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Gokul Rajaram

lines on the record: 81
first: 2026-03-16
most recent: 2026-03-16
sittings or episodes: 1
sources: podcast

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“I actually am a huge fan of it. I feel even in companies, I feel the companies that are not hiring young people, they're making a huge mistake because young people are more AI maxed, as you could call it, like looks maxing, AI maxing than anybody else. The younger people are adopting tools better and they just live and breathe differently than others. So I'm a huge fan. I've actually invested in more dropouts as an angel now over the last few months than I have invested in by rest of the last 15 years I've been investing. So I don't think it's the right thing to be honest for many of them to be dropping out and starting. I do think they could benefit socially, emotionally, etc. But some of them are just exceptional. I don't think all of them are. But I do think this crop is going to produce some incredible founders.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“The most ambitious entrepreneurs are finally tackling the hardest problems. The ambition with AI especially as unlocked is just incredible. The ambition of entrepreneurs tackling the hardest problem facing humanity and society is just absolutely incredible. How can you not be optimistic when you have Elon going? I mean, I think we have now these entrepreneurs who are role models who are not just building these small companies, but they're truly taking on humanity problems. So the answer to Peter Thiel's question of we were looking for flying cars and we got 140 character apps I think has been is finally I think it's coming into focus”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Quince, quince, man. Most recently, Quince, but to be honest, even bigger miss than that in some ways is not a miss in terms of investing. It's that I couldn't predict the face who could be a $2 trillion company. When our company was going to be acquired by Facebook, I was arguing with the Corp Dev team at Facebook and we were arguing over the terminal value of Facebook and we had to put China into the mix saying, we're going to take China will get us to 40 billion in market cap. And we were arguing whether it was 20 billion and 40 billion in several years from then this is in like 2010. And turns out in less than 10 years, 11 years, it was a trillion dollar company. So when these things work, they work in a scale that is unimaginable. And even at Google, I remember very well after the IPO, I was there doing the IPO and we were sitting around with a bunch of PMs and we were saying, man, the company is valued at 30 billion. It's too expensive, too expensive. And so you just, these things compound. It's just incredible to see these things become trillion dollar companies. So Facebook and Google in some ways the biggest missus in terms of not being able to predict that they were going to be multi-trillion dollar companies.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I think they are all different. I would say all four of them, Larry, Mark, Jack, and Tony, and now Brian Armstrong, Bill, and Bennett Pinterest. It's a hard one. I think all four of them have different superpowers. I would say the best technical CEO, Larry Page, the best growth-centric CEO, Mark Zuckerberg, the best design-centric CEO, Jack Dorsey, and the best physical world operational CEO, the most likely Jeff Bezos next, Tony Shu.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Leaving Google, leaving Google, I think there was a saying you leave Google only once. So leaving Google to start a company, I was on a pretty incredible trajectory there. I was learning a lot, really enjoying it. It was really tough to leave Google. I don't regret it, but it was very, very hard to leave Google.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“They basically said, I don't know whether they were asking us for it, they literally asked us, okay, so I've actually answered this question, Elfie before.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“First-round capital and benchmark in both. And then Green Oaks. First round would be the seed bench would CSA, and Green Oaks would be the growth.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I know it feels exciting to start a company. Everyone's doing a startup. AI is a new way, but my strong advice is to first get two to three years of work experience at a company, at a good company. You won't regret it. You learn a lot, both the experience and the network of people will be invaluable for you. So just two or three years, don't be impatient. Life is long. Work gets a work experience before starting a company.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I think just seeing a few companies where literally the companies died because the founders were unable to agree. They had everything going, but the founders were just not in the same place and they were just not able to move fast enough and agree on a line on the strategy and change things. So Iration speed just suffers massively if you're pure remote. It doesn't need to be five days a week, but at least three days a week.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I used to think pure remote would scale for early stage companies if you have the right culture, but I don't think that anymore. I think you've got to be in person at least a few days a week. What made you change your mind?”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Think we are going to see a more spin-offs. I do think there is a limit. You're going to see these mega funds train again, more waves of investors, and these investors are going to realize that being a mid-level partner at a mega fund is not all it's cracked out to be. So they're going to spin out and go back to the way of doing things that venture used to be 20, 30 years ago, which is a small group of partners building deep relationships with entrepreneurs.