Deep Dive with Kevin Ryan

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This is a podcast episode titled, Deep Dive with Kevin Ryan. The summary for this episode is: <p>Tune in to this deep dive episode as Matt interviews Kevin Ryan, Founder and CEO of AlleyCorp. Kevin is an influential leader in the New York tech scene, with success stories including companies like DoubleClick, Gilt, and Business Insider. He and Matt discuss betting on the internet in the ‘90s, surviving the dot-com burst, the importance of data, and what makes a successful founder. Don’t miss this value-packed episode!</p>
Starting out at Euro Disney in Paris
01:02 MIN
Moving on to smaller, faster moving businesses
01:33 MIN
Moving on to smaller, faster moving businesses
01:33 MIN
Looking for businesses investing in the internet in the 90s
02:00 MIN
Joining DoubleClick
01:50 MIN
Fundraising and surviving the dot-com bust in the 2000s
03:24 MIN
Rebounding and eventually being acquired by Google
01:35 MIN
Starting up AlleyCorp
02:37 MIN
Success with Glit and Business Insider
03:03 MIN
Mongo's success
02:12 MIN
The scope of AlleyCorp today
01:48 MIN
What Kevin looks for in a founder
01:42 MIN
Training future leaders and CEOs
01:19 MIN
The continually evolving tech scene in New York City
04:26 MIN
Kevin's most exciting prospects on the horizon
01:20 MIN

Intro: Welcome to the Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with my friend Kevin Ryan. Kevin is founder and CEO of AlleyCorp, and by extension, founder or co- founder of a large number of some of the most storied and iconic internet brands in the history of the internet in New York City, companies like MongoDB, and Gilt Groupe, and Insider. Kevin, of course was the CEO of DoubleClick, the company that really sort of gave birth to the New York Tech scene in a lot of ways, or at least the ad tech internet scene. So Kevin, great to have you here.

Kevin Ryan: Very happy to be here.

Matt Blumberg: So I've been looking forward to this one because I love doing these Friday interviews where I get to sort walk through someone's career with them, and yours has been so fascinating, and it's been a pleasure to kind of have a view into it since you and I first met, I think, what did we just decide? In 1996?

Kevin Ryan: Yeah, yeah. Long time ago.

Matt Blumberg: Yeah.

Kevin Ryan: Probably'97.

Kevin Ryan: Probably'97.

Matt Blumberg: It

Matt Blumberg: was right after you started as CFO at DoubleClick.

Kevin Ryan: Yeah.

Matt Blumberg: So I'd love to start actually, very quickly, pre- DoubleClick. So I remember you were at United Media for a little while, right? Sort of dawn of the internet, and you were a management consultant before that?

Kevin Ryan: No, before that I worked for... after business school I worked for two or three years at Disney, at the opening of Euro Disney in Paris, because I went to INSEAD for business school, stayed in Paris for three years, then came back to New York to work at United Media for two or three years. Previous to business school, I was investment banker in New York and London for four years.

Matt Blumberg: So what did you work on at Euro Disney? Like the actual opening and launch?

Kevin Ryan: Yeah... No, I was there a year before the launch, and I was actually working on the Disney MGM studios, which was a park that had not yet opened, so that was going to open, and it did open several years later. So I was in finance, I was making my transition from investment banking into operations, and so I was in finance for about a year working on that, and then moved over into hotel operations and finance, so really helping... We had 15,000 hotel rooms, so it's like a city, and helping to figure out how we needed to run those better.

Matt Blumberg: So equally interesting to online media, but quite different. How did you transition from one to the other when you moved back to the US?

Kevin Ryan: So the only job, actually in my entire life, that I didn't really like that much was working at Disney. It was very big, it was very bureaucratic, and so it wasn't... slow- moving, it wasn't that fun. I wanted something smaller, and randomly, through a friend of mine, found out about a CFO- COO job of 180 person division of E. W. Scripps, which was a media company. Scripps owned newspapers and TV stations, and things like that, and there's a special division that wasn't doing well so they needed a CFO-COO, and most people didn't want to do it because the company was not doing that well, but I didn't care. For me, that was a huge job, I was managing about 60 people, and we ended up turning it around. Originally the plan was to sell it, but then the parent company said, " Keep it and grow it," because we're doing so well, and part of the growth strategy was I started an internet site in'95, which was very, very early.

