Tim Ferriss 
Please enjoy this transcript of my interview with Kevin Ryan, one of the leading entrepreneurs and investors in New York. Often called the “Godfather of NYC tech,” he is the founder and CEO of AlleyCorp, a New York based venture capital firm that incubates and invests across healthcare, AI and software, consumer tech, deep tech, and more. Kevin is also the co-founder of several notable companies including MongoDB, Business Insider, Zola, Gilt Groupe, and Transcend Therapeutics. 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.
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Tim Ferriss: Kevin, thank you for making the time. So nice to see you.
Kevin Ryan: Happy to be here.
Tim Ferriss: 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. 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. Then 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 Gilt Groupe, Business Insider, 10gen later renamed 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’s Bay buys Gilt Groupe for announced $250 million deal. MongoDB in 2017 goes public on NASDAQ 10 years after its founding. I know 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-founds Transcend Therapeutics, developing new medicines for psychiatric conditions. And 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 up front plus up to 525 million contingent on future sales. July 2026, announces AlleyCorp’s 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. And there’s 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 founders-journey.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 misstep. 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 asks, “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 one or two years, but could you speak to that?
Kevin Ryan: 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 hype-y 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 DoubleClick 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 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 doctor’s practices 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 and I’m not able to think of the right way to benefit from 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 so that’s to learn more, but I don’t have a product idea yet on that.
Tim Ferriss: Why do you do events? Are the events opportunity and talent scouting mostly or are—I understand that learning is sort of a bedrock beneath both of those two, but what was the impetus behind an event like that?
Kevin Ryan: Yeah, so I have four now and some of them are linked to my business. So Deep Tech New York, it’s 450 people talking about the most fundamental deep tech trends that are happening out there, material science, things like that. Then I have one in Digital Health New York, which is next week, Doc, and then I have one that’s called Odyssey, which is just ideas that’s less commercial and just getting a hundred very smart people together. 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.
Tim Ferriss: Could be dragging a hundred pounds sled behind you in Antarctica.
Kevin Ryan: Yeah. I’m leading 20 people as part of Odyssey to China in a month. The theme is what does China do better? There are things they do worse, but there are things they do better.
Tim Ferriss: There are definitely things they do better.
Kevin Ryan: 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. I’m bringing heads of VC firms, a bunch of interesting people on that trip. We did one, took 16 people skiing that are off-piste skiers to a place in Val d’Isère, 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.
Tim Ferriss: All right. 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, 2019, the first thing I thought was, good God, what does this guy do for exercise? I mean, you seem to take, unless your genetics are 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, you got to check some boxes before someone’s going to be avalanche ready 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?
Kevin Ryan: The hiking trip is three or four days. It’ll be probably 30 people and my structure will be probably a four-hour hike, eight till 12, which is a good size hike. You can go longer, but four, maybe five. And then in the afternoon we’ll have sessions. So there’ll be someone talking about climate change. There’ll be someone who’s talking 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.
Tim Ferriss: So with 30, does that mean that you would have something like 10 who end up getting up to speak?
Kevin Ryan: Yeah.
Tim Ferriss: At dinner, is that structured in any way? The reason I ask is that there can be unstructured events. One of the characteristics of Dialog 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. There was frequently assigned seating to ensure that you would get exposed to a variety of folks. 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, right? Is it Jeffersonian or like—
Kevin Ryan: No, at 30, it’s too big to have one conversation. So what I would generally do actually is 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 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 one meal is going to be a 20-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. A good topic when you are relatively well off, how do you handle money with your children? Always a tricky issue when all of us had kids. So wide range of topics.
Tim Ferriss: On the trend side, personally I remember for instance, way back in 2008, 2009, I met Tobi, who is still CEO of Shopify, and they had 10 employees, something like that. 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.
Kevin Ryan: No-brainer.
Tim Ferriss: All right. And Tobi and his team, Harley and everyone were also very focused on being basically first movers on mobile. I was like, okay, well, will there be more mobile phones, more broadband? I mean, that seems obvious, of course. And so ostensibly someone will probably win a decent part of that market. Sure, why not? Give it a shot. 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 multidimensional 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 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?
