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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“Much qualitative, too much my gut, my feel, too much who else is in the room, too much the soft stuff that venture capitalists and growth managers like to pride themselves about. And our strategy has to be about the numbers. It has to be cut and dry, cutthroat. Does it work financially or not? Because at our stage, unlike yours, in a lot of ways, I envy your seat because if you pay 50 pre or 100 pre if it's a good business, you're still going to make a 5x. 10 pre 50 pre does it really matter for you? Maybe for me? Is it 3 billion or 2.5 billion? You walk that forward. I can't make my 2.5x net in a five-year period if I miss that. Now I get an okay return, but I'm not rehired.”
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, a few things about that period that is the rationality leaving the room that you want to protect yourself. Guardrails are important. A good friend of mine, and I know you had him on the show. I'm a huge fan of what they've done, Mitchell Green. The best things in life are copied in some ways. You know, he has his lead edge eight. We have RG28. Sorry, Mitch, we kind of borrowed it from you.”
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, that's something I've spent a lot of time in the last few years trying to figure out because 2021, all rationality left the room. 2020, 2021 and us, like everyone else, just kept deploying 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
“We sold most of before the IPO But you'd be surprised, I think one of the issues with Silicon Valley, one of the benefits of being in Chicago is we isolate ourselves a bit from the herd mentality. Sometimes it's like sheep. They just jump one on after another and they buy more stock and things that you see that you should sell. And it just takes one brand name to jump on board and 10 others jump on board. And we just kept selling our lift stock to others. You know, I get why they did it. It was a value play compared to Uber. And it went on to work for them. But we made our multiple and went home and distributed the cash.”
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 Uber chose to go public, it was a tough time. Today, Uber's valued off a gross profit, which is, I think, a good metric for them. And I don't think when it went public, it was rewarded properly. In our business model, we don't hold rarely do we hold post-public. Oftentimes we sell before they're public. And as it went public at the price it did on a converted basis, we were underwater. We lost like 20 cents on the dollar. And Lyft, we made like a 3x.”
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
“Often in our thesis, we'll back two businesses trying to attack the same thing. Lyft in that fund became the value play. We sold it and made 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
“It opened the door. And Johann Berquist and Peter Grandelius, they're the two people that have made probably the most direct impact to my life because they trusted that we could do it and they put their names on the line to Daniel Eck that we could actually achieve it. And then we went and somehow, you know, Spencer and I, Spencer, poor guy got shingles. He literally got shingles. He was like 23 years, four years old. Got shingles. You never hear him.”
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
“But that fund also, by the way, that fund also had Lyft, Uber. SpaceX, Instacart, Impossible Foods. The list goes on and on of companies because of Spotify's acceptance of our model.”
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
“One million increase. Fewer investors, thank God. And then you get to a $380 million pool of capital. And in that, you take a lot of concentration in Spotify. But on top of the concentration we had, we did another $700 million in co-invest.”
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 kept buying. So we pooled a bunch of money together. Some of it we were able to put into our fund. Others, we had very prominent, very, very prominent logos come into our SPVs to buy the stock because we locked in the access. So you have this journey. You start, you're just hustling. You get to 35 million. The second fund was 36 million raise in a year.”
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, so in many ways, we did it at the time in which it was perfect because you had Adele announce she was leaving the platform. You had Apple Music taking market share. And you had Taylor Swift saying, I want my library off. And Daniel Eck came out. And I think one of the smartest things he's ever done. And he agreed with the artist. 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 take the bet. And we did. And it worked. And we bought at like a 50% discount to the current financing round. And we just kept buying it there for the next two 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
“I wasn't exactly that pleasant, Harry, but it worked. And God bless my wife. She's like, Do you love this business? I'm like, it's the most amazing business I've ever seen. She's like, well, how do you, how do we figure out how to own the 9 million? And we figured it out. And that nine turned into a very different number. And that was the life-changing event for me. Spotify buying into our business model. We then went on to become a top 10 global shareholder of Spotify, went as far as to putting up signs in their break room. We'll buy your shares, buying all these odd lot transactions along the way and build a huge position. And it ended up being like a billion dollar outcome to RLPs. Forty percent of my third fund went into Spotify.”
