DWAVC: Jeremy Kaufmann | Ep: 33

Speaker A: Welcome to Drinks with a VC where we explore the humanity behind investments. Grab your favorite drink and join us as we laugh, learn and liquor up with some of our favorite venture capitalists.

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Speaker A: 21 hello and welcome to another episode of Drinks with a vc. Thanks for joining us via whichever platform you're using to watch or listen in. I'm Vic Laquara, co founder and General Partner of seed fund Greencow Venture Capital and as always I'm joined by my friend and co hostess with the mostest, Brie Hanson, who leads biz dev at Ravix, a wonderful firm and sponsor that provides outsourced accounting, fractional CFO advisory and orderly wind down and HR consulting, headquartered in Silicon Valley. If you are a startup in need of those services or VC looking to make sure that your startups are in good hands, please give Bri a shout. Today's episode is also brought to you by Fidelity Private Shares. Fidelity is committed to supporting startups at all stages. Using the Fidelity Private Shares platform, founders can automate their equity management, operations and financings in a single collaborative hub. To learn more about how Fidelity can help your company grow, please check out the episode description below. So how's it Bri? Have you been keeping up with all the mind blowing announcements from OpenAI and Google I o over the past few days?

Speaker B: I'm glad our next guest has a strong drink for today because we're going to need it with all those announcements.

Speaker A: Yes we will, we will. And I think he's going to really bring a timely perspective to the conversation.

Speaker B: Tell you yes, I think you should get into your intro.

Speaker A: All uh, right. Perfect. Today's guest grew up in the suburbs of northern New Jersey just outside of New York City. He graduated summa cum laude from Dartmouth College with a BA in Economics and minor in Public Policy. Post college, he tested the waters as an intern at a Washington, D.C. think tank and was a research analyst for the Federal Reserve bank of New York for a few months before deciding to pursue a different path than the ones he imagined as a politician or economics professor. He joined the Analyst Group in Boston, where as a data scientist he worked on pricing strategy for new drug launches, healthcare outcome research, and market, uh, access studies. He eventually made his way to San Francisco and joined the sales and strategy and biz ops team over at Salesforce, where he drove initiatives in sales ops, partnerships and growth and served as the embedded strategy lead for A portfolio of more than 500 SMBs. He joined Scale Venture Partners in 2015, where he focuses on companies adding machine intelligence to business and vertical software, especially those industries untouched by the first decade of SaaS. His efforts have contributed to investments across vertical software, AI, automation, uh, and the intersection of machine learning and digital health. He sits on the board of Spot AI and is a board observer of both Riji, A Motive, Esper, Viz, AI and Prosha. Please welcome the pride of, uh, Pascack Hills High School, partner at Scale Venture Partners, Jeremy Kaufman. Hello, Jeremy.

Speaker C: Cheers. I don't think. I don't think anyone has mentioned Pascack Hills High School in at least 15 years. So I appreciate it.

Speaker B: I don't know if, you know, behind me, but this is Pascack Brook park, which looks very lovely here. Behind me. We are doing a nice, uh, drink today. What are we drinking? What did you pick for us?

Speaker C: We are drinking a White Russian today. I think the reason was. I think White Russian was probably the first cocktail I ever had, probably freshman year of college, and somehow in between then and now, I've probably had zero White Russians. When you said, pick a drink, this is amazing. Somehow I went back to the White Russians of the early college days.

Speaker A: I, uh, have to ask you, was the White Russian drink in college inspired by the Big Lebowski?

Speaker C: I think it was concurrent with the Big Lebowski. I think it was one of those, you're watching the Big Lebowski, and you have to therefore drink White Russians. Uh, and I will admit, I didn't get into the Big Lebowski as much as it was rumored to be. I had high. It was one of those things where you had really high expectations.

Speaker A: Yeah, yeah.

Speaker C: Somehow it just didn't live up to it, I guess. I think the dude is just a character you gotta understand at a different level. And at least the. The 19 year old version of me was not there.

Speaker A: So, yeah, I had to get on that level. I definitely remember a period where I'd watch it in a bathrobe with my guy friends, and we drink White Russians. It became a cult classic for our Vassar, uh, squash team. So I'm with you on this.

Speaker B: We played. We played the drinking game. You have to drink your White Russian every time they use the F word, which then you're pretty much dead by the end of the movie.

Speaker A: Yeah, absolutely, absolutely. So we've established that you don't typically drink this in any real setting beyond, like, special occasions. Now, what's your typical drink of choice when you're Hanging out and just tuning out.

Speaker C: Probably go with an Old Fashioned. I think it's. It. It goes down easy. I think it's just a very easy drink. The White Russian. I. You're right. I haven't had it in a couple of years, but it's not like I've never had it. It's just. I don't think of it as a. A weeknight kind of drink. Otherwise you are going to, uh, bear the consequences of that. Yeah.

Speaker B: Should we have them open the first gift?

Speaker A: Oh, yeah. Because you can't just have a White Russian with nothing else. Right. So let's. Let's open up the. The first box. This isn't technically our. Our VC unboxing. This is just a, uh, special opener.

Speaker C: A special opener for something to do with White Russians.

Speaker A: Yeah.

Speaker C: Uh, oh. Brownie inspired cookies with flavor. Girl Scout cookies. All right.

Speaker A: Yes.

Speaker B: They're the Adventure Foals, which is a theme we have for you as the vc who's done a lot of adventures in your life. So we thought you need some cookies with your milk.

Speaker C: I appreciate it. Adventureful Girl Scout cookies.

Speaker B: Yeah.

Speaker A: And for all of our listeners and viewers out there, we are sitting here recording on a Tuesday evening, and Jeremy still has things after this. I still have work that needs to get done. I know Bri does as well. We're turning it up on a Tuesday, only to have to turn it down a little bit and get back to work. So see how this goes.

Speaker C: This is not going to be one of those episodes where the guest is three or four drinks in. It is way too early for them.

Speaker A: That's true. I am drinking, uh, just because I put it into a tumbler. It's just to maintain the cool inside of the drink and just have my eyes intact. So we mentioned this is probably the first time that, that the words Pascack Hills High School has been uttered on a podcast in the last 15 years. You did grow up just right on the border of New Jersey, New York. We always love to dig into the childhood of our guests. What was your childhood like?

Speaker C: Yeah, I think you described it well. I'm somewhere between a book nerd and somebody that needs to get on my bike and, um, kind of go exploring. Actually prob. About 15 or 20 minutes from me, right across the New York state border is, uh, Harriman State park. And there's a really cool, uh, road that basically connects four or five different lakes. So I feel early in high school, probably, honestly back to middle school, I think that was probably, I think where I got My taste for the outdoors. And I think I started going up there with my dad, just exploring one of the hikes up there on, um, probably back and fourth or fifth grade, probably a couple of years later, I got excited about the fact that you could bike between the lakes. It was called Seven Lakes Drive. And then as high school kind of came about, I felt like most weekends I was trying to, uh, do something outdoors that was always a good place to be. Always a good hike, always a good bike. Growing up with a dog, it was always a good place to bring the dog outside. So, yeah, I always loved that park.

Speaker A: Do you have any siblings?

Speaker C: I do. I've got a younger brother. He's three years younger than me. We actually went to different schools growing up, which was pretty interesting. I stayed in the school in my town, just the public school in northern New Jersey. My brother ended up in sixth or seventh grade going to a different school. So we had the funny experience growing up of my brother and I, we were never really in the same school environment other than fifth grade and him in second grade. So I guess it. I guess that is an interesting thing I never really thought too much about. But yeah, we never overlapped in school or high school sports just because he was heading into New York City, into the New York City school world and I was in Jersey. So yeah, just pretty different school experiences.

