Alfred Lin on Airbnb, DoorDash, OpenAI & Citadel Securities

Alfred Lin https://x.com/Alfred_Lin, Partner at Sequoia Capital and three-time #1 Midas List investor, has backed some of the most transformative companies of the past two decades. His portfolio spans early bets on Airbnb, DoorDash, Uber, Zipline, Kalshi, and Commure to growth-stage partnerships with OpenAI and Citadel Securities, consistently identifying founders and businesses that redefine entire markets. He continues this track record today with next-generation category creators like Profound, which is building AI-powered brand visibility, Nominal, which is powering mission-critical engineering with a unified data stack, and Clay, which evolved into a go-to-market engine by relentlessly adapting to innovation. In this conversation, Alfred shares his philosophy on founder-market fit, resilience, and backing visionaries who create new categories. He reflects on Airbnb’s near-collapse during COVID, DoorDash’s rise, and Sequoia’s landmark investment in Citadel Securities, while breaking down how he evaluates IPOs, valuations in the AI era, and why the next decade will be defined by reimagined consumer experiences. Alfred Lin: https://x.com/Alfred_Lin Molly O’Shea: ⁠https://x.com/MollySOShea⁠ Sourcery: ⁠https://x.com/sourceryvc 𝐒𝐏𝐎𝐍𝐒𝐎𝐑𝐒 ​Brex https://brex.com/sourcery—The modern finance platform, combining the world’s smartest corporate card with integrated expense management, banking, bill pay, & travel. https://brex.com/sourcery ​Turing https://turing.com/sourcery—Turing delivers top-tier talent, data, and tools to help AI labs improve model performance—and enables enterprises to turn those models into powerful, production-ready systems. https://turing.com/sourcery ​Carta https://carta.com/sourcery—Carta connects founders, investors, and limited partners through software purpose-built for private capital. Trusted by 65,000+ companies in 160+ countries, Carta’s platform of software & services lays the groundwork so you can build, invest, and scale with confidence. https://carta.com/sourcery ​Kalshi https://kalshi.com/sourcery—The largest prediction market and the only legal platform in the US where people can trade directly on the outcomes of future events: https://kalshi.com/sourcery Follow Sourcery for the latest updates! https://www.sourcery.vc/ 𝐓𝐈𝐌𝐄𝐒𝐓𝐀𝐌𝐏𝐒 (00:00) Alfred Lin, Sequoia (01:31) Why technology cycles move at 3-month speeds (03:55) Why markets often consolidate to 2–3 leaders (05:07) “Build for the world, not San Francisco” (07:14) Airbnb’s COVID crisis and Brian Chesky’s leadership (13:15) Culture under stress: resilience in tough times (15:45) The essence of founder-market fit (16:20) Motion ≠ progress: why velocity matters (17:55) Resetting company culture in the AI era (19:55) Clay’s pivot into a go-to-market engine (21:10) Profound and the rise of AI-powered brand visibility (25:15) Breaking through to invest in Citadel Securities (29:45) IPOs, exits, and what makes a public company (33:05) Performance metrics: numbers behind the numbers (33:58) AI premiums, valuations, and when they turn reckless (39:45) OpenAI’s $500B valuation and trillion-dollar potential

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Airbnb entered 2020 as the number one IPO candidate. It was this big fanfare and we're going to go public early in the year. From January, February, March, and then April, we saw the growth rate just steadily decline as COVID started spreading throughout the world. And at some point, it went negative. That's pretty scary. We don't love the word speed at Sequoia. We love the word velocity. Velocity is a vector. It has a direction and you want people aligned to that direction.

• 0:30Molly O'Shea?

  How did you partner with Citadel Securities?

• 0:33Speaker 00

  Well, it's funny because I would have never imagined that Ken Griffin would sell a portion of Citadel Securities. Our partner Konstantin met Ken at a conference and developed a relationship. And over time, I think it's over like two and a half years where he kept asking Ken, could we ever invest in Citadel Securities? And I think Ken said no many, many times and Konstantin did not stop. And so it was a team effort. Konstantin obviously sourced a developed relationship with Ken. Doug helped, I helped. We eventually broke through and got Ken comfortable with how Sequoia was going to help with the company building side. We may not know anything about market making, but we do know how to build technology businesses.

