#249 David Haber: a16z General Partner on Living in the Grey, Building Compounding Advantage and Goldman Sachs Acquisition

Hi, I'm Vittet, the founder and host of this podcast, The High Flies. And I'm David Heber, a general partner at Indri's in Horowitz. David, I'm really excited to do this. You've done a few interviews over the years that I've really enjoyed. I'd be curious if I could promise you one thing to make this your favorite interview. What would that be? Well, I think we're going to hopefully cover a lot of ground. So I'm happy to chat through my story, my work, my personal life, wherever you want to take it. I think that would be, that would be a lot of fun. What if we could reimagine the traditional notion of a high flyer? Hey friends, welcome back, or welcome to The High Flies Podcast, where we do reimagine a high flyer, showcase the brightest and most relatable role models and companies and their journey from sunrise to today. As one of the premier products, inaccurately center the lineup, providing on-demand intelligence to help you be one person better every single day. Homeyhost, Vittetagol, and let's have some fun. Our listeners have called this podcast as a meticulously researched biography unveiling the extraordinary lives and decisions of the most remarkable individuals and companies from around the world. We hope you're enjoying our catalog of 200+ episodes, since we launched in 2020 with many of our guests appearing in rare public interviews. It's now time to explore your curiosity. Please enjoy. Let's set some fun facts to get us going. Where we born and where do you live now? I was born in Chulivista, California, which is South San Diego, about 10 minutes from Mexico, and I now live on the upper west side of Manhattan and New York City. And what was your fish job and what do you do now? I had a bunch of little jobs growing up basically to make gas money. I sold tacos at Friday night football games. I went to a really big public high school where we had a few thousand people show up for Friday night football games and had a side hustle selling tacos there. And very analogous, I now do venture capital here at Injuries and Horowitz. Yeah, I mean tacos in venture capital, right? I mean, there's some similarities there. And David, as you know, the purpose of this show is to reimagine the concept of a high flyer. Is there a person who you feel hasn't got the recognition that is Earth? Oh, man, there's so many. I think one of my favorite terms is this notion of what I call safe hands. And it's just this feeling of anytime you can. It's the best feeling in the world as a founder, as a manager, as a CEO, you can give a project, a division, a chunk of the business to somebody that it's going to get done with quality on time. And you don't need to chase it. It doesn't mean that person is not going to find challenges, but they're going to communicate, they're going to be entrepreneurial. And the person that I named this after, that sort of attribute, it was a guy named Eddie Seryl. He was one of the first hires that we made at my last company, Bond Street. I think technically his title was VP of business development, and he had this gravitational pull where he ended up running sales and BD and marketing and HR and finance. He really was running half the business. He's an incredible operator. He went on to go open the Stripe New York office, built Stripe Capital. I think played Chief Risk Officer for Stripe for a number of years. And so their senior leadership keeps placing him in some of the tougher challenges within that company. And I think now Stripe New York is probably almost 1,000 people. But he's an amazing operator that kind of lives behind the scenes. But I think it's really been foundational, certainly to any success. We had at Bond Street, and I think in every organization that he's a part of. Incredibly, he sounds great. And I love those operators who don't care about the spotlight. They just do the work. And then they eventually get the spotlight for the work they've done in the future. So that's a really nice call out. Let's one back the clock and go to your Sunrise as I call it. Your childhood, your upbringing. You mentioned San Diego. What are your memories of growing up there? I don't know. Family played a big role and culture played a big role. Is that right? Yeah. I grew up in a kind of funny Mexican Jewish community in South San Diego. My father was from Tejona, Mexico. My mom's from Los Angeles. But he was born in Tejona by way of Romania. My grandmother was born in Romania, survived the Holocaust, moved to Israel, got married when she was 16. And then couldn't get into the United States because of immigration quotas. And her brother-in-law had started a business in Nicaragua of all places. And so I ended up moving from Israel to Nicaragua. No money, no Spanish. My aunt was born in Nicaragua. And then they tried to get as close as they could to the United States, which is Tejona, which is on the border with San Diego. And so again, I grew up with the offspring of the Tejona Mexican Jewish community. And I think that sort of played a role in that. It was always like a dual identity in some ways, living in between both cultures. And it was funny. I mean, it was funny, that big public high school that I mentioned that I sold tacos at. There were probably 30 Jewish kids at a school of 3,000. And all of whom basically were Mexican. And so many people that hadn't really like traveled much thought that all Jews were Mexican. I was like, no, this is not a normal thing. But I was very lucky. I had, yeah, amazing parents. My mom growing up was a public school teacher. And I was always very involved in my education. I have two younger siblings. Middle sister, who's three years younger and a younger brother, Michael, who's eight years younger than I am. And my dad worked in the retail business in Mexico growing up. And in the duty free business into my teenage years. Yeah, but I think having parents that were just very focused on my education, that were very present, that kind of pushed me, frankly helped me accountable. But I needed to be, definitely had a really big impact on certainly any academic success I had. But also I think in kind of building self-confidence, which I think has been a, played a very formative role in my life, for sure. You talk about living between worlds culturally, geographically, Jewish, Mexican, American. I'm curious, where did you feel most comfortable in those identities? Is there one that you go back to that is that's David at the call? Honestly, no. I think I feel most comfortable living in the gray at the intersections. I don't, and maybe that's just my personality. I don't love to be boxed. And so, and I think it is a personality trait that I've always, I've always, I think been good at adapting to different environments and making friends across different types of people. So no, I think I think living at the intersections of things, for sure. Yeah. And you mentioned you, I think it was a grandmother, the Holocaust story. I mean, we've talked a lot about in, in VC, like taking risk. But that's like a different level of risk, right? Did that, do you reflect on that in any way? I don't know if that was talked about at the dinner table growing up, but like you have risk at the site and the level of ambition. Your family installed in you? I think it taught me not to take anything for granted. I think my dad often says, can you imagine like you're from the shuttle in Romania during pogroms to Harvard? Where our daughter lives, like next to Central Park. Like in two or three generations, like what a wild timeline. And I think that, and I remember a quote that my dad had said to me, I think it was, I was in middle school, which was a quote in Hebrew, which basically says, which means we strive harder. And it was, it's funny to talk about, but I went to, only for two years I went to kind of a fancy private middle school. And the first year that I joined that I went there in seventh grade, I didn't get great grades. I was distracted. I was probably too social, not focused. And sort of like graduation ceremony from seventh to eighth grade or whatever was like organized by GPA effectively. And I was like towards the back. And I remember being very embarrassed by that seating arrangement. And some version of basically my parents asking me, like, well, did you try your hardest? And saying, honestly, no. And then relaying that quote to me. And I think that sort of lit a fire within me for whatever reason, at a very young age. And the next year, I got straight A's. And basically straight A's throughout high school, ultimately to Harvard. And it was not a school where people would go to Ivy League. So this was a very unusual thing. So I think it was that. And I've always, I don't know that I've ever been the smartest person in a room or the best looking necessarily or whatever. But I always try to be the hungriest. And I think that is, yeah, just not take anything for granted. And attack whatever opportunities are in front of you as aggressively as you can. Well, people today describe you as the super connector and your A6NZ team. Say you're one of the best people readers. I'm curious, did you have any of those traits as a kid? If I asked your high school teachers, would they use similar descriptions? I think so. Again, maybe that comes from, again, kind of living in different identities. Like, I was able to hang with all the EP and IB students in the kind of academics. I was able to hang my best friend was the captain of the football team. I could hang with all the gangster kids. Like I lived in all the different worlds in that high school. And I could be a friend in any pocket. And I, yeah, I don't know that if I, that I have any superpowers, but I feel like I understand people. And that's always served me well as an entrepreneur, an investor. My karmic side hustle is like connecting friends in matchmaking. And I think it's like the same skill set. Again, try to understand people and kind of what their needs are. And I feel like if I can do that professionally, I should be able to do it for love. And I've had a few pretty successful marriages, as somebody had a kid recently out of an intro that I made. And they took a selfie in the hospital. And that felt, I took a lot of pride in that connection. But a lot of things can change. The world people don't change that much. And I think having an ability is under control. understand people's. Yeah, definitely one of my core skill sets for sure. I feel like you'd have a good podcast if you have a decided to stop on David. I appreciate it. Stay tuned in. Yeah. And tell me if I met you when you were 18, so you've just finished high school and you're about to start college, what would I have as you do with your life? Funny. From, yeah, probably