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“They are playing a different game, I think very highly of the mega funds. They've basically gone and they deploy $15 million checks almost as an option and a lead generation for the next round. And their strategy is obviously to have an index at the A of every single good A company and then double down on the ones that truly matter and triple down and quadruple down and do SPVs in them and do specialized funds in them and so on.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Not possible. I don't think with our fund it's possible. I think the ownership is just literally the first round for these companies is, like you said, a billion dollars. So I think it's just too high, the risk reward is just not worth it.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Consumer internet is full of first time extraordinary founders. Mark Zuckerberg, Larry Page, all of these are just first time founders. So those are two archetypes. The third archetype that has come up is AI Labs researchers. And so I think you, you know, that one is a more interesting bag where you have, of course, Dario and the Open AI folks, but then you have a bunch of other labs that came up and ultimately didn't turn out to be anything. So you want to, for these kinds of folks, as a seed investor, you just want to blindly write a check into them. A brilliant young person who's done something extraordinary, a repeat founder, or maybe an A-Lab researcher.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“If you're a seed investor, if you're a pure seed investor, I think you have to do that. I think that's what YC does, right? I think that's actually the right way to do pure seed investing. First round capital, I think, is one of the best seed firms. Guess how many companies they have in their each fund? 80 companies. Why? Because you've got to take 80 debts, which means that some of them, and YC, of course, best seed investor of all time or pre-seed. I mean, you've got to take hundreds of bets because most companies will pivot. But I think as a consolidated portfolio, you've got to basically understand the business and you've got to bet on both the business and the founder unless the founder is an N of one founder in a space. I think there are two categories of actually there's three categories of founders in some ways. There are repeat founders who know a space exceptionally well, who've done it before, you're betting in them again and again to do it. The security is a great example. Security is full of repeat founders. They know the market. They know the customers, all of that. But then there are consumer companies.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“The takeaways that you can't just take an industry and say it's good or bad within every category, there are great companies and there are mediocre companies. And you've got to understand each company's remarkability and differentiation. Quince, for example, had an incredible 35 to 40 percent repeat purchase rate, which was like higher retention than most consumer apps. And so I should have paid more attention to that versus dismissing it. It was literally in the blurb. And I was like, okay, you know, so what? How big can this get?”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Pattern matching too much. I think a good example is Quince recently raised a $10 billion. I saw Quince four years ago when he was at $100 million valuation. And I was like a D2C company, D2C companies were kind of on the downswing. How good can this company be? What do you, I literally just dismissed it. I didn't even look deeper into the company.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly. And you don't have exactly, and that's another uncertainty. So, I do think the secondary markets have been one of the best or most interesting developments over the last few years. And so now all these great companies have pretty liquid secondary markets where you can sell shares. Obviously, there's Roford and so on the company has. I do think there are these hyper-liquid periods in the market now is one of them. So I do think one should be very careful and thoughtful about what the go forward IRR is for any asset one owns and really think carefully about whether one should sell or not.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I think you have an obligation to LPC at least, and I like Fred Wilson's strategy around selling, which is sell a third, hold a third, and trade a third. This is when the asset is completely liquid. But in this case, I think you want to sell at least part of it, especially if the asset is a company that will return a chunk of your fund. So if it's going to return 20, 30, 40% of your fund, you owe it to your LPs to sell a piece of it, especially if the go forward IRR is not compelling.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“As an angel, I used to hold till IPOs. So Figma had many liquidity opportunities during the years, but I kept holding it for 13 years till it went public. I think at the IPO, it was actually priced very nicely, unfortunately, after the IPO, it has been more challenging price-wise. But I think as a fund investor, it becomes interesting. I think there are two situations. One of the things I think most early stage firms get wrong is they just focus on MOIC. They don't focus on IRR. And MOIC is multiple of invested capital. I think IRR matters a lot, as you know. NLP told us about a firm that gave them a 7x MOIC over 20 years. And that was a teens IRR. And that is like, okay, there's something crazy here. I mean, that is a venture firm. And so you've got to look at go forward IRR and your projection. If you go forward IRR at every liquidity opportunity is lower than what you are basically promising your LPs or what you think your fund should have. I think you should sell.