#884: How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan of DoubleClick, MongoDB, Business Insider, and Many More

Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss Show, where it is my job to deconstruct world-class performers across all disciplines. My guest today comes from the world of business, Kevin Ryan. He is one of the leading entrepreneurs and investors in New York, which is an understatement, often called the godfather of New York City tech. He is the founder and CEO of Alicorp, a New York-based venture capital firm that incubates and invests across, catch this, healthcare, AI and software, consumer tech, deep tech, and more. But investing is just part of it. He is also a co-founder of several notable companies, including MongoDB, Business Insider, Zola, Guild Group, and Transcend Therapeutics. What do those all have in common? They are completely different industries. Earlier in his career, Kevin was the CEO of DoubleClick, which he helped grow from a 20-person startup to a publicly traded company with more than 1,500 employees. We get into a lot here, so without further ado, please enjoy a very wide range of videos. Kevin, thank you for making the time. So nice to see you. Happy to be here. So I wanted to just give people a scan at 30,000 feet of the landscape, meaning your chronology for a second. So this was prepared by the robots. So don't believe everything you read, but let's just go through some of the basics. I'm not going to spend too much time, but please indulge me for a second. So 1985, graduates from Yale. I think that was economics. Begins his career at Prudential Investment Corp. All right, New York and London. 90, 1990. Earns his MBA at INSEAD. Subsequently works at Euro Disney in France, then United Media. We're going to come back to all of that. 1995, helps launch the blank website. I'm leaving that blank for a reason. We'll come back to it. And then after that, DoubleClick, that's where if people interview you, and I know you don't do very much media, but in the few that I've seen, that's where a lot of people start. We will not start there. Goes on DoubleClick, sells for 1.1 billion. Ryan steps down. 2007, founds AlleyCorp. We're going to spend a lot of time on AlleyCorp. Co-founds Guilt Group, Business Insider, 10 Gen. Later renamed to MongoDB. Then co-found Zola, a wedding registry company. And Nomad Health in 2015, a marketplace connecting clinicians with temporary healthcare jobs. I'm trying to give people an idea of the breadth of fields. 2015, Axel Springer acquires control of Business Insider. I've got some numbers here, but who knows? 442 million, something like that. Hudson Bay buys Guilt Group for an announced $250 million deal. MongoDB in 2017 goes public on NASDAQ 10 years after its founding. I know that's a lot of money. I don't know if it's going to be a big deal, but there's a lot of stories behind that. 2021, we met, I guess, or had dinner next to each other two years prior to this, roughly. Co-found Transcend Therapeutics, developing new medicines for psychiatric conditions. We will certainly talk about that. 2023, skis 101 kilometers to the South Pole. So that stands out as an outlier. Then June, 2026, Otsuka completes its acquisition of Transcend, 700 million upfront, plus up to 525 million contingent on future sales. July, 2026, announces Alicorps, 335 million, second fund focused on backing companies at their earliest stages. I think you're doing a lot more kind of deep tech investing also. This is a crazy bio, Kevin. There are so many reasons I wanted to chat and learn from you. And I wanted to start, we're eventually going to get to things like recruiting and talent scouting, but I wanted to talk about trends and gazing into the crystal ball, looking into the future. So I've read that you sometimes do an exercise of listing trends on a whiteboard. Throw 20 trends up. And I'm going to read a bit. This is from foundersjourney.org. So one exercise I do is to list 20 ideas on the board of trends that I believe are going to exist for 10 years. And then what are the implications that come out of that? And you can look at societal trends, healthy eating, automation and restaurants, gig economy. And this is where I think I missed steps. So first, I get the first part. You ask, if I bet that's going to continue for 20 years, the market's going to grow by 5x. He asked, what will exist that doesn't exist today? So sometimes I miss that second step. But could you perhaps just walk me through how you think of trends and spotting opportunities in those trends? And it strikes me that I think that 10 years is important as opposed to like one or two years. But could you speak to that? Yeah. First of all, 10 years is important because to build an important company, unfortunately, you can't do it in two or three years. It does take 10 years. And so you've got to bet on a long-term trend. So if it's something that is hypey today and is going to be done in two years or started five years ago, you're too late. And it's very hard. I've gotten it wrong many times. But sometimes you get it right. So double kick was internet advertising was going to be very important. And that trend, we absolutely got right. Unstructured data in databases was Mongo. And that was a 20-year trend. Psychedelics was a very important trend. I became a big believer that that, you know, would be significant for mental health and that we are five years into that 10-year trend. Nuclear energy is something that we made a bet on, a very significant bet on two and a half years ago and are an incredible company there. The creator economy is something that we made a bet on several years ago and have an extremely successful company there. That's a trend that is continuing. There are other trends out there. And more specifically, value-based care is a trend. Value-based care is a way the government has structured it so that you can go to multiple hospitals or doctors' practice. And that's a trend that we're seeing. And work out ways for them to reduce their costs by focusing on a specialty often. And if you reduce their costs, then you can share in the savings. And so we have multiple companies there. And sometimes there are trends I'm not able to think of the right way to benefit from or the right product. Longevity and this focus still haven't come up with the right thing. I have a conference called DOC, which is in Napa Valley in October, that is Longevity and Science. And I'm going to talk about Longevity and Science. And so that's to learn more. But I don't have a product idea yet on that. Why do you do events? Are the events opportunity and talent scouting mostly? I understand that learning is sort of a bedrock beneath both of those two. But what was the impetus behind an event like that? Yeah, so I have four now. And some of them are linked to my business. So Deep Tech New York, 450 people talking about the most fundamental deep tech trends that are happening out there. And I'm going to talk about that. And I'm going to talk about material science, things like that. Then I have one Digital Health New York, which is next week, then DOC. And then I have one that's called Odyssey, which is just ideas. That's less commercial and just getting 100 very smart people together. And I look at that as more intellectual nourishment. I don't think of it as directly generating business. If I meet fascinating people in different areas, good things will happen. Some of them may be business oriented and some of them may not be. Could be dragging 100 pounds. Yeah. No, for example, I'm leading 20 people as part of Odyssey to China in a month. And the theme is, what does China do better? There are things they do worse, but there are things they do better. And I haven't been in a long time. I don't do a lot of business in China. So I just felt like I need to see that. And so I'm bringing heads of VC firms, a bunch of interesting people on that trip. And we did one, took 16 people skiing that are off-piste skiers to a place in Val d'Isere. And I'm bringing a bunch of interesting people on that trip. And we did one, took 16 people fascinating conversations in the afternoons. I'm going to take 30 people to Switzerland on a hiking trip next May. Anytime I'm surrounding myself with great people and we structure it in a good way that these conversations are happening, then I'm going to get a lot out of it. All right. So I had planned, but plans change when the conversation gets flowing on hitting early chapters and I want to hit early chapters. But before we get there, I remember sitting next to you in Portugal, whenever it was, it was 2019. And the first thing I thought was, good God, what does this guy do for exercise? I mean, you take, seem to take, unless you're genetics or just like Usain Bolt or something, fitness, movement, exercise very seriously. And we'll probably get into what that regimen looks like a bit later. But when you organize these trips, so I organize a few trips a year for friends. How long are the trips? In the case of say the hiking, off-piste, like you got to check some boxes before someone's going to be like avalanched. And so on. In the case of the hiking trip, how do you think of composing the group? How long is the trip? What goes into creating that? So the hiking trip is three or four days. It'll be probably 30 people. And my structure will be probably a four hour hike, sort of eight till 12, which is a good size hike. You can go longer, but four, maybe five. And then the afternoon we'll have sessions. So there'll be someone talking about climate change. There'll be someone who's talking about, about nuclear or whatever is happening that we think is interesting or consciousness. And so you should feel like you had great content. You got to know other people, you had great conversations. And then at dinner, a lot of that comes together and you get to hopefully come