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24:12I just think it's such an amazing thing to do. We're going to talk in a second about that blog, building a product that touches everyone and changes everything. It's just amazing. I'm answering the question you asked at a financial level, just trying to be Canny as an investor, but I think step back, both of them are stunningly amazing ambitious companies. I think you got to take on Theropik at that. Yeah. Just enterprise software is bigger than consumer. I would take on Theropik. I'm getting the bigger market at a third of the price. I know it's simplistic. That's the beauty of seed investing.

24:39You get to shoot from the hip like this. But there's something to the fact that at the end, the enterprise software somewhat counter -intuitively is larger than consumer, right? Small numbers of consumer businesses are the biggest business on the planet. For sure. That's the biggest business is SME. I actually said it's not bigger smaller. What I'd say in this is enterprise businesses can find multiple profitable niches and there's lots of 10 billion, a hundred billion dollar plus outcomes. The thing in consumer is, there's only one Google and no one can even name the five other search competitors.

25:06The attractive thing about open AI is it probably is that player. Both have huge outcomes and they're future just different ones. When someone's trying to value it and was going public, the vast bulk of the value for open AI will be some estimate about what percentage of individuals and porcelain pros and probably enterprises will pay 20 bucks a month or 200 bucks a month for general knowledge. And on traffic will be all about, you know, what percentage of API businesses need Claude or wealth and fix. Guys, we're on OpenAI where you mentioned that kind of building and the importance of building for consumer Rory and you touched on the essay Calvin French Owen who was a co -founder of segment.

25:45He wrote a brilliant piece and I know you read it Rory. How did you reflect on this. He wrote about what it's like to work at OpenAI. I just always a well -written essay and a real insight to what it's like to be in, you know, as I say, one of the most exciting startups of our generation. He made it clear how even than this big thing, it's just small numbers of people can get shit done. It sounded like a very impressive organization. Actually, that's the big takeaway of reflecting on it now, actually. Because look, all the weird psychodrama at the top, all the structural issues, it It sounded like down at the cold face, shit gets done, smart people move in a non -hierarchical fashion, can make decisions, and get stuff done pretty quickly.

26:25I actually thought that was actually the bigger half from me from that, which is regardless of what's going on at the top, it felt like a very functional product and angel organization and great place to be at. I actually enjoyed the essay just thinking, wow, if I was an engineer in 25, is exactly right. That's exactly where I'd want to go. Even apart from the salaries, which apparently are reasonably attractive, it's just like the getting should done part of it It's like he talked about the product issue was a codex where it was a 10 -15 person team including product and engine They just got it done.

26:54I mean that kind of excitement leading to a world -class product is human and almost On reproducible part of any a career. It was a great essay. It was like, yeah, this is a good thing all noise be damned Maybe it's a little silly, but it took me back to the vibe pre IPO of Google. Harry, this was a while ago, but before Google IPO, it was a little bit like, it was a magical place. And the internet was dead, there were no jobs, okay? Half of the folks I worked with in my first job were unemployable, and they all went to Google and made what was back then an incalcul about a money by going early.

27:28And it was a bucala campus, and it was all about doing great things. and Google had built its own infrastructure. So it had access to capabilities no one else had. That article is like everything's about GPU cost, right? You can do anything you want at OpenAI. You just got to, it's kind of like a rebooted version of this incredibly intense, but also, and when they moved Google to like Mountain View, they designed it to be this bucolic campus to insulate you from the crap. So you could just do the greatest things in the world. And it feels like this is a 2 .0 version of it that they're trying to build.

28:03But today instead of people staying at Google for life, they stay for eight months. So the analogy breaks down. But a man, you read that, and if you step back for a minute, one, he laughed, co -founder segment, right? But where else would you want to work? Tony. If you're ambitious, and you read that, I mean, where the hell else is a moment? I might even throw away my $2 billion venture firm and go work at one of these places. That's been known to happen. For real. I might regret it 36, 48 months down the road, but I might do it. It's funny, you mentioned Google there, and I'll never forget being told by a guest a year ago that Google was successful because of the early partnership decisions in large part.

28:40And one of the big announcements this week was that Pplacity's raised another hundred million, and an 18 billion dollar valuation. Honestly, there was so much demand from the 15 round that they upped it to 18, and they also announced partnerships with AirTel making the number one downloaded app in India. What do you think happens to Pplacity, and how did you think about that on? They got something right early that now everyone figured out, which is that LLM on the own just with historical still data, not nearly as interesting as LLM plus up to date search data so you can get real answers to real questions.

29:14They were the first to have that. That was a real key insight because it just answered exactly the question you wanted. In a way that, you know, we all year and a half ago, all the early charge EPD models just didn't have contemporary data. So you could do funny things like ask it, who's the president? And it wouldn't know, it would say, what a, what a, what a, president got right. But it wouldn't know the prime minister of England, for example, because you were changing every half an hour. So that would be a good example where Peplex, you could go out and catch up on who you later as prime minister is, Harry.

29:42So big insight, got great early traction on that. Obviously, everyone else has copied it now, so they're pushing their way through in a much more crowded space. And A, I think, can you pull that off in a standalone? You know, you hope they can. B, as you point out. It always seems to me that you have the app back against Google and there's a bunch of people you should be partnering with You know, airtales one but you you can imagine other partners where they too want a part of that Google money Roy, what is it like in three years time? Why is proplice to you then hell? I don't know but you look there's a bunch of obvious players Apple being one of them and the other things But I think the big wild card and the reason this kind of pontification is hard is the whole FTC process is just so painful now Because this is not one to your point.

30:27Well, I don't know. Is this one of those where the acquirer could say, all I want is the engineers and leave the empty husk? I doubt it because to some extent, you're getting the app, the users, the kind of roadmap. So I don't think that's that kind of thing. So any acquisition is at the mercy of the FTC, which as we've seen is beyond weird even now. I don't know how to factor that in. In the absence of that, you've got to believe that there's any one of a number of players who want to be relevant in the space. It could be Apple. Well, could you be Microsoft who said they want to do something here?

