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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“So we made those investments and made a lot of money for LPs, get introduced to GitHear by one of ours. We have an office in Zurich. We have a team about 10 in Europe. We've been here since 2017. Say, hey, you got to meet this company in Berlin when I'm there visiting. We had a bunch of portfolio companies in Berlin at the time. Met the founders and the business was growing like a weed.”
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
“Is not replicable for others. In 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.”
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
“To $75 million. And some we've done four to get to $200. You have to sell that, going back to raising money as a new manager, be different. Be different because different.”
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 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 and 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. And 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 shareholder that needs to leave. They're going to buy it. And it's really the barbell of the small microtransactions that nobody cares about. Some of our companies, we've built through 50 transactions to get”
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, 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. 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 in a 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?”
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
“Also, for us, the 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 fair way. Don't chase the MOIC. We make a two X net in a five-year period. Cash return, not shares. We stop distributing shares because LPs blame you if they hold 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
“Funny story. Personally, you know, you have experiences with companies, very frustrating experience with Instacart during COVID, where 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. A great experience. And I remember pointing I'm hunkered down at my farm. The world's falling apart. I can't get. The order 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 got 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
“A sequoia make money in the long run on that. They also bought along the way. I mean, Sequoia's business model is fantastic. We have a lot of investments in common. Their partners are awesome. There's a few evergreen structures I'd ever invest in. Theirs is one.”
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
“We need a that's a founders fund special, man. We did a lot of work with Founders Fund early fantastic group of investors there. I think Peter Teal's 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. 18 months. It was amazing. And Spencer McLeod, who was my co-PM, he led that deal and he was like, 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.”
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
“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 kind of the food revolution. We were in Instacart. We were in Postmates. We were in Maiton.”
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
“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, buying stock, people running out the front door because their house is on fire during COVID and us running in with capital. It was fun.”
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
“Toast. Yeah, toast. Awesome business. 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.”
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
“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 is hard.”
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
“Put gasoline on it trades 10, goes up, we can start selling at 7, which would have been about a 2x. 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 guardrails in that to protect from Larry 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
“First investment, 23andMe in, I think, 2617 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 aback by what she was doing and believed in it. And we built a large position in our 2018 vintage fund. I think it was the second largest position in that fund. co-investment we maybe had 50 million in and lp capital maybe 30 or 40 million in during this back craze you know pair up with sir richard branson like what an iconic pair right you got anno mojikowski who's a fantastic founder in my opinion not maybe a great public ceo but awesome founder and visionary of what she wanted to build and the ability to go do it amazing richard branson on top of it awesome let's go”
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
“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 23andMe and Gatir. 23andMe not selling. That was my mistake.”
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
“You go through this phase of building a business where you feel like you have some allegiances to some of the people who helped you get there, 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
“Hopefully she doesn't listen to this, although I'm sure she will. Don't say that out loud because she'll say see Harry's 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
“Agreement was to buy about $50 million of stock over like four months because I was still raising the fund. Anyway, we got a”
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
“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. 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.”
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
“She's like. She's like, that doesn't work. Long story short, the Spider Sense came up going through negotiations to get out of the contract. And then some of the material started to come out. And we just like, hey, we're not doing it. And then actually, I don't think it was formally sued that was threatened to be sued. And I agreed to settle it out of court and gave him a couple 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 23andMe, 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.”
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, the kind of C-suite without her. Something just didn't feel right. We went back and we had that form I told you about binding to transact one page one page simple. Companies love it. It's easy. Things that 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 sign 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 our LPs didn't take the loss. Because that was one of those spider sense moments where it's like, to yours, 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.”
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 Theranose secondary, the big loss there 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 gigantic fraud. I didn't know what it was.”
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
“We've had a lot, and that concentrated equity portfolio you're going to have some monumental misses, hundreds of millions of dollars you're going to light on fire if you have the fortitude to stick to it. So we've got a lot of those lessons to draw upon.”
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, it causes unintended consequences. People want to pat themselves on the back for the wins and deflate the losses and deflect the losses. 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. 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 some grandkids to think about the logo that was built and say, my grandpa built that and it's still there and it's the Jim Simmons 40% annualized IRR for 20 years.”
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
“That's the easy answer 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. We 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.”
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. Some of them have went on to monumental failures that have been well written about. But most are really fundamentally good underlying companies.”
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 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.”
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, the 2020 vintage, we top that up. Remember, as 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, two to a billion five.”
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
“Losing focus of what you're hired to do in 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. That'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.”