away knowing 20 of these people who've been selected because they come from different walks of life, but are doing something very interesting. So with 30, does that mean that you would have something like 10 who ended up getting up to speak? Yeah. And at dinner, structured in any way and the reason I ask is that there can be unstructured events. One of the characteristics of dialogue that I really enjoyed in the early days. When it got bigger, it changed. Also didn't realize I was in Peter Thiel's secret society when it came out in the media. Who knew? In any case, in the early days, I remember they had very small tables, four to five people, and there would be a question at each table and someone would have to take the responsibility for effectively acting as moderator. And there was frequently assigned seating to ensure that you would get exposed to a variety of folks. And I thought that was really an astonishing way to squeeze a lot out of a few days. But in this case, if it's unstructured, how do you think about seating and grouping people? Because if it's just one long red wedding Game of Thrones thing, then if somebody's at one end and someone's at the opposite end, they're not going to interact necessarily. Is it Jeffersonian? At 30, it's too big to have one conversation. So what I would generally do, actually, is in the first two nights, have seating so that it forces people to mix it up. And maybe on the last night, not do it. So then you can say, you know, the person I really want to catch up with is this. And you should have that opportunity of someone you spent some time with. On my bike, I have an annual biking trip where we just classic four days, do a lot of mountains last year in the Douro Valley in Portugal, might be in Italy, things like that. There's only eight of us, and each person has a topic that they, one meal is going to be a 20-minute, 30-minute conversation that you're going to lead. And it can range from very early on, we were talking about crypto, and it wasn't so obvious. Good topic. When you were relatively well off, how do you handle money with your children? Always a tricky issue, and all of us had kids. So wide range of topics. On the trend side, personally, I remember, for instance, way back in 2008, 2009, I met Toby, who is still CEO of Shopify. And they had 10 employees, something like that. And I was like, I'm going to do this. I'm going to do this. Got very lucky, ended up becoming the first advisor to Shopify. But in part, the reason I committed to that is I thought, okay, one year, two years, who knows? But in 10 years, will there be more people online? Will there be more e-commerce? I feel like that is a no-brainer. Toby and his team, Harley and everyone were also very focused on being basically first movers on mobile. And I was like, okay, well, will there be more mobile phones, more broadband? I mean, that seems obvious, of course. Yeah. And so, ostensibly, someone will probably win a decent part of that market. Sure, why not? Give it a shot, right? And there's a lot of luck involved with these chance encounters. But I feel like you, over time, have probably developed a more sophisticated lens or kind of multi-dimensional lens of looking at trends. So if you're, say, hosting a company offsite, and they're imagining where different industries are 10 years from now, can you walk through that and say, well, this is where I'm going to do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Can I do this? Maybe common pitfalls or mistakes that people make when extrapolating trends or forecasting. Are there any follow-up questions or frameworks that you use to hone in on something that might be an opportunity, or disqualify something that is shiny but is actually a suicide mission? One of them, again, if this were formulaic, we'd all be doing it, and it would be easy. So there's definitely some gut feel and some instincts and guesswork in here. But I'm always thinking about, let's imagine Shopify does very well. Who else works with them and supplies them? That's a second order. And so let's think about that. The people who are providing the fix and troubles to data centers are doing very well. And how does behavior change? What does that mean? Sometimes that has a. result that people will stop doing this and be doing more of this. Can you give an example of that? Well, I'll give you one example in second order that we sat down in 2003, didn't quite do it, and thought about bandwidth price is going down, and they were going down. The reason there was no video in 2003 is because it costs about $10 per thousand to serve content, and you could get about a dollar in advertising. So that model doesn't work. But we looked at the trend and thought, you know, by 2005, 2006, they're going to cross. And we should have started YouTube, and we didn't. And it's not a coincidence that YouTube started in 2005 and then crushed it. And that was the second order that led to a company that today is worth $300 billion. That was a good acquisition. Incredible. Incredible acquisition. Many of you know that I've battled sleep for decades. I've had onset insomnia. I'm constantly hot because I'm a little meat cube. And the list goes on. But I've used Eight Sleep for many years now since the beginning. And man, it is a godsend. 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What did guilt do? It's a good news and bad news story. So this was an unusual one where I spent a lot of time in France. I have a French passport and everyone in France in 2006 knew Vente Privé, which was basically guilt of France. And they were doing a billion dollars in revenue, doing this concept of flash sales, where during the day at one moment, they would have discount merchandise of high-end brands on sale. So the equivalent, if you had time to go to a sample sale, which you don't, and I remember walking by a sample sale in New York, and there were 200, mostly women, in line. And I remember thinking, you know, the person who lives in Boston, you don't have sample sales. It's really the New York brands. And there's a lot of people who'd like to be in that line. And these guys had figured that out. So I started it. It became a phenomenon. So in our second year, we did $175 million in revenue, which is crazy. And, you know, it's merchandise. You have to buy it and package it and sell it and return it and things like this. And we did an incredible job of providing that. So in year four, we were doing $500 million in revenue. This is quite a while ago. And then the problem was, which does happen, is the market changed on us. This is the part I want to ask about. Okay. Yeah. And so what happened was when we started it, let's use Marc Jacobs. Marc Jacobs did not have a website in 2008, 2009, because they sold to Bloomingdale's and people like that. They were a wholesaler. Why would they have a website? They got a website. They started discounting their own things. You had been filling that gap. I had been filling that gap completely. And at the time, Macy's had a terrible website. They at least got it to mediocre by 2011, so did other department stores. Then Farfetch was there. So all of a sudden, I'm competing with a lot of people for that merchandise. It got a little commoditized and we couldn't figure out a way around that. So this leads to, Michael, question because you have to take shots on goal and sometimes the competitive landscape or the evolution of the competitive landscape is difficult to glean but did that experience with guilt inform how you think of durable capitalization on trends in other words like how you capitalize on that window but avoid getting crowded out when you have 10 other people do effectively the same thing yeah and it gets back to do you have a moat and we were trying to get to be big enough that we would have that moat and we got to be quite big but not big enough i mean i was talking to theory once and they had 20 000 items at the end of the season to sell i could buy a thousand good but doesn't move the needle for them and so i just didn't quite get there to have an impact on the market so it's hard to know exactly how big you're going to get how fast how much success you're going to have over your vendors and so we almost got there but didn't and one of the lessons there you know i went to the board and said i think we should sell the company and everyone's like well we were worth a billion dollars we thought we could sell it for 400 it's disappointing i said we have a falling knife here and so we went out and we only got 250 million dollars sax came in and paid for it and three years later they said i'll sell back to you for five million so better late than never exactly it wasn't a great sale but it was a lot better than it would have been because i just didn't like where things were going and the conclusion has been that i haven't touched really e-commerce since then you know it's solved startups have to solve a problem even if you don't realize that problem is there when you see it you're like oh yeah that is a problem i had and right now i can't i mean i can get anything delivered to my house in like 27 seconds i can return it it's inexpensive so i don't know how to do better i don't have any ideas whereas in many other fields you know cure for cancer nuclear energy psychedelics there are things to be built that have not been built that will improve the world a lot let's wind back the clock as i promised listeners earlier so we're going to get to the helps launch the blank website before that we have yale economics prudential investment corp yeah investment banking investment banking in sead euro disney was there anything that you learned or developed in those chapters that that then helped you when you moved to united media like is there anything sort of crucial or critical the key thing is i was quite financially oriented and very comfortable i've always been