20VC: How We Made $800M on Coursera | We Lost Money on Uber and Made Money on Lyft | We Did 3x on Postmates in 18 Months | DPI is King, MOIC is BS | We Dodged Theranos and I Still Lost Millions with Larry Aschebrook @ G Squared

16 Jun 2025 · 1 h 35 min

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Podcast Summary: The Twenty Minute VC (20VC) - Episode with Larry Aschebrook @ G Squared

Episode Overview In this episode of The Twenty Minute VC, host Harry Stebbings interviews Larry Aschebrook, Founder and Managing Partner of G Squared, a prominent venture capital firm. Larry shares an honest account of his journey in venture capital, discussing both significant wins and substantial losses, offering insights into the realities of investing in high-stakes startups.

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Key Themes

  1. Early Career and Entry into Venture Capital
  2. Background: Larry grew up with humble beginnings, transitioned from fundraising for academic institutions to venture capital.
  3. Initial Investments: He invested personally in companies like Twitter and Uber while still in business school.
  4. Philosophy: He emphasizes the power of investing other people's money (OPM) to create wealth.
  1. Significant Wins and Financial Highlights
  2. Coursera: G Squared was the largest shareholder, yielding an $800 million return for their LPs.
  3. Lyft vs. Uber: Larry details how investments in Lyft were profitable, while Uber resulted in significant losses.
  4. Spotify: Larry made a significant investment that turned into a billion-dollar outcome, highlighting the importance of timing and market understanding.
  1. Challenges and Losses
  2. Theranos: Discusses a close call with investing in Theranos, relying on gut instinct to back out.
  3. 23andMe: Larry reflects on a massive loss of $70 million on this investment, indicating the pitfalls of chasing potential high returns.
  4. Getir: A major investment that turned sour, with Larry noting emotional struggles and lessons learned from overcommitting.
  1. Investment Philosophy and Strategy
  2. DPI vs. MOIC: Larry emphasizes that Distribution to Paid-In (DPI) is a more critical metric than Multiple on Invested Capital (MOIC).
  3. Market Conditions: Discusses how the venture capital landscape has shifted, particularly post-2021, and the need for adaptability in strategy.
  4. Investment Approach: Focus on fewer, concentrated investments in high-quality startups to minimize risk.
  1. Future Outlook and Thoughts on AI
  2. AI Investments: Larry expresses confidence in investing in companies like Anthropic and OpenAI, seeing them as foundational players in the AI space.
  3. Market Dynamics: He believes that many existing companies will struggle to adapt to the necessary technological advancements, likening them to "vampires" and "zombies."
  1. Personal Insights and Reflections
  2. Happiness and Money: Larry reflects on the complexities of wealth and the drive for personal success beyond financial metrics.
  3. Leadership Style: He acknowledges the need for improvement in his leadership approach, focusing on being more open-minded and communicative with his team.

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Key Takeaways

  • Persistence Pays Off: Larry's journey exemplifies the importance of resilience, learning from both successes and failures.
  • Focus on Core Metrics: DPI is crucial for measuring success in venture capital, emphasizing cash returns over theoretical multiples.
  • Navigating Market Challenges: Adapting to changing market conditions and learning from past mistakes are essential for long-term success.
  • AI as a Game Changer: Investing in AI is seen as a pivotal move for future growth, with a focus on foundational technologies and companies.
  • Self-Reflection and Growth: Continuous self-assessment and a willingness to adapt are vital for personal and professional development.

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Conclusion Larry Aschebrook shares invaluable lessons from his extensive experience in venture capital, emphasizing the balance between risk-taking and informed decision-making. His candid reflections on both triumphs and setbacks provide listeners with a real-world perspective on the complexities of investing in today's fast-paced startup landscape.

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Transcript

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0:00I mean, we made a ridiculous sums of money for LPs in that period. We were the largest shareholder of Coursera, $800 million back to LPs on Coursera. We made a ton of money on Lyft and we lost money on Uber. 40 % of my third fund went into Spotify. I went back to our LPs and said, listen, we fucked up. We need to pivot. We need another 300 million bucks because I need to protect this thing. The next three years were some of the worst of my life. This is 20VC with me Harry Stebings. Now stay with me, one of the most nut stories in Vansha Capital. I went for a walk with this guest before the show, and it was just mind blowing the different elements of their journey.

0:39So we dive into it today and I'm thrilled to welcome Larry Asherbrook, founder and managing partner of G -Squad. In what is, as I said, one of the wildest stories in Vansha, Larry started G -Squad with nothing, dialing for dollars, having personally invested in like Twitter and Uber, and then in his his first fund. He made sizable bets into SpaceX, Palantir, Alibaba and Twitter. He also had mega losses along the way, which we discuss in the show in Get Here, 23 and me. He had a lawsuit with Theranos to get out of an investment there. And today, he manages over $5 billion and he's invested in everyone from Wiz to Spotify to Revolute nantropic, this is one of the best shows I've ever done.

1:22Because Larry's so honest, he's so real, and he's very candid with the numbers. This was an incredible show. But before we dive into the show's day, I love seeing the team come together to make this show happen. What I don't love is trying to keep track of all the information, the data and the projects that we're working on across dozens of platforms, products and tools. That's why we use Coda, the all -in -one collaborative workspace that's helped 50 ,000 teams all over the world, get on the same page, offering the flexibility of docs with the structure of spreadsheets, Coda facilitates deeper teamwork and quicker creativity, and their turnkey AI solution, the intelligence of Coda Brain, is a game changer.

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4:50Larry, did we water on the park? and I heard your incredible story and to be fully transparent I didn't know the incredible story before which is why at the end I was like dude we have to do a show together so thank you so much for doing this with me. I think that's humbling you know it's sometimes difficult to open up and tell the story but I enjoy it at walk. Listen it's the short shorts and the great legs that make you feel comfortable to open up I completely understand. But I want to start on the entry. Diling for dollars is kind of how I was thinking about this. How did you start your way into venture?

5:25And what was that entry point? Yeah, for me, it wasn't really, hey, I want to be a venture capitalist and manage billions of dollars. I come from nothing. It was a fundraiser for academic institutions for their endowments. I was good at that. And everybody I raised money from. Most of people, not everyone. Most people made it investing in private companies. These would be at PE funds or venture funds or running their own operating businesses. It didn't matter what it was from windows to financial management to PE. They created real wealth for their families. And I was like, they're not that much different than me.

5:56I work hard. I'm smart enough. Maybe I can do it. So I went back to business school late in life and our business today was my thesis. And I started buying, you know, the smartphone became something that was running our lives in 2010. And I just started saying, this is super interesting. Why don't I buy shares and I have a follow -up Twitter. I like Twitter, you know, what about early Uber? What about early Spotify? And I just started buying shares from my classmates with my own money. That sounds great, but these companies are not public at the time too. So how does one do that then? How did you approach it?

6:28Well, I guess it's not knowing what you don't know is in ignorance as bliss is kind of the same thing. I didn't realize it was something you shouldn't or couldn't do. I just asked people, you have shares, can I buy some of your shares? Well, I never really thought about telling them because I really can't sell them. How would you buy them? And still to this day, 15 years later, there's a form that I created at Carrey School of Business at Arizona State, one page form that then we sent to the company to buy stock. And it still floats around. I got it back from a broker not that long ago, and it's like literally the form I created in 2010.

7:00One page, and it's binding though. That's scary, it's binding. So which has bitten me in the ass a few times. So we're at business school, and we're like, you know what I see in my mobile revolution? I'm buying Uber, I'm buying Twitter, I'm buying Spotify. What happens then? And also, how much are you buying? Yeah, so small, you know, I wanted to make a change. I was working in college athletics. That was changing as it's become today. You know, this whole thing, players should get paid and coaches salaries and pretty soon the inmates were running the in -silum sort of speak. And I was like, this isn't my passion.

7:34That's not where I came from. I want to make a change as a former athlete. Like, maybe I can use my brain, not my bra. I cast in my retirement. I went through a divorce, got remarried, had nothing, had no money, and I just had paid the tax on my retirement, started buying these shares. This is let she go lost money. Yeah, well half a nothing's nothing. My wife came to our marriage with $50 ,000. I had went through a pretty tough financial situation. Rightfully so, my former wife kind of took what I had, raising my three young kids at the time, and my wife and I today, we started a journey together.

8:09And she backed me with the 50 grand in my small amount of retirement. I just started buying Twitter shares and Alibaba stock from Jack Moss family office and then holy shit, it worked. And you review those today, which was the single best investment on a multiple basis. I mean, Twitter and Alibaba were pretty good. Those were when I realized there's something here. Making a little bit of money in your whole life, working 10 years in a profession, thinking you've kind of made it coming from a group in an orange trailer in my new talk. You know, having like a hundred grand in your bank account one random Tuesday felt pretty good And I said this is something interesting and I got some advice You should raise some third party capital and that's what I really understood the power of OPM other people's money I went around all those alums who basically I think gave me some money because they were tired of me asking That I worked at five different large academic institutions and so just so I get it right And what was the thesis?

9:04For me, it was very simple. If there's fewer institutions to help companies go public, coming off the financial crisis, funds started deploying large sums of money. So then the byproduct would be companies would stay private longer. The average age from inception IPO was like three years leading up to 2010. From 2010 to 2018, it got to like seven or eight years. Today our average portfolio company's 15 years old. So there was to me something that was clear there, which was there's an opportunity to buy shares from these people have no liquidity and you should be able to make more of a return than and also companies wouldn't return my phone call frankly because I had like no money and hey Twitter hey Dorsey my name is Larry Ashbrook I'm a retread athlete that wants to become a venture capitalist can I invest in Twitter and by the way my fun sizes I don't have a fun I just have like 200 grand in my name I'd like to buy $10 ,000 for the Twitter stock That conversation obviously wouldn't go anywhere so and so you have this moment in time when you're like hey You're seeing this the establishment of private markets was seeing a lot more capital flow in and so you go out on Fundraised for the first vehicle how big was the vehicle?