30:57That would have been my gut in the absence of government regulation. It's interesting. I don't know, but I just ran a quick experiment where here I went to Pplexity, Chatchy BT and Claude and I asked it a basic question, tell me about Saster and where it's going. That's a personal question to me, right? Pplexity was much better. Chatchy BT, which I'm not a fan of for this use case, I don't think it's that good, got stuff wrong, and Claude blabbered on and on, but actually it had to pause and do web research, which perplexity didn't have to do. So from a user experience, it's okay, but perplexity won.

31:32So, and I don't know how important that use case is, and perplexity is a broad platform now, as Harry knows, right? I mean, we've got comm, we've got all this thing. But this original idea of building a better usable search for this, it's much better. You know, chatchub is so broad, this is the interface to all of knowledge. I don't think it makes the best images. I can't use it for images, I use Reave, I can't use it for a lot of things that it does, but it's not the best at. But perplexity just crushed this question. This is a real world thing that's important to me. Tell me about Sastron where it's going.

32:02It got it right. It got the events right. It's at AI first transformation, expansion of content and format, global community branding, stronger networking. ChatGbD got it wrong. It talks about what have we been doing since COVID were doing hybrid events like Hoppin. I mean, ChatGbD wake up. What year are you in? What is someone that doesn't own their LLMs? right? I just, I can't, I'm not, I just at 18 billion, I don't know the answer to the question, right? I just fell more in love with perplexity on this. I fell more in love with perplexity one. It won the bakeoff. It's always funny when we, when we talk about these things that don't own the LLM's, we all get terrified.

32:36Oh my god, you don't own your LLM. And then when we talk about the LLM's, people are like, oh my god, maybe it'll be a commodity. The vibe coding thing shows it is a commodity because I can use an 1 minus 1 model that is better than the current one. Yes, that's a use case if we debate is it a commodity? I just lived it for 80 hours straight with Celsius and no sleep Waking up it with bad dreams the other night to see that I can actually do better with last year's model than this year's Let me make it explicit that I don't know the answer this question Do you think someone like cursor can develop a model quickly enough to be able to replace what they're getting from a chopic?

33:10Yes, you do you do think they can they know they have enough data They have enough expertise. Yeah, they've got enough money to hire the people to build the models and the models will be verticalized and specialized and so you won't need that much data that anthropic have elected, but they've already got a huge amount of that already. So I think while anthropic won't cut them off at the knees like he wisely said, they have six to nine months to build out their own verticalized models, which will probably be 90 % as good. And in a year, they'll be 100 % as good. Yeah, maybe. That's what I would have.

33:40I believe you're smarter than me, But I'm gonna say after my blurry eye time, I just don't know. We're gonna pivot away a little bit from just the AI Central, which is the other big news that we touched on before in another show was the Figma IPO. I was really shocked by this, guys. We were all really impressed by their numbers. When we look at their numbers today, 46 % year on year, 28 % FCF margins, it's a great business, they've done very well. Fully diluted, that makes about $16 billion price. How did we think about that when we saw that news? I see. So Figma dominated a category. The numbers we've never seen before in classics off or close to it.

34:20Not close to it. Is worth less than the last perplexity round? Is that what you said? Yeah. My only thing that's the comparison. And we could talk about why it's not the comparison. Then we have a long discussion on public versus private. But let's just take the question right on its head. I wouldn't worry about it, Harry. That's indicative pricing. This is how they do IPOs and this is why sometimes money gets left on the table. Every time you sit there getting pitch for an IPO, the bankers will say, start low, get people to the meeting, build up the man, we'll walk it up. That's the story you get.

34:52And to some extent, I get it. It's not like they're looking for one person, which is what you're doing a private deal. You're looking to assemble a book of business and the way you do it is you put something on the table that's attractive. And you are at 14 times NTM or 16 times NTM when I looked out it's got better growth than all but one or two public companies And it feels yeah, it's at the high end of revenue multiples But growth adjust that it feels very cheap here But what does it do it gets everyone in the door? It gets them in to look at the read the prospectus come to the meeting If they build up the demand my guess is they walk it up You can walk it up a certain amount before you we file and then above a certain amount you have to we file a higher number So I look at this and I go this is the classic Goldman Sachs Morgan Stanley you get them in walk it up I don't think it'll price that and I definitely don't think it will trade out that Rory how much can they walk it up 20 does it amount you can walk it up and then above a certain amount you have to Refund which is not a big deal.

35:48It's just an extra day or two I do think one of the reasons that you're Mr. Gurley is so right that you do leave money on the table is what happens is anchoring takes place. And this is the negative one. You start low. And even without any nefarious investment banker, you know, shenanigans, you ever has been brought in by the attractive low price and then the demand bills and you can walk it up. But it's hard to maximize. So you'll be in this weird situation where maybe you walk it up, maybe you refile and raise the range. But just because you started at that price point per share, you probably want to extract the last dollar and you'll, you leave a pop in the table, you'll walk it up 20, 25%, but then it'll price and then day one, it'll pop 30 % from there and then we'll all have the discussion on how much money we'll have in the table.

36:32And I think that's the unfortunate nature of the process. Interestingly, if you weren't raising money, primary capital, and you were just doing a direct listing, you wouldn't have to put up with any of this rubbish, and it'd be interesting to see where we'd price that. If you're just kind of matching buyers and sellers and pushing it out the door without raising any capital, it might be a very different story. I get you in terms of building the buy -book, building the demand, making people come to the table. The other thing that was less typical about it was how much shares they indicated they were going to be selling on the sell side, both from the founder and from the venture capitalist.

37:06Dylan cashing out 60 to 100 million fine, but it's like double the normal allocation that's sold. Is that relevant? How did you think about that? I don't think it matters that much. I mean, I think look, it's one thing when we used to have these IPOs or if you know, a company don't have 70 million dollars, it's been around six or seven years, barely probably. These guys have done their time. They nearly got 20 billion bucks. I'm sure they all made mental models on 20 billion dollars. Now you're coming to the IPO, you know, two or three years later. It's a relatively small IPO of primary shares.