the age of seven to probably 18 or 19, I thought I was going to be an orthopedic surgeon, which is random, but I grew up with, I still have, I guess, flat feet and collapsed ankles. And it never was a hindrance to me physically, but I went to this sort of San Diego famous pediatric orthopedic surgeon who had gone to Stanford, became an orthopedic surgeon. And so at the age of seven, I was like, I want to be like that guy. And, and so yeah, I mean, for a very long time, I was good at science. I thought that that's what it meant. You would become a doctor and applied early to Stanford, got in, and ultimately didn't get any financial aid chose not to go. It's ultimately why it ended up going to Harvard, who gave me like half tuition. But in college, I think I realized that I would always sort of imagine a future where I would run a private practice or something. And I was like, wait a second, I don't need to become an entrepreneur to become a doctor to ultimately be an entrepreneur. And it's a stayed with studying biochemistry throughout college, but ultimately chose not to pursue medical school, never took my own cats. But I think probably at that age you would have heard somebody's very focused on entering the medical profession. That's really interesting, because I've interviewed a lot of investors in different fields who are engineers or scientists in their studies. I don't think I've ever met someone who had aspirations of being a doctor or in that medical field. I'm curious if you could go back, would you do it differently? Would you pursue that path and try and become the doctor that you want it to be? I don't know that I would be a great doctor, to be honest. My wife certainly doesn't think so. I'm not the most detail-oriented person. I think to be a great orthopedic surgeon, you probably need to be fairly detail-oriented, measure twice, cut once. I think I've enjoyed all the people aspects of being a doctor and all the bedside manner stuff. And I still love the science. I think there was a world where I might have become like a biotech entrepreneur or something kind of more entrepreneurial in the life sciences of the world. I sometimes join our biotech pitches just because I'm still intellectually curious in that capacity. But no, I think I don't know that I would have loved medical school. And so I'm happy I didn't end up pursuing that. And I hear you in the comment about not being boxed. I say that to my wife and she always laughs because she stats your line don't box me. And I use that all the time and I think I'm the same like spreading across worlds. And I guess that's the beauty of being in tech or being in venture right as you get to see so many different kinds of people but roles and companies. And I totally hear you on that. So you went to Harvard. You got a half scholarship. Where did you start post-graduating in your career? Yeah, so so you know I ended up getting my first introduction to the tech world. My sophomore summer in Silicon Valley. This was the summer 2007. The Facebook platform had just launched. YC had just started. It was like Yelp was I don't know an 80-person company in San Francisco. And so I got hooked into the tech world then. I ended up meeting Julia who is now my wife my junior year had just come back from that summer. And she's here a little crazy. You should meet this family friend who does something in science and business. And a couple weeks later I came down to New York and met this amazing serial entrepreneur, this guy named Rory Rick, who had been the head of M&A at painwebber in the 70s and 80s at a time when a lot of the early biotech companies were going public. He'd started a few biotech companies. He started the largest billboard company in Japan ran a railroad. And then started this big private equity firm called Royalty Pharma, which became the largest buyer pharmaceutical royalties in the world. And we ended up meeting again a couple weeks later and hit it off. And he should come work with me. And so you could come work at one of my biotech companies. I have this private equity business where I have this sort of side project that I spend half my day on. And you know basically it was like I just want to spend all my time with you and download your brain. Like you're amazing. We can sell hot dogs in Central Park for all I care. And so I did a working with him my junior summer, which is the summer 2008 and then for two years after graduating. And it was a very unusual first job, right? I think when a lot of other friends were going off and doing whatever banking and consulting, it just to go work with this amazing entrepreneur. And it was four of us and him sitting around a table every day. As the world is imploding during the financial crisis, he would pull people off Wall Street to explain what was happening in detail. He basically gave us an unlimited book budget and told us to go read about anything we wanted. But modern portfolio theory and come back to him and tell us to tell him what sounded like BS and what sounded real and really pushed us to debate him. And yeah, in retrospect, I think that yeah, taught you the value of your ideas and not your pedigree. He was already like an incredibly successful entrepreneur at that point. And yeah, just having somebody push you and listen to you at whatever 20 years old and 21 years old. And retrospect was a very formative experience in kind of building the self confidence to pound the table when you had good conviction in your ideas. And was this new ventures? Was that the name of the firm? New ventures was a holding company for his venture activity. I really worked for him, but he was the chairman of Royalty Farma, which was the private equity business that he had started. And I sat on the floor of Royalty Farma here in New York City. He had a lot of other businesses going on. We started a kind of small asset management business called syntax. And he also was in part helping run a biotech. I'm actually based in San Diego called CBIS. So I got exposure to all things Rory in that first couple of years. Because if I understand correctly, I think you're there for three years approximately. I'm curious, you joke daily about biotech and health tech. It sounds like a lot of the work you did there was biotech and health tech from my research correct me if that's incorrect. What did you take in terms of your toolkit? If you think of your venture toolkit that we'll talk about with your current role, when you think of those early days, what were the formations of that toolkit that helped you set up? Yeah, it's a good question. I mean, most of what I spent my time on was helping him start this kind of asset management business. And it was again somewhat of an eccentric passion project of his where he would say he was trying to build the first sort of endogenous model of economics like the periodic table of the economic system to map out how the economy breaks out into its component parts. And the application of that idea was to build better diversified equity portfolios. And so we spent a lot of time basically like reading through business models and kind of 10Ks of lots of public companies and categorizing them according to this framework. I did get some exposure to his biotech work. And I wish I would have had more. And I remember Asking him like, should I go be a biotech entrepreneur? And he was very against it, which I always thought was funny. I mean, he's like, like, you know, the biotech is such can often have such a binary outcome. I just happen to get very lucky. And I hedge my bets by starting other businesses at the same time that I was running his first one, which was a business called biometrics. What did I learn? I mean, I think honestly just reading a lot, I think evaluating, looking at lots of different types of business models learning that there's a lot of ways to be successful was eye opening. Rory definitely had the sort of jobs in reality distortion field thing where he could identify a big kind of secular trend early and then had an amazing ability to inspire and motivate people to align to go tackle that opportunity. I think he would admit like he wasn't the best manager in the world necessarily, but he was an incredibly kind of inspirational leader. And I think that is probably a quality that I definitely look for in the entrepreneur said I work with. Do they have an earned secret, a vision of the world that most people don't understand? And he believed that they can, as my partner Alex likes to say, materialize labor and capital. Can they recruit people and customers and capital to go prosecute that opportunity? Yeah, and I think it just, often there's no thesis. It's just like a special human. Maybe I'll click on that and we can jump around here because I don't want this to be a sequential retracing you for journey, but that comedy just made about people at capital. I'd love for you to unpack that because maybe that connects to the point earlier about reading people and understanding someone in that first meeting or second meeting. Yeah, how do you do that now that you've got the experience post that early journey and then I know you're a spark which you'll talk about shortly and of course, Andreessen and everything else. Yeah, what does that actually look like in practice? So say if I came and met you today and I said, David, I've got this great idea. I'm going to be the next big thing. Yeah, how would you get to know me and how would you get to know my mental models? Yeah, I mean, I mean, it's hard to describe it. Part of what I often say is, do you feel the pull from an entrepreneur? It's like a physical feeling almost like a feeling of momentum where you find yourself wanting to do more work and leaning into the opportunity. There's like running down a hill almost, but I think there's a lot of questions and qualities that sort of ladder up to that. I mean, part of what I try to understand is, is this person or team uniquely qualified to go tackle this opportunity? What within their backgrounds or their story kind of best positions them to go prosecute this versus many other players, right? Because inevitably there's going to be competition along the way. Again, do they have some sort of earned secret from prior work experience or in their life or personal life that has given them a very strong point of view for where the opportunity kind of lies? I think the thing that I probably key most off of is clarity of thought. Do they understand what they're going to go build and why and can they are clearly articulate kind of a strategy? Whether that strategy stays consistent or not, I think it's not the point is just how crisply do they articulate their point of view? Often, I think we look for people that are students. of history, right, that have studied kind of the markets and all prior