20VC: Opendoor's CEO on The Greatest Turnaround in Tech | OpenAI and Oracle: How Can Either Afford to Do This | How Anthropic Could Lose 50% of Their Revenue Overnight | Replit Raises at $3BN | Figure, Gemini & VIA IPOs Broken Down

18 Sep 2025 · 1 h 24 min

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Podcast Summary: The Twenty Minute VC (20VC) - Episode on Opendoor and Industry Insights

Episode Overview In this episode of The Twenty Minute VC, host Harry Stebbings interviews Kaz, the newly appointed CEO of Opendoor. Kaz discusses his transition from Shopify to Opendoor, the challenges and opportunities within the home buying sector, and his vision for the company. The episode also touches upon recent developments in tech IPOs and examines the evolving landscape of artificial intelligence partnerships among major corporations.

Key Topics and Insights

Opendoor's Market Potential

  • Valuation: Kaz believes that Opendoor is fairly priced in the public market for its potential, emphasizing the vast market opportunity in real estate transactions.
  • Business Model: He insists that the mission to simplify the home buying and selling process will drive profitability, distinguishing it from merely seeking short-term financial gains.

Kaz's Transition from Shopify to Opendoor

  • Conviction: Kaz left a secure position at Shopify, where he was well-compensated, to pursue what he believes is a significant problem to solve in the real estate sector.
  • Salary Structure: He disclosed that he has opted for a $0 salary with a long-term stock-based compensation structure, highlighting a commitment to aligning his success with Opendoor's performance.

Meme Stock Phenomenon

  • Kaz expresses concerns about Opendoor being viewed as a "meme stock," but he insists that the company's fundamentals and potential will ultimately drive its success.

Partnerships and Industry Trends

  • Oracle & OpenAI: Discussion around the recent partnership between Oracle and OpenAI raised questions about the financial implications and risks involved.
  • Microsoft's Strategy: The episode analyzes Microsoft's shifting strategy regarding its relationship with OpenAI, hinting at a more transactional relationship moving forward.

Upcoming IPOs and Market Movements

  • Recent IPOs: The episode highlights the recent IPOs of companies like Replit and Figure, noting the significance of this being the busiest week for IPOs since 2021.
  • Market Comparison: Kaz compares Opendoor’s potential to other disruptive businesses like Carvana and Tesla, emphasizing the importance of operational excellence and execution.

Challenges and Future Outlook

  • Kaz acknowledges the difficulties in pricing and valuing real estate compared to simpler commodities like cars.
  • He outlines a vision for Opendoor that includes leveraging AI to enhance operational efficiency and customer service, aiming for a transformative approach in the real estate market.

Industry Speculations

  • Anthropic's Revenue Risks: The discussion pivots to Anthropic and the potential for rapid revenue decline due to competition and advancements in AI technology.
  • Investor Sentiment: There is skepticism in the market regarding sustainable growth, with many companies experiencing inflated valuations without solid underlying financial performance.

Quickfire Predictions

  • Adobe's Future: Predicting whether Adobe's share price will rise or fall in the next year, the panel expresses concerns about its ability to compete in a rapidly changing tech landscape.
  • Opendoor's Stock Price: Predictions vary, but there is optimism that under Kaz's leadership, the stock price could appreciate significantly.

Conclusion The episode provides valuable insights into the evolving landscape of venture capital, technology partnerships, and the challenges faced by companies navigating public markets. Kaz's candidness about Opendoor's ambitions and the broader market context illustrates the dynamic and often unpredictable nature of the tech and real estate sectors today.

Key Takeaways

  • Mission Over Margin: Companies should prioritize their mission to create value over mere profit-seeking.
  • Importance of Execution: Successful execution and operational efficiency are crucial for long-term sustainability in competitive markets.
  • Market Vigilance: Investors must remain vigilant about market volatility and be cautious of inflated valuations that lack solid financial backing.

The episode wraps up with a reflection on the importance of feedback and audience engagement, with listeners encouraged to share their thoughts and suggestions for future episodes.

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Transcript

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0:00Open Door is priced in the public market for its potential and an incredibly fair price for the potential. Look I think that bull case for Open Door is obscene. Just obscene. It is hard to exaggerate how big this company can be. I'm no one's idea of a professional manager. We're going to create alpha. I think corporate executives should basically only get paid in options. We're going to launch things that won't work but we're going to start fucking launching things. This is 20 VC with me Harry Stebings. It is my favorite show of the week, Jason Lampkin, Rory O 'Driskel, and we have the Hottosio in town, OpenDaw's new CEO, Kaz, who just joined from Shopify.

0:37He joins for his first ever interview as CEO of OpenDaw. He did this show when he was just 24 hours into the seat. On top of that, we talk about OpenAi's relationship with Microsoft, their new deal with Oracle. We talk about the IPOs that happened last week, the busiest week of IPOs this year, and so much more. But before we dive into the show today, let's talk about agents, specifically Piper, the AI SDR agent brought to you by Qualified, the agentic marketing era has arrived, and if you're a B2B marketing leader looking to scale a pipeline generation, Piper, the AI SDR agent, wow, it is here to help.

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3:17Tech leaders set policies and oversee usage. Business teams get the models they actually need. Try it yourself with a 14 -day free trial at Nexus .ai -4 -20VC. You have now arrived at your destination. Guys, I am so excited for this. You all know it's my favorite time of the week. My mother even loves these shows now, which I think is incredibly heartwarming because she listens to everyone But we're gonna start on news item number one Kaz from CEO of Shopify to now CEO at Open Door Kaz first, thank you so much for joining for this first little stint. Thanks for having me I appreciate man I wanted to start with the question you left a great and huge business in Shopify you must have the ultimate conviction that I buying is a good business.

4:06Can I be so blunt as to ask what led that conviction when it's been a challenged conviction to have over the last years? I never thought I would leave Shopify. I thought it was gonna be like my job forever and I just genuinely loved the company. You'd love Toby. Love what it stands for. When I joined Shopify everyone was like what the hell are you doing? This is a tiny company that's gonna go nowhere. It was among the most shorted stock in the tech market. It was like very much like this thing will fail. In fact, it was like a very lot like I think Citroen wrote in a short report the day I joined Shopify about how terrible business it was and how it wouldn't last two years.

4:43But I think Shopify's a wonderful company. But look, the fundamental problem that opened Robel's solve is an incredibly important problem not just as a business but for the world. If we can make buying selling and owning a home easier, less frictionful, less terrible. The world will be a better place. We will figure out how to make money along the way. This will be a great business. Like we will make money. This will be a great business. But the problem space is a valuable one to explore. And I think you need to do it unapologetically. Like the goal here isn't to like minimize risk. We have a mission to go after.

5:18We'll go after it incredibly aggressively. And we're gonna make it easier for both people who are buying and selling homes to engage in that transaction because it matters to future of our society. Can I be so bold in just us? Does that not feel like a bit of a boom time mindset? Oh, it's a valuable problem or figure out how to make money along the way. Fuck no. No, definitely not. Look, this is not like, I'm not saying we're going to figure out how to make money along the way. We will make money. That's not what I'm saying. We will have plans to make money and we have like some couple good bets already will launch more of them.

5:49I'm not saying I have like a hope and a dream of profitability. This is a for -profit company. Like it's very much a for -profit company. We'll figure it out. But what I'm saying is that businesses should not exist to make money. Businesses should make money to deliver on a mission. And those are important things. We are a mission -driven company and will make a profit such that we can deliver on our mission. And like the shareholders will be happy, buyers will be happy, and sellers will be happy. But that's the goal. Like I'm not saying like, oh, I don't know how to make money. I know how to make money here.

6:19What I'm saying is, the mission is more important than the money. A wildly successful software executive. How do you deal with this meme stock element to the company? Like, I'm not a meme stock guy. I don't trade. I'm long and everything. This isn't GameStop, but it's crazy. This memeish -nish pre -u is crazy, isn't it? I'm not a trader. I own literally one ticker. When I was at Shopify, it was Shopify. I expect I will own two tickers for like the next whole year. Shopify it opened. Like I'm not a diversified trader guy. That's not what I do. That's not my job. My job is to build great products and get people to pay for them.

6:53The second thing is I actually fundamentally reject a premise. Open door is priced into public market force potential. And it's an incredibly fair price for the potential. And I think we will earn the potential. We're gonna go get executed against the potential. That's not that different on how startups are valued by VCs. You don't value the current cash flow of a company. You value the potential and say what are the odds it will get there. Was it this kind of cash flow odds of this with this thing being big? If you do it that way, this is a single largest market in the world. I think Tesla was not above 10 % in any market.

7:29It was selling cars in it made until last year. It is above 10 % in some markets this year. Open door was above 10 % in many markets it was selling homes in a couple years ago. Like we will get back there. It's a significantly bigger market. it significantly higher attach opportunity, significantly longer ability to have a relationship with a buyer and a seller. By the way, I'm a math nerd, right? I was a math thief growing up. If you do the math on a potentially company and just discounted back, I think of stock as reasonably priced, I would have bought at this price. In fact, I did buy at a higher price than the current price.

8:04The meme stock thing is actually two parts to what those they price well, to value. And then there's obviously the combination of meme stop and activism. And I think the interesting thing here is a set of investors from outside have been able to agitate and drive change. In this case, I think very interesting and good change. This is what the evil activists would be like to say with VCs. And it was just kind of fun from a distance to watch it. Just rattling the cage into the board and saying you need to do something different. And eventually the board said, hell, you're right. Let's do something different.