• 1:15Speaker 00

  And that's the type of help that Ken wanted around the table for Citadel Securities.

• 1:31Molly O'Shea?

  I was fortunate enough to listen to you speak at Forerunner's AI, Consumer AI Conference. I think it was a couple of months back. And there were two things that really stuck out to me. One that I mentioned on a podcast with Brian Kim from Andreessen Horowitz. But one thing you mentioned about these cycles, which I thought was just, it was like encapsulated so well is you said, things that happened three months ago are not relevant today. Things that are happening today are not going to be relevant in three months. Do you think? That's going to continue? Do you think it's going to compress more? How did you get to that framework of thinking?

• 2:08Speaker 00

  In the beginning of any technology cycle, it does feel frenetic. There's just so much changing. People are experimenting. People are trying new things. And I think the things that I observed was the things, the interesting papers, the interesting research in AI that we're talking about today, we didn't talk about three months ago, which by definition, we're not going to talk about whatever we're talking about today, what we may not be talking about three months from now. It's very hard for founders in that timeframe because what you want to do as a founder is to have a vision of, of, of a company that matters 10 years from now, right? If you're going to start a company today

• 2:51Speaker 00

  and it takes a decade to build a interesting company, you want something stable over time. And the thing that's stable right now may be that AI is going to transform the world, but how it does is very, very tricky. And so I think the great thing about that is startups are a lot more nimble than large companies. And they're going to be able to sort of experiment and do different things that large companies are not able to do. And so we're seeing more innovation. We're seeing more younger founders get into the game because experience is not as important as just innovation.

• 3:33Speaker 00

  And I stand by that. And for a period of time, there's going to be a lot of innovation. There's going to be a lot of companies that unfortunately won't make it. But we're going to, out of all of this, there are going to be some substantial companies that are created because AI is going to be, is probably the largest and most powerful technology megatron in my lifetime.

• 3:55Molly O'Shea?

  Why do you think markets collapse typically to two to three leaders?

• 4:01Speaker 00

  It doesn't always have to collapse that way. The restaurant business doesn't collapse to two or three leaders.

• 4:08Speaker 00

  I think in technology, there is an element, there is an element of network effects. There is a brand network effect and a lot of businesses

• 4:19Speaker 00

  want to be able to trade off between one or two alternatives. So you don't want to make one be the company. You know, and for, for the cloud, there's AWS, there's GCP, there's Azure. Because if I am Goldman Sachs, I want to be able to trade off and be able to use all of them.

• 4:42Speaker 00

  And if you're DoorDash or Uber Eats, you know, some level consolidation is good because otherwise you're just constantly fighting with a bunch of players. And so there's a, there's a natural for, there's a natural network effect in those businesses where it consolidates to number one, number two, and maybe a number three.

• 5:05Molly O'Shea?

  The other thing that I really liked, what you said on stage was build for the world. There's eight billion people here. You should think bigger. Specifically, you started, and I don't want to put words in your mouth, so you should say this yourself. But you were, you started off with like that specific area in San Francisco where we were and like the broader area, and then you expanded more and more and more.

• 5:29Molly O'Shea?

  Why do you think it's important to think like that when you're starting a company?

• 5:32Speaker 00

  Well, over the years, I've found

• 5:37Speaker 00

  that there's an element and a desire to be cultish. And part of being cultish is to help create a religion around something. And in the very early days, when I was working with, with different tools, there, there's a company called email reader called Pine. And literally the name of Pine is Pine is Not Elm, which was a previous email reader. And then you had the Mac and the PC wars. You know, there's a religion around the Mac and the PC. You have a bit of a religion around the clouds. You have bitter religion around Android versus iPhone. And yet. What you really want to do is not be web two or web three.

• 6:19Speaker 00

  You just want to build for the web if you're, if you're an entrepreneur. And so, yeah, you know, we were sitting in the Presidio. So I said, don't build for San Francisco, which has probably 800,000 people. You may start there. You might want to, your ICP might be 800,000 people and it may be everybody in the Bay, in San Francisco, because you're going to launch in San Francisco. But you have to think broader. All of the Bay Area is about 8 million people, but you want to move beyond that. And you can want to be able to reach the world. And that's how many companies start. DoorDash started with University Avenue, who was much smaller.