attempts. And I think if you're, you know, gonna spend the next 10 years of your life building a company, like why wouldn't you spend time studying every prior attempt? Because inevitably there's lots of people who've built something adjacent. And it always gives me much more discomfort when somebody is saying, ah, all those people are idiots. We're the smarter team. Here's what we're gonna do. And instead, I think having respect for prior attempts. And in some cases, even having spoken to all the former entrepreneurs in that category, or kind of pioneers in that industry, and then having a very again, clear kind of articulation of what you're gonna do differently or why now is different. But, you know, that can manifest a lot across lots of different profiles of founder, right? I work with folks who've never worked anywhere else. They're like 22, just had a school. They started this kind of in their dorm to season serial entrepreneurs who built and scaled prior companies. And so that's the fun of it. It's like special people, I think, emerging lots of different profiles. And I'd say the power of why, to your point, like I love that, getting down to the second or third order. Why? I think Mike Andreessen talks about this a lot is like people can answer the first order. Why? But then if you ask the second order and third order and fourth order, if they haven't spent the time to your point that earned inside, they probably can't go that deep, right? Totally. And yeah, I think exactly, I think understanding to some extent their backgrounds, like what is ultimately motivating them in my experience is really difficult to build a company, right? So you almost have to have irrational self-confidence or some motivating factor that's gonna make you not give up, right? I mean, it sounds cliche, but I think it is true. It's showing glass and staring into the abyss. And so what is gonna keep you going when shit inevitably hits the fan as it will? So you were at new ventures. You talked about the impact Rory had. I know you went to Spark Next, don't talk about, but what I find really interesting about your identities is you were eventually invested early, then you became a founder, then you became a, I guess, an institutional investor with Goldman and then Andreessen. When you finished up with Rory and you're thinking about the next step in that 2010-2011 period, did you want to explore the founder path or was venture something that he wanted to double click on? I was always very interested in becoming an entrepreneur and I was constantly coming up with business ideas. It was part of my kind of dialogue with Rory at the time and he was always incredibly encouraging. He was like, "I'll see you. Let's do it. I'll sit in your board." I remember him saying to me as I was departing, he said, "If you don't start a company the next four years, I feel like I've failed you." And so he was definitely an early inspiration on that kind of entrepreneurial journey. I was also spending kind of nights and weekends running around the New York City tech ecosystem. Again, in the wake of the financial crisis, the New York tech community was much smaller. Everybody knew each other. I was really inspired and had become an avid reader of Fred Wilson's blog, ABC. And actually in 2010 had applied, they have this sort of famous to your analyst program. And so I had applied to their analyst program back then, made it to the end of the process, didn't get the job ultimately. My friend Kristina got the job who now runs Vanta. But there was a guy there named Andrew Parker and he had been there for about five years and ended up moving to Boston and joining Spark. And so when they were in Spark at USV at the time, had a very close relationship. USV would do like the seed in Spark would do the A or vice versa, I think, across a few dozen investments. And yeah, when they were looking for their first junior person, Andrew was really the one to reach out and shepherd that process. And so I ended up moving back to Boston, joining Spark in June of, I think it was June of 2011. Basically, it's like the one junior kid on the team. It was like seven GPs in me. It was an inverted pyramid, which was amazing in retrospect. And I was 23 at the time. And if I didn't have an equal vote, I tried to have an equal voice around the table. But yeah, it's, yeah, it's where I learned the, I don't know, the craft adventure capital and I'm very grateful for that experience for sure. I of course want to ask you about played because I think you you saw that when you were at Spark and people know you for that. But I'm also curious to ask you, what were the misses and what did you learn from the misses? You don't have to name the companies if you don't want to, but what are any misses like when you look back now that you go, oh, I saw those guys so early and I wish I had the conviction. Too many. Which I don't view as failure canably. But misses as an investor. Also, misses, frankly, is like an early employee. I'll give you one example. That sophomore summer that I was sitting in in Soma in San Francisco was at an online education company, a faded, ill-fated, online education company. But I sat next to our lead engineer. It was his first job at Harvard. I was pitching him all these silly business ideas that summer. And then he goes off and starts Airbnb. This is Nathan, the co-founder and CTO of Airbnb. And I have this very funny Facebook messenger thread with him in 2008 of him basically saying, hey, I'm going to be on campus. We love to get lunch. I'd love to show this new app I'm building. It's called airbredinbreakfast.com. By the way, we're hiring for our first non-technical hires. Do you want to come join us? We're still 10 people in my apartment. And I remember thinking, like, what is this couch-urfing thing? My parents are going to kill me if I drop out of college and ultimately didn't pursue it. A hundred billion dollars of market cap later. But Nathan ultimately ended up becoming an angel investor in Bond Street. He's an incredible human. But I think he put $20,000 or something into the company. But more impactful to me. Anytime I would come to San Francisco, he would carve out an hour or meet me in his office. He was still run. It was already at that point running at several thousand person business. Yeah, just the kind of kindness and generosity that he showed me despite all of his success. It's just an amazing kind of role model. I was lucky and I got that with Rory and I think I got that through people like Nathan and fortunately many others in my career. So I don't know if that's a miss or not, but financially definitely missed a probably nine-figure outcome easily. Yeah, hopefully you saw us the next AVNB in Andreessen, right? That I'm laughing. Totally. And it's funny. I actually first got connected to Andreessen Horowitz through Nathan. When I was going out and raising our series A, I pinged him. I was like, who should I pitch? And he's Alfred Linetsikoia, Jeff Jordan and Andreessen Horowitz. I think he said Founders Fund and somebody at Greylock at the time. And so I pitched all this and then I knew Spark. And so I also pitched Spark. But that was my first introduction to the firm. And tell me, it's back your highlight investment. How did you saw us it? How do you look back on that? What did you learn? Yeah, I mean, by the time I joined Spark, they were already very successful. They had seeded Tumblr. They put a bunch of money to Twitter when there were 10 employees. They wrote the first check in Oculus when I was there. So part of an open question to myself was like, how can I carve out a space or deliver kind of value to the broader firm? One area that I was particularly interested in part inspired by Rory and Park just naively thought that financial services was a big part of the economy that hadn't really been transformed with technology and went down the rabbit hole in FinTech in 2011, 2012, 2013. And I ended up meeting Zach and Will in 2013. They had started out by building a consumer FinTech business. But in order to sort of power that they built core infrastructure to basically aggregate all the transactional data cross bank accounts. And this a bit tangential, but in 2009, I'd first met my venture co-founder at Bond Street. And one of the ideas that we were exploring then was building a geo-targeted ad network on top of transactional data. Four square was very popular in New York City at the time, and you would check into locations. And ultimately, that was a proxy for transactional intent. And so my view is like, instead of using your location to build an ad network, why not just use your actual credit card, you know, transactional data like your stated spending preferences. And we had gone and chatted with AMX and a few other people to try to get access to that information. Ultimately, shelled the idea. But I think I had to some degree a bit of a prepared mind for the kinds of applications that could be built in top of that data. And Twilio was already a pretty successful business at that point in time. I was, again, not a check writer. And so, pound at the table, Mo Coiffman, who was a GP at the firm at the time, ultimately made the investment, took the board seat. But yeah, that definitely was one of the more kind of formative, certainly investments that I made there. And in large part, I mean, it'll drive a good return for them. But it really became kind of core foundational infrastructure for the subsequent decade for Fintech. I mean, it really, I think, catalyzed the creation of many other companies, which, yeah, I'm really proud of Zach and William for everything they built. I'd love to know, like, to compare and contrast back then to now. So if a company like played with starting again today, what would be easy and what would be harder based on your knowledge of Fintech now for 10 plus years? Well, I mean, it's hard to anticipate, like, how, I mean, they really created a market, right, or massively grew a market through their kind of foundational infrastructure. The market for better for worse is far more mature today. And I think the nature of where I spend time from Fintech is ultimately quite different as well, meaning a lot of what they enabled were in this Cambrian explosion of financial product led Fintech companies. People like Chime and Brex and Robin Hood and you go on and on who unbundled traditional financial institutions built a very narrow kind of wedge product, scaled their user base in that narrow wedge product, fee-free mobile first trading or a fee-free mobile first checking account. And then I've now started to re-bundling other financial products to become the primary sort of financial institution for their customers. I think the challenge now is acquiring those customers is much more difficult and much more expensive. The tax that I've