10:12Three years 35 million dollars deployed along the way. Well, it was three years to fundraise. Yeah, three years 2010 to 2013 13, 34 million or 35 million and deployed the money as I raised it. So you did multiple closes? Oh, yeah, multiple. What was the first close? I don't even know how many, a couple of million bucks. What do you advise founders on closings? And it sounds strange, but like, you got different advice, close as soon as possible. 50 % one close founders for companies or founders for new managers. New managers. Well, first of all, if I knew then what I know today, I'm not sure I would start the journey because I didn't know how hard it would be, I just want to do something different with my life, try to create value for my family and try to set my children up for a different future than I had.

11:01I was lucky. I grew up, my siblings grew up in the same house as me. We don't have the same life today. I got out of the squalor because I could run and throw and catch. My siblings didn't have that benefit. I didn't want my children who knows what their outcome would be. So the whole genesis of it for me was to try to create something and seeing opportunity being capitalized on. So with my mentality still to this day, raising billion, two billion dollar funds is the monies there, you close, start deploying it, build a portfolio, show some improvement in nav. It is inertia that makes it easier.

11:35I don't have the benefit even today with the returns that we've had and the DPI we've had to say, Hey, I'm raising a new fund and have two billion show up in two months. We don't have the benefit of that. I'm okay with that because I think the way we were forced to raise money makes us better now 2021 It was very different. I was set up my farm you sat in your underwear probably and raised in three months You I don't know what you raised 150 million bucks We raised a billion four and then turned down another 700 million in very short period of time and companies by the way also raised a ton of money insane month numbers We're gonna get that but I wanted to tell the story before we move into like that It's just such an amazing sort.

12:15And so when we look back at that, okay, so it's three years, 35 million awesome. What was the first big mover in that portfolio? What was the real momentum? The real momentum happened in 2014, and that's when I really felt the power of what I was trying to do when Ali Baba goes public. And you had that in the fund? Yes. But shares from Jack Mars Family Office, and wow, what a creator of Shareholder Value Jack Mar. I'm sorry, dude. How do you get in touch with Jack Mars Family Office to buy shares from them. I mean, that's the story of my life. It's like, you know, it's a bit of luck. You meet, I alum that I knew, knew somebody that knew somebody and kind of introduced me to gentleman's name was Barry Purcell, who was running Jack Maas money in Virginia of all places, I believe.

13:01And he said, hey, we have some shares to sell. I'm like, okay, hired a group in India to do some D .D. because I had like two people and wrote me an investment. Oh, yeah, my early investment committee memos in the early ventages were outsourced to a group of really smart analysts in India that you could pay a fraction of what you could pay talent in the US. I didn't have any money to invest in talent. And that's today is what Simon Altman does with deep reason. Okay, so yeah, Alibaba was the for me was there's a business here. It was grinding grinding grinding. That was the first one that was material for me as 2014 Alibaba.

13:38And are you putting size into these? Yeah, so from the beginning again, you don't know what you don't know. I didn't like the idea in my personality is kind of you go big or go home. I didn't like the idea of trying to manage a lot of these positions because I didn't really know how. So my idea was I wanted to put a little bit of money in, understand the businesses, and then pick a few and put all my money in. Today, we call it land and expand. We have all this bullshit that we say that our marketing team, our team is second to not. with their new reserves heavy model, but with diversified on that.

14:11So it sounds like that. But really for me, it was all fewer companies, because ultimately, how do I get liquidity if I have 50 companies? I don't, it's my money. I don't have much. I've got a few people who trusted me. I want to get their money in and out as quick as I can, because as you're trying to raise that fund, and you know what it's like, people want track record, they want pedigree, you know, what's your TVPI gonna be, what's your moik gonna be. I had people who were running their own businesses give me a little bit of money and say, I want the money back quick. I want optionality to it.

14:41So from the early days It was how can I build a strategy that I can actually make a good living at to have velocity of the capital come back and Optionality and today our business is become that and the early generation of it was start off with little checks I didn't have much money as I raised more money the challenge of raising the first Ventages the benefit of that was you didn't have a lot to deploy So I'm deploying it as I have it so inherently I'm doing this land and expand without even knowing it Then you look back at the returns and you say, holy shit, it works. Starting off with a couple small checks, all of a sudden you keep getting the data and I'm sending it to us to my awesome group in India to give me the data back.

15:19I'm sending it over there. Hey, it's amazing. You work 24 -7 time zones. But anyway, what comes back is, hey, these five companies are better. And so then what I did is I put a lot of concentration in and still to this day, which some people are not comfortable with. Hopefully 90 % of our risk are in 10 companies. So when we get back to that first study five, that's how many companies sort of give or take like seven seven companies But most of it is Ali Baba. This is funny. This is just dumb luck. Come on. I'm not that smart. Ali Baba Spotify Palantir and Twitter

15:59But I actually can't get that lucky and so you have to actually be because if you just did one I would it but what all those having common right and now you look back and say well how do you do that right and There were some dogs in there some clean tech shit that client perkins sold me that was just a flaming bag of Tards on your front porch like look at this guy. He's energetic. Let's give him some garbage You know and that's what the old line see Silicon Valley firms did in the beginning. Oh, yeah, we'll let you in this Syndicate sure how much are you putting over putting in very little but our LPs are co -investing a lot.

16:31That's an alarm bell. Now that you know, it's ringing as loud as like a four alarm fire. When Doug Lee or Nick Kuzinger's, I've got something just for you. Just for you. You're going to love it. You're going to love it. You're going to help your first time manager. I really want you to succeed. So what are those for having common then T when you look back on them and reflect the timing of that period? No liquidity, large private valuations, really differentiated, unchallenged business models. No one was doing anything like them. The liquidity window was just was still early from the financial crisis because you look at the number of IPOs from 2010 to 14.

17:07There wasn't many. It was a pricing premium applied to them. And what I mean by that is if you think about that applied to say your space access of the world or you know which we had in our third vintage. We can get to that. But like there's a pricing premium on it where you're paying an exorbitant price for that defancy and for that mode. But yet today, then there's no options for liquidity. It wasn't that. It was, you actually could get really good value. And I think one of the interesting things about the cycle we've been in the last 15 years is, you know, now we look back at the funds and dissect them and say, what kind of value did you get as being a secondary direct buyer?

17:42It early vintage is, we get like 35 cents on the dollar by being a secondary direct buyer over primary buyers because there was no other secondary buyers because the water reasons, sure, get myself a little credit, hard work, drive, run through a wall, regardless So how thick it is and just keep hitting it until it falls. That's my mentality, which is good and bad. You're really leaving the bro and not brain department. Yeah, right. I'm trying. I'm just running through. Running through wall. It's there. I think that early ventages up until 2020, all of those ventages, you were getting a lot of value by being a secondary direct buyer.

18:16Now, that's a key differentiator. What I wanted was and still to the state what I want is I want to touch and feel the founders, the companies, the data, I was amazed by what I started. The paradigm that opened for me mentally was something that I'd never tapped into my entire life. This was really interesting what these companies are doing. Do you think your business model still applies today when you are so detached from the data and the founder at the level that you're going in now to a lot of these secondary businesses? That's the misconception of what we do. I love it because it actually is when a good LP, the light bulb goes off.

18:53They realize that it's the opposite of that. We get primary level data. We touch and feel the founders because the value of the discount is back and they value the work that you do today because they're still a massive need of liquidity, but they want a trusted partner. And that's part of the journey to how we got here today is by doing something different. But sorry, the value of the discount is back. Are you kidding me? No, it's amazing. No, no, but for the premium assets, you're coming in at cost. not always, no. The market on direct secondary buying is really fragmented. So first of all, in the US, you have to be regulated a bit of a different way than most fund managers to do it in quantity.

19:32Which is RIA. Yeah. A fully registered, kind of like a hedge fund. So you're seeing a lot of people opt into that? Why? Because they want to pair primaries and secondaries together and they want to do some one -off secondaries big checks. One of the things from the early ventages that teased out that we still do today, It was the frequency of transactions and touchpoints of really micro transactions sub two million dollars Let's say today on a two billion dollar fund give you a lot of interim data that you would not normally get in that touchpoint As a primary investor it starts to provide you that Trojan horse moment to know when to triple down on a whiz Which we did in our 20 22 vintage fund and have the outcome that we're gonna have those founders are amazing but to make 3x in 18 months is because of what they created, but the opportunity to do that is because you offer something different than others.

20:21And that's to the people you asked me a question earlier, if you're going to start raising a fund today, what would you do? Yeah, raising money, don't take no finance or open every door, all those things to employees you go, but also create a firm that's different. The world doesn't need just another early stage seed manager, growth manager, crossover fund. There's so many. Dude, I agree. I agree. That's why we have media companies that trust. But trust is very, very difficult. It's your differentiate your business by sitting here and doing this and in the know and how many awesome people do you get to talk to to find and get the references to the next great thing you have figured out a niche most don't most say oh you know I worked at XYZ old logo firm for 10 years and I know how to operate I'm gonna start a VC firm I'm gonna go to 10 LPs that were in that old one that I got to know and give me some money and they fund them and they fund them I mean, they really do.

21:12I was really fond of you. Like, right before this night, we love the spin outs. Yeah. You spin out of Excel or you name your big firm and we fund you. Great. And that also provides the ecosystem for us to operate it. I want to go back to the four names you mentioned. How do you get a Spotify? What's the story there? I love Danny. He's one of my oldest friends. I love Shack as well. They all special. How do you get a Spotify in 2014? So one of the first employees I hired, young guy at a Berkeley, he's now my co -pump, Spencer McLeod. He's a living caricature of what Silicon Valley is. He was working as an analyst with me.

21:45This is like 2014. I think he's like 22 years old at the time. I was telling him this story about how my mind exploded when I was in college and I could download Metallica on Napster. And he's like, you know, you've heard of Spotify, right? And I'm like, yeah, he's like, well, maybe we should buy some shares and Spotify. And literally that's kind of how it started. And we started searching around and we found a celebrity that was going through a unfortunate change of life scenario on a divorce. They had like $4 million a stock and we had a $300 million fund at this point. I'm like, yeah, let's buy it.