• 6:58Speaker 00

  It was around the Stanford campus and then all of Palo Alto, then a few cities, then nationwide. And now they're, they're trying to go internationally. They, they have a strong presence in Europe and they're going to want to build for the whole world.

• 7:15Molly O'Shea?

  With Airbnb specifically, they went through a really dramatic period during COVID. How did you help them navigate that if you did? What did you learn from the way that Brian navigated that? And what do you think of Founder Mode?

• 7:35Speaker 00

  I think one of the things that was fascinating about the Airbnb story and Bryant has credit on his leadership is he really, really knows how to navigate through a crisis. And I think people forget some of the facts, but he, Airbnb entered 2020 as the number one IPO candidate of 2020. And it was this big fanfare and we were going to go public early in the year. And from January, February, March, and then April, we saw the growth rate just steadily

• 8:18Speaker 00

  decline as COVID started spreading throughout the world. And at some point, it went negative. That's pretty scary. A company that is used to growing 30, 40% a year went to losing 80% of its revenue. And

• 8:38Speaker 00

  I think it was very reasonable for a lot of us who are focused on a variety of things to just go inward. But Brian was thinking about his team. He wanted to make sure that Airbnb survive this pandemic, but also for generations. And that was, you know, in some sense, resilience is about having purpose. And he had purpose. He wanted, he's always wanted to build Airbnb into so that everybody can belong and belong anywhere. That purpose, he was not going to give up. But that's in your head. And then you sort of think about it from the heart.

• 9:22Speaker 00

  This is like true suffering, like you lost 80% of your revenue. You can either choose to hope, or you can be in despair. And for him, he was, he's optimistic. He was a hopeful person. He chose hope. What are the bright, shiny things that were still working, even though things were were in decline? It was, it was experiences, because we could do virtual experiences. It was actually short, sort of shorter distance days. Airbnb had been a cross-border company where you traveled internationally, went to different parts of the world. And now we saw

• 10:04Speaker 00

  people leaving New York City to go upstate New York, leaving San Francisco to go to Napa. And that business still was working and thriving. So he focused on the places that were still really positive in this business. And he stayed really calm. And he stayed really calm to, we call these things crucible moments. You have to be calm and untangle all of the noise to find the direction that you need to go and to accelerate out of this situation.

• 10:45Speaker 00

  And then finally, so you have the the purpose in your head, the the hope in your heart. And then I just think that physically, he just kept doing the work. Every day he got up, he had an all hands, he had a team meeting. Every Sunday, we had, we had a board meeting. He prepped everybody from the board all the way down to all of his employees on what we were going to do. And that was a significant change. And along the way, he would call me and we would bounce off ideas. Obviously, we needed to raise money. Do we do it in equity? Do we do it in debt? Equity would be very punitive at that time. We decided to do it

• 11:29Speaker 00

  in debt. And we decided that we were going to cut expenses. But there's a, there's a framework, which is you cut them, you cut marketing, because we didn't need to market anymore. We cut offices, we cut contractors. And then the last thing he wanted to do was to have a layoff. But he had to do that eventually. And so it was a very, very logical, almost very thought through way of dealing with the crisis, even though the crisis is happening so fast.

• 12:00Speaker 02

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• 13:02Molly O'Shea?

  I find it interesting because I feel like his, his decisions as a founder at the time and as a leader.

• 13:11Molly O'Shea?

  On the external presence made it like, I don't know how to put this like, it made it that company and his leadership like super attractive to go work there. But in a, in a situation like that, that would crumble your culture. You would be doing layoffs, people would not be feeling very secure. It would be very disorienting, but having strong leadership does attract strong talent. I'm curious, how do you think about talent shifts and culture and resetting those cultures through these turbulent times?

• 13:47Speaker 00

  Leadership is about making hard decisions, in my opinion. And in difficult times, true leadership shows. Culture is also about hard decisions and hard times. You, if you think you have a great culture during good times, you don't really know whether you, that culture survives during bad times. A great culture survives bad times. And the test of leadership and test of culture is going through bad times. Which is why, you know, in some sense, the companies that's, that do extremely well have it hard early.

