20VC: Musk's $TRN Pay Package Broken Down | Ramp Hits $1BN ARR and Brex Hits $700M: Who Wins | OpenAI's $10BN Secondary Sale | Atlassian Buys The Browser Company for $610M | ASML Lead Roun into Mistral at $14BN Valuation

11 Sep 2025 · 1 h 28 min

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Podcast Episode Summary: 20VC: Musk's $TRN Pay Package Broken Down

Episode Overview In this episode of *The Twenty Minute VC (20VC)*, host Harry Stebbings is joined by guests Rory O'Driscoll, Jason Lemkin, and Twilio founder Jeff Lawson. The discussion covers a variety of hot topics in venture capital and technology, including Elon Musk's unprecedented pay package, the financial performances of Ramp and Brex, the implications of OpenAI's secondary sale, and significant mergers and acquisitions in the tech space.

Agenda Highlights

  • Musk's $1 Trillion Pay Package: Analyzing the implications and future benchmarks for CEO compensation.
  • The Rise of AI Startups: Ramp achieving $1B ARR and Brex reaching $700M ARR.
  • OpenAI's $10B Secondary Sale: Effects on the tech landscape and employee cash-outs.
  • Mergers and Acquisitions: Discussion of Atlassian acquiring the Browser Company for $610M and ASML's investment in Mistral at a $14B valuation.
  • Legal and Ethical Implications: Addressing the arrest of the CEO of IRL for fraud and the broader implications for the startup ecosystem.

Key Discussions

Musk's Pay Package

  • Breakdown of Compensation: The board’s motivations behind Musk's compensation package are discussed, highlighting the high expectations set for performance metrics.
  • Future of CEO Compensation: Guests debate whether Musk's package sets a new standard or remains an outlier.

Startup Financial Performances

  • Ramp and Brex: Both companies are seen as benefiting from an AI-driven market, with discussions on how their growth reflects broader trends in venture capital.
  • Valuation Concerns: The valuation of Sierra at $100M ARR worth $10B raises questions about potential market bubbles.

OpenAI's Secondary Sale

  • Impact on San Francisco: The influx of new millionaires could alter the real estate market and startup landscape in the Bay Area.
  • Employee Retention: Potential effects on the workforce as employees gain liquidity from the secondary sale.

Mergers and Acquisitions

  • Atlassian's Strategy: The acquisition of the Browser Company is analyzed, weighing the potential benefits and risks.
  • ASML and Mistral: The strategic rationale for ASML's investment in Mistral raises questions about the intersection of semiconductor and AI technologies.

Legal and Ethical Implications

  • CEO Fraud Case: Discussion on the arrest of IRL's CEO and the consequences of fraudulent actions within the tech industry.
  • Trust in Venture Capital: Concerns about due diligence and the ethics of startup founders in light of recent scandals.

Key Takeaways

  • Evolution of CEO Compensation: The Musk package may influence future trends in how founders and CEOs are incentivized.
  • AI's Role in Startup Success: The rise of AI capabilities is seen as a significant driver behind the successes of companies like Ramp and Brex.
  • Market Dynamics and Valuations: Current valuations in the tech space may not be sustainable, with warnings about potential market corrections.
  • Consequences of Fraud: The need for accountability and strict consequences for fraudulent activities in the startup ecosystem is emphasized as vital for maintaining trust.

Conclusion This episode of *The Twenty Minute VC* opens a dialogue on critical topics affecting the venture capital landscape today, including the implications of astronomical CEO pay packages, the growth of AI-driven startups, and the importance of ethical considerations in the tech industry. The insights shared by the guests contribute to a deeper understanding of the rapidly changing environment in which venture capital and technology operate.

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Transcript

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0:00The real truth is the buyer has cunningly eviscerated the brains and the heart of the company and left the carcass and we're going to pretend it's real but it's dead as the dodo. And everyone knows it but no one's going to go on the record saying it. Scale was for sale for 28 billion. Brett's got to be worth 56 billion. I didn't leave Hollywood Hollywood left me. This is venture capital today. And this is the greatest wealth creation, wealth hunt, greed hunt, venture hunt, ever. Venture rounds are all getting done on Saturdays. Forget about no diligence being done two years ago. Now, diligence isn't even being attempted.

0:34I think the best control today would be if more founders that committed fraud went to jail. You all listening to 20VC with me, Harry Stevings. Now it is my favorite show of the week, Rory O 'Dryskyl, Jason Lemkin, and Twillio's founder, Jeff Lawson. Join us in the hot seat for a very special guest appearance. Today, we discuss everything from Elon's trillion dollar pay package. We discuss anthropics billion and a half dollar payout authors open a eyes biggest liquidity event to their employees in the secondary sale and much much more I want your feedback. I want these shows to be the best they can be let me know Harry at 20vc .com But before we dive into the show today Let's talk about agents specifically paper the a.

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4:21They recently also got an $80 million series B. From iconic, they're bat by general catalyst, red point benchmark and YC. Also, they operate out of New York, London Stockholm, yes their Swedes, always a wonderful race. With over 100 employees from some of the world's leading global law firms and tech companies, the team is growing super rapidly. They're just freaking awesome. Just go use LaGora honestly. I love Max that founder. He's just a great dude. Go find out more LaGora .com. You have now arrived at your destination. It is my favorite show of the week. I'm so happy you're back with the one and only Rory O 'Dry school Jason Lemkin and our special guest today.

4:58Jeff it is awesome to have you with us. So Jeff first off thank you for agreeing to do this with us today. Great to be here. the most pressing or a big element of news, which was Musk and the first trillion dollar pay package. Brace all prior benchmarks in terms of a trillion dollar pay package. I'd love to hear how we thought about this and whether this is a new normal that we should be expecting to see for your Sam Ormans of the world or this is a one off exception. Rory, I know you love it when I go to you first. Yeah, I like this question. It maybe think a lot and I did a little work and I think there's a lot to unpack here.

5:36Let's start with the first thing. I always say this compensation is how boards reveal their real priorities. Nothing else matters as much. So you can tell everything about what the board wants in terms of how they structure the CEO package. So there's two or three things here. One is, and I read the proxy value, it's 332 pages. I didn't read all of it by Gachau on 150 pages. What's clear here is this. The board wants the Irung bet. That's just super clear. We feel they They owe him the past and are going to get in the future. The second thing is they really did believe that if they didn't give them the extra 12 % on top of making good the stuff that was disallowed in 2018 he might walk.

6:13I mean that's in the thing every time. Wipe your wrong that you can argue that. But that's clearly what they believe in the proxy. And then the third I think the most interesting thing is they're really paying him to double down again. The truly not a headline is it's obviously a big headline. But some of those operational and market cap goals are huge. It's basically the board say, you know, where they ate or not largest market cap company on the planet We'd like to double down again and be by far on the way the largest market cap company on the planet That's the bet we as a board want to make and Elon is the way to make it so when you look at it you go I mean, you know, you look at it.

6:47You've got the market cap match, right? Because I think it's I think atrelean is the maximum cutoff So you got to make something with a trillion you got EBDA criteria You got to make 400 billion in EBDA for contacts Google the most profitable company this year make $100 billion. So you got to make four times more than Google. And then I think the most interesting one was the four kind of hot, what I always think of the most interesting metrics, not the money metrics, the what do you got to do metrics, 20 million total cars, that's doable. They've already done 10 million FSD. That feels doable because why would you have a Tesla not get FSD?

7:20I love my FSD. I'm a crop driver. But then the other two are I think a million Optimus robots and I want to say don't go about a million robot taxis. So when you look at those criteria they're basically saying double the existing business but on top of that build a whole new business on top. This is a board doubling down on Elon. This is the bet they wanted. I mean we can discuss whether they should want it or not but it's actually intellectually very clear. I find it pleasing. If you wanted this bet as a board this is exactly how you go and buy this bet from Elon. You say I will give you a shit ton of money if you take actually a dollar company and you double the quits.

7:56I don't love it. I was like, yeah, I got it. Jeff, what was it like on the other side of Twilio with your comp? I mean, thinking back, your comp package because you, I mean, maybe they didn't offer you a trillion. I don't, I don't remember. Did you have one of these crazy packages because they're becoming more common with startups now. My portfolio, I see it. No, I actually never wanted major comp like as a founder, I had ample equity and I always thought comp generally speaking just distracted like all the time spent on that. At least for me, one of my principles of compensation was always the more levers and knobs and things you put into a comp package, the more opportunity it is for someone to just think it's unfair.

8:30The idea was once you pass the bar of fairness, this is Daniel Pink's whole philosophy from his book Drive, that once people believe they're paid fairly, they focus on the work. The only thing you can really do with all these knobs and levers and variable comp packages is take someone who thought they were comped fairly and then suddenly make it feel unfair because oh, we missed that metric or that. I did my part, they didn't do their part, whatever. And so I was wanting as simple as possible compensation for the team and that also went for myself. And so whatever they gave me, I just said thank you and that was that.

8:58The more complicated you make these count packages, the more shit can go wrong. Dario, Sam Altman, my true cursor. You name any of these great founders who are very pivotal to a business. Could look at this and go, well, this is a new benchmark. Do we see this as a turning point in how we incentivize CEOs at scale, given how central layout of businesses or is this a one -of -one with Edon? I think this is the new standard for anyone whose board consists of their brother -in -law and other relatives. It's a good point. I find boards are more and more created by founders. They're more and more great job and everyone wants to get into the deal.

9:38I think everyone's got, in a sense, their brother and law and ex -boss on the almost all my portfolio companies, the founders control the board, not just from a cap table perspective, but from a relationship perspective, they control it. And I don't know what you guys see. I see all these deals happening. I see lots of deals, once you cross the unicorn, which now is like a series A. Every CEO's getting some founder's CEO's getting some massive upside package with massive goals. Instead of a top up for two or three percent after you've struggled for five or eight years, they're getting seven, eight percent or more.