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Entrepreneurs, most of them, people in the arena. I think for me, since I'm so trend driven and we really care about what is the thesis, what's a market, the best ways, I think you can talk to investors, but there are always one click away. You've got to talk to people who are in the trenches building products. You've got to understand what's changing in their lives, how they're thinking about the customer. Today's world, you've got to stay close to model companies, for example. So I have people that I meet with at each of the model companies to understand what's coming down the pike, how they are thinking over the world, et cetera. Because like you said, you've got to also understand, we always use a joke, this joke like this was 10 years ago, if you're a startup, which is directly in Google's roadmap, like directly, you should not be building it because Google is very good when something is directly in roadmap. They're like a tank. They'll just roll over you slowly, but it doesn't matter. They were implacable.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“One of my favorite. Neil, you mentioned Neil was in the show. Seven funds have, what, 65 companies overall, or six funds are 65 companies, 11 companies per fund”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Got to be thesis driven first and foremost. I think what we are is we think about what is the thesis. In other words, you've got to have a good sense of who the other companies are and players of in the space and you've got to understand why this company is better than every other company on what dimensions is it better and is that durable enough over a venture time frame which is seven to ten years or even maybe 10 to 12 years now. So you've got to do work. You've got to be thoughtful and patient. Remember what being concentrated does it gives you more time. It gives you more time to meet companies. It gives more time to think. It gives you more time to be helpful to companies. But you don't feel the pressure to deploy on a monthly basis. If you look at a 30 portfolio fund over three years, which is the initial deployment period, you're basically almost investing one company a month. And so that's incredible. I almost feel there's pressure on the folks who do 30 to 40 to do basically one company as a partnership per month. If you're doing green oaks, I think if you would ask me.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Fund. The question is to just want to have the initial stake. You want to increase your property of finding the initial company? There is an explore exploit thing, right? Where do you stop exploring and when do you stop exploiting? So different people have different points of view there.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Founder Fund is a guy called Napoleon Ta who leads a growth practice, and Napoleon basically is the one who decides which of the companies should we double down on. And I think if you double down properly, it changes the complexion of the fund because you have much more insight. I would argue that if you work closely with these founders, you have much more insight into these companies and how they're going to do and even how they think about the future opportunity because you've thought about it with them, then a random company you meet. Now there is a balance there. You don't want to be over concentrated, but I would argue that if you have X number of bets and you work with the founder and you think highly of them, that's why each founder's fund fund is named after the company that makes it like in colloquial terms. There's the annual fund. There's a space X fund, etc. Why? Because at one company is the one that makes it. And that's the reality, Harry. I mean, literally, you have one company most likely, one or two companies that will drive most of the returns of any given.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“There are two ways for operating. I'll give you an example Trade Desk where I'm on the board had two seed investors, IA Ventures, Roger Ellenberg, who's absolutely a goat, and then founder collective, again, goat firm. So they have two completely different philosophies. Founder Collective only does first checks. They never do any pro rata afterwards, period. Roger, on the other hand, doubles down again and again and again. So Trade Desk raised, I think, two or three rounds of financing. That's it and went public very early. It was very hard for them to raise financing. So the multiple that Founder Collective generator was incredible because they only invested at the seed round and they got it at 5 billion or something like that or even more. I think they helped for longer. Well, Roger generated a huge dollar return, even though his multiple was different. So there are two philosophies. My philosophy is more, if you look at founders fund, which I think is one of the best performing funds, a huge part of their success is basically doubling down on the companies that matter.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Very simple. Go and talk to the founders. Go and talk to the founders and see why they chose, especially the earlier stage founders. Go to the seed founders that they invested in and the inception stage founders and ask them, what was different? Why did you choose them? What are the options that you have? And I think you've got to use the data. You're right. Most VC pitchers look the same. What you want to do is dig one level deeper and talk to the founders themselves and understand for each of the last five companies that they've invested in why did this founder pick this firm.