YouSaid · the spoken record

Larry Aschebrook

lines on the record: 146
first: 2025-06-16
most recent: 2025-06-16
sittings or episodes: 1
sources: podcast

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“Well, thanks, Harry. Congratulations on what you've built. I'm a huge fan, and I think you're only in the beginning of what you're building. And I'm going to be cheering for you along the way.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I told you about the theanois that theanos helped me. That was a 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. It's that productive paranoia that it's great today, but the wheels are going to fall off. And 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think I need to continue to grow and be more open minded in which I have and I full trust now in co-PM of mine who I think is one of the smartest people I've ever met and a 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 And I should listen to more people in their advice that they give me. And that's 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“My belief is that TVPI and MOIC are not the stats that people should be focused on, and they are. I think they're fake numbers.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Where endowments miss the boat, and by the way, I'd love to have many of them. We don't. I think they chased the wrong statistics.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Continuation funds, though I find a bit more interesting today than they were in the early inceptions because now you only want, they will only buy your good assets. So now they've really gotten smart. That's really interesting space right now.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 in private.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Here in London, guy committed on the spot and said, I'll sign the forms for $20 million. First meeting said, I'll do it. Never happened to me before. And it was here in London longtime LP still with us today. Saw the, I probably didn't even care about the strategy. Just I think like me and said he'll do it. That was most memorable for me. Yeah.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 led to unfortunately some really good people moving on that otherwise I would still like to be on the journey with me.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, 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 don't know, Cal Ripkin 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 to 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 you loved it. And it was your passion And that's where people should find their work life balance when your work is your life, your life is balanced.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Study it up. 16 years, not miss a game. Of course, he's in the baseball hall of him even 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. 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 twenty miles, and we're going to make progress. That is a different kind of intestinal 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 of baseball that will accomplish what he did.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I look at because of my background in sports, who do I admire? I think the longevity of a Cal Ripkin 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, from the time the guy was 22 to the time he was 38, didn't miss a start. You know, people talk about records and sports and, you know, all of the high-flying athletes that people recognize and their accomplishments. Here's a guy who was a grinder, played third base, hard positioned to play in baseball. I know you're a cricket guy, but.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Building something that then you don't realize that people outside of your small sphere recognize as something positive and that is something that you're randomly faced with. Like this conversation for me is I'm a huge fan. It's like sports radio, longtime 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 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 staying focused on the logo and not me individually has led to this moment. And that tells me that we all, for all of our flaws, which we have many, there's something in the water at G squared that works, and we're going to keep grinding and doing it.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, immunity to losses would be nice to say that you should do that because maybe you'd be happier plus the money. Maybe you're 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 the dollar amount is, that the win is what gives me satisfaction. And the loss is what hurts. Like I spent a lot of time talking to you about the losses because that's, I can remember mostly every moment of those. And as an athlete, I remember all the failures.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. And I think you see that across sports. I think you see it across business. I think you see it about high performing CEOs.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 won't have to go through that. That'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 maintain.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“When I was growing up, I thought if I could just make $5,000 a month, I would be set. If I could just make $5,000 a month, own 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. But money doesn't make you happy. I think it makes your life complex. How you handle that money is important.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“No, no, but we had come off in fairness to us. We just came off a great outcome in Lyft. 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 Lyft Nuber? And I gave him my opinion on both. And he's like, well, there's this 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 8 to 10x. Bolt, yet to be determined, but let's just assume it's somewhere between 50% and face value of what Sequoia paid. It's 6%, seven X. And now it's a big business. And Marcus has found phenomenal, a young kid building that business thesis was, we'll all go where Uber's not and do it profitably because I don't have any money.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Early whiz and probably early Spotify. Both of those were in Bolt. The early ride hailing, it's yet to be determined Marcus Villig business. We were the first institutional money from the North America in that business. Those first investments we made in all three of those are probably 10X.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Actually, somewhat of the inverse is you have to be able willing to sell your winners to have sustainable business model and to generate the return that will actually drive your Harry's fund forward.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, then 10 seconds. Yeah, that's the classic. That's the classic. Sell your dogs and keep your winners. And I think it's.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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. 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Price increases. No, and then, by the way, layer some secondary on lower the cost basis, and you have you can make a 5x in three years. Yeah, no, it's great idea. I think that there's long in the tooth companies from 20. 15 vintages.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“They're chasing now. You have incumbents that are large. There's two types of companies 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 going to get out of it and be okay. Those are the vampires. And the zombies are dead. There's hundreds of them.