10:11But you've got to have a massive outcome, $10 billion, $20 billion, $100 billion. It's becoming the growth VC playbook for right or wrong. And it's definitely happening. And if you go back to the first Elon Comp package in 2018, definitely was a wave of wannabes that copied that in the two or three years after that to the end of 21. It wasn't everyone to your point, how he was about 10. My guess is 10 % or less of CEOs went for it. And the first thing is it was typically the CEO asked me for it. For some CEOs, something like this becomes important and motivating and you can write every horse the same.

10:47And some folks are like, this is the core of who I am. And I think even is the example of that. I don't particularly love that style, but it's like, it's all about me and I am the most amazing person in the universe, compensate me accordingly. So to some extent as a board, you're left saying, what do you do in that circumstance? Now you could have done to Jeff Point, you could have done the bluff game and say, I don't think you'll leave if we won't pay you. My guess is they were angsty about that. Not saying rightly, I won't leave, but that's the thought process. Once you don't believe that to be it, once you think someone can leave, and by the way, the one person who can leave is someone who has three other gigs that are equally exciting, which is why your leverage is lower in this particular case.

11:26Once you've kind of crossed those two doors, you have the person who wants the egotistical win and he might leave without it. Then you're left with a negotiation exactly like we just saw in Elon's case. I don't think that's the norm. That will be the high water mark, not the norm, but I definitely think like all high water marks, it will push up other people's demands and aspirations. Right. If you thought about protected, maybe this isn't about upside, you made the upside case. This is all about building a multi -trillion dollar business now. know, what about the downside case, the downside case being that Tesla is overvalued and that it's all the culture personality of Elon Musk that creates that value.

12:04And if he leaves the house of cards comes tumbling down. I totally agree. Then yes, because there are two risks. One is the if you evaluate as a car company, you'd be evaluated on 25 % of where you are now. Maybe this is a car company where 25 % of our current market cap and then Elon's special source, which is the other 75. So as a board, you probably feel a huge amount of pressure to keep that person. You're exactly right, Jeff. And the other thing is, yes, because because the other option you could take, which they're clearly not, is to say, I mean, this is not really hard, no, you've built an amazing car company, we're a car company.

12:37Let's manage it like a really great car company. Let's accept that we don't want these future bets and let you can get a different person to manage that company. But you're right. The problem with that, with a quote unquote, negative vision, is you're right. The stock would be down 75 % next day. The individual shareholders who let us remind ourselves, have we voted this, the prior complaint twice when they didn't have to. They're like, the people who own this company want to make this bet. I personally find it a little terrifying. It's such a risk on bet that it makes my head hurt. That's what they want to do.

13:06And you write, if they, the odd thing is, if that bet were cancelled, if the board said, we're not going to do that bet, we're going to play it safe. Just exactly right. The stock would go, and, you know, as a board, you would be dealing with lawsuits from here to the end human time. So it really is a prisoner's dynamite. It's kind of a scary board to be on. I admire their courage. You get compensated well. I think they have one of the best board comp packages on the planet, but it must be a really odd dynamic negotiating with Elon, knowing that as you say Jeff, if you try to demonstrate resolve and he threatens to walk, you're down 75 % next morning.

13:39That will be tough. The tough thing is, you know, we've changed so much in tech the last like 18 months AI the AI greed, which is not all bad. What Jeff said is how I felt as a founder. Our generation, it's not that long ago. I've got enough. If I'm in the double digits, like don't get me wrong, I'd love more. I wish I hadn't taken all that delusion in the seed round, but this is about a team. I'm driving a team on a huge journey. Leave me alone, take care of my team. I've got enough, right? It'll work out. I think that's what Jeff said. That's how I felt. I don't hear that too often anymore. I think we've changed.

14:09When you're cognition and you go, and this is amazing, you go from nothing to 10 billion in what, 18 months area or whatever you say. This isn't the Twilio grind or the stuff. I mean, Jeff was at StubHub before that. They're finally IPO -ing now. This is a different world and folks are building great teams, but they're mercenaries. I want to cash out at OpenAI for 10 million after 12 months. It's not bad. It's just, I don't hear what Jeff said much from the kids these days. Well, can we even just talk about the idea that founder CEO is quit to go join meta. It's crazy, right? Or open AI. What's your take that Jeff?

14:44What's the policy of profanity on this podcast? I'm certainly you want. I'm British that like we swear all the time. It's good. But I'm accustomed to the founder CEO being the most committed, the most long term oriented, and the most visionary of the group. And that's what makes startups great. And so when the person it turns out is just a mercenary and we'll go anywhere for a higher paycheck and leave the rest of the company that they started and they run to Flounder. I'm like, as Jason said, this is a whole different world of why people are in the startup world to begin with. For I think a lot of folks and I put myself in this bucket, it was it was missionary.

15:23It was like you believe the world needs this thing And I believe that that's the best reason to start a startup because if you just want to make money, probability adjusted, you should just go get a job at a hyperscaler. and probability adjusted, you'll make more money. So you don't start companies to make money. You start companies because you love what you're doing and you think the world needs to have the thing you're building. Do you think an Alex Wang is wrong then? I mean, his invest has made a huge amount of money. It was a great deal for them. It was a great financial deal for him. It was he wrong to do that?

15:51I think it just shows that it's a mercenary move. It is, but are we old? Maybe, maybe. What have I done? I don't see it since 2022. I don't see it. Okay. So first of all, yes, we are yes you are old Jess. Yeah, I mean, that's an objective fact I didn't think I'd be defending the mercenaries here. That is literally subjective Okay, we're gonna have to put a pin that out on I'll let you write Jeff you are right you my age is a fact But whether it's deemed all the subjective oh god Yeah, cuz from your perspective I'm young you're totally right by the way That was another dig you two up a very effective world.

16:28Let the record show 20 minutes in, we decided gloves are off. Okay. And I'm going to defend those two transactions. First of all, I love your framing that you should start a company because you want to, you're not doing it for a rational risk of just a return, you're doing it because you have a mission, you want to change something. I would argue in both scale AI's perspective and, you know, wind surf, perspective, the objective facts where you the offers being made, let's call them the attempted acquisitions because I think in both cases the acquire or would have just bought the company if they'd been let.

17:00The offered acquisition was well in advance of the company's work at the time and probably in my view they're worth at any time in the future. So it's their highest and best exit and to some extent they should take about taking that for themselves or the investors for as many of their employees as possible Because I think primarily of antitrust, in both those cases, they couldn't do the clean here we just own the company thing. We had to just do some kind of bullshit structure. In case it was kind of weird. The casualties from that were you did blow the social contract for a number of the employees.

17:36I do believe and I think the data has come out. In both cases, there were residual money left to make the payout because remember the people who get left behind aren't the longest tenured engineering employees. it's typically people who joined in the last year and a half, maybe the total ownership is some 5 % of the cap table. It would have been entirely possible to take care of them as if they'd been acquired while still doing the steal. And I'm not sure if they did or not, and it's kind of in the mercenaries of, you know, the underground chatter, if they did, then I would argue those founders did the right thing.

18:08But if you look at the people who did really well from that, say, your excels and scale. They have the University of Wisconsin or Michigan or the Cystic Fibrosis Foundation, the Children's Hospital of Atlanta, all of these amazing institutions that got back a load of money and are able to do things now for scholarships and education, for medicine, that they couldn't do without that money, and a thousand people at scale who were in marketing or sales now will have to go and get another job at cognition in the valley. I think that's fair from the VCs perspective. I think what all the other board members that are not the CEO and founder have The pure fiduciary obligation to do the smart thing and all those venture guys did the smart thing and I'm sure they're glad They're well -pissed or happy.

18:52I'm sure they're glad they're happy. Let's get really people I think what Jack is saying it's true is it is different for the founder and even though legally you have the same duties and obligations as a board member as everyone else I think the interesting question all out of this kind of corporate lost off raises is I think for the founder it is there and I'm thinking about this in terms of these two deals in terms of going public dealing with post public stuff. It is there, baby, and I always feel in my head and know you can't articulate especially in the public company boardroom, the founder has has the right to be slightly different and pursue their vision.

19:24They have a a little more leeway to say this is what I want to do, right? And I do believe in both those circumstances. If the founder had said no, I believe we should go on here. I think the VCs would have gone on and if the founders say I want to fold, I think the VC's fold. So the practical reality is it is a founder and decision with everyone acquiescing. But what is this scenario? Is this a fold or go on when it's like, no, no, the company should go on just not with me because I can go make it on my ass. Can I just be very clear on that? In board of those cases, that's a pure attempts to get the government off of us.

19:56Right? Everyone knows board of these companies are toast because in the case of scale AI in theory met owns 50 % of an in theory their business is selling to everyone but matter and of course no one's gonna buy their shit anymore. In the case of Wensurf it was the the carcass was gone five days, three days later. The CEO who's selling out has to pretend all this company's gonna go on without me. The real truth is the buyer has cunningly eviscerated the brains and the heart of the company and left the carcass and we're gonna pretend it's real but it's it's it's dead as the dodo and everyone knows it but no one's gonna to go under work on saying it.

20:29Except for. It's said, I don't have to, look, let me give it a clue. If it was my billion dollar cap game by not admitting it, I would be quiet and stumped too. I would just fund with my MDA. Guys, if we cross over to the private market, it's a little bit turning tabs on this conversation. There were some pretty astonishing announcements this week. First ramp hits a billion in error. Brax hits 700 million in error. or a little bit of a rough patch, but seemingly back on now, is everything just booming? A billion and 700 is everything just working? No. I mean, I wish they were. I've loved to see all types of whining.