• 14:26Speaker 00

  And they can take lessons and they can shape their culture early to survive and to be just be resilient during hard times. I mean, Airbnb, they, Brian talks, talks about the fact that it was very, very hard for them to raise any money. In the early days. And then we, we like gloss over that because they had this nice little glide path for a period of time. But yeah, they started, it was tough. Nobody thought that we should fund a company where strangers are staying with other strangers. But he had a vision. I often talk about the fact that someone else's feature is another person's bug.

• 15:07Speaker 00

  Brian just thought that, you know, my father who loves staying in hotels, in the same hotel, in the same room. Because he wanted no variance when he travels for business. Brian thought that that was kind of mind numbing. And he wanted to create a company where people traveled much more authentically. And he brought that to life.

• 15:33Speaker 00

  And the pandemic showed that the culture he created and the leadership that he has can survive both good and bad times.

• 15:43Molly O'Shea?

  What do you think that means for being a founder in a highly competitive or a highly,

• 15:51Molly O'Shea?

  it could go both ways because they're both, you know, like extreme environments, either highly competitive or highly turbulent. What do you think that means to be a founder? Like, what kind of, what do you need to, how do you need to show up?

• 16:04Speaker 00

  I think you show up with a vision and a north star and you, you measure your uh, speed in, in the right direction. So we don't love the word speed at Sequoia. We love the word velocity. Velocity is a vector. It has a direction and the magnitude. And you want to go in the direction that you want to go in and you want people aligned to that direction. Um, motion does not equal progress. And you've heard that before from a variety of different people. And getting a company to align in a, and march in the same direction is what is really important during turbulent times. Because it's very

• 16:49Speaker 00

  easy to run around with as if your head was cut off during a crisis. It's very easy to see every little shiny penny that pops up because there's so much change in AI and try to go after a thousand different things. But your leadership as a founder is to make sure the company is focused in the right direction.

• 17:14Molly O'Shea?

  There's some interesting card data around this cycle in AI. And there is a premium that AI native companies are getting. And it's more dramatic in the series A and series B. But given the macro on the AI environment, how do you set a culture for AI or to rebuild for AI? I guess like, let me just, let me reposition all of that.

• 17:43Molly O'Shea?

  Talking about cultures and in this new AI era, there are teams that have to reset and rebuild. How do you help orient? Or what would you? What would you say is like the best practice or principles to use to rebuild those cultures for AI? There's founders like Brian Armstrong that are making really hard, you know, pivots or I guess like statements in his company. Everybody needs to learn how to use AI this week. If they're not, they're fired. And then there are others that are maybe taking it a little bit less intensely. But how do you think about setting cultures in the AI era and rebuilding them?

• 18:24Speaker 00

  I think you want to build a culture where people pursue growth and learning, period. And so right now it might be AI. And you want to learn all the tools that sort of can help you build things faster, automate things, et cetera. But when, when the internet happened, you wanted every single person in the company to learn about the internet. When mobile happened, you wanted everybody to learn about mobile. When cloud happened, we wanted to have developers learn about how to launch things in the cloud. And so I think you want your culture to, to stand for innovation, stand for progress and stand for growth.

• 19:05Speaker 00

  And the companies that survive over time have had to have act one and act two and do things that are hard. I mean, how does, how does Amazon, which is an e-commerce company, be a cloud company and build AWS? How does Zappos, who was just focused on shoes, go from all these other categories? How does Airbnb go from home sharing to all accommodations to experiences? Whether it was AI or not, you needed a culture that was going to be innovative and continue to sort of push the envelope of what can be done.

• 19:49Speaker 00

  And, you know, and so DoorDash had to do that from restaurant delivery to grocery to convenience to international. Maybe sort of take a step back on your specific question. I think for Clay, I'll just use Clay as an example, where they started out as trying to bring

• 20:10Speaker 00

  programming to the masses. They built something and there were no, there are not enough users who thought that this was something that they wanted. They didn't know what to do with it. And so Kareem decided to use his own product for go to market. And then they developed this whole notion of go to market engineer. That was the first sort of thing that sort of made Clay into what it is today. But then, okay, well, we're in the world of AI. How do we automatically update these leads using AI? How do we use more AI tools to help users learn the product so that they can prompt Clay to do the things that they want?