very comfortable with numbers and understanding fundamental trends and the business and that is a component of business and life and so all of that was business and then i wanted finance and then going into operations at disney so we had to manage hotels and it was a exciting project we launched euro disney you know fifteen thousand hotels and we had to manage hotels and it was a hotel room fifty thousand people every day huge project launches one day so i learned a lot about that but i decided i didn't want to work for large companies anymore so i thought there's a lot of training wasn't incredibly enjoyable i then wanted to go back to new york i got a job to be the cfo of 180 person division of united media for me that was a big job i was managing 50 people i managed all the operations and the finance and it was a turnaround made a lot more money for me it was a huge step up and i was down for the job i was down for the job i was down for the job i was down for the cfo and coo what is the blank that i'm leaving i still remember i read an article in business week that talked about a thing i did not know which was called the internet you may have heard of it and i remember reading that thinking oh my god that is incredibly cool like we could all be in touch with each other we can send each other messages we could buy things and remember there's no browser at the time so by 95 i launched because we owned a lot of intellectual property and one of which became extremely successful and the reason was there were a lot of tech people who could use the internet without a browser and so we had enormous traffic i started selling advertising which was a hard-coded ad just up there ibm was the first person they took it for two weeks i made up a price on the spot i mean how do you price something that's literally never existed and we did our own merchandising so we started selling t-shirts and ties and things like that and so a year later we had a very successful business i went to the parent company and i said this internet thing is going to be big and we have a head start so why don't you give me i was thinking as a loyal corporate citizen give me a couple million dollars and i'll build up an internet division we can do it for other companies and the disturbing thing is the guy i was talking to was very nice smart traditional media guy and he said no because we're going to wait for the next internet what does that even mean i don't know first of all i know you don't know what you're talking about there is no next door and the disturbing part is i remember thinking you're just really too old for this and he was exactly the age i am today 61 or 62 and a very successful executive and other things just wasn't in touch with what was happening right at that moment so i then concluded this is not my future but i believe in my thesis i thought this might be and it turned out to be true was that a gut feeling or were you tracking numbers outside of traffic what made you know i could see at that time if you're around in 96 it was just early but starting to boom companies were starting more and more people were online no one was getting offline they were starting to buy things they're starting to use maps you could just see it worked i mean the things we take for granted now that you can buy something from anywhere see content from anywhere that never existed and now i saw that i'm like this is a no-brainer everyone in the world is going to be doing this so i think it was like your point on is e-commerce going to grow yes it is it's just better it was a sort of it was a no-brainer and so i said i'm going to go out and start an internet company i met maybe it was a very tiny world at that point people in silicon valley wanted to bring me on to join existing companies like i don't remember excite a bunch of companies like this drove by them on the one-on-one yeah and at that point i had a year of internet experience which made me one of the most experienced people at the time so people were super excited to have me join and do something and then i ran across two guys who had started double click six months before and who were very smart very technical and i still have great relations with both of them and so they said why don't you come join us and i wanted to stay in new york i thought that was going to be a successful company and so i joined i was the 10th or 12th person i started for a couple months as cfo became the president and then became the ceo what do you think contributed to that ascension to ceo what skill set or otherwise contributed to that i felt like a founder technically i'm not but i felt like i was and so i was like i'm going to do this i'm going to do this i'm going to do this and so i just was a team player and wanted to make this company successful and i adapted extremely quickly to making decisions very very quickly you have to make your decisions faster than other people because if i wait so for example we opened offices in 25 countries in those first three years and our competitors were only in six and when i went to microsoft or pratt & gamble we do business in a lot of countries we need to work with you and then once you had all them smaller players were like well pratt & gamble and microsoft and we're working with you so we'll work with you so we just ended up almost dominating our space and i think i did adapt to that of fast decision making understanding the numbers willing to take risks we were in 20 countries before our first country was profitable like if it never worked you'd be like what were you doing and we made some mistakes along the way but in general we built the world leader double click today as an independent company would be worth 100 billion so i want to talk about that not exactly building the parachute on the way down but the ali corp model let's just say especially in the first few years because i hesitate to put it under the label of incubators because it's different in a lot of ways unlike say a y combinator it's not a bunch of people coming in with their own ideas that you select then you take a tiny percentage for a tiny amount of money and teach them how to pitch a demo day it's not what you do and i guess my understanding is i guess in the early days you and your partner are putting in maybe 500k each into each company acting as co-founders yeah building each for about six months as a proof of concept and then going out to raise venture is that a fair description maybe a year a year okay but we really built the product generally launched the product and then went out to raise money and so we were really focused on those companies and we did three and then we did another batch of threes we did total of six three of them were hugely hugely successful gilt business insider and mongo after the formation of ali corp when were those founded all between 2005 and 2008 and the last three were started in the same year at that time were you doing eight companies a year or did that end up later much later because there was really only two of us and my at the time my partner he's retired now but dwight merriman is one of the most brilliant technical minds that we've seen so he's really the brain behind the double-click technology and the mongo technology along with one other person and so you know we had this great partnership where everything technical he really handled i didn't even worry about it and then everything on the business side finding the ceo you're building it raising money things like that i focused on that it seems like you have a number of incredible strengths and i'm sure there are more but there's the trend opportunity identification There is recruitment of talent, capital formation, nation, being able to raise money. In some cases, a lot of money, depending. And as you mentioned with DoubleClick, getting to 25 countries before the first is profitable. Because when a larger company wants to partner with you, they're going to want that global footprint. And you raise the capital necessary to reach that critical mass, escape velocity, choose your metaphor. And I'm wondering how you think about that in the, say, first three to five years of Alicorp when you were founding companies. And some of them took longer, obviously. MongoDB, I think, stands out as an example of that. But let's just say with Business Insider, for instance, I listened to an interview you did with Sampar and Sean Prairie. And you mentioned how in the beginning, you had a handful of people covering everything. We could talk about the problem and the gap that that addressed. But just for the time being, I think this is where. It's worth spending a moment on. So in the beginning, you had a handful of journalists handling everything. They were only handling Silicon New York technology. Okay. They're handling New York technology. It's important to start narrow. So they handled New York technology. And then at a certain point, though, I imagine, right, they were spread thin. But then once you got the traffic, that allowed you to hire more. And so you could stair-step it in a way that I think a lot of people would be hesitant to. But ultimately, that allowed you to dominate space. Yeah. And I'm not delivering that in a very eloquent way. So maybe you could explain it. I'm just wondering how that type of thinking manifests in other companies that you start. And Guilt and Business Insider, even though they're very different businesses, we did the same way, which is that Guilt started with one sale a week of women's clothing. And then we went to two and then three and then five. And then maybe a year later, added men's and then kids and then travel and then home. And in Business Insider, we start because you. It's better to do one thing really well than a bad job on everything. And so we started with only three people. So we discovered New York Tech, which wasn't that big. But we did a good