21:11Not one of those VCs to go. Everything I portfolio is killing it. No, all types aren't wise. I think those two businesses are good businesses at scale. They've regrouped in the case of Brex. the kind of business they are, they're selling money and they get interchange rather than you, it's possible to ramp those businesses very quickly. So I think they're a perfectly good businesses in a good place. I don't think everything's going at 50%. I mean, you know, they're good businesses with interesting dynamics. They're not really selling software, but you know, most of the time they're selling companies a credit card, which means extending 30 -day credit in return for interchange, which they share with the companies, which means your margins are much less than typical software, but if you're willing to lend money and grant progress, not on intended, go aggressively, you can make revenue go.

21:53They're cleaning Amax's clock. Roy, should they be valued like traditional financial services businesses, or should they be valued like a new technology first provider? I would think that's kind of the bullshit question, because in the end, everything should be valued on a basis of risk adjusted free cash flows. So just start with that. But what you're really saying is what's the best, in the absence of free cash flows. What you're really saying is what's the best rule of thumb to value those things? The truth is they have the margin profile and core dynamics of a financial services company, but they have the growth rate of a software company.

22:27You have to adjust and come somewhere in the middle with the expectation that this is the key sentence. Once the growth rate slows, they will be valued just like if they're growing the same azamets, they will be valued the same azamets. the growth is what's saving them. I do think Terry's point, the AI boom is filtering further and further down the stack in wider. We're seeing broad comm explode. Cisco, that's where our grandpa learned to be an engineer. It is accelerating, right? Twilio's seen some acceleration from AI, overall at an Uber level. It's not an AI company. No need to talk about Twilio per se.

22:59But I think we are seeing it. And I do think if you're a B2B company and you're seeing nothing, you're not seeing any boost from AI. You didn't get open AI or anthropic as a customer. You're not seeing any benefits. Like you get an F. You get an F. There's so much money flowing through this system. And open AI and anthropocalone are spending so much of that money, right? I mean, they're spending it. You gotta get some guys. It's like fish food at the top. It's floating almost down to where it's dark in the ocean now. It's embarrassing if you can't get any of it. Dude, sorry, that's massive forward of the day.

23:35I'm so sorry. You're doing it right. Jeff, thoughts on that? Well, yeah, okay. So I think we hit a bunch of things here. First question is, is the growth of, say, ramp or brex indicative of something bigger? And I don't know, but I think you're right. If it's deposits basically money getting spent, then you'd not really about ramp and brex. It's about, okay, how much venture capital has been deployed in the last 18, 24 months, and you look at there's a fair amount of it. Well, great, it's got to go into some bank. So are they winning some market share? Probably. I know I use Ramp for my most recent ventures, and so they've got a great product out there, which is fantastic.

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24:09And so, but is it all because all their customers are crushing it, or is it because there's just money out there? Are they winning market share from legacy companies? That could be also part of it. And then lastly, if their revenue is based on this debt product, then great, maybe companies having debt on their books is a sign of not awesome things happening. All that is to say, I think Jason's right, there's clearly a boom that's going on because of edge capital fueling it, which just pushes the question to, great, when will there be the returns that everyone's expecting on what time frame? And that's the big open question it seems now, but from a infrastructure provider perspective, we certainly saw this at Twilio.

24:48We had customers spending a lot of money on Twilio during the mobile boom. A lot of them didn't make it, but didn't mean they didn't pay us millions of dollars along the way. And that's just what it takes to go figure out who the winners and losers are going to be of the boom. We saw a lot of those along the way. And that's one of the benefits of being an infrastructure provider. It's also the risk because of all those companies didn't make it. That revenue went away for Twilio. And so we had to replace that revenue with somebody else. So it was either going to be more durable revenue or just the next thing that grows really fast and might be the hit thing.

25:20And maybe not. We'll see what happens. but in the mobile boom, there were just enough companies coming constantly that even if some of them ended up fizzling out, you had another batch that was the next one that could replace the revenue. And that's probably a decent amount of that happening today in terms of the AI boom that's going on. When we look at a price, last round was 13 billion, now 700 million growing 50%. And then you look at a Sierra, okay? But a love -brat Taylor phenomenal operator interviewed him before to not compete with Brat Taylor as the takeaway I had, but valued at $10 billion at a hundred million of error.

25:56And Greenoats leading it, we love Neil Mayter, one of the best. Is this market's going AI nuts again to our last point? Or is this again an extremely rational bet given the operator and the growth trajectory that they've been on to a hundred million? To me, when I looked at this, I'm sure there's a spreadsheet that justifies it, right? the 100x. But I think, I mean, Brett Taylor, if you buy Sierra, you get everything, right? You get the XCTO of Salesforce and Facebook and his team. You get it just like what you would get buying one of these startups and you get a potential leader. So my thought is, look, worst case, we make 20 billion.

26:32All these other deals are happening. worst case, I make 20 billion on the deal if I'm greenoaks or whomever, right? This is a generational guy. This is one of the top 10, I mean, guys there is, right? And this sounds like a better deal than buying scale. I'll buy him. If scale was for sale for 28 billion, Brett's got to be worth 56 billion. I mean, I think it's part of the math because you might not get it if it was Harry and Jason's company with the same metrics. I think there really may be downside protection here. What's interesting about the bet is, if you have a mental model of all these bets, it just ticks every button, but the last box, which is that.

27:10I, my mental model is always, we said this internally, is there a category that can support a big winner? Are these guys going to be one of the winners in the category and are you getting paid for the risk? You could argue, that's the kind of sequence of questions you have to ask every time you look at the deal. Is there, is there a category here? Absolutely. Other than coding, which is the infer play at the app level, customer support, customer success, is the number one use case for AI because it's just so obvious you have lots of people answering phone calls, answering emails, you can do 70 -80 % of it with AI.

27:42It just saves a ton of money. It's a car center. This is going to happen. It's a thing. And then are they the winner in the space or a winner in the space? They're clearly one of a small number of people. They've got a really nice position here. They're dominating the high end and you've got a person running at Hawaii. I didn't listen to your podcast. I've listened to the late -space podcast with Brett and I remember thinking, God, that guy smart. He was talking tech and business and can move between it. So if you're an investor, you're like tick box one, tick box two, there's so few deals that tick bought those boxes that you're just so tempted.

28:14So the only box left is are you getting paid for the risk. There's only one question left, right? The bigger the market size, the more you can squint and say, well, at some point this company will be 20 billion, 30 billion in value. Therefore, I can do it. You know, my downside is limited to a low IOR. In the limit, that's actually can be a fatal mistake because you just over extrapolate too many things. If you're a city of self, I'm going to commit this called investing sin only one time every year, you know, which of course isn't how sin actually happens once you do it all the time. But probably at the apps level, this will be one of the ones you think about because you're like a great guy in a big market at a terrifying price.

28:55Okay, I'll close my eyes. So I see how they got there. A hundred times AORR is pretty steep at that stage, but I see how they got into it, you know. The only thing I think throughout which is just the opportunity cost of the capital for Neil. You're like, okay, 350 million there. Yeah, he's probably gonna be doing 275 in a $2 .75 billion fund. Like, it's like 10 % of the fund going into that next check, which is the second check into the company. It's just an interesting one for me, which is like, hey, when he looks at the opportunities on his desk and where upside it is, he sees this as one of the top.

29:28That's interesting. And given the percent of his fund that this will be, that's notable. That's a very relevant way for a bench capitalist to look at their portfolio allocation, right? And you get dangerous from you get that much concentration. I'm not a bench capitalist, I'm an entrepreneur. And so the way I've always looked at it is when I start a company, all my prior ventures, that was 100 % of my capital allocation for myself, for my life, for my time, for my bank account, for everything. And so the whole idea that an investor would have a concentrated risk with 20 % of their portfolio, that's easy.

29:59This is why it's going to be having an uproar. This is your reminder that don't say you're brave when you put 10 % of the fund into one deal and the other side of the table they're putting 100 % of the fund into one deal with no way out. Yes, we put you out. Speaking of where to put funds, I saw one of the most interesting venture deals of the week was Kleiner Perkins investing 100 million into the $13 billion anthropic round at price of 183. It's that first investment in a model provider. Does every large fund have to have a model investment number one and then number two is it's actually just an indication that the best way to make money stay in the business is to do late stage AI when winners are confirmed.

30:37How big is that fund? 15 so it's probably a logo deal then right. You can't walk into the partners and not have an anthropocular open AI in the website. It's not enough. I think it's a logo deal. I think at 100 million no one just does a logo deal You did the math last week on the fly and I eyeball the math I started off going no of course you wouldn't and then you run the math and you go It's not a quiz you better told first of all in the abstract as you say if you had one so I don't think it's just a logo Deal I think when you look at the growth or again to repeat from us What if two things is gonna happen either this is going to be the flasters slowdown in history in the next two years or if it continues Anything like this trajectory this round is gonna work It's not that it's a bad investment.

31:19It's just not venture capital. It's a logo deal because it doesn't you weren't there at Twilio in the Seed Round you weren't Byron Deeder in the trenches with Jeff. This is throwing in a hundred million at 13 billion. I mean you look Do you even get a meeting with Dario or do you just get you probably just get a zoom? You probably just get a go in the office for a seriously you probably don't get to go in the office. You made a comment here. This isn't venture capital. I think I've quoted Gloria Swanson before. I didn't leave Holly what Holly would left me. This is venture capital today. Most of the money in court -uncored venture capital is we venture capital is 20 % All -school venture capital and 80 % plus or minus late stage What would have been fidelity growth public investing?

31:58This is where most of the dollars are going today So first of all it objective fact it is where the money is going just because that's the fact and then secondly I mean how he said something insightful it must have been an accident He said you know is this not only the main place that's happening is it the Shrewd place? Is there a points on the board regardless? I mean, the thing about this is you have a chance to matter and be relevant. I can totally, it kind of doesn't need to be matter. I think the moon's awesome and I think they don't need anyone to matter because they have fake mother glories.

