YouSaid · the spoken record

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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“For example, even if 100 people are using it and they process zero contracts, in theory, they should get zero. So I think your two kinds of products. You have access products and you have work products. Access products is basically seed-based, like I think ChatGVD Enterprise is a good example. And then work products like Harvey are probably more outcome-based and not seed-based.”
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
“Seed pricing doesn't die. You know why? If you look at ChatGPT Enterprise, ChatGPT Enterprise is price based on seats because seats provide predictability for enterprise buyers, but they don't drive expansion revenue by themselves. So you basically have to bundle a lot more into each seat. So ChatGBT or OpenAI sells seats based on different tiers where they have different functionality. I think Figma sells three different types of seeds. So you're going to see different kinds of seeds. Now, the big challenge is CPS pricing, which you alluded to, is it breaks when the product's core value is not about access, but it's about something doing the work on your behalf. So at that point, charging per user doesn't make sense because user isn't the constraint anymore. It's a workout. So at that point, you've got to go to outcome-based pricing. So for example, if I'm something like Harvey, I don't know how Harvey prices, I bet that they price based purely on how many contracts they process versus how many people are using 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
“I think you need to assume that they will take over huge parts of the service budget in the businesses and that they will not just be a billion dollar company. I believe that there will be a multi-billion dollar company because earlier, I think they were limited to one part of the stack and they were on top of a bunch of systems. Now they're taking over the entire software stack. And that's the thing I like about you. You want founders who are ambitious enough to go after the entire stack, not just the earlier piece of the stack they were in. You want to be the only product that the company uses and you want to replace as much of the digital labor as you can possible. That's the ambition. So what you want to say is what's your market size here in all your customers? How many people do they have that are doing digital work? And do you have the ability to replace all of that payroll over time and all of the other things they're doing and take a part of the payments transaction revenue? And if you think that's a big enough opportunity, that's when you 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
“There are two outcomes for these companies. All of us have those companies in our portfolio. A bunch of them are going to become zombie companies. They're going to try to add AI features as a last dish resort, not succeed, and be sold to PE. The problem is even that may not be a good outcome now because PE itself is struggling to digest the companies they bought a couple of years ago and the prices are reset. They do have good assets. I am seeing in some verticals there are companies merging with each other. I think we'll see if that happens just to create more scale, but it'll be interesting. But hopefully the better outcome that many of them go to is with strong leadership, you basically can burn the bridges and create a completely new AI native product. I think you had the Intercom CEO, right? Finn, great example, podium, another great example. Both of them with their new products have grown to 100 plus million in a couple of years and basically just burned the bridges. This is legacy software.”
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
“We are seeing that we are seeing that. I think the first one most businesses don't want to lay off people. So the way we are seeing it, the first thing that's happening is businesses are outsourcing to third-party BPOs, many of them in India, Philippines, etc. That spend is the easiest to cut because now you can offer the same service higher quality, faster, and 20-30% cheaper. The second thing they do is when somebody leaves, they don't replace that person. And the third thing they do is layoffs. So I think layoff is still maybe a little bit of a while away, but you're seeing absolutely BPO spend. All the call center companies that you mentioned, all the next generation AI, customer service companies, they're going after BPO budgets. I was shocked when I was doing work in this space how many different verticals doctors office, et cetera, use call centers outside the US. They already have budget clearly allocated and there's a better service. So I think it's BPO spent first. Don't replace the person second and then potentially think about laying off.”
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 can. Maybe the mega funds might say, look, it might not be $100 billion outcome, but I think if you're a $200, $300, $400 million fund, you can absolutely create a $10 billion company. Because remember, one of the big changes is that Vertical SaaS does take over labor. And so vertical software, right? It's no longer SaaS. It's basically software as a service, but it is services. So you're going after the service is spent. So one of the interesting things, as you know, is that verticals, mostly, especially if you're selling to small businesses, they spend some amount of tooling, but they spend a tremendous amount on both BPO as well as on human capital, human labor. You need to basically target those two spends. And I think if you do that and you're committed to building the whole product, you can, absolutely.”