Speaker A: Interesting. Were you at all competitive outside of that and the family dynamic of around, uh, the dinner table or whatever it might be?

Speaker C: I don't think so. I think, I think sometimes in venture, I know there's a couple of twins or pairs of sisters or brother that.

Speaker A: Yeah, absolutely.

Speaker C: And I always find that story very intriguing. I grew up, they did the same activities. Freshman year of college, I actually met, uh, triplets and I would become best friends with them. They all grew up in Madison, Wisconsin. They all played the same sports, same college. And I feel like my brother and I, we have a really good relationship, but he's in New York, I'm in SF right now. We play different sports. He had way better hand eye coordination than I did. Differential eventually lend itself to a different set of sports, but yeah, yeah, uh,

Speaker A: your parents, what did they do and what uh, did they support in terms of your sports and in terms of your studies? Were they supportive on that front and what ah, role do they play?

Speaker C: Yeah, my parents were. Look, I, I grew up in a town that's 50% Jewish by population. I would say had the classic northern New Jersey kind of Jewish family experience in the suburbs. I think obviously parents Are interested in your education, but they weren't the kind to intrude and get too down into the weeds. I was always a self starter, so it was never like they were giving their opinions. If I should choose this health, this science elective or this social studies elective, I think I was probably someone that put more pressure on myself than they did. So I felt no. It's interesting in my family, I think the four of us are all pretty different just in personality and interest, which is something I really like. Like my mom is really into not but professionally, but really into art and I think is her kind of happy place. My dad is. I think the tennis court is his happy place. Um, I think my brother probably tennis court slash being a comedian and m. Joking around with his friends and somewhere in the outdoors. So no, I. I always do look at those families where it's like the identical occupation or identical personality and I'm always like, oh, that's such a weird experience. Yeah. Just wasn't my experience.

Speaker A: Yeah.

Speaker B: Did your mom take you into the city a lot to go look at art?

Speaker C: Yes, absolutely. We always had a. In college or even now we have a Thanksgiving tradition of when my brother and I are back in town, we always. We'd go see a Broadway show. We'd go art museum. My brother and my mom would make fun of the fact of how little about art I knew and my lack of refined art artistic tastes. And I always had a lot to learn. A lot to learn from them.

Speaker B: Yeah.

Speaker A: When you were young, did you have a curiosity or exposure to technology and finance from any one source? Did you even have that curiosity or were you really more kind of focused on outdoors, focused on sports, etc.

Speaker C: As I said, I think. I think there were two parts to my personality, which was the movement part. And then, uh, I remember reading Harry Potter in first or second grade and that was the first book I read. And I think after that I just took off. And I feel for better or worse, I've always been someone that likes veering down a lot of different paths when it comes to reading. So I feel. I remember learning about Ruth Bader Ginsburg in the fourth grade and getting obsessed about the Supreme Court and lawyers and law and reading all the John Grisham books in the fourth grade. And then maybe in the middle school years it was off into the sciences and the medicine and technology. So I feel like I think I've always been a very curious person. One thing I do appreciate about this job is you get up in the morning and you've got 20 newsletters to read in front of you. Yeah, you've got government monopoly policy, you've got tech policy, you got law, you've got everything in front of you. And it's, you're literally getting paid to read things, which couldn't be more fun.

Speaker A: Before we get into the career side of things, I, uh, do want to point out something really interesting to our listeners in high school to go along with the kind of adventurous Dorsey side of things. You got into road biking and you decided to bike across the United States with a charity called Bike and Built, which must have been an incredible experience. Can you tell us a little bit about what motivated you to take on such a feat? Yeah, ah, bike riding across the US doesn't seem like something does someone does every day.

Speaker C: So yeah, it was actually, uh, the summer after my freshman year of college. I, you write, I got into road biking in high school. I did some short trips and then, yeah, the summer before college I had done a Seattle to San Francisco trip. It was probably the first time I'd spent meaningful time on the West Coast. And I think I fell in love with the Bay Area. Fell in love with long distance road biking in college. You're looking for something to do after your freshman summer. And I think I've always been a curious person. Like I think I've always been super intrigued of visiting new places. And I felt like a really interesting experience. I think every single night we ended up staying in a church or a school or a campground like all across the United States. We learned all the towns in Montana and Wisconsin and places where I hadn't been before. And I think just the experience of spending time in seeing something that I'd never seen before like the Great Lakes in Wisconsin or spending time on the Great Plains and seeing what Montana was like or Glacier national park. And I just, I felt like I learned a lot about parts of the country that I hadn't grown up in. And uh, one of the things I loved about Dartmouth was when my town, it was 50% Jewish town in northern New Jersey. And I remember thinking when I got to Dartmouth, wow, they're big country. There's a lot out there. And it was just cool every night to uh, you learn what are the delicacies that the uh, the Baptists are going to feed you at night and how does compared to the delicacies that some other religious group are going to feed? And you're right, all my comments are about food because when you're biking you're quite hungry. It Was also. It was a really cool organization. We each had to raise about 3,000 or $4,000 for the affordable cause. And which for a freshman in college was. That was a real effort to do.

Speaker B: Mhm.

Speaker C: Every week or so you'd be on a Habitat for Humanity build site. Um, and look, when this was going on, this was 2008. This was the great financial crisis this was. Housing policy was top of mind. People losing their homes. My first day of college, Bear Stearns literally went down. So I think housing policy was top of mind, myself as a policy person. And just what was going on in the country at that moment in time. It was a big deal.

Speaker A: Yeah, yeah. And by the way, for all of our listeners, bike, uh, and build, uh, a lovely charity, as Jeremy just mentioned, bringing awareness, providing resources and funding towards building more affordable housing across the country. We'll have the link in the episode description below. If you want to give generously there, that'd be awesome. Speaking of affordable housing, you're in San Francisco now and they're suffering. And I should say we. San Francisco's still home to me, even though I'm, um, in St. Louis. But obviously there's a housing crisis in San Francisco. What's your take on how to bring about meaningful change on that front?

Speaker C: Yeah, man. Wow, that's a tough one. Okay, I can go there if, I mean, if you're interested. Look, I think it's a fascinating subject, uh, to get myself out of the tech ecosystem. I'm a big Ezra Klein listener. I feel like Ezra Klein's always talking about the inabilities of liberals to build and how important that is. And I think San Francisco is a case study of that. Last weekend I was in Noe Valley looking at that famous $1.7 million bathroom, which is a travesty. Like, I think, honestly I. I think there's a lot of intersections here. There's the intersection of governance. Right now we're in a city where half the board is very much left and half the board is left center. And there's policy implications of that.

Speaker A: There's.

Speaker C: I think I'm a big fan of what Scott Weiner is trying to do with housing density and trying to push some of those. Because look, as an economist, you say there's a collective action problem. Everyone wants to keep their neighborhood, their neighborhood, keep the zoning as it is. Not build, not over, develop. And I. One of the organizations I joined when I moved to San Francisco was the YIMBY organization.

Speaker B: Yes. In my backyard.

Speaker C: I found that was a really interesting way of Looking at the problem, which is there's always a million and one people that are going to stand up and say don't build because those are the neighbors in that area. But there's a lot of voices that aren't being heard. And I think the YIMBY organization and what Scott Weiner is trying to do at the state level, he strikes me as he's fighting an uphill battle every single session. But it's really interesting.

Speaker A: Yeah. Staying on politics, I know that you try and you're a policy nerd and you're totally into policy in government.

Speaker C: Yeah.