met or a Google places on those keywords and that user base is much more challenging. And so my bias since joining in Dresan has been for Fintech companies that lead with software and have the potential for network effect. So ideally, yes, you find the next plaid 'cause it is enabling infrastructure. I think in this moment, AI is obviously like the next massive sort of platform shift in wave that's happening and so much and largely, I think I saw this during my time at Goldman. So much of the way that these financial institutions are run is still like relatively expensive humans living in Excel, doing kind of manual work. Not using Excel as a modeling tool, but using it to like literally track workflows. And in AI is this incredible like paradigm shift where the software can actually do work. And so yeah, I think there's massive opportunities across kind of all aspects of financial services to build amazing kind of enterprise software companies, but ultimately AI native at their core. And maybe this connects to the thesis with Bond Street back in 2013, if I am correct. So you were starting to source companies at Spark that were in that Fintech space, like you said. Social media picked up by then, Facebook had been around for a few years, the iPhone that picked up out of the financial crisis interest rates were on the way down. Oh, sorry, on the way up again in some ways as well. What was that thesis for Bond Street back then? And I guess more importantly, what gave you conviction that you can be the founder to do it? Yeah, I mean, part of it was born out of running around New York City as a young VC, meeting all different types of companies, but often I'd bump into physical products, businesses, or services companies that weren't necessarily a fit for venture capital, but in many cases, we're doing millions of dollars a year revenue, or profitable, or growing, and couldn't raise bank financing. And as you dug into the problem space of getting small business lending, or small business capital, you realized that really hadn't changed in like 50 years, right? You still have to print out your financials, walk into a branch, somebody is faxing or scanning that those physical documents into their system or re-keying the information by hand. And then the six, eight weeks later, you'd get a decision without any sort of visibility in the interim on the likelihood of approval, how much at what rate. And the why now was simply that a lot of the data that we thought we would need is understand the financial health of these small companies at that point in 2013 had just become available online VAPI. So that year, into it, it just launched the QuickBooks API, but also zero, and Stripe, and Expensify, and Harvest, and I had all just opened up APIs. The IRS that year, it started accepting eSignature, so you could get a tax transcript back programmatically. We knew we could write integrations into the credit bureaus, and then again, we had seeded plaid to get access to bank transactional information. And so the idea was like, instead of printing on those financials, you could authenticate access to all your different financial accounts, to Bond Street, and we could interpret that information and ultimately underwrite a small business loan, up to a million bucks in minutes or hours instead of like days or weeks. And the hope was that we could build an aspirational brand that people wanted to be affiliated with. I think a lot of that was true, and there were a lot of other challenging aspects of finding those entrepreneurs at that kind of transactional point of intent, but I think we executed well in the business that we had. - Would you do anything differently today if you were starting Bond Street particularly to your point earlier about AI, like with the power of AI and the tools you've got access to today. And I guess your experience with venture where you spend so much time understanding other companies. If I pushed you and I said, David, you should start Bond Street again today or a similar business. What would be like the two or three key parts you'd focus on? - I do a lot differently. The thing I'm most proud of which I wouldn't change as much is the team that we recruited, like I'm very proud of the group that we assembled, but basically everything else I would have changed. And to be specific, I mean part of the problem was that the wedge product that we started with, or the product we started which was probably not the right wedge product. Meaning we really were offering growth financing. So we were helping small business owners open a new location or hire employees or buy an expensive piece of equipment. The problem with that is those types of transactions don't happen with a ton of frequency, right? And you're not going to borrow, our average loan was $150,000. No, you're not going to borrow $150,000 unless you're immediately ready to sign the lease on that new location. It's like, you're not going to take a mortgage unless you're ready to buy a house. And thus the window of opportunity to sell that product is very narrow, right? And episodic in nature. And so I've written a bit about this publicly, which is if I were over to start another lending business, I probably wouldn't. But I would build a business that led with software as opposed to a financial product where ideally you can give something away for free or where the vast majority of companies could be your customer. You're not ultimately narrowing the funnel on who qualifies at that point in time in your credit box. It's everybody. And ideally that gives you visibility into their financial data. So imagine you had access to QuickBooks, it's like the perfect accounting system or a payments product that powers everything or an invoicing product or whatever it might be, inventory system that ultimately allows you to push the right financial product to the right customer at the right point in time as opposed to marketing into the ether and trying to pull them into your application. Because ultimately you have a lot of negative selection in the type of companies that apply for capital. You kind of want to give lending to people who don't desperately need it. And then ultimately the hardest variable was just the cost of acquisition of scaling that business and finding those customers at that transactional point of tend meant that the funnel narrowed and cost went up fairly aggressively. I think a lot has changed from an infrastructure perspective where you could offer people a different product to keep them in your network. Again, ideally a software product that they're using to run their business. But even things like a checking account or a credit card or would allow you to maintain a more ongoing persistent relationship and then layer in higher value products like a term loan for growth financing over time. And so I would probably just invert the way we would layer in products and ultimately what our wedge strategy was. And I think AI would offer a unique opportunity to do that. An example, and we never fully realized the vision of this product, but we launched a product called Beacon. And the hope and ambition for the company was not to be a lender, it was to be the advocate for the entrepreneur and to abstract away the financial complexity of running the business. Because again, most people start companies not to be the CFO, but because they're passionate about the product or their service or their craft. And so what Beacon ultimately was meant to do was enable you to plug in all your different financial accounts and proactively surface insights about your financial health. To be able to say, hey, did you know you're going to have a working capital gap in two weeks? Push this button to draw down on this line of credit to bridge that gap. And again, I think things like AI would just be a much more powerful tool to be able to proactively analyze the health of a business and be the AI CFO in your pocket. I haven't really seen a great product like that yet, but I still think that opportunity is a big one if you can do it. That's an interesting point. It just made it there. We haven't seen a product like that. What, in your opinion, is the barrier at the moment? Is it regulatory? Is it that earned insight that doesn't exist in founders? I think it's the heterogeneity of small businesses, right? Like the way you run a law firm or design agency or restaurant is just radically different. And at least that's been my assumption. And that offering kind of predictable insights across lots of different industries of different flavors and geographies and sizes is just hard. I think you have seen people do a much better job in kind of vertical software where they've gone deep in given markets. And yeah, I mean, I have a company that I seeded a few years ago called Adaptive, which is built a modern AI-nabled ERP, effectively an accounting system for the home building space. They sell into general contractors who build homes. And that system is offering amazing insights. It does everything from spend management. It programmatically enters invoices and bills and receipts. It can categorize expenses. It does kind of all the workflows between general contractors and subcontractors. And it's, again, kind of abstracting the financial complexity of them running their business. But that is very narrowly focused on that particular-- I'll be at a big market, but a sub-segment where I think the knowledge kind of compounds. So I think that would be probably something we would look for where I would expect to find kind of the opportunity first. And also, I think I said I see the other day that a trend I'm seeing in my angel portfolio is a lot of quite, quite traditionally, industries like banks, accounting firms, law firms, consulting firms, hospitals that traditionally wouldn't buy as much software. A very curious about software in this AI first world. And it's interesting whether-- even like Goldman, like you know this really well, and we'll chat about it. They won't just buy software from a startup, right? Because of the risk appetite associated with that, just given the structural nature of the business, where it's a KPNG or a big law firm. But I have three companies in my portfolio that are doing that. They're like their first customers. I'm curious, how do you reflect on that and has that changed your diligence process for an early stage investment? 