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
“Coinbase has 12 doing 100 million revenue. Exactly. You're a horizontal product, you're serving a broad base. I think vertical products, you've got to really own full stack. I think it's harder otherwise to be a $10 plus billion dollar 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 do think these are viable businesses. I don't think they're going to be big businesses. As soon as you do vertical, I don't think you can do one function within a vertical. I think what you want to see there is the ambition and ability to truly own the full stack, build the whole product for the vertical. Service Titan, for example, is a canonical example. It went public last year, great outcome. It's still a sub $10 billion company or something like that. And they own like 30. If you look at the S1, they have 32 different products. And even after selling 32 different products and really being, at least in the US, for any service field services company, they are the canonical company. They still are a $10 billion 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
“Model over time are you fine tuning a model and improving it over time? And then how deeply are you truly embedding the workflow? Are you just a lightweight thing that the underlying CSR record could create? So these are the two things that you have to hang your hat on. A data asset that gets better with every interaction and then a workflow. It's hard, man. I think pure software companies are hard. I think application software companies are hard. You've got to really believe that the founders can ship with great velocity to basically build that and see proof of that compounding.”
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 have some of the other ones which are physical and so on, it becomes easier. If you're a pure software company, which of those apply to you, I think fintech is a good one. I think FinTech goes to these cycles. I think fintech, especially at Marathon, we invest a lot in fintech. We actually think, oh my God, fintech is one of the best models. If you're moving money, you're generally in a good place. So anything touches money, we feel there's a very strong mood there, much more defensible. And so data and workflow modes are the two things you're really hanging your hat on as a software investor. Because if you're not doing fintech. And then I think at early stage it's too hard to know what a distribution motor is unless they have some hack and these hacks never really stand the test of time. Ecosystem too early to say network effects, too early to say. So really physical infrastructure, they don't have any software company scale, they don't have any. So it's really about, okay, go deep into what is the data asset you're creating. Does it get better with time? Do I believe it gets better with time? Are you building your own?”
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
“Changes the experience and the economics. Document processing was a good example. I think Alton recently, you couldn't actually extract structured information from unstructured documents till about six or nine months ago. Now you can reliably dense legal contracts. So your experience around documents needs to be fundamentally different. If you're just getting someone to upload a document in a flow, you need to instantly give them immediate insights from the document while they're uploading it versus the same document upload thing. That's crazy because now you should be able to infer any document that enters what the hell is going on instantly. So you need to re-evaluate every single interaction and say what has changed. That's the biggest difference in product development today. Model capabilities are improving every six months. Because if you have too long.”
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
“It's an interesting thing. The Bolton Air Strategy by itself has a real ceiling, but I think the companies where the Bolton really works are the ones that reframe what the product does, not just add the capability. So I think if you just add AI search, as there's one thing, you just add AI search or you build search as an experience with new UX primitives. One is just an upgrade, the other is doing completely something completely different. So notion, for example, I think very highly of them. I think Notion is adding AI, as you mentioned, they're adding a lot of AI agents. I'm hoping that the way they've added it, I've actually played around with the product. I think it's pretty good. But the AI agents need to now get better based on how the user interact with it. And they need to tune the model for their customer base. Most bolt-to-done players are not doing it. They're simply using a GPT or anthropic model, adding a thin layer. You have to rebuild the entire experience end-to-end. Do you do that by identifying something where AI doesn't just improve the margin?”
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 buybacks and there are buybacks with a capital B. You want the capital B one. You want a CEO of a large company to do a $20, $50 million buyback to show confidence.”
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
“It's both. They are confident internally, but they need a signal to show that they are confident. I think the founder buyback is the strongest signal. It's not just the company, but also the founder.”
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 more attractive than most companies, most software companies, but if they don't build agentic workflows and commoditize a complement by figuring out where their profit pool is, I think they have to figure out, is the profit pool in the data or the workflows? If in the workflows, they need to make data storage free and basically change pricing to an outcome-based model based on workflows. If they feel the profit pool is in the data, then they need to give away these workflows for free. And so they need to really commoditize all the agentic companies that you and NO that are trying to build on top of them and charge for that. They need to build better products using their data and make it free. And I think that's the way that a net suite or a sales for the system record needs to operate. They have to commoditize a complement. They can't just wait around for other people to build on top of them.”
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
“Well, they don't have scale. Their scale means that it is cheaper for them to produce. I think they have a score of three because that's the thing. Software earlier was a scale game where because you had produced a lot of software, it was cheaper for you to produce a lot of software. Guess what? Now everybody can produce software as cheaply as anybody else. If they had their own data centers like the, I think hyperscalers are the ones that basically are able to say confidently that they have scale or people in the physical world. A pure software company can't get that scale board. But yes, they are very similar to Atlasian where they have a score of three, I would say.”
