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

Tim Ferriss (0:00)

Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers across all disciplines. My guest today comes from the world of business. Kevin Ryan, he is one of the leading entrepreneurs and investors in New York, which is an understatement, often called the godfather of New York City tech. He is the founder and CEO of AlleyCorp, a New York-based venture capital firm that incubates and invests across, catch this, healthcare, AI and software, consumer tech, deep tech and more. But investing is just part of it. He is also a co-founder of several notable companies, including MongoDB, Business Insider, Zola, Gilt Groupe and Transcend Therapeutics. What do those all have in common? They are completely different industries. Earlier in his career, Kevin was the CEO of DoubleClick, which he helped grow from a 20-person startup to a publicly traded company with more than 1,500 employees. We get into a lot here, so without further ado, please enjoy a very wide-ranging and tactical conversation with the one and only Kevin Ryan.

Kevin Ryan (1:03)

At this altitude, I can run flat out for a half mile before my hands start shaking.

Tim Ferriss (1:07)

Can I ask you a personal question? Kevin, thank you for making the time.

Kevin Ryan (1:27)

So nice to see you. Happy to be here.

Tim Ferriss (1:29)

So I wanted to just give people a scan, a 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 gonna 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 gonna come back to all of that. 1995, helps launch the blank website. I'm leaving that blank for a reason. We'll come back to it. And then after that, DoubleClick, that's where if people interview you, and I know you don't do very much media, but in the few that I've seen, that's where a lot of people start. We will not start there. Goes on DoubleClick sells for 1.1 billion. Ryan steps down, 2007, founds AlleyCorp. We're gonna spend a lot of time on AlleyCorp. Co-founds Gilt Groupe, Business Insider, TenGen later renamed to MongoDB.

Then co-founds Zola, a wedding registry company. And Nomad Health in 2015, a marketplace connecting clinicians with temporary health care jobs. I'm trying to give people an idea of the breadth of fields. 2015 Axel Springer requires control of Business Insider. I've got some numbers here, but who knows? 442 million, something like that. Hudson Bay buys Gilt Groupe, foreign 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. We will certainly talk about that. 2023 skis 101 kilometers to the South Pole.

So that stands out as an outlier. Then June, 2026, Otsuka completes its acquisition of Transcend, 700 million upfront plus up to 525 million contingent on future sales. July, 2026, announces AlleyCorp's 335 million. Second fund focused on backing companies at their earliest stages. I think you're doing a lot more deep tech investing also. This is a crazy bio, Kevin. There are so many reasons I wanted to chat and learn from you.

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. I've read that you sometimes do an exercise of listing trends on a whiteboard. Throw 20 trends up.

I'm going to read a bit. This is from foundersjourney.org. One exercise I do is to list 20 ideas on the board of trends that I believe are going to exist for 10 years. And then what are the implications that come out of that? And you can look at societal trends, healthy eating, automation and restaurants, gig economy. And this is where I think I missed steps. So first, I get the first part. You ask, if I bet that's going to continue for 20 years, the market is 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 like one or two years. But could you speak to that?