The Exchanges

Q 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. Dialing for dollars is kind of how I was thinking about this. How did you start your way into venture, and what was that entry point?

A Yeah, for me, it was, it wasn't really, hey, I want to be a venture capitalist and manage, you know, billions of dollars. It, for me, it was, you know, I come from nothing. Um, I 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. It would be a PE funds or venture funds or running their own operating businesses. It didn't matter what it was from You know, 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. I work hard. I'm smart enough. Um, 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 follow Twitter. I like Twitter. Uh, you know, what about, um, early Uber? What about early Spotify? And I just started buying shares from my classmates with my own money.

AI assessment note: “I just started buying shares from my classmates with my own money.”

Q Totally get that. I, I want to go back to the four names you mentioned, you mentioned. How do you get Spotify? What's the story there? I, I love Daniel. He's one of my oldest friends. Yeah, I love that. Shack as well. They are special. How do you get a Spotify in 2014?

A Yeah, so, so one of the first employees I hired, um, young guy out of Berkeley. He's now my co-PM, Spencer McLeod. You gotta meet this guy. He is, he's a, he's, he's a living caricature of what Silicon Valley is. He was working as an analyst with me. Um, uh, this is like, 2014. Um, I think he's like 22 years old at the time. And, um, I was telling him this story about how my, 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 in Spotify. And it literally, that's kind of how it started. And we started searching around and we found a celebrity that was going through a, uh, unfortunate change of life scenario in a divorce. I need like four million dollars of stock. And we had a, you know, three hundred million dollar fund at this point. I'm like, yeah, let's buy it. Well, Spotify had this interesting process of, of, of how they approve shareholders. It was kind of onerous and difficult, and my mentality was, hey, well, they're not responding, so let's go see them. So literally Spencer and I flew without an appointment to Stockholm. Um, my wife came, uh, we spent a week there in the terrible northern, like November. Um, we had a new baby and we were staying in an Airbnb that we rented, um, which became a great investment for us…

AI assessment note: “we found a celebrity that was going through a, uh, unfortunate change of life”

Q I'm sorry, dude, how do you get in touch with Jack Ma's family office to buy shares from them?

A I mean, that's the story of my life. It's like, you know, it's, it's, it's a bit, a bit of luck. You, you meet an alum that I knew, knew somebody that knew somebody and, you know, Kind of introduced me to a gentleman's name was Barry Purcell, who was running, um, some of Jack Ma's money in Virginia of all places, I believe. And he said, Hey, we have some shares to sell. I'm like, ok. Hired a group in India to do some DD, because I had like two people. And wrote me an investment committee. Oh yeah, my early investment committee memos and the early vintages were outsourced to, you know, a group of really smart, um, analysts in India, that you could pay a fraction of what you could pay talent in the US. And I didn't have any money to invest in talent.

AI assessment note: “an alum that I knew, knew somebody that knew somebody and, you know, Kind of introduced me”

Q Totally get that. I, I want to go back to the four names you mentioned, you mentioned. How do you get Spotify? What's the story there? I, I love Daniel. He's one of my oldest friends. Yeah, I love that. Shack as well. They are special. How do you get a Spotify in 2014?

A Yeah, so, so one of the first employees I hired, um, young guy out of Berkeley. He's now my co-PM, Spencer McLeod. You gotta meet this guy. He is, he's a, he's, he's a living caricature of what Silicon Valley is. He was working as an analyst with me. Um, uh, this is like, 2014. Um, I think he's like 22 years old at the time. And, um, I was telling him this story about how my, 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 in Spotify. And it literally, that's kind of how it started. And we started searching around and we found a celebrity that was going through a, uh, unfortunate change of life scenario in a divorce. I need like four million dollars of stock. And we had a, you know, three hundred million dollar fund at this point. I'm like, yeah, let's buy it. Well, Spotify had this interesting process of, of, of how they approve shareholders. It was kind of onerous and difficult, and my mentality was, hey, well, they're not responding, so let's go see them. So literally Spencer and I flew without an appointment to Stockholm. Um, my wife came, uh, we spent a week there in the terrible northern, like November. Um, we had a new baby and we were staying in an Airbnb that we rented, um, which became a great investment for us…

AI assessment note: “Spencer and I flew without an appointment to Stockholm”

Q Okay. So tell me, Whose life do you secretly admire, and why?