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. We also had Corweaf. And then on the business models themselves, let's play a scale AI and software to help them scale on the hyperscaler side and focus the balance of our capital on our other megatrends where 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 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 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, you know, that's a little small area, but we like you. Will you settle on nine? Sure, I'll give you $9 million. That's how we started. And then we went on to build a $200 million position. It takes that buy-in. And so you go back to Anthropic and the others, you know, 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 in my opinion is unstoppable That in OpenAI, they're just the beginning. So how do you play the space? You go to the winners because I have a shorter thesis.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 at our LP day. Half the things they say, I don't even understand what they're talking about. Scares the shit out of me, the world, after talking to the three of them. What's 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. They're humble people. They've made a lot of money. And some of them live in like a one bedroom apartment in Tel Aviv. I went to see them in Tel Aviv. Went to see a bunch of companies. We'll leave the other ones out. A couple of them wouldn't even see me. This is after I managed five plus million dollars. Guys welcomed me in, gave me a sweatshirt. How you doing? I'm 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 3 million bucks.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Now you're talking like an early stage investor, Harry. I don't give a shit about the dilution. I care about the price I pay in dollars and the price I'm going to sell it at in dollars. I am focused on DPI, not MOIC. I don't care about the dilution.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's if you and Spencer McLeod should start a fun together. He's amazing. He's my co-PM. He believes the same thing.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“What's holding back the next generation of the LLMs to get to anthropic and open AI scale? In three years, who's going to rival them? Just answered your own question, Harry.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, TS has a great operator So, I think what you have to build a portfolio across the four megatrends for us, the way we look at it is you have to diversify that risk. So you have SAS, 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 megatrends 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 last quarter talk about growth. I 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 owned 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“So, yeah, Revolutes in our 2018 vintage, where sometimes, and we have them in every vintage. In our current vintage, we have chime, awesome business, believed in our business model, but it went so fast that you can't build over time dollar cost averaging in through lots of transactions, you can't build a scalable position if the company goes from zero to 100. No time. You know, Wiz was very short for us. Our 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 Wiz 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 stress they had in the business and now more of a focused and Germany versus kind of a continental play. And then we had Revolute. What a great little pool of companies, right?”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, well before. I think four megatrends 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 fund, 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“I wouldn't so the way we run it today is the way I think people should run their 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 are our top 10 positions. A couple LLMs, the high flyers, companies like Fanatics, Wiz, Databricks, Turo, the Airbnb of cars, Monzo, companies like that. where there's 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”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Hindsight being 2020, 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Just to be able to solve the problems that they have, to your point of being relevant to the rofer. All you can do is ones and twos, 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 of shares, when they buy into your strategy, when Daniel X says, hey, you guys are interesting to us. Oh, by the way, here's $150 million for the 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. 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 a significant part of our strategy. Over time, it's more normalized today. It's about a billion five. It'll be 700 million. It's still a lot. The mistake we made in 2021 vintage, or 2020 vintage, is we didn't just do co-investments around our core positions. We had LPs coming to us saying, hey, I built my forchin and let's say wellness. I 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Who kind of going through our co investment process in the early vintages, let's say vintage one through four, in some cases we were four times co-investment to fund investment because four times, but here's why, because the type of companies that we were interested in investing in, we weren't large enough to make a difference.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 of capital between capital actually lost and investors that you can't bring back. It was a monumental miss on our part.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 vintages from LPs”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“It should just continue deeper penetration. Well, yes. 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. Look, today it's still operating Turkey. It's a big business. You got a lot of sophisticated people from Mubadil in there working with the business. You've got people inside the business that want to win. You 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, you know, they deserve a good outcome. And that's the piece of our investing is a secondary investor. You 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, we still hold it. It's now business focused in Turkey and lots of great people in the business working. And I'm still on the board, so I'll be careful in some of the things I say.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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 for me.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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, little old G squared amongst giants, it was like you were a 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Was nuts in 2021 and created a lot of unintended consequences that we can chat about and different from our normal co-investment model, which we went back to from that period. But anyway, the long story short was, I think the major mistake I made there was not willing to just walk away.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Total first was like 50 million bucks in total between secondary primary. We got that plus sum and value of Gatir. And then the next check was $100 million to restructure that equity to pull it forward. So you got 200 million of 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...”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“Cash out? We did get a little bit of cash, and we got most of the preferred value in the transaction. So four or five shareholders of guerrillas 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. Getir valued at $10 billion. Next three years were some of the worst of my life. 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.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source
“So, for a group of shareholders, we were a part of helping structure alongside five others. It actually was a good deal. We actually got good value for our money.”
2025-06-16 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source