8:33Let's call cows and put these other guys back on the board. I think you're absolutely right. Look, I think that bull case for Open Door is obscene. Just to just observe, it's hard to exaggerate how big this company can be, but companies require good stewardship and operational excellence in aggressive execution. There are companies that can be run by professional managers. If your budget factory, professional managers are great for you. If your software factory, professional managers are the death. I'm no one's idea of a professional manager. So we're going to create alpha. Are you a software factory, though?

9:07But you have a lot of real assets on your books. You have a lot of it, I think, with assets on your books. This is a very real world, real world, financial mechanics business in a lot of ways. It's not a stuff like that, actually. I disagree. I fundamentally disagree. Open door is a software company that happens to have some assets. I think there's an asset light model here that could work incredibly well, because asset heavy model that can work incredibly well and will have literally all of them. You must judge companies based on where leverage comes from. You look at a company like, like, ah, that's where leverage comes from.

9:39The leverage from open door will come from software. We will build excellent software for buyers and sellers of home and owners of homes. And we will attach services to those products. And one level down, because on that, because there's two things you do, you have to be able to predict the price of an asset. Well, maybe through it, you've got to have a top of funnel to drive in buyers and sellers. You've got to have a really big AI brain to figure out what these assets are worked. And then you've got to have transactional efficiency to make all the shit happen, like the processing, the selling, the repairs, all that.

10:11And maybe those two things are the soft, what you're calling the self for, actually. Which do you think is the hardest part, which do you think is the most important part? So I think the last part is very software enabled, and generally I'm actually 24 hours and 12 minutes into the job. Yeah. I'm generally impressed by the last part of business already. It could be significantly more software enabled, significantly more AI enabled. I've actually generally impressed. But I think the looked a long -term leverage for this company becomes offering a fair price for home. Not trying to make all your money on buying homes at a discount.

10:42That's just like no one wants to sell a home for a fair price and adding value added services on top of it. Adding things at home owners and home sellers want as a part of transaction and they have earned, you've earned the trust because the price is fair. The house is good. It's valuable. You're not selling lemons. We will get to a point where you will buy a home from Open Door. I'm not saying tomorrow, but will you be able to buy a home from Open Door? And if you don't like it, you'll be able to return it. We'll get to that point. We'll get to a point where you'll be able to buy a home from Open Door and we'll stand behind it for the life of that house.

11:17And you'll be able to treat it as though it's a guaranteed asset that we will take care of and take care of you as a buyer of that house. As a seller at home, we'll be able to get to a point where we will find your new home. You don't have one quick, we'll find you a new one. Like we will find a way to make the liquidity work in the long run and we'll focus on both buyers and sellers. For what it's worth, this isn't unsharked territories in the public markets. Carvana has a very good model of this. We offer a fair price to buy our fair price on a seller, make margin on added services. First of all, make big picture comment.

11:48I think this is one of the hardest business models out there. I totally see the upside, but truly we look not at open door, but some of the others. This is one of the most challenging problems I can imagine because you know, you made the Carvana analogy and it's fair. I mean as people know Carvana was another high flyer in 2021 selling cars doing the same thing for cars Flamin 'in in 2022 investors including thrive hell bought some more stocks up well -nought of 10x Everyone looks really smart to hell than bored and obviously if I was you that is the mental model I'd be pushing all day every day One of my many nagging worries on this is it's easier to price a car than a house, right?

12:27The nuance you have to get right. Put me on one. You can get within 7, 8, 9%, pretty accurately on Combs, but it's the little shit that when you walk around the house, oh, they have an X, that gardens nice, it seems to me the last 8 % of price, which is where you make all your margin, has a lot of right, and I could be wrong. But that seems to meet the hard part of price. I think you're wrong. Cool. I think you were right. I think you were right three years ago. Yeah, I think three years ago This was an incredibly difficult problem that required human beings to visit homes and look around and look at the shape of the So it's like that's the real thing if your one side is straight that has a slope their side doesn't have to Stop those two things are priced differently, but there's a reason like God invented AI This is solvable problem today like we don't need to limit ourselves to what human beings can see This is a real thing human beings are various creating machines like we can build software systems to solve these problems You know what the funny thing is?

13:21Shopify is a notoriously bad business. It's a high -churn business selling to small businesses at a massive discount. You could spy Shopify for $1 .1. It's a SaaS product you can buy for $1. There are no seats. There's no seat expansion. Shopify is a best deal in SaaS. We can buy a software that's the best deal in SaaS. Shopify makes we make our money when you succeed. I even serve as a Shopify. Why? OpenDraw will be the best deal in buying and selling homes. And we will make our money by adding value to those homes in ways that other people cannot do because they don't understand a home, they don't understand a buy, they can't underwrite a risk, they can't provide additional services.

13:58The problem with having to make all your money in one transaction is that you buy necessity have to be shady. Correct. Right? No. This is why I use car deals. I use car deals. I use car deals aren't awesome people typically because they have to make all their money in that one half an hour. Whereas if you make my money, your money in the long run from a long lasting relationship with the counterparty, you have an incentive to do right by each other. And this is actually a key differentiator of what we will do. We will create a network for buyers and sellers, homeowners, home buyers and home sellers, where they will have a long -term relationship with us over a series of products we will launch.

14:34Some of them will be free just because they're good. If some of them will not be, I will make money on them. Title, mortgage, does a whole bunch of things that happen right there that are widely profitable on top. I mean, title insurance is the world's best business because no one ever pays out a claim. How do you think about the law of the estate agent in this? Because that law is changing also, and obviously it's 6 % in a world where you make an 8%, and how do you think about how a estate agent sit in? Look, I think there's a structural issue to being to think through, which is this. Transactions and relationships that have many intermediaries are typically not great ones.

15:07Yeah, it's just not awesome transactions usually I usually want to look to person you're dealing with in the eye and deal with up But that's what real thing is now Do I think there's a place for experts to help either side? Yes in some cases, but not in all cases in some cases you will I'm not dogmatic about this But I do insist on an excellent fucking product like an excellent product that a buyer and seller can use and be proud of Now, if some sort of buyers and sellers want to have someone else help them, great. But we will provide an excellent service to buyers and sellers. And if in some cases, we will have other people involved.

15:43And that's fine. I didn't really fully get the Shopify analogy, just then. But Shopify is only 25 % of its revenue from software and going down, right? It is the cheapest. It's the best one of the best deals out there. I mean, maybe chat cheap. It is a better deal. But they've got to earn the other 75 % through Merge services and others. Yeah, during it. In three years time, Will you have more of an asset light model or will you more be an asset heavy model? I mean the company doesn't have an asset light model right now. So yes by definition yes. Whatever you can choose to stay an asset heavy or you can choose to translate that.

16:13We will not. We will not choose to say that and solely asset heavy world. Look guys, I'm not publicly traded company, etc. I don't have a magic plan that I'm executing against right now. This is 24 hours and 19 minutes now. But we are going. We have more minutes. Last 19 has been wasted. He's mentally saying to himself, for kids going, guys. I think what you need to do is look at the problem space and solve all of it for the user. To look at the problem space and solve all of it. It's incredibly hard to build good products. Therefore, it's incredibly hard to build good businesses if you're solving the tiny problem that you happen to think is profitable.

16:51But if you do that, you end up with adverse selection. Yeah, like the market eventually clears properly and if you think for a very long time You're gonna have 20 % margin buying homes cheaper than someone else. You're just straight up dumb The market eventually clears appropriately What you need to do is being incredibly efficient on the first transaction and incredibly valuable on every transaction Thereafter and that's our job here and we're gonna get there like it's gonna take us a second We're gonna screw up a bunch of things up. We're not gonna be perfect we're going to launch things that won't work, but we're going to start fucking launching things.

17:25Katz, how did the discussion go? It's quite notable that you aren't taking a salary pretty much, or like $1 or whatever it is. I would think less, I'm not allowed to. I'm not allowed to take the less than $1. I would try to take the less than $1. So when you hit 30 bucks, you get a lot of money. Reminerated. If I could make it the following way, I would have made the following way. I think corporate executives should basically only get paid in options. I think it's a very weird world where we create incentive for corporate executives to be bad at their jobs just to get paid. I think it's just so fucking weird.

17:56Or like the thing you have created is be inoffensive enough not to get fired. That's very weird. That's RSU life. I own NO RSU's. Zero. Actually zero. Literally entirety of my performance money is based on the stock price going up and like those different cliffs. Some of it is like a phantom option where if a spark price goes down it's worth zero. Some of it best based on price. It's like, this is a complicate because it's very odd, Delaware and SEC rules, but I would have gladly taken just options. In fact, that was my preferred state. But we have tried to construct a thing that looks just to options with some upstacks, some vesting over time with stock price.

18:32I don't have, yeah, who finance on my laptop. I will not look at the stock price every day. What I will look at is delivering value for users and shareholders of this company over a long period of time. And that's what we're gonna do. like I think this company is incredibly valuable. I thought when I joined Shopify that the market misunderstood the opportunity, I think the market massively misunderstands the opportunity for Open Door just like by order of magnitude. Can I ask how important do you feel it is that you have Keith and you have Eric coming back into the fray as well? Wouldn't it have taken a job, would not have taken a job without them.

19:06Like a strap wouldn't have been it. In fact, I said I won't do it without them. We're going to do things that look odd but what they look isn't important, what they are is important. How things look is less important than what things are, and we need people who will be with us while we're in the picture to take those risks. I think that's super interesting and it actually the whole private versus public thing, right? And there was a super out of New York Times recently on it, basically why it being public is a pain in the butt. And I think you're exactly right, Kat. This is a refounding of the company.