job. And then expanded and had a Wall Street vertical. And then added another vertical. And then as we added more people, they would add a vertical, eventually defense, retail, things like that. And then got to 600 journalists at one point and did a great job. But roughly when we sold our afters, we had six people covering defense. That's great. When you and Dwight were putting in the initial million dollars split 50-50. Presumably you're taking, I don't know, 30 plus percent of the company, something like that. Day one more and then it gets diluted down. Right. Exactly. Right. You're planning for that dilution with the later raise. In the early, let's just call it the 2005 to 2008 period, how did you get very, very smart, capable people to quit their jobs and come run these companies? And they have to. They have to believe that, one, the idea is a great idea. They have to believe that we are adding value and that there's something here and that we should do it together. And those are the only two things they have to believe. And then we can help them. And so we had just sold the company in New York City that was the most valuable startup company ever created at that time. So we had credibility. They thought, you know what, we're going to get you in to raise money and help you do that. And we did. And we were able to do that. So that was the pitch. But we've, you know, Henry Blige is a perfect example. He was, you know, he's a business insider. He's an incredibly talented person. At the time, had a mixed reputation because what had happened on Wall Street years before, but a great writer. And just for clarity, you basically said he was uncomfortable with something that was standard practice, right? That was his sin. Yeah. No, I stand by what he said and did, actually. But he came on board and I knew him a little bit, but brought him in. And after 30 minutes, he's like, this is a great idea. We should do it. What did the pitch look like? So simple. Now you won't believe it. There was no business news site that was online, that was inherently online. And at the time, Wall Street Journal and Businessweek did not update their sites during the day. Yeah. And so. Got to wait for the paper. And so all the things we did, and we're not maybe the only ones, but we were one of the very first ones, are standard today. Meaning we posted multiple stories as it built, got more information, had punchy headlines, tested our headlines. It's just hard for people to switch, which medium. So Businessweek doesn't worry about their headline in the magazine. Is it a good headline? Give them more revenues? Doesn't matter. Doesn't matter. Care about the cover, but they don't care about the headlines of the articles. And so we would try four headlines, which was incredibly innovative at the time, for five minutes a piece. And then see, oh, this one is pulling better. Let's use that one. So all these things are absolutely standard today. And Henry was very good. I mean, he's incredibly talented. And we got Peter Kafka, some people who are still very significant journalists today. We got them early on in their careers, but it took a long time. I mean, it took years, but luckily we had enormous growth. Also, it was hard to raise money for it. Our strategy was, we're never going to do marketing. So by the way, you've never seen an ad for Business Insider. We're going to write stuff that's so good that eventually we'll have a hundred million uniques. And everyone's like, that's not a strategy. And hope is not a strategy. And that is exactly what happened. That's what I did just before breakfast. I did what I do every morning. I took some creatine. Today I took five grams. 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Go to Shopify.com slash Tim and start your free trial today. One more time. That's Shopify.com slash Tim. Now you have, how many full-time employees do you have at Alicorp now? 23, 24. Okay. So still not gigantic. All right. When you go back to yesteryear, back when you and Dwight, maybe there were one or two other people, how did you do the opportunity analysis to decide on what you were going to launch? How did you stress test what seemed interesting? Yeah. No, it was just the two of us. Right. Great. So how did you choose what to do? Literally just sitting there in the conference room, brainstorming ideas, talking about it, thinking about it. Sometimes we'd go months and had nothing. And then you have to just trust at a certain point that it'd be no different if you met someone who's single and is out there dating and said, how do I know this is the person? You have to hope you know when you know. What does it feel like to know with some of these ideas or any others, but preferably earlier examples? What does it feel like? I recognize it because I start with a business crush, meaning there's an idea and I can't stop thinking about it. And then a week later, I'm still thinking about it. And now I'm thinking, oh my God, this would be good. And we could do that. And we could have this person. And it's just building in my mind. And I'm falling in love with my idea intellectually. And if that sticks with me for two weeks, I generally do it. I don't actually spend more time. I know if I feel it and see it because there's no sense doing a business model. I mean, you know, who knows how many people are don't know that, you don't know anything. The question is, are people going to read their business news online? Can we do a better job than the established players? And can we do it differently? Do we have a vision for that? In the beginning, I want someone who is going to focus on product. I don't need a finance person. I don't need marketing. I need a great product. And Business Insider was a great product, which is why we got to 100 million. And Guilt was a great product. Also, Business Insider was, in a sense, in your sandbox, because presumably it's dependent on advertising, right? So you knew that once you had the eyeballs, you could develop that as a business. Yeah, but it's harder to get the eyeballs than it is to sell advertising. If I hand you 100 million uniques, you just go out there, hire a guy to sell advertising, and he'll sell. Getting 100 million uniques is 90%, 95% of the job. At what point in the process are you like, you know what? I know exactly the process. at Union Square Ventures or fill-in-the-blank, friendly VC who would love this idea if we can show a proof of concept. Yeah, no, I don't think that way. And I'm always wrong. Sometimes I'll think, I bet this person would like it. But the way to do it, once we go out to raise money, then at the time, we would go out to 20 firms, 25 firms. And half the time, the person I thought wanted to do it didn't want to do it for whatever reason. And someone else fell in love with the idea. So I don't reset that. I'm always shocked by it. Got it. The fundraising is, we'll solve it later kind of situation. I never pre-spell. Also, I never think about exits. We need to focus on the product. Do we have a product that everyone wants to use? If you solve that, everything else follows. You can raise money. You can hire people. You can do everything. When did you guys, and I'm going to mispronounce this, invest in Valor Atomics? Is it Valor? Valor. Valor. Valor. Yeah. I had a 50-50 chance. That's V-A-L-A-R. Yeah. When did you guys invest? Nuclear company. Three years ago. Three years ago. Not even three years ago. Okay. So this is, right. Small modular nuclear reactor. Exactly. So the next-gen nuclear reactor. How did you approach this? Because, you know, nuclear is, pun intended, hot. It wasn't hot. It wasn't. No. Because fusion was kind of on fire. I mean, you had the Commonwealth fusion systems at MIT and you had Sam Altman raising money. He was raising his SPVs. I guess I'm wondering how you decided on that investment. Yeah. And so this came directly from my deep tech team. So it wasn't my relationship, but we just thought like always that there's an incredible team idea and that they're going to execute well. It was at a $20 million valuation three years ago. They just raised, it was announced publicly from Sequoia at 6 billion and they have been crushing it. Where we got lucky is that the U.S. government was not behind nuclear. At that time. And I'm not always the biggest fan of the Trump administration, but on psychedelics and nuclear, I think they're right on both. And they have moved both of them forward in a very substantial way. Yeah. I hope you talk to some nuclear folks in here in China because they are crushing energy production. Yeah. By the way, most people know France is, must have 70% of its energy for 50 years from nuclear. Absolutely no problems. Great thing. Stable. I am convinced that this should be an important part of our energy future. Do you guys, as the companies, the portfolio companies are raising money? I mean, that's a crazy markup, right? I mean, just an amazing markup. Does Alicorp take money off the table in these large rounds along the way strategically, or do you guys just park it and wait until the end? How do you think about handling that? We've done it once so far. And in the past, I would personally take some money off the table, the QSBS-enabled money, which can make sense. That's a small business exemption for tax purposes for people listening under whatever the asset cap. Yep. You get $10 million tax-free. But in general now, we think it's a good idea for a smaller fund like us in rounds four or five years in to sell a third of our position. So over the next year, we will be hedging in some ways and we'll go out there, even though we feel good about these companies. But I think that's a good idea. I think that's a sensible thing. It returns some money to everyone. It returns some money to the team. And, you know, some of these will do really well, some won't. So I think that's a good idea. What does your LP