Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Okay, so let's start off, and this, we're not going to start off with the beginning, how did you get into it, but am I right, you met Chris at South by Southwest?
A Yeah, I think this will be almost a decade since that South by, but, um, I met him at South by in a, uh, a late night, uh, jam session put on by, uh, a former client at my agency, CA, uh, Gary Vaynerchuk. And Gary, Uh, was at the time a wine lifestyle expert, uh, and was sort of using his knowledge of the wine ecosystem to get really interesting people together and start having debates, uh, about tech and where the tech ecosystem was heading. And that's where I met Chris in, uh, in, I think the Hilton in his, in like a tiny little, uh, you know, twin bed suite at the Hilton hotel talking about, uh, the future of tech and drinking far too much wine.
AI assessment note: “Yeah, I think this will be almost a decade since that South by”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And then you guys stayed in contact since then for, for a couple of months before he asked you to join?
A For years. I mean, like for eight years, uh, Chris and I became closer and closer friends and kept sort of running across each other. So he did more stuff in media and entertainment and I started building out a tech practice at CAA. Our paths just naturally crossed over and over. And, uh, a couple times over the, over the course of that period, he, uh, he suggested that maybe I look into taking a job at one of his portfolio companies. Um, and I was just having, having probably the best time, you know, I could in that period of, uh, work at CAA. And so I had no interest in never leaving. The plan was to dye in a suit at that place. I loved it. I loved the clients. I loved, I loved the agents. I loved, uh, some of my best friends in the world are still people that I've made while, uh, while growing up at CAA. Best mentorship. And yet, uh, over, over time, he and I became closer and closer, and then eventually, he asked me to join.
AI assessment note: “For years. I mean, like for eight years”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Okay, so let's start off, and this, we're not going to start off with the beginning, how did you get into it, but am I right, you met Chris at South by Southwest?
A Yeah, I think this will be almost a decade since that South by, but, um, I met him at South by in a, uh, a late night, uh, jam session put on by, uh, a former client at my agency, CA, uh, Gary Vaynerchuk. And Gary, Uh, was at the time a wine lifestyle expert, uh, and was sort of using his knowledge of the wine ecosystem to get really interesting people together and start having debates, uh, about tech and where the tech ecosystem was heading. And that's where I met Chris in, uh, in, I think the Hilton in his, in like a tiny little, uh, you know, twin bed suite at the Hilton hotel talking about, uh, the future of tech and drinking far too much wine.
AI assessment note: “Yeah, I think this will be almost a decade since that South by”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And then you guys stayed in contact since then for, for a couple of months before he asked you to join?
A For years. I mean, like for eight years, uh, Chris and I became closer and closer friends and kept sort of running across each other. So he did more stuff in media and entertainment and I started building out a tech practice at CAA. Our paths just naturally crossed over and over. And, uh, a couple times over the, over the course of that period, he, uh, he suggested that maybe I look into taking a job at one of his portfolio companies. Um, and I was just having, having probably the best time, you know, I could in that period of, uh, work at CAA. And so I had no interest in never leaving. The plan was to dye in a suit at that place. I loved it. I loved the clients. I loved, I loved the agents. I loved, uh, some of my best friends in the world are still people that I've made while, uh, while growing up at CAA. Best mentorship. And yet, uh, over, over time, he and I became closer and closer, and then eventually, he asked me to join.
AI assessment note: “For years. I mean, like for eight years”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And then what would you most like to improve of those KPIs? Is there any way you're like, you know what, I need to do better?
A No question. I need to do better on time management. Uh, and I think this is one that I just need to Part of the challenge you have when it's a really light fund in terms of headcount, it's Chris Jackson and I, and because we're so collaborative and we do see a lot of deals out there, I need to get better at how I manage through that time. And we've just brought on a new hire to sort of help focus, uh, focuses in on building out processes to better manage how we're allocating that time. A third, a third, a third between like existing portfolio companies, finding and nurturing new portfolio, uh, new investment opportunities. And then sort of building out the service side and network and conferences and LP management and fund management of our world.