Kevin Ryan: Well, one of them—and 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, some guesswork in here. But I’m always thinking about, let’s imagine Shopify does very well. Who else works with them and supplies them? So that’s a second order. And so let’s think about that. The people who are providing the picks and shovels to data centers are doing very well.
Tim Ferriss: Yeah, exactly.
Kevin Ryan: 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.
Tim Ferriss: Can you give an example of that?
Kevin Ryan: Well, I’ll give you one example in second order that we sat down in 2003 and 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 by 2005, 2006, they’re going to cross and we should have started YouTube and we didn’t. 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.
Tim Ferriss: That was a good acquisition.
Kevin Ryan: Incredible.
Tim Ferriss: Incredible acquisition.
Tim Ferriss: I won’t belabor this, but I think it’s, well, number one, deeply fascinating to me. If we look at, for instance, Gilt Groupe, and maybe you could give just a brief description of what it was. Why don’t we start there, just very brief, what did Gilt do?
Kevin Ryan: 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, speak French, and everyone in France in 2006 knew vente-privée, which was basically Gilt of France. They were doing a billion dollars in revenue doing this concept of flash sales where during the day, at one moment, they would have a discount merchandise of high-end brands on sale. 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. I remember thinking the person who lives in Philadelphia or Austin, you don’t have sample sales. It’s really the New York brands. There’s a lot of people who’d like to be in that line, and these guys had figured that out.
I started it. It became a phenomenon. So in our second year, we did $175 million in revenue, which is crazy. It’s merchandise, you have to buy it and package it and sell it and return it and things like this. We did an incredible job of providing that. In year four, we were doing $500 million in revenue. This quite a while ago. Then the problem was, which does happen, is the market changed on us.
Tim Ferriss: This is the part I wanted to ask about.
Kevin Ryan: 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.
Tim Ferriss: You had been filling that gap.
Kevin Ryan: I had been filling that gap completely. At the time, Macy’s had a terrible website. They at least got it to mediocre by 2011, 2012. 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.
Tim Ferriss: So this leads to my 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 Gilt inform how you think of durable capitalization on trends? In other words, how you capitalize on that window, but avoid getting crowded out when you have 10 other people do effectively the same thing?
Kevin Ryan: And it gets back to, do you have a moat? 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. I just didn’t quite get there to have an impact on the market. 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. We almost got there, but didn’t. And one of the lessons there, I went to the board and said, “I think we should sell the company.” Everyone’s like, “Well, we were worth a billion dollars. We thought we could sell it for 400. It’s disappointing.” But I said, “We have a falling knife here.” We went out and we only got $250 million. Saks came in and paid for it, and three years later they said, “I’ll sell it back to you for five million.”
Tim Ferriss: Wow. Better late than never.
Kevin Ryan: 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. The conclusion has been that I haven’t touched really e-commerce since then.
It’s solved. I mean, 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.” Right now, I can get anything delivered to my house in 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, cure for cancer, nuclear energy, psychedelics, there are things to be built that have not been built that will improve the world a lot.
Tim Ferriss: Let’s wind back the clock, as I promised listeners earlier. We’re going to get to the helps launch the blank website. Before that, we have Yale, Economics, Prudential Investment Corp.
Kevin Ryan: Investment banking.
Tim Ferriss: Investment banking, INSEAD, Euro Disney. Was there anything that you learned or developed in those chapters that then helped you when you moved to United Media? Is there anything sort of crucial or critical?
Kevin Ryan: 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. All of that was business. I went finance and then going into operations at Disney, we had to manage hotels and it was an exciting project. We launched Euro Disney, 15,000 hotel rooms, 50,000 people every day. Huge project launched one day. I learned a lot about that, but I decided I didn’t want to work for large companies anymore. 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. I was now CFO and COO.
Tim Ferriss: And what is the blank that I’m leaving at here?
Kevin Ryan: 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. I remember reading that thinking, oh my God, that is incredibly cool. We could all be in touch with each other. We can send each other messages. We could buy things. Remember, there’s no browser at the time. By ’95, I launched, because we owned a lot of intellectual property, and one of the things was Dilbert. I launched the Dilbert website, which became extremely successful. 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?
We did our own merchandising, so we started selling t-shirts and ties and things like that. A year later, we had a very successful business. I went to the parent company and I said, “This internet thing’s 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.” 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.”