19:36And if you didn't have that air cover from those guys coming on, it's just really hard for a standard corporate board of a public company to do the kind of pain you're going to see in the next 12 months to turn this thing around. So I would agree with you. I think that if I was advising someone as a CEO to take this on, your first question shouldn't be where is your air cover from entrepreneurial people, not the kind of people you find doing the public board for 200 grand, who will allow you to do this? Because if they're not going to, if you don't have that, invariably, you like the poor guy at Intel, you have this big ambitious plan, you tell Evan on the board, you have this big ambitious plan, they all agree.

20:11And then one year and it's like, oh my god, it's terrifying. We're out of here. I think you're exactly right. And it's a rare combination to be able to fix the, I won't say fix, to orient the board around the task at hand. We have great board members, but I viewed them as colleagues and coaches. There's a board member who's coming into the office in a couple hours because we're going to go through literally every house we own line by line together. With that board member, we're going to sit next and we're going to go through everything. Like, one of the first things I did was I got the board member and I went through literally every invoice the company had paid for the last 12 months.

20:42Actually every single one of them, I've reviewed every line item. Our board members are going to join us along this mission and they're going to work as hard as we do. I'm incredibly excited. Do you want your math to come back into the fray? The world can't have enough Canadians man. It's a real thing. The man wins, Cubs wins, that was a killer answer. It was good, he's well trained. Find a one for me and then we'll let you go. When you made the decision, you have a huge amount on the table at Shopify and you left that for this. How big is $100 million? A few hundred million dollars, exactly. You believe that you will make more here and what is that upside here when you did that evaluation?

21:25Look, I don't optimize my life for money. I just don't. When my wife and I got married, we would optimize our life for living a dent under world. We will leave a dent on the world and that will be optimized our lives for having said that I'm Incredibly bullish on the bet. I would not have taken it if I didn't think it was gonna pay off I'm very very bullish on the stock. I'm very bullish on the company We will build and this is my ask of everyone who has bought the stock and is cheering us on We will build a generational company here and they must hold us to account for doing that But we must do both things.

22:00We must build a company that makes the world a better place and we must deliver a shareholder value. And both those things are incredibly important. And I'm generally like, I'm asking people who have bought this stock in hope that we will do the right thing to hold us to account and call us out when we don't do the right thing. This man has put his money where he's mounted. And that's pretty damn impressive. I mean, you really have. You've walked away from an exciting, challenging, extraordinary well -paid, very manageable, safe gig to double down on as I say it's absolutely child drink problem so it will be fun to watch you figure it out.

22:34I optimized my life every at ediv every week I write down a note to myself was the week hard was it valuable was it fun at the end of every week I judge my week based on hard valuable fun. That's a goal every every week to have all three I find you can't have fun unless you have the first two I had my first all hands yesterday in the company I told the team that we would value this company's next year over a hard valuable fund. I don't know where the offices will be. We're going to figure that out this week. We'll announce them to the company on Monday and to World on Monday. Open door will be the most aggressive in office public tech company.

23:07If you are a builder, if you want to build a future that is better for home owners that tilts the world towards owners rather than renters, find us. We're gonna build an exceptional team and ship exceptionally fast. My deans are open, send me the M, I don't know where the offices will be, I will know on Monday, but we'll figure it out. Kaz, you are here, man. Thank you so much, thanks for coming. All's coming your second day. You are here. Thanks guys. Thanks guys, have a great day. Good job, that was awesome. Thank you, man. Thank you. It's lovely to see you guys. That was a great start. It was cool.

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23:41We're gonna get back to normal programming, baby. and I want to start with Oracle and OpenAI, Oracle touching a trillion dollars. You're always quite good at setting the scene and I actually got given some good feedback the other day, which is we need to set the scene for the stories. People love the analysis but they like to know actually what happened. Can you just help set the scene of Oracle OpenAI? What happened? Sure, and I think it is good feedback. We often do forget we dive right in. So step back. What happened is Oracle announced I want to say that whatever was Q2 results they have an off year they have an off cycle year so might have been Q1 and for what it's worth they're actually a little light on the quarter's results but they announced a future RPO revenue performance obligation of north of 300 billion dollars.

24:26In other words they said we've got orders as of now that we have to deliver in the future for well north of 300 billion dollars and they didn't say this but you figured out that most of which is a big open AI order for around 300 billion of future cloud compute for their AI platform and the stock exploded. The stock went up 36, 38%. I think briefly making Larry Ellison, the richest man in the world, Yeh Larry, and Oracle Touch of Trillion dollars. It's unparalleled for a top 10 company to jump by 38 % in one quarter. So a huge jump since then some skeptical go commentary, but that's what happened.

25:03How did we analyze it then subsequently? How did you feel when you read it? Because as you said, that was skeptics. How did you feel? I suppose a little skeptical, but then try, I mean, positive spin. If you believe the revenue 300 billion, let's just say if you think open AI has 300 billion to spend, plans to spend it with Oracle and does in fact spend it over five years, that's 60 billion of revenue a year, the wide by five. So even at a five or six times revenue multiple, that gets you to 300 billion in delta market cap, which is exactly what happened. So if it's a hundred percent money good, and you know, you can say it's some kind of recurring revenue there after, then it kind of roughly corresponds to the increase in value.

25:46It's just that then you say to yourself slowly, the customer promising to give you 300 billion dollars is doing 12 billion and revenue has raised, I can have 40 billion total life to date, is still losing significant money. And therefore it's going to have to raise, as Sam Altman has said, a couple hundred billion dollars, he said 115, but who's counting, to be able to pay you that money. So you look at new go, this is a very levered bet on everything at OpenAI working. So to some extent, it's kind of like a proxy OpenAI stock. It's like, I can't buy OpenAI in the public markets. So if open AI is successful it will have 300 billion.

26:24If it has 300 billion it will give it to Mr. Vales and if it gives Mr. Vales and the stock will go up by Oracle. It feels plausible but non -risk adjusted. You're applying 100 % certainty to two or three things each of which have a fair amount of uncertainty associated with it. That was my kind of net takeaway. Have any of us given up caring whether any of this revenue is profitable? I think the bet that open AI can come up with the money as a reasonable one. They may not, right? There's some risk there. But so far, Sam has found a way. Jesus Christ, core weave in everybody, these days they said they have insatiable demand, so that's okay.

26:56But no one cares that this adds nothing to Oracle's bottom line and may never. No one cares that Oracle is basically a fungible set of server services for folks that don't want to bother to bring it in -house. I mean, this is for the first suitable future as zero net margin business for them, isn't it? It's good for VCs. Like, we don't have to look beyond the top line. It makes our lives much easier. We don't have to worry about these silly things like inference costs and gross margins because the public markets don't care anymore. You are right. From the purpose of, I'd say, five or ten years from now, the people selling cloud computing to the people who own the models will probably not make as much money as the people who own the models.

27:35That's a pretty obvious statement, right? Even though OpenAI is losing a lot of money now, they are commodity provider of services to them, exudes over the medium term, being an even less, bigger, more commoditized, less profitable business. I prefer to own OpenAI than CoreWeave, and to the extent that this is just CoreWeave 2, you're totally right, Jason. Now, the fun thing is, we are dealing with the man who most successfully on the planet extracts operating margins from software companies, which is Laoye Allison, and that's why he owns 41 % of this band thing up from 27 % a decade and a half ago, getting that free cash from recycling it back.

28:10But you're right, this does feel like getting 300 billion in revenue until your point Jason in return for which you have to spend a whole buttload up front on CapEx in return for a business that whatever however profitable it will be and maybe it is profitable It won't be as profitable as the 41 % operating margins that they currently get some selling databases So I agree even after it's nothing today isn't it? I mean literally this business is consuming cash I'm sure well, yes And you probably have some kind of positive account in gross margins but really it's all about the assumptions you're making on your CAPEX depreciation.

28:43And if you know over how many years you should appreciate the latest Nvidia chip, then that would be the key question. This isn't a bunch of memeers getting excited about CoreWeave. This is Oracle. This is a company founded in the 70s where the public markets are like, we don't care that your new GPU hosting a product, which has massive top line growth, right? We don't care at all that it's contributing nothing to the bottom line. We don't care, we don't care even in Ayodas what the public market said, didn't they? Wait, no, you are, it is just in your, just as it is, you're exactly right, is that?

29:15I mean, I think it's equivalent, but with more success than the Facebook slash meta story. You have an existing business. It's freaking awesome. It's nothing to do with AI. It kicks out 41 % operating margins for Oracle, high 30s, 40s for Facebook. And the market is saying to you, if you got out at free cash flow, have had it been, guy throw it back in, see how it goes. You know, in the case of meta, they're not penalizing him and in the case of Oracle, they're actually rewarding him for doubling down on unpopular growth. So entirely rationally, he's doing it. It's got to feel frickin' great when you've been crankin' like that guy has for 50 plus years.

29:51Whatever it makes long term for the stock, the fact that you sprint to the head and for a brief shining moment, the richest man in the world, probably that alone is worth whatever future damage you've done to your operating margins. It's great. Is this not an ultimate sign, though, of where public market irrationality and exuberance is? That Sam Altman and this announcement says that, with the margins associated to this order and it jumps 38 % at this scale, is that not the height of irrationality? You mean unlike our silver careful and your silver mind and private market VCs, yeah, I'm shocked to discover gambling going on in the stock market, how are you?