• 20:54Speaker 00

  That gets built into the culture because they've constantly been an innovative and learning company. And that's what you want to build.

• 21:03Molly O'Shea?

  I want to go back to the beginning when we were talking about all the categories you go after. Specifically, within AI, a company that I've gone to know a little bit more recently is Profound. And this whole new world, it's a category creator. From what, you know, another thing that I've heard from all your founders is you really back category creators. Cal she's absolutely a category creator. Nominal, I think they're going to be there. Airbnb for sure. Profound is, it's just like, it's totally new. Like, who thought you would need SEO for LLMs? And all of these sorts of things. But I'm curious from your standpoint, could you,

• 21:47Molly O'Shea?

  one, break down Profound, but then two, how you think about, like, I just, I just, I want to understand, like, who is Alfred as an investor? Because you back so many different kinds of companies. Like, how do you find them? And like, what makes you attracted to them?

• 22:03Speaker 00

  Well, Profound's a great company. Let's start there. And they're going to create this category of helping brands.

• 22:14Speaker 00

  Build their brand on AI. And if we start searching more and more on AI and trying to get more information, brands have to show up in foundation models and in AI the way that they want to show up. And so it is creating a whole new category, but I don't think they're going to stop there. They're going to think about what marketing is going to be and how it's going to be different in the world of AI, not just showing up on AI SEO. That's the initial wedge, but James has a much, much broader vision for recreating marketing the way we know it. One of the things that over all of these sort of mega trends that I've been fortunate

• 22:58Speaker 00

  to live through is that the business models changed. The internet, there was a lot of innovation around advertising. Ad units changed. Keywords became something that we bid on. It's just new innovation. With SaaS, obviously, there was this change in selling seats and selling it in a subscription model versus licenses. Mobile, we had in-app purchases. We had freemium models where you got the free version of the product and if you liked it, you upgrade. These things are like, are really interesting because I may not be able to build the product, but I can help founders reimagine what business models are going to be.

• 23:42Speaker 00

  And I think AI with the technology that's coming, we're going to reimagine a lot of business models. And so that's really fun. And so when you ask, you know, who am I as an investor? I don't love the word investor. Back to we love being partners to the founders that we back and the management team that they hire. I'm really a partner to solve, to help solve these problems. And maybe another way of thinking about me as an investor, these, all these different categories, I just see specialness in the founders and their desire to go change the world. This is a very fun business.

• 24:25Speaker 00

  Because I get to meet with the founders, these wonderful founders who want to go change the world, even if I don't agree with them, I just love hearing the stories and their insights.

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• 25:13Molly O'Shea?

  How did you partner with Citadel Securities?

• 25:17Speaker 00

  Well, it's funny because my brother is head of fixed income and macro at Citadel, the hedge fund. And I would have never imagined that Ken Griffin would sell a portion of Citadel Securities, this market-making business. I've asked him about the business and, you know, and he's just like, yeah, you know, it's interesting.

• 25:43Speaker 00

  But our partner, our partner Konstantin, met Ken at a conference and went up to Ken and talked to him and struck him, developed a relationship. And over time, I think it's over like two and a half years, where he kept asking Ken, could we ever invest in Citadel Securities? And I think Ken said no many, many times, and Konstantin did not stop.

• 26:14Speaker 00

  And so it was a team effort. Konstantin obviously sourced a developer relationship with Ken. Doug helped, I helped. And so we eventually broke through and got Ken comfortable with how Sequoia was going to help with the company-building side. We don't, we may not know anything about market-making, but we do know how to build technology businesses. And that's the type of help that Ken wanted around the table for Citadel Securities. Because fundamentally, it is a technology company. And in some ways, it is an AI company. They've been using math to...

• 26:52Speaker 00

  Find ways to make money with and and calculate arbitrages and calculate risk for those arbitrages for a long, long period of time. And so they know how to do that. We know how to help them build technology, build and grow a technology company.

• 27:11Molly O'Shea?

