YouSaid · the spoken record

Ev Randle

lines on the record: 83
first: 2025-11-10
most recent: 2025-11-10
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“I think it's a question that we need to constantly be asking ourselves. And I think if we ever find that our network access, the close relationships we have and the people we have access to is slipping, or we're not getting access to the right people or the right network nodes, I think it's something that we always need to be sharp on and revisiting. But I think if you think about kind of like the cultural touchstone founders of today's AI era, is there anyone more than Brett Taylor who represents this wave of AI applications? He's like the godfather of AI apps right now. And when you think about these really cracked young teams in AI, who do people look up to more than Brendan at Mercourt and what they've done on the AI infrastructure side? At least as far, even with our strategy, even with the trade-offs that mean that we can invest in every single good round, we've still been able to attract and partner with and I think build really great relationships with a lot of the founders that people look up to in this AI wave. And I think our network thus far has been excessive.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“The lab investments are amazing as well, but I think if we're going to stay small, the only way we're going to impress LPs is by having incredible cash on cash returns. You are.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“You have on your investment team, but I think there's so many different ways that we can play the game and generate maybe even better money on money returns than folks that are investing in the labs, even though I do think the labs have obviously been amazing investments.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“And now you're benchmarked poorly against them because you missed one of those things. For a firm like benchmark, it might not make any sense at all to invest in a $5 billion financing in a lab, even though those are good investments because of our fund structure and because of our lean size. But our lean size and our smaller fund size also allows us to do other things that we think could even generate better returns. Out of our last fund, our five best investments in that last fund today held at LRP last round price are about a 60x. We have two 30xs and we have 220x's since ChatGPT was released, there isn't an open AI round that touches that return multiple and that money on money multiple. And we have five of them. And each of them, I think, have a fair amount of upside even from here today or maybe a lot of upside even here from today. I think you have to kind of choose the game that you're going to play and it's based on how big your fund is and how many people”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“It kind of gets to the question that I think some people have. I don't think you've had it, Harry. You've been very kind to us, but I think some people have asked the question, did benchmark miss AI? Did benchmark not get in on the AI wave because they're not in one of the labs or they weren't in mirrors, they weren't in thinking machines or any of these investments. I'm a big believer in Conway's law. And Conway's law is this programming concept that when it's super dumbed down for people like us, Harry says you ship your org chart, or the product you ship looks like your organizational structure. I'm a huge believer in that for venture capital firms as well. I think you ship your fund size or you invest your fund size and your team structure. If you have a $7 billion fund and you have 50 people, you definitively need to get in on these mega rounds. It is the only way that you can put a billion dollars of capital at work productively in a single shot. And if you don't, and it ends up being successful, you are now left in the dust where all of your mega fund brethren got those returns.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Cases, but it's really a talent scarcity and like a talent tech mode where there's just not that many people that know how to build these products and build off of these models in a super intelligent, tasteful way, which is why you're also seeing people go for billion dollar contracts and make LeBron money as an AI researcher.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“I definitely disagree with that. I think the moat is still fundamentally in technology, not in distribution. I think distribution obviously gives you the right to build differentiated technology. But I think one of the huge learnings that we've had as an industry is how damn hard it is to build good AI products. Like a good AI product is so much different to build than a good SaaS product. Like you need different people. There's so many different parts of a good pipeline in terms of where do you bring in LLMs? How do you improve them? How does it fit within a general workflow? It's not just bringing in the OpenAI API and like using it within the text box or something. It's actually extremely nuanced and complex to build an exceptional AI product and one that's going to outshine the labs applications themselves. So I still think it's technology. It might just be different in terms of like maybe it's not a tech mode in terms of having like, you know, a unique database that no one's ever built before that's more efficient for X, Y, and Z.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Again, I think the things that we need to hold into our head when we're thinking about, man, you know, we have companies going zero to 100 in less than a year. We've never seen that. But at the same time, is it easy come, easy go? We had early examples of this. I'm comfortable saying this because now the company has rebounded and to my knowledge is doing really well. But I remember when people were talking about Jasper, like the two AI investments that started the wave were stability AI and Jasper AI. And, well, stability, different story, but Jasper, I think it went zero to 100 very, very quickly, but then actually started shrinking. And it was because it was sort of easy come, easy go with the revenue, and they hadn't built enough scaffolding and they hadn't built enough actual true value in order to really sustain the customer relationships they had and sustain their growth rates. So the way I've actually been thinking about this, especially as it relates to, because I think the other aspect of this is that what is the risk?”