20VC: General Catalyst CEO Hemant Taneja on The Future of Venture Capital: Chanel vs Walmart | Lessons Scaling GC to $40BN in AUM | Investing $5BN+ Into Stripe Over 14 Rounds | Investing Hundreds of Millions into Anthropic at $60BN Valuation

Our aspirations in venture capital is to be the best seed firm in the world. Venture capital can't scale and performance at the same time. I deeply believe that just because we have more money doesn't mean there are more Patrick Collisons, Sam Altmans that are going to go build iconic companies. I lost a Series A of Stripe. I lost a Series A of Samsara. I lost a Series A of Snap. Triple, triple, double, Double is definitely dead. Going from 1 to 3 to 9 to 27 is not interesting. Or 1 to 5 to 9 to 27 is not. Whatever. The math is not interesting. You got to go like 1 to 15 to 20 to 100.

You are listening to 20 VC with me, Harry Stebbings now. I'm so excited for the show today. Today we welcome Hemant Taneja, CEO and leader of General Catalyst Now. Hemant has scaled GC over the last decade into one of the largest platforms in venture with over 40 billion in assets under management. He's also been one of the most influential investors leading early investments in Stripe, Snap, Gusto, Samsara, Grammarly and Canva to name a few. He also incredible role in Livongo's 18 and a half billion dollar merger with Teladoc, one of the largest digital health deals in history. This show is incredibly wide ranging with everything from the future of labor to geopolitics to the future of venture capital. I loved doing this show. Hemon was so open and it was just fantastic. You can check it out on YouTube by searching for 20VC and I cannot wait to hear your thoughts. But before we dive into the show today, I love seeing the team come together to make this show happen. What I don't love is trying to keep track of all the information, the data and the projects that we're working on across dozens of platforms, products and tools. That's why we use Coda, the all in one collaborative workspace that's helped 50,000 teams all over the world get on the same page. Offering the flexibility of docs with the structure of spreadsheets, Coda facilitates deeper teamwork and quicker creativity. And their turnkey AI solution. The intelligence of Coda Brain is a game changer. Powered by Grammarly, Coda is entering a new phase of innovation and expansion, aiming to redefine productivity for the AI era. Whether you're a startup looking to organize the chaos while staying nimble, or an enterprise organization looking for better alignment, Coda matches your working style. Its seamless workspace connects to hundreds of your favorite tools including Salesforce, Jira, Asana, and Figma helping your teams transform their rituals and do more faster. Head over to Coda iO20VC right now and get six months off the team plan for startups for free. That's Codacoda iO20VC and get six months off the team plan for free. Coda iO20VC and while Coda keeps your team aligned, Radix makes sure your startup's name is just as sharp. This one's for all you tech founders out there. You've finally come up with the perfect name for your startup. Then you check the.com and damn, it's taken, parked, unused or priced like rent in Palo Alto. So you settle with extra letters, weird spellings, whatever it takes. But hey, you don't have to compromise because now there's finally a domain for tech founders like you. Tech domains get the startup name you actually want on tech. No compromises. What's more, when you use tech, you signal to your customers and investors that you're building tech with just your domain name. Isn't that cool? So if you've got a name in mind, search for it. Now with tech on a trusted platform like GoDaddy or Visit, get Tech20VC to grab it. You've got the name locked down with Radix. Now it's time to get the fund structure just as solid. If you're listening to 20 VC, you know we have a really freaking high bar. Well, Angellist is the modern platform used by the best in class venture funds where over 40% of top endowments and banks are LPs. Their customers include a top five venture firm, 20VC and they now have, check this out, $171 billion of assets on the platform. They combine an all in one software platform with a dedicated service team that moves as fast as you do. One manager said this awesome quote, angellist feels like an extension of my fund. Another said Angellist gives me total peace of mind. The attention to detail, lightning fast response time and just real sense of ownership from the team are exactly what I need to stop worrying about back office ops. So if you're starting a new fund, don't be a moron. Just use Angellist. They're incredible. Head over to angellist.com 20vc to learn more. You have now arrived at your destination. Hemant, it is so good to have you here.

Last time it was seven years ago. It wasn't in person. I've been so looking forward to this.

Dude, it has been seven years. Last time I was younger and you were a little skinnier. You've gotten Fit. And you have no glasses. And I have my glasses right here.

Dude.

I was much skinnier.

I think this was before I fell into a.

You're doing well. It's good.

My. My question to you is, you have built now in the last 10 years, one of the most defining firms that we have in venture. Do you consider yourself a venture capitalist or do you consider yourself a CEO?

Harry? That's a great question. I carry the title of CEO and managing director for a very intentional reason, which is General Catalyst is a business, but it wouldn't be a business if it wasn't venture capital at its core. I am a managing director and a partner just like everybody else in our partnership, but I'm also a CEO and that's the duality that it's going to take to build an iconic institution in our industry.

Do you think GC is still a VC firm?

GC is very much at the core of VC firm. Not only that. I mean, our aspiration is that we want to be one of the best seed firms like you. That truly is our aspiration because the earliest relationship with founders and that trust is the key to actually doing the best work in building the companies that matter.

When you look at Total aum, can you realistically put the hours in and justify that commitment to ZEED when it's a $200 million vehicle in a $25 billion pool?

Culturally, this gets hard for VC firms as they scale. At GC, the thing we talk about is focus on the ownership and the relationship with the company versus the sizes of check that you put in. And when you reorient yourself to think that way, we get that only at seed. If you think about the last two years, bringing on Jeanette and La Familia, Yuri and Wayfinder and Neeraj and Venture highway, we've tried to really make sure at our core we remain very committed to doing the seed work with the same intensity and rigor that you do at 20 BC.

Oh, zero rigor here. Oh, no. We're just like blindfolded throwing dots.

I didn't say a lot of good. I said the same rigor.

Okay, fantastic. I was feeling bad for a minute.

It really like it's a genuine comment. Like we internally talk about early stage venture capital as a core and obviously we want to leverage that core to have greater impact in the world. But if we don't do early stage investing well, we will lose the right to exist and we're paranoid about that.

Do you worry about the transition of venture? Douglione said that we've moved from a high margin boutique community to a low margin commoditized industry. Do you agree with that?

If you think about the innovation in venture as the role of technology has scaled, all the innovation for the most part ends up being on the three axes, state, sector and geography. Make the funds bigger, put them in different geos, put them in different sectors. Well, the reality is that role of the companies that we're building is becoming far, far more sophisticated in society. The innovation in industry was much more focused on how do we deploy more dollars and try to keep as much of the return as possible where the reality should be, how do we retool our proposition for founders so they can build the biggest companies possible. So when you think with that second lens, you have to innovate and you have to think broader than just that sort of fund formation mindset. That is what allows you to break from hey, going from high margin boutique. So smaller funds better returns to low margin scale, which is bigger funds lower returns. That's only happening because we're thinking about innovation in a constrained way in this industry versus being first principled about how do we transform our proposition for founders.

You said that kind of bigger funds, lower returns. Do you disagree with that as a premise then?

No. I actually have a strong belief that venture capital can't scale and performance at the same time. I deeply believe that. And the reason is because just because we have more money doesn't mean they're more on Patrick Collison's or pick your favorite founder Sam Altman's that are going to go build iconic companies. So we're actually in some ways finding the zero sum game of founders that are naturally going and doing great things. So that's not necessarily going to scale because we have more money, but if we can create more tools to have more founders to scale, then we can actually manufacture more outliers than the ones that naturally exist on the Power law. Our mindset is how do we actually expand the proposition to founders so that they can be more companies on the power Law? That is a very different way to think about it than do we have enough capital to get everything that's on.

The Power Law if you accept lower performance with bigger funds? Respectfully, Hemant, what do you tell LPs when you go out and fundraise for early stage venture funds and much larger funds? Is it just a different LP class? Because I'm sure you hear the podcast and the shows and it's like oh well, they're just pitching sovereigns who just are happy with 10%. And so it's graduating.

Going back to saying that we want to remain early stage venture at our core, I actually reject being in a business that has lower performance. So what we have done is, if you look at our overall assets under management, we've basically said we're not going to make our venture funds bigger. What we're going to do is actually keep the size of the venture fund where we think it can be to create elite performance, which to us is you got to at least deliver 4 to 5x funds on the capital that you raise and sort of build bottom up. Can you do that in venture? And then we have creation and customer value fund, which are focused on other value propositions, other capital solutions for founders so they can do M and A more effectively. They can invest in sales and marketing more effectively, but don't scale the venture fund itself because that'll degrade performance. That is the way we have architected our capital that we provide to founders.

When you think about where you intersect with them in the journey, as much as I love the hey, we absolutely want to be focused on seed and build that relationship as early as possible. When you have the capital supply that you have today, arguably it's a much better proposition to just do a kleiner and put 100 million into anthropic at $183 billion and play the large check at Stage and actually ride that wave.

I don't think so.

You don't think so?

I mean, look, our best returns have come from seeding companies like Stripe and Anduril or creating companies like Kayak, Livongo and Khmer and others.

Livongo is insane, huh?

It was. It was a great outcome for us. And, you know, that's something we built in our offices.

How much did GC make from Livongo?

A few billion.

How big was the fund?

So luongo sat in two funds. It turned one of the funds approximately 3 or 4x and it returned one of the other funds maybe close to 1x.

Is that the best performing investment GC have made?