  So why did you want to invest?

• 27:15Speaker 00

  Um, maybe in another life, I was supposed to work at Citadel Securities. As you know, I go all the way back to, I was, I was born in Taiwan. I grew up mostly in New York City. I came to this, to the US not knowing any words of English. And my parents were like, yeah, you're, you're, you're kind of bad at languages. I was always bad at languages. So you better study math and do it well. So I studied math. I went to Harvard and studied applied math. They took a class from Robert Merton. And the class is called Continuous Time Finance.

• 27:58Speaker 00

  A few years later, he would win the Nobel Prize for his work on continuous time finance. And I, I asked him for a job at this place called Long Term Capital. And he said, you know, you're pretty smart and you're pretty good at math. You should probably go get a PhD and then come and ask me for a job. I said, okay. And so I came out to Stanford to get a PhD in statistics. And I fell in love with the internet. So I dropped out.

• 28:31Speaker 00

  A few years later, when I was at Link Exchange, I was the CFO, acting CFO at the time, we're trying to take Link Exchange public. The market was dropping 100 points an hour. Sorry, August 31, 1998, it was dropping 100 points an hour. And

• 28:49Speaker 00

  that's because long-term capital was blowing up. So I dodged a bullet by not going to long-term capital. But, you know, there was some ricochet because we couldn't take Link Exchange public. We eventually sold it to Microsoft.

• 29:02Speaker 00

  But you know, I could have ended up working for a hedge fund or for Citadel Securities or Citadel or some company like that. You know, growing up, I think most, most of my family members, definitely my mom and my dad would have thought my brother would have worked in entrepreneurship because he's, you know, sort of the extrovert, he's charming, and I was the introvert, awkward. So I was gonna work, either be a professor or work in a hedge fund. But the two of us swapped places in some ways.

• 29:39Molly O'Shea?

  Wow. And then that led you to having a piece of it?

• 29:44Speaker 00

  Life, life is funny that way.

• 29:46Molly O'Shea?

  Sentimental. I like that. IPOs are causing a lot of demand. Demand from people like Citadel, public market investors, those types of personas to want more of these tech companies to go public. It's good for the ecosystem, but there is like a little bit of a pressure there. There's a little bit of pressure from investors for DPI. I'll share some information in the comments on some card data for that that's coming out today. But how would you advise companies as they think about these exit scenarios? And I was like, well, why wouldn't

• 30:27Molly O'Shea?

  you want to get acquired? So like, putting that to the side, how do you, how do you help your companies think about exit scenarios? Whether it's through M and A, going to IPO, what makes a company a public market company? Or, you know, other routes of exits?

• 30:47Speaker 00

  The exits is not something that I spend a lot of time thinking about, or the founders I work with in general.

• 30:56Speaker 00

  I think the, the reason that is, is if you, if you focus on building a great business and a great company, then exit opportunities will abound. There, there's always, if you need to raise money, there's always, whether it's in good or bad market, if you have a great company, you will be able to raise money. And that's true privately, and that's true in the IPO market. That's true after the IPO where you might raise, you may raise financing in the public markets through a secondary or through, through a debt. And so I've always asked founders to focus on building a great company first and foremost.

• 31:38Speaker 00

  On exits, it is the timing of an IPO, the timing of whether you sell the company has a lot to do with what the founder wants to do. I always tell founders, an IPO is another fundraising round. It just happens that you're selling it to the public and you can get some liquidity for your, for your early shareholders and your employees. But it is a fundraising round. And are you prepared to be a public company? Are you prepared to give quarterly earnings and guidance and all those things? It's about preparedness on the IPO. On an exit,

• 32:20Speaker 00

  one of the things to think it through is this is a terminal price, but more importantly, whether, when you sell the company to the acquirer, whether it fulfills your vision. And in some cases, it does. You can partner with a larger platform to help fulfill your vision. And that's the best scenario. You don't want to just be, you don't want to just merge with another company and then have the, the product get shut down. You want it to thrive inside of the acquiring company.

• 32:55Molly O'Shea?

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• 33:03Molly O'Shea?

  Brex is all about spending smarter, moving faster, the intelligent finance platform. They love performance. And so I'm curious from you, how do you measure performance? What are the metrics that you use to determine?