Speaker A: We have an election cycle coming up and it's almost impossible, obviously with the trial that we've got going on now, it's almost impossible not to be immersed and oversaturated with Biden, uh, v. Trump. Do you try and how do you deal with that? Do you try and set up a wall and just peek over the wall a little bit? Or do you really dive into it? The law and the policy of it all gets you.

Speaker C: If I was being honest, the first thing I read in the morning is Politico. Then I go to 5:38. I actually went to college with Harry Anton who was two to Nate Silver. So yeah, love reading his posts, love reading his materials. I get my fill of my 10 minutes of what polls have come in, what's the new stories of the day and then it's off to the, it's off to the tech newsletter. So I've tried to balance it out. I know people have a lot of different personal reactions to it. I think, uh, I react, tend to at the information level. Like I want to know what's going on and I think it's important to at least know what's going on and you move on to the next thing in your day and yeah, sometimes you can get stuck in that rabbit hole.

Speaker A: But yeah, yeah, I think that's a really important point. Bree and I are talking about my mom and my dad the other day and they're like polar opposites. Right. My dad will watch the news until his eyes are bleeding. Right. But my mom on the other hand is. I don't want to know. It's just all soul crushing and I'm just not even going to watch any of it or read any of it. But I think there's like a middle ground that as uh, citizens, uh, and as uh, trying to be participants in the process, we've got to stay informed. So to mom and dad over there, find that middle ground like Jeremy has.

Speaker C: And I feel like, it's too. I think about. It's amazing how both in tech world and in policy world, we tend to operate. We swing wildly between two ends of the spectrum. Like, I was just listening to Ezra had. Ezra Klein had this drug policy expert talking about Oregon's drug legalization bill yesterday. And it was just, it's amazing how quickly these policy changes happen. And like in AI, it's the same thing. Oh, wait, all the value goes to the foundation model. Oh, wait, it doesn't. Oh wait, it does. And I, I feel like it is a good mental exercise to try to keep yourself grounded and not just be those wild swing type of things.

Speaker B: So question for you around your own activism. So you obviously like to consume political, um, knowledge. When do you make a change in your life? When is when. What is the thing that says, oh, maybe I'm doing something wrong? When you learn from reading politics or the news.

Speaker C: I think one of the things I've tried to do, you know, in a concerted effort in the last couple years is to make sure my sources. Look, I am, uh, I'm on the left side of things. Like many of us in San Francisco, I would describe myself as moderate liberal. And I think one of the things that I have recognized in the last couple of years is no matter who you are, you have to go out of your way and follow some of the top thinkers on the other side of the aisle. And I can tell you, if you look at who I follow on Twitter, I'm definitely following some conservative economists, some, some conservative politicians that you wouldn't think, uh, a liberal should be following. And I subscribe to people whose views I don't agree with. But I think there's some very clever views that don't often get put in the mainstream. So I feel like I have to make more of a concerted effort to do it because I don't want to just be listening to people that are down the middle. Moderate liberal, Ezra Klein esque people.

Speaker A: Yeah, yeah. I want to stay on, on the topic of you as a politician or you as an economist, uh, because when you graduated there was clearly a disdain for your first job at a think tank in Washington D.C. and then you lasted all of about a month or two at the Federal Reserve bank of New York. But I know and, uh, there's always an affinity towards Dartmouth. I almost went there as well. And you spend all of your time kind of thinking about your path and what you're going to be in the future being, uh, a politician or being in the political landscape. Somewhere. So tell us when you realized. Give us the two moments when you realized, number one, I don't want to be in politics. At least right now. Right, not right now. And then, number two, no, being an economist isn't me. I'm not going to go down that route.

Speaker C: Oh, wow. I actually, I do have those at the. My tongue. Because you're right, I did gravitate toward. I wouldn't say I was naturally like, oh, yes, I want to be a, um, politician. I always thought I would be more like a policy advisor or. I did think at one time very seriously about doing a PhD in economics and going. Going down the more public policy path, whether it was a professor or somebody like that. Uh, no. I did an internship at a. At a think tank in D.C. when I was in college. And part of the job was you were assigned topics to cover on the Hill. So I was the think tank. I was with. I was literally. This is going to sound very funny, but I was actually compiling a database of all the injuries and deaths related to marijuana usage. Because at time there was a organization, uh, that was paying this entity to compose this database. So I was going to a bunch of drug hearings on the Hill. And, you know, you're sitting in those hearings, and look, you're a college kid. You're excited about this. You're reading this and living and breathing it. And rational addiction policy is like something you're thinking about in Freakonomics. And then you sit in those hearings and you're like, oh, man, this is so disappointing. You're just like, they're doing it for the campaign ads, the 18 seats in the committee hearing room. And. And you're like, wow, only two of them are occupied. And nobody actually stays in that seat. They come, they give their speech, and then they leave. And I felt, look, I was a young college student, and I felt like I was learning a little bit about the incentives of the participants in the system. And I just, uh. I didn't think the hearings were that intellectually interesting. I didn't think there was a lot of honest engagement. So my conclusion was not much was really happening in that hearing room. I didn't know where it was happening, but it wasn't happening in public, and I didn't think it was. I didn't. Yeah, there wasn't a lot of interesting stuff happening there. And then, look, I went the more academic route. I was at the Fed. Look, I think that was pretty obvious when I was an intern there. There was a, uh, math class. We were learning some of the econometric techniques to derive some of the macro models, particularly something called the Kalman filter, which was used in these particular macro models. And I remember in week two of this ten week course just being lost. And you know, you're sitting there and you're looking at your peers and you're, you can see very visibly maybe a third of the group is lost like you, and then 2/3 they just seem to get it. And look, uh, it's not like I would ever put myself forward as some like math genius, but I was pretty much lost from day one or day two and I was like, wow, this feels pretty bad. And so you just realize that even if you were to go down that route, I'm sure there's people that make it work and fight it. It was just. You're like, wow, I'm not fighting to my strength at the moment. I genuinely thought that.

Speaker A: Sure. And then how did you uh, and take us through that, the pivot that you made then to get to, to really become a data scientist? Right. How did that come about? And I, I think I posed that question from a side of me that I work with a lot of university students at Wash U here in St. Louis and we have a lot of really gifted, talented students that are looking at the startup world or looking at technology. And as data scientists, non technical folks as well, they're looking at how do you pivot and how do you make that kind of change in your career. So how did that come about for you?

Speaker C: Yeah, so my first job out of college was, the reason I picked it was I was basically very indecisive. I was at a job where you were basically using those economics and data science skills which I had. And, and half the cohort would later go on to be econ researchers and econ professors and half the cohort would move into the business world, into the tech world. And many of us coming out of college, you're preserving optionality. So you know, I think that first job was very much an optionality, preserving one. And then, um, by the end of year one or year two, as it was becoming more and more obvious that you're running thousands of regressions, you have a good sense of what that type, the econ professorship route or the econ research route is going to look like. I think I'm somebody that learns better by process of elimination. So you kind of eliminate and then you turn to the other route. And I was lucky enough to have a college classmate starting at Salesforce. I saw that on LinkedIn. Uh, I said when I always wanted to try San Francisco and move to the west coast, try something new. And yeah, there I ended up flying out to San Francisco, interviewing with Salesforce. And I think that was my natural transition from the data world to entering the tech world and very quickly realizing how little I knew about SaaS and Salesforce while sitting in Salesforce's headquarters.

Speaker A: Yeah. What was that transition from? Cause I think you were in Boston at the time before you moved over to San Francisco, and your only real experience with the Bay area was, uh, a bike ride from Seattle to San Francisco. What was the change like going from first Dartmouth, because that wasn't that far removed, to then Boston to then this ultra liberal beacon of the west Coast.