I think you would have to give that to Stripe still. We've been invested in stripe since 2010. That's a big position for us. My point more is, for us, we obsess over either that the companies are getting incubated at GC or we're investing in the seed round. If we don't, we want to be in the iconic companies, we will invest in them at Growth stage as well. And that to me is about believing in the companies that you think will compound for a long time. Like take Stripe as an example. We invested in 2010 and I've invested in Stripe 14 times in the last 15 years. Just to give you a sense. Okay, that's one of our core philosophies, that when you think something's going to be compounding for a long time, be strong sort of supporters of the company along the way. We invested in housing. Jeanette has seeded that, if you remember before, and we've invested that in all the rounds that they raised since. Since then. If you look at Anduril, same thing, we seeded that and we invested in every round that they've raised since then. So I think being part of these iconic companies and supporting them along the way is the reason to have the capital base. If we miss them at Seed, we want to catch them as early as possible and then continue to help them with everything we got. Our entire proposition as a platform to support these founders and help them all the way to endurance.

Can I ask, when you're at your scale, do you map out the industries that matter, the companies in them and go, we have to have a check in these regardless of entry. Is that how you kind of map markets and capital injection?

The business for me is about getting serendipity and intentionality. Right. So you definitely won't know the industries that will become important in the future. I'll never forget one of my big misses when Paul Graham asked me to look at the Seed round of Coinbase and I said to myself, a bitcoin atm, what is that? Had no idea what this industry was about to become. It still haunts me at the seed being very much focused on just backing the great founders and not over intextualizing what the returns are. And this is really culturally what.

Did you meet with Brian?

Yeah.

Did you think he was amazing?

He is amazing.

So it was purely the idea that you could.

My little brain got ahead of sort of thinking about the world. And so my point was you definitely want to add the seed, not be industry focused. To say we're going to back founders regardless of our view of the world, then I think the reality is if you take a step back in the world and you think about the tectonic shifts that are happening. The theme that we call global resilience, where every region is focusing on defense, energy, industrials, health, financial services, how to be resilient from a sovereign perspective, that does have impact on industries, that does have impact on how business is going to get built. So we do look at it saying Are we in the right companies in the context of how the world is reshifting in the context of industries? So as an example, I'll tell you, I think we're the only firm that's invested in a defense prime in US, Europe and India. We did Anduril, we invested in Helsing, and we invested in a company called Rafi in India. Well, each of these regions needs to create its own AI deterrent solutions and they want to see indigenous industries emerge from a resilience perspective. So we should make sure we're backing that theme. So I think it ends up being embrace serendipity, be humble that these founders are going to take us in the world in a way that we just don't understand and then be intentional where we think there are large macro shifts happening so that we can play certain sectors with a bit more of a thematic lens.

What do you think is the most significant macro shift today that not enough people are talking about?

The most significant macro shift today that not enough people are talking about is thinking about jobs. I have gone around the world. We have a real focus on understanding how to help governments think about transformations and the transformation of any country we think is in four parts. One is how do you apply AI to deterrence? Because without peace you don't have capitalism. And if there's no capitalism, then business can't really be a change vector. So you need peace. You think about transforming healthcare because we just came out of a pandemic and we saw what it can do and we're still reeling from it. You need to accelerate diffusion of AI into business because that's ultimately what's going to lead to your industries being competitive. And then if you get all that right, you have to think about jobs because there is immense reskilling that needs to happen. People are starting to give lip service to it, but it hasn't hit people yet. We were talking about this earlier. We have a lot of these AI transformations we're doing of these service businesses, these AI rollups, as they're called. And I'm seeing this, I'm seeing what's going to happen to jobs as AI gets adopted to bring efficiency and productivity to these white collar jobs all around the world.

What are you seeing there?

Because the MIT study was discouraging. It's like 95% actually doesn't actually have much impact. And I read and I'm like, God, this is a bit of a downer. So what are you seeing?

Okay, I do think there is merit to the MIT study for the following reason, when you think about transforming an enterprise with AI, you actually have to do four things correctly. First is you have to get your data infrastructure ready so that your company can adopt AI. Your data readiness is huge. Infrastructure readiness is huge. Second is you need models that understand your business. You have to train these models in the context of your secret sauce, your business. Third is you have to think about a workforce transformation. Because now you're going to have humans and you're going to have AI working next to each other. Some humans are going to manage AI agents, some AI agents are going to manage humans. Imagine how the org charts have to change. And the fourth, for all this to work, you actually need courage at the top. The CEOs need to really get behind it, to drive it. So the idea that all four of these things are happening in a company to make the adoption of AI go from beyond just prototyping OpenAI or an anthropic model to really creating change in your business is very difficult. That's why these things are hitting a wall. But that's why this MIT study is giving you the signal that it's giving you one place where businesses already outsourced and let go of core operations was wherever they wanted to get labor arbitrage over the last 40 years. So our whole thesis around AI roll ups was everywhere. You offshored for labor benefit. You're going to onshore for AI productivity. That's where we're seeing a lot of this. So we've bought call centers. I'll give you an example. We bought a call center in Philippines, 3,000 employees in one of our companies called Crescendo. It's going to have a huge change in this headcount. It's going to go on by quite a bit as this fully gets AI enabled. My first question to the team was, well, what are those people going to do in Philipp Philippines and how many are there? So every country that built their middle class off of offshore labor, how do we really help them think about reskilling those people to be more successful in the world of AI? This is what's not being talked about enough.

Do you think this is a 12 or an 18 month problem or actually a 5 to 10 year problem? I always go back to the Bill gates. We overestimate a year, underestimate 10.

Is this adoption of AI into businesses going to be fast over 12 to 18 months or 5 to 10 years? I would say this is a five year problem. And I say that because if you go back and think about the physics with which these companies are getting built. The companies were building. You have to put these teams together. They have to go get some customers they can demonstrate progress on. Then they have to start accelerating growth. Only after a few years of that do you start to make a dent in the industry enough that it becomes a problem. And so just a diffusion of technology has its own physics, so it's not immediate. But five years is also not a long time. And so what I'm seeing is that these companies, enough of them, are going to start being successful in these different areas and they're going to start impacting jobs in a material way. I'll give you a really interesting anecdote that the CEO with the large consulting companies told me. One of their big clients came to them and said, we have 50,000 employees today. Draw up a plan for us that in five years we are 100,000 employees. While only 10,000 of them are humans, the rest are AI agents. This is to be provocative, but they're sort of saying, if that was going to be our plan, how do we get there? This is the kind of stuff people are thinking about now. It's not going to happen in the next five years. But that are organizations going to potentially change that much over the next 10 to 15 years? It's a non trivial probability that can happen.

That's a very forward thinking CEO and business leader. To what extent are governments prepared, thinking and equipped for this labor change that could be there within a five year period?

I think not enough. I think people are still grappling with what does AI really mean, how fast is it going to diffuse. They're not even thinking enough about reskilling. But I'll leave you with one interesting thought on this particular topic. We're in London today, okay? Imagine if every nurse and every lawyer and every accountant that works in London becomes an AI agent of some company in the United States in the next 10 years. You're going to hollow out a lot of your labor productivity and give it to a US company or a Chinese company. My point is more about it could actually hollow out the service sector, just like we hollowed out manufacturing jobs for globalization before getting every region to think about this. This is actually a point that Jeanette makes with her European Champions initiative a lot, which is how do you retain productivity onshore in these countries so that while you do the AI transformation, you're maintaining vibrancy not only because your business has got more profitable, but also because you're capturing the productivity gains onshore as well. The governments need to think about this as they are architecting this sort of next phase of their transformation with AI.

Which government do you think is most impressive and which is most screwed?

I find folks in Singapore to be very impressive. I recently went there and I spoke at their National Singapore Day and I was just blown away by the depth of thought that the politicians there have done. I have to tell you, Prime Minister, Greece is very impressive. He's thinking about how do we really be pragmatic in deploying this. I've met with Prime Minister Starmer here. I know there is some announcements being happening this week as well around AI, So I know they're making some moves, but I don't know, I don't see enough of that. Hey, let's think comprehensively about this. The answer I usually get when I talk to heads of states about diffusion of AI and this jobs issue that we just talked about is they have belief that if it's going to be that disruptive that society will just slow it down. You just can't have a world where I know in Silicon Valley we covered a billion dollar employee with a company with a single employee, but you just can't have a world where that's what business looks like and people have no work. And so at some point the interplay of business and society will sort of force it to be a more stable scenario. That's what the governments are thinking for.

I think that's true.

I think Adam Smith's invisible hand would tell you otherwise.

I think market forces are way stronger than that. I agree with you, but I think that's a little bit of what they take comfort in, is that we have time to figure this out. And I don't think we have time unless we're a lot more intentional about it.

I vehemently dislike government intervention. I'm as free market maximalist as possible. Is that the same for you?

I think you can't make progress if capitalism is not working. But I do think capitalism is a privilege. If you think about what happened in the last 15, 20 years, a lot of the nationalism all around the world is because social media essentially struck a chord with the core issue that all the technology productivity didn't really get passed on properly to everybody in society. It created multiple multi trillion dollar companies. But our own innovation ecosystem, how much did that capture and how much does society really capture? Actually a small percentage. We look back and say, wow, venture capital, there's been a real boon in the last 15 years. But when you look at the overall value created in venture compared to the max 7 it's noise. And so are you really creating a world where there's opportunity and capitalism can kind of do its thing? You have to make sure you protect that. That part of it. I do think government has played a role in. Beyond that, you got to be very free markets oriented. Let bottoms up innovation stuff that you and I do, let it go. Create the future. I mean, that's what you want to see.