Matt Blumberg: The Dilbert site.

Kevin Ryan: The Dilbert site, and it became very, very successful relative to sites at that time. We had advertising, we had e- commerce, we had to do it all ourselves because there were no tools. So at the beginning of'96, that led to my entire 25- year career after that because I became convinced, which now doesn't look like a genius move, that the internet was going to be a big, big industry. Someday everyone would be on the internet and have an email address, and buy things, and date, and do whatever, and so I wanted to leave and go start or join an internet company.

Matt Blumberg: But you're right, it was not an obvious decision. I remember my first project at Moviefone, which was right around the same time, it was in'95, was to answer the question of whether or not we should build a website. In the rearview mirror some things seemed more obvious than they were at the time.

Kevin Ryan: Actually, part of the reason I left was I went to the parent company as a loyal corporate citizen and said, " Look, this internet thing is going to be big. We have a headstart. You should give me$ 2 million and I'll build up an internet division, and I think it's a really good idea," and they said no. One of the things they asked me, which has not stood the test of time, is they said, " We don't know if we want to invest in this internet. We may wait for the next one," and I was like, " You have no idea what you're talking about. There's no next internet coming, so I think I need to leave you. You're part of my problem, not part of my solution." So I started talking to companies in Silicon Valley, and in New York.

Matt Blumberg: Actually, it's funny, I didn't realize you were talking on both coasts. What kept you in New York instead of moving out to the Golden State?

Kevin Ryan: Well, I really always preferred large cities. I had been living... I lived in Paris, London, and New York in the previous 10 years, and so that's where I want to be. I thought there was a chance, I just wasn't going to be able to stay in New York because at the time there was very close to zero happening here, there's probably 50 people working in the internet at that time. But I ran across DoubleClick, which was probably 10, 15 people, and two brilliant guys who had started it, and I ended up joining them, and was able to stay in New York, but I had offers to join Excite, which was early stage search engine, and some other things out on the West Coast as well.

Matt Blumberg: Yeah, that's right. There was very little tech in New York, not just internet, there wasn't a ton of software in New York.

Kevin Ryan: No. We couldn't even find a lawyer in New York to take us public because no companies had gone public in New York, so the whole public team was out in the Bay Area for almost every single law firm at the time.

Matt Blumberg: Yeah. So you joined DoubleClick in what year? In'99 or '98?

Kevin Ryan: No, June'96.

Matt Blumberg: '96, okay. So you wereCFO at first, you got promoted to president, got promoted to CEO, you were CEO when the company went public.

Kevin Ryan: No, I was still president when the company went public.

Matt Blumberg: So talk a little bit about the heyday, the ride up and the IPO, because today it's so far in the rearview mirror now, but for those of us who live through it's probably still quite vivid, that time is very vivid for me, like you and I both managed some employees who are under 30 or under 25, it's like ancient history for them.

Kevin Ryan: It was incredible because in'94, '95, we didn't even know the word internet, it didn't even exist, and to think that a couple years later, in'98, 24 months after DoubleClick started, we took the company public, it was worth$ 350 million, which at the time seemed enormous. Don't forget, Apple went public and raised$ 9 million at their IPO, so at the time, this seemed like a very big IPO, and then two years after we went public at a$ 300 million valuation, we were worth$ 12 billion. So the bubble had hit, we were growing like crazy, we did$ 500 million in revenue after four years, and everything was going well. You couldn't imagine it'd be going better, it felt like someone had... you were just in a dream world, all your employees were happy, your investors thought you were the smartest thing they'd ever seen, everything was working. We moved into our new office, and I remember we closed$ 12 million worth of business that day via our telemarketers, we were selling ads. It was like just there were gold coins everywhere until there weren't.

