Inspired with Alexa von Tobel
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.
00:07:18 · Kevin Ryan, Alexa von Tobel
[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. [00:08:30] S2: You said something that I think applies to the world that we're in right now, Kevin, which is that speed really mattered. [00:08:35] S0: Mhmm. [00:08:36] S2: You got bigger. You were more aggressive. You were faster. And I think as we fast forward to 2025, that's that same concept is still true. Mhmm. In a really important and powerful way.
00:08:36 · Alexa von Tobel, Alexa von Tobel
[00:08:36] S2: You got bigger. You were more aggressive. You were faster. And I think as we fast forward to 2025, that's that same concept is still true. Mhmm. In a really important and powerful way. [00:08:53] S1: What do you... What have [00:08:54] S2: you learned about doing speed properly? Because speed can also be chaotic. Any quick insights there?