Do you worry about the ever increasing inequality of plays in our favor? In a lot of ways, but I look at so much of the next 10 years and I just see the concentration of wealth to very small networks and I get very worried.

I am worried about that. The whole idea of can we build these companies that can focus on being the most profitable, the biggest, but also in a way that they're inclusive. That's something that I think a lot about. There's this moment, if you think about the last five years, we've had wars, we had a pandemic, we had a situation where because of wars, we actually us kicked Russia out of swift. So financial infrastructure got questioned. Every part of our energy crisis happened, Every part of our core pillars of society where capitalism maybe is starting to break. All sort of manifested over the last few years. And then AI comes along as an answer to all this. So now the choice we have to make is are we going to build these business in a way that the value accrues to very, very few, or can we actually do it with a mindset of abundance where everybody benefits? And that's a choice that we have in the way we set up the companies of the future. And I do worry that if it's not a mindset of abundance, then that's not sustainable in the very long term. We won't feel that in the next 10 years and you and I will make a lot of money. Our funds will do great and our partners will generate great returns, but what do we create on the other side? And I think that's the thing that we have to think hard about.

Is it actually a choice though? If we think about say your OpenAI's or your anthropic. I know you're an investor in anthropic. When we think about the value that they generate, those returns will go to a very small handful of people. Is it at choice that we're concentrating the returns and wealth?

I think about innovation in AI in two parts. One is every region is trying to figure out how to become leaders in core infrastructure and we're racing to it. And there's not going to be many, but there weren't that many clouds. There's not going to be that many AI model companies that actually become at scale and potentially be even bigger than what these cloud companies became. I think that's current course in speed. That's probably what's going to happen. But what happens on top of what's the ecosystem we're building and how it interplays with consumers across the board? What happens to healthcare, what happens to education? How are we thinking about those things? Is there a level playing field so there can be a vibrant, diverse ecosystem that gets built on top? That's what I think a lot about. So, for example, is the Amazon of healthcare going to be an ecosystem, lots of companies and sort of a more resilient system, or it's going to be like some company that comes along and that just controls healthcare? The latter is not good for us. And so how do we create a level playing field for startups, for founders, so that opportunity can manifest into new successful businesses everywhere versus it's going to be a few concentrated ones? I think that to me is the place where policy has to create conditions, where it allows for opportunity for many as opposed to opportunity for a few. That's the role governments can play when it comes to technology.

I've been very public on my concerns around the labor government in the UK and what it's done for the UK so far. It's the fastest exodus of millionaires out of any country. It's terrifying. Are you more bullish on the future of the States with the Trump administration or not?

My belief is that U.S. is very well positioned. We have energy, we have AI, we have the largest market, we have the largest entrepreneurial ecosystem. In a lot of ways, we're very well positioned. And I think in the short term, in some ways we're actually increasing our moats. If we really focus on everyone investing in the US and creating more capital and whatnot. When we fund companies, whether it's in Europe or in US I always think about it as, hey, you need to go win your market and then you need to become a global leader. And the thing I worry about in the US today is mostly what is the sentiment and the appetite of the world to embrace companies coming out of the US and let them be global leaders. And I think that's where there's going to be work to do because we're doing this one time reshift with tariffs and everything on, hey, we need to realign commerce and trade. But we were also the keeper of the world order in a lot of ways. And as we are disrupting that, what is the relationship going to be with European countries? And how well positioned would the American companies be to be global leaders? That's the place where I think rubber meets the road in our ecosystem. We're talking about sort of companies funded in our world founders. How will they become global leaders? Given that there'll be more friction? That to me is the place where there'll be some challenges.

When you walk around London now, as I do with my mother, every weekend, all we see is Andriel posters on the sides of buses and on the.

Sides of bus stops.

I always send it to Matt Grimm, like, thank you for decorating London with American posters, which actually look incredibly British and wonderful.

By the way, I love your post with your mom. I think that's a great thing that you do every weekend. I enjoyed your last post about breaking the idea of 90% of your time you spend with your parents is before 18. That was an amazing, insightful comment.

I find it incredible that people just accept that you could change that. I really appreciate that. But when we go to that, when people become global leaders, the element that's inserted is competition. Because when you back multiple geographic leaders, suddenly Anduril comes into Helsing's path. It's the age of not having competitive investments over. And when you're at your scale, do you just have to embrace that you're going to be in multiple players in the same space?

Look, I think when we invest in these companies, we always want to see that they will be the leaders in their own market. We have a lot of confidence. Helsing with its mission, its execution, its access to capital, talent should be the company that gets disproportionate share of defense in Europe. Europe Anduril is doing that in us. We think this company Rafi is going to do that in India that we invested in. And then they should go and be competitive in the global ecosystem also. I actually think maybe there's a new innovation in partnerships. We have not innovated partnerships ever. It's sort of the same boring old metaphors. And the question is, could these companies all think about engaging? It's not what's happening yet, but are there these resilient ecosystems that get created where they have special advantages because of where they sit in which ecosystems and they can leverage each other to gain more global share as well? So I'm sort of very keen to see while on one side we've created some structured inflation because of the need for global resilience. On the other side, I am curious is the playbook going to change and how you become market leaders in this next phase?

You mentioned kind of on the GEO side it's like it's race for infrastructure and I find there's this often rhetoric that's like hey, it's China versus the US and it's the war for AI. Do you agree with that? Race for AI? Is there a destination, is there a winner? What does that mean?

The way we see it, we are in a bipolar world for sure. Despite all the recent turbulences around tariffs and relationship between the different regions. Us, Europe, India, very aligned in terms of core values and I do think it's going to settle down to be a place where AI gets developed with a common set of values. I think the Chinese system is different and the race to me is only in the context of which AI is better because capitalism will force the adoption of that. Think about Deep Seek and the open source models that have come about out of China. People are using them in the US because they're better. Now the question is which AI ends up and there's not much difference between I think China and US are very comparable in what they are in AI today. There's a few months lead here and there. I'd even argue there's always a second mover advantage to people building on top. So I think they're pretty comparable. It is important that you see AI infrastructure in the west gain market share in businesses and be more pervasive. It's equally important to make sure it's done in a way that the compute productivity is captured onshore in each of the geos so it doesn't leak from a lot of the places to sort of a single company or a single country because that creates imbalance. You want to be inclusive and abundant in your mindset with AI creation. But is the competitive dynamic something we need to worry about in terms of companies coming out of US versus China? Yeah, that's driving a lot of where the value is going to be our.

Ability to compete globally in terms of second mover advantage. Really interesting element. Do you primarily believe that just because of distillation and the benefits that we saw Deepseek have as a result of.

Being second, you're seeing this in different use cases. Take customer support for example when new models come out. If you started building your company when you were in the ChatGPT3 era versus 4 versus 5, you just have more tools at your disposal. So the go to market advantage you may have created in a year. Having started on GPT 4 versus 5 might be anemic compared to the technology advantage that you have if you start in the GPT5 or the choices you make and how fast you can move because the models are stronger. Because it's like you're getting this put in force unfair advantage. And are you really going to sort of re architect everything you did and take a step back or not? Because you actually have good momentum. So what's happening is that the good and greater companies getting created with each new model and the model companies that start later end up having some advantages because of technology. And the question is, can you not be bogged down by technical debt? Even though technical debt used to be on the order of a decade of coding, not a year of coding, can you actually overcome that and make sure you remain well positioned on the new sort of technology stacks or not? That's the advantage that I think second mover companies could theoretically have in these different verticals.

You mentioned kind of the evolution of models there from phase to phase. Anthropic is a big position for you. Can you talk to me about your first entry point into the company and the thesis that you had on first entry?

Look, we invested in the topic only less than a year ago at the $60 billion round where we saw that the use case around coding was becoming an interesting application that was going to distinguish them. These models started to become distinguished. Obviously everybody wants to do everything, but OpenAI to me is more of a consumer company with ChatGPT. I know they have enterprise ambitions, codecs, et cetera. I get it. And Anthropic kind of of became an apps company in the cloud world with coding as a use case. And we're showing really good traction. That was a time, for the first time we felt, are we really betting on these companies with tremendous valuations, tremendous burns, tremendous dilution towards some abstract AGI goal or they're actually going to be businesses? So I actually think risk adjusted. That was the round that was interesting to do as somebody who studies investment decisions and companies say where do people get lucky and where do they actually, actually make a great call?

Why do you think that was the round that was the best?

Because that's when the use case that was going to draw them in and build a relationship with the enterprises became very clear and could scale. And it has. When we invested, what was that revenue? It was at the end of last year, so it was, I think it was under a billion if I recall. And they publicly said they're going to grow nine times that. That's not the forecast we modeled. I mean they've done way better than we thought which is amazing. It's an incredible team. Very values oriented, very execution focused.

How much do you put in at 60?

We put in a few hundred million.

Few hundred million and then you do another few hundred million at 180.

I think you would by the way I would actually argue with 5x over subscribed anthropic. This round probably was the cheapest round that got done this year on a multiples basis which company was raising capital at 20 times? ARR. They're all raising capital at 50 to 100 times arrangement at a scale that's like 10 times bigger than any of those companies that are raising capital. So like risk adjusted if you think about it and I should say risk adjusted carefully because durability of everything in the models is highly unclear. So in that cohort I would say that was the best price round you could have done. I'm not surprised it was 5x oversubscribed dude.

Risk adjusted. Fuck it. That went out of the window years ago. Welcome to Venture.