A I, I look at, because of my background in sports, who I admire, I think, the longevity of like a Cal Ripken junior in baseball, who basically for 16 straight seasons didn't miss a Major League Baseball game. Major League Baseball plays a 160 games a year. For 16 years, from the time the guy was 22 to the time he was 38, didn't miss a, didn't miss a start. The grind that that, and a lot of people, you know, people talk about records in sports and, you know, all of the high-flying athletes that people recognize in their accomplishments. Here's a guy who was a grinder, played third base, hard position to play in baseball. You know, I know you're a cricket guy, but, but study it up. 16 years, not miss a game. Of course, he's in the baseball Hall of Fame and celebrated in that way, but a good player, not, not, 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. That to me, we talk about our 20 mile march every day at G squared. Like it's a 20 mile march, rain or shine, we're marching 20 miles. And we're gonna make progress. That is a different kind of intestinal fortitude in a set of massive steel balls that you just don't get in generations today. What that guy accomplished is, is insurmountable. The…

AI assessment note: “who I admire, I think, the longevity of like a Cal Ripken junior”

Q I agree with that. So why did you sell at 25 then? You just thought it was-

A Okay. Funny story. Um, And personally, you know, you have experiences with companies and very frustrating experience with Instacart during COVID where, you know, it went from Whole Foods only pickers and grocery shoppers, which was an amazing service, right? To 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, you know, um, and, uh, it's just like, I can't get the order. It just can't, 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.

AI assessment note: “very frustrating experience with Instacart during COVID”

Q What would you most like to change about G-Squared that you can't?

A I think me personally, 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. The money's awesome for everyone. People don't leave. We only have forced attrition. That aside, I spent 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 vintages. There's not fighting just to fight. It 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, it's led to, um, unfortunately some really good people moving on, um, that otherwise I would still like to be on the journey with me.

AI assessment note: “if I could be a little chiller and less grinding I think people”

Q What were the holes, and how did you?

A Too much qualitative. Too much my gut, my feel. Too much, um, who else is in the room. Too much, yeah, just the soft stuff that venture capitalists and growth managers like to pride themselves about. And our strategy has to be about the numbers. It, it, it has to be just cut and dry, cut throat. Does it work financially or not? Because at our stage, unlike yours, which it doesn't, you know, from your seat, in a lot of ways I envy your seat, because if you pay 50 pre or a hundred pre, if it's a good business, you're still gonna make a five X. A 10 pre, 50 pre, does it really matter for you? Maybe. For me? Is it three billion or 2.5 billion? You walk that forward, I can't make my two and a half X net in a five year period if I miss that. Now I get an okay return, but I'm not rehired.

AI assessment note: “Too much qualitative. Too much my gut, my feel. [...] our strategy has to be about the numbers.”

Q And so just so I get it right, what was the thesis?

A For 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 20 10. From 20 10 to 20 18 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 who have no liquidity, and there, 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, you know, hey, Dorsey, my name's Larry Ashbrook. I'm a, you know, a retread athlete that wants to become a venture capitalist. Can I invest in Twitter? Sure. And by the way, my fund size is, ah, I don't have a fund. I just have, like, 200 grand in my name. I'd like to buy, you know, 10,000 dollars worth of Twitter stock. That, that conversation obviously wouldn't go anywhere, so, um.

AI assessment note: “there's an opportunity to buy shares from these people who have no liquidity”

Q And so just so I get it right, what was the thesis?

A For 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 20 10. From 20 10 to 20 18 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 who have no liquidity, and there, 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, you know, hey, Dorsey, my name's Larry Ashbrook. I'm a, you know, a retread athlete that wants to become a venture capitalist. Can I invest in Twitter? Sure. And by the way, my fund size is, ah, I don't have a fund. I just have, like, 200 grand in my name. I'd like to buy, you know, 10,000 dollars worth of Twitter stock. That, that conversation obviously wouldn't go anywhere, so, um.

AI assessment note: “there's an opportunity to buy shares from these people who have no liquidity”

Q So what was the realization when you saw Toast?