32:25But I totally get the idea of sticking some money in some ultra late stage, X -150 billion pre -round, just to feel your relevant in the space. It's not crazy on multiple dimensions. It's not the business you probably sold to LPs four or five years ago, but it's not necessarily absolutely wrong. I mean, it would be pushed to the extreme where it would become wrong. When all the other risks evaporate, remember the first two risks I range, the kind of, is it a category other? Where the only risk left is valuation. In the end, valuation risk expands to fill like a vacuum. So in the end, what will happen is people will over extrapolate and a bunch of these will be overpriced.

33:00Then people will go, oh, yeah, that's why you don't have a pay. But along the way, there'll be some great companies and maybe this could well be one of them where even these rounds math out. You're not in the trantress with Jeff and the seed like best somewhere or any of the deals, but maybe you've put in a hundred million again, three hundred million, that feels like an easier way to make a buck. So you're saying it's kind of like going to the mall with your parents credit card as a teenager. You spend a bunch of someone else's money to feel relevant. On a bad day, I'm not to be harsh because if your parents were grading you on the quality of your purchases, then yes.

33:32So I mean, we've chosen not to do that. Harry is literally hiding behind his microphone. I just love my moon. I just don't want my moon to hurt me I'm trying to mix me in a chain. He's one of the best of all time But but the hundred million can't three X the fund on its own. Can it? I mean, I would argue that you should You agree so in other words, you're basically on my side, but I'm saying it's not crazy Jeff is being I don't say there's a negative being a little pejorative about it And you're saying that only I write but I actually am being a wimp not doing it myself Yeah, which is another way to say it more directly to Jeff.

34:07You're disagreeing with Jeff. You don't think it's just kids buying with the parents' credit cards. You think it's a rational strategy in 2025 for venture funds to put a big slug of the money in ultra -late -stage investments because risk adjusted the return might be the most attractive. But you know what, there is another thing in all seriousness. The moon's one of the best to ever was and Figma's, I mean, that was his first deal at Kleiner. I mean, that's multiple billions back. But here's the weird thing. Today, here's the weird thing. Figma's 25 billion dollar company. It feels small. It feels niche in this world world.

34:35It feels small compared to Canva when we had Cliff on last week. And it feels very small when we're talking about Databricks, just crossing 50 % growth at 4 billion. It feels small compared to Anthropic and OpenA. It feels small. And as great as Figma is, when the 19 year old fadders walk in and all you've got is where's your AI one? I mean, Figma is great. My old team at used to use it, but that's just a little niche SaaS application to 20, 30, 5 billion. I know it sounds facetious, but listen to this. I mean, the numbers are so big today. And this is the greatest wealth creation, wealth hunt, greed hunt, venture hunt ever.

35:14I mean, these are orders of magnitude larger. A little $10 billion company is not enough today. Look at Brett Taylor, he's just getting going with his A. Staying on something very notable around the space is OpenAI and the secondary that they did, which is $10 billion is expanded more and more, how does this change surrounding areas? And it can be anything from San Francisco's real estate market to the retention of those employees, to the amount of angel investors. The valley is about to get a lot, a lot of million as that it didn't have before. What changes? I'll just go say, I just remember feeling that way before Twitter's IPO back in like 20, was it 14, 15?

35:54I just remember because I actually was like looking for our first house, I think around that time. And it was like, I just remember thinking like, oh my god, I gotta get, if I can buy a house, I gotta go before the Twitter IPO because everything's gonna go nuts. And you know, and the question is, did it? Like, yes, it did. Is that because of that particular batch of people that finally got some liquidity? I don't know, but I hope that San Francisco, and I know some of the leaders now in the Bay Area are focused on abundance and growth mindset in terms of housing and in terms of building capability to absorb new wealth and also not have the displace other folks.

36:29And I think that that is the mindset of folks in office now and I think it's a good time for it. Flipside, which is it'll create more entrepreneurship. And so you probably get more founders now spinning out of open AI once they get liquidity because they're affordability to take that risk. It's another upset. I agree. Because you made a comment that's not correct. It's unprecedented. A private secondary of 10 billion is unprecedented. I agree, but if this company were public and more or half a trillion dollars, like we mind our Apple was only worth 800 billion in 2018 and was the largest market cap company.

37:03Half a billion dollar company, 20 % held by management at the 100 billion. The headline could be portrayed as people who are very wealthy choose to sell 10 % of their total holdings to slightly diversify as an entirely rational move. Much less dramatic, I'm willing to bet when Apple was worth half a trillion dollars, this This kind of money flow was taken place every year because people would be crazy not to diversify some of the holdings. It's only anomalous because it's private. A company with the same market cap in the public wouldn't be as obvious what's going on and we digested just like as just said, they digested Twitter, you digested matter, they digested Google.

37:40It's not as anomalous as it seems. It only is weird because it's private and it's relatively early in its life. I don't even know if it is negative that early. So you're right. They are 2016. Good. I mean, yeah, I mean, much later if you only joined two years ago when you get in 10 million bucks, you feel pretty good. But yeah. And of course, the other thing, the fun thing is that if you think in video, the guys who peeled off of it in video at half a trillion dollars four or five years ago, I'll probably like, ooh, I took 10 million off the table. It could have been 60, bummer. So if you believe in the journey and Sam Aldman clearly is articulating that journey, you know, you might believe in money on the table.

38:11Just say, there's maybe here you won move on. I think the biggest difference from like the Twilio time that Jeff was talking about was, Oh my God, there's so much liquidity, right? Or other times is the impact on recruiting so much bigger in this generation. It's so big. And if you're running a boring B2B company, only going triple, triple, double, double, that's all you're doing. Even just 36 months ago, you would have been S tier, right? Today, how you're not gonna get a lot of people. It's engineering talent and, you know, we've asked a lot of folks on the show. We haven't gotten great answers from see how this question, how do you compete?

38:44And the answer has to be, we don't, We don't compete or we're not trying to hire those folks or we're not building an LLM. It's tough to get AI talent. It's just tough when everyone's making eight figures like hand it out like candy. You know, you should do shaft like have like Jim Farley from Ford on the show asking how did you recruit developers during the teams when they could have gone and worked at Twitter and Facebook and it's the same problem, right? Yeah, or the NSA. I wonder too. Who wore in that era against, you know, Silicon Valley? Well, Tesla's the only one that can really do what it does.

39:17Amazingly, actually, I point to Domino's pizza. Yes, best stock. Ten -year killer is not a great tech operation in Ann Arbor, Michigan. So maybe the key is get out of Silicon Valley. Interesting you said that, Jeff, because the other thing that turned out to, oh, maybe it's correlated, probably it's correlated, they also been a stunning ten -year stock. Oh, yeah, the best return, better return than Google over that time. Which I just love. And I did not know that they built it, because I did not know they had a great tech operator. Interesting. But you talked to I you probably shouldn't be competing for the same people in mountain view But there's lots of people who don't want to be in mountain view can't imagine why as you say good on our machine Well, and I struggle to think of a single like kind of let's say legacy company who said hey We got to get in the software thing and opened up their Silicon Valley office and actually made it work Yeah, interesting come yeah, because Walmart did it for while I think they closed it GE did it with that whole weird thing that totally blew up.

40:08Yeah, no, you probably right interesting going from employee payouts to one we didn't need but author payouts and through picket paid out $1 .5 billion to authors. Is this a one -off preffer forgiveness? Is this a continuation or a new business model? How did we analyze this? Easy and super clear. If you read the judgment, it's really interesting. The judge said the following. If you bought the damn book once and you used it to train your model and provided you pay the 15 bucks per book, that's totally legal. If however you download that this corpus of books didn't pay anything, use it to train a model.

40:46I'm going to find you $3 ,000 per book, which is how the fine was wise. It was 500 ,000 books at $3 ,000 a book. So it's actually a fair amount of clarity here. What it says is if you want to train on far -off 100 ,000 books to build your LLM, what you actually have to do is buy the book, slice it off, OCR the whole damn book and you can legally use that. But if you don't do that and you just don't pay the 15 bucks per book, you get fine three grand. So I thought it was actually a fairly coherent legal opinion that said this is the cutoff between fair use and non -fair use. And I think I'm sure it just made the mistake way back when of not doing that and got cut for it but cheaper the cost probably like yeah, we should have done it.

41:26It's not like it's not a crime. It's like we should have done this. We're going to pay our three grand per book, which we paid 15 bucks a book. Life goes on. So the future is you're going to go to the bookstore and you're going to buy a book and it's got like a steel bar through the cover, but the version without that costs $3 ,000. I assume that there will be a much more efficient way than that of doing it. You're exactly right. I'm sure for example, that there will be a corpus available of a purchased copy of every, you know, I'm sure that someone in these labor guys, it says, we have bought for you and just for you, 500 ,000 books, Scandan, just for you.

42:02So we have a legally compliant book set that you can use for training. But yeah. Having said all that, like this is pretty bad. I think begging for forgiveness, right? The classic startup thing. It is interesting. But they downloaded this from pirate websites. Yes. Okay. This wasn't cutting a little bit of a corner. Okay. This wasn't claiming something that wasn't quite open source was this is literally guys. We got to get this rocket ship going. I need a trillion books. I'm going to the two places where I can download them. Pure piracy. Pure, this isn't even stealing YouTube videos like OpenAI did.

42:35This is as bad as it gets. You can't defend it. You can't defend Pirate Bay for books. No, you can't defend it, but to be fair, they just paid a two thought. You know the concept of triple damages? Triple damages would have been 45 bucks. They just paid 200 damages. And they may end to pay more. They may end up, it's not over. They may end up paying more. I'm not saying it's bad, but this is as bad as begging for this isn't just for tending. I'm not using someone's API. Why are the coherence of the judicial ruling? And again, these guys think unlike some of the other branch. Yeah. They just said, look, this is, if you've done this, this is what a car ski didn't.