I eat risk for breakfast.

Along with that is the caption for it. When you look then out do you put another few hundred million dollars into the next round?

Depends on how the business does it. Depends on how they're expanding. But when you get into growth you have to be very fundamentally focused on actual economics. Revenues, margins, profitability scale. This market size for these things is endless. $500 billion payroll is developers in the world probably I think about 10 trillion of white collar jobs if I have that generally correct. It's an insanely large market and you're naturally well positioned to be one or of two or three players that's going to go capture it. So if you believe that this company could be 10 to 20 times bigger from here and it's well priced even at this valuation if it keeps on that trajectory of course you would want to invest. Who would not want to invest?

Yes.

But you also then look at the information did this incredible chart. I don't know if you saw this pie chart yesterday with OpenAI's distributions or kind of with the value generated and 1% I think it's like 5 billion is to early investors. And you look at that and I thought my word, well done Founders and team. This is the greatest transfer of wealth from venture capitalists to founders and team members. When you look at the employee stock based comp that's going out now, this is the greatest transfer of wealth ever. Is it actually a great investment when you look at the dilutive nature and cash burn of these businesses?

Well, I think OpenAI I saw that early round. Sam's a force of nature and I've said this publicly. I mean, the guy can bend reality and he has. It's changed the world. I just couldn't get my arms around the structure if those numbers are correct. I don't know if they're entirely correct. You would say at 5 billion. The $200 million at the billion dollar round only generated 25x. Our best companies like Livongo and Circle and others, Stripe and others. Our first rounds were not 25x. They were hundreds of X in terms of return. So I agree with you. Dilution took a huge toll here, but for two reasons. One is because that structure led to hey, nonprofit needs to be given a share. And the second is the compute that was needed to make this happen. The first one to provide that compute was Microsoft and they had a lot of leverage. That was a good deal for Microsoft. They made a huge amount of return because without that, this was also there was never going to be a company. So I think it's just the sequencing of who really took the risk. Sort of risk adjusted with capital. Microsoft maybe took more risk in a lot of ways and they did benefit. And then they were. So the dilution comes from a lot of that dynamic as well.

How do you analyze that relationship with Microsoft? Because speaking of anthropic, Microsoft has now openly said for the majority of suite they're using anthropic. How do you analyze that relationship?

Well, I think that relationship was, if you remember when that was done, everybody says satya is brilliant. That was an incredible way to essentially buy innovation. It's like what biotechs do, right? And pharma companies do. Bought innovation in AI because the internal efforts maybe weren't as productive and gave them the halo effect to be the leading AI company, gave them an entry with Azure. Azure's had a huge draft because of OpenAI as well, and they have really gained market share in the cloud industry as a result. That was an amazing investment for Microsoft. Microsoft, is that an enduring investment? No. Obviously now they've gone at odds with each other because there's an ambition that collides between the two companies. And so they want to have more choice. They want to have anthropic at the table as well. That's just normal good business thinking. I get it. Taking that bet was hugely valuable for Microsoft. And if you look at the return by the way, if they put in 20 billion, they're the ones who have the highest multiple return as well. So it was a great investment on a financial basis and way more on a strategic basis.

As an anthropic holder, do you worry when you see Sam talk about we're going to need to spend hundreds of billions and then you see his deal with Oracle where both of them are going to need to be levered up to the hills to be able to finance it on both of their sides.

Look, never bet against Sam, but I feel like he's doing a lot of things and he's doing it in every single dimension, right? The phone, the data center, the infrastructure and all that. I think Anthropic is a much more focused kind of a product oriented company. They have not taken as much money to get here to this size as well. I think their enterprise business, I'd argue will be bigger than OpenAI if it already isn't. Already capital is a lever, but it's not the only lever. I think execution matters and one of the things I've learned and Arthur at Mistral really taught us about this, which is you can waste a lot of compute too. So I think a more focused team with a focused agenda, you can probably get there much more effectively. And I think Anthropic seems to be doing that, being very targeted in the best they're picking and doing them really, really well. I'm a big believer that that leadership is really maturing to be excellent company builders. I mean, Dario, just think person a few years ago is running research and the kinds of choices he's made and the kinds of choices both in business and for society and how they've scaled and the bets they've made and how well they've paid off every step of the way. The thing, the products they've launched, it's like really impressive. And that's why the investors there will probably end up doing on a multiple basis better than again in the world of what's durable, what's not. They're trending to be. Maybe they'll do better in their MOI than the early investors would in OpenAI, if that math is correct, the one that you were referring to.

The hard thing is that growth is great until it's not great and at some point it does reduce and reduce and 1 billion goes to 9 billion, which is insane. I mean nuts, nuts numbers we've never seen. And what is it next year? 27, which would be 3x, which would be great still. But at some point growth does reduce. And then there's the core business that sits beneath it. The thing that I worry about is our ecosystem today is so.

But Harry can just interrupt for a second. Let's say it's 27. I don't know what the numbers they have shared and they've always better than they've said by the way too. But let's say it's 27.

You're not also anthropic CFO. Not a spoiler alert.

I got a caution. But if you think about it, that business which would still grow 200% to go from let's say 9's number this year in 27, that's tremendous growth. And you put any multiple on that, that is a very valuable company. Think about tech technology multiples on that kind of a growth. That's a really valuable company. Significant headroom because the market size is so large even from there that they can maintain good growth. Doesn't have to be this crazy growth. But they only price it at 20 times this year's ARR. So 20. 20 times 27 if you.

20 times 27 if you take the.

Same multiple which you could get in public markets with 550, something like that. My point is that so that's half a trillion dollar company like by the end of next year. I'm not saying that's what it's going to be. But if they hit their numbers I don't see why that won't happen. Just I'm just saying public market comps, that's what those things are going to be valued.

I completely agree. Does margin not matter anymore?

Today margin matters absolutely. And I actually think that's another place where they've done a good job. The reality is that when you think about the ROI in the coding space, you're doing the work. Coding agent is essentially a replacement of engineering. Right. You start with low end sort of engine junior engineers to more senior engineers. Even a junior engineer makes 80 to 100 grand a year. So your pricing power there is actually pretty significant. And if you're truly doing that kind of work, margins are not going to be an issue. And margins already are not an issue for anthropic. They have a good command. They've been very disciplined about how they built their business.

Do you worry about the competitive nature of the landscape when you look across at Codex but then you've also got your cognitions and then you've also got your cursors and you've got your kind of on the lower more consumer and your lovables Your rat plats.

Great. I'll take you back to the clouds. You could use the same logic in the clouds to be like, hey, they're going to get commoditized. You'll have probably three big telcos in every geo. There are probably three big clouds, probably three big AI models. And I'm just searching of empirically saying that. Think about the margins that the cloud companies have. It's like 70s. I do think these companies will all figure out the margin structure really well and at scale because there's so many different ways they can add value to hold onto that margin. And they're all kind of getting specialized into like different areas where they are going to be doing that.

There are. But there's only three cloud providers. Really.

Yeah.

And when we look at the plethora now that we have in terms of today.

Today. But I think that's going to shrink. I don't think everybody's going to make it. And then.

So you think it's going to be a real shrinkage in those products.

I think you'll have a couple of global ones and a couple of software sovereign ones in every geo. That probably is what'll end up sort of happening in AI in my view. Not everybody's going to make it. You have a lot of other models that have been funded, different approaches as well. We'll see what happens to those. Is there like a new architecture that emerges? But it's not going to be that many. But think about the size of the market you're talking about. The labor market is the AI market.

So you buy that massive sun, hey, there's a $10 trillion labor debt GDP up for grabs. And if we capture 2 trillion of that, game on.

I don't see why not. I don't see why technology is not going to do most of that work we do in companies better than humans do. Which going back to your earlier point, market forces will take us there. Then it'll be cheaper, it'll be faster, it'll be better and it'll give the businesses more leverage. So I think that's a real trend we're going to head down.

The path of the economy is so on the AI hype wave, or not hype wave, but like AI momentum wave. Because a lot of it's not hype. And when you look at the concentration of shareholder value accumulation and it's just solely predicated on Max 7 pretty much at this point, do you worry that we hit a speed bump and when we hit a speed bump in the AI train I mean literally the world kind of crashes, given how much is predicated on that. Or do you think that just won't happen because we are on such an exponential upswing?

I don't think it's going to be that. It's a speed bump that spirals us down. So for the simple reason that with every new model with its capabilities, there's a certain amount of that content of white collar jobs, the 10 trillion that you mentioned, that is now doable. And the speed bump's not going to irreverse that. So I think I have this sort of visual in my mind where we're kind of cumulatively taking more and more of the labor content and AI is better than us and more and more of it. And over time it's going to be most of it. And when robotics comes, it'll be all of it. And so in that context, a lot can be already done. We have the energy, we have the compute to be able to support that. The question is the really frontier stuff, what are we going to do with that? And I think you could see speed bumps there. The speed bump could be that the arc architecture doesn't scale and you need these world models to take on or some of the new architectures people are developing that are non language oriented that could maybe would be needed. So I think the frontier could slow. But I don't think this transition of labor or melting of labor into productivity is necessarily going to slow because the economics are way too compelling for that to not happen in my view.

You mentioned geo winners in some respects. You mentioned Mistrala. I love Arthur, I think the world of him. I'm obviously a proud European. A lot of people are going to, huh. It feels like they've been left behind. According to Spade A spade. Do you think sovereignty is enough of a reason for Mistral to be a winner?