Matt Blumberg: Until there weren't. I remember distinctly one of the things you told me sort of post- IPO, was that one of the smartest things that you did was sort of time the capital markets right around, not your IPO raise, but the secondary raise.

Kevin Ryan: Yeah. So in the beginning of 2000, I was actually skiing in Europe, and the value of DoubleClick went up by a billion dollars during the week, on no news, and I remember thinking, " This feels very rich." I mean, because there's no news, a billion dollars is real money. My father worked for Caterpillar for 20 years, and we were almost as valuable as Caterpillar, which just didn't seem to make sense, so I thought we should go out and raise... do a big secondary and have cash, because worst case is, if we end up being worth 30 billion, no one's going to fire me for having raised money because we're worth 30 billion, but if things go down, which I think is possible, this will be really helpful. So we went out, and it was very difficult, we were trying to raise a billion dollars, had problems, only raised$ 800 million, but that$ 800 million in a way saved the company, not just because we had the cash, but when you are choosing between us and another company that had 10 million in the bank, and you're making a five- year commitment, where are you going to go? Especially given that four of our competitors just went bankrupt last week, and the guy who's making a decision who's like, " You got fired because why did you choose a bankrupt vendor?" We were the safe, safe choice, and we had the most engineers, and the most market share, and we're actually a good choice.

Matt Blumberg: Yeah, and obviously that more than a rainy day fund.

Kevin Ryan: Yeah, and we needed a lot of it because during two and a half years, 70% of our clients went bankrupt. That's not helpful, in case you're wondering.

Matt Blumberg: No, and that's the thing I always tell people that was different about the dot- com bust or whatever you call it, and a recession today. It's that all of your customers, all of my customers, they were just gone.

Kevin Ryan: Gone.

Matt Blumberg: Overnight.

Kevin Ryan: And not only were they gone, but they obviously didn't pay you the last three months that they owed you that they told you was coming, but it was never coming, so you ate a lot of that, in addition to losing the revenues going forward.

Matt Blumberg: Yeah.

Kevin Ryan: So we did seven rounds of layoffs. We had 2000 employees, and then... We didn't know, I mean, we didn't know how long it was going to last, and inaudible should do one round of layoff, but we just had no idea so it just kept going and going and going. So then, contrary to my earlier point, all your shareholders think you're an idiot, your employees suspect you're probably an idiot, every decision you made in the previous year looks terrible. I signed a lease to be able to fit 2000 people, a 12- year lease, and then I had to get out of it. Real estate prices collapsed. I had to write a check for$ 80 million to get out of that lease, cash, that would've bankrupted any normal company. But it was actually better because it saved me 10 million a year in rent for 10 years in a row, and you took the value back, and it just made more sense, but brutal. Brutal. I mean, people I had personally recruited, and convinced to leave their job making 300,000 to come make 150, 000 for me, and then five months later we fired them, and there were no jobs, there's no chance that person's going to get a job anytime soon, you don't feel good about that.

Matt Blumberg: No, you don't. So what are some lessons you took from that? There are obviously a lot of lessons you take on the way up, but what are some lessons that you took from that sort of awful period from late 2000 into 2002?

Kevin Ryan: Well, one thing, by the way, on the positive side, the reason DoubleClick today is still, and this is literally 25 years later, the dominant player in ad technology in the world, is because we move faster than everyone else between'96 and 2000. DoubleClick has never given that position up. It's like being on the risk board, you take all the countries and then you can protect them. So we had to pay a price for that, but long- term, I don't know what DoubleClick is worth today, but it's probably 50 billion, a 100 billion or some large number because of that, so no pain, no gain. You, obviously in retrospect, wish you had not been as aggressive, not made some acquisitions, not taking as much real estate, but you also never know. There were companies in'96 who were like, " Oh, no, this is a bubble, we're going to stay out of it and not expand," and we ate their lunch for two years, ended up 10 times larger, 10 times better brand, and then cut a lot of people and survived, and sometimes they went out of business.