37:39I think the only raising around 6 % primary share solution. One of the problems on the IPOs, you have to come up with a use of proceeds. They're profitable, they have a lot of cash. There's not a lot of these things to do with the money. So my guess is there were being fairly restrictive on primary shares and then the bankers wine and say you need a bigger float and part of what happened here is Evan said we'll do some secondary. I think we'll long pass the stage where the secondary is signaling anything and if anything my guess will be that the secondary sellers will look back on their price two days later when it's up 30 % and go, ooh, that hurts a little.

38:13I mean, for example, on the circle IPO, whether it was a big slug of secondary, those people are looking at the sun, oh my God, it's all a hundred million bucks and it would have been seven hundred million dollars two weeks later. That hurts. So it kind of cuts both ways. I mean, there's this implied statement you are making secondaries bad. But in fact, sometimes secondary can be a real cost to the Salah, not the buyer. That's an amazing story, which is Calpus bought some of Yale's. I love that. Ventualications. And then in that Ventualication was surplised, which wasn't obviously priced reflectively of where it is in market today.

38:47And it's like a 20 % immediate bump for Calpus, given where circles priced. I love it. I love it when in a secondary, like the person that sells makes a big mistake. I love that. When an LP goes out and sells a winning fund on the secondary, I'm not into that, man. And like, I'm not into it, Harry. Would you sell like almost a 5x fund on the secondary market without even telling the founders? Would you do that? Sorry, I got a little distracted. It's my vibe coding, Tendet. You can't hold anything against me after Tendet is a vibe coding. Yeah, look, this is one where, you know, the sale looks transacted because they had cash needs and I think it makes a ton of sense given all we've discussed, why don't diamonds and, yeah, the buyer did well.

39:23The core lesson here is how little you know, right? The amount of variability in venture assets, It's very different, for example, even in PE assets. You can literally be wrong by a 6x. To be fair to Yale, they didn't know, but the sellers on the board who sold didn't know was gonna pop either. In other words, nobody knows shit to a rounding out. Cause let's be frank, if I was sitting on that board and all the people who did opted to sell some shares, very wisely, very potentially, none of them would have sold if they'd known that a week later, those shares that they sold would be up 7x, but you just don't know.

39:56It's a stunning reminder of the massing them, the massive amount of on not even with just all uncertainty we have. You know, Roy, just thinking about what you said, thinking back to the Figma point, which is obvious, but I missed it. Thank you, which is the float so small, they're doing the smallest IPO you can do to still IPO. That's what's happening. They're profitable. They've got, I forget a couple billion in the bank. The last thing they knew is, need to do is dilute everybody, right? Isn't this a Bill Gurley case study where they should direct lists? It's enough of a brand. It's a hot enough company.

40:25Why do they take the dilution? in the headache, if you do a direct listing, there's usually no lockup, right? Everyone can sell anything they want. And just to remind you of indirect listing, you can sell shares either primary or secondally shares. You just literally say one day, a couple of your bankers will say, we now have public buyers and sellers were matching the price and we declared the day one price to be $124 and a way you go. I agree, it's actually one of the few companies that could have done it. It's profitable. So it's not sitting there. I mean, one of the reasons you don't do a direct listing is how do you need the capital?

40:59They don't. All you have this existential dread of screwing up your big debut. I'm loving the bet that the people at Figma haven't gone through what they went through with Adobe. They ain't scared anymore. There's nothing that can happen to the NIP or it's going to make their head hurt. So yes, this is a company that actually could have pulled off a direct listing. I don't know why they did it. Maybe they just decided no more drama. Thank you. Do a small sale and get it done. But yes, this is one of the few companies that comfortably could have done a direct listing story. I mean, canva should do one, right?

41:29If it ever IPOs, it should do a direct listing, right? It's funny, your point. This is the girly thing. If girly's been lashing at how inefficient IPOs are since many, many, many years, right? But I'll never resonate with me until recently, because as a founder, you just want to get a fucking done going to your point. There are times as a founder where delusion is there, you hate delusion, and then there are moments in life, and I think it's the seed and the IPO where you don't care. No founder cares unless you're in a hot -come -any -why -see. If you're a normal founder, you can barely raise around.

41:59You're like, I'm going to optimize around 18 .6. Only at YC do they do this. No one else says a founder does this. And you just want to get the 6 % dilution. Yeah, it's too much. But God, I got to go public. This is so stressful, right? You couldn't have led me nicer into my next topic, though, which is, I disagree with you. Seed founder's care intensely. The 5 on 50s, the 10 on 100s that we see at seeds, because they're being offered by the multi -stage funds, because their cost of capital is so much lower, it's their entry ticket to the club before they buy the table. And that led Rob Goat next for you to write a piece, which many people picked up on, which I'm summarizing very, very badly, but essentially saying that 90 % of seed funds are cooked, fighting the mega platforms, YC, it's pretty much impossible for this generation of seed funds.

42:46because I wanted to hear your thoughts on this because it did take a light in the ecosystem. It's a little dramatic, right? As someone who's just been through some drama did not intentionally, but it's a little dramatic. I would, as someone who's done okay, you know, maybe not a generational seed investor, but he's 10X lifetime with a bunch of billion dollar exits with a decent brand, I agree. Specifically, what do you agree with? I think this, whatever, this low delusion $50 million seed competing with a multi -stage fund. As a seed fund, you can do some of those deals to put them on your website, but you have to hunt.

43:20You either have to hunt ultra early. The bold start vibe. There's a point to what he's saying. You have to hunt so early or create your own accelerator, do HFO or do whatever that it doesn't matter because you're hunting earlier than everybody else. Or you got to, I know this is trite, you got to hunt where they're not hunting. You got to hunt where they're not hunting. Because even if you win that deal, as I've seen, even if you beat Andreessen, and Andreessen is offering 50, and you say, listen, the best I can do is 30. And I've done this multiple times because 30 is the highest price I pay.

43:53It's on my website. So there's multiple deals I've done where the price has been 30. Owner, we've talked about in others, they're all 30 because I'm honest like, and they'll do it sometimes, but there's a limit to that. Even if it's the investor they want, there's a limit, right? Jason, if I was your partner, I would legitimately push back on that and say, Ripling seed was done at 35. And I think it was Keith's Reboy that didn't do it when Gary Tann did, because Keith wouldn't pay more than 25 and Gary was willing to pay 35. Saying an arbitrary number like 30. It's not arbitrary, though, that's the difference.