Speaker C: I was fortunate in that a bunch of my, uh, kind of five closest friends, we all had this packed after college that we would all try to head out to the Bay Area quickly thereafter. So I remember coming out to the Bay Area. One of my best friends had just started a master's program at Berkeley, uh, in the engineering school. So I remember coming out realizing I knew 10 people or so. So it was, look, I was very lucky. It was an easy transition. I knew people. I can't say it was a, uh, hard one. I think culturally it was so interesting. It just opened your mind to, look, there's stereotypes of West Coasters versus East Coasters and what's important.

Speaker A: Absolutely.

Speaker C: I think there's a really interesting study that shows, like, when you ask people on the west coast to rank their happiness and statistically correlate that with factors, it tends to be like individuality and self actualization and what you're doing. And East Coasters are very much about, like, family and tradition. And it was just like, very real to see that.

Speaker B: Yeah, yeah.

Speaker A: Uh, and then all of a sudden you go from, like, what, uh, how did the opportunity at scale come about from Salesforce? It was, uh, another friend that can introduce you to someone. Was it just a growing obsession with mentor? What happened?

Speaker C: I wish it was either of those. No, no. I was sitting there. Look, I think after two years of that strategy group at Salesforce, I had learned a lot. He learned some of your. My peers who'd had that experience in consulting or banking. You got that skill set. You realize Salesforce is a pretty big company. They're doing fine. Marc Benioff is a great strategist. You don't need the junior analyst sitting on the 30th floor. I was looking for something new, and then, honestly, a recruiter just reached out from scale. I Think it was pure coincidence that we had just been going through a search for a, uh, head of portfolio operations. So basically someone to work with the companies. And scale is pretty quantitative by background. So I think some of the finalists were actually from my group at Salesforce. So I think it was just. People realized it was a group, uh, it was an interesting group. People that had experience with Go to Market and Pipeline. A recruiter reached out and I randomly took the interview. It was the only firm I spoke with. So, yeah, it was pretty much on a whim.

Speaker A: Yeah. Did you have a sense of what venture capital was really, or how did you end up preparing for this job?

Speaker C: Honestly, I didn't. I think by 2015, there was already a lot of blog. This was post the, uh, Bradfield blogging era. I think if someone in my position in 2007, 2008, there wouldn't have been much to read by this point. There was a lot to read, a lot of blog posts to read. Um, just started. It wasn't like I. I knew someone in my professional network who was in the industry, but I think it was just reading and seeing the blogs and trying to learn how they think. Scale had this test. We give it to all our associate candidates where they ask you to write a sample investment memo. And I. Or I think going to the. I don't know, one of the. Maybe it was Bessemer. I think they put some of their memos on their website and just learning how a venture capitalist thinks and writes. And yeah, it was a good learning experience.

Speaker A: Do you remember the company that you wrote the investment memo for?

Speaker C: Oh, God. I honestly do not. Okay. No, that's okay. No, I wish I could tell the story. I wrote the memo. I joined sales company. Honestly, no recollection of it whatsoever. But yeah, so I think it was just, you learn from reading, which is always my. My thing.

Speaker A: So we often talk about this again with the students that I work with, uh, at Washu. It's around cultivating curiosity. And curiosity, uh, is a word that. Bri, I don't know. If you gave us a dime for every time curiosity was mentioned on our podcast, we'd all be very rich at this point.

Speaker B: There's a remix roundup coming up that's going to be all about curiosity. Vic.

Speaker A: There you go. There you go. So from a cultivation, cultivating curiosity standpoint, what are the two or three resources that you would instill or like point students to right now? Because they're sick of hearing it from me. Where are the resources that you would send them to right now. And then if you could also think through and talk to us about the consideration of whether to specialize in one particular thing or to be a, uh, jack of all trades per se.

Speaker C: I think for my. One of the areas in economics I was always quite interested about was the kind of education literature, what can say statistically about what helps students learn. And I think at Dartmouth there was this initiative called habits of the Mind. What are the habits of the mind that make for a successful learner? And I feel like there's a researcher out of Penn, uh, Angela Duckworth, who talks a lot about grit. And I feel like in the conventional literature there's always this conversation around the grit component, the Angela Duckworth component, and the intelligence, the G factor. And there's these economists that try to run these regressions around. Is the G fact factor intelligence, more predictive of outcomes or is grit more predictive? And, uh, I don't know the literature well enough to offer an opinion. I know there's people that have PhDs that are paid to talk about this, but it's always interesting to me. I think there's a little bit of both. And I think curiosity. I think there's some very interesting papers around inculcating intrinsic motivation versus extrinsic motivation. And I think oftentimes in the literature, the importance of intrinsic motivation comes up. It's not just about rewards. It's about doing something that yourself are interested in. So I. I don't know what the data really suggests about the intelligence versus the grit factor, but I do very much subscribe to the. You have to yourself be interested in something. And I feel like there's a lot of. There's a lot of interesting blogging on how does somebody get interested in something? Is it interest comes first, and then because of the interest comes the effort, or is it more effort? First and excellence and effort leads to interest.

Speaker A: Yeah.

Speaker C: Uh, I wish I could say it's different than. It depends on the person, I think for sure. For myself, it's always, uh. I think I'm a competitive person. So I think when you're not working and you're not getting the right signals and things aren't going well, the interest is harder. But I don't really know. Look, I. As I said at the beginning, I like to read perspectives that I don't necessarily disagree with. And one of the most shocking books I think I ever read was an economist at George Mason who basically suggests that I forget the name of the book, but it talks about how quickly we all Forget and how. Basically, I think if you tested a, uh, graduating high, uh, school senior and then retested them four years after college, it's scary how little the knowledge and the improvement on the test score would show. I don't know. I really don't know. I think it's a fascinating subject. I don't know. What do you think?

Speaker A: I always. So this goes to, uh, something that you actually pointed to in the questionnaire, in the pre recording questionnaire that you filled out. And it was really around admiring people that follow their passions rather than societal expectations, around where they should be. Right. The shoulds and the codes and the woods. Anyone with a therapist and thank you Jason again, will tell you to admonish or quell or mitigate the shoulds and the coulds and the wood thinking and just be in the moment and continue to move down whatever path you're going down. And um, so for me, the quest for curiosity or continuing to be curious about things, I think you're kind of right. Everyone has that certain passion or that certain, you know, set of subjects that they gravitate to or things, uh, that they gravitate to. Um, and it's up to you, the individual, to see that passion for what it is and encourage it rather than quell it. And so I think that a lot of people, um, might continue to be curious, but then they use the energy that they would normally use being curious when they were younger to just doing work, however it manifests. Right. Uh, later on. The great thing about Venture is that it literally serves as this catalyst for continuing to be curious. Right. I think that's why so many of our guests on the show have that thread in them. Is it that curiosity threat in them is that Venture forces you to constantly, uh, even if you're vertically focused or industry or technically focused, it still measures you by how curious you want to be and how out of the box that you're thinking. So I think we, we're fortunate in that we come to that conclusion. Right. We've come down this path where the curiosity naturally melds itself. But with college students, at least when I talk to them, it's like, don't just ask the question why More than not. Right? That's how I cultivate curiosity in my friends and in any relationship is asking why. It's why Bri and I exist on this podcast. Right? It's asking questions because that's. That satiates that curiosity in us. Uh, I don't know. Bri, what do you think?