Matt Blumberg: Yeah, and so I should say this, it's a little silly saying it to you, but for some of the people listening, so when you say DoubleClick is big today, and it's the standard today, and it's worth$ 50 billion, DoubleClick is part of Google.

Kevin Ryan: Yes, they bought it for about$ 3 billion in 2007, 2008. So this is a theoretical valuation, but it's a very important acquisition for Google, and an important part of their company.

Matt Blumberg: Yeah, for sure. So let's talk about the origins of AlleyCorp. So you wrapped up your time at DoubleClick, I can't remember if you did something in between the two or if you sort of helped start a business or two, and then it became AlleyCorp.

Kevin Ryan: We could debate when officially AlleyCorp started, but basically right in the beginning, Dwight, who was the CTO and co- founder of DoubleClick, and I had ideas for companies, and so we started companies, and we started a number of them. We started Mongo, we started Business Insider, we started Gilt, and we started one called ShopWiki, which we sold, it didn't do that well. We started one called Panther Express, it didn't do that great, lost money on it. But overall, we created three very, very, very successful companies during that period of time, and we spent a lot of our time in the next five years building them up. Dwight is still on the board of Mongo, and I was on the board for 12 or 13 years.

Matt Blumberg: It's funny when conventional wisdom is you can't do that, conventional wisdom is start a company, focus on one thing, you're not a portfolio as a CEO. How did you, or even the two of you work through so many different things, Insider Group, and... Insider, Gilt, and Mongo couldn't be more different, all three of them.

Kevin Ryan: And all different from DoubleClick. Yeah, no, there was actually a Harvard Business School case that was written, and it's unusual inaudible about me, and the thesis was what has happened here are all the things we teach at Harvard Business School that you can't do, but they seem to be working. So what does that tell us? There was no answer there. I think we just did the things we wanted to do, and managed to have a number of successes, and then have had successes since then. I've had a lot of successes in healthcare, new areas, and so I think if you can focus on do you have a good idea and do you have a great team, that there's some pattern recognition. I think what I do is what original VC was. Today, VC is often very late stage, it's almost private equity. You write them a$ 25 million check, they already have a business, and you try and add a little bit of value. We are really putting teams together, helping them, working with them, helping them recruit, helping them get customers, doing that work, that hard work, and I think, on average, we've shown that you can do this. AlleyCorp, over 10, 12 years has had well over a 50% IRR on hundreds of millions of dollars invested, and so that's comparable or better than the top, top, top VC firms in the entire country.

Matt Blumberg: So let's dig into the three first big successes, and I'm just curious, what made them succeed. What made Insider succeed? Let's start with that one.

Kevin Ryan: Yeah. The most interesting thing of the three was that if I saw you two years after they all started, because they started the same year, I would've told you that Gilt just did 175 million in its second year, which is insane. I don't think any business in New York City has ever done that, still to this day. Business Insider was doing about a million dollars, so okay, but obviously not the same. Then Mongo did zero, and then the next year did zero, and you and I would not have guessed that the zero was going to be worth$ 30 billion someday, and that the Gilt Company was going to be the least valuable out of the three, we sold it for 250 million. We sold Business Insider for about 450 million. But the simple premise for Business Insider was that there was no business site that I wanted to read at the time, and that no business site was adapted to the fact that you could check your email every day, every minute. The Wall Street Journal and Businessweek did not update their websites during the day, which people now can't even imagine that was true, but they were still on the schedule of, " We publish in the morning." Everyone publishes their story late at night and it comes out in the morning, and that's just how we roll, and we publish during the day. The second thing we did was have punchy headlines like, " They just made a bad acquisition." You'd never have that sort of editorial point of view in a Wall Street Journal article or Businessweek. The article would say, " They paid X, some people think it was too much, some people think it was the right amount, time will tell." Ours was more interesting, and most of the internet, not because of us, but we were one of the early players that did that, and it's punchier and more opinionated, more fun, shorter, and there was room for that.

Matt Blumberg: Yeah. So that's a business that I would say was driven by internet norms, right?

Kevin Ryan: Yes.