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
“Businesses are much more rational in thinking about it, less irrational, and the alternatives are going to be much stronger. I think on the consumer side, consumers are much more like dollars. And there is dollars and cents, but there is a natural inclination to just trust brands. I think on the business side, it is going to get weaker. I think I actually disagree a little bit because switching costs are so much lower. One of Hamilton-Helmer's seven powers is switching costs. I think switching costs is less going to go to essentially zero because over the next one or two years, ability to port data, your data as a business or consumer from any ecosystem to another ecosystem is going to be very easy. And then people are going to be able to replicate almost pixel by pixel the experience you have with one product in a different product. So you'll have clones popping up left, right, and center and data portability is going to be easy. In that case, what is that brand really? It's like in professional sports, do you cheer for the play?”
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 Shopify will build it. Shopify is an investor, and Shopify, I think, has decided, at least in my opinion, that Shopify has these things called missions, and I think they decide this is not part of their mission to build this product. So I don't think the risk is Shopify. It is that it has become easier to build Clavio now than it was a year ago. So it's easy to build Clavio. I haven't talked about brand. I think brand is no longer a strong word. I explicitly excluded brand. I don't know how strong Shopify's promotion of Clavio is. I think a lot of it depends on whether the propriety distribution they get from Shopify, how strong and tight it is. If Shopify is actually going to promote them as a, you know, when you search for messaging or communications, Google has a mode with Apple. When you use Apple, you're basically Apple products. You get Google search engine. If Cloudview is a preferred product and they have a relationship that makes it work, I think it's very hard to displace them. It's hard to at least displace that part of their business.”
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 agree with that. I think Atlasian has proprietary data. Now, they need to use that data to build products. They have unique proprietary data on all the code out there because it's being checked in. There's a lot of stuff they have which they need to use for better. They have a workflow mode. They don't have a regulatory mode. I don't know about distribution, what need to think of where they have something there. Ecosystem mode, I think there's a lot of third-party things that are built around them. So they at least have a score of... Not sure if they have the other modes. So you're right, Monday in theory, has a much weaker score, I guess, than Ben Atlacean on this.”
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
“Replicate. I think Amazon is a great example. TSMC in semiconductors, scale boats. So those are the eight modes, basically data, workflow, regulatory distribution, ecosystem, network, physical and scale. And so what you do, I think any one of these modes is not enough, but what you want to do is you want to stake a company and score it across them, maybe you assign one point to each mode they have. And I think anything four or more, you're pretty damn secure. But if you have a two or three, it's a weak mode. And if you have one or less, you probably need to really build some more modes or you need to do something to make up for. If you have zero, you're screwed, basically.”
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 can wipe code and e commerce hosting platform, no problem. But can you wipe code the hundreds of thousands of developers and third parties who built all these applications on Shopify? Every Shopify merchant I know uses like at least five or six other third party apps. That's a huge part of the Shopify ecosystem. That's a moat. Sixth one is a network moat. That's Classic DoorDash. I think DoorDash is many other modes, but AI can wipe code the ability to access restaurants, but it can't vipe code liquidity, career density, reputation history, all of those things. So marketplace density is a network effect, which is structural. Seventh one is the thing you mentioned, physical infrastructure, right? Atoms, wherever you have atoms, it makes for a mode that's hard to displace. You can't, again, I think humanoid robots will maybe at some point start taking, but it's probably a few years away. And the eighth one, I would say scale mode. If by virtue of your scale, your costs are so low that it's hard to.”
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 have empty else money transmission licenses state by state. They raise with the Finney CN, all of those things. It makes it impossible for a company to use anybody else than Coinbase to custody their crypto because of that reason. Fourth mode is a distribution mode where you have proprietary exclusive distribution. Intuit is a great example. Anybody who wants to build an accounting system, I remember when I started a company, this was after Google, I basically tried to use this company called Zero XERO. And I was like, let's use Zero. It's like they knew it had just started. It seems like a cooler interface. My accountant said, no, I'm sorry. I don't use zero. You shut it down. I had to cancel zero and go to QuickBooks. What a great distribution, what you've trained a network of CPAs to only on a QuickBooks. I don't know if they have a commission or what they get, but that's a proprietary distribution channel that these guys have. Very hard to displace them. Fifth one, ecosystem mode. If you have a platform or ecosystem where many third parties have built on and rely on, you have a mode. Shopify is a great example.”
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
“It's basically a play on Hamilton Helmer's seven parts, but it's slightly different. I call it the eight modes. The first mot is data mode, which we all talk about, but it truly has to be proprietary. It has to be data that nobody else has access to. I think Spotify is a good example. If you look at their Discover product, it uses a decade of listing behavior across hundreds of billions of people. You can't create that listing, that Discover product easily. Second is the workflow mode, which a lot of people argue it's a weak mode. I agree by itself. It's a weak mode, but the deeper you're embedded in the company, running their operations, moving their money, the deeper the workflow mode is just by itself. I don't think it's enough in perpetuity. But the deeper you're embedding is, for example, NetSuite is an ERP that runs your business. They have a much, much deeper mode than, say, Zendesk, which is a lighter workflow mode. So that is a mode. You can say it's one, maybe Zendesk is 0.5 Net Sweet is a 1. Third one is regulatory mode. So licenses, capital requirement, multi-year procurement contracts, Coinbase where I'm on the board is a great example.”