43:12And we're going to charge with 200 times as much per. And you're right. It's a big fault. And no one's going to make that mistake again. Now you are, you could have got to pick a number or you could have said you've injuncted I'm not using it, but that wouldn't make sense in the context of you have a damages claim because you're loss of earnings because it said because you're not directly reproducing the book. It's fair use. So you only damages claim is 15 bucks. Now the interesting case is what some of these artists are saying, it's not a question that you're just using my art to train a generic model.

43:41When I go on to the model, I get effectively my art or my sentences back. At that point, you go from 15 bucks a book to a much bigger damage. So I think there's still litigation to be had and decisions to be made in terms of how fair use manifests itself into kind of AI age. But I thought this was kind of a okay clear, that's one piece of puzzle established. We've discussed OpenAI, we've discussed Anthropic. Mistral announced last few days that ASMR have become their largest shareholder at a $14 billion price. case. Everyone is slightly scratching their heads at this if we're being honest. Going, did every other venture investor turn them down?

44:21Why is ASMR funding this? $14 billion is a huge amount of money. How did you guys analyze this? Help me understand what is going on here. I don't know if I can, but just so everyone in case everyone doesn't know as they listen, ASMR is a semiconductor capital equipment company based in Holland. It's one of the two or three most important capital equipment companies on the planet. The machines they make and sell to TSMC, make pretty much every semiconductor possible. It's one of the most strategically important companies out there, and I think it's one of the largest market cap companies in Europe.

44:54So it's far removed from AI software. It's at the top end of that. If you think in videos complex, one level below in videos TSMC, but one level below TSMC is ASMR. So it's in the AI value chain to use Jason's metaphor earlier, but much further upstream. So that's kind of just the context of what it is. As to why it's doing this, I have no clue other than some kind of European, maybe the biggest tech company in Europe should support, because it is the biggest, the most successful tech company in Europe should support the biggest tech AMAIL, a LLM company in Europe in some kind of your conglomerate kind of basis.

45:32I don't know. So they have less of a right to do this than my moon in European. Almost everyone is less aware to do things than the moon. He's done so well. One thing, and I don't know how European FASB works. Jeff may have some thoughts here from Twilio. When big companies with a lot of cash make corporate investments, it's weird because if you're generating massive amounts of cash, it's orphaned on your balance sheet. You can't just go higher a thousand engineers, it hurts your EPS, right? But if you can swap it one asset for another and that asset is not impaired or it's impaired many years down the road, it can basically be free.

46:05There has to be some synergy here. don't get me wrong, but it doesn't have to be a VC synergy, right? If the asset isn't going to decline, if they're looking at all the AI revenue that TSMC and others have, and they think they're not going to lose money on this, I mean, I remember, you know, a few years ago, someone that used to be high up in Salesforce Ventures said it to me and it resonated with me. It's like, you know, we just said, Mark, our job is to make money at Salesforce Ventures, but it's more important we don't lose money. Because if we lose money, we may have to take an EPS hit or an impairment charge, but as As long as our investment doesn't go down, it's pretty much okay.

46:36And so just the motivations here, they have to make business sense, but not just not losing money might be okay, because cash is locked. It's hard to get, do anything with it. You can re -porture your shares. That helps. You could invest. And that's about it. But it's kind of like having the entity in China, which is like, okay, well, it may go make a bunch of money, but is it your money? No. And so all you can do is then reinvest it in the next thing in China, I don't know, the next and you will basically never have that money back. That's kind of what the VC thing is for companies, which is you're right.

47:09If you've got this money burning a hole in your balance sheet, now investors might say, well, give it to us and let us make those investments. That's the argument. But if not that, then you're right. They can feel free to go make this and the income they make from that will be discounted, but it's not 100%. Well, I'll get something credit for it. But again, now that you just made your problem bigger, you got more cash in the balance sheet. you go like, you need to do an X investment in the next. So, you know, it's kind of a wash, but so the really the thing I would say if I'm say Salesforce or a corporate investor like this is, is it giving my core business some sort of fundamental advantage?

47:41In the Salesforce world, the answer I would say definitely is yes. Obviously, it's meant to the role in the center of an ecosystem. They ended up making acquisitions. They have more information to make their product decisions on like all sorts of benefits are created Salesforce. And I don't know if you could say the same will be SML. I think you're right. I love the common catch because just as a reminder, if you think software is is hard, the semiconductor business is way more cyclical than the software business. And you have to be tough as nails to want a semiconductor business. Who thinks the software business is hard?

48:10Hold that thought. Let's hard to say on top. Just hard to say on top. Okay, we can come back to that. But if you think the semiconductor business is hard, the most cyclical business on the planet almost is a semiconductor capital equipment cycle because it's kind of a leverage versus a semiconductor cycle. So to your point, Jeff, I doubt it because I'm so sick, but there may come a day when you need that one and a half billion and sometimes you just need cash. So, you know, I'd always be wary of tying up capital. So you do wonder about that. And you write the strategic value isn't obvious to me.

48:40I mean, I don't know if you need to own the models to sell the capital equipment. I don't know if anyone's ever seen a picture. This is the most complicated machine on the frickin planet. I joke you not. They are huge. They are enormous. They take months to a sem. They make a boring jet seem trivial in terms of their precision. So these guys are not dummies. They perform the single most complex engineering feet on the planet and they make a lot of money doing it. But I agree, I just go, maybe it'll work, maybe you'll make a three acts, I don't know. But I think a lot of it could well be just knowing Europe because it has been interesting to see this whole dynamic of non -US regions and non -Chinese region now, feeling the need for some kind of local champion because the combination of the heubistic talk about AI, coupled with the heubistic nationalism and behavior of the US and China means if AI is terrifying and these other countries are very aggressive about enforcing their stuff, maybe you do need a national champion and maybe some element of this is that behind the scene stuff, just like in the Middle East, you're saying that.

49:41I'm not saying I agree with that even slightly, but it's what happened. Can I ask you, Roy, when has sovereignty ever been the sole driver for a company's success in the past? The British East India company did pretty good. It just went over and took everything. But I agree. I'm not a believer in the tech space. I said I don't believe in it, but I'll give you an example If there is a free market in trade then the national champion of any tech makes no sense You should have a couple of companies competing on a global scale But let me give you an industry where there absolutely are national champions that's high tech defense when people are afraid That other people won't sell them guns or weapons.

50:19They make their own weapons and what's been interesting is this perception and widely or widely, I think, I think strongly that AI is caught like that. You start having this perception, national chapter, not because it's the best solution because it's a sub -optimal solution based on concerns. And I think that is true. The Europeans make a whole load of defense equipment that they have no business making from an economy -suscaing perspective. They simply do it because they're like, they don't want to rely on the Americans. And this is the AI version of that. End of. I agree. The ironic thing is, if you go anywhere in London right now, or the only thing you see is Androa Billboards, everywhere.

50:53They've done a great job of seaming European and Europe. I actually thought that was one of the slickest things they've done, establishing the local subsidiaries, talking the talk, in a way that some of the other vendors haven't been able to do where there's been talk about disabling advanced features and a lot of Europeans are holding off behind. I'm not sure if it's the S16 or the S35, but yes, androa's done a good job, but they've had to do it. And they made a super strategic acquisition in Australia, which also made them a lot more Australian, the Australian government, people on the ground, an Australian company incorporated, made a lot of sense.

51:25In terms of going back to the corporates investing and the benefits that come, you mentioned Salesforce there, and how it put them at the center of the ecosystem, Jeff. Atlassians M &A team is just popping corks these days. I mean, these guys are going on a tear. They're quite one of my companies cycle. It was a small acquisition, like $21 million in cash. Great. Thank you. is a seed investor, the browser company, $610 million in cash. Josh is amazing, fantastic product team, $610 million in cash is a lot of money. How did you guys analyze that? And were you as shocked as I was? I read the thesis behind it.

52:03You know, Mike's always been a real forward thinker, but I would say the thesis didn't really resonate with me in terms of we need a different browser for work. I could imagine some upsides, as enough upsides to actually changed behaviors? I don't think so, but did that thesis make sense to other faults? I think we're at a moment in time where everyone feels like they got to make a play, right? And maybe Jeff you've lived it. Maybe you don't really have to make a play when you feel like you have to make a play, but I think everyone's itchy in the seat, right? Whether it's a ASMR and a mistral and Atlassian is one of the greatest of all time.

52:35But it hasn't seen the AI, but would this be the play? I don't know, but sometimes when we're itchy and it's true for investing, too. Sometimes when you're itchy, it's not that you make the wrong investment, but you might not make the ideal investment if you're not itchy. Like if you've already gotten three deals done by September, you might just phone it in for the rest of the year. But if you haven't gotten a deal done by this point, you just might throw in a hundred million into the last round because it's the best ideal you have. If we can call Mike and ask him, I'm sure as a public company CEO, there's nothing you'd enjoy more than an unskilled corporation with this group of idiots about one of his products.

53:08Well, but when Jeff puts it that way, I mean, look, that's if that's the bet that listen, and it lasting has a massive footprint in the knowledge worker, both enterprise and developers, right? We're gonna push this browser and it's gonna give us an AI play. I mean, there's worse bets. I watched Jeff as an M doing his M and A and I watched Michael Kent. It seems like with the last scene, they do what Michael thinks works. So loom, trello, these made a lot of sense, but maybe they weren't impactful to it last scene at the other end. Jeff, when I watched them, I'm like, this guy isn't wasting time.

53:38He's like, I'm gonna buy segment, I'm gonna buy zip whip. like this was a man on a mission. He wasn't gonna wait for these new things. This is my view as an outsider. He wasn't gonna wait for little things to germinate eight years later. He was gonna put points on. I loved your M &A strategy even if it had risks, right? Because you weren't waiting. Were you? No, I mean, I hear something. We were never under the misconception that SMS would be the most dominant way of communicating 25 years from now. We knew that at some point, SMS is already legacy tech when we started the company, but we breathe new life into it.