It's a great question. So Jeanette's on the board there and we talk a lot about it. We've had many conversations and meals with Arthur about this as well. I look at that company and I see Arthur's growth from a scientist to a CEO. And remember, it's a two year old company.

Do you want to hear a funny story? I got introduced to him by Jean Charles at Alain and I was the first VC he ever met. And he took a video call with me on a park bench in Paris and I said, dude, I'm going to give it to you straight. I've never had such a bad pitch. And you are competing against Sam Altman, the mother of all fundraisers. This is not going to end well. And now I see him pitching and I'm like, well fuck, he changed.

He changed. But I think this is the point. Not only in his ability to aggregate capital, he stayed focused on doing really disciplined work in the way to build models. And I think they were compute constraint and capital constraints so they felt behind, but I think they've caught up. Everything I hear now is that their models are now again sort of there as they're investing. He's figured out how to aggregate capital. I mean you saw that he's also figured out that his relationship with customers needs to be a lot more commercial than if you build it, they will come. And so I am bullish on what they will do, even though I was anxious about it because he and his team are growing up. I think they're learning how to be in this competitive world. And by the way, if there were two companies not existing in this world World OpenAI and Anthropic, you said this is the hottest startup in the world in terms of how fast they're scaling and what they've accomplished and their valuation and progress. It's just you have the overhang of these two monsters that the flywheel going with capital end products and so on. And that's why we say is this interesting. I actually think they'll build a pretty compelling business. I see a lot of interest from companies in Europe, but all over the world that want an open source player. Like who else is truly dedicated to open source? That is doing it in a way that enterprises can year. It's not meta, they're not an enterprise company in the West. It's really Mistral today.

Can you name to me success stories where sovereignty was the number one driver of their success?

All the US defense primes were built off of sovereignty. We were the biggest allocator of spend and defense. And that's what Lockheed Martin and Raytheon and Boeing. That's a lot of what it was. And then sovereignty also dictated who and which countries they're sold to in what Niagara, State Department gets involved. But it was all dictated by that. I think AI is that strategic technology.

Does revenue growth matter anymore? We just had the founders of MACAW on the show.

We let the seed there. I know, that's an amazing job.

Yeah. One to 500 million in 17 months.

Unbelievable.

Well done. Thrilled for you.

Does it matter anymore though?

Because every week There's a new one to 101 to 500.

The internal conversation I had about this was of course it Mattered. But the normal has changed. When we did Samsara and Gusto and some of these group companies that are like, yeah, yeah, triple, triple, there you go. Triple, triple, double, double, right? You look at these companies and say, wait a minute. Going from 1 to 3 to 9 to 27 is not interesting, or 1 to 5 to 9 to 27 is not. Whatever. The math is not interesting. You got to go like 1 to 15 to 20 to 100. And they're all, on a revenue basis, more interesting than the stuff we thought was the most interesting five years ago. That speaks to the way value concentrates in the hands of a few companies. That speaks to the fact that these technologies underneath are so high leverage that they're potent in making these companies grow fast. When you actually get a product right, that's what's going on. Durability is a question. Like, the thing that's unknown is we never had so much scale without kind of just taking durability for granted. And what's the question that we all grappled with today? Louisville is an amazing company. Anton's done a great job. Is that going to be around? Mercour is an amazing company. The people that are naysayers, that's what they say. The people that believe in it, we have a huge conviction in Merkur. We think this. We have our own thesis. So sort of everybody's kind of grappling with this and we all have our theories and some people will get lucky. And I do think some of these companies that grow really fast in this will also not be around.

So funny. I'm very good friends with Rory o' Driscoll from Scale, who I think is one of the most brilliantly strategic.

But SaaS or G?

Yeah, exactly. And I learned from a lot. And he said the go to markets fundamentally changed in the world, where bluntly, it's a case. If you just go into a market, scream the loudest in the room, gain mindshare and deliver from there. Your Harveys, your abridges are great examples of that. Do you agree with that?

So if you look at Harvey or who are invested in Lagora and Judia, take the legal space. It's not just that they scream the loudest and they want it. I think the interesting thing that has happened with AI, I want to go back to sort of one important observation, which is for the first time, every CEO in every industry in every country is thinking about, what do I do with this technology? Never happened before. Cloud wasn't like that. Certainly PCs weren't like that Internet wasn't like that. Everybody's like, what do I do with this? Right? So all of a sudden in every department, people popped up early and they got to go around and there was resonance with the customers. There wasn't as much evangelism for the earliest companies. Everybody just wanted to engage. So that's why these companies got initial momentum so fast. But then I want to go back to my second mover advantage. But some of the ones that have started after had a chance to take a step back and be like, oh wait, there's a better technology now. And I think we've learned the proposition needs to be better. The initial diffusion in the zeitgeist was really fast. But the actual deployment to my earlier points, people are like, well, how do we really use this? And that's where now this next generation of companies that are coming are just more sophisticated at that. Is the early mover advantage in some of those companies really going to take hold or not? I think it remains to be taken.

So when you look today is triple, triple, double, double, dead.

Triple, triple, double, double is definitely dead. I tell our investors, don't bring that to me.

What do you do with the generation of SaaS companies you have?

I hope you have it because I have it.

They're good companies, the grid companies, by the way. They're good companies, they're durable companies. They're going to be around. And this is actually an observation. I give Pranav and our team a lot of credit. He sort of said, hey, these companies, venture capital doesn't like them anymore because they grow 20% and they're not the hypergrowth, so nobody wants to fund them. But there are some founders life's work and if you give them alternate ways to endure and scale, they will and they will create value. It'll just take longer. And that's where we actually have also made sure our customer value fund supports those types of founders as well. We obviously want to support the fastest growing companies in venture, but also the ones that are fundamentally good businesses that are profitable if they were not investing in sales and marketing and give them capital to scale their sales and marketing. That's what customer value strategy does and it's entirely focused on those founders deserve to endure and compound because their companies are good, their customers like them, they're growing, they're just not in the zeitgeist.

I've never felt so much uncertainty in what I do. I am trying to understand. It almost feels like Covid where we had these highly transient categories that were created and it's like, do they remain and we actually just do exercises at home all day on pelotons or do we go back to gyms and you didn't know what would be enduring, strong markets and not. And I feel that is the case here. Have you ever felt such uncertainty in investing? And what would you advise me?

I'll give you the same advice that we follow here at gc. This is peak ambiguity. And so everything we do to support founders. Everything you do, you're showing me a lot of your cool ways of supporting founders. Get them excited. All the products and the solutions we have created to support the founders, the question is to what end? And I think having a true sense of long term set of principles that you believe in, in the world of ambiguity, that's all you can lean on. The way you navigate ambiguity is by having a true north. In the US we have this enormous movement towards transforming healthcare post pandemic. And so everything we do in healthcare we go back to saying, is this decision going to make it proactive, affordable, accessible or not? In Europe, the work that Jeanette is doing is very much about Europe's resilience with AI. So everything we do, we sort of look at it and say, is this going to make the economy here more resilient and sort of this investment decision or this relationship decision or this partnership decision or not, and sort of having that kind of a sense of where you're going so you're directionally aligned with your values is the only thing you can lean on. And there's so much uncertainty, it's so difficult. I feel bad for investors that are learning in this era because the signals to determine if your decisions were right or wrong, you in some ways have none. You have this again, do you have this great revenue growth to lean on, but no durability. And then you have, and then you have great margin structures which are revenue. So it's like you have to be values oriented. You have to have a sense for what am I really trying to do. At gc, we say we build deep relationships with people, we build enduring companies and we're doing that to transform industries across the world. And what does that do? It gives our founders access to talent, access to policy sophistication, access to distribution and access to differentiated capital. If we give founders all of that and we have a set of values with which we want to march down these industries, I think we'll be okay. We're trying to take faith in that. And I would sort of have everybody think about that because I do think we are building the future. It's an amazing time. We will shape what this society is going to look like for probably 100 years. I mean, this shift is as big as what electricity was 150 years ago. We get to shape it, but I think we have to make those decisions. What do you want this to look like? And I think that intentionality should always be in the back of our mind as we make the short term decisions, as we deal with fomo, as we deal with how are we scaling our business, how are we supporting our founders, what are the kinds of things we choose to do and not to do? Because there's way more opportunity than any one of us can do. We need a true north.

You continuously mentioned the exponential market size or the insane market size that we have. It makes me think of it's either a Buffett or a Munger quote that it's better to buy a great business at a good price than a good business at a great price. Is there any point in being price sensitive if markets are a trillion dollars?

One of my partners, Joel Cutler, used to say, price only hurts once. It's like buying a Gucci bag. Price only hurts once, but then you never regret it.

Stop.

Shoot.

Whenever I see my mother with a Chanel bag, I'm reminded of the dent it caused.

Well, I think there's actually wisdom in that comment, even though it's a cheeky comment, which is, first of all, when did we ever get price right? I have been doing this for 25 years. We've seen all these models. I am yet to see some investor, at least in our firm, ever nail price in the way they thought it was to going. Going to be. It's usually worse than that. And we make all the money when it's better than what we thought. So if money's all made in, what's better than we thought? Like using price to pass. Investors use price as a reason to pass because they couldn't gain conviction elsewhere. And it still makes them sound pragmatic. I get very ticked off when somebody says, I love this company, but I don't like the price. I'm just like, well, then you don't know if you love this company. You're just taking solace in trying to be like him, a price disciplined investor, because you didn't really understand the potential of this company to see what it's actually going to be. Because if it's going to be destined for greatness, then jump in.

