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24:09It's confusing, right? The Captain Obvious theme is that no matter what happens, Chrome ends up being this accidental gem. Chrome was built very strategically in the old days and the desktop focused days to counter, you know, i .e., which it destroyed. And then it's open source. So, you know, Safari and Operating, everything's built on Chromium. They gave away the open source version. They destroyed everything. And then it kind of plateaued like a lot of software did, right? We had plugins, we had cool, we took it for granted. Now it's the Crown Jewel in the age of AI, right? Is the Crown Jewel again?

24:41It's the return of the, it's not just the browser wars. It's the return of the browser being this corpice of software that we forgot about for the better part of a decade only Personal agreed and I can't resist the chrome wasn't built in the day statement But moving right along you right and it's only because for 10 years Google won in the sense that no one else could monetize traffic anything like the dollars they could which is what you know So why bother building of I mean you could have these you know niche browsers but you couldn't build a Himangus business because the only thing you could do with that traffic was monetize it and The only place to monetize it at scale was Google and the interesting thing now to your point Jason is you can Invisit the world where someone monetizes chrome traffic via an ad support and product But there's also you know chat GPT is a The astonishing consumer subscription part what is it 20 million like seven on a million free users 20 30 million paying consumer subscribers I think is the numbers.

25:36That's a very profitable business where the weight limiting constraint looks like your ability to sign up people, which means which is why it's so smart. If you could get a billion people coming through your door and if a billion of them were free users and you have the same conversion rate as chat GPT does, which is a leap obviously, I doubt you would, but any kind of conversion rate is 20 over 70. That's about the 2 % plus on my little under 2 % which is what you see a famous, you know, if you get one or two percent converting into paid users, it's a compelling business. Suddenly Chrome matters.

26:08Not because it got better, not because the browser is uniquely different, but because you can plug it into a machine now that can collect checks. We're not talking about AI for normies. And this sounds incredibly condescending and patronizing, but AI for normal people and normal people is kind of the slow lag gets to adopt. And what I mean by that is for the record, normal people is not patronizing, but of slow lag, which is, so you might want to work. Yeah, I'm willing to be normal, I prefer not to be slow, but keep going, Harry. I'll keep going with this. A great example of that is threads, something that we all deem in our circles to be like, who the fuck uses threads?

26:44Threads is actually a massive success. And what I, the reason I'm going there is because yes, we all think Changi PT is great and a massive hit, and 700 million is amazing. And yes, it is. That's unbelievably incredible and insane. I'm not doing a prior guest and saying it's not. But Gemini is great, actually, and it's getting better and better and better, and they will plug it into the core engine and the Co -distribution channel and actually for AI for normies There's a real chance that they don't lose any market share. You're right for a good slug of the population They were going because an AI answer meets your need on Google and you're done Yeah, Gemini as a model is actually apparently pretty darn good even for coding someone was walking me through so So they're going to have market shape.

27:27They're not going to roll over and die and the social empties will go up. It's simply you've gone from a situation where you're the only game in town to a situation where these other guys are taking a siphon and slug. So it's always better to be a monopolist than an allegopelist, but it's still pretty okay to be an allegopelist. I do want to move to an insanely hot deal, guys, that really in Europe, like it was a talking point for everyone, and eight, and it was done at $3 billion. dollars. And reportedly it was at 40 millionaire, or ending the year at 80, Excel, let the round massive. I think the last round was not too long ago at 300 or so give or take.

28:03It's not a new company. It's a 2019 company. How did you think about this? With Envy, let's start with that, because in fact we had talked to them in about 22 or 23 and you're right, what we clearly underestimated was workflow automation, it's a category pre -AI, it's a category we looked at a lot of players, it's a noisy one, you have all the way from RPA to process mining, to kind of low -code no -cord, and it's big, indigestible mass of things where every solution blurs into the next one, it was just hard to know what's what and therefore hard to build a big compelling business, especially with lots of competition.

28:43And clearly they did a brilliant job of co -attaching to AI because when you go from automating work for us so people it have a deterministic way to actually getting more of the work done using AI, the value prop of your software goes way up. Instead of saying, you know, we're going to automate a little bit of shit. Now we're going to literally do the work and you can get rid of all these people that were doing the boring work. So they did a clear did an excellent job of that and in a space of six, nine months, just massively accelerated and well done them. You know, it just shows you got to stay on top of these things.

29:14Good on the guys, Highland, I think you're up to the last round. Good on them. As I've gone into vibe coding, right, deep, right, I've like reused Zapier so much. I've got to hook stuff up, right, without wanting to code it. And if any, any, any is a more developer version of that. So I'm having a Zapier renaissance. But today, man, with the explosion of applications we're building and the explosion of things we want to connect with the eye, it's like an order of magnitude bigger. Maybe Rory, when you met them, you couldn't predict, right? it was hard to predict the accelerant that would happen and it's probably in the last seven months right from the revenue right and then boom.

29:48You're an act of your heart there are companies that you've tracked for a while that you mentally might be lighting off. You can either decide it's not knowable you bet randomly you can try and track them just based on metric all the most logical thing you sit down you say what areas will the model significantly impact in the next six, 12, 18 months, and one of the companies that could benefit from that. And then the second criteria, you've talked about this before, Jason, it's all very well to say, there were probably 10 related workflow automation type companies, which one of them will get the prize.

30:20I tell you, it always comes down to the founder who gets it the most, gets it the quickest, and just puts everyone in the room and says, no one's leaving till we're shipping, and they'll let them enable version of this. And we're going to get it in for the 20 customers by Friday. Yeah, in retrospect, that was the aha here. They clearly had those elements. And if you tracked it, you'd have made a lot of money. The thing that's really stuck out to me is index. Index and making everyone feel like shit right now. In particular, in Europe, Sequoia and Excel. Excel have to win. Otherwise, to Gap Whidens more and more and more.