AI assessment note: “No question. I need to do better on time management.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q I think absolutely looking at your portfolio, you haven't suffered by being in LA, that's for sure. Um, but I'd also like to dig into the, you said that we talked about kind of the cult of the VC now, and the brand around them. And so how have you approached your personal brand building as you've kind of set out in your career of venture?
A You know, it's interesting. It's a, this is something I've struggled with. And I think a lot of people who come into an existing brand with a personality that sort of looms larger than life, Having built it. I mean, lowercase is Chris. Chris has built this over the better part of the year. He is incredible at it. He's an amazing storyteller, and he's a great personality to rally around. And so I, I don't think, and, and combine that with, at eight years at CAA, uh, You're not trained to, to build your own brand. And so I think Chris has challenged me over the last few years to really get out there more. He, he repeatedly tries to get me to go out and blog. I've done it a few times. It's not my natural state. If you, if you want the truth of it, the, the categories that I feel like I can express my own personality. So that's, that's more important to me than brand building is like letting people know the person that I am. I think moments like this are frankly, uh, the best, the best version for me. I met Chris in a conversation in a jam session where we're both going back and forth, having a discussion. This is where I'm most comfortable. And it's also where I'm most comfortable with entrepreneurs is sitting down and bouncing ideas back and forth and having a discussion about why they think away or why I think away. I get that out through conversations through podcasts. I get th…
AI assessment note: “I get that out through conversations through podcasts. I get that out through video.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q So where do you stand on your location then, being in LA? Do you sometimes feel that you potentially miss out? I know LA has a hugely blossoming tech scene, but how do you position yourselves with that thought?
A Yeah, we, uh, we, we, we're fortunate enough, uh, we do, we do a couple things. So one, I think being outside of the echo chamber, uh, Chris has talked about this a lot. The reason why he moved out of SF to Truckee years ago, I mean, Chris hasn't been in San Francisco for the better part of a decade, largely because he wanted to be more focused with his time and be more on the offense in terms of how he used his time. I think we benefit from being in LA by that same token. We don't have to be caught up in every single cocktail party, every single event. That sort of momentum can be overwhelming when you're in an ecosystem, and it's really easy to conflate work and those events. At the same time, we're close enough that I'm in San Francisco two days a week, and on a moment's notice, we'll fly up and meet with an entrepreneur if timing, if timing necessitates it, and combine that with video conferencing and phone, I think you really can build both a company and a venture firm anywhere, as long as you put in the time and work, whether through travel, conferences, phone, responsiveness through, through email, all of those things enable you to do this job really, really well from anywhere, and so we, we seem to, thus far, have not suffered from, uh, From being outside of the echo chamber. I think it's a competitive advantage for us, uh, as well, just cause the, you know, I think bui…
AI assessment note: “I think it's a competitive advantage for us, uh, as well”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q I think absolutely looking at your portfolio, you haven't suffered by being in LA, that's for sure. Um, but I'd also like to dig into the, you said that we talked about kind of the cult of the VC now, and the brand around them. And so how have you approached your personal brand building as you've kind of set out in your career of venture?
A You know, it's interesting. It's a, this is something I've struggled with. And I think a lot of people who come into an existing brand with a personality that sort of looms larger than life, Having built it. I mean, lowercase is Chris. Chris has built this over the better part of the year. He is incredible at it. He's an amazing storyteller, and he's a great personality to rally around. And so I, I don't think, and, and combine that with, at eight years at CAA, uh, You're not trained to, to build your own brand. And so I think Chris has challenged me over the last few years to really get out there more. He, he repeatedly tries to get me to go out and blog. I've done it a few times. It's not my natural state. If you, if you want the truth of it, the, the categories that I feel like I can express my own personality. So that's, that's more important to me than brand building is like letting people know the person that I am. I think moments like this are frankly, uh, the best, the best version for me. I met Chris in a conversation in a jam session where we're both going back and forth, having a discussion. This is where I'm most comfortable. And it's also where I'm most comfortable with entrepreneurs is sitting down and bouncing ideas back and forth and having a discussion about why they think away or why I think away. I get that out through conversations through podcasts. I get th…
AI assessment note: “I get that out through conversations through podcasts. I get that out through video.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q So where do you stand on your location then, being in LA? Do you sometimes feel that you potentially miss out? I know LA has a hugely blossoming tech scene, but how do you position yourselves with that thought?
