing the bell? Um, is this one of our breakout companies or is it, would we consider this a flagship deal or generational company? That's also kind of more vibes based. And then how do we think about downstream investor demand? Because, you know, compared to some other funds out there, we're a smaller fund. So we're not going to be able to capitalize the company throughout their entire journey. Uh, so what do we think the demand from our downstream peers will be?

AI assessment note: “like that one I think is more vibes based, I will say.”

Q One thing that Lee mentioned about you is that your building essentially An adult frat and sorority. So is this like how you're cultivating community? Like what does this mean?

A That I'm building an adult frat. That's a hilarious way to put it. Um, how do I put this? So I'm the youngest of four. I'm, I have three older siblings. So I was always like used to a lot of people being around. And as an adult, I don't know, I, and I'm an extreme extrovert. So I love being around people. I actually like don't like not being around people like being alone is like, you know, I'm like, when can I call my next friend to hang out? But, um, so I think I, you know, always kind of had a roommate when I, you know, I graduated college. I've had roommates and then I kind of just never stopped. So even like when my husband and I got married, we had a roommate and then, um, when she moved out, we got two more roommates. And then when they moved out, Uh, we actually invited another family to live with us. So we just always enjoyed having a lot of energy, a lot of different personalities and like living in community. And I think especially my husband's an introvert, and I think it's just a tall ask for your partner to be everything to you. I don't know. People are just relying so much on leaning so much on their partners for literally everything where if you live in community, you don't have to do that.

AI assessment note: “we just always enjoyed having a lot of energy, a lot of different personalities and like living in community”

Q It's like, I don't know, it's so stale. So, yeah, but do you really, I mean, you, you've come from traditional VC. Do you think it matters? Like, how much of it is nice to have versus like, An actual draw.

A I mean, it has to be true to yourself, right? Like I think, you know, KOTU has an excellent brand and their brand kind of is like excellence and prestige. And I think if they tried to do the same thing, it wouldn't feel authentic, but like this is who we are a long journey so that, you know, it, it has to be what's like right for you. I think if you, you know, are trying to, Um, kind of convey, yeah, it depends on what you're trying to convey and like what your values are. You know, our number one values chase the magically weird. I mean, not everyone is trying to chase the magically weird. So, you know, they're not going to have like seashells that you've collected on the beach in their office, but, um, Uh, but I think some people, even if it's not, doesn't feel weird or out there, are still, like, doing it really well, and, like, I have great brands, um, even if that brand is, like, more buttoned up.

AI assessment note: “I mean, it has to be true to yourself, right?”

Q Silicon Valley is actually, like, the epicenter of culture because so much innovation comes out of it, and that, like, that shouldn't be overlooked, but if, if, like, we have the opportunity to continue to, like, create new generations based off of whatever technology they're using or AI tools, like, that is important. Do you have any hot takes for us? What are your hot takes on the venture world?

A Okay, this isn't necessarily about the venture world. All the best content is in group chats. It's not in blogs. It's not on Twitter. The most like unhinged, best, hottest takes and interesting info is all on group chats. That's kind of my hot take. And so I think like, I am not as, you know, I'm not like doom scrolling on Twitter as much. I am just, but I am a part of a lot of like really interesting group chats. And that is where I think the most vibrant conversations are happening. I think most value add is dumb unless it's something we think about is documentary level value add. If you're not going to provide documentary level value add, then it like it doesn't matter and it's all super marginal.

AI assessment note: “All the best content is in group chats. It's not in blogs.”