54:09But like, at some point that will no longer be the so we have to parlay our success in that world in the amazing customer base, the amazing revenue base we have and parlay it into the next era. And so the question is we don't know how long that timeframe is so we better get busy doing it is that basically was our philosophy and obviously the messaging business is a great business for us but it was always seen as a bridge to an even bigger play that at some point in the hopefully distant future We'll be glad we did. I was like into Intel going from memory to CPUs or one of those in the fullness of time.

54:41We'll be seeing as people say, oh, remember, Tulio started doing SMS messages and you know, in the desk grandpa, what's an SMS message? Well, let me tell you. That's how we thought about it and that kind of urgency. The thing I would say though about any company in SaaS today and at last, Sion is a prime example of this is they are primed for disruption right now because AI is going to decimate their seat base for their products. It'll decimate the roles people are playing. AI will do the jobs that people are sitting there in at Lassian products doing today. So the question is, what are they doing?

55:12And now I look at the browser company, I'm like, I'm not sure that's the answer to what's going to potentially replace a whole lot of revenue. If AI is taking over these jobs that humans are doing in at Lassian products today, I would skate directly there and say, great, what is the job that humans are doing in at Lassian products? And here's the AI version of that today is what I would be doing. I think it wouldn't be the sound bite of the show because I know how he but that should be you're exactly right Jeff I don't know there's a super insightful set of comments from you to Jason and Jeff Yeah, to some extent you were like this is a good business, but we have to add on top of it It's a lot tougher now when you like my existing business could go away.

55:51I better do something you got to call those shots Maybe this shot didn't resonate but it's like you're probably sitting there as a SaaS CEO as a company said and you don't have the option of just letting the existing tank compound because it's not going to ask some Todd out and Caslow, it could start declining. And that's why to again, to Jason's point, I love the script of you do get trigger happy. To some extent, what you're really saying is this might be the best deal ever, but it's the best deal of the three deals on my plate right now. And I need to do something because I feel the imperative to act.

56:21It's probably a very honest in aggregate reflection of the dynamic right now. If you're a CEO and frankly also if you're an investor, you know, if you're not in, you can't win, but oh my god, it's hard to know. Well, you can't buy Sierra. You can't buy the things that are great. It's a weird world. Turns out making money is hard. I don't know how Jeff thought about it at Twilio, but when you listen to folks like Benny off and others, they want them all to work. But actually they have a loss ratio calculation, just like VCs, right? There's a loss ratio. And so of course, what is 600 million or whatever, but if there's even a 40 or 30 % chance, it's truly impactful to the customer base.

56:56That's probably good enough. Well, it's really the other thing that I think is conventional wisdom, especially at companies that do a lot of M &A like Salesforce. You don't worry about the deals that didn't work out, but the thing you regret is the ones you should have done that you didn't. And so the whole mantra generally becomes it's worse to miss a deal you should have done than to do a deal that doesn't end up working out. Can I ask you, Jeff, what deal did you miss that you feel you should have done? Probably can't talk about it. We didn't warn you that he knows this, but was there one? Is there one you still think about or it's behind you?

57:24There is one. You can see the love in his eyes. You can see the desire. He ain't going to carve it up guys. He ain't going to carve it up But you can see it's still there When you look at Mike on the offensive today whether we get the thesis or not and when you look at a couple of the other players in this realm of market cap Do you wish you were a public CEO on the offensive with a big ass budget to be aggressive and buy some of these assets? Or are you happy not being there? No, absolutely. I thought this was going to be a really Exciting time I thought for public companies to navigate this and like I said one of the things is like We weren't a different boat than most any SaaS company because a we weren't SaaS we're infrastructure So we weren't selling seats so we had no Innovators dilemma as a related to AI everyone was selling seats as a NAS Innovators dilemma and we didn't and the way I looked at it is we were always trying to crack into SaaS right?

58:20We built a context center product, a marketing automation product, and it was hard to do. It was hard to crack into the SaaS market because that's just not a people thought about us. And so that was frustrating. And when I saw this all the AI coming, I looked at it and I was like, holy shit, this is going to replace SaaS. All the incumbents here are going to have innovators to lemma. They're going to go add a feature here and there that's, oh, we're going to make your human being doing the 10 % more efficient because of the AI copilot thing. When reality is, they're going to want a product that is like, no, no, I don't need 75 % of these people anymore.

58:55Give me that product. And anybody selling you seats is like, they're not going to sell you that product. And so the amazing opportunity is to come in with that next generation. And that's where you see with all the AI startups, they're going zero to 100 million overnight. That's exactly what's happening. And so as Twilio, I looked at it and I said, hey, we finally got our break here. We don't have to become a SaaS company in order to build more value. we actually have a new way in that we are uncomflicted on and everyone else is beautiful. So that's how I thought about it. It's harder if you're a SaaS company because you got to disrupt yourself right now.

59:24So would you like to be in the CEO seat of a public SaaS company going on the offensive, having the ability to buy companies like the browser company? I think it would be a fun job. Do I literally want to do it? No, hey, I've got a new venture, but I've never wanted to be a hired CEO to me of being a founder is the thing I love. So that's my point of view, but for a whole lot of folks out there, do I think this will be a great time to be at the home of a company and navigating this transition? Hell yeah, because you got a customer base. You've got a lot to work with there, but you also have the innovators dilemma to work with, which makes it both hard and also super interesting.

1:00:01So how much harder do you think it is to make a bold move when you're public at a time like this, than being private? You have capital to work with. Yeah. And you've got shareholders who want a great AI story. And so the question is, I think all like for us, it was we got hit with headwinds for growth. And that becomes the thing you got to fix. And so the question is, are you fixing that or are you paying for the longer term? And it becomes hard to do both at the same time. And so if you've got the growth right now and your SaaS company, absolutely, you should be swinging for a 10 -second. That's helpful.

1:00:33And the hard part is if you're lacking for growth right now, it's hard to do both at the same time. I mean, that's the position that sucks to be in. That actually makes sense to me. And I'm gonna put an adder to it. It's, so if you're doing 30 % plus, you can be aggressive and you should be aggressive and by shit as a public -south company. What you're saying is if you're doing 10%, you can't be aggressive because you gotta fix the growth story. And then this is the thing I wanna add, even though you probably should be aggressive at least slightly because just fixing the growth story and getting it from 10 to 14 or 15 on its own without getting on board the AI train, probably is not enough.

1:01:07It is an interesting though, but obvious point that if you're selling at the infrastructure level, if you're selling, it is easier to get on the bandwagon. You have to have the right product, but you're not cannibalizing your seats. If you're selling messaging, if you're selling email, right, it's easier than you're not just necessarily disrupting yourself. Let's say your Brett at Salesforce selling you context -centered automation, and they've got Service Cloud, which is for memory a third of their revenue, right? You're going to cannibalize a third of the company's revenue. that's hard to do as a public company.

1:01:35Whereas if you're a pure play and just saying, selling the automation, your job is to go steal a third of Salesforce's revenue and replace it with a smaller number, but it's all yours and that's the whole point of being the disruptor in those markets. And interestingly, if you eat the label, it might not even be a smaller number. Oh yeah, it probably will be, but you don't need it to be as big a number as Salesforce has to build a grand slam company as a small. It might even be bigger if you can actually, I mean, some of these contract you're seeing you're getting more. Oh, in the end, yeah. I don't know.

1:02:06I doubt it. I doubt it because I think the economic argument will be like you save money. Yes. Actually, but the argument people are making is you saving not just software money, but labor money and some part. Can you command some part of that? I see the software plus labor is a bigger market than software alone. Yeah. That's fair. That's fair. Yeah. If it's a one for one replacement or even worse, as you suggest, a 0 .7 for one replacement, then a whole bunch of venture money is about to get flushed down the toilet. The only way the math works for the Sierra at 10 billion is if you don't just get India maybe not upfront, but over time, you don't just get the service cloud revenue, you get the service cloud revenue plus some slug of the labor.

1:02:44I'm not trying to agree with that, but I think the upside is getting a slug of the labor too. But I'm not trying to agree with even if it was just 0 .7%, 70 % of the revenue, you would still build huge companies that could eat the SaaS companies alive. Jeff, I'm sure you have consistently over the years spent time with the generation of public company CEOs and founders from your Atlassians to your Zooms, to your Mongos, to your Octas, to your Boxes, to your Dropboxes, to your all in the same kind of generation. When you look today at that crop of companies, which founder CEO do you think will be most aggressive and strategic in the acquisitions that they make?

1:03:23So I think Mike will be one of the more aggressive on the acquisitions front because they've always been And so I think it's in the DNA of Atlassian So I do think you are looking at one of those even if I am not fully onboard with the most recent I think Drew has a interesting vision for where Dropbox can go with AI The question is will they have a right to play there because I think Dropbox has struggled to expand out of core Sync and sharing market because they've tried a lot of things over the years Will AI provide an opening for them to provide a new market for their customer base? We'll see.

1:03:56I think he's got an interesting vision there, but it's hard to break out of the jail you might find yourself in those scenarios. When you at the Dropbox stage in terms of growth, it's just when you need acquisitions the most, but you find it hardest to do as a public company because you're still in the low -gold penalty box and that must be a frustrating place. Here's the thing I would say about both Dropbox and Box, both Aaron and Drew. These guys are cockroaches in the public market, right? Like they've been through hell and back in the 10 or so years that they've both been public companies and they've managed to survive.

1:04:27And I know Drew's got good protections. I think Aaron does too. I don't remember. But like they've managed to figure out how to compete brutally and manage to continue the path as public companies continue to invest a reasonable amount in R &D and advance the stories of their companies. And so I would bet on those two to continue to do that. Now, I wish they were both doing it faster, and I wish they were both able to do it more at scale, and neither of them have relied on any kind of big M &A, really, and that's probably a function of their presence as public companies. But I also think that their history of being able to plow forward and make it happen will help them here.