base look like? It's very small. I'm the largest LP. And then we have mostly family offices and some institutions, some small endowments. So we have maybe 40 or 50 LPs. I mean, you have a spectacular track record. And the second fund, correct me if I'm getting this number wrong, or correct me if Astra's getting this number wrong, July 2026, $335 million second fund, something like that. Yeah. The first fund is at the end of this quarter will be roughly at 60% IRR. And my family office, the fund you were talking about before also is at 60%. And the $335 million fund is in that ballpark. We haven't had anything to date in our three sort of funds that's been below 50% IRR. So we've been very lucky. We've had some great companies and things are going really well. You could raise a huge fund if you wanted to, right? And maybe you could do more follow-on investing. Maybe you could have a separate fund for growth rounds, et cetera, et cetera. Why not do that? What are the reasons for not doing it? What I like to do and what I think we are very good at and the team like to do are build companies. Whether we start them, most of them we're investing in. And we think a lot of the true value add is in those first five years. There are plenty of funds that are big. We're not trying to collect assets. You know how VC funds are typically 2% and 20% on the upside. Big funds focus on the 2%. We focus on the 20%. I don't want to be in that business of accumulating assets. Our funds will get bigger, but it'll because we add verticals. We add some time. We might add a geography at some point, but I want to keep doing what we do well and what we find fun. I got to wake up every day and feel like I love what I'm doing. And I think we're, in our own small way, helping to change the world. You mentioned Zola. There'll be, I don't know, 150, 200,000 couples this year who will use a wedding registry. That was an idea I had 12 years ago. That's great. The nuclear company, I sat down and had drinks with the governor of New York three weeks ago. She's doing a great job. One of the things you want to talk about was nuclear and how we can bring that to New York state because we need to lock down and get more energy costs and bring down costs of energy and help people. And I think we need to help data centers. And we're a part of these things. And psychedelics, I hope there are, we're sitting here 10 years from now, I hope 100,000 people who have PTSD have been helped by methadone because we discovered that compound and are going to help bring it to market. Yeah, we can chat about methadone. That's a beautiful molecule and we will talk about it. Before we get there, I want to take a break from some of the investing stuff just for a moment. How did you end up pursuing a serious level of ping pong? In high school, I played, I had a table in the basement. So I was one of the better people in my neighborhood. And then we had a high school tournament. And then I saw from here and I won that. And I realized I was pretty good. Then they had a regional tournament. So I went to that and I won that. And then I finally found the state level tournament and I got my ass handed to me there. Then I started playing in New York because New York has great ping pong. Was that the defeat that you needed? You were just like, oh, okay. Yeah. All right. Well, I just didn't play enough. I didn't have a coach. I was just playing in my neighborhood. So then- And then I found a ping pong club that doesn't exist anymore on right near here on White and Walker. Found a guy named Musa, who was the 14th in the Olympics in 1992. He's from Nigeria, the freak of nature. And started playing with him. So then I played some tournaments. And then when I went on the board of Yale, I called up the ping pong team and said, hey, can I come play with you? And they're like, sure. And then I went and played with them and realized that I could hold my own there with the varsity team. And so I would go play with them. I still do when I can get up to New Haven. And so I just like to play with, you know, I'm not incredible, but I'm pretty good. How often do you play and what kind of coach or coaching do you have? So I actually weirdly still play with Musa and then with another guy as well. My son is pretty good. And so he, you know, he's 28, he's in New York. And so we'll be playing tomorrow, actually. So I probably play every two or three weeks. I just love it. It's incredibly fun. Seems great for your brain. The Chinese will all say, and I think they're not, that it's unbelievably good because brain is hand-eye coordination, reacting extremely quickly and subtly. And so that's got to be very good for you. Talking about the brain, we are going to get back to meth alone, but I want to talk about vacation first. Got a quote here. Again, feel free to fact check. This is attributed to one Kevin Ryan. I think everyone should take four to five weeks of vacation. I would rather have somebody who works 47 weeks of the year pretty intensely. And then it says, knowing that his CEOs will be influenced more by his behavior than by policy. He takes eight to 10 weeks off annually now, but you're not entirely off the grid when you take that time. So can you tell me what your split looks like? And was it the same in the early years of Alley Corp? Like how long has that been the case? I told all my CEOs that when I was building DoubleClick, obviously, as you heard, pretty intense. And we went public 24 months after we started just another project. Different world now, huh? Yeah, it was a good old days. And I knew I had to change my life. And I could only do three things. That family, I took my kids to school. I got it. So you're burning the midnight oil on that one and that led to the realization? Yeah. And I, I, I've never burned out at all because I pace myself. And so I needed to be working hard, spending all the time I needed to with my family and staying in shape. Everything else I cut by like 80%. And that's costly. That's time with friends. I used to be a guy who'd do the cool cultural things all over. You know, I used to watch my twenties sports on Sunday afternoon, all gone. I prioritized those three things. And then, you know, eight years ago, my kids went off to college and things, and I could layer in new things and different things and have more time. And so some ways became more interesting. I didn't ever want to be in a situation where my kids are 18. And I thought, oh my God, I didn't spend time with them. And we did spend, you know, at least four to five weeks vacation doing great things together, great memories. That's extremely important. Today, I spend eight to 10 weeks out of the office. I do work every day, but sometimes it'll be two to three hours, just keeping things moving. I can do that. And sometimes it's, you know, a full day. Like I'll be week after next, I have a wedding and a visa. So I'll be there for four days. And the first five days before that, I'll be in my house in France. And so in the morning, I will be doing intensive sports, incredible biking there. You need to come at some point, great biking, tennis, swimming. And then I have already blocked out that I'll do the three hours, nine to 12 New York time locked in for meetings. And then one of the days I'll also do the night shift. So I'll do eight hours the next day, but that's an amazing day. Or if I ski in France back by three o'clock and then work from three till eight 30, and then have a great dinner. It's an incredible day. That is an amazing day. How to change your mind by Michael Pollan. What did that do for you? I reached the age of 54, which was eight years ago and had never thought about psychedelics at all. Certainly never tried anything and didn't know very much. Read the Michael Pollan book. It was on the New York times in 2017, 10 best books of the year, which is something I always go over to see what I should be reading there. Read the book and it literally did change my mind. It was called how to change your mind. And I realized later than most people that I was wrong, that these medications, these medications, these medications, these medications, these medications, these medicines could be very useful for people. And that there was a lot of academic results, even at the time that showed that they could help PTSD and depression and anxiety. And at the time I was still on the board of Yale. So I went and I realized that Yale, I think you talked to John Crystal at one point. Interview John Crystal on his work on ketamine foundational work with respected depression and much more. Also I've had conversations with Ben who I'm so happy for. I just spent a week in the desert with Ben. Never met him in person. Oh, fantastic. And so John Crystal is great. I'm trying to get together with him in the next couple of weeks. Realized Yale had done amazing work, got them all there. They have a Yale center for psychedelic research. And I just became persuaded in terms of long-term trends. I wasn't thinking about investing at all at the time. I was just thinking, this is something I am persuaded that most people don't realize is going to be very effective and very important. I'm probably one of the bigger donors to the Yale center for psychedelic research doing great work. Then in 2021, I decided in talking to Ben Kilmendy, who was a professor there, that the next phase was going to be a for-profit phase. And it was the right thing. And the reason is it takes, whether we like it or not, it takes roughly $200, $250 million to get one compound through the FDA process. And I wish that were less, but it is what it is right now. And we're not going to be able to raise that money from a nonprofit point of view, even though you contribute, not going to be enough. And so then I said, you know, we should look and see if we should start a company in this space. And then worked with Ben and a guy in my