30:28Yeah, it's pretty See, Fawty? Look, there's a fourth of the private markets for AI for two or three years. And probably the public market is saying I'd like to get in on the game and this is one of the few ways to play it. So, I agree. It's Fawty. Is it more Fawty than any of the things you're seeing or I'm seeing? I don't know. Who am I to judge? The one thing I do think is important. We mentioned the margin element. I have never before seen such lack of investor diligence on anything except top line revenue growth ever. Estonishing where it's not included in an update, hundreds of millions of dollars wide, without a discussion on margin.

31:05Number one, and then number two, it's just like growth is amazing until it doesn't grow anymore. And when you look at this for open AI to pay this, if they two acts between now and July 26th, and then two acts again between July 26th and 2027, they'll be at 48 billion and still 12 billion short, per year to do this. At some point, the growth does taper. agree. Do I think they're going to collect 300 billion dollars in orders from OpenAI? Absolutely not. They're also. I don't think that turns in. I think they've got the business. I think they'll get more revenue from OpenAI. Do I think the full of last 300 billion dollars will be wired in five or six years now?

31:45I've vanished out of it. Is this market not just all about shouting as loudly as possible? Drummer's Stargate. We're gonna have $500 billion. What happened to that? $500 billion. It looks like there's a lot of... Has really cynical question, isn't this one of those where everybody just announces the same thing? So yeah, it used to be soft bank, but wasn't Oracle part of that? And maybe now this isn't. Larry was right, Larry was, it did happen. This is a big part of it. You think Stargate. You think Stargate. Honestly, to me it's a reminder, we've talked about this to really scrutinize Sam to see the future, because he goes to Trump, right?

32:16And he's got son from Softbank and Larry Ellison in that awkward photo. Let Musk wasn't there when he was still running things, right? This was a couple of months ago. announcing the target thing I'm looking, what's this uncomfortable Larry Ellison who hasn't put on this, doesn't look like he's put on a suit in three or seven or eight years, sitting there squirming in the White House. This was, we should have bought Oracle stock that day. Like why we didn't put the whole fund into Oracle? Because why did Sam make him come? We got to do this, right? That was a telling moment to me, but I didn't get it at the time.

32:46This just seemed like the oddest photo op and it seemed like dissy and Elon Musk, but it wasn't that at all, right? This was the future. I mean, I think one of the things that's obvious from this is that everyone is getting what they want from this press release. Arcula is becoming the richest man in the world because his stock is going up 37%. Yes, Sam Altman is getting frankly leveraged in his negotiations with Microsoft by making it clear he has another CapEx provider willing to spend vast amounts of money. So the sum is that this is happening because everyone involved wants it to sell and I'm willing to bet they wanted enough that they're not sitting there going, are we 100 % sure this is going to happen?

33:22Or do we just have a credible case that says this might happen and it will be good for us in the short term to be fair, especially when you're trying to do something as ambitious as OpenAI. To some extent, momentum is your friend. The momentum is a necessity. And things like this just keep building on the momentum and keep building on the sense of inevitability. And you write how it's the role of investors to be a little more cynical and scrutinized and say, do I really believe that that's going to turn into $60 billion a year of revenue? Do I really should I really mark Oracle up by that amount and clearly they forgot to do that this week?

33:55I just it may be a broader point But I just feel like the whole van should landscape just move from a game of investing to trading in a way that we're all just Hoping that someone pays a more irrational price than we paid and suspend this belief in the meantime You've got a couple I think we saw a couple good years until something happens. So might as well play the game Are you going to be the Chuck Prince of our generation member? you know, while the band keeps playing, you gotta keep dancing the CEO of CityCore in 2007. Jason, you might regret that quote. I've got dancing with Hopin B real and Clubhouse and you know, the party stops.

34:30I'd rather don't thought that. Yeah, but what happens along the way is there's exits. Yeah. So I think the big question for venture, I think where we're gonna make a lot of mistakes in venture is not taking billion dollar exits over the next 24 to 36 months. We're gonna triple down. We're gonna have, there's gonna be board members, Rory. We've got a $4 billion offer for our latest AI tagging categorization software. It's what, 3 % gross margins. Let's not, I want eight. Or 12 would be better. You know, it's better than 12, 24. We're gonna say no to those fun returners and we're gonna wake up and they're gonna be worthless.

35:08I think that's what's gonna happen. It's because if you're in the game now, you gotta have a couple big exits and IPOs in next couple of years are quit the game. You got to have a couple. First of all, you are right that that will invariably happen. I mean, we're actually, look, we're just at that stage in the cycle where you've got a large amount of euphoria fairly untethered. And, you know, the positive spin, which I think is true, is you don't make these kind of technological leaps and technological investments without a fair amount of accompanying euphoria. This is a means to the end of moving the needle forward on AI.

35:37We got to try a lot of stuff, a small amount of it will work, a large amount of it will fail, and a lot of money will be lost in the end. But the good stuff will ultimately outweigh the bad stuff. This is the way it happens. But to Jason, your point in particular, I'm around line at I remember a bunch of those companies in 99 2000 where you know you got the offer for two billion for some fiber optics company or for some Com equipment box and the board said dammit. We want eight. We're turning it down and then you'd meet the team two years later And the companies were zero and most of those folks were shell shocked It's like, you know, winning the lottery and then losing your ticket.

36:12It was brutal. So I think being canny and true about what chips you take off the table in the next couple of years, I think you're exactly right, Tristan, would be a key part of the game. I also think people mistake valuation for liquidity, which is like just because it goes up. It doesn't mean you can get out. And if you can get out, it's often a discount to that priced round. And if you can, it's often an a strip where they'll give you 10 or 20%, but you can't get out as much as you could selling it all now. I don't think people think about that enough. True. And I think one of the things we're going to discover is when all this action was happening in the public market, you had this weird somewhat positive phenomenon, which is everyone up with constant liquidity, you know, you can buy in at 80 bucks a share, it goes down to 70 and you can say, I was wrong, I'm out and someone else thinks I think it's going to be okay at 70 and they go out and they're wrong and it goes to 60 and you can kind of parse out the pain among various investors who come in and out of the stock.

37:07The interesting thing on the private side is you've bought in high and the whole point of private is there is no meaningful liquidity and if you're wrong you're going to own it all the way down. It's going to be a lot more fun on the upside and a lot more pain on the downside when you don't have liquidity to fulfill the part of the role of liquidity is allow you to alleviate risk. That's just a game we're in and that's just the nature of being private for longer. Every single founder this year that has had a strong M &A offer, I've told them to take it 100 % of the time. Now I actually don't necessarily want them to take it.

37:41I don't want to be the guy saying I want to double down and quadruple down. I don't want to be the guy that a couple years later it didn't work out. So I'm telling them to take it. And if they come back and say no, I'm confident, here's my new heuristic, it's so simple. No, Rory, I'm confident it will be worth 10 times as much. No, I'm confident we will IPO. I'm confident like has just left hundreds of millions of dollars behind to Shopify Okay, right or wrong that dude's confident. We just heard it. No, it's not all about the money Okay, but he's confident this was the right decision But I'm telling the opposite I'm telling every founder take it take it take any massive offer take it and I want them to come back and say F.

38:19No way it's gonna be bigger. I don't want to have any of those regrets and I think it's the right telling them to do that make sure that I don't screw it up as a GP. It's just so easy when times are good to say, oh Oracle's gonna get another 500 billion, aren't they? I don't love your sentence, but I actually think it's right. Your advice should at some extent be tempered by the time. The Bayesian prior on a time like this when valuations are at an all -time high should be some version of what Jason said. Now it's still possible that you're the one in ten for whom an all -time high is just a step on the journey and maybe you should play the game out because you're so confident it's going to be amazing.

38:56I mean, look, it's very noticeable that three or four times in the last year you've seen significant M &A driven by founders at the same price that VCs either had just invested or were about to invest. In other words, that's the founder's saying because the VC member is investing thinking, oh, you're worth two billion. I'm going to give you money at two billion. I think you'll be worth six. And then three weeks later, the founder is saying, you mean I can actually get the $2 billion I'm out of here. Right? I mean, to some extent, that happened at scale AI. I think it was appending off for on windsurf.

39:26And that's founder Jason maybe listening to you and being fruit and saying, I could be at a local maximum here. This is a good time to take the chips off the table. And there's a little bit of information in that about how much dare I say it more true to they are about the value of the asset than the investor who is about to try to check at the same price. I completely agree. I was thinking it goes back to incentives and how investors to what we said last week with Jeff have many options and you know we want to ride them as much as possible and founders have one and it's their whole net worth in it and that drives a lot of decision making.

39:58I'm sure tied to that. I do want to be cognizant in terms of how we discuss the topics we have on the agenda. We mentioned Oracle and OpenAI. Microsoft and OpenAI's relationship is slightly changing it would seem. Announcement of Jason, why and you give a snippet on what this is in terms of the news between their relationship and how. Listen, we have more to learn. It is, it's going to be interesting. I mean, Microsoft, I think today, said they're moving not just parts of office to Anthropic, but that it is the default choice for several other products. And that Microsoft today said several months ago, they told their teams to start using Cloud Code, several months ago.