30:53And they're one lovable. And now they're winning NA and I think any price. It's a well -priced deal. But they did that Facebook back in the day when they're out of the game. They bid at they bid I think they what do they pay for Facebook the pay for maybe 200 million or something pretty I 100 million free they were insane people said Excel was washed up and they had to bid up this this fledgling social network I'm actually praising them. I'm not saying I'm saying the same thing and look if you pick right no price as well I think I do think there is a retaliatory element from Excel of oh shit We have you and this is a nice stuff You know your European market better than me and maybe because of small and I don't humans are humans so that kind of done it's a bad way to try and make money and it's hard because we're all prone to regret, formal decision about looking back at the decision.

31:43You'd like to think you just make every decision on the basis of is it a good bet or not? I don't know what you think, worried. This is what I was taught. I'm not a growth investor, right? If you're riding one of these checks, you believe it's a winner and you see a clear path to 5x. And you can deploy enough cap, but all you do, the deal in a certain moment in time. So if they believe 5x with delusions a lot, it's got to be worth a $20 billion company, right? Or lovable's got to be 20. They all got to be 20. But if you genuinely believe it and you overpay it and it keeps you in the game and it's for your brand, like, you know, and it's not your whole fund, it might not be worth the bath.

32:16If you genuinely see a 5x, the growth run zone, I'll have to be 10x or 500X, right? That is definitely true. It's wide overpay to get into a good deal where you're not in a space, but it's not insanity if you see your way to 5X, right? It just might not be a 5X fund returner if that investment makes 5X in a growth fund. There's actually two things to unpack there. One is the 5X versus fund returner. You exactly right. Growth investors typically, when they're looking at something, can say a 3 to 5X. And the interesting thing is, and they'll say, and most of the time it's hard to go beyond that.

32:46And then by virtue of the power law, one and every 10 does. It's just like not dissimilar and it's practically similar to seed, but just when they're much bigger, it's harder to envisage, right? But the truth, I mean, I remember a Facebook investor, an early Facebook investor said, you know, they'd bid another deal, they'd last up, and they said they could see a three to five X from here, and obviously they made a hundred times the money. So, yeah, you basically just operate on the power line, some of them turn into amazing, but you want to be able to say your base case is a three to five X. That's totally absolutely, And that's the business they're in.

33:18Now, you went from there half a year, to the half a year, the paragraph into some kind of what we should do. It's a brand that we need to be relevant. At that point, what you're really saying is I don't see it's way to five X, but I'm just going to convince myself to do it because I got to be relevant. And the sad thing is sometimes that might be the right thing to do. When I recoil a game that perhaps run late to the property arms, maybe there are times when you should just do that, but it's just, it feels like I remember when they teach in Catholic school about sin and they'd say you start on little things and then we'll just get worse and worse.

33:48It's in what if you start doing deals not for return does it just get worse and worse forever? So I don't love the I won't make my return but it's good for marketing school of investing. But I also recognize that sometimes you can say I can squint and get a squeak and it will be good and pay sometimes you do what you do. Do you know the funny thing is we have a like YOLO segment of our fund which is like two million or three million whatever. But it's basically we have amazing access because of the shows. And people will give us positions at high prices, but we get into amazing names and it's given for marketing brand.

34:21It's seven Xs a pool right now. No, I make sense. It makes sense. When we did it, we were like, this is total brand. Never expected. Yeah, but then you've been, it's great. And then, but then as you get later into the fun, you're like, well, so what? I got 12 Xs. You'll make, I believe it, right? And then like, but it turns 5 % of the fund is the problem, right? And I think that the other problem with that is the Machiavelli quote, which is, you know, that I've used it before, that circumstances change and people, but people don't. And what works in one market doesn't work in another, right? That same strategy, when you look back in 21, it felt really sickling in 22, 23.

35:00It felt like that wasn't the right strategy. Be more careful work. And then obviously whenever you're componing a boom and you're leaning in, leaning in as the right strategy, and it'll be the right strategy until, you know, pricing turns. This is super narrow niche. It has one small advantage that strategy though thinking back because I accidentally did some of it pre -AI, right? It can get your early DPI in a fund. I accidentally did some of that from my 2017 fund I got about 20 % of it back early from these early exits that had Anomonal large value, right? And it doesn't matter at the end of the day so much But you're gonna hold some of your early your early stuff may take 15, 20, 35, 40 years to get liquid these days.

35:39So it's nice if you can get that early DPI, even if it doesn't matter too much in the long run. Well Jason, this and you and me and you both are fortunate to have horsey breach, you are I think of one of the best of the best and I love them dearly, but they've taught me really that venture is a very challenging asset class unless you take advantage of very small windows of hyper liquidity. And so where I think about this is absolutely aligned to you, I'm leaning in being very cognizant of when to lean out and being very aware that this will fall off a cliff, but I need to time it well. Yeah. I buy that.

36:12As I say, there's one you and seven where you make mostly a money and the one thing you don't want to find is you don't have, you don't want to not have assets to sell when that year comes around. If you want to be a little cynical about venture, right? I do think in your earlier funds, it is like everyone on X talks about DPI, DPI, but you know, you don't want to sell your winners early. Like we, we've had that conversation too many times. And, you know, I had a conversation with Horsley. I had a winner. I had a chance to sell for Norah Billion. And they're like, don't sell it. Don't sell it at all.

36:40It's not enough of a return. But it is nice if you go out to raise your next fund and you've got some DPI, right? So if Harry's little sliver is at 10X, and again, it's 10 or 20 % of the fund and you go out, and it shows that this current fund is making progress versus all markups and no cash, it is cynical, right? Fundraising is just like founder fundraising and for folks for founders that are watching, listen, like you gotta put some points on the board, right? So it's not bad to have to overturn some of your fund at a nominally very high IRR in multiple, even if the absolute number, if you squint and you're like, you know, that was only 11 % of all that together, it's only 11 % of the fund, let alone a one -axe of the fund, right?

37:24I think it helps. It also does amazing things for relationship builds with founders. When I look at a McCool, when I look at a complexity, when I look at amazing business and say, I wanna see me and Harvind chat a lot. Would we chat a lot if I hadn't have put a tiny check into the company? I don't think so, not as much. There's no tie that's enduring. And so I think it actually does outweigh moving on. I do want, are you guys gonna be exceptional on this? And it was nuts, weak in terms of earnings and many respects. I wanna start on data dog. Wow, best in that new ARR quarter in company history, 260 million ARR in the quarter.