Speaker B: As I reflect on what Both of you have said, I'll go back to kind of, Jeremy, when I was thinking about your grit versus Intellectual learning, I was thinking about video games and just how they have really tapped into that. That ability to get you to the next level without you giving up because they give you just enough learning and so you get into that flow state. I can remember as a kid, you'll play video games even as an adult for like, hours. There were times I had to cut myself off from the Sims in college because I think I played it for 72 hours straight. I'm like, I haven't slept in 72 hours because my Sim's building a nightclub. What kind of craziness is that? But I think they. That technology has tapped into that, not just video games, because social media and all of these other apps have realized we now have a phone in our hand 247 and they can gamify those things and they can tap into. What you were just saying is that how can I have a low effort, I. E. Take a picture of my coffee and post it and get a lot of Reward for that. 56 likes or whatever. Right? So I almost feel like technology is hacked into what you have said and in a way created a little bit of a monster. Which brings me back to a question that I had for you, Jeremy, when you were doing your bike ride, how much of that was assisted by technology? And then because it was 2008,

Speaker C: fascinating to think about. That was the last summer before the iPhone came out. If we literally, we all put chalk in our pockets and the expectation was when there was a big turn, you chalked it for the sake of the group. Because unlike, um, now, you didn't mount your phone, you didn't mount your gps. You didn't have gps. In fact, in large portions of the country, when you're out in the cornfields in Ohio, you don't even have cell phone service. So it's funny to reflect on the fact that summer might have literally been the last time when you didn't have the map. And look, uh, uh, from a policy perspective, I think what the Surgeon General is talking about with human interaction, loneliness. I think a little bit about what Robert Putnam with Bowling Alone talks about. That was the last year before this phone phenomenon really came about. So it is funny to think, yeah, the phone was not a big part of that experience, but because we didn't really have a lot of cell phone service throughout the summer, which is very different. It's very different than it would. Would have been today, for sure.

Speaker A: Yeah.

Speaker C: Do you feel like.

Speaker A: So this is a question that we actually have talked about, uh, multiple times. It just so happens to be the age range that we're in. Right. But we all remember what it was like to have rotary phones, and we all remember what the first cell phone felt like. And then consequently, like, what smartphones are. Right. And I honestly feel like kids these days, I'm gonna really make myself feel old right now. But like, kids these days, if you put. And we talked about this before we press record. But all of the. All of the products and services that OpenAI and Google I O. And when I say shit in a good way, great, uh, all these great products and services that came out, I feel like that kind of goes on deaf ears with the current generation of kids with smartphones and all this technology at their fingertips. The irony is that they don't really seek or aren't curious to utilize all of these great products and services that are out there. And instead they're glued to TikTok and Snapchat and whatever else. Yeah. Is there like a. Do we need to be teaching our students how to utilize this? Like, who does this?

Speaker B: We're punishing them, Vic. We're telling them they can't use it because they're cheating, which I think is the wrong approach. Sorry, Jeremy, it's your.

Speaker C: Yeah, I was just. No, Brie, to your point, I was reading. I was just reading something last night. That being a teacher this year must be really weird because the concept of homework, the concept of students writing papers has more or less gone out the window as of last night. You can point your phone at a, uh, math problem and get an answer. I think we're at, um, the start of something very different.

Speaker A: Yeah.

Speaker C: And the problem is that. And I think this is where a lot of the commentary is a little bit circular and doesn't really resolve itself, which is. So what comes next? What do you do as a student? What do you do as a teacher with all this new technology? I don't really know what the answer is, but I am seeing every single week really interesting kind of these. What can you do with an AI tutor in your pocket for free? What does that business model look like? What does that mean for the practice of education? I do go back to the fact. Look, uh, one of my best friends just moved out of the city, up to Sebastopol area in. In Sonoma county, and his wife is a teacher and director of admissions at a school there that is very anti technology. Like, they don't allow the Kids up until the eighth grade to use the phone. And I feel like there's always been this very odd phenomenon of the quote unquote tech elite. And sure, how they're the schools that teach their children, teach them how to use technology, when to use it, when not to use it, what are the social norms around that, that somehow, and somehow that discussion misses the long critical mass of many other kids. So there is a lot to unpack on that subject.

Speaker A: Yeah, uh, uh, sorry. I'm in the camp where you see all this radical adoption of generative AI and I feel like our schools, our teachers, the way we teach, needs to somehow match that curve in terms of transformative ways, uh, of teaching. And instead of, I don't think the answer is, look, let's shelter our kids from screens and phones until they're 15. Right. Or something extreme like that. I really do think we're coming into this stage where if all of our educations were about textbooks and the classroom as the epicenter of being an intellectual learning, then that is no longer the case. And we need to look at teaching what we learned in college, which is basically to learn for yourself at a very early stage. Right. It's to utilize all these great tools to learn the stuff that you're going to be tested on or the stuff that you need to know. And so it's, and this is, I'm gonna puke after I say this, but it's like the co pilot of teaching where our physical teachers need to become co pilots and assistants in helping our students achieve that ability to learn for themselves. Uh, that's where I think education's going.

Speaker B: More Socratic, definitely.

Speaker A: Yes, much more Socratic.

Speaker B: I was recently listening to a history book on Audible in the car and I was asking ChatGPT to create the visual images to go along with those historical moments. And it did. It was just so cool. And I'm like, why do teachers not use it that way?

Speaker C: Yeah, I, I just saw, I met a company today who is basically going to be selling a tutoring assist. I just think from an education perspective at Passover Seder a few weeks back, my, my aunt was there. She's a teacher, she's a public school teacher in New Jersey. And she was just like, you can't imagine how much change is about to come in that space. The concept of written textbooks, the concept gone, homework problems, the concept of long essays, uh, it's going to be tirely entirely new. And often things, oftentimes things are more sequential or phase based. And I feel like this is a real, this is a real more than a fate. This is a real phase change. This is not just sequential linear change.

Speaker B: Yeah, I feel like we're going to be turning students and I'm not even joking about this. We're going to be transforming them into like miniature documentarians in a way. Like they're going to be documenting our future history because they've been given all the tools to document it. They're going to have VR. They can document VR. They could document things ways we can't. So if we teach them the tools correctly and we give them access to these tools, we could have a really cool future. But right now we're in this weird, bizarre transition phase.

Speaker A: It's pretty easy to feel bogged out in technology. And uh, one of the things that you try and do is to step away from technology whenever possible to rest and recharge. And I think you mentioned that you love to mentally get yourself out of the tech space, but also you're maybe the happiest you are when you're on a bike or hiking or walking just in nature. And you mentioned something about having an introverted side, but I'm wondering, do you consider yourself a, uh, full fledged introvert or are you like me, where you've got your extrovert time and then you need to pull back and be introverted.

Speaker C: Look, I've taken, I think in my first job they made you take that personality survey and nicely scored right at the middle between introvert and extrovert.

Speaker A: Okay.

Speaker C: I think, look, I think so. No, I'm not totally one way or the other but I think relative to more folks in this industry, uh, I think I do enjoy meeting people, I enjoy learning from people. But uh, one thing I've realized, I need this quiet time where people go away, slack stops, pinging, the emails stop flying. And uh, unfortunately that only happens later, later in the day or on the weekends. And I feel like the decision making part of the job for me tends to happen in those quiet moments when there's, I just, I look, I think that my younger self would be, would find it hysterical. I'm in a job with as much people interaction venture ecosystem not because I don't enjoy it, it's just that uh, I think on my, I think my best when I have a little bit of peace and quiet and I sometimes I feel like I haven't found yet in my career the best way to balance the constant hustle, bustle, meeting people, catching up with people, going to the event and then having to need that moment of just quiet and think time. So for me, it's being on your bike, being in the pool, just having that moment to think. And I feel like that's what I'm trying to figure out right now. How do you just be more intentional about scheduling that and making that happen?

Speaker B: Ah. What was your Myers Briggs type? Do you remember?