Matt Blumberg: Would you say the same about Gilt in a different way?

Kevin Ryan: Yeah, Gilt was a different thing. I saw this business model in France that no one knew about, which is essentially the Gilt business model. It's a company called Vente-Privee, and they were just selling fashion at a discount every day, and it was countered to the internet norm. Internet norm is that everything's available all the time, unlimited selection, and we had limited selection only available for a little bit of time, but at a big discount, and that scratched an itch. I started that business partly because I walked by on 18th street a sample sale, which I never went to, but mostly women, but there were 200 women waiting in line to get, I don't know, Marc Jacobs at 50% off, and I remember thinking, " I bet there's thousands of women in Philadelphia, and all these other places that don't have access to this." Not to mention there are people sitting in their office at Goldman Sachs who secretly would like to be in this line, but they actually have a job, and if I could bring that to them... We had moments where we had a 100,000 people in line waiting to shop, that shows you that there was room for this.

Matt Blumberg: Yeah. All right. Now let's go to Mongo, again, completely different business. I guess you could also say created by the internet or the need was spotted, but super deep technical business.

Kevin Ryan: Yeah. Well, one, I'm not deeply technical, but I had two co- founders who were incredibly brilliant, Dwight, and then Elliot Horowitz, who was the young most brilliant engineer. We had a inaudible out of 500 engineers, it was like up and coming LeBron James at age 19, and so could not have done it without them. But here's what we knew at the time, two big points. One is that data was changing. Data was all rows and column, structured data in 2007, and over time, we were going to have video and facial recognition, and things like that, and all that stuff needed to be stored, it was basically unstructured data. So the databases at the time were not the right databases technically for that. Secondly, that it needed to be open source, and then three, that the existing players, like Oracle, were very big and very expensive, they had 40% profit margins, and congrats to them, but that means there's an opening for a less expensive, easier to use open source database, and that's what we created, and today it does 2 billion in revenue. We'll be a$ 50 billion company, I think, at some point.

Matt Blumberg: Yeah. I mean, all three of them are remarkable, and what's most remarkable is how different they are, and that you started them all at the same time.

Kevin Ryan: One of the things that's validating about Business Insider is there are moments where BuzzFeed was more valuable. I think Business Insider may, today, be the most valuable online media company started during that whole era, more so than the Huffington Post, which is more or less disappeared, more than Vice, which went bankrupt, more than BuzzFeed, because it was sustainable and has a... today, has a thousand employees and$ 300 million in revenue. We sold it nine years ago, but it's extraordinary success.

Matt Blumberg: Yeah, and it really has been lasting, and it's probably overwhelmed its parent company at this point.

Kevin Ryan: Yeah.

Matt Blumberg: So you built on the success of those three, AlleyCorp today is a large organization, it's not you and Dwight creating a few businesses.

Kevin Ryan: No. No.

Matt Blumberg: What's the scope of it today?

Kevin Ryan: So we have 24 people here, mostly on the investment side, so bigger than most teams in New York. We start eight companies a year, roughly. We invest in probably 20 new companies. We have an overall portfolio of about 130 companies. We invest 75 to a $ 100 million dollars per year into those two buckets, and whether we started or invested in it, we're doing mostly early stage, and we're building these companies up. So I started Zola, which does hundreds of millions of dollars of revenue, Nomad Health also doing hundreds of millions of dollars of revenue. An investor in Ualá, which is a mobile bank in Argentina, which is worth 2 billion. Blueground, which is worth probably close to a billion. So just helping these companies grow over time, it takes five to 10 years. Now we have big specialized practices, 40% of what I do is in healthcare, 40% is in diversified tech, 10% in robotics, and 10% in social impact, so very specialized people. I also have resources that no one else has. I have a 65- person engineering team. My own in- house outsourced engineering company, engineers that are either in Columbia or in Montreal, so I can build up a tech infrastructure and team very quickly. I have a 10- person executive search firm called Soul Search that we co- own with Michelle Garland, who's the senior partner there, to look for healthcare executives. I have Digital Health New York, which I started, which is the largest digital health conference in New York. All those things are strategic assets that help us build, promote our companies, and so that's what we're doing.