38:00initial reaction pretty positive and the stock is down 10 % in today and lower than before results. I just couldn't get my head around this guy's honestly. It seemed great and the market puked. One of the things that when you talk to CEOs of public companies and you should do this thing, other than the obvious, you know, major beat, major miss and we'll talk about one in a second, for all the middling things. If you talk to a lot of CEOs and I remember we used to play this fun game on some of the boards where you'd know your numbers and you wouldn't know the markets reaction to those numbers and you try and speculate and at least half the time you're wrong.

38:38It's actually a very fun game to pay on a public board. You have the earnings call internally, the internal thing, you look at the numbers and you say, okay, the stocks 32, when we announced these numbers up or down and by how much, the error rate is massive. In other words, a perfect information doesn't tell you shit. Other than the obvious, when you miss by 20%, or you beat by 30, it pretty obvious what to happen. But in the middle, it's very hit on this, which is the odd thing. I just offer that as a kind of pre -limit common. I remember watching my CEOs internalize that. So I actually, I stopped worrying about it.

39:11Because remember, you know what you did relative to your budget. So you know how you feel as a board member or a CEO or one on the company. They're comparing your numbers to two things. One, they're internal estimate of what they thought you were going to do, which you've no visibility to. And then even more zanely, the Keynes quote, what they think everyone else thought you were going to do to try and figure out what happens. And if you look at Dana Dog, the stock went up in the aftermarket. In other words, people looked at us and, oh shit, this is good stock up. Next day, it's like, oh, it's not good.

39:41Go down. My bigger heart is, it's like dealing with a deranged madman trying to estimate what the street will do. I spend no time on it. Oddly unknowable. So there's folks that are directly benefiting from the AI boom. They're selling AI products at 8N and others. Then there's folks that are benefiting because AI is exploding. So apparently, OpenAI pays data to act 240 million a year. So what's happening is, and I'll give you a very small example, here and I are both investors in a company called RevenueCat that powers 40 % of all mobile subscriptions, okay? And it is already usage has already doubled this year from one end last year, even though it's not an AI company, neither of these are AI companies.

40:20But revenue cats more extreme, but all the AI guys are using their product. So it's very exciting, but it also has concentration risks because there's, there's only so many of these large players, right? There's pricing pressure and open AI has already said they're going to renegotiate down the data dog deal as they should, right? So there's folks that are exploding not because they're AI, but because of the AI economy, but I'm not sure that's why the, that's why it's up. one of the reasons it's up, but there's also a fragility when you're indirectly benefiting from this. But obviously that's a lot of incremental revenue for data dock.

40:56A $240 million of your customers is high. But the incremental revenue in spend is from AI. If you're a B2B company, you've got to go get AI revenue, because you're not getting it from John Deere and the rest. They're spending the same. In fact, I'll be a little bit... No, you're exactly right. Because that's that up on zooming out from this, right? Is that, I mean, you see the data almost the entire GDP growth is AI CapEx. So if you can coattach, even if you're not AI CapEx, if you're not Nvidia, if you're not, if you can just coattach to the money, you're going to get a pop now, it may not allow, but yeah, the spend is happening there.

41:32That's where all the CapEx is going. So it's literally, I always think of what is the bill of materials to build AI. If I wake up tomorrow morning and said, I want to be safe, super intelligence. I want to build me one of those LLM models. You just make a list of the things you need. You need chips, you need a data setting, you need power, you need some codeos. And then you write, it's all the little things. I need to keep this up and running. I probably need data dog. I need, you know, one of all the other software tools to make it happen. And if you just co -attach to that, it's showing up now.

42:00But I think it's the productivity is not showing up. The revenue is not showing up at the app level, but the cap X is showing up in the GDP numbers it's so big. So you're exactly If you can get your piece of that, then I'd prefer to have it than not. I mean, people are saying, oh, it's a bad $120 million concentrated risk customer. It's a downside better than not having a $120 million customer. Is this a gift or a curse? And forgive me for my naivety, but the concentrated risk of 260, yeah. And if I open out, I continue its trajectory. It'll be 520 in a year's time. And yes, it's a gift. We agree.

42:33I think Bordiff was saying the same thing, how he, which is the people who are worrying about that's why you're getting into the second order derivative thing. The people trying to value the stock, they're not just saying, I mean, if you were the operator, you would be coming into your board and you're saying, we killed at this quarter, we saw in a hundred million dollar AR deal with the most exciting company on the planet, it's freaking amazing. End of conversation. And no one is going to say, oh, I'm really worried that they might kind of reduce the price in two years. That's bad. They'd be like, dude, we're so happy.

43:01And as a board I would be too. You know, Wall Street get, as I say, it has this different role, which is not just guessing what you are now, but guessing, you know, how you're going to be compared to what they thought you were going to be and, you know, that they're paid to second -guest themselves. As I say, my best advice is ignore it. Maybe two years time, you'll be dealing with a renegotiations, but as you point out, maybe you'll be dealing with the fact that open eyes growing so quickly that the contract is doubled and they don't have the engineers to waste. I'm kind of engineering you out, and you just take the check.

43:29We just seeing like, big -ish tech, just win, like just invest in big -ish tech. And what I mean by that is like, app loving, crushed, you know, HubSpot gains, Shopify are ripping, Palantir obviously ripping. These are not Mag 7 quite, they're great companies, they're not like, belong big -ish tech. The whole AI wave is mega. That's true. I mean, I'd say, I think there's maybe two things going on. One is, yeah, the AI wave is mega. And I think definitely penalty of probably data dog, not so much out dog, your HubSpot, and Shopify benefiting from that. But then the second thing is, you know, why do that this whole, oh my god, SaaS is dead thing?

44:07I think what you're saying is, and I think it's correct, is that these markets are big and huge, and if you're the winner and you're public and you've got scale and you execute well, add a little AI, you can defend your position, grow nicely, kick off a ton of cash. I wouldn't like to be a little start up trying to enter the HubSpot space or the Shopify by space. But the death of SaaS has been overdone for the public market winners, which is a very different thing than saying you'd want to invest in, quote, the next Shopify at a million in revenue. No, these guys, they have clear market leadership positions.