• 33:17Molly O'Shea?

  This is when I want to enter an investment with a company and this is when I want to follow on in investing.

• 33:23Speaker 00

  I think, I think the performance metrics for each company is very bespoke to them. Obviously, we look at things such as,

• 33:33Speaker 00

  for example, unit economics, how well the customers were retaining. Those are the numbers behind the numbers and we focus much more on those numbers than on pure, sure revenue growth and profitability.

• 33:49Molly O'Shea?

  Going to Carda Data,

• 33:52Molly O'Shea?

  they had a question to the market and to all the companies that are on the platform. Do AI companies command a premium? AI software companies that raised in the first half of 2025 saw a 30.9% higher valuation. So this is about a $55 million valuation versus $42 million.

• 34:12Speaker 00

  It is a hot market for AI. And the one thing that I'm somewhat concerned about is many of these companies that we call AI companies. They're software companies, they're security companies, they're customer service companies. In probably two or three years, we will not call them AI companies, just the same way that internet companies over time, yeah, there were native internet companies, but over time, every company became an internet company. Every company became a mobile company. And so we try to think about whether the premium is deserved

• 34:47Speaker 00

  or not. And

• 34:50Speaker 00

  these premiums that are being paid, probably some of it is

• 34:56Speaker 00

  because we believe that the market and the market sizes are expanding. And if you told people back all the way in the internet that online advertising was going to be as big as it is today, they would laugh at you. And so right now, I think there's a lot higher premiums, 20%, 30%. It's because we believe that the market sizes are going to be much, much larger. And we've given some of this data. Our partner, Pat Grady and Sonya Huang, when they hosted AI Ascent, they showed this map of when SaaS was created, we had a certain size of the software market and we thought SaaS

• 35:41Speaker 00

  was going to be a big portion of the size of the software market. It turns out that SaaS is even bigger than all of the software market in the past. We grew the software market. What AI has the potential of doing is looking, is it's looking at the services market, which is measures in tens of trillions of dollars. And that's why the premiums that we're offering seems very high and seems at times ridiculous.

• 36:14Speaker 03

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• 36:59Speaker 03

  At what point are they reckless?

• 37:02Speaker 00

  When you can't grow into that valuation over time, eventually what has to happen is the a company is the discounted free cash flow. That's what it's built for. The security that you own is the net present value of all future discounted cash flows. And so you have to be able to justify the valuation that you're entering at and the multiples that you're paying for is very pay forward. So I think we're paying probably two or three or four years ahead of where most of these companies are. And

• 37:41Speaker 00

  It is a little reckless. The other way to look at that, that's probably from the growth standpoint in the early stage business.

• 37:51Speaker 00

  The justification for higher and higher valuations is if a company is going to be worth a billion or ten ten million dollars, whether I invested ten million pre-money, twenty million, thirty million, a hundred million, it really doesn't matter so long as I pick right.

• 38:11Speaker 00

  But if you double the valuation, that means you have half the number of shots that you can deploy, you just have to be twice as good. And so my push for the industry is if you're gonna write a check that is twice as large for the, then you need to have twice that conviction. So that's the quantitative way that I sort of think about these things. And then the other, uh, the other reason I think people feel good about the prices that they're paying is in the short run, they, they seem to be right, meaning they get marked up pretty quickly.

• 38:55Speaker 00

  But we all know that we won't know whether these companies make or not for another decade. And I, I don't want to sound down. I'm very, very optimistic. And this is the only sort of line of business that I know where you meet two founders, a few founders, and then, and they have an idea. And within a decade, they can build a company that's worth one billion to ten billion dollars. We have many examples of that. In two decades, they can become ten billion to a hundred billion, DoorDash and Airbnb being close to a hundred billion. In three decades, they could be a hundred billion to a trillion, Apple, Google, Nvidia. And maybe in four decades, those companies will be worth

• 39:41Speaker 00

  ten trillion dollars, not just one trillion.

• 39:43Molly O'Shea?

  The company missed out on that is OpenAI. And how they got to a five hundred billion dollar secondary valuation. How do you think about that one?