100%. I mean, I think it's a huge kind of tailwind for companies selling into large enterprise. And what I would describe is both bottom up and top down momentum. Bottom's not meaning the first wedge product, and probably the AI product that has most kind of market pull right now is anything. code gen. We're large in masters and cursors as an example. And it's like the fast occurring business we've got one of the fast occurring business we've ever seen. And so it's just having a massive impact on the kind of large engineering basis of all these companies. And then they're I'm sure adopting Microsoft code pilot or they're using chat GBT or cloud in their personal lives. And so there's this sort of ground swell of support for AI products kind of at the individual employee base level. But then AI is like the number one topic of conversation I'd ever read board meeting as well. And I think what's unique about this kind of product cycle is that whether you're technical or not the CEO or any board member can now plug a prompt into one of these models and intuitively understand the impact that it could have on their business. If you're 10 years ago, if you were the CEO of Goldman Sachs and you asked, do I need to be in the cloud? It was like an esoteric question, right? Well, what impact is that going to have on my banking business for my trading revenue? And yet now it's okay, give me all the market research on proctor camel. And it like immediately spits out the DCF and the market research and can pull comps. And you can just imagine, okay, wow, that is whatever 50% of the job of an investment-making analyst, like time to value that where people spend do their work is going to radically shift. And you can extrapolate that insight across almost every function within a big company. And so I think it's just making the appetite to adopt a lot of these technologies and the sales cycles move a lot faster. The other thing that it's doing, which is not unique to large enterprise, and it's had a weird impact on where we've been investing in some ways, is that it's made industries that have never been particularly interesting to sell software into radically interesting businesses for AI. Again, large part because you're tackling the, you're accessing labor spend as opposed to just IT budgets. Because again, I think what's most unique about kind of this AI product cycle is that the software can actually do the work. And so whether that's in areas like Plaintiff Law and a company called Eve that I sit on the board of or in the home services space or in healthcare or in financial services, these were hard markets or small markets in some cases to sell software into. There's some of the faster growing companies we have in our portfolio now. A question that I'm asking myself and I'm curious how you're thinking about it is how do you diligence for the compounding competitive advantage of a time? And your team said to me, this is a question I see meetings at the moment with a lot of these companies that are getting to two, three, four million ARR in weeks. But then may have a really high churn rate or may not have stickiness, which is fine for an angel investor like me, but a fun like you who can only make so many investments in a year, how do you factor in the differentiation between curious ARR and like potentially sticky ARR? No, it's something we debate often. That is the core question that I often ask at every pitch meeting is just what is what do you believe is your source of compounding competitive advantage? I guess my like pithy take is that moat still matter. And I think they're largely the same. And what do I mean by that? It's ultimately I still think incredibly important to own the end and workflow to deeply embed yourself within your customer to become the system of record to have a network effect or a reality big did your product. I think those were all the kind of heuristics that we would always look for when evaluating software companies. I think that the thing that's fundamentally changed about where we are in this product cycle is then the software itself can actually do the work. And so just as an example, by sitting on the board of this company, Eve in the plaintiff law market, legalized it a very noisy category you had you have and had tons of different kind of point solutions, right? An app embedded on Microsoft Word or that just does red lines or just creates a demand letter, which is a core artifact in a plaintiff lock case to to J and man, the eaves founders credit they hadn't a differentiated point of view. They wanted to really own the kind of end to end workflow from client intake all the way to outcomes. And I think what is unique in some ways about the plaintiff law market is that they don't charge by the hour, right? They operate on a contingency basis, which means that for every, which means they only make money if they win. And as a result, for every 100 leads they get they take one case. And so there's a ton of top of funnel, what I call like messy inbox work to basically sift through mountains of medical records and employment documents to figure out if this case is worth your time. And so Eve now has voice agents that collect evidence from prospective clients programmatically turns out sifting through those documents and finding sigil in noise is a great application for LLM so they can do triage or kind of lead scoring scoring it to the top funnel. The product drafts a medical chronology can create a demand letter can step through all the different phases of litigation. And then ultimately it was also quite unique is that the outcomes of these cases are not public, right? And so, which means that it's not a data point that any of the large model companies can trade on. And so a motorcycle accident in the state of Michigan again, state farm is not a public data point that anybody else knows, but yet it informs the product right and actually better informs intake. So you can now go back to clients and say, hey, like this case given all the variables we know it for all the cases we've ever helped facilitate this case potentially worth $50,000 in that case, by the way, potentially worth $5 million. And so you build this unique kind of data flywheel data asset, which makes the product smarter and faster. And so it's not just about doing work more officially. I think ultimately they will get to a place where they can actually impact time to resolution like the speed with which a case is resolved and actually outcomes, right? They can better say given this counterparty, here's a phrase or a demand that you should include in your in that demand letter. And that will likely have a material impact on the outcome and settlement of this case. And so I think eventually is showing up to litigation in this market without Eve. Maybe I'm projecting forward. It's like being unprepared for battle. So it's against guns or something like. And so I think ideally we look for companies that have again sort of compelling about advantage. And I think also which can clearly articulate not just a cost reduction story, which I think is a large part of the AI market right now, but also enable meaningful revenue growth, right? Or in a bill and deliver ultimately they've been a product or customer experience as a result of the technology. Maybe to zoom out on that point, David, a line that I love that you've written about nothing it's in your LinkedIn bio is opportunities live between fields of expertise. And I'm curious when, when has that been true in your life? As we've discussed, even back to, I don't know, my childhood, I think it is a metaphor for my life and a metaphor for my career in some ways, living at the intersections of things. People often ask, am I an entrepreneur, am I an investor, am I an operator? Do I feel like I'm more Silicon Valley, am I more Wall Street? I think the extra is just yes, right? Tell me more on that. Yes, but still like that's a lot of experiences in one life. And you're still young. I'm packed out. Tell me the mental dialogue. I think you just, well, I actually think it's going to become more important than ever. I'm talking my own book, but I think having being able to take different perspectives on, on a problem, I think, is this source of compounding if that's advantage, right? Not, if something is too easily bucketed, it is very legible, right? And I think if it's legible, it's often like the, it's priced in, right? Like people understand it, it's very, it's like a known quantity. And I think things that are hard to bucket that often either live between industries or require kind of different perspectives, as I said, is where opportunity lies. So I think it's both kind of an investment philosophy that I've prosecuted here in Andries. And it's been a particularly fun way to invest at Andries and Horowitz largely because we have such geek domain experts across so many different categories at the firm. And I run around the building and lock arms with different GPs and done deals kind of at the intersections of different categories. I've also felt that in each of my different roles, like even inside a Goldman, I was a very different kind of person than a lot of the other folks. Certainly in like our firm wide strategy team, like I was the weird startup guy and a team of big bankers basically. But, you know, the kind of job that I created myself was ultimately to be a branch between Goldman and the outside world. And I think the unique thing about Goldman Sachs at the time was, unlike many kind of large operating businesses, it's really a confederation of lots of little businesses, right? You have, you, you, as a firm, you could be an equity investor, a debt investor, an acquire customer, a supplier. And so inevitably that meant if there was something interesting to do in the outside world, they were somewhere to put it. And so a lot of where I spent my time was just running around the building and mapping the organization of Goldman Sachs, which was quite complex. And again, being a bridge largely, I think, between the temporal and kind of Wall Street. But I think having a very kind of entrepreneurial mentality, probably not having fear, having just run through walls for the past four years as a founder and CEO, again, enabled me to attack that firm and find ways to end value a lot more aggressively than I think somebody who probably just rubbed very linearly within the organization as a trader or banker, you know, well, manager, what manager would have you? And so I think, yeah, again, I'm always trying to understand the other angle of whatever I'm looking at. I mean, Andrewson, one of the things that you and your colleagues talk a lot about is building brand and distribution power, right? And I think Andrewson's done that really well. Goldman's like the golden child of that in financial services, but also agnostically in society. You go to a party and you say Goldman Sachs, there's a certain response and a level of respect. I like to think as I see out of that. Can you share what you learned from Goldman about, did I say go back? No, all good. Can you share what you learned from Goldman about building those sort of rivers of gold, of capital. profile, brand distribution, high-profile, ambitious teams, that perhaps you brought