A Yeah, we, uh, we, we, we're fortunate enough, uh, we do, we do a couple things. So one, I think being outside of the echo chamber, uh, Chris has talked about this a lot. The reason why he moved out of SF to Truckee years ago, I mean, Chris hasn't been in San Francisco for the better part of a decade, largely because he wanted to be more focused with his time and be more on the offense in terms of how he used his time. I think we benefit from being in LA by that same token. We don't have to be caught up in every single cocktail party, every single event. That sort of momentum can be overwhelming when you're in an ecosystem, and it's really easy to conflate work and those events. At the same time, we're close enough that I'm in San Francisco two days a week, and on a moment's notice, we'll fly up and meet with an entrepreneur if timing, if timing necessitates it, and combine that with video conferencing and phone, I think you really can build both a company and a venture firm anywhere, as long as you put in the time and work, whether through travel, conferences, phone, responsiveness through, through email, all of those things enable you to do this job really, really well from anywhere, and so we, we seem to, thus far, have not suffered from, uh, From being outside of the echo chamber. I think it's a competitive advantage for us, uh, as well, just cause the, you know, I think bui…
AI assessment note: “I think it's a competitive advantage for us, uh, as well”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And then what's been the biggest learning experience from working with Chris?
A Other than, uh, other than how to avoid getting on Gigi's worst dress list, um, there's a lot. It's like, it's sort of a, it's an overwhelming amount, um, watching the way that he Balance his life and sort of where he places priorities, you know, for people that don't know him, he's, uh, he's the best father and husband that I've ever seen. Um, and really is sort of like, he's one of these people that's inspired me that you can't have all of that and build with an incredible partner in crystal and have, and be conscious and a present parent and still go out there and kill it. But I think Chris, the thing I've learned most is how really to be Uh, to not fall prey to short-term gains and compromises. There's not been a single decision that I've had to make while working with Chris at Lowercase where I felt like it was a compromise of my moral compass.
AI assessment note: “the thing I've learned most is how really to be Uh, to not fall prey”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q But, It will continue. I'm sorry. Um, so yeah, so you wash, uh, your suit off. So what did he mean by that? And how did you interpret that?
A Um, I think, I think he meant a few things. I think, uh, I think one of his fears in bringing me on, uh, was that would I be too corporate in my thought process and be able to sort of go out there? I mean, part of the CAA ecosystem is that you are really the person you are never in the spotlight. You're not the one speaking. You're not the one taking, uh, credit for anything, uh, You're not the one brand building yourself. Everything, all of your effort is in service to the client and building their brand and building them. And so the agents are generally the people behind the scenes. Increasingly, I think we're seeing, we've been talking a little bit about this, Harry, like that shift, uh, in venture towards being more of a, more of a personality and expressing yourself and not being, uh, you know, a wilting lily and sort of going out there. And, uh, and being more front and center in your conversation and your opinion and your thought leadership. And I think that's part of what he was saying. This isn't a job where you can actually wear a suit. You have to be, you get to sort of go out there and express a little bit more of your personality, whether that's, you know, normal clothes or whether you're wearing a cowboy shirts all day long.
AI assessment note: “I think one of his fears in bringing me on, was that would I be too corporate”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q But I want to move back to something we discussed there, and that was kind of the personalization of VCs in the emerging ecosystem. And do you think we have seen this kind of rise of the celebrity figure in the funding environment?
A Yeah, I think, I think we've seen a few sort of themes coalesce all at the same time. One of those themes is everybody is more accessible today. Everybody is Uh, the social networks have been built around, uh, human beings, not necessarily around brands, and so, for a human being to build a brand, uh, is far easier than ever before, and actually, um, these networks give, sort of, uh, preferential treatment to the person, and so, I don't think, uh, the VC of today can hang behind a Sand Hill Road address anymore, and pretend like that brand will become, or maintain its, uh, supremacy, uh, In this ecosystem. I think you have to more and more expose yourself to the, the world and be covered as a person who has individual thoughts, individual opinions, and be willing to sort of express those and build your own following and be interactive in all of those communications. I don't think we are in a world where like, you can just sit behind that, that address and hope that the world will come to you. I think there's a lot of de-risking that happens in venture capital on both sides, both when you make an investment and when you take an investment. And part of the de-risking for an entrepreneur taking investment is they want to know who they're getting in business with. They want to know how they'll react. They want to have information. I think one of the fantastic things about YC and wh…
AI assessment note: “for a human being to build a brand, uh, is far easier than ever before”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And then the hardest thing about making the transition to VC for you?