A That Toast was, 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 we had to, we, we really 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, you know, more than just the co-PMs and Spencer and myself, and that we could, we could do a traditional model. Cause we don't do that. We deploy the capital between the two of us. We have a research team that support 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. LPs are coming aboard with big checks. They want to chase Moik. 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 SAS. Public markets are trading at 25. Pat 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 twenty-twenty-five. The multiple is four. So when that happened, when, when a really awesome business, which we made a ton of money o…

AI assessment note: “That Toast was, I have a problem in this vintage. We've overpaid for all of it.”

Q That sounds great, but these companies are not public at the time. No. So how does one do that then? How did you approach it?

A Well, I guess it's not knowing what you don't know is an ignorance is 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, How about, well, you have shares. Can I buy some of your shares? Well, I never really thought about selling 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 the Cary 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, I got it back from a broker not that long ago, and it's like literally the form I created in 2010. One page. And it's binding though. That's scary. It's binding. Which has bitten me in the ass a few times.

AI assessment note: “I just asked people, How about, well, you have shares. Can I buy some”

Q What were the holes, and how did you?

A Too much qualitative. Too much my gut, my feel. Too much, um, who else is in the room. Too much, yeah, just the soft stuff that venture capitalists and growth managers like to pride themselves about. And our strategy has to be about the numbers. It, it, it has to be just cut and dry, cut throat. Does it work financially or not? Because at our stage, unlike yours, which it doesn't, you know, from your seat, in a lot of ways I envy your seat, because if you pay 50 pre or a hundred pre, if it's a good business, you're still gonna make a five X. A 10 pre, 50 pre, does it really matter for you? Maybe. For me? Is it three billion or 2.5 billion? You walk that forward, I can't make my two and a half X net in a five year period if I miss that. Now I get an okay return, but I'm not rehired.

AI assessment note: “Too much qualitative. Too much my gut, my feel.”

Q And in what way? Because it's a very common.

A Yeah, it's because people want to, people want to pat themselves on the back for the wins and deflate the losses, or deflect the losses, excuse me. I think if you want to build a firm, That stands the test of time. The logo makes the investment. It withstands any transition period in any leadership role in the firm because the logo made it, not the individual. And that's what I'm, that's what we're trying to build at G squared is when I look out 20 years from now and say, where do I want it to be? I want, you know, hopefully 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 like the Jim Simmons, 40% annualized IRR for 20 years.

AI assessment note: “people want to pat themselves on the back for the wins and deflate the losses”

Q What would you most like to change about G-Squared that you can't?

A I think me personally, 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. The money's awesome for everyone. People don't leave. We only have forced attrition. That aside, I spent 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 vintages. There's not fighting just to fight. It 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, it's led to, um, unfortunately some really good people moving on, um, that otherwise I would still like to be on the journey with me.

AI assessment note: “if I could be a little chiller and less grinding I think people at our firm”

Q That sounds great, but these companies are not public at the time. No. So how does one do that then? How did you approach it?

A Well, I guess it's not knowing what you don't know is an ignorance is 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, How about, well, you have shares. Can I buy some of your shares? Well, I never really thought about selling 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 the Cary 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, I got it back from a broker not that long ago, and it's like literally the form I created in 2010. One page. And it's binding though. That's scary. It's binding. Which has bitten me in the ass a few times.

AI assessment note: “I just asked people, How about, well, you have shares. Can I buy some”

Q The candidness is important. When you look back now, what do you think your sins were?

A And I've talked a lot about this openly to our LPs, because, um, I take pride in going around the world, and we have 60 countries and six continents of LPs. It was smart. In my opinion, when I started the firm, it was fun. Uh, it's, it's difficult now. The main mistake we made was believing our own bullshit. Was believing that we were, cause coming up to that point, we had some of the best returns in our industry. Like we were raising money. It didn't, we just, to put the flag out there, it was hard. We go around, raise money. Co-investment, raise money. Life changed dramatically for my partners, myself, our team. Just to ship back, you know, uh, 20 18 vintage fund. By 2020, we had the DPI to almost one. Oh yeah, Airbnb goes public, make a three X. Coursera goes public, make a three X. Sell our SpaceX stock privately, you know, make a, make a big return. Impossible Foods make this huge return.

AI assessment note: “The main mistake we made was believing our own bullshit.”