22:15Well, Spotify had this interesting process of how they approved shareholders. It was kind of onerous and difficult and my mentality was they're not responding. So let's go see them. So literally Spencer and I flew without an appointment to Stockholm. My wife came. We spent a week there in the terrible Northman like November. We had a which became a great investment for us later on. But anyway, we started going to get a meeting. And finally, this young lawyer, Peter Grandilius, took pity on us in the waiting room and took a meeting. And we pitched, I look back and all the pitches I ever gave a company on how we could add value with a small fond and a lot of co -investment spotifies what it's become.

22:56But they're like, yeah, we could use the help. Very humble, very nice people. They introduced us to a gentleman named Johann Berkuss who was at the end, I think the treasurer and then went on to Bolt, where we also became an investor in the EU -ride -helling business. And before we left the meeting, they were like, do you think you could buy $150 million worth of stock? And I said, sure. And I didn't have the money, because we were in the process of raising the fund. And I think we had like close on $125 million. I'm not, I've even done the diligence. I've even done the diligence. Yeah, by this time we did do diligence, we'd written a memo and, you know.

23:30But those diligence, those diligence, those diligence like the 20 million, this was more than a theory. So most of the early stuff had to be mosaic theory because companies until really Spotify. So the early wins are gathering data, trying through public sources, but it's not really available. You're trying to gather through contacts and putting as many feelers out and then sending all this information to what became our own research team to develop a thesis around it. And then the Trojan Horse became the check to get the info. So in that land and expand and strategy that we run as it's developed often that first check is kind of that Trojan horse.

24:06You like it, you've done some mosaic theory work, you think it works, but you don't really know, you go in. So we go in, that give us a whole deep dive on the business and it's amazing. It's like nothing I ever could imagine. It's nothing I've seen before. Why so? Why so? What was it about it? It was made as a... At that time, the penetration of the user ship and Sweden was like 25 % of the population used it. That's amazing. 25 % of the population used the product. It's already cool because you're using it and of course Apple Music and I think the beats and title and all these, you know, soundcloud, all these competitors.

24:42But what they divulged to us in that one -on -one personal meeting after saying no to us for six straight days was the fact that the record labels were also investors. That to me was like, this is like Napster on steroids and it worked and obviously they went on to create amazing shareholder value. It's one of the best businesses we ever invested in and we had 150 million dollars to go find. So what do you do then? They're like, hey, you get 150 million dollars. Are you shitting yourself? Yeah, yeah, because I said it 150 million or none. Yeah, so the way that the transfer process worked on that business is pretty interesting.

25:16It actually gave you time. So you signed the documents today. It took like 60 days to clear. So we had like let's say 25 million ready to go awesome concentrated position on a 300 million dollar fund We're gonna start let's do it. We had four million. They said yes to we'll take another 25 So we went out and went on a world tour with our thesis Spencer and I different countries How long did you have we had 60 days? It's 60 days raise 125 and we got to day 59 and we had sent 141 million to one of the earliest investors very predominant Norwegian fund will leave their name out of it awesome founder of that fund who is an iconic pop star or sorry metal heavy metal star and music in his own right very serious guy and we have a hundred and forty one million dollars we've sent them and the rofer ends and if we don't send them the nine million dollars deal blows up and I don't have nine million dollars to my name so I borrow it from them.

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26:12You borrow it from him? I love the nine million bucks from him. You cool him up I'm so sorry. I don't have the nine million, but if you lend it to me, I'll close and I'll pay you back and he's like sure I'll lend you the one exactly that pleasant Harry, but it worked and God bless my wife She's like you love this business. I'm like it's the most amazing business. I've ever seen she's like well How do you how do we figure out how to own the nine million and we figured it out and that nine turned into a very different Number and that was the life changing event for me Spotify buying into our business model We then went on to become a top 10 global shareholder of Spotify.

26:46When, as far as to putting up signs in their break room, we'll buy your shares, buying all these odd lot transactions along the way, and build a huge position. And it ended up being like a billion dollar outcome to our LPs. 40 % of my third fund went into Spotify. How much was that of the phone? 380 million. It was a lot of money. Very concentrated risk. What price is it going in? It just kind of give a take. Yeah, so in many ways we did it at the time in which it was perfect because you had a Dell announced she was leaving the platform. You had Apple music taking market share and you had Taylor Swift saying I want my library off and Daniel Eck came out and I think one of the smartest things he's ever done and he agreed with the artist.

27:30He said, I have your back. I understand why you pulled from our product. You're not the issue. And the record labels had an option to buy more shares and they executed the option to buy more shares So to me that was like there's this auh -ha moment where we can triple down Nobody else knows this information You buy from all the people who were scared to death and you do the counter intuitive thing and you take the bet And we did and it worked and we bought it like a 50 % discount to the current financing round and we just kept buying it there For the next two years so off to the 150 kept buying we get yeah, we kept buying So we pooled a bunch of money together.

28:05Some of it we were able to put North Fund others. We had very prominent Very very prominent logos come into our SPVs to buy the stock because we had we locked in the access So you have this journey you start yours hustling you get to 35 million the second fund was 36 million raise it in a year on a million increase Yeah, one million increase Yes fewer investors Thank God and then you get to a $380 million dollar pool of capital. And in that, you take a lot of concentration in Spotify. But on top of the concentration we had, we did another 700 million in co -invest. In Spotify. In Spotify. 700 million.

28:40Yeah, I know. But that fund also, by the way, that fund also had lift, Uber, SpaceX, Instacart, and possible foods that list goes on and on of companies. Because of Spotify's acceptance of our model, It opened up the door. It opened the door. And Johann Berquist and Peter Grandillius, they're the two people that have made probably the most direct impact to my life because they trusted that we could do it. And they put their names on the line to Danielaek that we could actually achieve it. And then we went in somehow, you know, Spencer and I spent support, I got shingles. He literally got shingles.

29:19He was like 23 years, four years old, got shingles. I never even said funny, because Daniel's like the guy who I just send rude memes to in most mornings. I mean, it's an amazing business. It's truly amazing. No, he's absolutely incredible. When you go through those names, what about Uber? How does that come? Often in our thesis, we'll back to businesses trying to attack the same thing. Lyft and that fund became the value play. We sold it and we made a ton of money on Lyft and we lost money on Uber. What? Yeah. Well, how does that work? When Uber chose to go public, it was a tough time. Today, Uber's valued off a gross profit, which is, I think, a good metric for them.

30:00I don't think when it went public, it was rewarded properly. In our business model, we don't hold rarely. We hold post -public. Oftentimes, we sell before their public. As it went public at the price it did on a converted basis, we were under water. We lost like 20 cents on the dollar and lift we made like a 3X. How much do you lose on Uber? I don't know, 50 million bucks probably. And you made a three -axle lift. Yeah. Yeah. Because you sold before the IPO. We sold most of it before the IPO. And we won't talk about the names that, that buy. But you'd be surprised. I think one of the issues with Silicon Valley, one of the benefits of being in Chicago is we isolate ourselves a bit from the herd mentality.

30:41Sometimes it's like sheep. They just jump one on after the another and they buy more stock and things that you see that you should sell. and it just takes one brand name to jump on board and 10 others jump on board and we just kept selling our lift stock to others. You know, I get why they did it. It was a value play compared to Uber and it went on to work for them, but we made our multiple and went home and distributed the cash. Do you think it's very clear when rationality leaves the room? Yeah, that's something I've spent a lot of time in the last few years trying to figure out because 2021, 21 all rationality left the room 2020 2021 and and us like everyone else just kept deploying capital But it left the room in public markets to the multiples were off the charts.

31:22Yeah Everybody left the room. I think you know you want to I told to play the game on the field as Bill Gurley sets Yeah, a few things about that period that is the rationality leaving the room that you want to protect yourself Guard rails are important a good friend of mine And I know you had them on the show I'm a huge fan of what they've done Mitchell green It's best things in life are copied in some ways. You know, he has his lead edge eight. We have our G squared eight. Sorry, Mitch, we kind of borrowed it from you. Is it the same? It's not the same. We had to really adjust ours after 2021.

31:52It had holes in it that were exacerbated. What were the holes and how did you use it? Too much qualitative. Too much my gut, my feel. Too much who else is in the room. Too much the soft stuff that venture capitalists growth managers like to pride themselves about. In our strategy, it has to be about the numbers. It has to be cut and dry, cut throat. Does it work financially or not? Because at our stage, unlike yours, it'll always envy your seat. Because if you pay 50 pre or 100 pre, if it's a good business, you're still going to make a 5x. At 10 pre, 50 pre does it really matter for you? Maybe for me, is it 3 billion or 2 .5 billion?

32:33you walked that forward, I can't make my tune a half -ex net in a five -year period if I missed that. Now, I get an okay return, but I'm not rehired. Does your mindset change around that when you see the elasticity of outcome sizes that we have today? I completely agree with you in a normal world over the last five years, but when you have companies that are hitting a trillion, a trillion, five, two trillion, dude, who cares if it's 10 or 15 billion? Yeah, I think that that's in a shorter thesis you're able to play that game, and that's one of the benefits to our thesis is yes, is longer you don't get caught at the end of that cycle, which happened in 2021.

33:07So our earlier vintage was selling into it, like it was happy days. Did you just offload just massive amounts? I mean, we made a ridiculous sums of money for LPs in that period, which set our business up to be able to survive a bad vintage. And we're working our tails off, our asses off on our 2020 vintage, but it's hard. When you're shipping a ton of money back, LPs happy. Yeah, I think LPs are happy. It's also their expectation. Looking for a pat on the back because you did your job is something I talked to our team a lot about. Yeah, it's a big win, but hey, we also lost $400 million of their money over here.

33:42Yeah, we made them money, but look at these losses. How can we lose that kind of money? I think keeping our team focused on that and reducing the amount of mistakes, because in a short fun life, liquidity is already hard. It's really hard as a fund manager as you know. You're five to seventy a fund life, aren't you? Yeah, with some levers, we can get it a bit longer, but you know, for the first time, we've had to pull one of those levers and it really guts me. Is that a mistake on your behalf? Or is that a changing landscape? You are what you become sort of speak? Yeah, are there businesses that I would love to take a 10 -year horizon on?