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“May not need it. I generally with Keith that on the margins, investors don't add value and the value they add get gets less and less as the company grows. But I do think there are a few points where a few things you can do on the margin. For example, helping them choose between this candidate or that when they're hiring, helping them think about go to market that could make a difference between the company being a mediocre exit or an outcome or being a generation company. You don't need to do everything for them, but just those one or two things that you can help on the margins can hopefully be the difference.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“There's no prepared access. What is proprietaries, your ability to add value? And I think founders, you basically have to, I think, build, if you're just capital and assuming founders will come to you, you're not going to win. But what you have to offer them is something. What you offer them is something very different and unique. What I offer them is something very different. We all have, I think you've got to hone as it...”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so that was an inception round at like some crazy valuation. I mean, very strong valuation, not a crazy valuation, but a strong valuation because Jackie was Jackie and she had built the Banquet Square. She built this bank again. So you want somebody in an industry where they know the inner workings of better than anybody else in the world. And you say you back those people. And that's a much, much better risk reward there. So you want to do a few of those in addition to, you want to do a few incubation seed in addition to CDC. You're doing that in some ways. I think early stage firm, I think you've got to have proprietary founder access and access to founders and their first call when they go to start a company. And then you meet founders, you don't know them before you're kind of betting on traction and so on. You've got to have a mix of both kinds.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“You've got to have a mix of seed and incubation bets and a mix of Series A bets. I don't think you can do purely CDAs out of a fund that's like 200 or 250 million. You've got to have a mix of bets. So the incubation bets are bets you take on founders who are basically the best in the world at what they've done. A good example, I think, was invested in a company. This was before Marathon. But with my marathon partners of the marathon, they led the round with Vinod Coastline and Mickey Malkad Ribbit and a company called Leadbank, which was my colleague Jackie Rees”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“This slightly earlier. It's a tough game, but got to be patient. I think the good news is concentration is your friend in some ways. It can be anyway, it's also your friend. Can we your enemy if you're picking wrong in some ways, but it can be your friend because then you don't feel that you've got to do 10 deals a year. You can do four deals a year and do 15 companies in the portfolio.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't think an investor can do, there are two kinds of deals that investors have to do. One is I think where there is less legibility on the company, where you're betting on there is some early product market fit, there's not 3 million revenue, there's half a million revenue, and that's, like you said, when you get it basically for 50 or sub 100 million, a million or so. But then as soon as you get to 3 or 4, it gets, maybe you can do a couple of deals like that, but I don't think you can build a Series A fund doing deals at $300 or $400 million because it's not going to be enough ownership. Some of these are going to fail, et cetera. So I don't think, I think you can probably all of us, you know, I think even benchmark, I think on your pod or one of the pods, I think Chaitanya mentioned this, where they've done a few of those deals where they have singularity ownership percentages in high valuation companies like Mercor or something like that. But most deals, I think you've got to have double-digit ownership.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“And so that's a challenge, I think. But guess what? Even in VWork, benchmark made money. Benchmark made money at WeWork because they invested early enough. So I think at sub 100 million, maybe that's an arbitrary number. If the company is good, you'll make money regardless.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I think there are two ways I've now realized after many years of doing this at CDNA, price almost doesn't matter if you're right about the company. So I think we just invested whatever the price is. For example, I invested in the seed round of fare back in the eight, nine years ago, 20 million, which is very expensive for a seed round at that time. It was the highest price YC deal at that point. I think it's been $100 or $200 for me. So I think you invest in a company which is great, you have conviction you invest. Now, I think the B, I think B plus, that's when starts destroying returns. I think by then you've got real revenue, real traction. You can pick a generally good company and still get crushed. For example, one of my friends invested in this security company and they had 100 billion revenue. He invested in them at 4 billion. I think they've gotten to 500 million in revenue, but guess what? They're still at 4 billion. And so basically they will not make 1x the capital they invest.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“This is very hard. I think it's a mental thing where you've got to take every opportunity at first principles. We all struggle with it. I think the best venture capital, someone asked me what's the best venture capital bets. I talk about a paradoxical one. I think it's Mike Muritz betting on Instacart. Why? Because he lost $370 million on Webban less than a decade ago. He burnt it through. Same space Appura comes to him. He bets on it. He bets on it after losing hundreds of millions of dollars. It is not all Sekoi money, but the whole thing burned to the ground. And think about the first prince he was thinking needed and the courage needed to make that bet. I think it's brilliant.