44:25Okay, but 35 versus 30 makes no difference. I'd wish I had invested in Ripling and I did no Parker then, and I would have done it at 35, because if you know somebody or there's a reason, of course you make, you do, right? But raw, I think Rob's point was in general. Fun construction still matters, okay, for the most part. Unless you have a strategy where it doesn't matter. Unless it's an app just absolute return, ownership doesn't matter. I do believe in that. I do believe in that. But I'm not in that category. I'm in the category where fun construction matters. And you should make exceptions, maybe even on every deal, but you have to come up with a framework where on a spreadsheet it still makes sense at the end of the day.

45:00And so for me personally, when I make an exception, It's an asterisk. What I tell myself when I make an exception is Jason the next deal you can't like I got to go out and find the one that counts and that's how I keep my sanity when I make an exception It's like okay, this one wasn't quite your model, but it's okay, but go find one that is It's like it died. I had chocolate cake today. I'll starve tomorrow. I got it a little bit. Yeah, and it's worth it We went off. I thought it was a great essay, right? Let's start with that right first comment really great I'm going to say a couple things. One is the TLDR Harry is for your summary via a combination of why a commonator and the full stack firms, the average seed firm is cooked.

45:41That's as you said, the summary of it. Let's get real here. As a smart seed for an investor, I don't think that's the way the second chapter of the book is going to end because no one writes an essay that says, I'm screwed, I'm going home. And in the last paragraph, basically said, there are things you can do, see next week. And I'm really looking forward to the second essay. So a more honest summary, forward -looking summary of that essay is, you're cocked if you just do the same thing. That was my take. And next week he's going to tell you his strategy, right? And I 100 % agreed with the take.

46:12I mean, what he basically said was, you know, plus or minus, why a combinator has a market share of 20 % of the seed business and has a structural economic advantage in making those companies. It's never going to go to 100 % because those founders who do why a combinator and then a lot of money, you, you, you, you don't need to, but it's a blaring product and it's taken plus or minus 20 % market share. And then on top of that, you have a bunch of full stack, call it what you want, we call them conglomerates, but full stack firms, for whom seed is not an independent adjacent has to live and die on his seed returns.

46:44For those guys, the seed returns are blended in a much bigger fund where it's all about access and power law distribution will come back to that. So those guys are not entirely economic act was at that point. And his point is the combination of those two players means at best the seed game is 30 35 % harder than it was 8 10 years ago. It's entirely correct. It was a really it was just really clear But the job's always been hard though by the same totally that's the only concede in the article That's the only concede but you write that but I think it's always been hard But you know, you have to say to yourself like you did like if you have been successful under 35 % harder now Now, it's a sobering fact.

47:25I mean, I read it and I thought it was a sobering fact. It is a sobering fact. It is a day -to -day, the ecosystem. But I feel just as sober about the challenges in venture right now at our stage. It's hard everywhere because of these dynamics. I always actually think back to a brilliant statement that Dave Clark from VanCap and LP made me on a show. He said, we look at venture fund sizes today and we judge them on venture outcomes of today. And that's wrong. We should judge the venture fund sizes today on the outcome sizes of 10 years time. In 10 years time, we could have $10 trillion of companies with Microsoft and Nvidia, you know, cursor being a $28 billion company with a billion in revenue.

48:02Absolute joke five years ago, it was never possible. And so fundamentally, I get what you're saying, Jason, but I'm also just again pushing back, and going, well, shit, I'm in poolside, where I've got a 250K check. In two years, it was more to $5 billion. dollars. That never happened, Rory, in the first 20 years of your career. No offense, just because of the time. You're right. And honestly, when I look back, this is also where you get a lift adventure. When I started investing in 2013, 2014, nothing could be worth more than a billion. And that's why I had Insanex, like break the mold acts because it turned out not to be true.

48:40And now I'm looking at like my 2017 2018 vintage, which is pre -AI. But I got the benefit of high ownership and taller higher but tolerable pricing. So now I've got multiple fun returners in that fund that I couldn't get today, right? But it's complicated because like you either get a benefit of that wind or you get crushed by it, the change, right? Because the game is not the same when you achieve liquidity as when you start the game. And I've benefited twice and going to this point now I feel like hey maybe I'll get crushed by it. We might go the other way today, right? And we got crushed in 2021 by the changes, didn't we?

49:14They're very few Most VCs are not thrilled with their 2021 funds, are they? I was walking with one saying I said this, and my biggest last non -21 is twofold, actually. One, I just wish I'd sat on my hands and done nothing. Play the game on the field as a bullshit thing to say. It's not true. Sometimes you don't want to play the game at all. And two, temporal diversification is always right. Yes. You never want to blow your fund in 18 months. We were lucky. We did three and a half years. We're saved because of the lost. I don't believe in the temporal, but keep going. It doesn't even make any sense to me.

49:45On paper, it's totally logical. On paper, you'll look at these advantages and you'll be like, the LPs are just giving everybody a mulligan on their 2021 fund, right? Especially growth guys. We'll give you a pass on it. But I've never understood this logic ever, because great founders are born every week. I just don't get it. It makes no sense to me. It's your fault and my fault. Listen, I set out the game, Harry, as you probably saw indirectly, right? But I still screwed up. I still made my worst investment ever in the granted. it was a third check, not a first check, so it's a different dynamic.

50:14But I was too supportive of Portfail companies in 2021. That was my error, right? It wasn't first checks. It was third checks. But there's great companies born every year. What excuse do we have of VCs to not find a great founder once a year? I love you guys, but we packed so much things. I'm still on two thoughts to go on Rob Gow. I'm now trying to come temple. I'm kind of backing into all these thoughts. But let me try. Temple diversification. I think you guys are arguing over in the sense of temporal diversification would say that those founders born all the time I'm not sure that those two points on contradiction.

50:49I think temporal diversification You're contradictory to how because you said you said you The base version the base version of temporal diversification is you can't you can't make the sentence We should sit on our hands and then make the sentence to Paul diversification I think a sensible, a roughly sensible base case statement is, as an early stage investor, you should aim to be roughly consistent by year. You know, you shouldn't get carried away in the boom years and you shouldn't get too depressed in the bare years because what's happening now is not nearly as important as what will happen in 10 years from now.