A Uh, the hardest thing is, from CAA to lowercase, I'll be more specific, was Being surrounded by people all day long. This, this career is, uh, the venture career, even if you're part of a partnership, can be a lonely one. You're often standing out on a ledge defending investments, uh, when people still think they're crazy, and often the best ones are, um, and you sort of have to defend that, uh, in my case, I get, you know, Chris to back me on those, but even sometimes he and I will have, you know, disagreements on those companies, and so you're, It's a far lonelier place than being able to run down the hall and be, you know, see 15 of your best friends and build a relationship with, uh, uh, with those agents over time and have your, sort of, CA was entirely predicated on teamwork and, uh, and big, sort of, uh, service groups surrounding clients and all pushing forward in the same direction, and I get some of that with working with the portfolio companies, but, uh, but it's a very different sort of process. I'm no longer wearing a suit. I work from home. We don't have an office. I work from home. I had three people a foot away from me at CA, and today we have three people spread across, uh, you know, a few cities in, uh, in lowercase, and so a slightly different environment.
AI assessment note: “the venture career, even if you're part of a partnership, can be a lonely one”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q And then the hardest thing about making the transition to VC for you?
A Uh, the hardest thing is, from CAA to lowercase, I'll be more specific, was Being surrounded by people all day long. This, this career is, uh, the venture career, even if you're part of a partnership, can be a lonely one. You're often standing out on a ledge defending investments, uh, when people still think they're crazy, and often the best ones are, um, and you sort of have to defend that, uh, in my case, I get, you know, Chris to back me on those, but even sometimes he and I will have, you know, disagreements on those companies, and so you're, It's a far lonelier place than being able to run down the hall and be, you know, see 15 of your best friends and build a relationship with, uh, uh, with those agents over time and have your, sort of, CA was entirely predicated on teamwork and, uh, and big, sort of, uh, service groups surrounding clients and all pushing forward in the same direction, and I get some of that with working with the portfolio companies, but, uh, but it's a very different sort of process. I'm no longer wearing a suit. I work from home. We don't have an office. I work from home. I had three people a foot away from me at CA, and today we have three people spread across, uh, you know, a few cities in, uh, in lowercase, and so a slightly different environment.
AI assessment note: “This, this career is, uh, the venture career... can be a lonely one.”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q But, It will continue. I'm sorry. Um, so yeah, so you wash, uh, your suit off. So what did he mean by that? And how did you interpret that?
A Um, I think, I think he meant a few things. I think, uh, I think one of his fears in bringing me on, uh, was that would I be too corporate in my thought process and be able to sort of go out there? I mean, part of the CAA ecosystem is that you are really the person you are never in the spotlight. You're not the one speaking. You're not the one taking, uh, credit for anything, uh, You're not the one brand building yourself. Everything, all of your effort is in service to the client and building their brand and building them. And so the agents are generally the people behind the scenes. Increasingly, I think we're seeing, we've been talking a little bit about this, Harry, like that shift, uh, in venture towards being more of a, more of a personality and expressing yourself and not being, uh, you know, a wilting lily and sort of going out there. And, uh, and being more front and center in your conversation and your opinion and your thought leadership. And I think that's part of what he was saying. This isn't a job where you can actually wear a suit. You have to be, you get to sort of go out there and express a little bit more of your personality, whether that's, you know, normal clothes or whether you're wearing a cowboy shirts all day long.
AI assessment note: “This isn't a job where you can actually wear a suit.”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q And then before we dive into a quick fire round, I want to, I just want to speak to you about your kind of investment decision making and how the process itself has altered over time. And as you, as I'm sure improved as an investor, how have you seen it change?