40:34So they've been breaking up at some level for a while. And I guess it's fine. I guess it sounds like OpenAI is gonna get what some of what they want. They're gonna get this revenue share reduced. They're gonna get their freedom to partner with whoever they want. And I'm not quite sure what the price and blood is gonna be back the other way. But already Microsoft's moving on. They're already moving on. They got the IP. They're gonna keep the IP, I guess. That they're gonna keep whatever IP they're allowed before AGI. So they've got all the code if they want to do anything. What then they've already moved on to Anthropic, which is good because I think like, Jatchy -Bee's probably gonna end up being almost as good for coding this in Thropic.

41:11So the whole thing, the shifting sands of AI gets a lot to process. Yeah, it is. And it's worth pointing out, it's some kind of interim M or U. It's not a final done deal. It's kind, I think it's at both sides saying we're making progress here where we're ending up. This is a moving on. This is, you know, consciously uncoupling here. Because if you look at it, the end game is some version of, because OpenAI had this weird structure for reasons we all understand. Microsoft ended up with this weird investment that in my view gave them a fair amount of blocking rights in a lot of different ways. It gave them access to the 40 -hour camera.

41:45It was 49 % of all the profits to a certain amount. It had, you know, revshare. It had a lot of things that was effectively a bit of a poison chalice for OpenAI in terms of making it a real, proper standalone company. And what's clearly happening now is it was a marriage of convenience for a while. Both parties are moving apart. The rational, I'm not sure if it is the, it would end up, but the rational end game for Microsoft is we got something along the way, but we don't just need a model anymore. And Sharpick looks to be more useful for this. We still have access to their model. We like that, but we can buy that on a third party basis, just give them money, be, be a customer of the model.

42:21We got some lift from AI in the short term. We have some business with them as a hosting provider for us. All those are good things. But in the end, my guess is they convert that $13 billion investment from a blocking kind of thing to a pick a number between 20 and 30, 35 % ownership stake in open AI. And you know, open AI is what half a billion dollars Microsoft will have put in 12 billion and probably be worth 120 or 50 billion. It's a 10x venture return on 12 billion. And once it's a great return, but as you guys know, we've talked about this. It doesn't move the needle when your market cap is 312.

42:55You don't get paid as a large market cap company for making oddly enough $100 billion because it's like you've got a three billion market cap It doesn't move the needle when you zoom out three or four years I think the conclusion will be while that was an interesting investment We got a kind of bit of a lift from Microsoft perspective. We made a lot of money But done move the needle we got some buzz on AI in the short term But we didn't really get what we wanted and we don't have what we need in terms of AI And we probably got to keep cranking on that three years time How do you think the relationship will look between OpenAI and Microsoft and then Amazon and Anthropic?

43:31The pairings that we've seen so far. I think it's clear that Microsoft will be a large shareholder. Hopefully, OpenAI for them will be bought a customer and a vendor because they will be selling cloud capacity to OpenAI, but not an exclusive basis. They will be buying from OpenAI access to the models, but probably not an exclusive basis because they'll be all moving on traffic. So in other words, a perfectly normal relationship between the larger software company and the planet and You know this entity that they help form found and start But it's now grown up. It's left the house, you know They're no longer dependent and it's just a perfectly fine arms land relationship With a massive equity ownership that's probably gonna make them 100 billion to 200 billion dollars Which is a lot for anyone else, but still the real value to Microsoft has been the lift and its perceived market cap a nice actual market cap from the perceived AI buzz.

44:26In this two years, we're frankly, they had nothing to put the heat back on the Microsoft team. The real question would be when open AI finally pulls away and you can rely on your complex agreement with them to get access to the AI. Want, have you built your own AI that matters? Have you done something? And if you have, that's great. And if not, then you missed that market. That's where that one will be. I don't have as good a sense on a traffic and Amazon. I'm not informed on it maybe, I'm not close to either, but my guess is much the same. Often when big companies partners with a small company, the small company gets smothered.

44:57In both these cases, the small company won. They got the money, they got the critical mass, they got the credibility, and now they've pulled away. And neither Antropic now open AI needs Microsoft or Amazon at this point. They don't need them for money because the industry will give them infinite money. They don't need them for compute because Larry will give them infinite compute and return for money. They don't even need a redistribution. So in fact, both these companies, ironically, just like Microsoft, 30 years ago, used IBM and then left them an empty husk. I would argue on Tropic and OpenAI have used their large corporate relationships, gotten the value out of them.

45:35It's still a bit sticky because the agreement's weird, but fundamentally they've made it. They're independent standalone companies. Thanks for your help, guys. Here's your equity position. Call me for the IPO. And Rory, thanks to your description of an empty husk with a scale AI, I had them in my inbox this week asking to come on the show and tell us why they're not an empty husk. So thank you for that. That'll be coming to a 20 VC soon, which should be an interesting one. Well, you know, we all did think that for a long time when that it was a weird deal. I mean, Microsoft buying 49 % in essence of OpenAi was the first of those deals, right?

46:07Those style deals, the scale, wind surf. But it didn't turn out that way. They didn't leave a husk. There were some superficial similarities, but in the end, we all thought, in fact, if we, probably the first time we did the show, we probably might have still said that Microsoft basically acquired OpenAI. It was an acquisition in disguise, as it turned out not to be the case, not remotely the case, right? Who does to Sam Altman for dancing his way out of the one of the greatest bear hugs of all time? He basically had to sell his company to Microsoft to get it off the ground, and now he's gonna get out of it.

46:38He's gonna get out of it like wow No, you're exactly right the truth is the other one the empty husk common when the founder goes with the acquirer It's a bear hug. It's an empty hug It's an empty husk when the founder stays independent like some stunning wind I think you're exactly right Jason that is a I mean it is Paul grain You've got to give him credit set it you could put him on an island with a bunch of cannibals and he'd be king Well, you put him on a plane to Seattle Think him back with a bunch of money and now he's king This is what I find funny. We go about as the Oracle and the OpenAI scat takes an online fucker.

47:11I'm not batting against him. You know, he might find someone. Exactly. He might find some of that money. Do I think the Oracle will book a fair amount of cloud compute from OpenAI? Absolutely. Maybe not to a hundred billion, but it's his willing to provide a little lower price than Microsoft. My guess is, those fine people in OpenAI will take it. You know another thing when we had, because we had Cassia, right, with his leaving 200 and something million behind. It's another thing when you have post economic people, it's difficult to fully predict the outcomes of these things, right? So not only did Sam not leave the husk, but his ability to have no equity in open AI, Microsoft couldn't pay him enough to move over to de -hustify because he had no equity to husk.

47:52I mean, Kaz may make a billion, I mean, Harry was kind. His job is to make a billion dollars from open door. But even risk and time adjusted, you know, leaving 200 million behind to Shopify another 70 something million in grants and what he might still get. You could only do that if you're post economic, right? I especially hate it when like some guy that was a senior marketer at some company and spun out with a cup of million bucks tells everyone he's post economic. But we just Sam and Kaz are taking post economic actions and it's very interesting in today's world where a couple billion isn't very much.

48:25In market cap, in valuation, not in personal income. A couple billion dollar seed round where barely it's barely gonna make Terry show. Oh, what's next, Tommy? We're gonna dive into kind of the application land. Two that Jason is passionate about, and I'm really excited for this ashy. One is Higgsfield and the other's Rap Lit. Jason, which ones do you wanna start with there? Either one, man. There is one thread. There's like this Higgsfield gamma thread. And I just think it's somewhat interesting that both are slightly under the radar. I mean, the CEO of Higgsfield was not quite complaining, but sort of shouting this week, right?

48:55When he did around that, hey, he's gotten in revenue and certainly in users gotten there, even faster than lovable in friends, right? Doing quick video, I mean, I'm a small investor. I've been a user since it launched. I mean, I love Higgsfield and gamut 60 million, if I like zero to 60 million this year, that's pretty good for slides. Just to be clear, Higgsfield is a AI video creation company that raised $50 million and also announced $50 million in ARR and with forth the time frame then lovable and replete. Yes, and it may be gamut close too, right? And we can talk about Higgsfield's under the radar if you're not a creator using the app.

49:31Gamma maybe folks on this pod have used it more often so under the radar. I guess we could talk about that. My meta point is, you know my God, right? If you don't see some of these numbers, it's not just cursor and friends and replet, which we could talk about. Going back to Kaz, homes are a big market. Restaurants are a big market. Shopify, but sometimes we don't even realize that short video and slides are massive. I'm just massive. And the Higgs fields can do this in the shadow of Google, even though they're using Google models, that they can do it in the shadow of so much competition, it's just, this is why it's so hard to do a triple, triple, double, double.

50:06It's not just loveable, there's so many loveables. No, and there might be 20 or 30 loveables. And I think what you're seeing, I mean, stepping back, what you're seeing here is that with AI, there's a series of things that, quote unquote, ordinary people couldn't do before, be it coding, or be it video creating. You couldn't do it. And these tools are making it accessible to everyone. So you have this step function, 10x, maybe 100x, increase in accessibility of creativity, are coding. And that's the positive momentum. And then the negative momentum on all these deals, the replettes, the Hixley list, oh my god, you don't control the underlying model.

50:42If you don't get enough space, you know, will you have choice? There's a lot of risks on those deals, but sometimes it pays to zoom out to the big picture. The big picture is anyone with internet access today can create video, cute videos, can edit videos, can be creative in a way that five years ago you couldn't do unless you were trained special effects editor. And that's huge. Maybe maybe seven months ago, it's your eight point. But you couldn't do these things. And now you can do it for pennies. You can do it for pennies. It's beyond disruptive, right? And you know, anytime you're dealing with shit that everyone can do, you have the potential for these exploding growth rates.