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
“And we got to day 59, and we had sent $141 million to one of the earliest investors, very predominant Norwegian fund. We'll leave their name out of it. Awesome founder of that fund, who is an iconic pop star or sorry, heavy metal star in music in his own right, very serious guy. And we have 141 million dollars we've sent him and the rofer ends. And if we don't send them the $9 million, the deal blows up. And I don't have $9 million to my name. So I borrow it from 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
“Yeah, so the way that the transfer process worked on that business is pretty interesting. It actually gave you time. So you signed the documents today. It took like 60 days to clear. So we had like, let's say 25 million ready to go. Awesome. Concentrated position on a $300 million fund. We're going to start. Let's do it. We had $4 million they said yes to. We'll take another 25. So we went out and went on a world tour with our thesis. Spencer and I different countries.”
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
“At that time, the penetration of the usership in Sweden was like 25% of the population used it. That's amazing. 25% of the population used the product. It's already cool because you're using it. And of course, Apple Music and I think the beats and title and all these, you know, SoundCloud, all these competitors. But what they divulge to us in that one-on-one personal meeting after saying no to us for six straight days was the fact that the record labels were also investors. That to me was like This is like Napster on steroids and it worked and obviously they went on to create amazing shareholder value. It's one of the best businesses we ever invested in and we had 150 million dollars to go find.”
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
“This was mosaic theory. So most of the early stuff had to be mosaic theory because companies until really Spotify. So the early wins are gathering data, trying through public sources, but it's not really available. You're trying to gather through contacts and putting as many feelers out and then sending all this information to what became our own research team to develop a thesis around it. And then the Trojan horse became the check to get the info. So in that land and expand strategy that we run as it's developed often, that first check is kind of that Trojan horse. You like it, you've done some mosaic theory work, you think it works, but you don't really know. You go in. So we go in give us a whole deep dive on the business, and it's amazing. It's like nothing I ever could imagine. It's nothing I've seen before.”
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 we also became an investor in the EU ride helling business. And before we left the meeting, they were like, Do you think you could buy $150 million worth of stock? And I said, sure. And I didn't have the money because we were in the process of raising the fund. And I think we had like closed on $125 million.”
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
“Came. We spent a week there in the terrible. We had a new baby. We were staying in an Airbnb that we rented, which became a great investment for us later on. But anyway, we started going to get a meeting. And finally, this young lawyer, Peter Grandelius, took pity on us in the waiting room and took a meeting. And we pitched, I look back and all the pitches I ever gave a company on how we could add value with a small fondant, a lot of co-investment. Spotify's what it's become, but they're like, yeah, we could use the help. Very humble, very...”
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, one of the first employees I hired young guy at a Berkeley, he's now my co PM, Spencer McLeod. He's a living caricature of what Silicon Valley is. He was working as an analyst with me. This is like 2014. I think he's like 22 years old at the time. I was telling him this story about how my mind exploded when I was in college and I could download Metallicon, Napster. And he's like, you know, you've heard of Spotify, right? I'm like, yeah. He's like, well, maybe we should buy some shares in Spotify. And literally, that's kind of how it started. And we started searching around and we found a celebrity that was going through an unfortunate change of life scenario and a divorce. And he like $4 million a stock. And we had a $300 million fund at this point. I'm like, yeah, let's buy it. Well, Spotify had this interesting process of how they approved shareholders. It was kind of onerous and difficult. And my mentality was they're not responding, so let's go see them. So literally Spencer and I flew without an appointment to Stockholm. My wife.”
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
“Rash and it's very, very different. It's your differentiate your business by sitting here and doing this and in the know, and how many awesome people do you get to talk to to find and get the references to the next great thing? You have figured out a niche. Most don't. Most say, oh, you know, I worked at XYZ old logo firm for ten years and I know how to operate. I'm going to start a VC firm. I'm going to go to 10 LPs that were in that old one that I got to know and give me some 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
“All those things, deploy as you go, but also create a firm that's different. The world doesn't need just another early stage seed manager, growth manager, crossover fund. There's so many.”
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 fully registered, kind of like a hedge fund. So you're seeing a lot of people opt into that. Why? Because they want to pair primaries and secondaries together and they want to do some one-off secondaries big checks. One of the things from the early vintages that teased out that we still do today, it was the frequency of transactions and touch points of really micro transactions sub $2 million, let's say today on a $2 billion fund give you a lot of interim data that you would not normally get in that touch point as a primary investor. It starts to provide you that Trojan horse moment to know when to triple down on a whiz, which we did in our 2022 vintage fund and have the outcome that we're going to have those founders are amazing, but to make 3x in 18 months is because of what they created, but the opportunity to do that is because you offer something different than others. And that's to the people you asked me a question earlier. If you're going to start raising a fund today, what would you do? Yeah, raising money, don't take no for an answer, open every door.”