44:38They on every case have strong founder CEOs, they have profitability. And yeah, the growth re -acceleration, this quarter has been pretty real across the board. As I said, put Hubsbot if I was to rank them in terms of their AI and Hubsbot and Shopify are in that, yeah, they're using AI but they're not direct beneficiaries and data dog in the middle because they got a big -ass contract from the biggest company in AI. So we're kind of caught that and then obviously Palantir, a white heart in terms of the AI story, they have brilliantly become the way large corporate America implements AI at scale.

45:11It's a beautiful position. Can you guys help me on Palantir? I always look at it and I go, amazing company, but oh my god, look at it, it's so overpriced. And every time I do that, I'm proved wrong. And it goes again. How do you think about that? And legitimately, how would you advise me? I love these shows because I love them for me both. I mean, Jesus, I mean, the growth is friggin' breathtaking. It goes from 12 % growth at about 2 billion revenue in 2023 to almost 45 % growth at 4 billion an year. Good, and this has never happened. Forget about the fuel, right? The secular fuel, the contracts are getting bigger.

45:48record number of 5 million unup contracts. The fact that they are the AI solution for both commercial and military. If I didn't even know how to spell Palantir or what it did, which I think most people didn't even know until 12 months ago, what it did. When you see going from 12 % growth for a public company of billions in revenue in 2023 to almost 50 today, I mean, maybe Rory can go up with an example. I don't think an enterprise software we've ever seen that level of re -acceleration ever. You can either say it's going to decay, like all curves do. Or you can say, good God, this is my 10, you know, everyone in the public markets, they're 10 backers.

46:24That's what my social media is full of. What's your 10 -bagger, Rory? What's your 10 -bagger? And it's, you know, what the chart keeps going. This is unprecedented enterprise software. Across 20 years, about only one in three companies, we accelerate for one year and about one in nine, one in 10, we accelerate for two years. So that's just the data. That's daunting.

46:49Yeah, I can see how you can build a model. Let's say if you go from 12 to 23 to 45, you write the next question. Do you feel in 55 or do you feel in decay at that point in time? And the problem is any exponential curve up can justify almost any valuation. I mean, my gut Harry is your instincts. All right, which is it's an amazing company. Smack in the middle of two huge trends. We're going back to my second. And at the same time, 120 times, revenue plus or minus is probably not sustainable. I mean, I saw the data. It looks like it was a good statistic. Someone says, five years of 40 % to 50 % growth, and then there'll be value about the same in terms of a revenue modulus Google is today.

47:32And you know, you can have two responses to that fact. Part of me says, oh my God, five years where you gotta pull it off, that's a lot. And then you gotta go, it's not crazy. I would be terrified of buying it at that price, But the interesting thing about that calculation was you go, oh yeah, it's the beauty of compounding Five years times 1 .5 you just ended up an amazing place now. I haven't checked that math fully So that's kind of I mean it does feel incredibly lofty at scale I mean does that great Scott McNeely called about trading at 10 times revenues where he just you know walks through how absurd It all is when son was trading at 10 times revenues in 99 and every once in a while you should we read that called because he was totally correct and it went and tears.

48:10So, in 222 tons of revenues is not a sustainable place. But yeah, they got three huge trends on their side. They're the AI solution for large corporates. They are the AI solution for defense, which is having a boom. And they got the administration on their side. Just this last quarter, they closed 843 in US commercial bookings outside of it, up 222%. So help me with the map 222 % at 843 million. I mean, this isn't quite loveable growth, but this is pretty good. And this was 22 % at 843 million. They're commercial division. And you got again step back and give credit to the founders and obviously feel and book.

48:50In 2000, I think it was a 304 with a sense of mission of our 911, built this stuff, then moved into commercial. It was a slum for a while. Some of the early commercial customers weren't wildly successful, but they've ended up now whereby one of the things you think about is when big companies want to do big things with a project like this, it's not the kind of thing you can give to, you know, little SaaS companies just starting out. Big companies need to spend big initiatives with big vendors. And the point is all the other big vendors are old and start like IBM and Accenture. And now you can have these dudes who've been, you know, working for the US government that got the whole forward deployed stake.

49:26I see how it's working because Copa, I mean, I went through the last earnings and actually went through a bunch of the use cases in corporate. And it's all over the place here, supply chain planning, scheduling for an airline. It's a whole bunch of very different stuff. And a single SaaS app couldn't do that. But what they have is a platform that's been around 10 or 15 years. They have another platform they've added around enabling LLMs and take that, take the forward deployed engineers. You can squint and say a lot of its services, but who the hell cares, the margins are 50%. And the reason they can get it is they can look, the CEO or the CFO of a Fortune 100 company in the eye and say, we've done tenidys, you give us the ten million dollars, we'll get this puppy done.

50:10The other two competition is a little staff startup that says we have a hundred thousand dollar product that's way more efficient than Palantir and it'll work, but it'll lead a lot of work and they're like, oh, don't know about that. And the other competition is eccentric saying we're going to build it from scratch. They're just in that sweet spot of they can make the pangel. You can get your AI initiative as the CEO of a large corporate company. You give him $10 million. You got your AI initiative. They'll probably get it done. It's a golden place for the next couple of years. You know what the other crazy thing about Palantir is?

50:39I thought this was fascinating with Alex Carp. So there are a rule of 94 company today, right? Pretty good. So he said, I mean, he's on fire. Just watch his body line. He knows they're going to crush it, right? But he said that when they will be, when they're 10x bigger, so at 40 billion, They'll have 10 % less employees than today and they're already on the trend to that and I think when we there's a meta point I don't you know, maybe maybe needs a few more But I think this has been well thought through and this this is a hint of the future in Palantir right this efficiency level Microsoft has already reached peak employee right Google's already reached peak employee But Alex Carp going on record saying at 40 billion in revenue 10 times we will have 10 % less employees I think it's the journey we're all kind of on, but he's he's out there because he doesn't give a rat's ass What anyone thinks in his farm in Vermont and sandals crushing the numbers, right?