Tim Ferriss: What’s that even mean?
Kevin Ryan: First of all, I know you don’t know what you’re talking about. There is no next internet. The disturbing part is I remember thinking, you’re just really too old for this. He was exactly the age I am today, 61 or 62. 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.
Tim Ferriss: Was that a gut feeling or were you tracking numbers outside of traffic? What made you feel that conviction?
Kevin Ryan: No, 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 were starting to use maps. You could just see it worked. 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 no-brainer. And so I said, I’m going to go out and start an internet company. I met, 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 know if you remember Excite.
Tim Ferriss: Sure.
Kevin Ryan: A bunch of companies like this.
Tim Ferriss: Drove by them on the 101.
Kevin Ryan: 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 DoubleClick six months before and who were very smart, very technical, and I still have great relationships 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. And then I started for a couple months as CFO, became the president and then became the CEO.
Tim Ferriss: What do you think contributed to that ascension to CEO? What skillset or otherwise contributed to that?
Kevin Ryan: I felt like a founder. Technically I’m not, but I felt like I was. 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 Procter & Gamble, they’re like, “We do business in a lot of countries. We need to work with you.” And then once you had all them, the smaller players were like, “Well, Procter & Gamble and Microsoft, everyone are 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. 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. DoubleClick today as an independent company would be worth a hundred billion.
Tim Ferriss: So I want to talk about that, not exactly building the parachute on the way down, but the AlleyCorp 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. My understanding is, in the early days, you and your partner were putting in maybe 500K each into each company, acting as co-founders, building each for about six months as a proof of concept and then going out to raise venture. Is that a fair description?
Kevin Ryan: Yeah, maybe a year.
Tim Ferriss: A year. Okay.
Kevin Ryan: 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 three. So we did a total of six. Three of them were hugely, hugely successful, Gilt Business Insider and Mongo.
Tim Ferriss: After the formation of AlleyCorp, when were those founded?
Kevin Ryan: All between 2005 and 2008. And the last three were started in the same year.
Tim Ferriss: At that time, were you doing eight companies a year or did that end up later?
Kevin Ryan: No, that much later.
Tim Ferriss: Much later.
Kevin Ryan: Because there was really only two of us. 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 brains behind the DoubleClick technology and the Mongo technology along with one other person. And so we had this great partnership where everything technical, he really handled. I didn’t even worry about. And then everything on the business side, finding the CEO, building it, raising money, things like that, I focused on that.
Tim Ferriss: 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, 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 when in the say first three to five years of AlleyCorp 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 Sam Parr and Shaan Puri, and you mentioned how in the beginning you had a handful of people covering everything. And we could talk about the problem and the gap that that addressed, but just for the time being, I think this is worth spending a moment on.
It’s like in the beginning you had a handful of journalists handling everything.
Kevin Ryan: No, they were only handling New York technology.
Tim Ferriss: Okay. They were handling New York technology.
Kevin Ryan: It’s important to start narrow.
Tim Ferriss: So they handled New York technology and then at a certain point though, I imagine 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 the space. 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.
Kevin Ryan: Yeah. And Gilt and Business Insider, even though they’re very different businesses, we did the same way, which is that Gilt 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 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.
Roughly when we sold there afterwards, we had six people covering defense. That’s great coverage.
Tim Ferriss: When you and Dwight were putting in the initial million dollars, split fifty fifty, presumably you’re taking, I don’t know, 30 plus percent of the company, something like that.
Kevin Ryan: Day one more and then it gets diluted down.
Tim Ferriss: Right, exactly. 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?
Kevin Ryan: Yeah. And 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 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 with—they thought, we’re going to get you in to raise money and help you do that. And we did and we’re able to do that. So that was the pitch. Henry Blodget is a perfect example. He was—
Tim Ferriss: Business Insider.
Kevin Ryan: 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.
Tim Ferriss: Just for clarity, he basically said he was uncomfortable with something that was standard practice. That was his sin.
Kevin Ryan: 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.”
Tim Ferriss: What did the pitch look like?
Kevin Ryan: So the idea is 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 Business Week did not update their sites during the day.