team who was on the Alicorp team, Blake Mandela. And so we worked on the idea, came up with this methadone largely due to Ben and then said, let's start this. We think it has very promising. Blake spun out of Alicorp, which sometimes happened to be the CEO of the company. And then we started the company. Yeah. Methadone for people who don't know, I want you to hold me back here, but methadone, if I were describing it, I had my first methadone experience, probably 2015 early, but it had to basically fall off the back of a truck. It was very, very hard to find even on the underground, but an incredibly beautiful, gentle experience. And maybe the soft spoken, shorter staying cousin of MDMA. So rather than coming in and you're like, when's this guy going to leave in six hours? It's more like, wow, that was so pleasant. Came over, didn't overstay his welcome. So I'd love to hear how you landed on methadone or just whatever you'd like to share about methadone specifically, because I think it is, it was just the bullseye. I mean, what a good choice. What a good choice in terms of the horse to bet on. Let's start there. Let's start with methadone itself because it's one that many people will not be familiar with. Yeah. And even more so at the time from a business point of view and impacted society point of view, we wanted to find something that people didn't know about, but had some preliminary results that meant that we thought there was a, you know, that it could be impactful. And so what most people didn't realize at the time that it has some advantages over MDMA. And by the way, I think MDMA is fantastic, both recreationally and therapeutically. The results in the trials were very good, but there are some advantages. And so what you were referring to, put another way, you can take methadone once a week in our trials. You actually can't take MDMA once a week. It's a little bit more toxic. It depletes your serotonin. A little bit more. Yeah. Sasha Shulgin would say if more than four times a year, it loses its magic. Yeah. A lot of people become resistant. Yeah. Non-responsive. And so sometimes a slightly softer substance has advantages. Also, you tend not to have the downer that some people have in MDMA. And the duration of action is much more compatible with healthcare as we know it. Yeah. Right. So it had those advantages and we still don't know until you do a full double blind study. And so then we started that process or raise the money. And the results ended up to be incredible. And the results, this is within the indication of PTSD. Yeah. We have a patent for PTSD, depression, and anxiety, which is very valuable. So no one else can use it for 20 years in these three categories. But you can only start with one indication because it's $200 million each time. And at the time, if you remember two years ago, we went through a period in psychedelics where it was the desert period. It was hard to raise money. It wasn't easy. So there was no way we were going to be able to do all three. Well, I think part of the reason it was hard to raise, there was stigma, but there were plenty of enthusiastic capitalists who wanted to make something happen. I think there were a few common mistakes. One was assuming it would be easier than it is to get something that lasts four to six hours. Let's just call it. You have to prove that it can be scalable as a treatment. You can deliver a certain quality of care, but what does that mean? You have extra nurses, you have extra people, and suddenly the cost is very out of reach. Separately, I would say the combining, we saw this with Lycos, the combining of psychotherapy, the bundling of psychotherapy. And then you put it in front of the FDA advisory committee and they're like, "We don't know how to evaluate or standardize psychotherapy." And since we don't, no pass. I mean, there's a lot more to that story as you know. How did watching the ecosystem, maybe seeing some of the early unforced errors, how did that impact your numbers, inform how you guys approached Methylene? It definitely did. And there's a saying, the early worm gets the bird, but the second mouse gets the cheese. Oh, the early bird gets the worm, but the second mouse gets the cheese. Yeah. So sometimes it's better to be the second mouse, first mouse gets smashed. First mouse gets smashed, the cheese is still there, and then you have it. It's like the iPod. Yeah. So we tried to learn from what we saw out there and change certain things. I think also the FDA has changed over time and the Trump administration has sent a signal that they would like this to happen. And I think as you know, I mean, you were super early in 2015, but now I would imagine that huge percentage of your random friends have tried psychedelics. Oh, sure. Yeah. In 2015, that number must have been small. Well, it was small. And unless you happen to be like me living in the Bay Area, people were pretty, mom's the word about it. Yeah. I mean, there's some. I think maybe the pendulum in some cases swung too far. It's like, if I have to listen to one more trip report about neon crocodiles, this is like listening to somebody's dreams every morning. It's like, okay, I get it. At the same time, yeah, it was very different. And I mean, look, I don't want to take us too far afield, but even though I did a podcast on Ibogaine in 2015. Did you really? Wow. I did. Wow. Yeah. With Martin Polanco and Dr. Dan Engel, looking at some of the work that was being done in Mexico. But it was way, I mean, this is the early days. Wow. You were early. Yeah. First 100 monkeys shot into space, right? I was not going to sign up for it, but I never would have guessed that Ibogaine would have been the one that gets mentioned in the Oval Office as an executive order is being signed. And in retrospect though, it makes a lot of sense. And I have to imagine the application of PTSD to this politically immune group. Like if you're on the left or the right as a politician, you cannot say fuck the veterans. That the indication of PTSD to this politically immune group, like if you're on the left or the right as a politician, you cannot say fuck the veterans, that the indication of PTSD also as sort of a tip of the spear has that benefit. It does. And one thing I haven't mentioned to you is that We set up Transcend as a public benefit corporation. Yes, I wanted to talk about this, yeah. And that means that the initial shareholders had committed to give 10% of their gains to what is essentially a foundation and that Blake and I will be giving out that money. And so we will be giving $20 million in the next nine months to causes linked to psychedelics. And so we're in that process right now. I've hired a part-time person to do that, but it has come up because we focus on veterans for PTSD for political reasons, we being the entire industry. The number one source is sexual assault. And that's why our trials were actually 60% women because more women have PTSD than men. And I think it's a little bit undercovered. And so we're gonna look into some causes and support that and try and see if we can give some of that money out into that area. So I guess I have a few things. The first is kudos to you. And I want you to correct me if I'm wrong, but like a public benefit corp has its charter, its stated mission. I've interacted with a number of them, but ultimately I remember one of the questions I had for somebody else running one of these. And I was like, well, if you change your mind later, how are you held accountable? And he was like, silence, right? And I was like, you can kind of break the rules and get away with it. So the fact that you guys are following through means a lot. How are you thinking about, I'm sure it's not just an open casting call because you'd get a million whack-a-doodles and beautiful things in the inbox that somebody would have to comb through. How are you thinking about how to allocate that 20 million? So we're still thinking about it. We already have 50 organizations that I'm not meeting with companies. Yeah, you seem like a busy guy. Yeah, but Nicholas Boileau, who's the person who is in charge of this, has been meeting with people. We're assembling it, looking at the world. There's going to be a big PSFC meeting in October. And then we're going to start. This is the Psychedelic Science Funders Collaborative, although now they've expanded beyond just the science, but in PSFC. But it's the largest collection of donors in the psychedelic space. PSFC.co, I think. Yeah, they do great work. But the point is what we're going to look to do is not make, you know, 500 grants, but make like 20 and have real grants. Most of these organizations are small. So, you know, there's a good chance we'll be the largest donor to the psychedelic industry in the next 12 months, just for 12 months. And I don't. I don't have the full answer to that yet. We're starting to think of where can we have impact, what can be done that other people are not doing. We probably won't give as much to pure academic research. You know, even in Oregon and Colorado, who have legal psychedelics. Or at least decriminalized. Well, there's a program in each state that is legal to give it out and be able to do it. Yeah, right. With the sort of parallel structure, yeah. Yeah. But not even 0.5% of people with depression or PTSD have been able to access this yet. One of the biggest challenges we have is it's too expensive. And, you know, one of the things I am interested in is trying to show that group therapy works as well, which I think may be even better in some cases. I think it may be even better. My bet would be better. Same here. There's a reason that AA does it in a group setting because you get support from other people. And you've probably been in some group ceremonies and they can be very powerful. FDA has been very nervous about that. That's a whole new thing. How do you monitor that? So