51:23So a consistent steady pace is probably the base case assumption unless you have an ability unless you have some information about market timing over and above that. which I would regard, and that to me is the definition of temporal diversification, which you did. You took three years to take your fund out. We've taken three years on every fund since 2010. The standard of genius is just that you do well through the same level of deals per year, right? Are we in sync on that? Well, I mean, I don't think you're sitting on your hands because you don't want to play the game on the field and time diversification are at odds.

51:52You can be doing both at set. Time diversification is I spread out the expenditure of my fund across a set number of years, and that is more, I won't have a longer period, that aligns to sitting on your hands. Yeah, I think it's a cop out though, is my learning. Having done this, done it myself. I criticize myself for that, for using it as an excuse. If you are an asked -year investor, once a month, you should meet a founder that could return your fund, because you can't do all the deals, because you've got to do one a year, right? And so, if you don't meet eight or ten of these a year, how are you going to make money?

52:25How many times do you both think you meet a founder that could Bretagne fund. If I'm lucky, the highest ratio in my whole career is one a month, one meeting a month with worth it. All the rest was a waste of time. Not that isn't good, but can return your fund. It's a narrow box. It's tied to fund size. It's a less than that. It's a once every six months. True. My highest velocity, when I started, I met everybody in the industry because it was small, right? So it was once a month. Now I would say I'm lucky if it's once a quarter, to your point, right? If I'm lucky, it's one. And what it is, half the time it doesn't fit, But the check size is too small, the timing's wrong, it's just off, right?

53:00So do you force it and make the exception or do you push on to fit your model? Is what's hard when you meet? Even when you do meet them, it doesn't always fit, does it? You have a lot of flexibility in your fund right now, Harry. But it still isn't, all the deals aren't perfect, are they? These 100K checks aren't perfect. So a hard -nosed comment, when do you meet a founder that would return the fund? I always say this since I was grim. I think when you meet a company that could return the fund. And I'm pushing against that only because there's an implied statement that you can assess humans and their potential.

53:29And I think human potential is very important, but unless it's linked to an opportunity, I think it's harder for me to assess that. Yeah, I am very much the ulcer -quire statement. It is really market first. So I'm actually making a new one, which is that I think even how often do I meet an investment opportunity doing a market, an opportunity that can return to funds. So that's the first comment. On that, I'm just trying to do the math here. You're probably, as a firm, going to see that at most, where our fun model says you want to return at least half to find in a great deal. You're probably going to see that at most, if you're lucky, 10, 12 times a year, or when you're going to pick maybe, the stunning thing is you see about 7 to 10 more good deals for everyone deal you do.

54:12Access is really important, deal for us really important, but it's always stunning and sobering to realize how often you meet a really great company and don't do the deal. My mental rule of thumb is if you meet 10 great companies, you probably will be lucky enough to do one or two. So and if you need to do one or two great deals a year, you better be meeting 10 good companies a year, other great companies a year, I should say, otherwise the master's not going to work because no one has a perfect stocking picking percentage, no one has a perfect winning percentage. One of the things I will say is, and it's kind of guessing the therapeutic speak is way back when I started out the 90s and keep portfolio regret is the psychological price you have to pay for being in the game because it's literally the emotional tax you pay for being in good deal flow because if you're not seeing 10 great deals you're probably not going to do one great deal which means the psychological tax for doing one great deal is you pass on nine deals or you don't win them that's when keeps you waking night if you're not seeing that percentage of the great deals then you're definitely in trouble so you just got to be willing to live with that There's so much transparency in venture versus when I started, which is wonderful.

55:13Harry, you've contributed a lot. It's really to say it's different than when I started, it would be the greatest understatement of the year. There was no transparency when I started. All VCs colluded. In my first startup, I would go to a VC pitch and I'd go to the next one and they'd already talked 100 % of the time. They picked up the phone. Hey, I heard your meeting, Rory, I heard your meeting Harry. What do you think? What price do you want it? And I'd walk in and they'd already negotiated the deal down when I got to the second VC meeting. Okay, the world is so much more transparent and better today.

55:39To founders, there's a lot of things that don't make sense to founders. And one of them is like how few times VCs see a deal they want to do that works for them, right? Founders think this happens every day. And listen, there's a subset of VC which are like farming YC every quarter, I'm going to do a third of the batch, okay? And they have a certain strategy and they are seeing deals they want to do because of that model constantly, right? But when you get even just a little later to the late seed A and B and you talk to most VCs that are writing bigger checks once a month to your point, Harry, for all of it, like you're lucky to see that one where you run down the street once a month, where you grab the founder by the caller and say, come back to the office, we're signing the term sheet today, right?

56:24And if you haven't done that move yourself in venture, you've watched it across your phone. And this is a classic Sequoia move to sit in the lobby of your office until the deal is done, right? And it's because you don't even, you don't see that every afternoon. This is the weird thing founders don't get. Well, why is the VCs styling? Why have I been ghosted? Why didn't I, like, least understand what's happening is like you're lucky to see one a quarter that works, that were the two by two works out, right? You disagree, Harry? No, I agree. I'm sorry, Rory, you getting your ass handed to you at A by the multi -stage funds.

56:57I went for this business, went from zero to six in a year. Good business, not an AI business. Good business, great founders. It started at 30 on 300, ended up at like 50 on 500, with everyone in that dog coming in. And of course we lost it, and one we wouldn't bed 500, but I was just like, what a market. Are you getting your ass handed to you by these players in the same way? I think to some extent, yes. I think it's widely competitive. And I think that's why I like it. Sorry, Nation, you're up. Just understand Harry's story, then I wanna hear your brother. Is that just because it's a multi -stage fund that even at 500, it's a bet on a bigger outcome.

57:35Is that the story or is it just froth? It's times the multi stage point of they just wanted to deploy 100 and 200 and 300. Yeah, and if it works out of five billion, then they've leaned in on the position. Is that the bet they're making at 500? Yeah. So how do you compete as the, just to frame it, just to understand it? Yeah, first of all, yes, I totally agree. It's incredibly competitive. So there's a lot of different things and it really is the same web, go essay, just extend it up. My bigger hot stepping back is almost everything about a big fund is better for the entrepreneur. And the only counter -vailing trend is if in the end a big fund doesn't make acceptable returns.