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“The biggest offense was identity. And friends that in MySpace, you didn't know who the people were, they didn't have the real photo thing. I remember when Facebook had to go into Japan, Japanese cultural norms were that all the Japanese social networks back then were incognito. You couldn't, for some reason, maybe saving face or something, you could not share your real name or your photo. So everyone said Facebook, you've got to adhere to Japanese cultural norms. You've got to change Facebook and make it similar. Mark said, absolutely not. Infinity takes us longer and they succeeded.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Shopify. I remember seeing Shopify at a billion, and I was like, how many e commerce merchants are there really? Or maybe even before a billion, one of the early rounds, Tam felt really concerned. I think what I missed was that Shopify was not just selling e-commerce, it was basically allowing anybody to sell. So it basically changed any entrepreneur on the planet, anybody who wants to sell something. So it wasn't just existing e-commerce merchants. And that's what you want platforms to do. They literally make it possible for every person, every person to think of the possibility of selling or renting their home out or taking a ride, which they never would have thought before, or installing a new presentation app or a note-taking app. They are the biggest hits. They're also the biggest missus. If the bet doesn't lay out, they're screwed. The bet plays out. They could be bigger than anything else. Google, many of them are non-consumption markets. They're new behaviors that didn't exist before. That's in some ways what venture is all about. It's not about existing, it's about new behaviors.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I think non consumption is the biggest challenge. But yes, you can't knock to market sizing, I do bottoms up with the specific segment. And I always know, I think any customer base that has more than 10,000 customers or a few thousand customers, you've got to segment them. There'll be a few different segments. So you want to understand within each segment what the bottoms up propensity to pace, what's the problem you're trying to solve with them. Then you've got to talk to them to understand what the budget is. You've got to do the work. That said, I have misread non-consumption markets many, many times because you just don't know how big it's going to be. It's very hard. Kudos to those who've been able to bet on Uber every time when Uber hit a billion, five billion, 10 billion. I was like, hang on. And then you see your own behavior. Sometimes your own behavior is the proxy for how it's expanding. But with a non-cousin microscope, the hardest.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I think Robert is a good example. I think you've got to have massive scale. I'm an investment company called Atlas, which sells to billionaires. It's the opposite. It's a great business. You need massive scaling. You need a wedge product that is almost cheaper free. I mean, Robin Hood, you have to have free canonically in your thing. Robin Hood obviously offered free stock trading for a long time, and that was their core pitch, and that allowed them to basically get a lot of people. You need to have something free or some hook that is really low cost, that allows you to expand. But it is a harder business because you can't make the ARPU or the average revenue per user is low enough that you need millions, if not tens of millions or hundreds of millions of people. When you sell to very rich people or wealthy people or large enterprises, look at Palantir, which is the business equivalent of selling to wealthy people. They have, I think, what, less than 1,000 customers, maybe even less. And each customer pays them 20 million or 30 million or 100 million or billion. It's an easier business to, obviously it's a very hard business, but you can...”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Say, you don't look at margins, you look to see whether or not they have a product that is compelling enough. For example, I think obviously Disney Plus for every year, I think they increase prices on me. Like they've gone from $20 to $30 to $40 or something like that. Amazon Prime is another one. But this takes many years. But you want the potential. You want to evaluate the potential. Do they have the potential? Do they have the ability to increase prices in the future? It's not something I worry about. I think durability and defensibility is much more of a worry. I think good companies, if they are defensible, they will have the ability to increase margin. That's what I was saying, actually.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“In year one and two, I mean, it doesn't make sense, even years four and five. But you want to have on one side the ability to increase prices. On the second side, you want the ability to cost to get lower. I think that second thing is happening by nature. What you want to see is in addition, the ability to have such a good product and ideally multi-product, a story which makes switching really hard and you can raise prices.