Speaker C: Oh, man. Okay, if I tell you that, people are gonna judge me for knowing it. And half the people are gonna say,

Speaker A: no one's gonna judge you for knowing it.

Speaker B: No one's judging you anyway. Okay.

Speaker C: I think I do remember it, because my first job, they made us take it. I was introverted. Istj. I don't remember what the other categories mean, so I was introvert.

Speaker B: Sensing, thinking, judging.

Speaker A: Yeah.

Speaker B: Wow.

Speaker A: Bri, this is, uh, as you can tell, Jeremy, this is Bree's bread and butter.

Speaker C: Bree, you tell me what that means.

Speaker A: Can we psychoanalyze them now?

Speaker B: Sure. ISTJs are you're very good at categorizing things. Would you say that is true?

Speaker C: Yes, I do. That's how I think about everything I try.

Speaker B: Yes, that would be your superpower. Would be your ability to categorize, which is my secondary superpower. So I also have that superpower. It's funny, because some people who that's not their superpower don't even understand what we mean. Jeremy.

Speaker C: I don't know.

Speaker A: I don't know. What are you talking about?

Speaker B: Yeah, he likes spreadsheets, I'm assuming. Um, of course he does.

Speaker C: Isn't, you know, calm, quiet.

Speaker A: Right?

Speaker C: Keep your mouth shut. Let me run my spreadsheet. Let me think.

Speaker B: Yeah, but intjs, who are the end versions of you hate spreadsheets. So many will say, oh, that's a J thing, or whatever. No, because they're TI's, like, uh, us, the introverted thinkers, we love spreadsheets.

Speaker A: Look, I. I'm okay with a spreadsheet. I don't avoid them like the plague. But I. I can know I can find my way around a spreadsheet. But it's easy in this day and age, particularly around Twitter, the Twitterverse, and like, VC Twitter, the constant stream of events that we have, the speaking engagements that we have, it's clear that we like to embrace the extrovert, and we prop them up all the time. You mentioned a great book by Susan Cain called Quiet, and in it, and I've only read the Cliff Notes, so I'm just going to cop to that. But in it, it sounds like she subscribes to the idea that we really undervalue the introvert in society. And by the way, I think we undervalue the introvert that the introvert side of being a venture capitalist too often. And, uh, Jeremy, you could probably talk to this more than myself, but being in the boardroom, we almost always de facto defer to the loudest voice.

Speaker C: Yes.

Speaker A: And this has been my experience, but all of the best venture capitalists that I've ever known, that have ever been on the show, that have ever been, um, mentors to me, etcetera, they've always talked the least and asked the best questions and been the most active listeners. Uh, what's your take on that, Jeremy,

Speaker C: given that you are what you are, and I am probably a little bit more introvert than extrovert? I think Susan Cain's perspective is basically, there's a set of norms for how extroverts are supposed to exist in the world, how extroverts are supposed to lead. Uh, we accept that set of norms because it's all we know. And I think Susan Cain, I forget it's been a while. I think she gives an example of a professor who, like, wins the award for the best teacher because his professor is able to empathize and listen to the students and perceive in a way that, uh, a bigger talker wouldn't. And I think the introvert also has an advantage. I think Susan Cain also talks about it. I think it's that there's a French word called flaneur, which is someone who can exist both as an observer, as a scene, and a participant in the scene. Some of the partners that I admire the most and that I've learned from, they seem to somehow both exist in the boardroom and exist in a plane above the boardroom, looking down on themselves, looking down at other. The participants. I feel like, uh, that's a level of thinking and existence that I always admire, that people can do that. And, yeah, sometimes I feel like everyone's just making it up as you go along. And I think for me, as an introvert, you're just. You're just trying to figure it out what, uh, kind of works for you.

Speaker A: Yeah. You and I both subscribe to being and propping up analysts at all times. Like when I was a young analyst at SK Telecom Ventures, I was proud to call myself an analyst. Like, I. I loved learning about everything, listening to everybody, being the dumbest person at the table. And that's how I felt like I got good at. At, uh, thinking like a venture capitalist was being that analyst and being the analyst role. So I Know, I knew I was going to like you before we started this podcast because I felt like we had that analyst mentality. The other thing that you have though, and it's very evident in doing background research on you, is that you are incredibly humble and you are very quick to give, to heap praise on your colleagues for the work that you jointly did. And I think that's something that, from a team perspective, in a world of a lot of lone wolves, that, that kind of goes very noticed when you end up doing the research. And Bri and I have done this now for 32, 33 episodes now. It's a really interesting approach that you have. I'm wondering how does, how did that mentality and how does, you know, you building that kind of camaraderie with your team really help you and Scale take on the challenge that is AI uh and generative AI uh in this space?

Speaker C: That's a hard question.

Speaker A: No softballs here, Jeremy. No softballs.

Speaker C: Look, I think one thing that I've learned and something I subscribe to is that, and I think scale does. I think that's one of our superpowers as a firm, to be honest. If you look at the fact of, uh, where do our successful deals come from? Many of our most successful deals came, were introduced to a person at Scale who then handed the opportunity to someone else on the team who thought, quote, they knew about the. Knew more about the subject than so good.

Speaker A: Such a good point.

Speaker C: And I think whenever I'm interviewing associates or principals and they always say, what's the look? Every firm has its own culture. I think the culture of Scale is the team and not the lone wolf. And who's uh, to say it's right or wrong or you can't be successful the other way. So I, I think it's. I think I probably just naturally fit into that culture because that's what the culture was and that's probably who I am. I think from an AI perspective, what you really have to. What's so important here. Because if you subscribe to the fact that, look, in enterprise software investing, you've really had three or four big paradigm shifts. You had SaaS, you had mobile, you had Cloud, and now you have AI. Uh, in the latter years of SaaS, the person that has seen the last eight or nine years of that paradigm is particularly, well, advantage because there's a greater correlation between year 10 and year 8. But if you subscribe to the fact that you enter this new wave, you have to be a little bit cautious and not overconfident. Of extrapolating from the past and therefore what that practically means to your question about team is that uh, the associate or the analyst or the principal that's new to venture, maybe had a related job or related work experience, might know something that you don't know. The pound your chest. I know everything can really screw you up. I find it astounding how much empirical evidence there is that when somebody's fame and celebrity goes up, decision making power and their probability of right being right tends to go down.

Speaker A: Yeah.

Speaker B: Mhm.

Speaker C: And look, I think there are. If you subscribe to the fact that at the end of the day you're either you either make good decisions or you make bad decisions. And you win in this job if you make good decisions and you lose if you make bad decisions. Your habit of the mind should be to pursue a strategy that optimizes the probability that you're going to make the best decision. Which probably means putting the most talented people around you, listening to them, not always agreeing with them, but empowering them to speak up. So I think one thing people would say is I learned under a partner who didn't distinguish between job titles. Whether you were associate or a principal or a senior associate. I think that was a philosophy that was great for me and I subscribed to that. Which partner is uh, that, uh, Andy Vitus. Uh, whether you were an associate or a senior associate. His point was you try the product, you write the memo, you think, talk to smart people and therefore it becomes a question of who knows the market the best. And it's not. Oh yeah, the principal automatically knows it the best or is smarter than the person with the title senior associate. And I know you guys know my teammate Alex Nihenke. Ah, look, he very much subscribes to that philosophy as well. And I think you learn a lot from that. That his team player dynamic as well.

Speaker A: Yeah, yeah.

Speaker B: Alex had a humbling experience from us when we gave him a pair of hot cookie underwear to wear at his pool.

Speaker C: Is this a hot cookie brief?

Speaker A: Is this male underwear?

