Inspired with Alexa von Tobel
00:00:44 · Alexa von Tobel, Alexa von Tobel
[00:00:44] S1: Welcome to Inspired. I'm Alexa von Tobel. I'm joined by the godfather of New York City tech and also a dear friend, Kevin Ryan. He's someone who scaled DoubleClick from 10 people to 2,000 employees in just four years and sold it to Google for 3,100,000,000. He then went on to build MongoDB, now worth 30,000,000,000. Business Insider, he also built, which sold for 450,000,000, as well as starting companies like Gilt Group, Zola, Pearl Health, Transcend Therapeutics, and many more. So that's Kevin Ryan, founder and CEO of AlleyCorp. For thirty years, Kevin has had one superpower, spotting the future before anyone else sees it and moving faster than the competition can react. In this conversation, we're gonna dig into how he identifies breakthrough opportunities across completely different industries, why he believes AI will transform work faster than we think, and the truth about what it actually takes to win from hiring top talent to knowing when to move at breakneck speeds. I've known Kevin for over twenty years, and I [00:01:37] S2: can tell you that this is [00:01:38] S1: a masterclass in execution and in building what's next. So let's dive right in. If you're running a startup, we know things like managing equity communicating with investors are always top of mind. Carta has built a connected suite of tools that over 40,000 companies use to do just that. Their platform of software and services helps you lay the groundwork so you can focus on building. To learn more or get started, visit carta.com.
00:01:38 · Alexa von Tobel, Alexa von Tobel
[00:01:38] S1: a masterclass in execution and in building what's next. So let's dive right in. If you're running a startup, we know things like managing equity communicating with investors are always top of mind. Carta has built a connected suite of tools that over 40,000 companies use to do just that. Their platform of software and services helps you lay the groundwork so you can focus on building. To learn more or get started, visit carta.com. [00:02:05] S2: And with that, let's welcome Kevin. Kevin, first of all, dear friend, somebody who's advised me through a lot of my own technology moments, I'll say. I'm so excited to have you on today, and I know we're gonna talk a lot about New York City Tech and the thirtieth anniversary and all these other great things. But I wanna start with your childhood as somebody who's such a prolific entrepreneur. You have an interesting mix. You and I actually have something in common, which I don't think we've ever connected on, which is you were born in Milwaukee, spent some time in Switzerland and Italy, settled in Ohio for high school. I also joke that I'm a mutt. My mom was from Indiana. My daughter's from Belgium, and that's how the family from Switzerland. I was born in Kentucky. You have, like, a very interesting world view because you literally were exposed to so many places early. I just wanted to start with one simple question, which is what do you think shaped you most in your childhood that kind of let you be somebody who's so confident and comfortable with risk? What would you say stood out?
00:03:14 · Kevin Ryan
[00:03:14] S0: Well, it's interesting because many entrepreneurs feel that they have this chip on their shoulder and they're overcoming something, and that drives them. And I don't have that at all. I grew up in an incredibly happy, balanced household. Parents were amazing. Great relationships with my siblings. Just from an early age, I was someone who was a sort of natural leader. School was easy. Sports was easy. So I felt like I cruised through life, got exposed to a lot of different things. It was really a a Midwest family. But because my father joined Caterpillar, we spent very key years from age five to about 13 in Europe, and that influenced, my perspective on the world, on new ideas, on thinking big. So I think that played a factor. And then by freshman year of high school, I was just... Felt compelled to go to, I hope, one of the best schools in the country. I didn't know anyone who'd ever been to Harvard, Yale, Princeton. Even as I got accepted, I still had never met anyone from those schools. But I thought Yale was the place I wanted to go and got an early decision. And, you know, I think that was another sort of upgrading of my life because I went to a very average high school and all of a sudden was was seeing the world's competition and the fact that everything was doable, that you you could be a senator or a CEO or a Nobel Prize winning academic. That was a legitimate thing. And so that... I think that was very helpful.
00:04:46 · Alexa von Tobel
[00:04:46] S2: I similarly feel like, you know, going to college was like a moment where you're like, wow. Look look at what the world can be. You are just a really prolific entrepreneur and have built some of the most influential companies the last twenty years. Forgive me while I take a minute and just name a few. I'm not gonna be able to name all of them because you've also touched so many startups, but we've got MongoDB now valued at $30,000,000,000. Business Insider, which I remember that one very intimately, was acquired from almost $450,000,000. Gilt Group, which is when I met you, which at one point reached a billion dollar valuation. We've got Zola, Pearl Health, Transcend Therapeutics. You've launched AlleyCorp, which is your venture fund that also incubates some companies, of which I've seen many of. And through all of that, you've been really intentional about New York City tech, which I love since I'm also here. When you think about what about you has helped you be in the right place at the right time doing so many of the right things, how would you reflect on that in a way that people can learn?
00:06:04 · Kevin Ryan, Alexa von Tobel
[00:06:04] S0: Well, look, some of it's luck. I mean, I joined a media company in 1994 and was CFO and COO of this 150 person division. And I read about the Internet, and I launched an Internet site. I just thought it could be super helpful for us. Very interesting. And, you know, the one great or lucky revelation I had by the beginning of '96 was that the Internet was going to change the world. It was gonna be the most fundamental trend in my lifetime, and that I wanted to go leave my relatively cushy successful corporate job and go start a company or join an early stage company. And so by doing that, and that became DoubleClick, And, you know, DoubleClick was a rocket ship, so I joined a company that had 10 people. Four years later, we had 2,000 employees in 25 countries. So crazy growth. We went public twenty four months after we started, which is just unthinkable today. And you have to, you know, get all the logistics in place, the accounting, everything. Goldman Sachs took us public. [00:07:08] S2: That is actually really wild, Kevin. Just... I mean, even like as we sit here and look at AI companies that are scaling from 0 to 200,000,000 of revenue in the same year to actually go public. I mean, that's crazy.
00:07:08 · Alexa von Tobel, Kevin Ryan
[00:07:08] S2: That is actually really wild, Kevin. Just... I mean, even like as we sit here and look at AI companies that are scaling from 0 to 200,000,000 of revenue in the same year to actually go public. I mean, that's crazy. [00:07:18] S0: Yeah. During those four years, we made at least 12 acquisitions. So, you know, just... So that... The success of that company trained me a lot. I had to adjust very quickly to that fast growth, making good decisions going forward, not having fear, and realizing that, you know, the reason today, double... DoubleClick, even though it's part of Google, is the most successful ad tech company or division in the world, which is now thirty years later, is because we won the first four years. Our competitors were in six countries. They weren't as big. They didn't expand as fast. They weren't as aggressive. They didn't take those chances. And in this case, it really worked. And so by being the best, by having the most engineers, by creating the best product, all the biggest customers wanted to work with us. And actually, we've never lost that position ever since. And that helped me be a mentor and founder of other companies, because one, had the credibility. People wanted to work with me because things I had done in the past. And I had managed a lot of people. I had fired a lot of people. I had seen so much during those nine years. I felt like I had forty years of of business compressed into those nine years.