34:19Because I think they're amazing companies. Yes, 100%. But that's not what our LPs have hired us to do. They have hired us specifically for this North Star DPI statistic that I've pitched them on and our team have pitched them on and for 15 straight years So cross -subventages they hire you to make the most money for them And you can go back to them and say listen the job of a manager is to change to moving markets And I believe that yeah actually we will make more money for you with our longer -hole period because of X Y and Z reason Yeah, I think then you now have the data I'm so sorry to interrupt you I don't have to go face it to go look at Palantir.

34:54Look at Spotify. Oh my God. Why so very, just face it. Even if I would have held Palantir for three more years. I mean, who knew they would go out to build this whole money, would you have made it? Oh God. You know what I'm hearing? We would be having this podcast in my bubble and outer space. But is it like two hours more? Oh my God, no, it's like I had an LP, long time LP, first vintage, bent back every time. I was talking to him the other day about the difficulties of our 2020 ventages and the lessons learned and how I'm more energized today than ever before and how, you know, we're going to make it up in spades.

35:29And he said to me, you know, Larry, you get a free pass on that one. You made me, because I distributed the shares to some of our early funds. We distributed shares. We no longer do that. We just sent cash. And he's like, I held that Palantir stock. And I've been investing in every one of your ventages is from the proceeds of my first 50 grand I gave you. So it just gives you a perspective. I think we made a three X on it and sold it at $9 a share. What's it now? Oh, I don't know. I tried not to look at it because it's one of those things is you don't wanna inflict the self -inflicted wound of the pain, but I think it's, I don't know, it's 80, 90 bucks a share.

36:03So my question to you is, have your guardrails not now become a constraint? A negative constraint? Yeah, look, I think the answer to that is we're doing what we're hired to do And that is to generate the velocity of the capital for our subset of LPs that's not for everybody. Our LPs are looking for an ability to play the fastest growing most dynamic technology companies in the world, and they want to get in and out with optionality of their capital to give more to firms like yours in every five year period. So if they back to back funds of ours, they make a Forex cash on cash return in 10 years, but they have the optionality of it.

36:37And if you have confidence in the mouse trap you've built Forex in 10 years, cash on cash return. It's pretty hard to beat. Do we all tell these big numbers? Look at the real numbers. I've seen them, you've seen them that very different in reality. Yeah. I mean, when you're North Star as a DPI figure, there's no hiding. Listen, let's go to the 2020. You said they're about, hey, you get a whole pass. I said to you off for a walk, it's really special to actually have the conversation that we do. And I'm really manic. The candidness is important. When you look back now, what do you think your And I've talked a lot about this openly to our LPs because I take pride in going around the world And we have 60 countries and six continents of LPs and it was smart in my opinion when I started the firm It's difficult now the main mistake we made was believing our own bullshit because coming up to that point We had some of the best returns in our industry.

37:31We were raising money It didn't we just to put the flag out there was hard. We go around raise money Co -investment, raise money. Life changed dramatically for my partners, myself, our team. Just to ship back 2018 vintage fund, by 2020 we had the DPI to almost one. Oh yeah, Airbnb goes public, make a 3X. Coursera goes public, make a 3X. Sell our space X stock privately, make a big return. Impossible foods make this huge return. Impossible foods? Oh yeah, we made a killing. How did you make money on the market? The herd mentality. I mean, I think that it's all a product of the time you're operating in.

38:05You go back to that period and possible foods was a big deal. People made a ton of money on that, beyond meat, and what was the other one that egg company in them? One of my best friends who made like $10 million was gonna be on me, SPV. See? And I'm like, $10 million was the market company today. I look at the big wins that where the market cap goes in a bad way is, we were the largest shareholder of Coursera through our strategy. We owned 16 % of Coursera when it went public. What did it go public, huh? We sold the stock at $36 bucks a share, and it's at $8. $800 million back to LPs on Coursera.

38:38$800 million back to LPs on Coursera. That's part of the strategy where you get the concentration and the law of large numbers actually works since easier to manage a fund on liquidity. Beginning in 2020, the mistakes we made, so you had all these exits. Toast was our largest position in that fund. It's trading at $76 bucks a share. Mitchell Green and I did toast together. It's like you're popping champagnes around the office. You're like, this is, we're so smart. We're the fucking smartest people in the room. And then I'm on a ski lift in Montana and I'm looking at it. Unfortunately, and I'll admit it all out.

39:08Yahoo finance. It was before complexity. It was before, before complexity. And I'm like, wait a second. Toast is 76 bucks a share. What the hell? How is it? $76 a share. It's a great business, but 76 bucks a share. Whoa. At the time. Now, toast is an amazing company, right? Revolutionized into the restaurant space. And by the way, saved tens, thousands, hundreds of thousands of jobs in the US because of the way they pivoted during COVID to help restaurant tours. An amazing business, great founders, all that being said, it wasn't worth as a public company that price. So to me, that was kind of the canary in the coal mine.

39:44And I started freaking out, because we just deployed $900 million between, you know, beginning of COVID in 2021. To your point, jumping on board with all these primaries and secondaries, we're super smart. We can do some primaries too. So what was the realization when you saw toast to say that I have a problem in this vintage. We've overpaid for all of it. All of it we've overpaid. Go to the team and a lot of them aren't with us anymore because it went through a kind of identity crisis and said, listen, I had went through a period where I wanted to believe that our firm was more than just the co -PMs and Spencer and myself and that we could do a traditional model because we don't do that.

40:26We deploy the capital between the two of us, we have a research team that supports us. It's more like a hedge fund. It's quick decisions. But at that period of time, we're like, hey, we've made all this money. We're growing our business. LP's are coming aboard with big checks. They want to chase Moic. They want to chase TVPI, right? We have to have a thesis that's a bit longer. Seven years, not five. So let's divide the capital up amongst a bunch of people. Let's build the traditional fund model. Because we're so smart. And you know what, we're still conservative. So we're going to pay 12 times last 12 months to enterprise value on SaaS.

41:00Public markets are trading at 25. Pet yourself on the back, guys. We're super smart. Oh, the floor can't be lower than 10. That's a historic multiple wake up in 2025. The multiples four. So when that happened, when a really awesome business, which we made a ton of money on by selling it at the right time and harvesting and they're in toast and they've went on to We created a tremendous amount of shareholder values in public company. Don't get me wrong. When it's trading at this crazy multiple, I went back to our LPs and said, listen, we fucked up. We need to pivot. We need another 300 million bucks because I need to protect this thing.

41:37And so we went in and we did structured equity deal after structured equity deal. As that market's falling and the house is on fire, we're running in the front door with cash. And we're going and doing minimum IRR deals. We're partnering with the super savvy investors and the light speeds and the dragon ears and the DSTs of the world. And we're doing deals that nobody knows about third point co -2. And we're putting all kinds of structure in where these founders believed their own bullshit. And they said, all take the high price top line, but all embed structure in the equity. And so that vintage of all of our advantages has 70 % primary and 40 % of that has structure.

42:15For people that don't know what does that mean. It means you embed IRR hurdles and multiples in the paper. So regardless if you say the business is worth $8 billion on paper, the company has to generate you a 25 % IRR or a 2 .5X, which ever is greater. So every day, the returns ticking. And you walk it out now five years. The entire pref stack is totally fucked because we the last money in has this ratchet that just eating up all the value. And that pivot and the willingness to I think our team, not just me, the willingness for for Spencer and I to get together and say, what were we thinking? We have to try to save this thing, our LPs trusted us with a billion at that point, billion five.

42:54But you'll go on the offensive with cash in the door whenever I was running out. Yeah. In terms of the actual saving, what are you doing with the overly inflated asset prices that you have? Selling. Selling your losses. Selling. Taking a different perspective on multiples and saying, you have to get the price to 10 X. So you're going back in an asset you overpaid and you're using the secondary market as a market's falling to lower cost basis. So we did a lot of primaries, yes, because we didn't like the secondary multiple because it traded at a premium during that period So if you paid 25x in a public company to enterprise value to last 12 months of they are an assas company privately they traded 50 and So you like shit the secondary market is over the end of the secondary market doesn't work my business model is broken and so you go to primary You go to primary you go earlier you do a lot of mistake hindsight the mistake I made was not having besides thinking where smarter than we are is structurally in our business not having the levers to pull.

43:50Because leading up to then whatever we did worked and you could get in and out in five years and make a 2x net, you're a hero. You just keep raising money and it keeps getting bigger and your amount, your wealth generation keeps getting bigger. So we're unstoppable. We're Tiger Woods in 2001. You start to create this persona that everything works and pivoting, it was a lot of soul searching. We had a large meeting. Was it difficult for you as a leader? Yes, it was difficult because I couldn't believe that I talked myself into it. Silicon Valley coach, me, a person I grew up in a trailer might in Utah, athlete, and I have to have a coach to tell me how great I am.

44:29I bought into the whole hookline and sink or bullshit of the entire problem in my opinion of Silicon Valley and started our firm. What is that problem? Losing focus of what you're hired to do and paying more attention to the lifestyle that comes along with being a money manager and the circles that you roll in and about the deals that you're doing and the money that you're managing versus at the end of the day, the actual value you're creating for your people who have trusted you with their capital and making a difference for your underlying companies. That's what's important. Not going to a dinner party and saying, I just invested in whiz or anthropic or open AI or Airbnb.

45:06That's the culture, in my opinion, that in Silicon Valley. And it's people deploying the capital that don't have the responsibility to sit in front of the LPs to explain the problems. It's a herd mentality that rushes in. And LPs follow, by the way. LPs follow at the wrong time. It's very easy to raise money in a crazy market like you and I both did and many other managers did when it's the wrong time. And it's very hard. Our 2022 vintage, should we raise? Very difficult to raise. How big was that fund? Billion two. Was that the first billion fund? No, 2020 was a billion four. So you went down in fun size.