51:31But to me, this is the future of B2B companies. Just trying to get to this massive massive scale with few humans Yeah, I wouldn't pen for it into my model But it doesn't matter because as you point out 10 50 % operating margins today Don't bother getting more efficient just scale So he's not doing it obviously directly for the margins, right? but it's how to structure the company. But this may be where the future is. Like he's just so far ahead, he can make these visions and bets, right? And not be hiding in 7 % growth, you know, as some others. I just thought that's the future. I think this age of these bloated companies is just, and same what you're talking about Shopify.

52:08Shopify is at 1 .3 million in revenue per employee now. And it's re -accelerated. And it's re -accelerated. I don't think it is we can talk about Shopify if you want, But the efficiency at Shopify is not at Palantulas, but it's breathtaking the efficiency. Chobie's ruthless on this. And founders should be too. Founders should be ruthless on this. You don't need half your company and palantir and Shopify are proving it. You don't need half your company. You literally don't need half the people working at your company. You don't need it today. I'm glad that Hall of Fizz isn't listening to this show.

52:37Work harder. Learn your product. Ask yourself, are you actually valuable to your company? Be honest. Not just are you a people person. What do you do in your company where you're irreplaceable? It's not that you're going to get fired or anything. You maybe moved out. Your future is uncertain if you're not irreplaceable. It's just uncertain. You're not getting fired. How are you just getting moved out? Oh, there we go. I might be slightly hot to move me out. Or I feel slight protective layer around me. But you're too much. Yeah, but you're too much. You may not need them for investing or content production in two years.

53:08You may not need anyone else helping you to invest. I was more getting Jason to hire him. This is an interesting question. Do you want your team to feel uncertain? Do I want my team to be scared that they might lose their job? Now, in one hand, forces them to find the irreplaceability of their roles. And it also can make some people uncomfortable, horribly uncomfortable, scare. It's not a nice thing. Yeah. My learning is it doesn't matter anymore. There's so much uncertainty out like we coddled people for since 2020, like since since the middle of 2020. And then we and he called them like, there was no tomorrow until early 2022.

53:43Take three jobs, work two days from home, life is easy. Like take care of yourself, and if you can come to work, but take care of yourself, everybody, Shopify had twice as many employees at the peak as it has today. Shopify, forget about them, twice as many. And Toby was telling everybody to relax, guys, in like 2020. Take it easy, guys, the commerce will come. Now he's frigging ruthless, isn't he? He's ruthless, zucks ruthless, carbs ruthless, And if you think you're gonna win in B2B, if you're not ruthless, you're gonna lose. So I don't think you should scare people. I don't think you should tell people, hey, if you don't step up your jobs over, I actually think that's a data approach.

54:20Just step up and they'll quit. I'll give you a small example if you want this issue. They'll just quit. There's a tool for example that we use. We use 10 AI's now at Taster, up from zero at the start of the year, okay. But what is a niche tool called momentum .io? Okay, it's a cool startup where you should do the next round if you can maybe. and it basically matches up everything, gong, granola, everything so that you have real time insights to everything your sales team's doing. And I tell them that pre -seed, is it good? It's good product. It's a good product. It's not perfect. But here's my point.

54:52Here's what's interesting. It's like a lot of AI products. It's not that any individual components, all that interesting. It's how it synthesizes it, elegant through three AI. But I'll tell you, every company, and I got turned on to it then through Kyle Norton and I brought it into other companies. Every single time it's been brought in, someone on the sales team has quit the first day. Quit every single time they quit the first day, including on our little saster team, someone quit in the day we brought it in. He quit that afternoon because the gig was up. The gig was up. And so that's why Harry, I don't know if it matters whether you prepare the team because there's gonna be so much AI around us, the gig's gonna be up one way or another.

55:29If you're not productive, if you're too busy to get the podcast out this week, if Harry had to do it himself, if you forgot to do the TikToks, the gig's gonna be up across tech, so you don't have to cuddle people or scare them, I think. They're just gonna get a report every day that, you know, you didn't push out enough code of Shopify, you're gonna get pushed out. I'm gonna go back to the scared thing and I've got to think about it a lot, right, as you mentioned it, because it's all funny, how we start off with prepared script, and then you just take a so off script, buddy, and I haven't spent any time thinking about this until you asked about it.

56:01And there's a couple of different categories. I don't think it's great for society if everybody's scared all the time. At the kind of level of, there are jobs where once upon a time I went a manufacturing company, right? At that level, the blue collar jobs are pretty interchangeable. If it doesn't work out in employer A, you can go down the street to employer B. I think it's good that the mass of people don't live in terror, if you know, not be able to put food on the table. There's a whole bunch of jobs where it might work out with this employer, but I can get roughly the same wage from another employer.

56:32So I got to follow the rules and work hard, but I'm not sitting there every day terrified. But what you're talking about, so that's one category. And frankly, most of the people have those kind of jobs. I mean, I don't want my teacher, teach my kids a natural, do we terrified? They should know that if it doesn't work out in this school, they can go somewhere else. That's most jobs. But there's two categories. He made it's only one here is if you're holding down a well -paid to extraordinary well -paid job and in an entrepreneurial, and an entrepreneurial, come here. And let's be If anyone got paid a hundred million over four years of meta, it's extremely well paid.

57:06If you're pulling down those kind of salaries, if you're an entrepreneur company, you should be afraid. But ironically, there's doesn't affect any of those. They say fact is the hundred grandier, more could it be? They say fact is the hundred grandier, STR, which is, I'm not saying hundred grandier. They're going to be out of jobs, man. But it is them that it affects, not the hundred grandier. And the point, the good thing about the hundred grand a year process, there are other white I call the jobs at a hundred grand. But I'm gonna say, I think I'm a compassionate person. If I thought that hundred grand person, the next best option was 20 grand, I'd feel we'll empathy for them.

57:39But if you know, if you got a hundred grand a year job that's gonna be automated, and your next best job is 95K doing something else, that's life, that's American capitalism get over it. I mean, you should feel the need to hustle day. I don't think that's called fear. You understand me? You're putting on a weird face, like as if you disagree. You think that, well, no, I just think there's like a generation of 23 to 30 year olds who aren't really masters of the craft in any way don't really know what they want to do and so they're doing SDRs or marketing and they're about to get a train hit them in the face and they're going to go oh shit.