A Time will tell on whether the returns reflect successful alteration here. I think, if anything, I've gotten better at pattern matching in some senses, and fighting pattern matching in others. And so, I'll dive in a little bit there, like, um, you know, a partner like Chris to be a great mentor and sort of help me think through some of the things that we really care about in identifying qualities within an entrepreneur, and early social feedback, and early social success on companies, and, uh, you know, uh, social proofing, sorry, on companies, uh, and early metrics that sort of Defines, uh, sort of really dedicated user bases or customer bases early in a company's life cycle, or people who know how to iterate quickly around product and have a technical capacity. I think I'm getting better at identifying those sort of practices, but just in terms of the questions that you ask. To identify, understand an entrepreneur's motivation. The anti-pattern actually is, uh, sort of getting myself out of the early biases that we have in terms of the space that I've seen before, or this is a problem I've seen tackle before, and it's really easy, I think, for, for, because there's so much deal flow and so much sort of, uh, noise in the system, especially right now, it's really easy to discount companies and, and quickly write them off rather than take a deeper look at them. And, uh, I guess h…
AI assessment note: “I've gotten better at pattern matching in some senses, and fighting pattern matching in others.”
Partly raw tape
D 3 · C 5 · P 4 · Cm 4 4.00
Q Chris often states, you know, Chris, uh, has been covered obviously in many podcasts, Cross, and, and he also states how impressed he was by you, and he says there was this guy in the room, and no one kind of knew who he was, but everyone was like, holy shit, he's really, really smart. So, what, what were you guys chatting about? Because it always ends there. Was it-
A You know what's, Yeah, you know what's funny is, uh, I think I was pretty, pretty, I think I was at least a bottle of wine deep at the time, so maybe I was louder than normal, um, and that's saying something, because I'm a pretty loud kid for anybody that knows me, um, and I think I was just, at this moment in time, I, a little bit naive about who was in the room, so it was, it was people like Chris Saka, and Dave Morin, and Nat Van Horn, and Aaron Battalion, and Travis Glanick, and Garrett Camp, and people who now, I think I would have been intimidated in that moment in time, but I was totally unintimidated, largely by my own ignorance of, uh, of who they were. And I just sort of unleashed, like, all of my theses at the same time. And so, Chris and I ended up on the opposite side of arguments time and time again. And, uh, and a couple times got to a draw in terms of where we believe the world is heading and other people would chime in and sort of fall, uh, in, in a few of those cases on my side. I think that was one of those few times that Chris, who's a pretty big personality as you've come to see, uh, doesn't get challenged like that a lot. And, uh, we went at it a number of times and I think that, that back and forth built a really healthy foundation for how we interact today as partners. And so I'm not sure it's anything particularly Uh, earth shattering that I shared in t…
AI assessment note: “I just sort of unleashed, like, all of my theses at the same time.”
Answered raw tape
D 5 · C 4 · P 3 · Cm 3 3.90
Q And so, so what is it? What is the icky rule? We often hear about this kind of taboo industries. Is that like porn? Is that, uh, betting? Yeah.
A Yeah, it's definitely those. But it's, no, it's not just those. It's, uh, you know, it's working with people who, who might not have the right motivation, who might take that short-term route, who, who you wouldn't be proud to tell your mom or your dad about the investment you made. And so, I've always, I felt proud of those investments, and I feel like they're, like, I'm really fortunate. I have a lot of people who put a lot of faith in me and capital behind that faith to help bring companies into the world that in the hope, you know, I know this sounds a little, like, Pollyannish, but it, you know, hopefully make the world a better place, uh, and in addition to that are great businesses, and so to never feel like you have to compromise that is really special.
AI assessment note: “Yeah, it's definitely those. But it's, no, it's not just those.”
Answered raw tape
D 5 · C 4 · P 3 · Cm 3 3.90
Q And then before we dive into a quick fire round, I want to, I just want to speak to you about your kind of investment decision making and how the process itself has altered over time. And as you, as I'm sure improved as an investor, how have you seen it change?