we need to get to the point. We need to bring down the cost is the bottom line. What would your hope be for the for-profit ecosystem? Would your hope be that more people would follow in your footsteps? If so, how can they, as the better version of themselves or the best version of themselves, ensure that when incentives get really tempting later, they don't change their mind? On the public benefit corporation? On the public benefit corp. Exactly, right? Yeah. I have been. Incredibly disappointed with how many centimillionaires, billionaires have had their lives changed by these things but have in no material way supported the ecosystem or the science upon which ultimately a lot of the work depends. It's been personally very upsetting to me as someone who put like 20% of his entire net worth in at one point. That is not to say that I think academia is the cure-all for all the reasons you said, like the market-driven solutions, for the very expensive FDA processes involved. Incredibly important. What do you think can be done to encourage people? I mean, you're doing a great job by doing it, right? Just showcasing it. And I think a lot of good will radiate from that. Any thoughts on how to encourage more people to get involved? I don't know how to, you know, force them. But what I know I'm doing is I'm actually having a series of conversations with people and talking through. You have called me and what I'm doing, I'm going to be speaking at the smaller PSFC group to give an example of why we did it this way, what we did. You know, we did it for a couple of reasons. One, at the end, we thought it was fair. Two, it reminded everyone in the company that this is a mission-driven company. Yes, at the end, it may be a good exit, but we are doing this and everyone needs to join this company because they want to make the world a better place and we want to help these people who have PTSD. There are 10 million people and it's a real problem. And then eventually depression as well. And so everyone joining knew that the original shareholders, board members, chairman had already committed to do this and we're going to put their money where their mouth is. And I think we just have to push everyone on this to do it. I don't know a better way to force them. Well, I'm so glad you're doing it. I hope more people follow suit. Friend of mine who's a VC, he's very successful as an angel, joined a venture capital firm, very well-known, did incredibly well. And a while back, he started kind of stepping back and I've had people suggesting I started fun forever. And I, for a host of reasons, I'm not convinced I'd be good at it or particularly enjoy it. I don't know. But he said, oh, early stage venture's dead. And I was like, what do you mean early stage venture's dead? And what he meant was, if your bread and butter is a lot of consumer facing tech, he's like, I just made a clone of Twitter in 12 hours as a non-technical person using, you know, vibe coding and X, Y, and Z. Ultimately, that's not enough to just displace X. But is the deep tech focus because there are more defensible moats in deep tech or is there more to it? It's partly that, but it's also probably that world is changing. So in that consumer idea you're talking about, you know, there are 164 soft drinks. The odds of you coming up with one that stands out is pretty slim. Whereas the changes that are occurring or have occurred in solar or wind or geothermal or nuclear, you know, there are going to be billions and billions and billions of dollars of contracts signed to produce energy. Robotics, the same thing. We're seeing extraordinary developments. We're getting 10X and 100X improvements in robots, which will change the world. I just don't see the same thing in e-commerce. Healthcare can change. It can be done better in this country. We spend a lot. We don't have great results. Complicated issue, but that's why, you know, we really do what I call traditional software. AI is one group. Healthcare is one group. And deep tech is one group. Those are our three areas of focus. We have dedicated teams, but we do more deep tech than we did four or five years ago. Absolutely. That's the one that's grown the most for these various reasons. And it's intellectually interesting. You learn a lot. Space. We have an investment in space. There's a company called Portal that can help move, satellites from one area to another. And there's just a whole ecosystem. That's sort of a second order implication of having 10 times more satellites, which we'll have. On the robotics side, what are some second or third order effects that might present opportunities? Because investing in someone who actually like a Boston robotics way beyond my pay grade, but I'm like, maybe if that's where the focus is, I'm saying this in a very simple way, but if a lot of people are focused on that, maybe like the second or third order effects are more in the, in the first place, I think that's a good thing. Yeah. So let's look at the movement and societal shifts and are there gonna be more robots in 10 years? Yeah, I think so. Right. A hundred times more. I mean, this is one where it's literally gonna be somewhere between a hundred and a thousand or 10,000 times more. And so I think the business opportunities are gonna be in very vertical uses, a textile factory, things like that, or a car factory or things like that. And so, and those are happening right now and they're gonna continue to happen where it's harder is in. Yeah. Things like a restaurant, because robots are best early on when they can do one thing and do it really well, when they have to chop vegetables, take the garbage up the stairs and go to a nearby deli to buy a product that we need humans can do that quite well robots, that's a tougher, so single use is the best way in factories are the best way for that. So that's gonna be colossal in every single factory. Are you still bullish on robot massage and to what extent are you looking at? Unfilled jobs as a, maybe one criteria. I am bullish and we're, you know, we were an investor in escape, which is doing that. That's a product that's still evolving, but it's going to work. I remember as of two years ago, there were 17,000 unfilled jobs in massages in this country. And you must have gone to a hotel like I have and you arrive, you're like, yeah, can I get a massage tomorrow afternoon? Like, totally booked up. Yeah. How about three days from now? - Yeah, and you're like, I'm not gonna-- - 9:00 a.m. and you're like, no. - I'm not gonna be in the hotel, or you say 8:00 a.m. or 9:00 a.m. no way, no one works at that time. 7 p.m., no one works. If you had a machine, and 25% of people prefer to have a robot. Some people think it'd be much better to have a person. There are a lot of people that don't like to take their clothes off, don't feel comfortable with it, and feel better about a robot. So just another example of something you wouldn't think of. It is a solvable problem, and we're probably 70% of the way there to solving it. Any other jobs with lots of unfilled positions that make for appealing terrain? Again, we haven't solved the restaurant one, and that's a big one. I wonder, I mean, to what extent, man, I'd love to have a conversation with Travis Kalanick about that. Man, he is more than anyone I know, so he put a lot of thought. Yeah, and he is industrializing, so he has a better chance of doing it. The truth is most restaurants are big mom-and-pop shops, and so it's harder to do that. But yeah, I mean, we're doing it. We're doing it. We're doing it. We're doing it. We're doing it. We're doing it. We're doing it. We're doing it. We're doing it. We're doing it. We're doing it. We're doing it. And after 15 seconds said, I'm sorry, would you be more comfortable in another language? And the person said, well, actually, yeah, could we speak Spanish? And he goes, muy bien, and then just handles the rest of the call in Spanish. What a cool example. And if you listen to it, it changed completely the call, because she had trouble explaining. It was a medical thing. She had a lot of trouble explaining in English. And then right away, no issue, and solved the problem. Yeah. Wow. It's coming fast. It is coming so fast. If you think of an example of one of the companies, ideally one that you co-founded, that was like pushing a boulder downhill, it's like, wow, this is really, things just fell into place in a sense, ideally not just through luck. And then one that was pushing a boulder uphill. I'm wondering what the biggest difference is. Like what comes to mind and what were the differences between the two? I'll give you a good uphill one, which I'm still disappointed at. We realized there were going to be a lot, it was basically Shopify for healthcare companies. Because we were building these healthcare sites, and we found we were building a lot of the same things. Scheduling for time, and this is three, four years ago. Scheduling, information, all the stuff, didn't matter whether it was for your cancer care or your back problem. A lot of repeating features. And it has to be HIPAA-compliant. HIPAA-compliant, which most sites are not. So we set up a company to be Shopify for healthcare sites. For whatever reason, we put $6 million in, eventually it just didn't get there. People were reluctant to sign up. They didn't see someone else. Maybe it wasn't good enough execution. Felt like that should exist. And we never pulled it off. And then had to make a decision to close it down. Doesn't seem like you were too early. Are the reasons unknown? They are unknown for me. Did we not do a good enough job? Did we have to wait just another year to get the first marquee clients? And that was enough? Obviously, most companies at the time were reluctant to outsource to someone else. So I still don't, I don't know. And sometimes you don't know. It's not, it's still not quite a playbook there. Now, DoubleClick