58:11Let me just give you a quantitative version of it. But they'll pick themselves up and keep going because you're young, you're done with education. You know, yeah, it'll be a little bit hard. Yeah, they're checking out. Just to pull the numbers, because Toby did do the black and white at Shopify. Okay, let's look at Shopify for a minute. From peak employee was 2022, 11 ,600 employees at Shopify. Since then, revenue has grown 91%, pretty impressive for a company at 11 billion revenue, and employees have gone down from 11 ,600 to 8100, gone down while revenue is up 91%. So I'm sorry if like Toby and now that was early on this, he went into beast mode, okay?

58:54And he destroyed the competition. Big commerce doesn't exist. WooCommerce doesn't exist anymore. Amazon was never a threat, even though it wasn't direct competitor. He went into beast mode. And he just got there earlier than the cracked kids in San Francisco. He just got there earlier. And Shopify is doing 91 % more revenue with 30 % fewer employees. And if you want to fight that, like people would say I was toxic or was hurting their feelings a couple months ago And LinkedIn, I'm like, I'm trying to help you. You want to be one of the 8100 at Shopify or not? You got to decide because you can't leave work at three o 'clock to get your salad and go and go work out It's just not gonna work.

59:33You're never gonna learn the product and even worse You're never gonna beat the AI that knows your product cold This is the common reckoning for these people is that the AI knows every Shopify feature and every Shopify, every AI that Shopify merchant knows the products better than the humans. AI is smarter than most humans. Pre -AGI is smarter. Have you ever talked to an SDR that even understands the product they sell? Any 20 -year -old, like once in my career, if I talk to a 20 -year -old SDR that knows the product better than me, it's worse with AI. These people have gone, Shopify is going to be at 7 ,200 % bigger.

1:00:06You got to adjust. The Shopify numbers are stunning if you think about it. It isn't a 30 % employer reduction, 91 % revenue growth, and it's just starting. It's just starting. And that is before all the AI mandates went out, right? It's concurrent, but it started before everyone in tech is now, before you're placed someone find an AI first, aren't they? It's become the mantra. So it's going to accelerate. And I think the week, but I'm going back to the scared comment. That's funny. I sound like I'm arguing, but I'm actually great. I think my guess is that person's being a hundred grand. Maybe they only get 80, but whatever.

1:00:35I got this one. The thing you should be scared about is you should be scared is if you're on board something like shop about what you've really lost there is the opportunity to participate in four years of equity that could have made you four million bucks That's where fear anyone who's in the kind of I'm scared every day because you should never take your job for granted Especially if you're in the kind of job you make millions of dollars if you do it well And I think that's the level at which you can be scared and those folks they should have been scared I think that because they went for the hundred grand a year job I'm just trying to think of the equity to think.

1:01:07I get you either the opportunity cost on the upside of the X is insanely real. But having come from some a family that's lost everything, I worry about downside. Quite frankly, I don't think there's a ton of employers that are queuing up for a 23 to 30 year old grad from a mid university that's not a specialist in anything in a world of AI, cost cutting, and economic questionability. No one wants to hire them. No one wants to hire them. They'll have to suck it up and learn to do different things, but to a running hour, they'll be fine. I mean, if you look at the graduate on the anecdotes are there, but and it is higher than its being, but I'm not going to cry for someone in their 20s who has to adopt.

1:01:47It's a very different feeling. The kind of fear someone feels of 55 when their job as a fill in the blank could go and they've got nothing ahead of them for 10 years. That's fear. Right? And I've seen that kind of fear too. It's going to grow. Would all you respect? Are you at the tw - I think we're actually hitting it. saying the same thing. You can probably get another job. It won't be as good. It won't have the equity upside. It's not even going to get a job. It will. It'll be fine. Until maybe 18 months ago, if any seasoned B2B executive that I knew needed a job, okay, that I knew reasonably well, I get him a job by an email.

1:02:20I could reach out to someone, not even my portfolio extended network founders I met that I knew met on 20 VC. I could get them the job. Today odds like our 10 % I can get them a job. One, the fire's not there. Two, they're not willing to be cracked. Three, they're not willing to come to the office. Four, they don't know the AI tools. I can't get them a job anymore. You're interested in making a job. Are you talking about the 50 -year -old guy or the 20 -year -old guy? Yeah, now I'm talking about 38, 35 to 55 to 95. No, those folks. I can't find them any jobs, the veterans. They're not. And I told you, not a single job.

1:02:51I say go to Cisco before Cisco realizes they don't need you. The thing I love about these shows is learning from you. I learn from your on Palantir, I don't freaking get Monday .com. Has a good quarter, it's down 30%. What? Well, Rory may have a more nuanced view on this one. I mean, I know the Shopify data and Palantir. I think Monday is actually the one that should worry us more as investors, right? Which is that Monday was priced to perfection, but growing to perfection. I don't think it's this quarter, it's that there came up a little soft and where they thought the growth would be, but it still asks elite, the bar, are this 50 % at 500 million AR and never missing a quarter and keeping it going.

1:03:31We throw around all these numbers, it's chmoveable and lovable in NAN, but man, the bars high. That's the only reminder to me is like, you know, just the expectations are so high today for the top performers that the ones that have those outline revenue multiples, it's just so high. Rory, I'll give you an unfair question because you love unfair questions. data dog, HubSpot, Palantir, and Shopify rank one through four on what you'd buy. I hate giving advice where I don't feel informed. I can give you a guess if you want. Well, we'll really think about it. That's why I love Jason. I'm going to take Shopify.

1:04:07It is gaining market share at scale. Palantir is growing at scale and maybe it's gaining, you know, it is gaining a certain type of market. It's dominating government contracts. Don't get me wrong. So some people could criticize me for being simplistic, but e -commerce is the biggest part of our economy, right? Even bigger than the enterprise. Roy's got the numbers and the fact that they continue to gain share is breathtaking. What if Shopify has 80 % market share and the economy is 80 % e -commerce? Like, help me do the math, right? Versus 13 % of all commerce already goes through Shopify, right?