45:40Well, the 2020 vintage, we topped that up. Remember, what was I was saying? We went back and said, hey, we've made all these mistakes. We have to protect. We need more money. And it went from a billion to a billion five. And the protection that was because paid a play was coming in. It was because we saw that we had overpaid on the first tranche of capital. So I wanted more to combat that with secondaries and also structure. So you hadn't lost faith in the unlearned sense? No. Some of them have went on to monumental failures that have been well written about, but most are really fundamentally good underlying companies.

46:12So when you review that period of 2020, what do you wish that you had done, or if you could replay the tape, go back to the first half or quarter or whatever your Americans like to go with timings and sports games. What would you have done now if you could replay that tape? Like I would say sit on my hands. You did not need to be part of that ridiculous 700 million in price round for 10 million a year or so. Yeah, that's the easy answer is, wait, if I could do it all over again, I would keep the control tighter to Spencer and myself on deployment. And that way, as we went forward, the only excuse we could have is that he and I made the decisions.

46:49We wouldn't have any excuses. It would be clear that we made the mistakes versus, hey, we tried to do the Silicon Valley mentality and hand out the capital and build teams underneath. and yeah, it's the G squared logos that we invested in, but the attribution actually goes to X, Y, and Z. You don't like how to reach them? No, it causes unintended consequences. People want to pat themselves on the back for the wins and deflate the losses, and deflect the losses, excuse me. If you wanna build a firm that stands the test of time, the logo makes the investment. It withstands any transition period and any leadership role in the firm because the logo made it, not the individual.

47:30That's what we're trying to build a G -squared is when I took out 20 years from now and say, where do I want it to be? I want some grandkids to think about the logo that was built and say, my grand pop built that and it's still there and it's the Jim Simmons 40 % annualized IRR for 20 years. Did this what I always say that about my grandchildren? I didn't have children yet, so it's really quite a step. But we mentioned lessons on a company basis. If you look back at one of yours that was a big loss, what was your subsequent lesson from that? Well, we've had a lot. In that concentrated equity portfolio, you're going to have some monumental misses, hundreds of millions of dollars.

48:09You're going to light on fire if you have the four to two to stick to it. So we've got a lot of those lessons to draw on. It was the one that most painful. There's a couple. One is Theranos and the other is 23 in me. How did that or something? So Thera knows secondary. The big lost air was for me personally. We signed up to do a secondary at a really good price, met with management. Something didn't feel right. Don't know what it is. Can't say that I was like, oh, it's a great gigantic fraud. I didn't know what it was. Did you mean the Elizabeth? No. The kind of C -suite out without her. Something just didn't feel right.

48:45We went back and we had that form I told you about. Binding to transact. Oh no. One page. One page simple companies love it. It's easy things to change on it name shares company dollar amount binding transaction So I ripped it up and I got sued to finish the transaction and I agreed to settle where I would pay a Fraction of the transaction cost, but I did it personally so our LPs didn't have to go in what that taught me was Before we signed that paper we better be certain because it cost me a few million dollars at a time where I didn't have a lot of money And I did it so that RLP didn't take the loss because that was one of those spider -sense moments where it's like to years You're saying the risks were tangential to the data And my wife would say if she were sitting here She told me that it couldn't work because she's an epidemiologist and they collect blood and saliva and you can't you can't get that much data from Whatever she was the one saying I feel amagic She's like she'll sick Yeah, she's like that that doesn't work Long story short, the spider sense came up, going through negotiations, get out of the contract, and then some of the materials started to come out and we just like, hey, we're not doing it.

49:55And then actually, I don't think it was formally sued. It was threatened to be sued. And I agreed to settle it out of court and gave them a couple of million dollars to go away. And obviously it went on to be, you know, one of the more notable frauds of the time. But that was painful for me. That was bad process, bad outcome. Sometimes you can have bad process and good outcome. Sure, but what that taught me was you just need to have a good process and if the outcome is bad, okay, that's fine Which is 23 and me which we'll get to this was bad process going in this was jumping trying to jump on board Play the elasticity and pricing and follow the herd Especially the HUD that was not professional.

50:33No, it wasn't did that not worry to me I was chasing the discount that was available and the thought that if it just traded at what the last round was I made a lot of money. On the secondary side, that's what you're chasing, right? You want to get that disc value of the discount and you could get it in bulk. And I should have seen, I should have seen a lot of warning signs. That was a tough one to do due diligence on. I would say that added a lot of our check boxes that we now have to make sure that we don't make those mistakes again. And we really averted a massive issue in our business by doing that massive.

51:06What was the chat size going to be? The agreement was to buy about $50 million a stock over like four months because I'm still raising the fund Anyway, that's one of the biggest wins. I know I know Personally and personally it's not as I agree Yeah, but actually for the damage that it would have done to the bruh. Oh, it's catastrophic to us. Yeah If it would have mega win. Yeah, couple of takeaways They won was listen to your wife if she's around Hopefully she doesn't listen to this although I'm sure she will. Don't say that I'll love it. She'll say see Harry's right. She will trust me and the clips go viral.

51:42And two is when you feel icky in your gut. And one, the spider sense. Dude, I've had this and I'm not going to name the company yet. It's still going. We did a five million dollar investment. And I cooled up the lead investor. He was a very, very pedigree from this is off. But you still did it. I did. Now I don't fucking do it. Yeah. I'll pull out of everything. If I feel the egg, I feel the egg. Yeah, you go through this phase as building a business where you feel like you have some allegiances to some of the people that helped you get there, right? So you have a lot of investors. I need to far in.

52:10And you're too far in to say no, and you know you shouldn't do it. And we're humans. First mistake on you, second mistake on me. The one that's probably from a financial perspective, the largest that hurt. There's two really is 23 and me and get here. 23 and me, not selling. That was my mistake. When did you come in? First investment, 23 and me, and I think 20, 26, 17 really bought into the business model on the consumer side, loved it, enjoyed interaction with Anne, really bought into what she was trying to build and she really embraced our model to be helpful. And I was really taken it back by what she was doing and believed in it.

52:52And we built a large position in our 2018 vintage fund. I think it was the second largest position in that fund. Co -investment we have maybe had 50 million in and LP capital maybe 30 of 40 million in during the SPAC craze You know pair up with sir Richard Branson like what an iconic pair right you got and Mochikowski is a fantastic founder in my opinion Not maybe a great public CEO, but awesome founder and Visionary of what she wants build and the ability to go do it amazing Richard Branson on top of it awesome Let's go, but gasoline on trades 10 goes up. We can start selling at seven, which would have been about a two X I think I sold the last share at 70 cents That's me chasing multiple and that's a problem in our strategy You need guard rails and that to protect from Larry chasing multiple, which is what a layered approach to selling yes Dollar cost average out just like you dollar cost average in and just start getting liquidity when you can privately and Continuing it through when they list liquidity's hard How big was your position?

53:53In total, probably a hundred million bucks. A hundred million bucks, and you can do it to X. Yeah, and instead lost $70 million. Tell P's cool about that. No, the pool of the capital's awesome. It's just, you know, don't - It was the number one position in that fund. Toast, yeah, toast, awesome business. It's like 3X net and started in 2018. During COVID, Mitchell and I talking about it, Mitchell Green and I saying, this people don't get it, let's buy a bunch of secondary. Yeah, awesome. I'm on his now. Also, Asana too. We teamed up, Mitch and I teamed up on Asana. It was fantastic. It was just like you're conquering the world, you and your buddy, mind stock, people running out the front door cause their house is on fire during COVID and us running in with capital.

54:34It was fun. What about Gatir? Gatir is one, emotionally, for me, that's really hard. And I think about that good process, good outcome. You had good process? We had good process on the first money, gorillas. The investment in gorillas, we had good process. We had made a lot of money in the food revolution. We were in Instacart, we were in Postmates, we were in May, Twan. And just to be clear, sorry, because people would hear these names. You made money in Postmates. Oh, we made a, that's a Founders Fund special, man. We did a lot of work with Founders Fund early, fantastic group of investors there.

55:04I think Peter Teals got more money than God now. But yeah, they were the largest investor in Postmates, Sebastian Lehman, awesome guy, spoke at our 2018 LP day. Yeah, we made a 3X on Postmates. And how long? 18 months. He was amazing. And Spencer McLeod, he was my copia, he led that deal. And he was like, this, you got to meet this founder. He loves what we're doing. He wants to help all his employees. Let's do it. I was like, yeah, the data looks good, man. Let's go. And you made money on Instagram. We made a lot of money in this cart. We sold this cart privately during COVID. You're one of the guys.

55:37He sold it like the 25th. Oh, yeah. It's like, come on, Sequoia. And the price, he could sequoia, but yeah, it's a coil, make money and along around that. They He's also a bottle on the way. I mean, Sequoia's business model is fantastic. We have a lot of investments in common. Their partners are awesome. There's few evergreen structures I had ever invested in. There's as one. Why did you sell it 20 ,000? You just ordered it. Okay. Funny story. And, personally, you know, you have experiences with companies, very frustrating experience with the Instacard during COVID, where they went from Whole Foods only pickers and grocery shoppers, which was an amazing service, right?

56:11to then having your Uber driver shop for your groceries and try to get a ripe avocado and COVID from your Uber driver. It's not a great experience. And I remember a point, I'm hunkered down at my farm, the world's falling apart. I can't get the order, it's just not right. And they don't take it back. You just keep getting stuff delivered. And I was like, it's time. I just gotta get out. I'm sorry, wait a minute. So the fact that the Uber driver can't get you a fucking ripe avocado, you know what? I mean, I'm not the only one here. I'm not. I'm out. You know what we're going to sell at 25. And you do like a three -axle, right?

56:47Yeah, but it's also for us that decision to sell becomes somewhat easy, because we're also solving for something that's different than others. And we're solving for this philosophy of capital. It's not part of keeping in the middle of our to use a sports analogy fairway. Don't chase the mink. We make a 2x net in a five -year period cash return, not shares. We stop distributing shares because LPs blame you if they hold it. Don't you see you as a bit of a tourist, no offense? So if it's like if you want that short compression, you're not exactly a long -haul day. You're not a long believer in the company.