• 39:54Speaker 00

  Well, so it's easy to dismiss the 500 billion and say that you can't make money from 500 billion. But if we let Nvidia, which is worth 4 trillion today, compound at 10% for another decade, it's going to be worth more than 10 trillion. So if OpenAI could be worth 5 trillion, then it would be a good investment from here. So the, as we talked about, this is such a fun and dynamic industry. And it's so fun to see these companies grow up. But the, the market size is just getting larger.

• 40:28Speaker 00

  The opportunity set is getting larger.

• 40:30Molly O'Shea?

  It's really exciting.

• 40:31Speaker 00

  It's really exciting.

• 40:32Molly O'Shea?

  It's fun.

• 40:33Speaker 00

  And you get to talk to all these founders, too.

• 40:35Molly O'Shea?

  I get to document it.

• 40:36Speaker 00

  You get to document their, their successes and you can document their failures if they want to teach others on, on what they've learned from some of their failures.

• 40:46Molly O'Shea?

  It's really fun. Yeah, that was one of the reasons why I wanted to, I mean, why I wanted to go so hard with sorcery, at least now. It's like, when are we going to get this historic of memorable stories and moments? It's crazy, even the year previously, even with the coup, like, that was wild. I wish I could have documented that one.

• 41:05Speaker 00

  We're going to look back very fondly, um, because we always do very fondly on history. And thank you for documenting everything because we get to see it in those sort of raw elements of, of the building stages.

• 41:20Molly O'Shea?

  Well, as we think about looking forward, I want to know two things. One, what is your favorite Kalshi predictions market?

• 41:30Speaker 00

  I can't pick among all the markets. I mean, it's a little unfair. I love economic indicators, kind of a nerd that way. So I, you know, lots of people would think that's one, one of the sports markets, but no, I'm less of a sports fan, more of an economics fan.

• 41:51Molly O'Shea?

  Yeah. I also like the alien one. It's always fun to ask people what their opinions are on aliens. Do you think we're going to learn if aliens exist this year?

• 42:00Speaker 00

  This year?

• 42:01Molly O'Shea?

  Yeah.

• 42:02Speaker 00

  Well, some people already believe that there, we have proof that aliens exist. So I don't know how you resolve, how you would resolve that.

• 42:11Speaker 00

  You need an oracle to determine. I think that question depends on what's the oracle you use.

• 42:18Molly O'Shea?

  One of my favorite things is going to the Kalshi, one, ideas and seeing what people actually say on their trades, because you actually put your money where your mouth is and you see the trades in the ideas section. But then also nerd for me, I did a couple of episodes on quantum and so I requested a quantum market. And in the quantum market, reading the fine print is just, it is extraordinary.

• 42:42Speaker 00

  The fine print is what determines whether something is yay or nay.

• 42:49Molly O'Shea?

  It's, it's a true, I guess, it's like a true testament to consumer behavior and like what you got. Most people are headline readers.

• 42:59Speaker 00

  Well, I think we've conditioned ourselves to being that. We used to read text, long form, and now we read

• 43:08Speaker 00

  expos and they're short.

• 43:10Molly O'Shea?

  Well, to close out, what are you most looking forward to in the next 12 months?

• 43:15Speaker 00

  There's so many things that I look forward to. I think the, I think there's going to be a bit more stability into what we're building in AI. And I think that's going to give a lot of opportunity for founders. And I most look forward to moving on from just pure automation and AI to reimagining consumer experiences. And I think a lot of things can be reimagined with AI that we have not done for a long period of time. We reimagined consumer experiences with the internet. We reimagined that with mobile. And I think there's going to be lots of innovation on consumer experiences in AI.

• 43:58Molly O'Shea?

  Really exciting. Well, Alfred, it was a pleasure to have you on.

• 44:02Speaker 00

  Thank you for having me. This is so fun.

• 44:04Speaker 02

  Hey, it's Molly. If you enjoy our interviews, check out our newsletter sorcery dot B C, where we deliver a once a week top deals and tech headlines email and also go deeper on our podcast interviews. Subscribe to Sorcery today and don't forget to subscribe to the podcast on YouTube, Spotify, Apple, or wherever you listen. Link in description to sign up.