1:04:41And it has essentially 90 % of the platform market share. So platform lock in even in today's AI world is kind of exciting isn't it you get you it's kind of exciting to have lock in I buy your decision. I don't buy your logic and I'm telling you to mean by that You know, if they're all being bought into same revenue multiple I think the Palantino opportunity in terms of gross margin dollars is way bigger The I was comparing a hundred and eight X AR to 17 .9 Exactly. Why that's what I was gonna say That was implicit in my analysis. No, and that's where it gets. That's exactly right. Because you have to say to yourself, and that's why I apologize.

1:05:17Because you got to say to yourself, that VC would say, and this is perhaps the difference between the question of these, if you were to rank the size of the opportunity from here, I think it would probably would be palantir Shopify, and then the other two is really top of the tier of SaaS companies. And that's pretty obvious and straightforward. You'd have palantir one, even with the enterprise. And I said, size of the opportunity, not valuation. and please know Ms. Koffehrer. Yes, because yes, Congress is huge, but gross margin dollars, the ability to sell $5 million projects to enterprise to corn and corn implement AI just strikes me as a wonderful place to be for the next five or ten years in a way that while it sharpifies huge, you know, you do have it's a more mature market.

1:06:02Palantir on the white heat of this is new, this is exciting and we have it no one else does, which is where Shopify, DataDog and HubSpot were 5, 10 years ago. But when I can't do my head, I'm not going to do because I'm not, as Jason says, how do you adjust that for the fact that the market is well aware of this issue when it's training in 120 versus 18? What are the other two training at you? I know DataDog is 15x revenue and they're having checkups on the wall. Here's the brutal one Monday, which we talked about off the charts good, right? After the correction, 8 .4x ARR. Dude, I bought this shit out of it.

1:06:35I'm gonna be all high -spotted. But think about how many companies do we have in our portfolios that are not as good as Monday that maybe priced around higher than 8 .4x ARR? It's just, Monday's the one, it's kinda soul -crushing. It's like, you sure your portfolio's so good if it's trading at 8 .4x, right? That's a tough compression to figure it out there, isn't it? And when the growth dies, all these businesses become very uncompaling in terms of valuation. You're exactly right, Jason. That's why you have to be just growth bigots all the way on these fields. Because once they flap them out, it's four to five times if you're lucky.

1:07:13But even there's still at almost 30 % growth. We're too optimistic about our portfolio companies compared to Monday. for 20 years up until 2019 the median sales multiple was 6 .3 each and the median growth rate was almost 30 % and now the median multiple is closer to 6 again the growth rate's 20 but the profit of the bill is more but yeah I mean for the longest time it was you only got 6x for 30 % well Dammar I think you did an amazing job there articulating before you have pound here one Shopify two data dog three in HubSpot 4 that's not what I think it is I said in terms of your you're stuck out.

1:07:50I'm critical. I did not say that. And if you say that, I did not say that. I said it comes off on penetrating. We're going to title this. Rory is public leaderboard with your face. I have to sing the new guests on your next show, howie. Mark Banny off his coming. He's got and he wants to hang out with you, Rory. Okay. Well, then you have to be nicer to me. I'm gonna be nice to you. Do you know what's amazing after last show cliff from Canva done? What do you call him? Arvind from Pplacsty done Jeff from Twilio done not Benny off done all wanting to come on the show all fans Little do they know that when you come on you just get asked think her questions where you have one of your most successful CEOs in the mix and you're just a joke out So guys, we mentioned that like actually where is the upside and where's the opportunity?

1:08:42Carter's state of Q2 2025 came out. Couple of things I want to dig in on and then we'll wrap. But highest valuations ever for seed and a and it goes back to what we said there about actually comparing to Monday. How do we feel about risk adjusted, where dollars are best and how do you feel when you see highest valuations ever for seed and a do you see that reflected in your daily work? But the card of data and everyone else's data also says there's fewer seed rounds been done than 12 months ago and 24 months ago. Everyone that doesn't read the stuff founders especially be cognizant, there's fewer deals being done and it's worse than that because the deals are very specific.

1:09:20Forget about the breathtaking growth of AI native leaders. It makes sense if you're concentrating into winners, this would happen. We're also just concentrating into winners across the board. It's not just 10 deals for 40 % of dollars. It's everywhere we're seeing concentration. agree and that to me was the much more interesting point the concentration in late stage round it's called an injury demo it's fine the leading will come at this and the concentration in late stage runs it's just amazing we run an internal process we look at every deal done we're for the total dollars we deal with every quarter for the last couple quarters we've literally had to back out one or two deals because they just make the statistics so weird like in q1 the deals we focus in total deals in our sweet spot enterprise B2B, 10 for total, I think $12 billion in total dollars raised.

1:10:07Open AI raised 14 the same period. It's just like twice our entire addressable market for us and a hundred other A &B firms was done in one deal. That's a huge level of concentration. Same thing in Q2. I mean, you have interesting enough. In some deals, Meta gets reported as an investment in scale AI because they call put the money in. And so in theory, it's a venture investment, which is absurd, but you have big round front traffic X, AI where literally your entire sector is smaller than one round at the super late stage. I've seen concentration, but never to that extent. Constrations unprecedented, right?

1:10:44It just is what it is. Is that a momentary element of time where we are in the cycle, or is that going to be a continuing feature of a new age of venture and technology? It's probably not going to go back completed to Wales. Do I think that's going to be a $40 billion dollar round every second month? And no, but there's no, I mean, there's a couple of industries now that are now appear to be venture accessible that are fairly capital intensive. Obviously LLM model creation obviously out of the fence. So that does appear to be a higher propensity to do more capital intensive industries. That's one thing.

1:11:18And then the second thing is the more you stay private for longer, the more this becomes a phenomenon. It's the effect of holding them longer means they become bigger companies bigger companies just to run their balance sheet You know you can if you're running a hundred million dollar revenue company You can have twenty million bucks on your balance sheet cash repost of your fight if you're running a ten -billion dollar company Even if you're profitable you probably become a building box on the balance sheet just to manage fluctuations So as these companies stay private for longer there's going to continue to be this steady stream of fairly humongous later stage for now and then add to that the nature of the businesses, the model companies, the defense companies are capital hounds in a way that South are consuming or not even wasn't.