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. One of the things I've changed my mind on over the last two years, there's these AI inference cloud businesses. So it's like, who's going to be the AWS GCP Azure of the AI era? And when Coreweave was first raising in private markets, I was like, oh my God, they're reselling a commodity. They're a middleman. They're a broker of compute. It's going to be low margin. Yada, yada, yada. How wrong was I? The market's down a little bit. But last time I checked, it was a $60 billion public company. Nebius is a $30 billion public company. There's over $100 million of public market cap and there's several private players that are growing astronomically as well in this AI inference cloud. So I think sometimes we can twist our mind and knots over like, oh, is the business quality okay when you have demand like this like you had for the initial hyperscaler clouds? And I think we're seeing an even greater cohorted demand curve for AI inference. Sometimes”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Unbelievably large business, probably a trillion dollar business if it was fun out of Amazon. So that is the idea that I think we need to all get in our heads is like, it's not going to be every company. It's not going to be every market. But for the right AI companies in the right markets, the size of their revenue per customer is going to be so much larger than SaaS that even if they have lower gross margins, it's going to be a much, much more valuable companies.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly. So let's think about AWS, for example. Like AWS, actually, I don't know their exact gross margins, but they're not as high. They're not 80%. Let's say they're like 50 or 60%. I know that they're operating margins, I think, around about 30%. The thing about AWS is it is the largest line item for essentially any large software business versus anything else that they pay for. Like you're paying more for AWS than you're paying for Salesforce, Workday, any other SaaS company by a wide, wide margin. In the early 2010s, you had companies doing like $100, $150 million of revenue and people started to be like, what is this $30 million COGS line to Amazon Web Services? Like, what in the hell is this? And I think that's like an amazing example of, yeah, does AWS have lower gross margins than Adobe? Of course it does. But everyone that uses AWS and is a core customer of AWS spends multiple on AWS than they do on Adobe, which is why it's such an unbelievable.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“And it's such a better intellectual exercise than trying to compare it to SAS, which is just a very, very different business and it has a very different pricing and business model that isn't going to be as relevant, I think, over the next 10 years.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Think we should not be placing that much emphasis on margins today. I think the work that we should be doing is trying to understand what is the terminal gross margin structure look like for these businesses. And then also what is the absolute gross profit dollars in each of these categories that these companies can represent? Because it's just, again, like I think the folks over at Reeseen Horowitz have done a lot of good work in terms of evangelizing this idea that like if you have high gross margins as an AI app company right now, it probably means that you have very little inference expense, AI inference expense in your cogs, which means no one's actually using your AI features. It's not the easiest thing to understand what are these AI app gross margin profiles going to look like in five to seven years. But I think that at least trying to go from first principles and reason about what the gross profit dollar per customer and the gross margins of these companies in five to seven years look like, that is so much more worth doing.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“If you just think about the P&L of a SaaS company, you know, Robert Smith, the CEO of the first firm that I ever worked at, Vista Equity.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. I think it gets to something that I desperately want us to do in the venture industry, which is we need a new taxonomy for AI companies. And what I mean by that is AI app companies are meaningfully different than SaaS companies in like a dozen different ways, yet we keep trying to shove all the metrics from these AI app companies into the frameworks that we created for SaaS.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Spending on this company. And they're like, oh, you know, 250K. It's like, okay, you have seven products from Service Titan from SaaS 2.0, and you have one product that's just out of beta from this new startup in Voice AI, and you're spending as much on that as you are on Service Titan, like the system of record for everything that you're doing. And they're like, yeah, well, you know, like we no longer have to staff, you know, three receptionists. We can staff two. And then we're now able to actually accept calls and book appointments 24-7 rather than, you know, the nine to four schedule that our receptionists were sitting there. And so it's driving more revenue and more impact than even service Titan was doing, you know, given that capabilities are just so much broader and real than the impacts that SaaS can have on companies.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Think that it does for a lot of categories. I mean, it remains to be seen, right? Because let's say you're doing AI for veterinarians. Maybe there's just not enough vets that have enough money to actually create a billion of net new in a given year. But I do think that, yeah, for so many categories that seemed like maybe they were kind of middling in size, a lot of what AI has been able to do, especially if it can touch something that a labor force within a category was doing before, we're seeing much, much bigger markets. As one example that I'll give you of this impact, we at KP were invested in a home services AI business that was essentially a 24-7, like its first product is a 24-7 receptionist for HVAC people, home services, anyone that would be a service titan customer. And we were calling customers and we're like, okay, how much do you spend on service titan? They're like, you know, 250K. It's like, okay, well, how much do you spend?”