58:14Then the LPs at some point will withdraw the money from the big fund. But until that happens, almost everything about a big fund is good for the entrepreneur. Let me tell you what I mean. One big fund you do more deals you have 30 deals you have more news It's more exciting to be in a portfolio with 30 names than 10 right in the last year You have more news flow you have more good things happen because even if you're just a freaking index If you do 30 deals a year and we all end up at roughly the same picking ratio And we saw that analysis you know the benchmark versus Andreessen the picking ratio is less but the volume is more You end up with a constant flow of good news my big at heart has been this the walls of capital give a lot of advantages to those funds in terms of winning deals because they can pay more because they have the implied will stuff more money in later.

59:01It's all an option. They can pay more because they just have more money and they may as well just at some level want to use it up. And the arguments against are very second order. You like saying, hey, but this junior partner, this big firm might not be there. And you know, the truth is someone who's 24 doesn't factor that in. These walls are capital. It's quite a powerful force. And one of two things will be true 10 years from now, but it actually won't matter a damn to me. Either a, not only are they powerful, but they're also profitable, in which case that's where the industry will go. Or the second outcome is they're powerful, but not as profitable, in which case that capital war will be seeded over a long period of time.

59:38But both of those are well outside the event horizon of me making money in the next five years. So back to the thing, I'm just like Rob Gow, one stage raider. You've got to figure out a strategy in the context where the obvious consensus bet is going to be done at a price, the public account of Ford, and done by a fund who just has more to talk about than you, because using 10 billion of LP dollars, they've bought news up and down the stack. That's where you're playing right now, and you have to be better across the board. It is worth it to buy news, you're right. I mean, it seems silly. You shouldn't defund your whole $10 billion fund for news, but deploying 500 million I mean, I bet to keep in the flow.

1:00:17It's like doing a hundred -k check in a hot AA company. It's the same thing. It's the exact same thing. I'm going to defend it. It's even worse. Even if you're not doing it to avoid this, it is not a quote strategy, just by having that much money, you make news. I mean, this is, I give my all to do it. That's reasonable. We want to be powerful. If you have a shift ton of money in America, you're powerful. Powerful is not the same as good, but it's pretty big help to be good. It helps to be at the top of every list. like every PR does matter even today. Can I be vested in even talking to LPs and like, will this model work?

1:00:49And I'm like, let me clear, the only person who has an incentive to figure out if this model will work is you, Mr. LP Investor. If I'm an entrepreneur and some big fund is willing to give me 50 on 250, I don't care that the seven other deals they didn't work are subpar returns. Then I mentioned I got 50 at 250. I'm happy. The entrepreneur doesn't want to call time out here, right? The ultimate fate of this market will be a predicate of how much money those funds make and I'm not going to spend it on that I'm so sorry I just disagree with with you completely which is like, you know fundamentally entrepreneurs do care if you have 30 companies Because they know that they're not going to get much time from you and Rory they really value your wisdom What do they do?

1:01:29No, they do I absolutely Twitter it's really funny It's not it's not because I get that I get the emails and tweets about you So it's not one and then two like they do care that you've I agree. You got a load of dogs because then they're going, will he still be there? His portfolio is shit. And if he's not there, am I going to get someone else who's crap? And you know what I've heard horror stories about? That dickhead that turns up to my board who never did the investment and I don't like him. Oh God. And then I also have signaling risk as well because now I've not only got a dickhead on my board, not Rory.

1:02:04I've got the real risk of a they're going to run another check. All those things are factors, but I'm just saying the competition from that money is real and meaningful. And my big heart is, I mean, look, you've just got to be there quicker. You've got to be more focused on the things you want to do to some extent. You got to, because the only thing that's happened right now is, and I think again, Rob did a nice job on this. It's like consensus bet, 2000, 2010, we were happily doing SaaS. There's a bunch of people doing crypto. There's a bunch of people doing consumer. There was a bunch of that.

1:02:34It was all spread out. Now, the consensus bet is enterprise AI. The wall of money is coming in here. So once something emerges and once the numbers make it, my bigger highs is once the numbers make it obvious that something's working, pricing is going to go to the point where you're pricing in that 2X best case. So you have to get there before it's obvious. It's just that simple. You either have to have markets that's not obvious or companies before they fully emerge. Roy, do you think I'm so sorry to be personal and blunt on a show, but like you're doing enterprise in Silicon Valley at Series A.

1:03:07Do you think you're doing that? When we succeed, yes, and you're right, some of them you kind of go all people haven't bought into this market. It's a case by case basis, but I mean, you're exactly right. There are a large number of them where you go, okay, I figured it out about the same time as everyone else. And it's, you know, a 10 -term sheet, just a fuck. Your win rate goes, I mean, I look at a win rate, it obviously has gone down for where it would have been over the last 10 years just because you know that's what happens right what would you say your win rate is 50 to 60 60 percent ish you know down from before it's a little like win rate you know when you ask a sales guy's what's your win rate and what really happens is a Jason is laughing as a former salesman you know what happens is they channel out all the shit that's not gonna close and you can tell the vibes when it's not gonna close but it's down probably 20 or 30 percent from where it would have been probably five years ago.

1:03:58And you just feel that. And you know, you're up against every excellent firm. And sometimes you win, and quite a lot of times you lose. With Conversity, if you find something just at the cost of a product market fit before it's obvious, then you win, where it can go right up and you can get yeah, much better pricing. It's just the market for consensus is fully priced in and fully discovered. Yeah, you're also your point. I'm a bear state, didn't fully reflect on until you made it and it's obvious. The D specialization eventure makes it stressful. Now, in every category that breaks out, everyone's competing, right?

1:04:28There used to be crypto specialists, there used to be everything, and it's good, but it does add to the stress. When you're instead of competing with a subset of ENCHER, you're competing with everyone in the industry, good for founders, probably, but adds to the stress, to Harry's point. Given the discussion that we're having in the next three years or five years, will we have less, more, or the same number of seed funds that we have today? You don't need to think the answer is less half of everybody's got to die You're seeing spin -offs like never before, right? Because I mean I don't disagree with you Here's just my where I see it.