1:12:01So yeah, I think it's maybe not as pronounced as now, but it ain't going back to everything when A's B's and C's and nothing be more than a hundred million dollar raise. It ain't going back and everyone that wants to go back or give that data to advice. We had Brian Halligan was so good, right before. If folks that got this far and haven't watched him, that was STR, go watch that one. And his point was when he's talking with Squays, like at best half of what I learned in HubSpot matters today, it's true in venture, right? We're not going back. The AI is so much bigger than cloud and so different.

1:12:30And unless the LPs cut off the valve, we're not going back to the old venture. You know, has been a good fact to the log firms. The synchronicity of people having a lot of money, putting it out in lots of deals in 2021, not not working, I might even have guessed that the next stage of the movie was kind of real retrenchment on those firms. You know, you'd seen that doing a hundred deals at 10 billion pre -didn't work, and maybe you can't deploy that much capital. But along come this crop of extraordinarily good companies, like, you know, when I like a topic, where you can deploy large amounts of capital.

1:13:05I think it really has provided justification for the opportunity for those larger funds to say, hey, look, you can put a billion dollars to work in two or three model companies, You all will have thought adventurous. Oh my God. There's no diversification. That's terrifying And it's not our business But I can totally see talking to an L .P. and saying this is the only way to access that risk if you want to access that risk You need this vehicle and that's why they exist. It's been marvelous for them We're gonna do a cow she quick fire cow she's obviously this prediction marketplace bets on cool real life things I've been creating my own first one and following our conversation because I really want to you, palantir, over or under five year market cap, two trillion.

1:13:48Its current market cap is circa 450, five years from today. So that would be in 2030. I love the company and I, Dave, exceeded all expectations. I just think company to two trillion from here is pretty damn hard. So I don't know. Jason. I'm pretty decisive. I'm just comparing that to Salesforce. Salesforce at 40 billion worth 222 billion. And now I'm feeling gravity when I'm looking, literally, I'm looking the number one and number two by market cap. It's, you know, Palantir's worth almost twice as much as Salesforce as we write this in Salesforce's number two, right, at 40 billion. So the AI is bigger than cloud, so that's the reason it's gonna happen.

1:14:26But I'm worried about a gravity when Salesforce is only worth 222 billion as we record this. So I want to take this bet, but I'm gonna go the under. Okay, we've got Wemble Stripe officially announced an IPO before June 1st, 27 or after. The correct response is, doesn't matter anymore. I mean, under so post -public. I don't know. It trades all the time. I mean, yeah, I'm sorry. I mean, the cash flow positive, widely sold, they're just doing their thing. But you think they will go public in the next two years? If the cast of capital gets markedly cheaper in the public markets than maybe, but they say to be more resistant than most and there's nothing going to make them do it because they're strongly casual, positive and huge scale and there's liquidity.

1:15:12So the truth is, it's an idiosyncratic bet and the calluses haven't shared their opinion with me, so hell, I don't know. Very honest, thank you, Roy. You're not chatting to them in an Irish WhatsApp loop over beer in the studio. Ever a cheeky pie with Dario. That was a very, very important sign, I thought. One of the best FinTech founders in the world is a moderator to Dario. I just thought it was ironic. Ten years ago people were like Harry Media will never work for you dude Just to let you know it's not a thing true. I think days at four I think strike do a super interesting job in media with the publishing and all and they're just more than most Companies does an intellectual curiosity there which I find the most attractive thing about that company I like to agree with public which is no I mentioned as a compliment I mean I know you that's one of the pile of that one.

1:16:00Yeah, it's two smart people talking to each other final one Will X AI sue Apple there's odds for this one? And I know you like your story. So yes, a hundred dollars gets you $209. No, a hundred dollars gets you a hundred and fifty one dollars. Elon has made it pretty clear. He's very unhappy with Apple and he's already sued open AI. There was precedent there, right? Yes, not eight because he appears to have a pen state to pick fights whatever one to just fun to watch. Be because it's all about the dispute with chat GPT. And to some extent you could, I saw a good tweet that basically said, it's wrong because the whole idea that Apple's going to favor anyone, they don't need chat GPT to be wildly successful.

1:16:43They need to figure out there. So it's a marriage of convenience. Maybe the bad answer says, it's Apple continued to be called Align with chat GPT. Then probably they get drawn into it because the chat GPT versus X .AI fight is going to be existential for a long time because that's what it seems to be both personal and business because you have the old X .AI business. So that fight ain't going away. So anyone getting sucked into that could get pulled into the mess. So to the extent they are then yes, they're probably not a bad bet. It's kind of like getting named in the lawsuit. You know, I didn't you didn't know it wrong but you're dealing with someone that did something wrong to me.

1:17:18So I'm just gonna I'll pull you into this mess of depot while you're executives anyway. Jason. I think it makes sense. I mean, Epic's doing them with sort of worth it, right? At the margin. He's in sense, and he's got a lot of money in XAI. I mean, he has, he's the richest man in the world, but he doesn't have unlimited capital. I think it happens. Guys, as always, I so appreciate this. I want one final question from you. You gave me a target of like someone to get for the show. I think I delivered with the people that I've lined up. If you would add one more name, who would you say it is? Well, look, for what it's worth, Alex Carp's always been my dream since the beginning of Saster, asked every single year since like 2015.

1:17:54So personally, if he has the energy to do it from his farm, that would be my dream. I love that. I agree Alex would be amazing. Now I want to make those shows, the best shows they can be. So please let me know what we can do to make them better, improve them. If you want us to have a guest on the show, I'd love to hear your thoughts. email me Harry at 20vc .com and you can find the show on YouTube by searching for 20vc. But before we leave you today, let's talk about agents. Specifically, Piper, the AI SDR agent brought to you by Qualified. The agentic marketing era has arrived and if you're a B2B marketing leader looking to scale a pipeline generation, Piper, the AI SDR agent, wow, it is here to help.

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1:21:53Go find out more, logora .com. As always, I so appreciate all your support and stay tuned for an incredible episode with Max at Logora tomorrow.