Tim Ferriss: Yeah. Got to wait for the paper.
Kevin Ryan: And so all the things we did, we’re not maybe the only ones, but we were one of the very first ones, our standard today, meaning we posted multiple stories as it built, got more information, had punchy headlines, tested our headlines. So it’s just hard for people to switch mediums. So Business Week doesn’t worry about their headline in the magazine. Does a good headline give them more revenues?
Tim Ferriss: Doesn’t matter.
Kevin Ryan: Doesn’t matter.
Tim Ferriss: They care about their cover, but they don’t care about the headlines of the articles.
Kevin Ryan: 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. 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. It took years, but luckily we had enormous growth. Also, it was hard to raise money for. 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.”
Tim Ferriss: Hope is not a strategy.
Kevin Ryan: And that is exactly what happened.
Tim Ferriss: Yeah. All right. Now you have, how many full-time employees do you have at AlleyCorp now?
Kevin Ryan: 23, 24.
Tim Ferriss: Okay. So still not gigantic?
Kevin Ryan: No.
Tim Ferriss: All right. When you go back to yesteryear, back when you and Dwight, and 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?
Kevin Ryan: No, it was just the two of us.
Tim Ferriss: Okay, great. So how did you choose what to do?
Kevin Ryan: 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.
Tim Ferriss: What does it feel like to know with some of these ideas or any others, but preferably earlier examples, what does it feel like?
Kevin Ryan: 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. Who knows how many people are going to be looking at Business Insider? If you don’t know that, you don’t know anything. The question is, are people going to read their business views 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 100 million and Gilt was a great product.
Tim Ferriss: Also Business Insider was in a sense in your sandbox because presumably it’s dependent on advertising. So you knew that once you had the eyeballs, you could develop that as a business.
Kevin Ryan: It’s harder to get the eyeballs than it is to sell advertising.
Tim Ferriss: Sure.
Kevin Ryan: If I hand you 100 million uniques, you just go out there, hire a guy to sell advertising and he’ll sell it. Getting a hundred million uniques is 95% of the job.
Tim Ferriss: At what point in the process are you like, you know what? I know exactly the person at Union Square Ventures or fill in the blank friendly VC who would love this idea if we can show a proof of concept.
Kevin Ryan: Yeah. No. I don’t think that way. I think, 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 preset that. I’m always shocked.
Tim Ferriss: Got it. So it’s not really, the fundraising is a we’ll solve it later kind of situation.
Kevin Ryan: It’s 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.
Tim Ferriss: When did you guys, and I’m going to mispronounce this, invest in Valar Atomics? Is it Valar?
Kevin Ryan: Valar.
Tim Ferriss: I had fifty fifty chance. That’s V-A-L-A-R.
Kevin Ryan: Yeah.
Tim Ferriss: When did you guys invest?
Kevin Ryan: Nuclear company. Three years—
Tim Ferriss: Three years ago.
Kevin Ryan: Not even three years ago.
Tim Ferriss: Okay. So this is right.
Kevin Ryan: Small modular and nuclear reactor.
Tim Ferriss: Exactly. So the next gen nuclear reactor. How did you approach this? Because nuclear is, pun intended, hot, right?
Kevin Ryan: It wasn’t hot.
Tim Ferriss: It wasn’t.
Kevin Ryan: No.
Tim Ferriss: Because fusion was kind of on fire. You had the commonwealth fusion systems at MIT and you had Sam Altman raising his SPVs. I’m wondering how you decided on that investment.
Kevin Ryan: 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 six billion and they have been crushing it. Where we got lucky is that the US 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.
Tim Ferriss: Yeah. I hope you talk to some nuclear folks when you’re in China because they are crushing energy production gap.
Kevin Ryan: Yeah. By the way, most people know France 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.
Tim Ferriss: Do you guys, as you’re raising or as the companies, the portfolio companies are raising money, that’s a crazy markup, right? I mean just amazing markup. Does AlleyCorp 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?
Kevin Ryan: Yeah. So we’ve done it once so far and in the past I would personally take some money off the table, especially the QSBS enabled money, which can make sense.
Tim Ferriss: That’s a small business exemption for tax purposes for people listening under whatever the asset cap is.