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
“Not always, no. The market on direct secondary buying is really fragmented. So, first of all, in the US, you have to be regulated bit of a different way than most fund managers to do it in quantity.”
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 misconception of what we do. I love it because it actually is when a good LP, the light bulb goes off, they realize that it's the opposite of that. We get primary level data. We touch and feel the founders because the value of the discount is back and they value the work that you do today because there's still a massive need of liquidity, but they want a trusted partner. And that's part of the journey to how we got here today is by doing something different.”
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, right. I'm trying. I'm trying. I'm just running through a wall. It's there. I think that early vintages up until 2020, all of those vintages, you were getting a lot of value by being a secondary direct buyer. Now, that's a key differentiator. What I wanted was and still to this day what I want is I want to touch and feel the founders, the companies, the data. I was amazed by what I started, the paradigm that opened for me mentally was something that I had never tapped into my entire life. This was really interesting what these companies are doing.”
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
“Yet today, then there's no options for liquidity. It wasn't that. It was you actually could get really good value. And I think one of the interesting things about the cycle we've been in the last 15 years is, you know, now we look back at the funds and dissect them and say, what kind of value did you get as being a secondary direct buyer? In early vintages, we got like 35 cents on the dollar by being a secondary direct buyer over primary buyers because there was no other secondary buyers because the lottery reasons a little credit, hard work, drive, run through a wall regardless of how thick it is and just keep hitting it until it falls. That's my mentality, which is good and bad.”
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
“Timing at that period, no liquidity, large private valuations, really differentiated, unchallenged business models. No one was doing anything like them. The liquidity window was still early from the financial crisis because you look at the number of IPOs from 2010 to 14, there wasn't many.”
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 for you. You're going to love it. You're going to love it. It's really going to help your first time manager. I really want you to succeed.”
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
“But what do all those have in common, right? And now you look back and say, well, how do you do that? And there were some dogs in there, some clean tech shit that Client Perkins sold me that was just a flaming bag of turds on your front porch. Like, look at this guy. He's energetic. Let's give him some garbage. And that's what the old line Silicon Valley firms did in the beginning. Oh, yeah, we'll let you in the syndicate. Sure. How much are you putting in? Oh, we're putting in very little, but our LPs are co-investing a lot. That's an alarm bell now that you know it's ringing as loud as like a four alarm fire.”
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
“Knowing it. Then you look back at the returns and you say, Holy shit, it works. Start off with a couple small checks. All of a sudden you keep getting the data. And I'm sending it yes to my awesome group in India to give me the data back. I'm sending it over there. Hey, it's amazing. You work 24 7 time zones. But anyway, what comes back is hey, these five companies are better. And so then what I did is I put a lot of concentration in. Which some people are not comfortable with. Hopefully, 90% of our risk are in 10 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 sounds like that, but really for me it was fewer companies because ultimately how do I get liquidity if I have 50 companies? It's my money. I don't have much. I've got a few people who trusted me. I want to get their money in and out as quick as I can because as you're trying to raise that fund and you know what it's like people want track record they want pedigree you know what's your TVPI going to be what's your moik gonna be i had people who were running their own businesses give me a little bit of money and say i want the money back quick i want optionality to it so from the early days it was how can i build a strategy that i can actually make a good living at to have velocity of the capital come back and optionality and today our business is become that in the early generation of it was start off with little checks because i didn't have much money as i raised more money the challenge of raising the first vintages the benefit of that was you didn't have a lot to deploy so i'm deploying it as i have it so inherently i'm doing this land and expand without even”
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, so from the beginning again, you don't know what you don't know. I didn't like the idea in my personality is kind of you go big or go home. I didn't like the idea of trying to manage a lot of these positions because I didn't really know how. So my idea was I wanted to put a little bit of money in, understand the businesses, and then pick a few and put all my money in. Today we call it land and expand. We have all this bullshit that we say that our marketing. Our marketing team, our team is second to none.”
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, Alibaba was for me there's a business here, it was grinding, grinding, grinding. That was the first one that was material for me as 2014 Alibaba.”
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 mean, that's the story of my life. It's like, you know, it's a bit of luck, you meet alum that I knew, knew somebody that knew somebody and kind of introduced me to a gentleman's name was Barry Purcell, who was running Jack Maws money in Virginia of all places, I believe. And he said, hey, we have some shares to sell. I'm like, okay, 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 a group of really smart analysts in India. 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.”