A Time will tell on whether the returns reflect successful alteration here. I think, if anything, I've gotten better at pattern matching in some senses, and fighting pattern matching in others. And so, I'll dive in a little bit there, like, um, you know, a partner like Chris to be a great mentor and sort of help me think through some of the things that we really care about in identifying qualities within an entrepreneur, and early social feedback, and early social success on companies, and, uh, you know, uh, social proofing, sorry, on companies, uh, and early metrics that sort of Defines, uh, sort of really dedicated user bases or customer bases early in a company's life cycle, or people who know how to iterate quickly around product and have a technical capacity. I think I'm getting better at identifying those sort of practices, but just in terms of the questions that you ask. To identify, understand an entrepreneur's motivation. The anti-pattern actually is, uh, sort of getting myself out of the early biases that we have in terms of the space that I've seen before, or this is a problem I've seen tackle before, and it's really easy, I think, for, for, because there's so much deal flow and so much sort of, uh, noise in the system, especially right now, it's really easy to discount companies and, and quickly write them off rather than take a deeper look at them. And, uh, I guess h…
AI assessment note: “I've gotten better at pattern matching in some senses, and fighting pattern matching in others.”
Answered raw tape
D 5 · C 4 · P 3 · Cm 3 3.90
Q And then hustle. How do you define it, and is it good? Is it bad? What are your thoughts?
A Hustle is repeatedly understanding how to offer value to others In advance of asking for value for yourself. Not only do that, but doing it at a cost, often at a cost to yourself in order to improve somebody else's situation, because you know that the longterm gain from that interaction Will outweigh any short-term costs. Hustle is contributing to somebody else's success without asking for anything, and really not even, like, with the, like, there's, there's a challenge here around hustle. Oh, in a couple months, I'm gonna try to cash in on that. It's really, truly believing that if I just add value to other people, that there doesn't need to be a cash-in moment. That you're just doing it because it's the right thing to do, because you love doing it, and because you can't help somebody else. That's a whole other level of hustle. I think today, hustle gets marred in this idea of, like, Oh, it's just like, I, I add value short term, and then eventually I'm going to ask him for a favor. I think there's a difference between that, what some people out there have executed on.
AI assessment note: “Hustle is repeatedly understanding how to offer value to others In advance of asking”
Answered raw tape
D 4 · C 4 · P 3 · Cm 3 3.60
Q How do you deal with that long feedback loop?
A It's the hardest, it's the hardest thing. I, I think I look to People who have been through multiple cycles and get advice from them. Uh, I've had a few conversations lately with VCs and, and people in different industries that have had multiple ups and up and down cycles, because if my, if my early proxy, uh, signal for success in selection is follow on fundraising and health of those businesses, I can track health of business myself, but follow on funding is something that today because of the fundraising environment and cheap and cheap access to capital, You're seeing perhaps a little too much exuberance in terms of like the fall on financing. So that, that signal has gotten a little bit muddy, muddied, uh, and muddled over the last couple of years. And so I guess I have to look to, to people who have been through, uh, multiple up and down cycles for sort of advice on is my selection process correct and have a little bit of faith. I'm lucky that I have a stock in a mentor who's seen, uh, up and down and also is sort of a good, uh, good sounding soundboard for a lot of this. And if the last is service, uh, Uh, this is one I spend most of my time on, because I believe it feeds back into the other two really well, uh, both in, in terms of selection in that we try to only select companies that we can help and make an impact on. Otherwise we're sort of playing public stocks. Ther…
AI assessment note: “I look to People who have been through multiple cycles and get advice from them.”