What about if it's a capped upside company? Okay. Let me just walk you through this. There's a data, I'm just making this up. Super interesting data providing company. And you're like, okay, this is a good business. And I can easily see a $2 to $4 billion outcome here either to a strategic or as a public company. And I'm getting in at 80 million pre. That's a great way to make a lot of money. It's a potential 25x on an early stage check and in a $10 million check, I can return my fund almost great. But if it's 140, it's very different to 80.

The multiples 100%. Right. But we say these things. It's a capped upside company. What does that mean? When my nice investor in Stripe, all the guys that I called that new payments were like, this is a niche thing. Like, why are you doing it? I kid you not. I was like, you know, I just don't want to listen to the experts about what they think their industries is or is going to be. Markets expand also. So the humility in this business also is, is just understanding we don't know what's going to happen in the future. If it's truly a capital side, then you shouldn't be doing it anyways. That's not a price question. Like we're in the business of trying to build and back companies that can become enduring very, very large businesses. That's like a precondition. I feel like people get stuck either because their companies are just completely mediocre and they're not even going to be worth 2 to 4 billion, or they're actually great and you're not willing to stretch because you're not willing to believe what the world's going to look like.

I always think of Peter Thiel's biggest investing mistake, which was not doing the next round in Facebook. When did you not do the next round in a company that with the benefit of hindsight, you're like, oh, I should have done.

I don't think we have time for all my mistakes. But I'll give you a very recent example. We have a company that's a Decacorn now. And I actually called the investor who led it at GC saying, congratulations, you're going to make make over a billion dollars on this investment. And you're an idiot because you gave up not making the second billion. You gave up making the second billion. Why? Because you didn't double down. That is where you can get a lot of it wrong. I mentioned earlier in stripe, I've invested 14 times. That's what it takes. If you're in the best companies, you really should be buying into them constantly. In fact, that's the reason to scale capital. The reason to scale capital isn't to be a low margin business. It's because you want to have capital pull the very best ones and really lean into the them. That's ultimately where you drive your return, your best businesses. And that requires courage, conviction, belief in how markets are going to change.

Do you worry about capital concentration limits?

I have invested in, I don't know the exact number, probably over 200 companies and 60, 70% is like 10 companies over 25 years. Capital concentration is the way you drive return.

Which single company?

You just got to be right.

Which single company are you most capital concentrated stripe.

It's about a billion dollars.

Is cross fund investing concerns bullshit? LPs often worry about it, don't like it.

Well, cross fund is an important consideration. We do think a lot about before we cross funds, but we do cross funds. But you want to make sure you have done enough capital to work in the fund that it's in where you feel uncomfortable about the risk you're taking before you cross it. If you really believe in something, you want to make sure that becomes one of your largest positions in that fund before you go to the next fund. I try not to have more than 10 to 15% in a single company in a fund. So at some point, if it's truly a great company, you will be forced to cross because you should have multiple funds benefit from that.

Always remember Brian Singerman saying capital concentration limits are the enemy of great venture returns. Which is why we'll often have 30% in a single company. And I thought, wow, I need to get more courage.

Concentration is key to being great at investing.

I genuinely believe that when companies go public, you have have the choice to distribute or not. How do you think about whether you are better placed than your LPs to manage those positions once going public?

I always look at it as it's a variety of things. One is will our time matter if our time continues to be spent on this company, will it matter in terms of compounding from here or not? So some of the ones we started, for example, that would make sense, you want to stay on and do that. The other thing I look at is how long should we hold it to make sure we drive the best returns for that fund? Is this the company that should be compounding most to keep generating returns and driving performance given our commitments to the LPs? Because a lot of the LPs will have their public sleeve and their private sleeve. You give them stock, they'll sell it and it's like programmatic for them, but we want to make sure we give it to them at a point where we've really captured enough value. So that's another factor we think about in that context, which suggests you do.

Think you're better at managing it than them.

Well, they may not be managing it is what I'm saying there, but by.

Selling it, they're managing it because that's.

Programmatic, that in their private sleeve they're just not going to hold it. And the private team is basically told that once you get stock, you sell. And also the other thing is in our lead companies, where we lead, where we go public, we have a lot of stock. You also have to be measured in how you distribute stock because by doing too much at one time, you could also hurt the price of the stock, which hurts the rest of it. So I think there's also a pacing question of how do you liquidate, how.

Do you think about navigating secondary markets when we look at there's a very strong chance that we have a trillion dollar private company in an OpenAI of the world, how do you think about navigating secondary markets when public market is sometimes not there?

Well, look, I think for the very best companies, private markets behave like public markets. There's a secondary market you can liquidate so your shareholders can take liquidity, employees can take liquidity, you have access to credit, you can do M and A, your stocks, you know, your valuations believed, I'm talking very bit of stripes of SpaceX is, I think OpenAI is going to get there. They're anthropic and so on. Right. So the very databricks is getting there slowly. So the very best, that's what happened. Then there's the very good companies, but not the, let's say the top 10 or 15 private ones, not the magnificent private 10 if you will. For them, going public and getting validated actually could be more helpful. It may be that the secondary market isn't behaving as well, or they can't do M and A as effectively, or they need to access a lot more capital than they can just being in the private markets. And I think those decisions are what ultimately then push you to go public. And then there is the, as I said, this bloated set of companies that are good companies that will compound at 20, 25%, maybe forever, that have no access to public market because they're too small. They're not a billion dollar company growing 30% a year that the public markets would be excited about. And they're too slow for venture to fund. And that's the purgatory where we need innovation and that's where the customer value fund resides to help these companies get to that scale so they can go public. Some.

Is the extension of private markets not an increasingly harmful thing to the distribution of wealth in society? When we look at the before, it would be your fidelities, your t rose and the pensioners of the world, my grandparents would pay them 20bps, 30bps, 40bps. And now with the extension of private markets, you get money and get 2 and 20.

When I published my first book Unscaled in 2018, I had the leadership of Vanguard come by and they talked about, look, Main street doesn't have access to this asset class. So I spent a lot of time in 2018 saying, how do we do that? How do we actually give retail access to our funds? Now with 401k changes and some of the 40 act evolution, you actually can do that. So I fully expect that you will start seeing products that give retail access to the best companies in technology and we will definitely engage in that because it's the right thing to do.

Do you agree with that? When I saw the lafonts talk about this, I was like, oh, wow guys, well done. And then part of me is like, well, isn't that what we want, the democratization of access?

Look, I think everybody wins in this. You open up large pools of capital for investing in technology, but you also open up large pools of opportunity for people that don't have it otherwise. So we don't need to look at it as, oh, we're doing it because it's sneaky. I think it's good for the world and we should do it. And if you're oversubscribed, make room for it. That's where this matters, which is when you have more capital than you want to take on in a fund, would you let it in or not? And what I'm saying is that we should be making room for this.

Do you think fee structures need to change?

I am very much focused on performance as the number one thing. That's why I said in the beginning that I measure us as how good a seed firm as we are in the context of everything we do is like, is our core right? Are we doing the highest risk, highest reward work? Are we helping founders in the earliest stages? So you want to stay High performance. And if you want to stay high performance, then your incentive should be much more focused on on generating carry and making it a prosperous place for your team than generating fees. Which to me can be a distraction by the way, just to tell you, in our business we don't distribute any fees. We invest everything back in the business. And that's a deep belief that we don't want to be in the game where the partners of the funds at General Catalyst want bigger and bigger funds because they can take bigger and bigger distributions. Whatever fees we get, we invest it back in the business.

I'm so sorry to be so blunt, but don't partners make like 3 or.

5 million bucks less than that?

Do you worry that you're not going to get the best partners because they are getting that at alternate funds.

It depends on if they're focused on performance or salary. I think that that to me is a filter and my commitment is that you go deliver your dream and you'll make more money than anywhere else. But it's got to be aligned. We got to be focused on performance and value creation versus being rich in fat and happy salaries. That is just not the culture we want.

Do you think that is the same or reflective of the rest of the venture ecosystem?

I have no idea. I pay no attention to it.

You don't?

No.

Do you not pay attention to your competitors?

I don't know what people get paid there. I don't.

Which competitors do you most respect?

All of them. They all make us better.

If you were to choose one. So I could say like 0.9. I think 0.9 in Europe have done an incredible job really carving out their industry and knowing what is that type of deal.

Andy golden who ran the Princeton Endowment and he's doing some stuff with us now, he had a huge impact on me as I was helping build gc. He always said run your own race. It's actually a chapter in my upcoming book is about that like play your own game.

Do you not think you can learn from others?

No, I want to learn from others but I don't want to be in the game of we're competing in the zero sum game of venture capital.

When you look at that product that you give to founders, you have a lot of products now from the GEOs of your Europe and your India's and your US's to the seed, to the growth, to the customer value, to the roll ups. What product do you not have that you would like to have? Do you have like a square heritage or wealth management Business.

We do.

Of course you do.

We do. And that's actually growing rapidly. It's a fairly large business at this point. We have a roadmap, to be honest, and I always look at it as what do the founders need? And we have a roadmap of things that we think about that we will over time experiment with and see if we should bring in. We have really three products. We have venture capital, starting with seed, we have customer Value Fund and we have creation, which is where we do the rollups and hatches, building companies from scratch, sort of being really builders. We have three products today, but which.

One would you most like to have have?