was public 24, no, 48 months. What happened? No, no, it was public for seven years. Oh, I'm sorry. After it's formed? Oh, yeah, yeah. 24 months after we started. I mean, there's like marketing conditions and all that stuff also. But then you have something like MongoDB. That was a decade before IPO. Why was that? First of all, we didn't have any revenue for three and a half years. And if you're taking notes, don't do that. Because it made it hard to raise money. It's a hard product. It's also, if I said a database is like a pacemaker. If I said to you, I've got this startup pacemaker idea. Do you want to try it? And you're like, no, no. Call me when a thousand people have used your pacemaker for two years. But if everyone says that, I can't get my pacemaker out there. So it took us a long time. We had to give away for free for a long time, used for inexpensive things, and then slowly got there. So even after eight years, we were doing 40 million in revenue, which is not that much. But the usage was growing dramatically. The product worked. The product was getting better. And today it's worth, I don't know, $30 billion. And it's an incredible company. What are your personal rules for what you do when a company goes public? What is your policy for holding, selling a portion, selling all? How do you think about that? Because I know some angels, they're like, look, public market, not my game. As soon as it goes public, I'm going to sell 50% and then just let the rest ride. And they keep it really simple. I definitely don't have a policy. I hold it as long as I still feel this is a great investment. And I think it's going to grow for a long time. At some point, you do need to get money if you have a firm to invest in other things. So I did not sell in the first year or two when it was public. And then the price went up and I just slowly started selling. And I still have shares today, but I've sold a big percentage of it over time. We're going to land the plane now. So Kevin, if you could put anything, metaphorically speaking, on a billboard to get a message in front of millions, billions of people, we can just pretend that they all speak English. They, I, you know, I can figure it out. But what might you put on that billboard? Could be a motto, could be a quote, could be anything non-commercial. Does anything come to mind? So I'll give you something different than you think. I would love the United States to be a more balanced society and a more open and a more caring society that we take care of other people. I'm not worried about our startups. Our startups are doing great technology funding. All that's great. Lots of entrepreneurs. I do worry long-term about the income inequality in this country. I don't think we're addressing that issue. I think the ability for people in this country to move up the ladder statistically has been very, very low. I don't think we're being diminished. And I think all of this is going to catch up to us. And it's not right. People have schools that are bad. They don't have support. We're going to have this transition. There's no doubt. We can debate the time. We're going to lose jobs to AI. And I don't think we're in a good position to help people have successful lives. So I would like the country to be thinking about that. So whether we're at the highest levels of state government or you're in the mid-20th century, we're going to have to pull two levers. What are the levers to try to make a bit of progress in addressing some of the issues you just mentioned? One that's going to lead to, we're going to have to address the budget deficit at some point. We don't know where that point is, but it could be sneaking up on us right now. We're going to have to end up having a more equitable tax system where the wealthy pay 30% taxes, which they don't right now. We have to decrease that budget deficit because that decreases the interest rate, which impacts everyone to do that. And then we're going to have to just agree that we're going to do a better job of helping people go to the right colleges, get the right degrees. I don't mean necessarily college degrees. I mean professional training, retraining, things like that. We have to get to the point where a higher percentage of people are doing well and they feel like their kids are going to do well. When families don't feel like their kids are going to do better, they get desperate and they go to the far right or they go to the far left. And neither one of those solutions is going to be the right solution. We're going to have to get more immigrants in this country. How do you think you do that? Because I agree with you. And I mean, I've seen so much headache in say recruiting in Silicon Valley and this, that, and the other thing. It's wild. I mean, this is a country of immigrants. So how do you think you tackle that? The message has come down in the last several years from the president that immigrants are bad. And I just find it unfathomable. And everyone in Silicon Valley that has been supporting this has made their money backing immigrants. Yeah. It's pretty gross. I mean, look, should we have unlimited people coming over the border? Absolutely not. No one's saying that. Should my companies have trouble getting PhD people in AI to come from other countries to come to the United States? How is that a good idea to stop those people from coming in? We should be opening our doors and saying, you have a master's in AI and computer science and like that. Of course you can come work here. Come work here. You think they're going to go on unemployment? I doubt it. They're going to make $500,000 a year and they're going to join some company. And three years later, you're going to start their own company, employ 5,000 people. I mean, as you said, we're all immigrants. This should be the country where the most talented people in the world are coming to right now. And we shouldn't take a hundred million of them, but we should take, you know, a million of them, two million of them. Population is going to be going down. That has some negative impact on us. We should be supplementing that. Our entire history, our immigrants do great. Now the data shows our immigrants from Haiti do great from Nigeria do great from Kosovo do great. They're just scrappy people who want to work their ass off in whatever they do. And I want more of them. And that's a contrarian view today. I agree a hundred percent. I mean, I've, I've seen the same thing where it's like, okay, let me get this straight. You're going to keep these PhDs in X, Y, and Z out of the country. And guess what? They are talented. They're going to get used with great leverage and they're going to create something incredible. The question is, is it going to be here or not? Yeah. At Yale, we're seeing pressure on not getting academics in on some academics feeling not comfortable. You know, we had a one who left for Oxford and Cambridge, people left to go to Canada. That should not be happening. The premier league in English soccer is the best league in the world. Not because of English players, because they have Norwegian players, they have players, they have people from Ghana. Basically, they don't care. They want the best. people. And that's what we have always been and need to continue to be. Kevin, before we wind this to a close, anything else you'd like to say? Anything else you'd like to point people to? People can find Alicorp online, of course. It's spelled as it sounds, alicorp.com. I'll include the LinkedIn and AlicorpX and all these things in the show notes. Anything else you'd like to. The only thing I'd say, and the fact that you're in New York for a month or two makes the point that New York is just booming. And we had an incredible summer with the Knicks and the World Cup and the US Open, but the restaurants, the startups, I could not feel better. We're very focused on New York, but I see so many people moving from Europe, coming to New York, starting up companies. Mongo was run by someone who was an immigrant. Datadog was started by French entrepreneurs. Those are the two most valuable tech companies here. Despite what I said, we're going to get more people coming here. New York's going to be very, very successful. It's on fire. Yeah, it's really on fire. I mean, home base is Austin. Austin's a boom town for a million different reasons. That's not going to slow down anytime soon, but New York is New York. There's just. Having grown up as a New Yorker, it continually blows my mind. But this particular season, this season of New York has been just on fire. It's really exciting. And the higher level thing is the more I go, I spend a lot of time outside the United States, but the United States from a business tech point of view is just crushing it. And we all see this, but the future industries, and we have to worry about China because China is doing a lot of great things, but we're doing a lot of great things. And everyone in Europe and Latin America looks to us and is both concerned and impressed. Well, thanks for the time, Kevin. Lovely to see you. And for everybody listening, we will have links to everything in the show notes, tim.blog.com slash podcast. The one and only Kevin Ryan, just type in his name and everything will pop up. And until next time, be a bit kinder than is necessary to others and to yourself. And thanks. Hey, guys, this is Tim again. Just one more thing before you take off. And that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and 2 million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over the years. And I'll see you in the next one. Bye. That week, it's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums, perhaps gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field. And then I test them and then I share them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. 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