to Andreessen? Yeah, look, there's a lot of things that I admire about Goldman Sachs. I think, and there's a great book, which I've commented before, but called The Partnership, which could chronicles Goldman's history. It conveniently ends at the 2008 test book for the financial crisis, but in 140 years, I would argue that Goldman Sachs was one of the most entrepreneurial financial institutions in the world. It was not a business built through bank mergers. G.P. Morgan was like the fish that ate the whale. I mean, it was just in Bank of America. Many of these other banks were just a series of bank mergers that in the snowball effect. Goldman is quite different. Goldman was really built brick by kind of entrepreneurial generations of entrepreneurial partners, kind of raising their hands and going off and building Europe or building them all, managing business or building the Merchant Bank. And I think that kind of entrepreneurial spirit is what I think made Goldman quite unique for a very long time. I think that has to change as the business became much more of an operating business than a partnership. And there's a bit more kind of centralized power and kind of command control. And I think a bit of that is is waned, I would argue, over the past several years. That said, I think what Goldman does remarkably well, it's a firm with, I forget, like, maybe 45,000 employees at this point, but it doesn't feel big. Like you can get access to anybody within the firm very quickly. The way that Goldman people communicate, it was overcommunicated, they called it like posting. They copy people, well, proactively in emails, they're very clear. When they say they're going to do something, they do something. There's a sort of a level of excellence that I think Goldman has done a good job was instilling culturally in the people that it trains and recruits and rows. And you feel that even when people leave, like, we have a number of Goldman folks here in Andreessen and they just operate with kind of a clarity and efficiency that just feels notably different and it's why even coming to Andreessen, like, we are a big venture capital firm for 600 people. We are very small compared to Goldman Sachs for any smart financial institutions. And so even 200 West, which is the main building in Eric City, that building had 10,000 people in one building. It's like its own mini city, but I think I found that I was able to navigate that firm quite efficiently. And again, people communicate very efficiently within such a big company. It's main Andreessen feel, not that big and small. But there's a lot of things that I learned just culturally about kind of excellence, communication, an entrepreneurial spirit, building something enduring for the long term, kind of the responsibility you have about being at the center of a market, brand building. So there's quite a bit. So bring it back to the personal element we talked to the start about your, the Mexican Jewish kid from San Diego. Now in 2020, you're in the center of New York, you're at Goldman Sachs, you've had your company, it's been acquired. What was that mental, what was that self dialogue with you with yourself? Did you say David, yes, I'm on the right track, and life feels good. Oh, did you still have that itch around? No, what am I doing with myself? I've had all these successes, but I'm still figuring it out. I think the first six months was like recovery, kind of like I was just exhausted having run a business for the past several years and putting 120% of your life into something. It's also a weird emotional feeling in some ways where you're, again, about 40 of us joined the firm at the same time and you're no longer, if it wasn't obvious, and I wasn't the CEO of Goldman Sachs, to help your team become successful, you have to allow them to assimilate into the organization, and that's weird feeling, right? They spent the last three years looking to you, forgot instant direction, and now they're reporting to other people in the organization, and you have to let your, it's not a perfect knowledge, but let your kids kind of go off to college or whatever it might be. And so emotionally, that's unusual. I think over time, I braced the moment and basically said, listen, like Fintech inside of a big financial institution is just technology. I'm here. Let's make the most out of it. I have no fear. And I remember asking myself, like, what does it mean to take risk within a big company? Because I think my natural DNA is as an entrepreneur, it's to be reseeking. And I think that for me meant, like, completely disregarding my job title, my job description. Speaking very plainly to the most senior people at organization, the most junior people, I would just fire off cold noodles like 10 a week, just again, to really nap the organization to understand what people needed, and not just had a compounding impact internally, such that when people were looking for somebody, kind of entrepreneurial, to work on something, I would then get pulled into to these projects. I got robed into really our firm wide technology strategy. I got a cold email from this woman, Stephanie Cohen, who had just been promoting the Ditchie Strategy Officer, looking to get connected in the tech ecosystem and open my network to her and that she started reciprocating pulling me into more strategy and a board conversations. And at some point, she's writing job description and work with me and ultimately stayed largely for her. But yeah, it was a unique experience, for sure. Take me inside late 2020, so you've been in Goldman 3 years, you've had a company acquired. You'd worked in Ventually, we talked about Spark and Rory. What were you thinking about doing next? A sentence that I had been repeating myself for a while was this notion of wanting. Always wanting to build a firm more than run a fund. And it's the way that I really began articulating where I feel best, which is somewhere between being an investor and an entrepreneur. And I had an opportunity to join a different venture capital firm as an investor, but in my head, it was purely an opportunity to be an investor, not an opportunity to build a business. I was lucky in the sense that I would catch up pretty periodically with my now partner, Donald Trump Hill, and it became clear that Mark and Ben wanted to open a New York office. And it was a unique opportunity to help plant the flag here in New York City for injuries and horrors. I never really can't really thought about injuries and largely because in my mind, I was so West Coast dominant and I didn't want to, certainly my wife didn't want to move into the West Coast. And so it wasn't at the top of mind, but I always viewed injuries and very much as a firm more than a fund. And the more time that I spent with Alex and Mark and Ben and a bunch of the other partners, the more, yeah, you realize this was an institution really run by entrepreneurs and there's a lot of ways to be successful. That was a very particular aesthetic that I was looking for and it was a bit serendipitous was not something I originally sought out, but I'm very grateful. And I think something I've learned is that careers are non-linear in that way. And so I jumped at the opportunity and yeah, it's been five years at this point, which is wild. And you were the first GP, I believe, in the New York office, right? So you started and then you've got a team of what 100 you was saying the other day? Yeah. Yeah, join the were two of us basically here, myself and Brad Kern who at the time was running our good and market organization. We've got a lot. Yeah, we know about a hundred bulletin employees across all the different investment practice areas, our operating platform, our new media team, and we're expanding. We have two, I'm sitting currently in our New York office in Soho. We have two floors currently. We're opening two more floors later this year than it's been, it's been fun to, it feels a lot more real here in New York than it did just five years ago, which is remarkable. We've touched it a few times on East Coast versus West Coast, and we talked about Boston with your experience at Spark. People are really curious to know your perspectives on comparing and contrasting to ecosystems. And maybe the question is like, what does Wall Street do better than Silicon Valley, but then what does Silicon Valley do better that out competes Wall Street? What do you think of the startups you've sourced at any differences you've noticed? I mean, I think what Silicon Valley generally does incredibly well is just like, it gives permission to dream and dream big. And I think it's much more permissive in some ways of failure. In fact, I think failure is championed. It's almost a right of passage that you'll invest in somebody. Their first company doesn't work out and their next business becomes stride or whatever. Like it's, that is a remarkable thing about Silicon Valley. I think it's almost unique to, I would argue, to America, but really more or so unique to Silicon Valley in particular, just how much culturally it champions trying and being in the arena. I don't know. I mean, I think technology is Mark in recent road like software is eating the world. Technology is now permeating every part of our economy. I mean, I think what Wall Street has done well, maybe this is back to the golden point, like it's built in during institutions, right? I think people in time will tell, right, like a lot of these companies are more nascent largely because technology has such a disruptive force. But if you want to build a business that can exist for 150 years, how do you intentional about the foundational infrastructure that you lay? How do you generate profits and have a focus on kind of the commerciality of that business? But also, I think importantly, and this will be interesting to watch more time, how do you continue to continuously reinvent yourself, right, as markets and technology adapt? People have obviously, the firms like Goldman have done that quite successfully. They've grown massively by revenue and headcount over 150 years. I was going to change a lot of things and so I think it's going to be an even bigger disruptive force to, I can most couldn't convince going forward and that's why we're excited about a lot of the start. For backing, it's also why we spend a lot of time with a lot of these big financial institutions and other large industry players to help be a bridge between both worlds. I know many of your founders and I said, "What's the one question I should ask David?" Most of them said, "What is New York City startups not do as well as SF startups in New York experience?" Are there one or two traits that NYC startups just don't have that SF does? I don't know that it's endemic to the founders necessarily, but I think that the challenge that New York has is just the