Matt Blumberg: What do you look for in a founder? You're starting eight companies a year, you've got to find eight founders a year.

Kevin Ryan: Look, you're looking for passion. You're looking for competence. Sometimes they really know the sector very well, sometimes they're coming in from outside and have that perspective, it's okay. They need to be a good manager, that's essential to our industry because we have 1% unemployment in tech, and so no one's going to go work for someone who's an asshole, so I need to know that they can recruit, and they can keep and maintain, and motivate a team. They don't need to be the specialist in any one thing generally because they're the CEO, but they need to be able to handle a head of sales, a head of finance, a head of marketing, a head of HR, all those things, and make them feel good about it. But you don't always get it right either, it's an imprecise science, but yeah, in general, I feel pretty happy with a lot. I mean, Henry Blodget, 15 years later, he was one of seven people I interviewed for that job, 15 years later was still the CEO of Business Insider, and scaled from having, I think he had never managed two people before, or very few to a thousand people. Great to see.

Matt Blumberg: Yeah, I mean, it is one of the things. I don't know if you keep count of this, but I just, off the top of my head, can think of a dozen people who worked at DoubleClick over the years who went on to be CEO EO of something else, and it's probably dozens.

Kevin Ryan: Oh, yeah. When we found, once we added up, and we found 32 people who had become CEOs, sometimes small, but sometimes very large, David Rosenblatt is running 1stdibs, a publicly traded company, but many, many, many examples of that, and so great to see.

Matt Blumberg: Do you feel like they take, I mean, you're still in touch with a bunch of them, is there a leadership blueprint or playbook, or something that you feel like DoubleClick trained to?

Kevin Ryan: Not specifically. I think it's more that they were in an environment where they saw success. Look, we also, we had a choice of our people, as you said earlier. For several years, DoubleClick was the hottest company, and the most valuable in New York, so we got our choice, and did, I think, a good job of recruiting many, many talented people to come join that, and then they watched it. They worked with other talented people, they saw good things and bad things, and they thought, " You know what? I can do that too." They had relationships, they had a resume, so they walked in and said, " Yeah, I worked at DoubleClick for several years." We helped each other a lot. I mean, I've done 30 reference calls for DoubleClick people over the years, " Yes, you should hire him. Yes, you should invest in him." I still do today. The entire Gilt senior management team, sorry, Zola team all worked at Gilt. SecurityScorecard, a billion dollar security company in New York was my head of security at Gilt, I'm an investor in that. We're all helping each other and encouraging them, and that's what's so amazing about New York, is you're just watching that ecosystem grow and grow and grow through first, second, third generation.

Matt Blumberg: Yeah, it is amazing. I know one of the things you do, you're the vice chair of Tech NYC. When you think about the New York Tech scene, not just looking backwards and how much it's grown over the last 25 years, but if you think about the next 25 years, what does it look like? How does it start to grow from here? It's already sort of, " Okay, it's the number two," and then there are a bunch of number threes, but how do you think about some-

Kevin Ryan: It unquestionably, unquestionably becomes the number one tech city, that will happen. We are just watching industries create. I always remind people that only five years ago today you might've said to me, " Kevin, there's not a single publicly traded startup, tech startup in New York that's worth more than 3 billion," and that was true, and you can't name a single enterprise software company started in New York that is public, and that was true just five years ago. Today, the two most valuable companies created in the last 30 years here are Datadog and MongoDB, the only two that are roughly 30 billion or above, so getting some real scale and will continue to grow. They will, over time, spin out a hundred people, and you know what they're going to do? They're going to start enterprise software companies, and you know where they're going to start them? In New York City. You and I lived through a period in the 90s where companies moved from New York to San Francisco if they wanted to be successful. No chance that's happening today, all the VC firms in California are opening offices in New York because they know the talent is here. Look, every country I'm in I say, " I know where your tech center is going to be, just tell me where the top 20 universities in your country, where those grads want to live, and that's where it's going to be." Because our industry is driven by the smartest people often, but not necessarily from the best universities. In Germany, that's Berlin. They could have gone to Frankfurt, but you know what? They didn't want to live in Frankfurt, and so Berlin is the capital, and 20 years ago, no one would've imagined that. The classes from top places, they go to New York. We also have benefited from the fact that, which wasn't the case in 1990, that New York is more livable than it was then. Murder rate is down 85% since 1990, whereas San Francisco and other places are worse off, from a quality of life, that we got lucky on, but yeah, New York is going to continue to do well.