Q But my question to you is, have your guardrails not now become a constraint, a negative constraint?

A Yeah, look, I think if, if, 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, a 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, and if you have confidence in the mousetrap you've built, Forex in 10 years, cash on cash return, is pretty hard to beat.

AI assessment note: “the answer to that is, we're doing what we're hired to do.”

Q So what was the realization when you saw Toast?

A That Toast was, 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 we had to, we, we really 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, you know, more than just the co-PMs and Spencer and myself, and that we could, we could do a traditional model. Cause we don't do that. We deploy the capital between the two of us. We have a research team that support 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. LPs are coming aboard with big checks. They want to chase Moik. 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 SAS. Public markets are trading at 25. Pat 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 twenty-twenty-five. The multiple is four. So when that happened, when, when a really awesome business, which we made a ton of money o…

AI assessment note: “I have a problem in this vintage. We've overpaid for all of it.”

Q For people that don't know, what does that mean?

A It means you embed IRR hurdles and multiples in the paper. So regardless if you say the business is worth eight billion on paper, the company has to generate you a 25% IRR or a two and a half X, whichever 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 Spencer and I to get together and say, What, what were we thinking? We have to try to save this thing. Our LPs trusted us with a billion at that .1000000005.

AI assessment note: “It means you embed IRR hurdles and multiples in the paper.”

Q So are you going to play the application layer two, and are you going to try and do cursor and abridge in medical?

A No, I mean, I think for us, um, our view is take a few concentrated bets in, 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. We also had CoreWeave. Um, and then on the business models themselves, let's play a, a scale AI and software to help them scale on the hyperscaler side and, and focus the balance of our capital on our other mega trends where the AI has been embedded into all businesses. So you have exposure to it Throughout cyber and SaaS, you have exposure to it in FinTech, you have exposure to it in consumer. Companies today that are, are created without AI embedded in their DNA, like why? Why would you do it? If you're not gonna, if you don't put it in there, like why? The challenge you have in our industry is you have vintages 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. We call them, there's two types of companies that were, that are big and private that aren't in AI. They're kind of, we talk internally, we call them vampires and zombies. Because they're massive. Many of them are profitable. They have to now implement AI in their business models. And you have some that are gonna get out of it and be okay. And t…

AI assessment note: “No, I mean, I think for us, um, our view is take a few concentrated bets”

Q What was it about it that was made?

A At that time, the penetration of the usership in, in, in Sweden was like, 25% of the population used it. I mean, that's amazing. 25% of the population used the product. And you're like, it's already cool because you're using it. And of course, Apple music, and I think that beats and, you know, uh, title and all these, you know, SoundCloud, all these competitors, but what they divulged to us in that one-on-one personal meeting after saying no to us for six straight days, um, was the fact that the record labels were also investors. That to me was like, ok, 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 a hundred and fifty million dollars to go find.

AI assessment note: “was the fact that the record labels were also investors”

Q So are you going to play the application layer two, and are you going to try and do cursor and abridge in medical?

A No, I mean, I think for us, um, our view is take a few concentrated bets in, 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. We also had CoreWeave. Um, and then on the business models themselves, let's play a, a scale AI and software to help them scale on the hyperscaler side and, and focus the balance of our capital on our other mega trends where the AI has been embedded into all businesses. So you have exposure to it Throughout cyber and SaaS, you have exposure to it in FinTech, you have exposure to it in consumer. Companies today that are, are created without AI embedded in their DNA, like why? Why would you do it? If you're not gonna, if you don't put it in there, like why? The challenge you have in our industry is you have vintages 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. We call them, there's two types of companies that were, that are big and private that aren't in AI. They're kind of, we talk internally, we call them vampires and zombies. Because they're massive. Many of them are profitable. They have to now implement AI in their business models. And you have some that are gonna get out of it and be okay. And t…

AI assessment note: “No, I mean, I think for us, um, our view is take a few concentrated bets”

Q Okay. So tell me, Whose life do you secretly admire, and why?