1:05:03And hopefully, what it takes, though, is some kind of breakthrough. Like they'll need some little bit of luck, they'll push through some opportunity that breaks for them, and then it could be amazing. I think both of them have a shot at it, but it probably won't be through Big M &A. It'll be through product smarts. Knowing both, you know, Aaron Andrew, they've both been looking for that opening, kind of like I was as a CEO. Looking for that opening that's gonna let you break out of your jail and, you know, kind of expand your product portfolio in a new direction and earn the right to play in a new area and AI is certainly one of those opportunities.

1:05:33And what way did you most want to break out of your jail that you were not able to do? Well, the thing that frustrated me, so our most successful product was our messaging product. And so as a messaging API, the crux of that product was an API with three primary fields, right, if you will, like from to body. That's a text message. Who's it coming from? Who's it going to? And what does it say? That's a text message. And so we had millions of developers who integrated Twilio into their code and specified in their code, a two, a front and a body. Now in that world, how do you add more value to the customer over time?

1:06:04They specifically said, out you send a text message from this to this that says this, what do you do to add value? You're kind of in a box. And so if you look at the last, say, 10 years of Twilio, it was all about how do we create a product that allows us the Expressiveness to go add value because the customer hasn't explicitly stated exactly what they want us to do and therefore any Deviation from that exact thing is called failure by the customer. And so that's a lot of what we are always trying to do is to create a Surface area that allowed us more expression as a product team and as a company.

1:06:37You know think about if you're a file storage company success as I stored your file and I didn't lose it. Failure is, oops, I lost your file, sorry. So you have to break out of the world of like, no, no, and customers want you to add value beyond just, no, my file was there. Thank you very much. That's the challenge. So certain product arenas and the nature of how customers use the product and the nature of the product's promise give you more ability to expand. I always admired the product surface area that Cloudflare had because they sit at the super strategic intersection of the world and then your website.

1:07:11And then you can ask the quran it's a dashboard. So once you're inserted into the DNS and you're proxying all the traffic, now without writing another line of code, they can add another feature to that dashboard. It says, oh, flip a toggle to do this and do that and do that and do that. Now you gotta do a flip of switch and it's beautiful. That's a great position to sit in because you're at the point in the product where you can just add that feature and make it a toggle switch. That's beautiful. Super interesting. To your point about it, it's funny. I actually was inside because I all started years ago, there was only two API companies.

1:07:40You guys that abstracted the complexity of messaging and stripe that abstracted the complexity of money. You were the interface for developers and a whole bunch of complex shit behind there, the curtain. And I think what I hadn't realized when you made it clear to me now is you probably had more degrees of freedom as stripe because there's more things you can do with money than you can do it to from text. And you were trying to find the unlock on top of that is my takeaway from that. Yes, and no. I don't know Stripes Financials, but I've given the fact that they've fiercely stayed private all this time.

1:08:14I wouldn't be surprised if they struggle with a similar thing and they've been looking for a better answer. I've heard whispers that a lot of their product portfolio is not really contributing to the business. It really is the core business, which is pretty common. I'd say probably the same of Twilio 2. There's a main product and there's a bunch of other stuff that you hope will break through, but it's always hard to do that. Yeah, if you want, if we want, we can take a detour and I can tell you my theory of all developer APIs, or we can talk about the CEO of IRL who was arrested for fraud. Oh, when you put it like that, big guy.

1:08:49I'm passionate about the fraud topic, but I am, I mean, Jeff has been, I mean, what was the billboard on 280, Astrid developer, right? Since inception. But I feel like, Jeff, I'm kind of bummed you're not in the game because I'm on One replet two hours a day, okay? I couldn't be a developer before Repplet. There is a renaissance of the developer, like everyone's becoming a developer, right? It's not just, I mean, literally I integrated the Sengred API in 60 seconds. I couldn't have done that six months ago. I mean, I'm not stupid, but I just couldn't have done it. Now, me and Repplet just did it, right?

1:09:20So I'm just, I am curious, I wanted to do one, talk about IRL and nobody at a time, but I do want to hear your theory of all of it because I feel like it's just become, it's a new world for developers. I'll tell you my theory of developers, let's say pre -AI, and then maybe we can talk about how it evolves. So my theory on pre -AI developers, and I tell this to every entrepreneur who would listen, who'd think about it, which was kind of one of our guiding philosophies as well. I thought that in 2017, 2018, we kind of went at this critical junction in Tulio, we were saying, okay, do we just go more horizontally in terms of services for developers, or do we go more vertically in terms of communication.

1:09:57And we chose to go more vertically in terms of communication. And part of the rationale was, I analyzed every developer thing that was out there. And I decided that there were three categories of developer companies that actually got breakaway revenue. And there were a lot of folks that were stocked with 10, 20 million, whatever, but there were only three that actually could break away into hundreds of millions or billions in revenue. And those three categories are number one, business development as a service. I like the worries taking notes. I've looked up business development as a service question mark.

1:10:23Okay, you're just developing a service. So if I am a software developer at some company, I am not allowed to go open a bank account on behalf of that company. I am not allowed to go strike a business development deal with AT &T on behalf of my company. I am not allowed to go stand up a new data center on behalf of my company. These are things I'm not allowed to do, but with Twilio, with Stripe, with AWS, you can now engage in these business relationships on behalf of the company that you weren't able to do previously. And this empowers you now to go build the thing you need to go build. And it turns out that when you just backdoor in that way, the developer has a lot of power because the thing everybody wants in your organization is a working product.

1:11:02And when the developer says, here's our working product, it just turns out that in order to have it leaders of the company, you got to go pay the build, the Twilio or the Striper to AWS. It turns out people are willing to do that, right? So business development as a service. Second, CapBat, you got your penray, CapEx as a service. So it's similar a more relevant to the AWS story, which is, Adrenalin Per is not empowered to go spend $10 million to build a data center. But can they put it on credit card? Yes, so there you get your CapEx now as a service that developers, again, they're spending money of the company that they previously weren't allowed to spend.

1:11:34But this is a CapEx play. So that's all of AWS and Google and everything else. All right, the third, and this is exceedingly rare. The third is algorithm as a service. Yes. And this is got to be an algorithm that is so complicated. So obviously beyond the reach of most developers that you are willing to pay someone else to do it for you as opposed to do it yourself And the reason why it has to be so complicated and a lot of folks I think think that their thing is gonna fit this bill They're like well, we're not business development and we're not CapEx but we're a thing that's really cool and the problem is that developers a take your really cool thing You're trying to charge them for as a challenge.

1:12:09Yes, can I go make that myself? It's like a challenge like you challenging me saying I'm a developer who can't build the thing you built screw you I can do that, especially true when it gets to actually meeting full revenue. Because even if you do get your foot in the door and you get into a product and see that company is paying you five million a year, now the developer is not coming to you like, hey, I know, I'm going to save the company five million bucks and be a hero. I just need to go recreate this thing and that's what happens. And so when your capex as a service or biz devis service, you have backstopped that instinct with, well, you can go build your own Twilio messaging later, but you still have to go integrate with hundreds of carriers around the world.

1:12:42Twilio. I would you, that didn't solve any problems really. But the algorithm one has to be so hard that the developers say, you know, I'm just, frankly, I'm not smart enough to go figure that one out. And in that category, I used to only put DynamoDB, like the infinite scaling database is like, that is such a hard problem to solve. Even if you have an open source project operating yourself is so hard. You just pay Amazon, they take care of it for you and you call it a day. And now I put inference in that category, except that pretty quickly, you know, inference became open source if people are running for themselves too.

1:13:16So it's not even necessarily in that category anymore. But you would put accessing the core and tropic and open AI. That is their business state, the enterprise. Well, except for the fact that you've got open source models or you've got Lama, so you can run Lama yourself and do inference yourself, right? I'm not saying that it is necessarily the right thing for folks to do, but people can do it. It's like arguing it off. No, I can do it myself. actually, which is valid, they can. I remember, honestly, back in 2016, 17, we looked at a bunch of these NLP APIs that were, you know, mid -level, trivial, hard.

1:13:50They got some developers, and you exactly right, they got taken out. And, you know, give KV credit. They did a bunch of those that only did okay, but then they very wisely did the one that did amazingly well in IE Open AI. And maybe what you're saying is, it may well be that the secret source is, if you just continue to spend an order of magnitude more money every year making the algorithm better than no one can catch up to you. And that obviously is the open AI slash, and traffic play now because, yes, you can get deal. Obviously, you're not selling inference. You're selling the model. You said that's your own.

1:14:21Underdrip. You said no. Yeah, that's why I was trying to pick up early on. We were saying, in front of you selling, you're selling, having, crane the model and doing the inference. You're selling two things together. Yeah. And if the model, let's say we hit a plateau and all the models basically the same, including Lama's open source. Then you just have a question of, okay, is inference a product that I will pay someone else to execute for me or is it more cost effective for me to stand up my own? And that's really a question more about tunings and things like that than it is about actually running inference yourself.

1:14:50But I believe inference itself is not such a hard algorithmic solve that, you know, you need to pay someone else to do it for you. But clearly training a model is. So yes, you have this secret recipe that cost you five billion dollars. And what you're saying is if people had the recipe actually doing the inference, even though it's a lot of the revenue court you're generating in that hard, you're just advertising your model. Interesting. That was super helpful. We've talked a lot about these, we've looked a lot of these developed business over the years. That's actually a very helpful framework.