depth of talent at the middle management level. I would argue the VP's of marketing, the VP's of product, the COO's that have seen companies scale from 100 to 1000 employees or 1000 to 5000 employees. Those are just rare in New York City. New York City then they are in Silicon Valley and those are really important people to be able to recruit and retain as if you really want to drive congeneral outcomes. I think that's going to happen as the ecosystem occurs and we have a lot more successes, but New York used to get a knock on like engineering talent. I don't think that's the problem in my opinion. It's more, again, that middle middle middle trend of people that have seen excellence, that have seen hyperscale, that's a rate limit or at the moment. The other thing that I think is more uniquely Silicon Valley at least for now is there's a lot more deep infrastructure or research orientation. I think there's a reason a lot of the big foundation model companies or hardware or silicon businesses were domiciled in Silicon Valley. I think companies that are uniquely in New York and back to my same theme are those that sort of intercept traditional industries that live at the intersection of healthcare and technology or finance and technology or advertising, a fashion. There may be less deeply technical, but more commercially oriented in nature. To the flip side, I think the thing that New York companies benefit from is that if you're selling it to the enterprise, basically every large company in the world has a presence in your backyard. It's much easier to get in front of basically any large company in New York City than in the St. San Francisco. It's one of the main reasons I'm building here and investing in companies that are based here as well, thank you for a very candid answer, I can see what people like you. This is why because you've actually given some depth to that answer and not just given some like wishy-washy answers, so thank you. You talked about a firm not fun earlier and people love your article and I think it's got some great responses online. If I could flip that and go someone who's potentially critical of A16Z, what would they say about that thesis? Yeah, I mean the people that try to counter position against in recent basically say that we're too big that any individual investment doesn't matter, that it's one of a big portfolio of events, ultimately the operating platform is a way to scale the GP and a way to help the entrepreneur. What else? It's not true, is the funny part because I know this having spoken to many of you found is, I mean even right now it's what's happening geopolitically, I just had this morning like you guys have played a huge role in getting people out of cities, which is not something of AC fun does. Yeah, I mean I find it funny like there are other other very large venture capital firms who have a lot of, we happen to spend our management fees and building a big team to help support our companies. The alternative and the path that most people take is they just pay themselves much more. They don't have big operating team, they just have a smaller number of investors who capture those the economics for themselves. So I think one of the kind of benefits that the firm had at the very beginning was that Mark and Ben were just so successful before they started in recent markets and they were the customers of the best venture capital firms in the world when they started the business and so they could take a very long term oriented view and from the very beginning reinvested all the management fees back into building this this platform, which benefits from economies of scale from it is our one source of our company competitive advantage. And the reality is like every entrepreneur that I work with gets 100% of my time right and we're in WhatsApp every day. We have whatever cadence of weekly or biweekly calls they want and they're getting all of my expertise in the battle scars and whatever wisdom I can share, but the reality is I'm not going to have every answer right and I think there's a, I think the humility and saying that and yet a lot of my job in the way I view my job is a to deliver everything I can as individual, which you're going to get from other VCs, but it's also to marshal the broader resources of the firm right to put this whole war machine in your corner until the board in your favor and inevitably for the things that I don't know, there's somebody in the organization that has had that experience that has scaled the company that's worked in that operating role at it in a similar circumstance and and that's where like knowledge compounds and in some ways a very jealous of the founders that that kind of accesses. I wish I had access to a similar platform when I was growing in the dark as a first time founder and just like stumbling over myself and making all sorts of mistakes because it would have saved me a lot more time and brain damage can't only so yeah, I find it a fine narrative, but you know, everybody has their stick and it's a good pattern mark and I understand why they do it. And I love the stories from your founders about how you source some of them where I think a lot of VCs will send an email and say, "Hey, let's catch up." But even talking to like your partner Mark and Risco, there's a bunch where you've actually found a senior exec at a customer that they're trying to close and that's been your way of doing the work before meeting them. And I think that's again unique because there's always a joke about VC value add, right? Every VC says it, but how many actually do it? And I think some of those stories I've heard firsthand unsolicited from your founders about how you've done that, but you and Mark and your team is special because I don't think that gets talked about enough. I appreciate you saying that. I mean, again, I think in my heart, I'm still an entrepreneur and more than I am an investor and I want the founders that I work with to feel like I'm an extension of their team, right? And not in any overbearing way, but I think in many cases, we can really move the needle. And so I don't know any different. I just try to play it fairly in some role in helping build these businesses, especially where I feel like I can meet in full value. But yeah, I mean, one of the, I don't know if this was the example you were thinking, but one of the, I think that's examples of this was a dinner we hosted with the founders of Bowman. It was a very competitive process where their series A was preempted by somebody on the board of their biggest customer and we kind of had to swoop in and do the work perfectly. And I remember taking Umher and Dean, not, I don't think Dylan was at the dinner at for a meal. And at the end of the dinner, they built fixed income trading infrastructure selling to the biggest financial institutions and well, management platforms in the world. We emailed, I think it was the Chief Strategy Officer of Vanguard, the Chief Strategy Officer at Edward Johnson, Chief Strategy Officer of Goldman Sachs and the Morgan Stanley. And it was like, can you email the founders a moment like now and advocate ideally for us and for David to do this deal. And within 10 minutes, they all got emails from all these firms. And we're like, you need to work with injuries, you need to work with David. And by the way, can we schedule a call like next week to learn more about the business? And several of those companies that I just mentioned are now customers of moment that have driven very vehicle revenue to the business and increased the value of the company quite a bit. And so that's how we try to show up. And now it's before we were investors. That is just demonstrating, again, I think just frankly, like what I would call an authentic non-transactual relationships, like just trying to help people in the ecosystem such that when you need something, people are very willing to throw the weight behind you and be in your order. Totally. I've heard of it in a moment, but others fear who are recently on the show Nick and others like that. So you've got countless stories. Oh, on that point about, and we're coming to wrap shortly on that point about building a network of your own sourcing founders, keeping up to date, one of the challenge I struggle with is time management, like even though AI helps and we can find efficiencies, I'm curious how you do that because I mentioned the start, people said you're a super connector, you're very genuine. I think it's proven in some of these answers to these questions where you could give me a very surface level answer, but you've actually given me a level of candor. How do you divide your week? If you think of this week or you'll ask a couple of weeks, like particularly on information with the world moving so fast, how do you stay on top of things and what is that? What's the secret David Sous? I don't know that I have a perfect recipe to be out of. Sometimes it feels like I'm just like surfing my calendar. I try to surround myself with people that I admire and I have a small group of thought partners. I started this funny WhatsApp group during COVID in a moment of transition when I was trying to figure out what I was going to do with post-Golden, that I call friends to plot with. And it's a bunch of kind of entrepreneurs, other VCs, the kind of common thread of just people that are, I think, good humans that are generous with their time and their insights. And that's been an amazing kind of forum that I'll just ping pretty periodically with. Things that are happening, questions about what's going on in the world. And so I think trying to keep a stable of those types of people in your corner, just because the market and everything moves so quickly, and it's so dynamic. A lot of, again, a lot of people have so many different ways of sourcing investments. Again, I'm probably, if you can tell, like more kind of people centric and kind of network oriented as opposed to systematic from like a tools perspective in any capacity. The best centros come from our founders. It's why I dedicate so much time when helping them build their business. But in terms of meeting, I take a high signal and there are a referral and kind of conviction in their friends. But also when we're trying to win. I mean, the best, I can wax poetic on the virtues of Andre said in our platform and the war machine and all that. At the end of the day, like, it's much more powerful to hear it from one of the founders, right, directly. And so the first thing I often do when I'm really impassioned about a company and we want to work with is just connect them with other, oh, we fill in or with a tray, a tenor, or Jay at Eve or any of my companies. And my hope at Newell articulate how we showed up in good times and bad times. And that's something I've taken from my own experience