Matt Blumberg: Yeah. One of the things that's great about New York, and obviously I've made my whole career here as well, is that there's a real center of gravity. Even though there's a lot more stuff in Brooklyn now than there was 10 years ago or 15 years ago, the distance from Flatiron to Brooklyn is not like the distance from Cupertino to San Francisco.

Kevin Ryan: No, it's like four miles. I mean, it's literally nothing. It's four subway stops.

Matt Blumberg: Yeah. What role do you think Cornell Tech has played in this?

Kevin Ryan: So I was part of the selection committee to choose Cornell over the other ones at the time, so I was slightly involved with that, but it's played a small role. In fact, I'm incredibly happy with what they've done. They're now close to a thousand graduates per year coming out of Cornell that are master students in a variety of technical subjects. That's fantastic. But we also have 350, 000 people in the city who are working in technology, so it's not single- handedly moving it, but it's contributing to it. I said this at the time, we could actually use five more Cornells, and still have room here, it's a big, big ecosystem. But I'm so happy, and I think they've done an amazing job in being more innovative than Columbia or NYU, and more aggressive because they were the challenger coming in here.

Matt Blumberg: Yeah. No, that's right, and they definitely, they start companies there.

Kevin Ryan: Oh, yeah.

Matt Blumberg: Graduates are starting a lot of companies.

Kevin Ryan: They're just bolder and more commercial in some ways. They're not afraid that someone's starting a company. They don't wake up and think everyone there is going to get a PhD and teach because they're just not, and it's not true elsewhere. So where Cornell, and Dartmouth, and even Yale to a certain extent, suffer because they're not in a big city, and it's great undergraduate, but when people are 28 and getting their Masters, they're thinking, " I kind of like to be in a big city where I can date, and play on a tennis league, and go to museums, and go to clubs, and go to the best restaurants."

Matt Blumberg: Yeah. All right, so last question for you. What are you most excited about right now when you look at your portfolio, and you just went through the sectors you're investing in, which are pretty far- flung, robotics and healthcare, what gets you most excited right now?

Kevin Ryan: So two things, very different. One, is I've been very deep in psychedelics for mental health, so we've started a company called Transcend. I'm the leading funder of the Yale Center for Psychedelic Research, that's nonprofit research, but we've already raised$ 40 million for this company after two years, and we're taking a compound methylone through the FDA process, and the results are extraordinary so far. I have three other investments in psychedelic companies, and I'm very, very happy with the results, and what's happening across the country, at the national level and the state level there. Then secondly, pockets of AI. We're looking at something we haven't announced yet, of starting a industry focused LLM, and these are huge big swings that are super interesting to do there. So those are two things I'm pretty excited about, but yeah, what we do, what you and I have been doing for many years just remains incredibly fun, that challenge of building a team, competing with other things, doing something new, if it were easy would've already been done, and once in a while, it works really well and everyone's happy.

Matt Blumberg: All right, we'll leave it on that note. Kevin Ryan from AlleyCorp, thank you so much for spending time with me.

Kevin Ryan: Thanks for having me.


Tune in to this deep dive episode as Matt interviews Kevin Ryan, Founder and CEO of AlleyCorp. Kevin is an influential leader in the New York tech scene, with success stories including companies like DoubleClick, Gilt, and Business Insider. He and Matt discuss betting on the internet in the ‘90s, surviving the dot-com burst, the importance of data, and what makes a successful founder. Don’t miss this value-packed episode!