Kevin Ryan: Yeah. You get 10 million tax free and so it’s worth doing that. 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 sensible thing. It returns some money to everyone. It returns some money to the team. And some of these will do really well, some won’t. So I think that’s a good idea.
Tim Ferriss: What does your LP base look like?
Kevin Ryan: 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.
Tim Ferriss: 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?
Kevin Ryan: 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.
Tim Ferriss: You could raise a huge fund if you wanted to 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?
Kevin Ryan: So one, 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%. So 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, but one of the things she wanted 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 data centers. And we’re a part of these things. And psychedelics, I hope there are, if we’re sitting here 10 years from now, I hope a hundred thousand people who have PTSD have been helped by methylone because we discovered that compound and are going to help bring it to market.
Tim Ferriss: Yeah, we can chat about methylone. That was 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?
Kevin Ryan: It just started 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 sophomore year 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 ass my handed to me there. Then I started playing in New York because New York has great ping pong.
Tim Ferriss: Was that the defeat that you needed? You were just like, “Oh, okay.”
Kevin Ryan: Yeah.
Tim Ferriss: All right.
Kevin Ryan: Well, I just didn’t play enough. I didn’t have a coach. I was just playing in my neighborhood. So then I found a ping pong club that doesn’t exist anymore right near here on White and Walker, found a guy named Musa who was 14th in the Olympics in 1992. He’s from Nigeria, a freak of nature. And started playing with him. And 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—I’m not incredible, but I’m pretty good.
Tim Ferriss: Well, how often do you play and what kind of coach or coaching do you have?
Kevin Ryan: So, I actually weirdly still play with Musa and then with another guy as well. My son is pretty good. And so, 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.
Tim Ferriss: Seems great for your brain also.
Kevin Ryan: The Chinese will all say, and I think they’re not wrong, 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.
Tim Ferriss: Talking about the brain. We are going to get back to methylone, 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.” All right. 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 AlleyCorp? How long has that been the case?
Kevin Ryan: Yeah. So, 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.
Tim Ferriss: Different world now, huh?
Kevin Ryan: Yeah. Those are the 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.
Tim Ferriss: I got it. So, you were burning the midnight oil on that one and that led to the realization?
Kevin Ryan: Yeah. 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 80% and that’s costly. That’s time with friends. I used to be guy who’d do the cool cultural things all over. Gone. I used to watch my twenties sports on Sunday afternoon. All gone. I prioritized those three things. And then 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, it’s always became more interesting. But 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 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, but I can do that. And sometimes it’s a full day. The week after next, I have a wedding in Ibiza, 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.
Tim Ferriss: I’d love to.
Kevin Ryan: Great biking, tennis, swimming. And then I have already blocked out that I’ll do the three hours, 9:00 to 12:00 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 3:00 and then work from 3:00 till 8:30 and then have a great dinner. It’s an incredible day.
Tim Ferriss: That is an amazing day. How to Change Your Mind by Michael Pollan, what did that do for you?
Kevin Ryan: Yeah. So, 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 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 Krystal at one point.
Tim Ferriss: Interviewed John Krystal on his work on ketamine, foundational work with respect to depression and much more. Also, I’ve had conversations with Ben Kelmendi, who I’m so happy for.
Kevin Ryan: I just spent a week in the desert with Ben.
Tim Ferriss: Never met him in person. Only fun.
Kevin Ryan: Oh, you need to meet him. He’s fantastic. And so, anyway, John Krystal 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, Ben Kelmendi, who was a professor there—
Tim Ferriss: Superstar.
Kevin Ryan: —that the next phase was going to be a for-profit phase, and it was the right thing. And the reason is, 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 I think you contribute, I contribute, but it’s not going to be enough. And so, then I said, “We should look and see if we should start a company in this space.” Then worked with Ben and a guy in my team who was on the AlleyCorp team, Blake Mandell. And so, we worked on the idea, came up with this methylone, largely due to Ben. And then said, “Let’s start this. We think it has very promising—” Blake spun out of AlleyCorp, which sometimes happened to be the CEO of the company. And then we started the company.
Tim Ferriss: Yeah. Methylone, for people who don’t know, I want you to hold me in check here. But methylone, if I were describing it. I had my first methylone experience by 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
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