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“You essentially, if you're, especially if you're a multi stage fund, you have to have a bet in that category because it means that it's going to produce really big outcomes. Instead of adding a billion dollars of net new this year, I think code generation is going to add, I don't know, four or five billion dollars of net new across every single product and service that's available for people to buy both on the B2B and B2C side.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“The thing that everyone has underestimated thus far is just how immense of a potential market code can be. So when you think about cursor, I think a lot of people are like, well, they're like relative market share has gone down a lot because at first it was really just them and then Cloud Code came out and then Codex came out and now cognition is scaling. So instead of like, yeah, I don't know, like 80% of the market or something, maybe they have 50 to 30% of the overall ARR in the market today. Again, what people are missing is that the market of code generation has gone something like, I don't know, over the last two and a half years, it's gone from essentially zero to probably like six or seven billion dollars of ARR. And something that we used to do at KPN Founders Fund is try to identify what are the golden categories. And a golden category is a category that as like the entire market for a single product adds a billion of net new ARR in a single year. And like if you find a golden category,”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Mastering the kind of commercialization effort there, and then encoding anthropic still with Claude Code and Sonnet and all the models that they have is probably still a little bit ahead of OpenAI. But I think given ChatGPT, I think I would probably rather do OpenAI at 500 than Anthropic at 350. But I both think that they're relatively good investments even today.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Obviously, a Kleiner Perkins, we invested in anthropic and we had this debate a lot internally. This is like a fun debate, you know, OpenAI or Anthropic at last round price. I think they represent relatively different things. I think in terms of downside risk, it's hard to imagine anything that ChatGPT off of its growth trajectory. I don't know what could stop ChatGPT from growing at the rate that it's growing. And so I think that asset alone is just unbelievably valuable and is completely locked in. There's just no way that it's not going to be the most important kind of consumer destination over the next five years and consumer app over the next five years, where everything else is still kind of hand-to-hand combat is obviously encoding. I think OpenAI has actually done an incredible job with Codex and made up a bunch of progress against Anthropic that they didn't have before. And then obviously everything on the B2B side. I think right now Anthropic probably has a bit of an edge on B2B. They've spent a lot more time and resources towards really”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it'll be a trillion dollar company next year. Yes. They could probably raise at the end of the year Q2, I think OpenAI could raise it a trillion dollars, no problem.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“An instance where I haven't been exuded neuroplasticity enough, I actually have a very recent example of this, was actually the OpenAI round at $32 billion. You know, I started my career in private equity, which I think there's a lot of strengths that come from that, but has also definitely given me some blind spots in venture that I've needed to unlearn a little bit. And when I was at Founders Fund, I was actually extremely positive on OpenAI. I left Founders Fund right after ChatGPT came out. And ChatGPT, when it came out, was one of those moments where you're like, this product is it. Like, this is so unbelievably cool. And you could just tell that it was going to be a massive, massive product. And then the $32 billion round of OpenAI came around when I was at Kleiner Perkins. And all of a sudden, I was like, oh, man, this structure seems really gnarly. You know, they're going to have to convert this somehow. It's a nonprofit. They're selling these employee units. And I think they're going to dilute the hell.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Seeing how they operate because he thinks once you've seen it and once you know the it of what makes an A team tick, you can one much easier see that in the wild and then two you can really you know hold the rest of your management teams and founders that you work with to that really high standard. Mamoon more than anyone has just developed this impeccable taste around a mix of products market and people. If you think about his huge huge winners whether it's Figma, Gleen, Rippling, they all have like a common through line of, you know, it's B2B software, but it's almost like consumer-like software that demands really high user love and engagement. And he's just developed this really, really tight understanding of where he shines and where he has a really deep understanding of companies. And then he's like really sharpened his taste in doing that. And so I think he's definitely encouraged me and encourages people that he works with to really develop like a specific form of taste around the people and the products and the companies that you think are going to be.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, Mamoon, I've learned so much from Mamoon. He's a wonderful mentor. I mean, we were talking before the show, Harry, about the kindness that he showed you when you were young and he did the same thing for me. I think the biggest thing that Mamoon has taught me, this is a reflection of what he did and has done in his career. I think the two biggest things are, one, he really imparted onto me that you need to early in your career see excellence up close and you really, in terms of like a company, a management team, a founder, you need to see how the absolute best operate and do the job of company building. Because if you don't see that relatively early in your career, it's much, much harder to spot it in the wild. And you also don't know the bar to hold your other founders and your other management teams too. I think he does a very good job of getting younger folks that work at Kleiner Perkins or even back at social involved in the very, very best companies in those boardrooms.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Complete truth seeking everyone trying to get to the best answer. I remember a few months into the job, I was like on an email thread and just like teed off on Keith or oh boy, our good friend. And, you know, at any other firm that might be a fireball offense or you might get a tongue lashing for doing that. But at Founders Fund, it was like a pat on the back. It's like, yes. It's like, that is how we do things here. It's flat. We're just trying to get to the truth. We're not trying to uphold some political bureaucracy or something like that.