1:15:18I was going to share it to actually Rory. That was my... Morning, I'm the manager. I was chatting before the show about it. I kind of gave it to him, but I didn't, you know, I wanted to give the founder the chance, you know? I'm a big bad guy. Everything I know about developers, I learned from Harry. Okay, we're the comedy section of the event. You have to understand, Jeff, my team is going to clip that. Everything Harry learned about awesome hair, he learned from me. Nice. And both those statements are equally true. Okay. Let's do it. We're going to do a quick fire. Okay, so what price will Figma be at in 365 days?

1:16:00It's at 52 today, which is a $25 billion market cap. Give me some numbers, Tim. I'm gonna give you a number that's gonna say it's about mid 40s and I'll tell you why I give it. It'll prove all these silly people wrong. I'm gonna give credit to the bankers, they priced at a 35, they get it, lovely 10, 15 % part, and one year's compounding. The price that it should be, if the bankers were roughly correct, would be around the mid 40s. So I'm just going to assume that they're more correct in all the idiot to price at 110 and move around and talk about it So I hope it ends up at that price and allow the bankers to say you told you we got it right it just looked wrong for a while But that would be an easy outcome.

1:16:38I'll take the interest rate bet and say it'll be 75. All right lower rates We're zirping again people were zirping Jason. I'll bet 60 will can the go out in Q4. Yes or no? No, no, it's 0 % They even talked about it. I feel like they're pretty happy were there. Well Cliff came on last week and he was pretty open about it I just don't think I mean Jeff's been through it. I don't have the benefit of being on last week It just takes time and they could thought they could have are they mean they I don't think they can confidentially fire But it's it gets tough to get it done in Q4. It's already September 9 I don't think Cliff would have come in last week and talked about not doing a direct listing if they are about to file I think the lawyers would have shut him down even though he's a so I think I think I think first half is the right question So I'm going to let me call Cliff and I'll get you a column in a answer.

1:17:25What time is it in for them right now? I don't even know if I am I wake in these people I know this should have been the show Harry Jeff calls that just should have been the show

1:17:36Bill and air software executive friends and just ask them random questions about business But but sort of uncomfortable questions out of the blue this will be his next appearance Jeff calls That is what podcasting is just without planning. Yes, there's no planning here I show you. Okay. I'm just on a tower against me today. I mean, he's just not. It really dispoys down to the two coffees. I've had too much coffee. It's not your fault. Don't know. I don't take a person. They trust me. It's okay. My final one is what Jeff mentioned. IRL CEO arrested for fraud. What happens here? Jason, this is the top of your passion about.

1:18:16You can kick it off. Well, I've listened. and I'm not a criminal litigator or lawyer, Roy has got one in the family, but yeah, hopefully it goes to jail for stealing millions from the company. I genuinely believe our ecosystem is so turbocharged right now, right? But with, in the Bay Area, I mean, venturons are all getting done on Saturdays. Forget about no diligence being done two years ago. Now, diligence isn't even being attempted. I think the best control today would be if more founders that committed fraud went to jail. I just think if every month someone went to jail that completely lied, an error or a disgree, completely lied in a round, sent financials where they aggregated all their years revenue in one month where they pretended unpaid pilots were pilots.

1:19:02If a couple of these went to jail every month, I think we would have the proper chilling effect and mitigate the rampant fraud we're seeing today. I just think it would be helpful for the ecosystem if that were penalized. And I know Rory thinks it's a cost -eventure, but I think it's reaching an all -time high and it's a net and the end it's a net negative if trust breaks down and investing. If trust leaves the system, it's just so much harder. There's so much trust in this system and it's not enough time to earn it and investing. Sometimes there isn't enough time to earn it. You can't get to know someone for four months anymore, even four weeks.

1:19:35You might have four minutes. So I wish a few more people went to jail. Okay. There's no consequences to standing up at a topic accelerator and saying we have millions of revenue and the next week, the revenue isn't there. There's just no consequence. And maybe that's funny to some people. I don't think it's funny. I think it's like Jeff, like founders used to, every founder, almost every founder used to have this ethical standard a few years back that I think has dissipated in today's world and it's just ramping greed. And I like the greed because it'll make us money, but there's too much of it.

1:20:05Disagree that it was good. And now it's I don't think it's, well, I think dishonesty ebbs and flows with greed. And I think you tend to see peak dishonesty at a time of peak greed. So you see more of them now, but I don't think human beings have changed. I don't think we're more mild than people 30 years younger than us. I think the truth is, you look at 1929, you look at the boom in the 80s, when there's lots of money to take, you tend to just see more fraud and no trial of opaling right now. As the first thing, I do think people who absolutely lie should suffer severe consequences up to an intruding person.

1:20:38I think, you know, so that's a general's concept. I will say all these cases tend to be very facts and circumstances. You know, ranging from, oh, you gave an example, we had contracts and they had updates, is NARR square one way it is, maybe this and all the way to forging documents, which is clearly illegal, right? So I think what the truth is, and I'm not going to comment on specifics because I don't know. I think it'll rain from you absolutely lied to you tall things in a way that's very poor you and they should have asked the right questions and you didn't. So my comment is myth, the league and you have a lawyer in the family, a criminal defense lawyer way back in the day, long since retired, but the average fed conviction rate for most crimes is 78 % plus.

1:21:24It's slightly lower I think for white collar crime only because you get lost in the details and the noise of what exactly is intent. So I don't think it's a layup But I do believe, as you say, Jason, some actions are just so far blatantly out on there. I just flat out lied. I forged invoices. Yeah, if you do that, you should go to prison because there's a lot of tax. If you can't rely on that kind of stuff, there's a lot of tax you have to do. So I'm not calling for vengeance and death, but I wouldn't be careful. That felt like a bit of a law and order lurch at the end there. Come on, say something nice, Jeff.

1:21:57Well, between Jason who wants some sort of venture capital ice regime, I actually think a little bit like if these sees are like so eager to get a deal done because they're like I can't I don't have time to even check any of this stuff then it does feel like that they're greed in that scenario Get rewarded with someone on a fraud. You're like well that that seems about right and there's a German word for that I'm sure here's the pattern that I see every time I read these like I saw this you know CEO of IRL abducted I've never heard of IRL actually and the pattern that I've seen is that that whenever I read these stories about CEO, founder, committed fraud or whatever, and they've took millions of bench capitalists, the pattern I see is I've never heard of any of the companies.

1:22:38Maybe that's just me, I'm an old man, I'm not keeping up with all the cool things, but there's this sort of thing, well, if I've never heard of all these things, maybe there wasn't a lot of real behind them, and they just look good on paper, because as a real human being operating the world, if I've never even read a story about these companies, let alone an active user of them, And something seems a bit odd. It's interesting comment, Jeff, your point. The commission of the crime is on the 22 -year -old who lies and they play the consequence. But there was a little bit of me saying the 40 -year -old running a lot of money who's sophisticated, who's running a big firm.

1:23:13They kind of owe the system the duty of care to check some of this shit and not be carried away. Yes, SPF went to prison, but he was relatively speaking a young man with a lot of hubris. and we've all been there. I know I was when I was that age. It would be better if the people who were paid for their judgment, exercised that judgment and a few times had slowed down here. Maybe we should have an order to people before we manage, you know, 50 billion of other people's money. The incidents may fall on the guilty, but I'm not sure the moral blame should be allocated the same way. Yeah. Well, Jeff, I have to say, dude, you have been a fantastic guest.

1:23:48Yes. Love it. I have loved I love having you on. I know Jason and Rory have done this. I mean, seriously, awesome. Thank you so much. Thank you very much. I actually stealing the little fucking three -way list. As you can tell, we have so much fun doing that show, but I want to make it the best show for you. So let me know what we can do to make it better for you. Harry at 20vc .com, I want to hear your feedback. But before we leave you today, let's talk about agents, specifically Piper, the A .I .S .D .R. agent brought 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 AISDR agent, wow it is here to help.

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1:25:53With ATIO, AI isn't just a feature, no no, it is the foundation. It's powerful, it's AI automations, it's research agents that transform your go -to -market motion. It's a data -driven engine from intelligent pipeline tracking to smarter product -like growth. Fast growing startups like FlatFile, Repplicate and Modal are all experiencing what's next. So get ready to build without limits and start now atio .com, forward slash 20 VC and get 15 % off your first year that's atioatti .com slash 20 VC. Okay pipeline sorted, woohoo! Now what about your own legal team? Enter LaGora. LaGora is the category defining AI platform that's fundamentally reshaping how legal work that gets done about fricking time, empowering lawyers across tier one law firms and in -house teams to achieve more with greater precision and confidence.

1:26:45So LaGoura does this by solving really concrete tasks such as document extraction, reviews against a firm playbook and suggesting well crafted markups directly in Microsoft Word based on your preferences. My word, that is a topic list of conversations that will not get a second date. But anyway, the adoption of legal AI is surging across the world and LaGoura is at the forefront of their shift as the chosen partner to 250 industry leaders in law across more than 20 markets. The likes of Goodwin, Bird and Bird and Deloitte are making daily use of LaGoura platform to review and research with precision, drafts smarter and collaborate seamlessly.

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From the publisher

AGENDA:

[00:05] Musk’s $1 Trillion Pay Package: The Breakdown?

[00:15] Scale, Windsurf: Are Founders Just Mercenaries Chasing Cash Today?

[00:21] Ramp at $1B ARR, Brex at $700M — Is AI Causing All Boats To Rise?

[00:26] Sierra at $100M ARR Worth $10B — Bubble or Brilliant Bet?

[00:30] Kleiner Perkins Invests $100M into Anthropic at $183BN… WTF?

[00:36] $10B in OpenAI Secondaries — What Happens When 1,000 New Millionaires Hit SF?

[00:40] Anthropic Pays $1.5B to Authors — Fair Deal or Pure Piracy?

[00:44] Why Did ASML Just Invest into Mistral at $14BN?

[00:52] Atlassian Buys the Browser Company for $610M — Genius Move or Panic Buy?

[01:18] IRL CEO Arrested for Fraud: Is More To Come?

 

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