Partly raw tape
D 3 · C 4 · P 3 · Cm 4 3.45
Q Chris often states, you know, Chris, uh, has been covered obviously in many podcasts, Cross, and, and he also states how impressed he was by you, and he says there was this guy in the room, and no one kind of knew who he was, but everyone was like, holy shit, he's really, really smart. So, what, what were you guys chatting about? Because it always ends there. Was it-
A You know what's, Yeah, you know what's funny is, uh, I think I was pretty, pretty, I think I was at least a bottle of wine deep at the time, so maybe I was louder than normal, um, and that's saying something, because I'm a pretty loud kid for anybody that knows me, um, and I think I was just, at this moment in time, I, a little bit naive about who was in the room, so it was, it was people like Chris Saka, and Dave Morin, and Nat Van Horn, and Aaron Battalion, and Travis Glanick, and Garrett Camp, and people who now, I think I would have been intimidated in that moment in time, but I was totally unintimidated, largely by my own ignorance of, uh, of who they were. And I just sort of unleashed, like, all of my theses at the same time. And so, Chris and I ended up on the opposite side of arguments time and time again. And, uh, and a couple times got to a draw in terms of where we believe the world is heading and other people would chime in and sort of fall, uh, in, in a few of those cases on my side. I think that was one of those few times that Chris, who's a pretty big personality as you've come to see, uh, doesn't get challenged like that a lot. And, uh, we went at it a number of times and I think that, that back and forth built a really healthy foundation for how we interact today as partners. And so I'm not sure it's anything particularly Uh, earth shattering that I shared in t…
AI assessment note: “I just sort of unleashed, like, all of my theses at the same time”
Answered raw tape
D 4 · C 3 · P 3 · Cm 3 3.30
Q How do you deal with that long feedback loop?
A It's the hardest, it's the hardest thing. I, I think I look to People who have been through multiple cycles and get advice from them. Uh, I've had a few conversations lately with VCs and, and people in different industries that have had multiple ups and up and down cycles, because if my, if my early proxy, uh, signal for success in selection is follow on fundraising and health of those businesses, I can track health of business myself, but follow on funding is something that today because of the fundraising environment and cheap and cheap access to capital, You're seeing perhaps a little too much exuberance in terms of like the fall on financing. So that, that signal has gotten a little bit muddy, muddied, uh, and muddled over the last couple of years. And so I guess I have to look to, to people who have been through, uh, multiple up and down cycles for sort of advice on is my selection process correct and have a little bit of faith. I'm lucky that I have a stock in a mentor who's seen, uh, up and down and also is sort of a good, uh, good sounding soundboard for a lot of this. And if the last is service, uh, Uh, this is one I spend most of my time on, because I believe it feeds back into the other two really well, uh, both in, in terms of selection in that we try to only select companies that we can help and make an impact on. Otherwise we're sort of playing public stocks. Ther…
AI assessment note: “I look to People who have been through multiple cycles and get advice from them.”
Answered raw tape
D 4 · C 3 · P 3 · Cm 3 3.30
Q That's really interesting. Cause I always kind of worry cause you know, uh, in terms of meetings of being kind of busy, but not productive. Do you ever get the feeling that just by filling a diary, it is potentially busy, but not productive?
A Yeah, it's a, it's a constant balance for me. It means it's other things suffer in my life. I'm not, and you, I think one of the, one of the things you wanted to talk about a little bit today was around You know, areas that I can improve, uh, you know, as a VC and my responsiveness over e-mail is clearly a category that I need to get better at. And I, and I am ruthlessly efficient in that world and still, uh, not where I need to be if I'm measuring my KPIs, honestly. That is definitely a category. But, but I do think that, like, curating the time that you spend with people and doing it in person And having meaningful periods of that time, and not just like a traditional meeting, but like something a little bit out of the ordinary, like a trip or something like that, where you're, where you're spending Concentrated periods of time with people. I do those things probably more often than most as well.
AI assessment note: “Yeah, it's a, it's a constant balance for me.”
Answered raw tape
D 3 · C 3 · P 3 · Cm 3 3.00
Q That's really interesting. Cause I always kind of worry cause you know, uh, in terms of meetings of being kind of busy, but not productive. Do you ever get the feeling that just by filling a diary, it is potentially busy, but not productive?
A Yeah, it's a, it's a constant balance for me. It means it's other things suffer in my life. I'm not, and you, I think one of the, one of the things you wanted to talk about a little bit today was around You know, areas that I can improve, uh, you know, as a VC and my responsiveness over e-mail is clearly a category that I need to get better at. And I, and I am ruthlessly efficient in that world and still, uh, not where I need to be if I'm measuring my KPIs, honestly. That is definitely a category. But, but I do think that, like, curating the time that you spend with people and doing it in person And having meaningful periods of that time, and not just like a traditional meeting, but like something a little bit out of the ordinary, like a trip or something like that, where you're, where you're spending Concentrated periods of time with people. I do those things probably more often than most as well.
AI assessment note: “Yeah, it's a, it's a constant balance for me.”