Speaker C: Okay.

Speaker A: I feel like our, our as we've gotten more mainstream, Jeremy, our gifts and VC unboxing have had to maybe tone down. But uh, honestly,

Speaker C: now I'm on the alert for what's going to be in my. But no.

Speaker A: So Bri has a good point there. Maybe we need to bring back the hot cookie and other kind of not, uh, gag gifts, but questionable appropriateness. Yes. So speaking of your partnership and about scale, scale has to my knowledge and in my experience has been really at the leading edge of thought leadership from a. Taking a perspective and planting a flag uh, in the ground in terms of what your perspective is from a firm, firm wide look and you've done so in Generative AI in the, in the building and development of the Generative AI Index and the creation of your own scale chatbot. I have beef with your chatbot by the way. I was asking can you give me the link to the Generative AI index? And it said I can't provide you the link.

Speaker C: Oh, we're gonna figure that out tomorrow.

Speaker A: It told me to go to the website which I was already on but that's okay. I was able to find it. Everything's and, and by the way for the listeners and viewers out there, whether you're a vc, uh, a startup founder, Scale has always had a lot of resources and tools free and open for the use of founders for a long time. They've just now added another layer of gen and used for the Generative AI Index in 2021, 2022. So it's been around. This isn't new hat just knowing that can you share how the team came together to build that perspective and then just with all of the things and we don't. It's such a broad topic but can you jump into like the insights and the trends that you are most, most top of mind for you around Generative AI right now, particularly as Google just released a uh, series of products and Updates to Gemini OpenAI with their ChatGPT4O Claude 3 the Perplexity Gang. Like there's just so much going on.

Speaker C: Yeah, no it's, it's, it's terrifying how much is going on. Yeah. How, how quickly you have to have to internalize, you know, understand the impact of what happened last night.

Speaker A: Yeah.

Speaker C: Props to, props to Ethan Malik uh, at Penn for being the first hot take blog. I think.

Speaker B: Yeah.

Speaker C: Like 11:50pm I mean talk about, talk about people that are curious and passionate. Like that was uh, that was impressive the timeliness there. Look, I think you asked about the Scale team, the Scale perspective on Generative AI. Look, there's seven partners at Scale. Four of us probably do application level software, three do infrastructure. So this is a theme that crosses everybody I think on the app side and that's where I spend most of my time. Uh, I think the big question is very much this so called ChatGPT wrapper question and I, I think that we have done ourselves a disservice by degrading the term wrapper. I think that it is a Very fine line. A much finer line than we want to admit. I think when a VC writes a blog post about what they're looking for in AI, top of mind is always proprietary data we don't want.

Speaker A: But look,

Speaker C: I would say to those people, on what day, like on day one of the company you were a rapper like, and you go back to SaaS, day one of of your SaaS company you were on day, uh, 36, you were a rapper on, on day 700, you're probably a rapper. So defensibility comes in different formats, it comes in different ways, it comes at different times. Sure. I do think, look, there are obvious examples on the app side of companies that haven't built that defensibilities and have been washed over by the OpenAI model. No doubt about it. But I think the thing that I try to think through in every category, in every deal, you are trying to hypothesize what are the future workflows, what are the future data gathering opportunities from the user, what are future integrations to other products that can give you accessibility. So to all those people on Twitter that say, I don't do chatgpt wrappers, my comment would be, okay, then what about all the SaaS companies that started as a rapper themselves? So look, it's a very complex question, but uh, you have to. I don't think it's as simple as saying, oh, it's just a rapper. Oh, it's not a rapper. Because the truth of the matter is the winners will probably all look like rappers on day one. And losers who get swamped with OpenAI will have gotten swamped before they had the opportunity to build something else. So I think on the app side we are very much thinking through what can somebody build on top of a foundation model. And no matter what industry is construction or healthcare or law, I feel like it's the same set of questions every time.

Speaker B: Yeah, speaking of, uh, rappers Kendrick Lamar or Drake on the last Winner Loser Rap battle. Sorry I couldn't help you.

Speaker A: I think Childish can't be and have the last laugh because you've got Donald Glover now working with Google on a number of different projects.

Speaker B: Way to bring it back, Vic.

Speaker A: Yeah, no, I wanted to keep it there because here's the counter argument. I subscribe to the 11 risks that Tomas from Redpoint now theory, right underlined. And everyone looks if you were investing in 2008, which again dating myself, but I was, you saw platform risk rear its ugly head. If you were trying to build on top of Facebook or on top of iOS, right. And yeah, I subscribe. Jeremy. Look, a lot of times you're building on these broader platforms and there's inherent platform risk to doing that. But then you see something like today with Google I O and this is unfair because you've been working all day and so you probably haven't seen it.

Speaker C: I saw the demo day, I saw that Google I O. It was awesome.

Speaker A: It was awesome. But the over the revamp that they're really giving search, for instance, is a really interesting position. Right. Where they're integrating Gemini into their search results. And uh, it's fair to say that it's going to be relatively top billing in terms of where in the search results this comes about. And they're essentially paraphrasing or aggregating content that comes from other websites directly on their site within the search result, which I think a lot of people have cried bloody murder and they're like advertising and driving clicks and traffic and this is going to break everything. It's fair to give that counter argument to say there's this fear that, that we've never had a technology that's been adopted so widely so quickly that's really been concentrated to OpenAI and Google. And you can make a case for anthropic and you can make a case for xai, uh, with the data sources that they have. But what does it mean? And so this is leaning into the question of about when you look at startups now in this app application layer on top of ChatGPT, or how do you guide them to not only be aware of the platform risk, but then to mitigate that platform risk.

Speaker B: Totally.

Speaker C: So I think maybe we'll take a specific example. Look, I agree with you. I was thinking more about B2B applications. I think search is whole different beast. I think if you wanted to bet a bet against Google, there are several options in the venture market available to take that bet. Sure. Uh, you can take that bet if you want to. Let's take the example of a B2B application. Yeah. In medical coding, health, uh, prescribing or litigation or the lawyer uses. So think about what the lawyer, what a lawyer uses.

Speaker A: Yeah.

Speaker C: The lawyer's sources for citations are legal cases now at the moment. And look, you could say in 10 years from now the foundation model will have access to all the cases and all of that. But at the moment, these there, uh, these are private data sources curated by businesses like Thomson Reuters, Westlaw, Lexis. In the old world, before these, before ChatGPT, there were people, there were lawyers. Who graduated from law school and they're sitting in Iowa, literally summarizing cases and result of their labor went behind a firewall. It was the ownership of Lexis or one of the case text. And I think in those business models where there was some data asset that was simply not available to the public advantage to that source. Now, in the financial world, you've got companies like FactSet and Bloomberg, and they also have propriety. They have data that nobody else has. So I think those are some fruitful areas. And then I'll make the weaker version of my argument, which is, I think if the strong version is you need a differential data source and those. Take those two examples. I think the weaker version of that would be there are vertical specific integrations and applications limitations that a foundation model company will not do. Let's take the medical scribing example. Look, you can divide the EHR market into two groups of companies. There's the EHR vendors serving the hospitals and their EHR vendors serving outside of the hospitals. If you want to build a company serving doctors outside of the hospitals, you've got a long tail of 10 to 20 different EMRs that have critical mass in that segment at the moment. I don't see in the next five years OpenAI having direct business integrations with the long tail of those 10 to 20 EMR companies. That would probably be the weaker form of the argument that maybe integrations are some form of defensibility against just the open AIs of the world doing so.

Speaker B: Yeah. Okay, we have to move on to the last. The boxes, the group of boxes. Fidelity, five questions in the last box. Because we are coming up on our time, so I'm going to move us along very quickly. Vic, we can talk about AI all night, like.