57:20No, we're a point in time problem solver. We're like the janitor that's cleaning up the mess. They have an employee that leaves that they're out there in the market making noise. They don't want them to take their shares. We get the phone call. You've got a fund that wants to show their LPs that there's value in the extension. They're giving them we get the phone call to buy a little bit of their position. You don't buy 100 % of somebody's position typically of company unless they're on year 15 of their fund and have no extensions because if it's a large position in their holdings in their nav and you buy it all, you kind of scratch your head like, well, why are they selling it to me?

57:52Yeah, but dude, I've had this before. I've got a great company and I want to buy some and I use charge it. And then Rurfa's happened. Yeah. How do you get around a Rurfa? That's the relationships. And in our business model, the companies and your peers have to see value in what you can bring to the company because what we're after is large concentrated positions. We're not indexing secondaries, buying with no information, playing the arbitrage in pricing and putting 200 secondary positions in a fund. That's not what we do. We're going to have 10 companies make up 90 % of our risk and we're going to become very large shareholders of those companies by doing our business model.

58:29And so it requires your peers to say, okay, they do something unique. They are going to provide value to us by consolidating the cap table. They're going to help us with employee structured tenders, shareholder tenders. We have an employee or a former share or current shareholder that needs to leave. They're going to buy it. And it's really the barbell of the small micro transactions that nobody cares about. Some of our companies, we've built through 50 transactions to get to $75 million. And some we've done for to get to 200. You have to sell that you're going back to raising money as a new manager.

59:03Be different. Be different. Because there's a pain in the ass to 50 transactions. It is. The muscle memory of that is not replicable for others. The back office you have to have the investment to not just pay yourself and to hire big teams to run it requires the ability for you to know that the actual outcome is the benefit of the carry, not the management fee. Going back to get here. Yeah. That one took years off my life. Good process. How did you come to it? So we made those investments and made a lot of money for LPs. get into introduce to get here by one of our excuse me to get real is we have an office in Zurich We have a team about 10 in Europe.

59:39We've been here since 2017 say hey, you got to meet this company in Berlin When I'm there this and we had a bunch of poor for the companies in Berlin at the time met the founders and the business was growing like a weed This is when it was in Tuck you know me. No, this was guerrillas in Berlin. Oh, this is good So we were acquired guerrillas was acquired by get here. Yeah, that wasn't a good deal it was. So for a group of shareholders, we were a part of helping structure alongside of five others, it actually was a good deal. We actually got good value for our money. We did get a little bit of cash and we got most of the preferred value in the transaction.

1:00:15So four or five shareholders of Gorilla's received of all of their shareholders received the majority of the preferred equity that we received from Gatir. So in a good place then, fine, Gatir valued at 10 billion. The next three years were some of the worst of my life. Why? Seeing that we needed to then try to protect that money with more money and then get involved at the board and do the heavy lift of restructuring and battles with the founders and we'll leave a lot of it out because it's still ongoing. But it was really hard and the mistake I made was the second tranche of the capital. How big was the first?

1:00:51A total first was like 50 million bucks in total between secondary primary. We got that plus sum and value of Gatier and then the next check was a hundred million bucks to restructure that equity to pull it forward So you get 200 million risk total a lot of LPs in it with co -invest of course everybody during that period signed up for you Just put it out there and did the con vass craze was fucking it was nuts in 2021 and and and created a lot of unintended Consequences that we can chat about but and different from our normal co -invest model we went back to from that period. But anyway, the log story short was, I think the major mistake I made there was not willing to just walk away.

1:01:31Off to the first check. After the first check. The fight that when you grow up in like severe poverty, you're fighting with your siblings for everything, you're fighting at school, you're fighting for food. You're fighting the world. You're fighting, you're fighting, you're fighting. And as you grow into business, that doesn't leave you. It subsides a little bit, But there's many people in our industry that have backgrounds like mine and you don't stop fighting. Is it a blessing or a curse? It starts to become a curse if you can't manage it. Because in that scenario, my thought that I could fight and will the outcome.

1:02:05Little OG squared amongst giants. It was like you were dead man walking without knowing it. You were already dead. You just kept fighting. And making sure that we don't make those mistakes again are important. And that's where guardrails other people with voices in your firm. Was it obvious that it was going wrong? It seemed like just an enormous amount of cash going into a business before it was ready and premature scaling and just the economy that didn't work. It seemed right obvious to me respectfully. Yeah, hindsight, it's easy to say it's obvious. I'm sure to many looking at me and watching from afar, it was obvious.

1:02:41For me, still hold it, I know. Yeah, we still hold it. it's now a business focused in Turkey and you know lots of great people in the business working and I'm still in the board It's all be careful some things I say but because it's a major major part of Turkey. Oh, yeah It's by the way that was the biggest mistake for me of the business It should just continue to And I think investors would say one thing founders would say another on how it became a global kind of strategy I think the mistake the company made there was it left Turkey and didn't focus maybe on other markets that were similar to Turkey from an employment cost perspective.

1:03:17Look, today it's still operating in Turkey. It's a big business. You got a lot of sophisticated people from a bottle in there working with the business. You've got people inside the business that want to win. You've got 10 ,000 plus employees that are working hard every day trying to create values for their family. For me as an investor, I lost a lot of money. Why I'm still involved is because those people that are commuting in some cases three hours a day to work in Turkey, they deserve a good outcome. And that's the piece of our investing is a secondary investor you often often don't get that granular involved with and we do it with a handful of companies Unfortunately typically when they have issues that you're trying to save but yeah, it was a very hard journey Well, there's kind of the numbers you can quantify and then there's the dollars that you lost from a fundraising perspective for your next Vintage is from LPs because he lose that come yeah because you when you lose come Investors do you lose them as an extra on up here depends on how you structure your co -investments in that case from that fund My guess is those decisions we made cost our partnership probably a half a billion dollars a capital between capital actually lost and Investors that you can't bring back it was a monumental miss on our part.

1:04:30I have lost money before in co -investment The only lesson that I've learned actually on that is use it as a chance to build trust and in crisis Can you communicate more than you ever have done before? Yeah, and try to over communicate a lot of LPs because of that. I've come back and now they're... Does it make you question your current best strategy? Because the thing that I don't like with current best is often LPs. They're almost not aware that it's a single shot. And what I mean by that is, you have a portfolio and a direct, and a bench fund, fine, you have a get it, fine, we've got a toast as well.

1:05:02Yeah. But it's like they're almost shocked that, oh shit, I didn't realize that's done. So kind of going through our co -investment process and the early ventages, let's say, vintage one through four. In some cases, we were four times co -investment to fund investment because we - Four times, yeah. But here's why because the kind of companies that we were interested in investing in, we weren't large enough to make a difference. So if you want to run our business model, you need capital, a lot of capital. Just to get in the door. Just to be able to solve the problems that they have, to your point of being relevant to the rofer, if all you can do is one's ease and two's ease and you can't write a hundred million dollar check when they need you to do it on the secondary They go find somebody else and when they turn that faucet on a shares when they buy into your strategy when Daniel Lux says hey you guys are interesting to us.

1:05:48Oh, by the way, here's a hundred fifty million dollars stock If I say no and it's at a good price and he picks up the phone and call somebody else It's gone that you're not getting that opportunity back with our strategy you have to have scale So is the co -investment in the early days was the significant part of our strategy over time It's more normalized today. It's about on a billion five. It'll be seven hundred million It's still a lot the mistake we made in 2021 vintage or 2020 vintage is we didn't just do cone investments around our core positions We had LPs coming to us saying hey, I built my fortune in let's say wellness.

1:06:20I like health tech companies You've got one down here in the land. I want to buy stock directly and we felt at the time hindsight being 2020 20, it was wrong. We felt at the time that we were enabling our business model to help them achieve what they wanted by being an LP of ours. Okay, but let me just push back when you're, we're partners now. Okay. I say they have directly requested that. I said, I share with them my concerns and how we believe the company is doing. And if I do that transparently and offer the mattress, am I not providing them a service that they're asking for? Yeah, until it doesn't work.

1:06:52And then they blame you. So you should blow them from doing I wouldn't so the way we run it today is the way I think people should run there only in conviction when your funds are investing alongside of it That's when you do the co -investment you don't do it the way we did it in 2020 you do it the way we did it today Our 2022 vintage fund there was a billion two in size the co -investments we ran or our top 10 positions a couple LLMs the high flyers companies like fanatics whiz Databricks, Turo, the Airbnb of cars, Monso, companies like that, where you've already decided those are your core positions and then they make a bespoke portfolio of additional exposure to them, an equal weighted size.

1:07:33Why are you in Monzo? Value play to Revolut and T .S. is fantastic. I think Revolut is the general issue. We're in Revolut and our 2018 vintage fund. I agree with you, amazing business. Did you hold it? Yeah, some of the stuff we can't really talk about holding it or not in the live positions, but... I just think it now and I'm like, fuck me, this is the 500 billion. We have in our 2018 vintage fund, it's made an awesome return for that vintage today for me. How did you get to, Ravallude in 2018, dude? You're like a mid -American, oh, come on. I'm sitting in fucking London and I didn't see it in 2018.

1:08:08I was fucking hustle, Harry. Hustle. I was 12 then, key. Oh, you know. I'm pretty sure you had easier than that. This was well before. Yeah, well before. I think four mega trends for us, Fintech is one. And we had good success coming off of SoFi, the founders of SoFi, and now the current management really believed in our strategy. And SoFi was actually also in our 2018 vintage fund. Yeah, that fun, man. It's just crazy what was in it. And off the back of that win, and then we had early N26 before the growth restrictions. Did you sell? No, no, we didn't we didn't sell they're working their way through some things and looking fairly okay right now And they're doing a really good job of managing through the the stress they had in the business and now more of a focused in Germany versus kind of a continental play and then we had a revolute what a great little pool of companies What a great pool and say you were like When like a hockey stick man, so yeah, and our strategy you need like and so you like I see revenue You're like always I'm gonna go into mom's well monso is a later vintage So yeah, it revolutes in our 2018 vintage where sometimes and we have them in every vintage, you know, in our current vintage we have chime, awesome business believed in our business model.