1:05:03Okay. I mean raising a seed fund in 2021 made note I mean literally folks that had never had to mark up let alone an exit or able to raise an eight -figure fund That will never happen again. That was a weird time. Okay It's happening today, but where it happens today, they're folks that quickly got into hot deals. Okay, so there So those funds are all gonna die. Folks that raised at 1X lifetime or 0X, they're all gonna die, right? And all the LPs I have, which are fewer than yours, but some overlap with Harry, they're all doing very few new emerging managers, right? So if you view it myopically, you can say that's the combination of the two means it's got to be half as be generous, right?

1:05:41But I don't know, man, there's so much greed, there's so much money to be made today that if you have a hot hand in venture, the LPs are gonna give it to you. So I just think there's so much money, But Jason, I think you're coming on the hot hand to spot on. If you caught have a hot hand, you're gonna get a lot of money. But the truth is, in a world of fewer bigger winners, less people definitely have a hot hand. But I don't think so because at bigger firms, eight people get credit for the deal. And the guy that actually did it at 20 VC and get bring it to Harry, that guy's gonna get his own fund.

1:06:11There's an endless, for every great deal we have, I think there's a new seed fund, for every great exit we have. And there are more of these big exits, right? And stick there's more of it. I think if you shit, you're very great. I give you shit. Yeah, I give you shit. And you see fund, but as you correctly point out half an hour ago, there's only a small number of great deals. Yeah. This is the real insight is if you can go public at 50 million, 200 companies are going to go public a year, which is what happened in 1990. If you can go public at 150, 100 companies are going to go public with what happened in 2021.

1:06:41And if you can only go public at 350, maybe 30 companies are going to go public. Yeah. where we're are, there's going to be fewer winners. And the one thing in the end you need to stay in business is winners. There is less of the thing that gets people money. The people who have those winners will have bigger winners and will get more of them, I get more money as a result, but there will be less of them. No, I can't argue with the math. I guess my meta point in here, you're the boss. We can move on, but there's a lot of things that, especially folks that have been in venture for a while, I want to say with a lot of thought and, you know, that YC is overpriced and blah, blah, blah, blah, blah.

1:07:14I just think that the idea that seed is gonna really contract, I think we're conflating the fact there's a lot of crappy seed funds. I don't think they're the same. I think we're gonna see a thousand flowers bloom from every decacorn. To be clear, you could argue that them with seed funds has on the amount of seed dollars goes up by 20%. Because yeah, the interest in the category is still there. The signal of success is more concentrated. So the people who have the concentrated success that's gonna be able to raise more. I think you could have the number of firms and 25 % more capital because anyone who has success, it will be big under the raise more money.

1:07:48I hear you, I have one investment that is not IPO'd, okay, that is, only I would say recently hop a very good, okay, that investment where I was acced has already spawned two nine figure funds out of it, two, okay, and this one isn't, this isn't Figma yet, it's already spawned two. So if my one has spawned two nine figure funds, both of whom have raised two funds out of this. Okay, so more than low nine figures, I'm not that great. Like that's not the one time it's ever happened in venture. If that's happening across these hot deals, it's gonna happen repeatedly. We're gonna have a ton of seed funds, right?

1:08:21Even if all the other ones should die. This idea that, oh, whoa is me, I can't raise a third fund. I've never returned any capital. Tough fucking luck, right? But just look at that story that I did. This company is yours from IPO and it's created two new funds, both with multiple funds and nine figures. Like that is a big deal, isn't it? Guys, you can both invest in one seed firm today, which seed firm, June Vaston. Jason's, of course. No, no, no, no, Roy. Not my nor Jason's, very kind. I love the way you went to Jason's and what mine, that's very kind of you, Roy. We work with lots of great seed firms, because we're doing the A.

1:08:55And how many things I'm prepared to contribute to this podcast? What I am not prepared to contribute to this podcast is putting a gun against my head and blowing up my business model. Just like my children, I love them all equally. I love all those. To the answer. Equally, you're not getting me on record on this one big guy. Do you think they care? I'm so, like, I would, like, happily say, like Brian's. I don't think anyone would take offensive. They didn't make the list. Like Brian, like Brian's New Fund, Brian is one of the best investors, I think, of the last decade. And Roger Aaron Bogg from IA is one of the best investors from the last decade.

1:09:27Yeah. I would do anything to be in both of their firms. Well, larger, yes, as a seed investor, but my sense of what Brian is doing is it's actually actively not a seed fund, just to try and be consistent with the question you asked. He is, I mean, what I understand, his pitch is he's going to do serious being beyond and do a portion of his business fund to fund investing in seed funds. So he probably has a very strong opinion on who the best seed funds are. Jason, if Roy's not going to, as he said, to shoot himself in the head or whatever it was, what would yours be? Harry, this honestly, I want to answer your question.

1:09:58And if it was even a, X years ago, I would have, I'd always had an answer. And I would always tell the LPs, right? I'm sure you're asked to and it's like it's the great way they get deal flow right who would you recommend Harry? I just see too many folks When you squint they're chasing the deals when you squint I've seen too many folks when I actually see the numbers They're not what I would have expected. I'm a little hesitant to answer your question because I actually don't feel competent to know Ironically I recommended you in the early days Harry. I recommended some like I got off the ground when creed stop jans from point nine recommended me.

1:10:29We've all benefited from that from that flow. And I've recommended many managers. But if I was asked today by my anchors, I can't answer the question because too many things are not what I thought they were from the outside. I would give the same answer but for a more positive spin. Right. And it says, well, positive. Yeah, not going to be. What things we have done is we've looked up. You want a partner with seed from. So you said yourself, who has the deals you value? And is there someone that over in it? So the about five years ago, we did this exercise. We We have our internal CRM of deals that we rank as hot or high.

1:11:01In other words, marquee deals that we're really interested in. And we ran it against every seed firm. And the bigger how was this? It's not like there's two firms that jump out of you and have most of the great deals you're interested in. It's so distributed. We ended up with a Goldilocks list of 50 or so firms. In each case, I think the highest one, only 6 % of the deals that they were in were things that we throw interesting and enterprise software. So it's a small number of deals that ever has that are good. And that's just the nature of the seed business. So, the genuine answer to you, how are you?