Speaker A: I know, I know.

Speaker B: Trust me. I've got about 30 more questions for

Speaker A: Jeremy, but I was gonna jump into Solvi, I don't know where.

Speaker B: All right.

Speaker A: Yeah, we. We had plenty of things. Yeah.

Speaker B: So let's open. Let's do VC unboxing number two, which we should have done way earlier, but we're doing it now.

Speaker A: So look, going with the exercise portion

Speaker C: of this, is the box marked Shine?

Speaker B: Yes. Start with Shine. Start with shine.

Speaker A: Oh, wait, no shot. Is this shine?

Speaker B: Yeah, there's gonna be three. He's just gonna open those three together. So he'll just have to open them.

Speaker A: Oh, yeah. Okay. Shine Adventure weekend warrior.

Speaker C: All right. Oh, I got a nice hat to keep me warm.

Speaker B: So it's a hat with actually a light on it, so you can actually Have a headlamp. It's a headlamp in a beanie. So when you go biking, can see and keep your head warm.

Speaker C: Oh, this is great. Wow. Okay.

Speaker B: We actually. We used one during a blackout we had recently.

Speaker C: All right, props to you. That was a good pick. All right, what else?

Speaker B: All right, next one.

Speaker C: Um, you.

Speaker A: This is Weekend Warrior.

Speaker C: This is a Weekend Warrior. Boxes.

Speaker A: Yeah. Okay.

Speaker C: Is this a punch show? Um, a sleeping bag.

Speaker B: It's an emergency sleeping bag.

Speaker A: Yeah.

Speaker C: Wow.

Speaker B: Yes.

Speaker A: Which would have been really helpful in 2008 when you were riding a bike cross country. But Bri and I really felt this mentality of yours to step away, recharge the batteries in nature, and also embrace other things like meditation and whatnot. You're going to need some stuff in the wilderness. And so we really wanted to.

Speaker C: You guys have me well prepared.

Speaker B: His bots will be working for him while he's out on a bike ride, so he'll be productive while enjoying a

Speaker C: National Geographic 100 hikes of a lifetime. 100 bike rides of a lifetime.

Speaker B: All right. Yes.

Speaker C: Good stuff.

Speaker B: So while we're on the topic, what's your favorite bike ride and your favorite hike?

Speaker C: Oh, man. I think the favorite bike ride of my life was riding Washington Pass in. In North Cascades national park, which is in central Washington. It's an amazing. It's an amazing pass. Yeah. I, uh, think around the Bay Area. I think the riding in Marin is. Is awesome. And there's a loop to do up there, the Marin Cheese factory loop, the hills. So, yeah. Oh, this is great. And the hikes, I feel like there's an amazing if, uh, people. I think one of the best hikes I ever did in California. It's embarrassingly easy to get to. It's the stretch of the PCT right at the top of Sonora Pass. Like, I think for the people that crew hike the PCT, I think the nicest 10 mile section is literally you drive to the top of Sonora Pass, you park your car, and you, like, hike for five miles.

Speaker B: It's nice.

Speaker A: I'm in it.

Speaker B: Excellent. We always end our show with Fidelity 5 questions. Are you ready to play the Fidelity 5 questions? Sure. All right.

Speaker A: Also, he said it trepidly.

Speaker C: I'm like, oh, yeah. I'm like, I don't know what those are gonna be.

Speaker B: Don't worry. They're very easy. Okay. First question is always, what is your favorite go to karaoke song?

Speaker C: I will survive. I feel like that's the.

Speaker B: Yeah.

Speaker C: Uh, I feel like that's a good.

Speaker A: Okay. All Right. I was not expecting that. But I like it, Jerry. I love it. I like it. I'm here for it. Uh, the second question in Fidelity 5 is if you could invest in any fictional startup from a movie, TV show, or book, what would it be? And I should say, not just startup, but it could be a technology. Whether it's the Precogs and Minority Report. My favorite is the hoverboard. Everyone's got something.

Speaker C: If I worked in the private equity world, I might say Dunder Mifflin. I would say the management team. There's just so much room to professionalize the management team.

Speaker A: Look at this. SaaS, vertical integrations. Always thinking about them. Jeremy, that was nice.

Speaker B: Okay? You could do it all over again. Would you rather be an investor or a builder?

Speaker C: Haven't been a builder yet, so who's, uh, to say? Yeah, I don't know.

Speaker A: You heard it here first. He said yet, and we didn't get to this, but to each their own path. Five to ten years, quick nod or nix on maybe becoming a builder.

Speaker C: Maybe. Honestly, I've been loving. I. I. Look, I think my personality, that analyst personality does probably lend itself well to this investing thing, so I. I honestly enjoy it immensely. Yeah. No, no immediate or intermediate plans.

Speaker A: Yeah. All right. Question number four. Brady. Want to go?

Speaker B: What movie best fits the future of the human race? Wall E. We've all degenerated into an obese state due to anti gravity in the metaverse. Avatar. We're dominated by this quest for resources, new worlds walking around in Avatar bodies. Or the Matrix, where we're all in a simulation.

Speaker C: What was the second one?

Speaker B: Oh, Avatar.

Speaker C: Oh, Avatar. Probably Avatar. Like, the first one is just so negative. And, uh, we're just in the simulation. Sounds like a freshman midnight conversation. Yeah, man. We're just. It's all a simulator.

Speaker A: The. Dude, I love it. I love it. All right, the final question. Fidelity 5. What is the one deal you passed on that you wish you hadn't?

Speaker C: That's obvious. When I was an associate, we looked at figma. We passed on it at the Series B. Uh, and fun fact, I start my January 1st every year looking back at that data room, trying to see what was the hidden signal that we missed at the Series B. It was seven weeks into monetization and was clearly the worst decision that, that I've been a part of.

Speaker B: Oh, wow. Thank you. Thank you.

Speaker A: That was.

Speaker B: Thank you for that honesty.

Speaker A: Yeah, incredible honesty. And thank you for playing Fidelity five questions with Brie and I, uh, as. As a symbol of our thanks we have one more box for you to open. Uh, so open that now.

Speaker C: Box within a box.

Speaker A: Um, we'll see how it goes.

Speaker B: Here we go.

Speaker C: Oh, the VC starter kit.

Speaker B: Yes. Yes.

Speaker A: Uh, oh, yeah.

Speaker C: Awesome.

Speaker A: So on the back is our logo, but what's. What does it say on the front?

Speaker C: It says Adventure Capitalist. Oh, yeah, that's good.

Speaker A: I like that.

Speaker C: Uh, all right, did you guys come up with that, or did ChatGPT come up with that?

Speaker B: That was all Vic.

Speaker A: All right, all us. All us, yeah. Absolutely.

Speaker B: Okay. We know our time is up with you, Jeremy, so we always ask our guests to toast us out. It can be to a startup, a friend, family, anyone you want. It's your toast,

Speaker A: Honestly.

Speaker C: Uh, to a happy and healthy remainder of 2024. To everyone.

Speaker B: It's a good one. Thank you.

Speaker A: That's a good one.

Speaker B: Here.

Speaker A: Cheers.

Speaker B: Thanks for cozying up and listening to another episode of Drinks with a vc. We are so grateful for our listener support. Feel free to reach out and add any of your questions to the comment section. If you have an idea for a guest or have some feedback, reach out to us on LinkedIn.

Speaker A: If you liked that last episode, be sure to check out our others featuring VCs from Lightspeed, Bessemer, Hannah Gray, BTV and Norwest. As always, don't forget to like and subscribe.

Speaker C: Cheers.