51:18And you guys are living it with Lepland and lovable and coding. and I think Hank is an example of that in creativity. And I think of it going more on them. Sometimes I would look at some of these things. Like I would be like, we use Gam all the time. I love it. But I'd be like, how the hell could that get to 60 million this year? It's like, do we really make enough slides? But to Rory's point, it's a way to create content you could not do before AI, so I get it. But it's just, so many of these markets are bigger in the age of AI than they were. I know it's Captain Obvious, but Higgsfield for short videos and Gamma for slides, even like Opus Clip was like the first little AI investment I did.

51:54Like I got it, but I didn't think it could add up to so much revenue to make these clips, right? You gotta get the spreadsheets right. You can't use the Tam spreadsheets from 2021. I find this time a little bit like COVID though in terms of market forecasting, which is a real difficulty in understanding what is a sustainable market trend that will be meaningful and enduring versus what is an experimental market that is cool to create, but ultimately whimsical and doesn't last a cycle. And I'm finding that uncertainty, very challenging as an investor to be quite honest. But the thing is, like, we agree, but that conversation we've been having since the beginning of AI and a lot of thin wrap or apps died for that reason, right?

52:34But what we are seeing, it's a valid concern for venture, but what we are seeing at least is the nominal NIRRs pretty high in these apps. So it may still crash and burn, don't get me wrong. But if you're using Higgs fielding gamma, and lovable and replete, and you're seeing triple digit NRR, even if it's not the NRR we used to talk about for B to B. It's hard to say no as a VC, isn't it? It's hard to say no when you see 140, 180 % revenue. You can say no and just sit at home and knit. I don't know when the margins are, where the margins are. You have to project out and go. But it makes field as profitable, as casual positive.

53:06It varies based on the application. It varies based on the... They're not all replete and lovable with negative margins. They're not. I guess my learning is it's not ob like they're all over the place what the margins are right they're all over the place I agreed and you write. I mean how again. Yeah, it's hard You've got to figure out which exploding growth company is going to be sustainable and which exploding good company is not But at least you're dealing with the problem of exploding good companies And you know, yeah, yeah, yeah, let's but you know, I'm an investment business air wallets very similar businesses This is my stripe.

53:38This is an unwaveringly enduring, growing, strong market. Fantastic. Comparatively, these others are incredibly experimental, potentially groundbreaking and potentially whimsical. Very different. We've got to be able to tolerate a loss ratio of nothing else. You've got to be able to tolerate 30 to 40 % of losing your money on it. They are very different. And I'm not naturally good at these creative deals. I get all your points. It's my, and I tend to be the steady compounders. But I think different deals have different attributes. And you've got to look at these and go, some of these you will be flashes in the pan.

54:13So the question is, what's the distinction characteristic of the companies that explode and then sustain? Right, and my gut, I'm kind of riffing here, and we can talk about it. It's probably two things. It's probably having expansive white space that you can grow into, which are costal with those, more things you can do versus getting caught off shortly. and then secondly having a founder who's maniacally focused on doubling down and adding all the rest of the stuff. And something you guys said about lovable and replant a while back stuck with me, which is you can envisage a whole bunch of uncillary products around that so as people build their websites, all the other things it takes to make that website work.

54:51And you can envisage building an economic model around the combined thing. So I think it's a combination of the opportunity. I think some of these things will be thrashes in the pan, not trying to be mean, but to use the hop, like hop in in covert, right? It will be a temporary phenomenon that goes away, but finding the ones where you have that explosive growth and then can parlay it into enduring is going to be pretty damn interesting. We've never seen competition like today. Never. You used to have six months, maybe 12 months. You launched something, your competitor would kind of look at it, decide if it was worth their time to build it, commit to trying it, then six months later get it, but you had a full year.

55:28Now you have like two weeks. Everyone complains about competition and everyone's prepared to do anything to solve the problem except the one thing that will solve the problem which is step away from the table yourself, Harry. So we've got too much competition but you're not quitting. I'm not quitting. I mean tough luck. It turns out, yeah, it's a very competitive time up and down the stack. It wouldn't be a lot easier if there was half the number of people. But the opportunities are compelling and people are going to show up and try and play. I could imagine I don't think this is gonna happen, but it's not impossible and Thropa could lose half their revenue in the next 12 months because GTP 5 Codex might be just as good.

56:04They could lose half of it. Like literally all you do is turn it on and cursor or lovable or replet or a million other apps. Whoever Higgs Field or Gamma moves over to GTP 5 Codex instead and if GTP 5 Codex is as good as Cloud Code, which it just launched, I could imagine it is 95 % than is good. You could imagine in today's crazy world and Thropic could lose 30 or 40 % of its cloud code revenue in one year. It's very imaginable. I'm not saying it's going to happen, but this switch, it could happen. That even that may not be stable. Going to Harry's point, forget about whether lovable and repil it and base 44 are stable.

56:38I'm not even sure cloud code stable. To state the obvious, that would be a very different level of stability than we saw on the sassy of where these things lasted forever, they churned 5%. If you are righteous and if it's even 30%, 40 % probable or something like that could happen, and I don't have a developed opinion yet on it, that's obviously a very different world you live in in terms of risk. Yeah, it could be high risk. The only interesting thing I'll take is that I interview honestly three to four dachicone CEOs every week and on this topic, two interesting elements, completely price and sensitive as to how much they spend on anthropic and cool code in particular.

57:17They're like, I would spend 10x, don't even look at the line item. Number one, snacking this duality of like super low switching costs and a complete awareness that actually they would very happily move to more of to someone else if it were a comparable service. Which goes to explain the urgency around CapEx for these companies because their belief and so far it's been correct. It's that if you're competing with cloud code, all you know is the only way to outperform is more reinforcement learning, more pre -training, more whatever, which means more cupex, hence the urge to decode its actual demand on cupex, because it's the only way to win.

57:55All the players are being rational in the game, but you can see it adding up to something pretty scary. Bringing this all together, the Higgs fields the rat place. The thing that could also kill them is actually the fact that Wix has base 44, which is actually doing incredibly well, the fact that Adobe or Canva could do what Higgsfield does with the existing distribution they have to it, going to the distribution and going to the incumbent versus start -up. How are we thinking about incumbent versus start -up and the core crux there? The market would say that the Wix acquisition has worked very well.

58:33Probably going to be 50 million there by the end of the year, so that's a win. The market would also say, you're just based on the thing that Adobe and, you know, let's be on a Salesforce. I've tried to announce AI products and I've gotten some traction, but aren't able to access that explosive growth. And I think the market reaction to Adobe stock price kind of reinforces that. So it's not that kind of simple binary answer. It's some pop folks have pulled it off and it's easier for a hundred million to make a difference at Wix. then it is to make a difference that Adobe are Salesforce, 23 billion in the case of Adobe, and 40 something in the case of Salesforce, where it's hard for those incumbents to move the needle significantly, which is why the stock prices have been down because you're not getting the AI explosion.

59:17For sure, but I think to me the base 44, which thing is interesting because we've been asking for a while, can the incumbents benefit from AI the same way the startups have, right? And we're looking at service now kind of faking it. and we're looking, we had Mark Benioff, who we all love, but we're not seeing it in the numbers yet. And we see Palantin, but Palantin is a completely different company that is AI first. So we're not seeing, and we're seeing in our own portfolios, we're seeing a lot of our 2021 high flyers, not exactly crushing it in the age of AI. There's the dial pads, the talk desks, there's the others that have, but a lot haven't.

59:49But what's interesting, then you see Wix come in and they buy a little lovable replica and that is just a cheap clone by one guy. I mean, Kudos to him, right? Solo founder, right? bought for 80 million using the same underlying technology cloud code, right? But they bolt on what Wix is good at, which is safety and identity, okay? And then they bolt on the friggin funnel. They push it out to their base. And if that's nothing to 50 million in a single digit number of months, imagine it's 200, 250 million. And more importantly, for the numbers, to Roy's point, if it's 10 % market share, that's a lot for a big company distribution to get in a couple months, 10 % market share.

1:00:27So if Adobe could do that, ifigma could do it, right? Ifigma can do it with its thing, could it be revenge of the incumbent? I don't see much evidence, but I like the base 44 as one example of the revenge of the incumbent, right? I don't want all of our friends to go down into relevance. I wanna see Zoom back, I wanna see everybody come back and be roaring in the AIA, right? Not just the new guys. I mean, speaking of incumbent and innovating as an incumbent, while we've been on this, I've been sent by a lot of people work day acquiring sauna lamps for 1 .1 billion dollars. Yes. Wow. They were at like 50 in error.

1:01:09There's a pretty great outcome for everyone involved. 1 .1 billion dollars to work day. I think sauna is great. Joel's great. But this was a second clean very much. Wow. Wow. But you know, in these times, being number two can be a great place for Ebene. Yeah, absolutely. When number one is unacquirable, you get so many offers. And I wish I'd realized that as a founder, right? I mean, knowing to Rory, even if EchoSign had just done okay and we'd gotten up to 100 million, just the folks that DocuSign turned down would have come and bought us for a billion bucks. Like I wouldn't have had to do anything just being number two.

1:01:46I would have just had to open the email and sold for a billion at a moment in time. Like today it wouldn't have worked. So today is a great in the age of AI you can't buy glean's unsellable, unacquirable, lovelables unacquirable, replettes unacquirable. So be a number two for venture and the other thing in frothy times they'll pay up too. They'll pay two times three times what they would have paid otherwise. So number two's great when number one's not available. Just don't raise too much if you're number two. Don't make yourself unacquirable. Can I push your thinking as number one really unacquirable?