I think we need to figure out infrastructure, the race in AI. The thing that I'm very focused on learning about, and we're early in our thinking, is in order to get AI right, you have to get energy right. Everybody knows this. And if you think about energy, it's a really interesting opportunity with all the new demand to actually move towards sustainability profitably as well. But in the short term you don't have sustainable solutions. You really have natural gas in the US for example. So, so what is that arc with which we're going to think about energy to really get AI right? That's an infrastructure problem. That's an example of something of like, well, if we care about using AI to change the world, all of our transformation work is about transforming industries, businesses with AI all over the world. Then we need to figure out what to do with energy.

How do you think about how you need to change the capital supply base with the different products? I very much operate in the Endowment Fund foundation world, which is lovely and nice, but does it change drastically when you move across products?

It's a great question because I think as we went through the succession at GC from David, Joel and me running the business sort of most of last decade together, the two of them before that to me taking on as CEO. I think at the same time we had a succession from a leadership standpoint. Ken Chenaul came in, became our chairman, mentored me, but also had an interesting evolution of our LP base because lp, the indomitant foundations, which many of them are huge backers of ours and I consider them sort of really part of our team. The mindset there was we want managers to be dedicated in single strategies and we will create the portfolio. The break in strategy we did was to say, well, no, we need to have all the strategies that make the founders successful and you back us to make the founders successful because then we'll Create Alpha. And that's what we were on a campaign to convince enough of them to stay on with us and do that. And they did. Then we went and got a lot of the states in the U.S. states and pensions because part of it was going back to your point. I want to make sure we create wealth for Everybody in the U.S. so that was like a motivator there as well. And now we're actually very deeply partnering with sovereigns as well. Because as I said earlier, the AI, the transformation of the countries, but there the relationship needs to be more of a partnership. We're helping them think about, hey, what you can be doing in your regions and let us be a strategic partner to you and you be a capital provider to us. Like we're doing the sort of interesting partnerships in that regard.

And you have to go to sovereigns because they're the only ones who can write a billion dollar check.

No, some states can as well. But there's scaled capital in each of these areas. The key is how does your work fit in the context of their strategy. And GC is sort of a flexible platform where people can engage in that context. And we were talking about jokingly before, retail is another one that's about to open up. Right? There's like $16 trillion of retail capital.

That's what will cause retail to open.

Retail is opening up in terms of the 40 act regulations, in terms of the changes in the can 401k invest in alts. It is going to open up and it should open up. And we need to be responsible about exposing retail to the right part of the risk curve in privates. I think it's very important that we do that. So being very thoughtful about if and when we do make gc, we don't do that today available. What would be the right way to do it? I think the whole industry is going to think about that. So in my view, all these pools are there. And I think if we are to service the founders the right way and have the capital and the flexible capital solutions all available for them to build their companies, that we need to engage with all these capital sources that are willing to support different parts of that stack.

When retail opens, is it a trickle or is it a flood?

Hopefully it's a trickle. It sort of starts slowly and then scales. I do think it'll scale in a big way, but I think we should be. We'll be careful because I worry when.

We go back to your very early statement, there's not many Patrick and John or Sam's Or Dario's. The problem is there's not enough truly generational defining entrepreneurs for the supply side of cash. That will only get worse. I'm not looking at retail opening up going woohoo. I'm going wow, this is about to get harder.

That's right. So I think retail can open up to be in the very best companies at scale in my view. I think Robinhood is working on some work there. For example the tokenization and they just announced they're going to create a way to give retail access to some the top companies as well. I think it's a recent announcement. So that's one which is I think there you could be, hey, giving people access to SpaceX and Stripe. You're not going to regret it. It'll do right by them. You'll feel proud of it. What you don't want to do is take retail and put it into the bottom quartile of the venture capital funds that lose money because they got access to it. I think that's where it needs to be trickling in to make sure it goes where return. We should not put retail into very high risk situations where they lose money. I feel very strong about that. We have to be careful. So I think it needs to be trickling down, down the risk curve in terms of how retail accesses our asset class.

What did you do that you wish you hadn't done in the last 10 years? And it doesn't need to be deal. I'm more thinking about like products, strategy.

Firm build, you know the good thing about our culture and I give the founders of GC a lot of credit is anytime I had a crazy idea to support it in. So I've usually gone and have been able to do most of what I wanted to. This is one place I look back and say did I make a mistake? When the financial services market took off, I was like I want to be in the best company. And I was like let's invest in Stripe but let's not do square and whatever else. And when the AI stuff happened I was like I want to be where I think I can risk adjusted make the most money. I think in hindsight we should just go on and index those. Some of the other investors like Zuri, Milner and others that did a great job with it and did very well, I was focused on I want to be in the best. And I was like aha. See how good I I am that I did the best one. And if I could go back I would understand that in certain parts of the Stack indexing, if you can afford to, if you have the capital base too, is a better strategy than trying to pick in a world of peak ambiguity. And that's something that I'm a slow learner. I feel like I've been at it for 25 years and I'm starting to understand that better.

And you've moved to that now?

I have not moved to that, but I'm going to wait to see the next time I missed it in AI. Our friends at Lightspeed did a great job in AI, for example. I think it's going to work out really well them.

Why do you think that?

Because when you know the trend's going to win but you don't know which one's going to win, you're better off backing all of them than trying to pick and meaningfully play and get it wrong. That's a very hard decision to make. And get it right.

Do you regret not being in OpenAI when you had the chance to, but didn't because of the structure?

This is a daily conversation I have with myself and with my partners. I mean, I do regret it because the amount of learning we would had if I was sort of at a front door seat really understanding what's going on. I wish I had that.

Would it have prevented you from doing anthropic?

I don't think so. I think there are plenty of investors that are in both companies. Look, that structure, many people overthought it and I overthought it as well. And there's a lot going on that platform that's changing the world and I don't have a front row seat. So yeah, I do regret that a little bit.

We mentioned focus on performance. Circle's IPO was nuts and it did wonders for the fund in terms of returns. How did that fund return? Look? We were chatting about it outside.

Yeah, that fund is one of our two or three best funds. And just to tell you what was in it, Livongo was in that. Snap was in that. Circle was in that gusto. It's probably going to end up being a 13-15x fund. Story is not over yet.

How big is the fund?

It was 500 million.

Wow. Well done.

We need to keep doing it. That was a long time ago.

What is GC?

In 10 years, I think GC is.

Going to look like the most diversified solutions for founders to build enduring companies. That's the lens with which we justify everything that's on it. And if you looked at it, GC as a business is going to feel Like a strategic conglomerate where every part of GC is in service of founders. Whether it's giving them access to distribution or access to policy or access to capital or access to wealth management. It's all about founders. So it's the platform for founders.

How many team members do you have?

We are over 300 people.

300 people?

Yeah.

Positively small compared to Andreessen. Absolutely.

We're tiny.

Final one, then we'll do a quick fire on the future of Vantia. Everyone does this binary. You're either, you know, the massive AUM gatherer, or you're the boutique provider, and that's it. Everything else a la Pibel. Do you agree with that binary view of venture, or do you think it's an alternate view?

I don't like that view. I don't like that framing, because my.

Framing is actually Walmart and Chanel.

Totally, totally. But I would say we want to have the biggest AUM in venture because that means we're doing the best job. But not because we have a lot of companies, we've raised a lot of money, but because we're in, like, 20 stripes.

Well, the biggest AUM doesn't mean you're doing the best job.

No, no, I'm saying. I'm saying the kind of Aum I want is the biggest because we have, but with the fewest number of companies, meaning our companies have created a lot of value. It's not the amount of money we raised. AUM can be one of two things. How much money did you raise? Raise, or what is the value of the capital you raise? I want the value of the capital you raise to be the biggest, but the amount of money you raise to be smallest. That's when you've created the most alpha. So that's why I think this biggest AUM is not like a very informative way to look at it. And if you're boutique, you could still have really big AUM if your portfolio was only the top 10 companies that got funded. If that was your portfolio, you actually would have the biggest AUM even if it was a $500 million fund or $300 million fund, whatever you call it, the focus needs to be on being the support of the best founders to build the biggest companies, which will give you the biggest aum, who'll give you the biggest performance. And not focus on, can I go raise the most amount of money for venture? That's why I said in the beginning, our aspirations in venture capital is to be the best seed firm in the world or second best after you.

I have two more. What was the most memorable first founder meeting? And then I'll tell you why I laughed.

I mean, I have to say, it was with Patrick Carlson. It's just one of those, you know, like the movie Sixth Sense, when the ring falls and the guy's like, oh, shit, I'm the one who's dead. And you just feel like you didn't know something about the world and how to think about it. That's how I felt with him, because I asked him, who are your ideal customers? And he said, they haven't been born yet. And he was talking about the developer movement. Remember, this is 2010, right? Developer movement and what's about to come. And I'm just like, oh, crap. I don't even have a complete view of the world. And what's happening around me is how I felt in that meeting. And I was like, I have to back this person. I don't even know. People, payments. I mean, everybody. All the payments, people are telling me what's wrong with the payments. I was like, I kind of don't care. I don't know what's in this thing. But he sees something and we have to be part of it. And that moment taught me a lot about humility in terms of what this business is all about. It really is about backing the best people. And honestly, it had a huge impact because I saw him and John build Stripe. I was like, well, why does our business run so shitty when we are in service of trying to help build businesses that can be run really well? I want to run well. GC should be running with the same rigor these companies run. And I think we still run pretty good. We're still a very messy company, but the aspiration is we want to run with the same rigor as, you know.

Companies like Stripe, too, which loss hurts the most. So the reason I laughed when you just said about that, I've only lost one deal in three years. It's not me being arrogant. It's just the truth. I lost to you, which is great.