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“From the outside, in, I mean, obviously, Founders Fund is a bit of like a black box. Everyone's like, wow, the returns are amazing. There's a bunch of weird personalities within that place. Like, how does it all happen? When I was actually doing back channel references on Founders Fund before joining, something that everyone said to me that they thought was a negative but ended up being a huge positive. They're like, oh, you really got to watch out about the culture because I've heard that they yell at each other during ICs, like investment committee meetings. And like they get super intense. And then a few months into the actual job at Founders Fund, I realized that, yeah, sometimes people did yell at each other at ICs, but it was almost like yelling at your brother or like yelling at your sister or yelling at your best friend. Everyone was so secure in themselves and the relationships that they had with each other and they all have extremely deep relationships with each other that you could actually just be extremely truth seeking. You weren't afraid to step on toes. You weren't afraid to do anything that might be seen as like, oh, you shouldn't say that to a GP or something. It was just no hope.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“It's super valid. I think, again, if you're at Founders Fund, you're full in and you're all in. And so I think most of us that we're young at Founders Fund at the time all had deadlines, like unsecured deadlines that we were using to do these side kind of personal investments. And by the way, it's turned out to be an unbelievable portfolio for myself personally. And it's all worked out. And so I'm very glad that I had it. But I think that's part of, you know, he throughout his entire career has really, again, designed his organization so people are all in. He had like a bonus system for PayPal employees. If they lived within like a couple miles of the office, you'd give them more money. Like, say he just designs the orgs this way. And so there's less pressure for the young folks that don't have much net worth yet for sure, but they still expect you to be scrappy and find a way to do it.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“His firms rather than his investments. So the way that he's designed Founders Fund is that he creates all these incentive structures and mechanisms almost to constantly be testing your conviction. So there's a program, for example, at Founders Fond where anyone that works on an investment or if you're leading an investment, you can personally invest alongside the firm in that investment, almost as if you're angel investing. And first glance, it just looks like this amazing”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“The sequential numbers historically for a company, and then all the numbers going forward. And it's almost like she's reading the matrix code as it comes down. And she's seeing what the company will become on an eight to 10 year time horizon when she sees what the numbers are. And so she'll look at a DoorDash model, and that was an investment that we had led at KP out of the growth fund at the time. And she won't see seven years out, 80% growth or something like that. She'll see that 20% of households are going to be ordering from DoorDash on a monthly basis. And she can visualize that. And so from her, I just learned that when you use numbers in venture growth and when you want to be quantitatively driven, don't get stuck into a quantitative lens with it. Actually use that to drive the narrative and drive the story of an investment. And that's been an incredible mental framing that I've used. With someone like Peter Thiel, Peter, I think so much of his cleverness and so much of his genius is actually in the way that he builds.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“One of the things I really love about the asset class that we practice our craft in is that there's so many different ways that you can be successful at it and there's so many different strategies and frameworks that you can employ and still generate amazing returns. And each of the people that you just mentioned have very, very different styles and very different ways of practicing their craft. I think if I was to lay out for Mary, for Peter, and for a moon kind of what I learned from them specifically, I think with Mary, she does such an incredible job. Everyone thinks of her as this quantitative investor. You know, she had her time as an equity researcher at Morgan Stanley during the dot-com bubble, and then she came to Kleiner Perkins, obviously. And everyone talks about these DCF models she creates and all the numbers that she does, but she's really the most qualitative investor that I've ever worked with. And it's probably a surprise to hear that. But what she does is it's almost like she's reading the matrix. Like she lays out”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“Thank you, Harry. I have actually been listening to 20 Minute VC since 2017, which ironically I think is the year that you had Peter on the first time. And it's just been so fun to watch the show and the platform that you've built grow this way. It's almost like watching a startup become an IPO worthy company or something. So congrats to you, Harry.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source
“I think we should not be placing that much emphasis on margins today. We need a new taxonomy for AI companies. Like Tiger Died, and we got six or seven more tigers. I don't think Ravi or Hamant or even Ben and Mark at this point. I don't think that they can go to LPs and say, we're going to get you 5x net on that. When you're writing billion dollar checks, that is your main product. Go talk to the principals, the junior partners, and the associates at those firms. And you tell me that capital velocity is not the North Star of those firms. I think Tiger's going to end up much better than anyone thought they were going to end up.”
2025-11-10 · The Twenty Minute VC · 20VC: Benchmark's Newest General Partner Ev Randle on Why Margins Matter Less in AI | Why Mega Funds Will Not Produce Good Returns | OpenAI vs Anthropic: What Happens and Who Wins Coding | Investing Lessons from Peter Thiel and Mamoon Hamid · IDENTIFIED FROM THE TRANSCRIPT · source