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think inference costs are dropping, so you automatically assume that margins in theory should go up. But I think it's not about margins in year one or two. The more defensibility or leverage you have in some ways over your customers and what choices they have, the more pricing leverage you have. So I would rather see margins go up with price increases than cost decreases. A good example is PayPal roll off both of us on our board at Square and you told us that PayPal back in the day raised prices five times in three years because there's such stickiness. They knew their customers really couldn't do anything. And you see, I mean, those are, I mean, Uber, I have to say, I don't know if they have raised price or not, but I know that they've basically changed the economics of how much they pay drivers over time so that their margins have just expanded continuously. And they've also raised prices in different ways. So I think you have two ways of increasing margins. So first of all, you and I both, we don't look at margins.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't know. I don't know why gamma would not create, just like they have taken their riff on PowerPoint, why can't they have their own take on documents or slides the same way? I have to assume it's basically the different kinds of content that people create. Are you on websites?”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Me to be multi product. They can't just be a single product and Go. They will need to have a second product. I'm sure of that. They will need to have a second product. Intuit has multiple products.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Great. They're very good parallel. Non-consumption market. You would never assume why would you ever buy a PowerPoint thing or a presentation thing separately? It's a non-consumption market. It's zero market, but the product is so good, so remarkable that it gets people to buy it separately as a separate SKU. I think we need more of these standalone remarkable products. Intuit is a great example. As you know, Microsoft tried to crush Intuit again and again and again back in the 80s and 90s with bundling everything into office, but Intuit TurboTax survived and thrived.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“I think you want to basically weigh the retention in the light of what they have encountered. You're absolutely right. I think just like you want to weigh the growth of a company in light of, have you gone through any seismic events? If they've not gone through any seismic events, you've got to then take it to the grain of salt. What comparative threats have you faced? Has a single competitor come out? Have you been able to ward off that? Has your retention state strong in light of that? Some of these products like granola, et cetera, we'll see if they are the case, but they are these unique products that really open up non-consumption markets, which means that I would never have actually bought a note taker before, a separate note taker outside of Zoom or something, because Zoom comes with its own note taker.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“of the hood beyond behind all these numbers is two things which I think are the fundamental indicators of business quality customer retention or gross retention and then net revenue retention those two I think are the biggest indicators of quality I would always take a company that's just I should say just is crazy during a triple triple double double with excellent growth and excellent net revenue retention than a company that's growing 10x in a year with really bad customer retention and less than 100 or less than 90% net terminal retention”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Not dead, but it's no longer elicits the jaw dropping awe that it used to a few years ago. As you said, I mean, the one to ten is becoming more and more common and those numbers will basically get you. I mean, lovable could probably go public with that kind of trajectory. Now, the bigger question for me is durability. And it's not even quality, it's durability. Because like you and I discussed, margins can improve over time and will improve over time. So it's not about margins, it's about, is this revenue durable? And so retention is basically very important for me to understand. Are people using it as, I think we saw in the first of AI, we saw many chat GPT, like there was a company called Jasper not to pick on them, but they went from 1 to 40 and then they came back from 40 to 10 or something like maybe 1 to 100 and 100 to 40 within very quick time frames. So there's a lot of tire kickers out there, especially in prosumer products who test the product and then move on to something else. So what you want to look under”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source
“Making is a thing. I think it is a thing you see earlier than earlier, companies are getting these rounds that are valuing them at valuations, which really are eye-opening. That said, I think it won't work unless the company executes on the promise. I think other firms can take it as a signal and decide to pile on or not, but ultimately the company has to execute on the vision. If it doesn't, then it's just a bad bet. So yes, it is there, but it by itself, just because your kingmake doesn't mean they are the king, they still have to execute and justify it. I think the reality is everyone playing different games, right? You and I know being venture capitalists now that somebody with a $10 billion fund is playing a fundamentally different game than somebody with a $400 million fund. And if you try to play the same game they are, you're going to lose. You've got to play the game that you're best equipped to play. Benchmark plays a different game than Sanderson Hollowitz, but both of them play different games. And both of them do well at their game.”
2026-03-16 · The Twenty Minute VC · 20VC: The 8 Moats of Enduring Software Companies: How to Analyse for Durability and Defensibility in a World of AI | Why Dropouts are "AI Maxing" the World & Remote Early-Stage Companies are Dying with Gokul Rajaram · IDENTIFIED FROM THE TRANSCRIPT · source