And you know what I hate, by.

The way, when you lose, because we beat people too, and they phone up and like, well, it's C of Ash and Kai. Do you know them? Yeah, yeah, out of Shopify. Amazing guys. Love them. Fantastic. Well, that was Jeanette and, like, awesome.

Great founders.

You know, I freaking hate, though, is when other investors call up and they're like, hey, can we, like, share it and have some of yours? And you're like, are you kidding me? No.

Yeah.

So I never do that.

Yeah.

But that one, like, sticks in my mind is one. I'm. I'm annoying.

First of all, Harry, you should be losing more. I'll tell you a little story. When we moved to the Bay Area, I lost this company at a series A of a company called Cloud Studio. We already did the B. And I remember my partners from Boston came, and they were. They just felt bad for me. They're like, you can't be losing because that's just going to, like, emotionally devastate you, and you're not going to be able to compete here. And I was like, are you kidding me? If I'm not losing, I'm not winning. Because the very best founders go meet all the five to seven great firms, and they pick one. So theoretically, your win rate, as long as it's over 30%, you're actually maybe in the right fight. So it's very important to be in the right fight. So you actually want to feel like you're losing more. Everybody that in the team, when they come and tell me I haven't lost in my card game, I'm like, well, then you're just in the wrong pond, buddy. So I think that's, like, an important thing, which is there are so many smart people. I just lost one the other day. There you go. There you go.

That's my point.

That fucking hurts, too. But I was worried about saying that.

I think we should enjoy the pain. I actually think if we're losing, we're winning. Winning, that's like, something I genuinely believe about ventures. Like, you need to be in the right fights, and then you got to win your fair share and not dwell on it. Beyond that, the things I lost, I mean, I have so many of these moments. Like Drew Houston, when he was starting Dropbox, I asked him come work at GC with me because I had him intern for Chris Dixon. I'd backed Chris's company, and I said, come work with me. He's like, no, I'm going to go start this file storage company. I was like, file storage? There's Moji. That was the first million dollars. Would have been a $2 billion return. Learn. Because I'm like, what is this thing? Even though I was willing to work with this guy, but I didn't give money on that.

But you didn't lose it. That's a miss.

Well, to my own brain, that's a miss.

So I'm like, you lost it?

I lost a Series A of Stripe. I lost a Series A of Samsara. I lost a series A of snap. And the first one I won was a series a of gusto. If I look at my most competitive fights when I first got to the Valley, I'm like, oh my God, this just sucks. No one's ever going to pick me. Fuck this. I'm getting mad at Boston, you know, and I did. I lost a lot. But the key was I stayed on and then I was able to, you know, do the next round and. But those moments make you better. It just sort of. You just got to realize there are a lot of smart people in our industry. They're just very smart.

I called up my mentor, who's this kind of one of the best investors in the world, billionaire genius, and I called him up after losing this deal to Andreessen. I said, fucking hell, like, what the fuck? And he's like, harry, all of my biggest returns I've never made. When I won the deal, I always lost the deal. And then I just had to scrabble and buy secondaries from angels, from operators, from founders, and all of those ones were my best returns.

The thing is, in the very best companies, you don't get the amount of ownership you want anyways because founders command a premium and so you're constantly building ownership after that. As I mentioned, my biggest overall investment is in Stripe.

How much do you have in Stripe?

Across everything, it's still sub 10%.

And so like 2 billion? A billion?

No, no, more.

5 billion more.

But I think that does more than 5 billion. I think the key point is it's a lot. But the point is Stripe's going to be a trillion dollar company. You just got to give it 10 years. So it's a compounding business that Patrick and John always say infrastructure is hard, but it also compounds. And they're sort of steadily just doing that and making some really smart choices in this AI world. And so you got to have a long term view. We'll have a 25 year hold probably on Stripe in some form or the other. So when these companies are good, you want to keep buying in and then at some point you say, okay, I have done enough. And now the next 5x, where it just seems extraordinary to think about way more beyond that. Maybe I'm going to stop. So at some point you have to sort of say, okay, I got to move on to the next thing. There's some firms that are trying to make all their money on SpaceX and keep buying SpaceX. I'm like, that's great. And I actually think Elon's got a lot of Runway with spacing, that's a good investment. But I want to go back to the next generation of entrepreneurs as well and figure out if we can generate alpha there too.

Listen, dude, I could talk to you all day. I need to do a quick fire because I'm sure you actually have some other place to be in life. Tell me, what have you changed your mind on most in the last 12 months?

This idea of indexing, being in every company. When you have macro trends, should you index or not? I'm being open minded to thinking that way about major technological trends or market shifts.

What has been the biggest challenge in changing your leadership? So like, for me, I'm very emotional and as I lead I need to dampen my emotions.

I think it becomes really hard going from becoming a master at something to being a teacher at something. The reality is when you can teach something is when you've truly mastered it. And I don't think I'm very good at that. Some of my partners will say gibberish comes out of your mouth when you try to teach. It's much better. Just watch what you're doing and make sense out of it. I'm still trying to figure out how to crack that.

What would be your single biggest piece of advice to an LP navigating venture today?

The proposition for founders has to change. You want to embrace entrepreneurial VCs that are innovating around that.

What worries you most in the world today?

The short term alignment of value creation in business with long term prosperity of everybody being inclusive and abundant in that.

What would you do if you weren't scared?

I'm not scared. I don't operate with fear. I'm doing what I would do. I think we take a lot of risk. I think we're innovating in every dimension that we possibly can. We're pushing ourselves as much as we can. So I'd like to think I would do what I'm doing.

Does money make you happy?

No. Money is a byproduct of the impact I want to create.

Biggest advice on parenting.

Teach them to be unique and in the world of AI, teach them to ask questions, not solve problems.

Is college less valuable than ever?

I have a 16 year old and he's definitely going to college. I have an 11 year old and I talked to him the other day and I said, hey Ajay, you may not need to go to college. The world may change in how we think about developing skills. He was happy about that.

Final one for you. What are you most excited about? I like to leave on like a tone of positivity. What are you most excited for when you look forward?

Look, technology is neutral. What I'm most excited about is that over the next 20 years, if I look at GC, we'll probably invest what, $300 billion, $500 billion into the world through helping shape what AI does for society. I and my partners and my broader team have the opportunity to leave a mark and I want to get it right. I want to get it right where when I'm some days living a senior living facility that I'm like, hey, I did right with the world. It's actually turned out to be okay. To the shit shift.

Listen ham on shows like this remind me why I love what I do so much. You gotta remember I love investing. This is my true passion. And being able to speak with you and discuss the craft of what I love so much is such a joy. So thank you for being so brilliant.

Thanks for having me. This was fun. Really enjoyed it.

I think you could tell just how much I enjoyed that show. If you want to watch that episode on video, you can check it out on YouTube by searching for for 20VC I always want to make the show the best it can be. Let me know how I can make.

It better for you.

Email me harry20vc.com but before we leave you today, I love seeing the team come together to make this show happen. What I don't love is trying to keep track of all the information, the data and the projects that we're working on across dozens of platforms, products and tools. That's why we use Coda, the all in one collaborative workspace that's helped 50,000 teams all over the world get on the same page. Offering the flexibility of docs with the structure of spreadsheets, Coda facilitates deeper teamwork and quicker creativity. And their turnkey AI solution. The intelligence of Coda Brain is a game changer. Powered by Grammarly, Coda is entering a new phase of innovation and expansion, aiming to redefine productivity for the AI era. Whether you're a startup looking to organize the chaos while staying nimble, or an enterprise organization looking for better alignment, Coda matches your working style. Its seamless workspace connects to hundreds of your favorite tools including Salesforce, Jira, Asana and Figma, helping your teams transform their rituals and do more faster. Head over to Coda iO20VC right now and get six months off the team plan for startups for free. That's Coda CEO 20 VC and get six months off the team plan for free Coda iO20VC and while Coda keeps your team aligned, Radix makes sure your startup's name is just as sharp. This one's for all you tech founders out there. You finally come up with the perfect name for your startup. Then you check the.com and damn, it's taken, taken, parked, unused or priced like rent in Palo Alto. So you settle with extra letters, weird spellings, whatever it takes. But hey, you don't have to compromise because now there's finally a domain for tech founders like you. Tech domains get the startup name you actually want on tech. No compromises. What's more, when you use tech, you signal to your customers an investors that you're building tech with just your domain name. Isn't that cool? So if you've got a name in mind, search for it now with tech on a trusted platform like GoDaddy or visit Get Tech 20 VC to grab it. You've got the name locked down with Radix. Now it's time to get the fund structure just as solid. If you're listening to 20 VC, you know we have a really freaking high bar. Well, Angellist is the modern platform platform used by the best in class venture funds where over 40% of top endowments and banks are LPs. Their customers include a top five venture firm 20VC and they now have, check this out, $171 billion of assets on the platform. They combine an all in one software platform with a dedicated service team that moves as fast as you do. One manager said this awesome quote angellist feels like an extension of my fund and not another said Angellist gives me total peace of mind. The attention to detail, lightning fast response time and just real sense of ownership from the team are exactly what I need to stop worrying about back office ops. So if you're starting a new fund, don't be a moron. Just use Angellist. They're incredible. Head over to angellist.com 20vc to learn more. As always, I so appreciate all your support. Stay tuned for an incredible episode coming on Thursday with the one and only Jason Lemkin and Rory o'.

Driscoll.