1:11:35It's like, you have people you enjoy working, what you've people you just connect with personally. But the objective facts are there's probably 40 or 50 seed firms that we go, wow, they're really good. They have their shit together. And which of them gets in the good deals? Hell, who knows? And you just got to stay on top of it. This is a scarily efficient competitive business. And the idea as just 20 years ago, I was like, all those two or three people are great. Now you're deluding yourself. There's a couple of hundred type A, widely driven people competing for, you know, vast amounts of money here.

1:12:07You're not going to find that you're the only good soccer player on the field. Sorry, Harry. It ain't like that anymore. It's who's in the specific deal that you are at the specific time. I'm going to ask one final question if we do a quick fire. And that we just have to. is the culture like guys, we promise we never going to politics, okay? And I'm sticking to that. But there's one I'm going to ask, Coldplay concert, astronomer. Just one question, Roy, before you share on me, is astronomer the company better or worse post what happened? Is all PR good PR? I think they're worse off in the sense that they have to do a CEO such, which is old, tricky, and has a one -in -three transfer feeling.

1:12:43So that's the real momentum here, and I've got to believe internally it doesn't feel great. And I'm going to even say something here that's, I saw someone else in Twitter. And even the two people involved in the family, the two people involved, there's been an amount of shouting for it's quite a sad thing really. There's that you start with the humor and then you quickly process to the sad. And then if you're on the board of the company, you process beyond the sad to the what a monstrous pain in the ass. I think you'd no choice but to make the change. Actually, and so now I should come back. Because someone asked me if you're on the board, would you let that person go?

1:13:13and I think the answer I gave reflects on the common question he just asked. I think you had to, not just because of any policy issues, but because as a company, you have to move on beyond it. If you don't, yes, you'll get lots of... But if you left the person in place, then every meeting he took for the next year, you know the overlay in that meeting. There would be a subtext. So I think the company, it didn't help them. Yes, it gave them some notoriety, but it's kind of a... There's a frictional drag and the only way they could put it behind was a CEO replacement and that's a one -in -tree chance of failure.

1:13:47So net net slightly worse off. This is off. I remember when Tiger Woods had that go on be a Tiger program with Accenture that launched literally the week after his, you know, extramarital affair came out. And there was about a day where they thought should they pull it or not. And then I think everyone went home to their spouse and their spouse looked at them and the eye and said, there's not a decision here. You're pulling that ad, dude. I'll do that. Right? And it was gone next day. Everyone recognizes personal tragedy. No one has to be thirsty. It's just too shitty to touch. Move on. It's sad.

1:14:20Move on. Let them pick their lives up. Everyone makes a mistake. Go do something else, but companies are just put it behind quickly and clearly. Okay. We're going to do our cowshy quick five. The cowshy is the performance marketplace. They do the bets and real time events. So at number Number one, will the US Tower of Freight on Canada be at least 35 % on August 1, 2025? Yes, returns you 2 -14, no returns you 144. It's a random number. It depends on what the episode of the reality so requires. 35%, I'm going to go with no, but it's an uninformed opinion. But then, frankly, Evan involved in this issue was uninformed.

1:14:58Why should I be the only one who isn't? I think we're just all at a phase, culturally across borders where we're digging in now. Harvard's digging in, everyone's digging in. So I say it's still there. Good job, boss. We'll open AI release a web browser this year. Yes, only gets you 125. I know it gets you. I'm actually interrupting you, but I'm the one who told you to read the odds. Yes, I think of course they will. It's hard to imagine not the most ambitious company out there not doing something that perplexes doing, other people are doing. Yeah, my God, there'd be yes. Well, listen, the internet sure seems to think the answer is yes, right?

1:15:33I just think that they don't have to, they don't have to rush something here. They can be a fast follower. So it seems 100 % that it's going to happen. But this is a math bet, right? I'll take the note just financially, but I believe it will happen. If this was a gentleman's bet of 50 -50, but I'm going to take, go for the money and just say, they might go back in the oven. I'm with Jason, I think GPT -5, I think Agent Mode, I think Shopping Proatestation. I just don't know if it'll be this year. It's August already. Okay. Talk. Do that. Final one, will XAI release a GROC Mac OS app before end of year?

1:16:11Do you guys use GROC? Yes. As I said, whatever I want to talk like Harry, I talk to GROC. So I shouldn't do I do use GROC. I test it. You know, we're all a little bit twit, sad, twit, or addicts. We need to get over our addiction, but it's hard. So yeah, I do use GROC as part of that. It's not my go -to, but yeah. Jason. Well, first, I think going to last week, I think Rocks wildly underestimated. And I think when Elon says something, he's either upset and I get upset. I get upset. I even get locked in, it turns out when I'm coding, when I'm vibe coding. But when he's not upset and he says something, just like Sam Altman, you should listen, right?

1:16:47So when a couple of weeks ago, he said, you don't need to use Claude code. Just take all your code and stick it in Rock. This is what we do. And we find all our bugs and push to production. He's saying this is developer ready. Interesting. That's what he's saying to the market. Now have they built an IDE? Have they built out all the pieces yet? No. No one on the thread I saw said, hey, Grock is not good enough for that. They just said, we just don't want to throw all our code into a context window. But that says to me this is real on the list. And so having a Mac OS app is like the easy version of that.

1:17:23Like you've got to do that. You've got to have a desktop app. So I'm going to, given that the odds are unknown, I'll put a grand on this one. What on boys, we covered a lot of ground in that. I so appreciate it, Jason, thank you for putting your neck on the line with some of that. You're a star. Love you, genuine me. I was actually vibing. Everyone loves these shows, which makes me incredibly happy. Honestly, the true joy for me, I've built great, great friendships with Rory and Jason in a way that I didn't have before. They are truly special people. I'm so grateful for being able to do the show that you love it I always want to hear your thoughts.

1:17:59Let me know what you think Harry at 20vc .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 project 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.

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1:21:29As always, I so appreciate all your support and stay tuned for a fantastic 20 product tomorrow with Monzo's former CPO Fernando Fanton.