A I, I look at, because of my background in sports, who I admire, I think, the longevity of like a Cal Ripken junior in baseball, who basically for 16 straight seasons didn't miss a Major League Baseball game. Major League Baseball plays a 160 games a year. For 16 years, from the time the guy was 22 to the time he was 38, didn't miss a, didn't miss a start. The grind that that, and a lot of people, you know, people talk about records in sports and, you know, all of the high-flying athletes that people recognize in their accomplishments. Here's a guy who was a grinder, played third base, hard position to play in baseball. You know, I know you're a cricket guy, but, but study it up. 16 years, not miss a game. Of course, he's in the baseball Hall of Fame and celebrated in that way, but a good player, not, not, 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. That to me, we talk about our 20 mile march every day at G squared. Like it's a 20 mile march, rain or shine, we're marching 20 miles. And we're gonna make progress. That is a different kind of intestinal fortitude in a set of massive steel balls that you just don't get in generations today. What that guy accomplished is, is insurmountable. The…

AI assessment note: “who I admire, I think, the longevity of like a Cal Ripken junior”

Q What price is it going in, just kind of give or take?

A Yeah, so, um, in many ways, uh, we, we did it at the time in which it was perfect because you had Adele announced she was leaving the platform. You had Apple Music really taking market share. Um, and you, you had Taylor Swift saying, I want my library off. And, and Daniel Ek came out, and I think one of the smartest things he's ever done, and he agreed with the artists. He 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 aha moment where we can triple down. Nobody else knows this information. You buy from all the people who are scared to death and you do the counterintuitive thing and you, you, 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.

AI assessment note: “we bought it like a 50% discount to the current financing round”

Q What was it about it that was made?

A At that time, the penetration of the usership in, in, in Sweden was like, 25% of the population used it. I mean, that's amazing. 25% of the population used the product. And you're like, it's already cool because you're using it. And of course, Apple music, and I think that beats and, you know, uh, title and all these, you know, SoundCloud, all these competitors, but what they divulged to us in that one-on-one personal meeting after saying no to us for six straight days, um, was the fact that the record labels were also investors. That to me was like, ok, 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 a hundred and fifty million dollars to go find.

AI assessment note: “was the fact that the record labels were also investors.”

Q And in what way? Because it's a very common.

A Yeah, it's because people want to, people want to pat themselves on the back for the wins and deflate the losses, or deflect the losses, excuse me. I think if you want to build a firm, That stands the test of time. The logo makes the investment. It withstands any transition period in any leadership role in the firm because the logo made it, not the individual. And that's what I'm, that's what we're trying to build at G squared is when I look out 20 years from now and say, where do I want it to be? I want, you know, hopefully 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 like the Jim Simmons, 40% annualized IRR for 20 years.

AI assessment note: “people want to pat themselves on the back for the wins and deflect the losses”

Q I'm sorry, dude, how do you get in touch with Jack Ma's family office to buy shares from them?

A I mean, that's the story of my life. It's like, you know, it's, it's, it's a bit, a bit of luck. You, you meet an alum that I knew, knew somebody that knew somebody and, you know, Kind of introduced me to a gentleman's name was Barry Purcell, who was running, um, some of Jack Ma's money in Virginia of all places, I believe. And he said, Hey, we have some shares to sell. I'm like, ok. Hired a group in India to do some DD, because I had like two people. And wrote me an investment committee. Oh yeah, my early investment committee memos and the early vintages were outsourced to, you know, a group of really smart, um, analysts in India, that you could pay a fraction of what you could pay talent in the US. And I didn't have any money to invest in talent.

AI assessment note: “introduced me to a gentleman's name was Barry Purcell, who was running”

Q I agree with that. So why did you sell at 25 then? You just thought it was-

A Okay. Funny story. Um, And personally, you know, you have experiences with companies and very frustrating experience with Instacart during COVID where, you know, it went from Whole Foods only pickers and grocery shoppers, which was an amazing service, right? To 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, you know, um, and, uh, it's just like, I can't get the order. It just can't, 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.

AI assessment note: “I was like, it's time. I just gotta get out.”

Q For people that don't know, what does that mean?

A It means you embed IRR hurdles and multiples in the paper. So regardless if you say the business is worth eight billion on paper, the company has to generate you a 25% IRR or a two and a half X, whichever 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 Spencer and I to get together and say, What, what were we thinking? We have to try to save this thing. Our LPs trusted us with a billion at that .1000000005.

AI assessment note: “It means you embed IRR hurdles and multiples in the paper.”