1:09:25But it went so fast that you can't build with you over time dollar cost averaging in through lots of transactions. You can't build a scalable position if the company goes from zero to a hundred and no time. You know, Wiz was very short for us. 20, their current vintage, we did it in three years, but it was only because it started with the back of the downturn. We caught it at the right moment. Normalized scenario, we would have never been able to build this position in ways because it was a hockey stick from day one, but the capital availability, even to the best assets in the world, wasn't great for 18 months.

1:09:58What price do you get in this one, sir? Oh, sub four billion. Yeah. We're not solving for what you're solving for. So you have to do this. Yes, it's great. I really have. Yeah, T .S. has a great opportunity. I understand. Right, guys. So I think what you have to build a portfolio across the four mega trends for us, the way we look at it, is you have to diversify that risk. So you have SaaS, you have Fintech, you have consumer internet and mobility. And so what we do across those is we try to build conviction positions, pretty equally weighted across those mega trends amongst 10 companies. And so for every anthropic you have, you have to balance that with a fantastic business in fanatics, which is more of a traditional, like last quarter, talk about growth.

1:10:39I mean, the business is fantastic. And it's at scale, massive scale, billions of dollars of revenue, and hundreds of millions of dollars of EBITDA, like a massive company. Michael Rubin owned pretty much significantly own sports apparel merchandising business. You balance that risk. Because what we've learned over time is you can't just play the momentum because you can get burned and that's chasing multiple. Totally get that you can't just play the momentum. How the fuck do you play AI then? Because it is. A lot of leaders. That's easy. Go to the winners. Cap, what's what's holding back the next generation of the LLMs to get to anthropic and open AI scale?

1:11:17In three years, who's going to rival them? No one. You just answered your own question, Harry. No, I completely agree with you. No, I literally, not if for what I'm about to say, may my LPs forgive me. If I could do anything, I would be careful. They're your blood that pumps through your heart. I know I adore them and I think they probably agree with my next statement. We'll see. I will put my whole fund into open AI. You would. Yeah, it's if, you know, you express your McLeod should start a fun together. He's amazing. He's my cool P .M. He believes the same thing. It's 350. Do I see this being a one and a half trillion dollar company in five years time?

1:11:51Easily I do. That is a five X with fair confidence, but very large confidence in a five -year period. Yeah, it's an amazing business. Yeah, I would do that 100%. It's really to escape velocity. I speak to Kevin, Scott at Microsoft, and I'm like, yeah, but dude, there's no defensibility on the search. And he's like, and you can't just switch from Google to Bing, of course you can, but it's the brand. Poor Bing always gets picked on. Bing, everybody picks on Bing. Everyone here, even he does. See, too, I need to pick on Bing. It was him, not me. But like, when me, I was like, wow, yeah, That's absolutely true.

1:12:24And so I agree. Okay, but I have friends who are an anthropic and got in at four and It needs comment and it's now 60. Yeah, 61 a 61 and they've got like a four X yeah on their money And so there's a question of like okay, value accrual. Have them call me I'll buy all their shares of anthropic at 61 billion You would buy it all day long today and twice on Sunday. Are you serious? 100 % even though the dilution is so So intense. See, now you're talking like an early stage investor, Harry, I don't give a shit about the dilution. Why? I give a, I care about the price I pay in dollars and the price I'm going to sell it at in dollars.

1:13:06I am focused on DPI, not M O I C. I don't care about the dilution. So are you not just going around now, hovering up and throttling? Oh, 100%. Is that much to hover up? a lot and I've got appetite for more. Same with open AI, same with Databricks. Wiz, holy shit. What do they built was amazing. We hosted them in our LP day. Half the things they say I don't even understand what they're talking about. So here's a shit out of me, the world, after talking to three of them. It was out there, but man, did they build? How they did that? By the way, they also sold a business to Microsoft together and made a bunch of money and then said, hey, yeah, we're well healed.

1:13:46They're humble people. They've made a lot of money and some of them live in like a one -better apartment in Tel Aviv I went to see him in Tel Aviv I went to see a bunch of companies will leave the other ones out a couple And wouldn't even see me and this is after I managed five plus million dollars It was guys welcome me in gave me a sweatshirt how you doing like oh by the way I want to land in your company you're raising like half a billion dollars I want to give you like three million bucks three million They're like you know, that's a little small area, but we like you We you settle on nine sure I'll give you nine million bucks That's how we started.

1:14:17And then we went on and built a $200 million position. It takes that buy -in, and so you go back to Anthropic and the others. We were fortunate enough, during you mentioned FTX earlier, to be awarded during the bankruptcy a bunch of stock. We bid on it. We went through the whole process, bid on the stock, bought a big chunk. The company is, and my opinion, is unstoppable. That in an open AI, they're just the beginning. So how do you play the space to go to the winners? Because I have a shorter thesis. How many winners are there? I think the LLM space is challenging for new entrants. It's because it's time and capital.

1:14:50But I think it's like opening an anthropocate. Yeah, I don't see a ton of room for more, not because I don't think. So you're going to play the application layer too, and you're going to try and do cursor and a bridge in medical. No, I mean, I think for us, our view is take a few concentrated bets in the foundation models and the winners. And then let's play a bit of the picks and shovels. That's why we have Lambda. but we also had CoreWeef. And then on the business models themselves, let's play a scale AI and software to help them scale on the hyper -scaler side and focus the balance of our capital on our other mega trends.

1:15:27Where AI has been embedded into all businesses. So you have exposure to it throughout cyber -insass, you have exposure to it at Fintech, you have exposure to it in consumer, companies today that are created without AI embedded in their DNA, like why? Why would you do it? If you're not going to, if you don't put it in there, the challenge you have in our industry is you have Vintage of managers who invested basically for the last 20 years Many of them without liquidity and most of their businesses don't have AI embedded in the DNA of the company And so they're chasing now you have incumbents that are large There's two types of companies that were that are big and private that are aren't in AI They're kind of we talk internally.

1:16:09We call them vampires and zombies because they're massive many are profitable, they have to now implement AI in their business models and you have some that are going to get out of it and be okay, those are the vampires and the zombies are dead. There's hundreds of them. I think there's far more zombies than there are vampires. I think there's a much more difficult transition to implement AI. I think a lot of product change is actually from bottoms up and you can't just slap AI in it. It's hard. Here you go. It's hard and its companies are going through. I really want to do a five crisis and name it PFU.

1:16:41I'm just private actually fuck you. And I just want to go down Anna Plan Cooper, you name it and just take out one by one by one where you've got to have a couple of things. Founders not there. Engineering team cut, customer service cut, price increases. No, and then by the way, layer some secondary on lower the cost basis and you can make a five X in three years. Yeah, yeah, no, it's a great idea. I think that there's long and the tooth companies from 2015, ventages. So is my generation and the generation of LPs funding as morals? I mean, that in the nicest way, and I'm being deliberately glib, but in the liquidity profiles that we're doing.

1:17:17And is 15 years? Yeah, I think it's hard, Harry. I mean, liquidity is hard. The one thing, and you asked me this question on our walk, is like, what do LPs think they know that they actually don't? Yeah. And I would say how hard liquidity actually is for us, all of us. It's really hard. And that's why the DPI numbers are so low. So it's not because people don't want to make money for people. It's because it's hard. It's just as hard as getting into the best deals. It may be harder to get out. Is that even the case in the high demand assets like we have today with the other LAMs? You want to sell your anthropocentric assets?

1:17:51Yeah. Today, I think there's a handful of liquid private companies basically. They're quasi -liquid. Because this is the hard thing for you. But at scale, small positions, yes. Because I look at my mind. But try to go move a billion dollars of anthropic. Agreed completely. But I look at my first one which was tiny in Italy, but I all of my winters. It was large compared to mine. But all of my winters, I can sell tomorrow. I don't want to fucking sell any of them. Yeah, but all of my shit, I'm desperate to sell. Well, that's the classic. That's the classic. Sell your dogs and keep your winners.

1:18:24And I think it's actually the somewhat of the inverse is you have to be able to willing to sell your winners to have a sustainable business model. and to generate the return that will actually drive your Harry's fund forward. What has been the single best investment fee on a multiple basis? Early Wiz and probably early Spotify, both of those were in Bolt, the early ride -hailing. It's yet to be determined, Marcus Fillig Business. We were the first institutional money from the North America in that business. Those first investments we made, and all three of those are probably 10x. Why did you do that?

1:18:56Which Bolt? Yeah, I love Marcus. He's amazing. On the show he was fantastic. Yeah, he's amazing. But dude, respectfully, when you went in, this was pre -siccoya. Yeah. Pre -institutional accreditation. Yeah, I think it was like 20 bucks a share or something. It's equated it at 260. Yeah. So, yeah, and this was like not the brown. No, no, but we had come off in fairness to us. We just came off a great outcome in lift. We didn't know yet what Uber was going to be. I was going through all the challenges around the transition of founder. Johann Berquist that was at Spotify called me and said, what do you think it lift the new bar?

1:19:32And I gave him my opinion on both. And he's like, well, there's a small business out of Estonia that I'm going to go be the CFO at. And Johann has been our single best investment we've ever made. Spotify, early investment that he trusted our business model in, let's say eight to 10X. Bolt yet to be determined, but let's just assume it's somewhere between 50 % and face value of what's Coa paid. It's 6, 7, X. And now it's a big business. And Marcus is phenomenal. Young kid building that business thesis was, well, go where Uber's not and do it profitably because I don't have any money. Being blunt.

1:20:08Yeah. As I said, you said your humble beginning is earlier. You've done very well. That's all relative. What's well? But yeah, go ahead. Does money make you happy? Money doesn't make me happy. Money makes my life easier. Money makes your life easier. Complex in some ways. What did you think about money that now you have it, you now see differently. When I was growing up, I thought if I could just make $5 ,000 a month, I would be set. I could just make $5 ,000 a month on my own farm and farm it. That's all I wanted to do. And then I spent 20 years trying to get away from the farm. And now all I want to do is go back.