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
“Yes, it was difficult because I couldn't believe that I talked myself into it. Silicon Valley coach, me, a person that grew up in a trailer might in Utah, athlete, and I have to have a coach to tell me how great I am. I bought into the whole hook line and sinker bullshit of the entire problem in my opinion of Silicon Valley. So 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
“You go to primary, you go earlier, you do a lot of small cap. Hindsight, the mistake I made was not having, besides thinking we're smarter than we are, is structurally in our business not having the levers to pull. Because 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 201. You start to create this persona that everything works. And pivoting, it was a lot of soul searching. We had a large meeting in...”
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
“Selling, taking a different perspective on multiples and saying you have to get the price to 10x. So you're going back in and assets you overpaid and you're using the secondary market as the 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 the last 12 months of VRR and a SaaS company, privately they traded at 50.”
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 means you in bed 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 whichever's greater. So every day the return's ticking and you walk it out now five years the entire pref stack is totally fucked because the last money in has this ratchet that's just eating up all the value and that pivot and the willingness I think our team, not just me, the willingness 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”
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 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 because I need to protect this thing. And 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, Koto. And we're putting all kinds of structure in where these founders believed their own bullshit. And they said, I'll take the high price top line, but all embed structure in the equity. And so that vintage of all of our vintages has 70% primary and 40% of that has structure.”
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
“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 2025. The multiple is 4. 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 Toast, and they've gone on to create a tremendous amount of shareholder values as a public company. Don't get me wrong.”
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
“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 we 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. We 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. LPs 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.”
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 was more perplexity. And I'm like, wait a second, Toast is $76 a share? What the hell? How is it $76 a share? It's a great business, but $76 a share? Whoa, at the time. Now, Toast is an amazing company, right? Revolutionized 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 restaurateurs. 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. And I started freaking out because we just deployed 900 million dollars between beginning of COVID and 2021, to your point, jumping on board with all these primaries and secondaries. Ah, we're super smart. We can do some primaries too.”
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
“We sold the stock at $36 a share, and it's at $800 million back to LPs on Coursera. $800 million back to LPs on Coursera. That's part of the strategy we get to concentration. And the law of large numbers actually works and it's easier to manage a fund on liquidity. But getting to 2020, the mistakes we made, so you had all these exits. Toast was our largest position in that fund. It's trading at $76 a share. Mitchell Green and I did Toast together. It's like you're popping champagne around the office. You're like, this is, we're so smart. The fucking smartest people in the room. And then I'm on a ski lift in Montana, and I'm looking at, unfortunately, and I'll admit it out loud, Yahoo Finance.”
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 the big ones where the market cap goes in a bad wayholder of Coursera through our strategy. We owned 16% of Coursera when it went public.”
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 herd mentality. I mean, I think that it's all a product of the time you're operating in. You go back to that period. Impossible 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 the...”
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've talked a lot about this openly to RPs because I take pride in going around the world. We have 60 countries and six continents of LPs. 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. We were raising money. 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 had shipped 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 SpaceX stock privately, make a big return. Impossible foods make this huge return.”
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, 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. And if you have confidence in the mousetrap you've built Forex in 10 years, cash on cash return is pretty hard to beat.”
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 don't know. I try not to look at it because it's one of those things you don't want to inflict the self inflicted wound of the pain, but I think it's, I don't know, it's 80, 90 bucks a share”
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
“Oh my god, no, it's like I had an LP longtime LP first vintage, been back every time. I was talking to him the other day about the difficulties of our 2020 vintages and the lessons learned and how more energized today than ever before and how we're going to make it up in spades. And 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 vintages from the proceeds of my first 50 grand I gave you. So, just gives you a perspective. I think we made a 3x on it and sold it at $9 a share.”
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
“You are what you become, so to speak. Yeah, are there businesses that I would love to take a 10 year horizon on? Because I think they're amazing companies. Yes, 100%. But that's not what our LPs have hired us to do. They've hired us specifically for this North Star DPI statistic that I've pitched them on and our team have pitched them on for 15 straight years across seven 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
“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.”
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 LPs are happy. It's also their expectation. Looking for a pat on the back because you did your job is something I talk to our team a lot about. Yeah, it's a big win, but hey, we also lost $400 million of their money over here. Yeah, 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.”
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
“Oh, just massive amounts. I mean, we made 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”
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 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. As long as you don't get caught at the end of that cycle, which happened in 2021. So our earlier vintages were selling into it. Like it was happy days.”
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