running a company, right? I try to sort of channel back to, we were very fortunate to have good investors and good board members. Monster was definitely not perfectly up until the ride. It was very, it sounds great. There's a nice bow and landed at Goldman, but a wing was broken, the engine was on fire. I mean, it was a hard, it was a hard journey. But people like Satya, Atumbru, Andrew and Sparkite, these were people like in the trenches with me. And maybe your returns aren't generated in those outcomes, but your reputation 100% is solidified in those moments. And I think that's just where the empathy having been a founder comes from. And so again, I just really try to show up for people we work with and respect the fact that they're doing something in the. incredibly difficult. And I want to do everything I can to help them be as successful as we can. Last question and then we'll wrap up with rapid-fire sprint. If you could visualize a metaphorical learning room, I call it a whole famed learning room, and say you've got four seats, and you've got once you've got five seats and you've got one chair and you can invite four people. Four people, let you know, you've already named some people in this conversation that you've learned from and spent time with. Who would be those four people you'd love to have in a room over a meal and just ask questions? Oh wow. I mean so many people have had such a big impact on my life, obviously. Look, think about that. This maybe sounds cliche. I think my mom is at a huge impact. I think like I wouldn't have been a successful in any capacity in my life without her being so involved at every point in my education, in my upbringing. I think my wife has definitely opened a very different dimension in my personality. I think we're very different people. She's one of the most like independent thinkers I've ever met. She doesn't care what anybody thinks. She says, well she believes she's the one of the hardest working people I've ever met. She can't fake it, so she's suy generous in that way. And I think she's much more in tune in some ways to like her emotional intelligence or like she's willing to live in in emotion more in some ways than I am. And I think that's we've been together a really long time. We've been together since 2008. We've been married since 2013. So we were like babies when we first got together. But I think it's created all sorts of dimensionality in my life. And now we have a 21-month-old daughter and a boy on the way. And so she's got a massive impact on the way I live in the world and shove for our kids. Rory, I've talked about him a lot. It was a short, I only worked for him for two years. But again, I think that the fact that he taught you the value of your ideas and not your pedigree at a very young age was again, in retrospect, very informative to give me the confidence to pound the table at Spark to do the deal or to speak truth, the power, golden sacks, or to have the conviction of my own to go start a business when I was 25. And he was so successful. And so it's okay if Rory believes in me, like why shouldn't everybody else? So let me go do that. And he was a good, again, archetype for just what it means to be a good human despite all the success. Like him and people like Nathan, despite the massive financial success, I think financial success is almost like a magnifier to whatever is there. And I think it's just good people. And so I think I think that's taught me to my in-laws in some ways are very much like this as well. I don't know where the fourth would be and there's so many other people that have, again, taken bets on you early in your career. You never forget those people. People like something like that. Tell me about my out of Mark and Ben. If you could pick one as a full of Mark Andreessen or Ben Horowitz, who would you pick? Oh, that's hard. Hopefully they won't listen. They don't know that I who I pick. I mean, they're so different. I mean, Mark is maybe the most intellectually curious person I've ever met in my entire life. He is a galaxy brain. He's organized his life in my observation around information consumption. Ben is a people leader, the EQ, the sort of face of the firm internally. He's our CEO. Mark is our chairman and chief strategist. Nobody reports to Mark. I think intentionally Mark lives in 100 WhatsApp groups and Slack channels. Again, like Hoover's information to the machine and places the generals on the battlefield. That's how I observe him, which makes him one of the most interesting people to talk to because you could literally ask him about anything. And he'll just like speak in paragraphs and be able to quote periods of technology history or I mean, literally anything. Scripture, I mean, you can ask him if all sorts of things and he will explain it. So pick one day. Would you pick? Go with Mark just because I enjoy learning from him and to being him, but yeah, hopefully Ben is. But no, it's me putting you on this spot, but they buy great. I mean, nothing just listening to them. You can get a clear sense of their like the powers and Ben's been doing a bunch of podcasts recently. And he just incredible like granular detail on operations and people management that that I think is like LLM of its own that the two of them could build and like people could just have questions all day. I want to move to rapid five final sprint before I do is anything I have an ask that you want to touch on that you wanted to share. No, I think this was great. We've been pretty extensive. So appreciate it being patient with me. Is there one non-work investment that you consider the best in your life? Is there a holiday or a course or a hobby? By far the way, we work my wife and I worked with a surrogate to have our daughter. My wife was enabled to carry and it's a weird way to answer that question, but it's the most generous act I think anybody can do. I mean, she's literally helped us build our family. And so it's like by far and away the best money I've ever spent in my life. And I think ultimately what I've observed is it wasn't really an about that for her. And I think it was she had three kids around. We were the first family she had worked with in this capacity. I think she knew that she wanted to help somebody else after she had her first year. And yeah, I mean, her daughter June is like the best thing that ever happened to us. And so I can't think of anything else that I would have rather spend money on than that. I would do incredible. 100 gyms over. Yeah, incredible. Is there one thing you'd like to learn in the next six months in what kind of genuine life? How to manage two kids? We have a son coming again July 1st. And so yeah, how do you juggle life and work in two kids at the same time is complicated, but people that have done it obviously with even fewer resources. So that gives me comfort. Well figured out. I didn't. Anyway, on a more kind of work tactical level, I've been experimenting a lot with a lot of the yeah, coach and platforms like cursor and cloud code. I think it's just like remarkable what you're able to do now. And in natural language to create software. I think this is why I think range and disparate experiences and perspectives are going to become more valuable because depth of expertise like as an engineer, for example, is just becoming more democratized. And so being able to understand context from lots of different places and being able to point technology at your own discretion, I think is becoming more and more of a superpower. So I think just learning to be fluent in the toolset and how that kind of affects my work and our I'm sure it'll show up in our personalize as well. More than it already does. I think it's something I'm excited to continue an experiment with over the next few months, any years, I'm sure. One interview question you love asking candidates, I genuinely ask in a recruitment process, but it could be enough found a diligence process. Some version of what gives you energy. I think people do their best work in the things that give them energy. Most of the people we invest in are very smart, right? They hit some level of success in that they can draw intelligence that they could do lots of different things well. But I think the people are exceptional a lot again in the things that give them the most energy. So it's always valuable for me to understand the things that they that are energy draining. And then ultimately, I try to assess how are they complemented by the other founders on the team, by the team that they've recruited. Do I think that they will continue to spike in this capacity? Will the company benefit from that thing that gives them energy? And the way that they answer that question is often quite telly too, like how honest are they? They describing the things that actually give the matter of the versus the things that they really don't like doing. One pitpeave, arrogance. Yeah, I just think I think having humility in I think there's a difference between confidence and arrogance, right? I really look for a sense of humble confidence, right? I described this earlier in the founders. We look for like students of history, right? They have kind of respect for all part of the time. So it doesn't mean that they have they don't have the confidence to go tackle a marketer, prosecute the opportunity with aggression in front of them. But I think being dismissive or too arrogant really bothers me. I think, yeah. And again, and every level, whether you're a founder or you're an executive or a surrogate, it really bothers me. Yeah, that's one thing as a tech ecosystem. We can definitely continue to improve for sure. And last one, if you had to recommend a question, I should ask my next guest. Of course, you don't know the next guest. He's the anything I should add to my notes. Maybe some version of what gives you energy, I think is would be interesting. I think you did touch on this, but like what in your life or career are most shaped who you've become in some way? That maybe it's too broad of a question, but I'm sure people might like have lots of different kind of anecdotes from their past then. They view as very informative. Yeah. David, that's the finish line. Thank you so much. I really enjoyed learning about your story. And thank you being patient with my questions. And yeah, see you soon. No, this was awesome. I'm really appreciated and thanks again for having me on. That's a wrap. So it's something in this episode. It's back to thought, send it to a friend or colleague. And to curious that pattern with us and the curiosity center, whether it's this podcast, to our reports, events and more, and during the ranks of existing commercial partners, including Google, KPMG, Vanta, and others, my details and the show notes. Until next time, I'm David Taggerwell, and this is the Lifeline's podcast.