1:02:14One scale gets bought for $14 .9 billion. Are we not seeing the limits pushed for what is acquiring? Yeah, but it's got to be a hyperscaler or someone. Workday can only pay so much, Harry. Workday cannot pay $26 million to buy Gleene. What's Workday's market cap today? It just doesn't have the capital to make all the VCs what they want. A great. For sure, the hyperscalers can pay up, but also a lot of folks won't sell it any price. And so being number two, just as founders, it's a cheap code. Just don't raise too much, be acquirable if you're number two, be kind. and you will be shocked in frothy times the offers you'll get.

1:02:50You'll be shocked the offers you get being number two. Have you ever regretted selling both of you? Yeah, a lot. You often do. A friend of mine said to me this week, Harry, I've never regretted selling and making millions of dollars. I never found her a VC though. That's different questions as a founder versus VC. He's a VC. As a founder, I would say more than 51 % of founders regret it. I regret it. but as a VC, here's the hubris in this. You're gonna tell a founder, she or he can't sell, and expect them to work twice as hard after you tell them to f off. At the end of the day, unless you're a total douche, if the founder wants to sell you sell, it's not your decision that's the height of hubris in my experience.

1:03:31A great, and I don't think you even do tell him. I mean, you ask me do I regret it? It's like, there are big guns when I look back and I go, oh, I think if we'd held, we would have compounded and been bigger, and you have objective facts that make you believe that, which still isn't the same as saying you regret selling. In fact, in that particular, one of the cases, I'll choose to say my words, because in case my dear friend who is relevant to his life, I talked to the CEO many three or four years later, and I said, oh look, our competitor is now worked, four acts of our work, do you regret it?

1:04:01And he wisely said, no, I took money off the table, I bought a house, I got married, I've got kids, I'm wildly happy, I'm doing another deal, Here you can want to invest, here's the terms. My life is great. As an objective matter of fact, you kind of go, compounding would have been good in that case, but it wasn't to be, and I don't regret it vehemently. I'm just like out of it. There's only a few where you look back and go, there was a lot more compounding in it. A lot of the time you go, yeah, that was a good call. And again, I think the more salient fact is this, Jason Wright is, it's the founder call.

1:04:31So my ammo is actually very different. My perspective is not having a gender one way to it. The first thing I always say to founders is, if the liquidity window opens as a private company, you should pause and take it seriously, because most of the time it's not open. So the mere fact that it's open, you have to pause and think, you have to change your game from your 90 % heads down work hard, and now someone's made an offer. It's now time to get real. And think, why don't you not have to apply that same mindset as an investor? You do, but I'm saying for the founder, it's more significant, because it's all or nothing, you can get it all after Tim.

1:05:03And then you have to realize how do you feel about things, as I all said, and now would be a good time to voice any of those concerns that you've been suppressing deep in your, you know, sternum here, guys. Are you having active partnership discussions about much more liquid secondary markets and a trade of mindset of maybe selling in a way that you wouldn't have done years before because secondaries are available? They are, but you know, truth is, I think they're available, but there's a small number of companies for whom are easily available at a discount and there's a much larger number of companies that, You know, when you have your winners and you look at it and you go, I don't know if the market fully appreciate what's this work yet I think I'm probably a holder here.

1:05:40So I have no reluctance to sell. It's a little like the founder window opening Everd likes to talk about this LPs like to ask about this, but the truth is the number of times that as an individual investor You're in a company that's so freaking amazing that there's a free liquid secondary market Where you're in early enough that you have a big enough head to move the difference. It's low if you have one of those per fund you're doing great. No, you probably have three or four winners per fund and only one of those is kind of that super marquee amazing one. The people who bought it in a 50 billion at strike are looking to sell at 90 billion just because it's liquid.

1:06:12Conversely, the people who bought it under a billion probably are unsure. So my point is this, yes, you have these conversations. It's not like you spend most of the day out there trying to keep your 10 million dollar AR company help and go and get it funded and hope it doubles. And that's a new world. Getting those is harder than ever when they're going from 10 to 20, but that's an entirely new discussion. Yeah, thinking of moments of liquidity. IPOs, we had a $3 .5 billion IPO for VR. We had Gemini go out at $4 .4 billion and 32 % bump on the first day. And then we had figure technology raising close to $800 million in their IPO.

1:06:50Gosh, how exciting and nice to have IPOs again. Which do you think is most interesting to discuss out of those? Well, can I add one thing and it will worry. Well, though, the busiest IPO weeks since 2021 isn't to be ignored or taken lightly. Now, it isn't the busiest year yet. It could end up, there's a, I mean, it's already September. Next year might be as big as 2021, but if you've ever been a founder, worked with a company that's discelerated, getting back to where you were is a big moment in time. Like you should celebrate when you got back. So last week, we were back to 2021 for a week. Maybe we'll get there for a month, right?

1:07:22And then you get there for a year. It's a big micro milestone to have a one week of 2021. They're all interesting for different things. I think figure is the most interesting just to start with that. So let's look at, and again, setting the scene. Looking at those three IPOs, two of them are vaguely crypto -related, Sega and Gemini. One of them is a different SaaS, primarily a SaaS company selling to governmental and transport, has a lot of complexity, and it's not just SaaS, that understates the complexity of the business, the via business. So of the two crypto companies, Gemini is the Winkelvoss twins, I mean, of social network repute.

1:07:58And the figure is Mike Kagney, who was the founder of SOFI. So the first thing you note here, these three IPOs, two of them are kind of second -time founders, depending on how you would adjudicate the Winkelvoss case. The F -Scott Fitzgerald line that there were no second acts in American lives is wrong. These are two out of three of second acts. Cogniz interesting because so far was an interesting company very differentiated has gone on to be traumatic only successful SPAC and you know a perfectly great successful public company and what figure is doing is using the blockchain as a settlement mechanism for home equity loans and other kind of non -conforming loans so at heart it's a financial services company it's a fintech play it's lending money which is one of the core things fintechs have done for two thousand years but it's interesting twist is it's using the blockchain to process the back office more efficiently.

1:08:47In the end, it'll rise and fall based on credit. If you make bad loans, you lose money in the lending business. But there is an interesting twist around using the blockchain to instantly settle these loans to be able to securitize them, the some kind of securities low issues, but interesting company, clever, good twist on blockchain. Fine, I mean, first of all, yay everyone. Finally, a use for the fricking blockchain that's standalone and independent of its kind of a trading asset. So that's what my Cagney's done here and all credit to him. It's a good company to stock, pop nicely. Everything about down to me is the most interesting.

1:09:23You know, Gemini, you're a pop tie and then drop down fast. It was fun. All three stocks behave very differently. So even at the trivial level of the detraiding, figure performed perfectly. Gemini popped way up and then interday came way back down. Revenue is declining and down. It's another crypto exchange. I never can tell them apart. It's just not coin base and not, you know, or whatever the finance is. So I don't know why it matters. We haven't used the climbing, but God bless those guys. They've hung out a long time. And then interestingly, from a stock price performance, via actually opens below its offer price and then bounced up during the course of the day, proving that it's not always free money to buy at the after stock price.

1:10:00But yeah, so fun week for stocks, but definitely to me figure the most like, oh, that's interesting. I'd like to learn more. The interesting question in the age of AI with via transportation, right? So found it 2012. So that's 13 years classic B2B plus that's not just that's but B2B plus 493 million invested 4 .2 billion dollar valuation will fluctuate so 12 years so that the investors in the aggregate 10x the total capital invested that was a A plus but not S tier investment until 18 months ago is a good enough today 13 years 500 in 4 .0 something billion out that was great until recently I would take it in a heartbeat He's not sure.

1:10:42He's not sure if he likes the fact that it has a defensible platform, big enterprise customers, or does he want to put more into lovable? He's just not sure which one he wants to do. They both have pros and cons. He's doing both, actually. I think at the end of the day, I'm thrilled to see IPO markets open. I'm thrilled to see exuberance. I'm aware that it will take 12 months for people to truly get cash back, But I am a incredibly selfish self -centred individual who wants LPs to have more money to put back in To venture and that will align perfectly with my fundraising cycles and so in Shala bring home some IPOs previous generation and fill up the LPs funding Did you know?

1:11:24Yeah, it was a good week. I was very excited for one though, which was bending spoons Buying Vimeo bend. I mean sorry you Americans you'd love to always claim the dominance over Europe and Texas energy. The European, the Italian, buying the public and emerging company for $1 .38 billion. First of all, stepping back, bending spoons is a quirky name, but a wildly successful buy -out shop that specializes in these old assets that have some kind of brand recognition but no obvious model. The most obvious one being ever -note, which they bought and have if you know, streamlined race prices on and I believe got into more profitable business models.

1:12:08So yeah, I mean, it appears to me, it's probably a successful formula. The engine thing for me is that they tend to buy us it's very cheap, centralized, just e -count the profits. Vimeo, I don't know how cheap it is at 1 .4 billion dollars. Like, extremely hard, they bought pretty cheap. Ever note, they bought pretty cheap. And to e -count that was much easier. At a 1 .4 billion dollar entry, You're moving to a different scale of entry price that you're moving into. That's a different game of roll up. I just have a emotional attachment to the brand as a creator I've been using Vimeo since the beginning, since when I've competed with YouTube.