1:20:44But money doesn't make you happy. I think it makes your life complex. How you handle that money is important. What do you learn to put handling money when it comes to you? Yeah, me personally. Aside from me, don't increase my spending with my increased wealth. Yeah, I think that's a good goal, Harry, and you should try to maintain that. It's very hard to maintain that. For me personally, my journey has been about not having that fear of going back to the powdered eggs and powdered milk and the government cheese, and that fear that it could happen again, and setting my family up so that my children won't ever have to go through that, and generations One have to go through that.

1:21:23That's been my desire and now that we're partly there creating that I would say I'm in the Probably middle innings of doing that for where I want my life to be Reminding yourself of where you came from constantly is important because it's easy to be around people in our profession and just in general in life as your Financial status increases the people around you change a bit and I think that pull to be more like everyone is there and maintaining the thought in your mind that this always hasn't been what your life is and being thankful that it's here without losing the edge. The most difficult thing to do as you start to make real money regardless of how you define that is keeping that edge that got you there.

1:22:11And I think you see that across sports, that you see it across business. I think you see about high performing CEOs. When you think about keeping that edge. Yeah. Is it the running away from the government, cheese and policy, or is it the running towards the grandchild memories of G -Squad? I think keeping the edge for me isn't about either of those things. Keeping the edge for me is the chase of the next win and that no matter what dollar amount is, that the win is what gives me satisfaction and the loss is what hurts. Like I spend a lot of time talking to you about the losses because that's what I really can remember.

1:22:48Mostly every moment of those and as an athlete I remember all the failures. Should you ever build immunity to losses? Yeah, immunity to losses would be nice to say that you should do that because maybe you'll be happier plus the money, maybe you're like, high on life. Yeah, I think some people can. For me, it's I think ingrained in my DNA that I don't want to leave. I don't want to know who that Larry is. I enjoy the fight. I enjoy the journey to win and everything in life. I want to win. Final one, we do a great file. What does is no one see about farm building. Having built a farm, you think is so cool.

1:23:26Building something that then you don't realize that people outside of your small sphere recognizes is something positive. And that is something that you're randomly faced with. Like this conversation for me is, is I'm a huge fan. It's like sports radio, a long time listener, first time caller. You're a young guy, but you're super successful and you have some of the most amazing people in our industry on the planet sit here and talk to you and to think that I'm sitting here with you telling in my story is for me very humbling in the fact that you're even interested. And I think that piece of building a firm and think focused on the logo and not me individually has led to this moment.

1:24:07And that tells me that we all for all of our flaws which we have many there's something in the water G squared that works. And we're going to keep grinding and doing it. I'm going to do a quick fight with you. Otherwise, I can keep you all day. Yeah. Okay. So tell me, whose life do you secretly admire? I'm why? I look at because of my background in sports, who I admire. I think the longevity of like a Cal Rip con Jr. in baseball who basically for 16 straight season didn't miss a major league baseball game. Major league baseball plays 160 games a year. For 16 years, the time the guy was 22, the time he was 38, didn't miss a start.

1:24:44You know, Now people talk about records and sports and all of the high flying athletes that people recognize and their accomplishments. Here's a guy who was a grinder, played third base, hard position to play in baseball. I know you're a cricket guy, but study it up. 16 years, not miss a game. Of course, he's in the baseball hall fine and celebrated that way, but a good player, not the best, but the grind that that must have taken for him to do that. Just to get to the major leagues is not being the most talented guy and then to play and not miss a game for 16 straight years for one team in 38 when he retires.

1:25:16That to me, we talk about our 20 mile march every day. G squared like it's a 20 mile march, rain or shine, remarks in 20 miles. And we're going to make progress. That is a different kind of a testable fortitude and a set of massive steel balls that you just don't get in generations today. What that guy accomplished is unsurmountable. They will not be another baseball player in my opinion in the history of the future baseball that will accomplish what he did. It's very kind of you say about like listening to the show of May family. Three shows a week for 11 years. There you go. Like no one giving a shit for four or five of those years.

1:25:50Yes. It's the grind and the willingness to have faith and that you can do it and living and breathing the challenge and making it become your identity. And I'm sure I don't know Cal Ripken Jr. I can only imagine what he went through. But I imagine it often waking up at 38 years old, Playing another random baseball game on a shitty team in Baltimore, like to go out and grind, it'd make that happen for what reason. He'd made tons of money. Why do it? Why do the early shows where nobody was listening? Because I loved that. Because you loved it. Because it was your passion. So that's. And that's where people should find their work life balance.

1:26:27Is when your work is your life, your life is balanced. I couldn't do this today if I didn't love it. No, of course not. Why? If you don't have to go far you're in your house You go swimming next door walk in the park. I don't tell you we do a session in the sauna afterwards Oh, yeah, that's yeah, that's a little weird, but I'll go Where were you opinion? It's fine. I know. What would you most like to change about G -squad that you can't? I think our people would like me to chill out just a little bit and if I could be a little chiller and less grinding, I think people at our firm would probably enjoy being there more than they do.

1:27:07The money's awesome for everyone. People don't leave. We only have forced attrition. That aside, I spend a lot of time thinking about how to change my delivery at this point where we are survivable. We will have the next vintage. We're going to have many more ventages. There's not fighting just to fight. It's needs to be altered without losing the edge. And I wish I could change it more quickly than I have. And I think it's led to unfortunately some really good people moving on that otherwise I would still like to be on the journey with me. What was my memorable LP, Mision? Here in London, guy committed on the spot and you know set all sign the forms for 20 million bucks.

1:27:44Wow. First meeting said I'll do it. Never happened to me before. And it was here in London, long time LP still with us today. Saw the, I probably didn't even care about the strategy just I think like me and said I'll do it. That was the most memorable for me. Yeah. What why is he today that you don't think many people are thinking about? I think fundamentally our industry is the people searching for solutions to the fun life problem. They're searching for a solution to it because it's fundamentally broken and they don't want to say out loud that it's broken. So evergreen structures, interval funds, quasi -liquid strategies and privates, continuation funds.

1:28:23The continuation funds though I find a bit more interesting today than they were in the early inscriptions because now you only want, they will only buy your good assets. So now they're, they've really gotten smart. That's really interesting space right now. I'm a CIO of a large endowment fund. What advice would you give me today about allocating in this environment? Wearing diamonds miss the button by the way I'd love to have many of them we don't. Is I think they chased the wrong statistics? What do they chase that they shouldn't and what should that they chose. My belief is that TVPI and M .O .I .C.

1:28:55are not the stats that people should be focused on. And they are. I think they're fake numbers. They should just chase DPR. It's the only thing you can use to buy food. When you think about yourself as a leader, what could you do to be better today? I think I need to continue to grow and be more open -minded in which I have, and I have full trust now, in a co -PM of mine, who I think is one of the smartest people I've ever met and fantastic investor and he has my ear. I think I could do a better job of having more people have my ear. Like I could listen to more people than I do. And that's a challenge for me in the protectionist mode, just my nature to be productively paranoid.

1:29:35And I should listen to more people in their advice that they give me. And that's just something I've worked on for the last probably five years more extensively is gathering more around me digesting it and then acting versus acting. Fun in one, when has being paranoid helped you? When is that helped you? Well, I told you about the Theranois that helped me. That was the productive paranoia. And also the productive paranoia of closing and investing. The money's there, close it, invest it. Money's there, close it, invest it because you don't know when the next one's coming. And that's a bit of just my DNA as a human being and how I was raised is that productive paranoia that it's great today, but the wheels are going to fall off.

1:30:15and you have to make sure every day that you tighten the wheels and you have to be focused on the right things. That driving every day, that having that paranoia, no matter how good things are and always worrying that it's going to get worse, across all things in life is to a degree it's healthy. I so appreciate this. I so appreciate the willingness to talk so openly. I loved it on our first walk. I really did. It was very special, which is why I was so keen to make this happen. So thank you so much for doing this with me, man. Well, thanks Harry. Congratulations on what you've built. I'm a huge fan and I think you're only only in the beginning of what you're building and I'm gonna be cheering for a long away time for the swallow.

1:30:53Yeah, let's do it. Sonna here we come. Nine Badenhosen. As you heard Larry say there we went for a walk in the park and I just thought it was such an incredible journey. I'm so glad we can make that show happen. I've got a new friend in Larry and I hope you enjoyed it. You can find on YouTube by searching for 20 BC. that's 2 -0 VC on YouTube. But before we leave you today, I love seeing the team come together to make this show happen. What I don't love is trying to keep track of all the information, the data and the projects that we're working on across dozens of platform products and tools. That's why we use Coda, the all -in -one collaborative workspace that's helped 50 ,000 teams all over the world get on the same page, offering the flexibility of docs with the structure of Brad Sheets, Coda facilitates deeper teamwork and quicker creativity, and their turnkey AI solution, the intelligence of Coda Brain, is a game changer.

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From the publisher

Larry Aschebrook is the Founder and Managing Partner of G Squared in what is one of the wildest stories of venture capital. Larry started G Squared with nothing, dialling for dollars having personally invested in Twitter and Uber. In his first fund, Larry made sizable bets into SpaceX, Palantir, Alibaba and Twitter. Larry has also had mega losses along the way (discussed in the show) in Getir, 23andme and more. Today, Larry manages over $5BN and has invested in all the best from Wiz to Spotify to Revolut and Anthropic. 

Agenda:

00:00 – From Broke to Billion-Dollar Bets

03:40 – The $800M Coursera Windfall

06:10 – Lyft Made Millions, Uber Lost $50M

09:05 – “We Fcked Up”: The Billion-Dollar Vintage

11:50 – How a $150M Spotify Bet Made a Billion

15:10 – The Gut Call That Dodged Theranos

18:00 – Vampires vs Zombies: The Coming Startup Purge

20:30 – When Success Almost Killed the Firm

24:20 – DPI Is King, MOIC Is Bullsht

27:40 – Why I’d Buy Anthropic at $61BN Today

30:05 – Losing $70M on 23andMe

32:10 – The Janitor of Venture Capital

34:00 – The Getir Deal That Nearly Broke Me

36:25 – Does Money Actually Make You Happy?

39:00 – What Cal Ripken Jr. Taught Me About Venture

 

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20VC: How We Made $800M on CourseraThe Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 1 h 35 min
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