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 real momentum happened in 2014, and that's when I really felt the power of what I was trying to do when Alibaba goes 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
“$150 million, we raised a billion four and then turned down another $700 million in very short period of time. And companies, by the way, also raised a ton of money. Insane 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
“We've had to say, hey, I'm raising a new fund and have two billion show up in two months. We don't have the benefit of that. I'm okay with that because I think the way we're forced to raise money makes us better. Now 2021 was very different. I was set up my farm. You sat in your underwear probably and raised in three months, I don't know what you raised.”
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, first of all, if I knew then what I know today, I'm not sure I would start the journey because I didn't know how hard it would be. I just want to do something different with my life, try to create value for my family and try to set my children up for a different future than I had. I was lucky. I grew up. My siblings grew up in the same house as me. We don't have the same life today. I got out of the squalor because I could run and throw and catch. My siblings didn't have that benefit. I didn't want my children who knows what their outcome would be. So the whole genesis of it for me was to try to create something and seeing opportunity and capitalize on it. So with my mentality still to this day, raising billion, two billion dollar funds is the money's there, you close. Start deploying it. Build a portfolio. Show some improvement in Nav. It is inertia that makes it easier. I don't have the benefit even today with the returns that we've had in the DPI.”
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
“And by the way, my font size is I don't have a fund, I just have like 200 grand in my name. I'd like to buy $10,000 worth of Twitter stock. That conversation obviously wouldn't go anywhere.”
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, 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. Average age from inception to IPO was like three years leading up to 2010 from 2010 to 2018, it got to like seven or eight years. Today our average portfolio company is 15 years old. So there was to me something that was clear there, which was there's an opportunity to buy shares from these people, have no liquidity, and you should be able to make more of a return than also companies win return my phone call, frankly, because I had like no money. And hey, Twitter, hey, Dorsey. My name is Larry Ashbrook. I'm a retread athlete that wants to become a venture capitalist. Can I invest in Twitter?”
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 mean, Twitter and Alibaba were pretty good. Those were when I realized there's something here. Making a little bit of money in your whole life working 10 years in a profession, thinking you've kind of made it coming from a group in an orange trailer in Might in Utah, you know? Having like 100 grand in your bank account one random Tuesday felt pretty good. And I said, this is something interesting. Got some advice. You should raise some third party capital. And that's when I really understood the power of OPM, other people's money. I went around all those alums who basically, I think, gave me some money because they were tired of me asking that I worked at five different large academic institutions.”
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, half a nothing's nothing. My wife came to our marriage with $50,000. I had went through a pretty tough financial situation. Rightfully so, my former wife kind of took what I had raising my three young kids at the time. And my wife and I today, we started a journey together. And she backed me with the 50 grand in my small amount of retirement. I just started buying Twitter shares and Alibaba stock from Jack Maw's family office. And then, holy shit, it worked.”
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, so small. You know, I wanted to make a change. I was working in college athletics. That was changing as it's become today, this whole thing players should get paid and coaches salaries. And pretty soon the inmates were running the asylum, sort of speak. And I was like, this isn't my passion. This is not where I came from. I want to make a change as a former athlete. Maybe I can use my brain, not my brawn. I cashed in my retirement. I went through a divorce, got remarried, had nothing. I had no money. And I just had paid the tax on my retirement, started buying these shares.”
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 guess it's not knowing what you don't know, and 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 ask people, 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 Carey School of Business at Arizona State, one-page form that then we sent to the company to buy stock. And it still floats around. I got it back from a broker not that long ago. And it's like literally the form I created in 2010. One page and it's binding though. That's scary. It's binding. Which has bitten me in the ass a few times.”
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, for me, it wasn't really, hey, I want to be a venture capitalist and manage billions of dollars. I come from nothing, 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 at 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. 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 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 follow Twitter. I like Twitter. You know, what about early Uber? What about early Spotify? And I just started buying shares from my classmates with my.”
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 mean, we made ridiculous sums of money for LPs in that period. We were the largest shareholder of Coursera, $800 million back to LPs on Coursera. We made a ton of money on Lyft and we lost money on Uber. 40% of my third fund went into Spotify. I went back to our LPs and said, listen, we fucked up. We need to pivot. We need another 300 million bucks because I need to protect this thing. The next three years were some of the worst of my life.”
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