1:12:44So that's a small portion of the business. But it's $420 million business that's basically flat. It's an annuity. And they're buying it for, then what, three times revenue? Yeah. Less, 2 .5 times revenue. So either they have to make it more profitable or they have to apply some folks that care more in software to inject a modest amount of growth in a time where Higgsfield and Gamma will do a third of their revenue in 12 months. Inject a little that Higgsfield and Gamma love, although I don't know that they've made and people use Evernote more that the spoons brothers. Right, team, are we ready for a quick fire?

1:13:22A kowshi quick fire? Fire away. This will be great, Roy, you're gonna love this, okay? We had the main man cast on the show. Open door today is sitting at about, I'm just gonna check for the accuracy. $9 .30 a share today. Where is it gonna be? And a year. December 31st. It's 9 .30 today. Where's it gonna be? Good God. I'm pausing. Oh, good God. Because cans seem like a very nice man. I got 24. You got 24. That's my bet. My bet's 24. He just asked AI Rory. Do you not know this? No, no, no. I just, actually, I just did the way I do ventrinvestments. I just do a line. This is the beauty to be a late seed investor.

1:14:02Like early seed, you got a squint, late seed. I just, since first investment, just draw line, it's pretty much accurate. The CAS is pretty damn good. The memeers like him as near as I can tell from Twitter. I'm going 24. I don't know what the bed is exactly, but I got 24. Roy? I mean, somewhere between nine and 24, I think it keeps going up. I think it's an extraordinarily hard. And I think this guy is so smart and keeps talented. it, they'll make noise, move momentum, and I think in the near end, the stock will appreciate. Because you can make the story feel big. I'm just going to say, I think it's a brutally hard business.

1:14:36And over the next three to five years, you want to believe in that vision of being able to help people in the most important financial decision of their lives. I just think it's an extraordinarily hard business because there's a huge amount of arcane, detail on every house and everything's a special snowflake. So I hope I'm on because he seems like a great guy. I just think it's a hard thing to build massive enterprise value in. Adobe is getting crushed by the markets, but the revenue is strong, continuing to increase. Will share price be lower or higher in 12 months for Adobe? Adobe's been going, it's going to 10 -12%.

1:15:13The multiple went way up a year, year and a half ago. I think they convinced Avenue AI'd be good for them or whatever. Some amazing post -COVID story. They obviously were really high in 21. I want to say I should have 40 or 5 or P .E. The high price sales multiple did post -COVID in 22 and then it came back strong and all that's happened now is it's reverted back to what it should be. In 5 or 6 times revenue it's a widely profitable slow growth. They've done some things in AI enough to not feel stupid but not enough to actually move the needle significantly. So it's kind of value just right. It hasn't crushed, it hasn't fallen, it's just the euphoria has faded away.

1:15:55And now it's, I want to say, five or six times sales, 15 times forward PE company. I think it's still vulnerable to medium -term disruption from AI, but I don't have a, oh my god, it's crashing from here. It's just reverted to what it's probably worked. Roy, higher or lower? Larger to my answer to the question has to be no more than 10 % higher because if it grows 10 % in sales, it should be 10 % higher if it's fairly valued today. But I feel it's a little confidence comment. My point is the salient one is you're an hour to have, and I've seen that on Twitter, oh my god, Adobe is crashing. The real narrative is Adobe's return to work.

1:16:33Jason hates that. I don't think you believe that the stock price doesn't assume a certain amount of forward growth in its current stock price. I don't believe you believe that. Yeah. I mean, I think it's been growing. You don't like the Cal shape, fair enough. You don't like, I'm betting down. I'm betting mid down at least 10%. Two reasons. One, Scott Belzky leaving bad sign for AI to Dobie. The guy is not 70, okay? He's still got the fire. He goes out to be more creative. Give him a couple hundred million like cast. Getting Scott to leave was a big blow. And this may be behind the scenes, I'm exaggerating his influence, but I've worked with a lot of the folks that are still executives today.

1:17:12It's a big loss for Adobe losing him in the AI. And maybe he came up short of what he wanted to accomplish, right? It's a big company, a lot of ships to move, but you're just at a loss without him. Two, this is my biggest tell of being worried about public companies today. Okay. This is my least favorite metric, even worse than Google's margin. I mean, Oracle's margins on its cloud services. AI influenced ARR. Adobe announces five billion of AI influenced ARR. You don't have to say this if you have AI, AI, AI, influence, AI, that to me, any public company quoting billions of AI, influenced, AI, does not believe they will have billions of real AI.

1:17:52Just I just think it's a both are a bad side to margin, but this is a business that can't be killed, right? It is an enduring business. Listen to Jason, you could be right there could be a little more deflate in it. It's not going away, but it's 10 % growth, it's slowing down. In retrospect, the real comment is how the hell that people think Less than two years ago, then it was worth 18 tons of evidence when it's worth six times today, right? I mean, what was people smoking? Yeah, a lot of Adobe's history is financial engineering and the move to the cloud and they got a lot of run out of that Right, you know, in the end Scott wanted to buy Figma didn't happen any left They did at least try they weren't left they tried they tried But yes, just think if they bought it you'd be getting those little pop -ups from Figma too telling you you know You've used up your license for Figma Adobe cloud Please pay $79 .99 for the next 12 months.

1:18:39I find the Adobe product to be the most annoying and least understandable set of license products out there. Right, which is Jason's not that worried. It's Jason's. Well, it is because what happens is you sit in a, if you want to know what happens, you sit in a conference room with spreadsheets, right? At 11 % growth, like sales horse is probably getting the majority of its growth from price increases today. Like it's hard to parse the numbers, but my rough view of sales horse With six to seven percent annual price increases on average growing nine, you can't trace it perfectly. Maybe we really can, but I'm assuming the majority of sales forces growth is from price increases.

1:19:14And you're sending a Dobie to Levin and you can figure out how to get people to accidentally prepay for three years or confuse monthly annual. That could give you hundreds of millions of dollars of revenue, right? And they don't care about the cash. They care about the gap recognizable revenue. So they want to lock you in for life at the highest price and those meetings do happen and they last days They last days on those things. It is not just why product manager going to muck. I actually think this is an interesting discussion for the last minute here because you're right Just like it's 23 billion dollars in revenue as roughly right and you have you compare the wicks thing right if you don't think AI Fundamentally threatens your business here.

1:19:52You're delusional because you it's what we discussed earlier you're going from a small number of professional creators to an infinitely large number of amateur creators. You've already allowed Canva and Figma to get onto your skin, and now you have a whole next generation coming up. What do you do that's aggressive enough to move the needle here? Because for Wix, I don't know, doing a billion and two billion revenue is a hundred million dollar. Revenue acquisition is somewhat meaningful. What do you do if you're Adobe and what do you buy in AI? Now, do you camp by Figma in Pre -AI? And how do you think about the threat here?

1:20:26I mean, they've announced some projects But it just doesn't appear to have landed. I mean one of the areas we've been looking at a lot is that area of next generation Creative tools and you know for a while there was like maybe Adobe will land some punches and be relevant They were talking the right game, but they don't appear to have done so yeah But Jeff lost and made the great point which is obvious But I think Adobe is in this trap you can't cannibalize your seats. Yeah, Adobe wants to add firefly in AI to your expensive suite and Microsoft's half giving up on getting people to buy AI co -pilot for office, but what we really want is not even to buy those seats.

1:21:00I don't have to buy a seat with Higgsfield or with Reeve or with Gamma. I don't have to buy a seat at all, right? Or it's just one seat, right? Going to Casas Point with Shopphile, I need one seat to run my whole freaking store, right? And so we love the seat, man, but it's tough in the age of AI, because you don't want to cannibalize your seat, Jeff's right. It's tough one for Adobe, right? Guys, this has been fantastic. The joy for me is that you can see the progression of every show actually, I think. This has been amazing. Thank you so much as always. Rock and roll. Now, I want those shows to be the best shows that you listen to every week.

1:21:33So I want your feedback. Let me know what we can do to make them better. Any guests that you'd really like us to have on, I want to hear your thoughts. Harry at 20VC .com. But before we leave you today, let's talk about agents. Specifically, Piper, the AI -SDR agent brought to you by Qualified, the agentic marketing era has arrived, and if you're a B2B marketing leader looking to scale a pipeline generation, Piper, the AI -SDR agent, wow it is here to help. Piper is the number one AI -SDR agent on the market, according to G2. And hundreds of companies, like Box, Asana and Brax, have hired Piper to autonomously grow inbound pipeline.

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From the publisher

AGENDA:

00:00 Opendoor's Potential and Market Valuation

03:32 Why Did Kaz Leave $300M on the Table to Join Opendoor

04:44 Why Does Kaz Believe OPEN Can Be a Good Business When the Market Doesn’t

06:34 How does Kaz Feel About OPEN Becoming a Meme Stock?

17:25 Kaz’s $0 Salary but $1BN Stock Based Compensation

23:41 Oracle and OpenAI Partnership: WTF is Going On?

42:21 Microsoft's Investment in OpenAI: A Financial Perspective & Who Has the Power

44:46 Why Sam Altman is the Greatest Politician of our Time

48:33 How Anthropic’s Revenue Could Go to Zero Overnight?

50:12 Replit Raises $250M at $3BN Valuation and Higgsfield Raises $50M at $50M ARR

01:06:33 IPO Insights: Figure, Gemini, and Via All Go Public

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01:13:20 Quick Fire Round: Adobe Up or Down by EOY? What Price Will OPEN Be EOY?

 

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