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
“Well, as all of our software portfolios are deep red, right? All of us have some software socks, and the reality is public market has decided that since code is becoming free at the low end and becoming much easier to generate and create at the high end, the market decided that every software company is going to zero. I think this is 100% an overreaction because not all software companies are created equal. And I actually, I mean, both you and I think about this a lot. What are the characteristics of a durable software company? And I think there is a few that we can talk about. But yeah, I think it's absolutely, I think everything has been painted with the same brush at this point. It is absolutely no reaction.”
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
“It was the most operational of all four companies. I thought I was a good operator when I got to Dodash, I really realized what operations means. And so a lot of my philosophies around how to truly operate in a hard mode have been shaped by it. It really was the epithosis or the epitome of, I think, how product and operations can work together in the physical world. So how it shaped my investing philosophy is the kinds of people that came out of DoorDash, I just think they are excellent. And I try to get them. It's really around hiring. It's around talent. It's around taking really hard problems and solving that. I'll never forget when COVID hit, as you know, most restaurants were shut down for the first couple of weeks. And so DoDash had to make a very hard call around what to do, how to get these restaurants open. And ultimately, we decided to not take any revenue share from these restaurants for a month, even though we were a private company. We had some amount of cash on the balance sheet. And that really hurt. It was the right thing to do in the”
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 power of a multi product portfolio. I think at Square, when I joined, we were a single product company, payments and payments only. When I left, we had, I think, 11 products each doing more than 50 million in revenue. And one of the interesting metrics was our key North Star metric went to median number of products used by a seller, by a merchant. Turns out that the more products that a merchant uses, the more retentive they are. The more sticky they get. So this is the other thesis I have. I mean, this is obviously very clear now. You cannot be a single product company. And most importantly, your product number two needs to emanate very naturally. It can't be like this completely separate product. It has to be very adjacent for Square. It was a product called Square Capital, which was basically a cash advanced product that really came from the fact that Square controlled the payment flows and knew exactly the merchant's credit history and could underwrite based on basically money going in and out. It was a beautiful product.”
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
“What is interesting is that even if you have a remarkable product, you still need distribution. Facebook taught me the power of distribution. Mark, I think, is the best distribution genius in the world. He would look at a product and say, this is how this product is not going to work. And it taught me the power of multiplayer products in particular. Most software products are single player. And as soon as you make the multiplayer, there is a uniqueness in switching, distribution, et cetera, that comes about. Facebook by nature, you can't use it if you only have one person on Facebook. And so when I saw Figma, the power of Figma I felt was it was not just that a person could use it, but it was much easier to share with other people in your company. And I think the best PLD software companies are those that you can use multiple can use and it increases defensibility. So the power of distribution and multiplayer products. What about?”
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 turns out it was. And it was released on, if you remember, April 1st, 2003, and that people thought it was an April Fool's show. But that was Google literally taking something that was unbelievable and making it reality. And so that's the kind of products I like, something remarkable, something unique, something powerful.”
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 the best way to think about the Google experiences, Google taught me that ultimately the best companies have a remarkable product at their core. Google was definitely a philosophy of build it remarkably and they will come. GTM was not Google specialty. But what Google was really good at was building amazing products. Sometimes the go-to-market worked, sometimes it didn't work. But at the Cor was a remarkable product. So ultimately my core investing thesis is that if there is not a remarkable product, all the go-to-marketing distribution in the world will not save you. I look for what the remarkability is in the core product or value proposition of the company. Is it 10x, 100x better than the alternative? I'll tell you a story at Google. When I joined in 2003, there was a project going on called Caribou Internally. It's like, what the hell is this? This was web email which gave one gigabyte free storage. And back then, Yahoo Mail offered 10 megabytes of storage. So it was 100x. I was like, there's no way it's...”
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
“Ecosystem mode. Sixth one is a network mode. Seventh one is the thing you mentioned, physical infrastructure, right? And the eighth one, I would say scale mode. You cannot be a single product company. I think vertical products, you've got to really own full stack. I think it's harder otherwise to be a 10 plus billion dollar 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
“The first mode is data mode. Second is the workflow mode. Third one is regulatory mode. Fourth mode is a distribution mode.”
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