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

Hello, boys and girls, ladies and germs. I’m sitting down with Kevin Ryan, the so-called Godfather of New York tech: DoubleClick, MongoDB, Business Insider, Gilt, Zola, healthcare, deep tech, psychedelics—the résumé is absurd. I wanted to start with how he looks ten years ahead, because that seems to sit underneath these very different bets.

Ten years matters because a meaningful company takes that long. If something is fashionable now and fades in two years, you’re probably late. I’ve been wrong plenty, but internet advertising, unstructured data, psychedelics, nuclear, creators, and value-based care were durable currents. Longevity interests me, but I don’t yet have the product idea, so I run a science conference to learn.

You also convene people constantly—deep tech, digital health, longevity, and a broader ideas gathering. Is that basically opportunity and talent scouting, with learning underneath it?

Some events relate to the business, but Odyssey is intellectual nourishment. Put fascinating people from different worlds together and good things tend to happen, commercial or otherwise. I assign seats for the first dinners so nobody only talks to usual friends. A few hours outside, smart sessions, and dinner is a pretty good formula.

That tracks with my Shopify decision: more people online, more commerce, more mobile phones—okay, somebody will win. But what are the traps when people extrapolate trends?

There’s no clean formula. I look for second-order effects: if Shopify wins, who supplies it, and how does behavior move? In 2003, bandwidth costs were falling. Video delivery was uneconomic until ad revenue could exceed serving costs; we recognized the crossover was coming and, regrettably, didn’t build YouTube. That was a very expensive missed implication.

Gilt was good news and bad news. French flash-sale sites showed me people outside New York wanted high-end sample-sale merchandise. We grew astonishingly fast, but brands built their own sites, department stores improved, and competitors crowded supply. We nearly had a moat, but weren’t big enough to matter to the biggest vendors. I pushed to sell while there was still value; waiting would have been worse. That left me less excited by e-commerce: buying, returning, and delivery are already remarkably good, while energy, cancer, and mental health still have huge things waiting to be built.

My early career gave me financial grounding, then operational experience launching Euro Disney at enormous scale. At United Media, I read about this thing called the internet—no browser yet—and thought, this is incredibly cool. We owned Dilbert, so I launched its site, sold a primitive IBM banner ad, and watched traffic explode. When the parent company wanted to wait for whatever came after the internet, I knew this wasn’t my future. I joined DoubleClick as roughly employee ten, became president, then CEO.

I learned to decide much faster. We opened in twenty-five countries before our first market made money. That looked crazy if it failed, but global customers wanted a global partner, and once large companies chose us, others followed. At AlleyCorp, Dwight Merriman handled the technical side brilliantly and I focused on company building, CEOs, and financing. We built and launched products before fundraising. Start narrow, do one thing well, then earn the right to expand.

An idea starts as a business crush. I can’t stop thinking about it; a week later, I’m imagining the product and people. If that lasts a couple of weeks, I usually move. I don’t begin with a spreadsheet, a planned exit, or which investor will say yes. Make a product people genuinely want; fundraising and hiring get much easier. Business Insider did that with evolving online business news, tested headlines, and strong journalists. Getting readers is nearly all the work.

We’re deliberately not trying to become an asset-gathering machine. The early years are where we add the most value. Deep tech, healthcare, software, and AI matter because the world is changing dramatically there. In robotics, the nearer opportunity is often one constrained factory task done extremely well, not a robot that runs an entire restaurant. MongoDB had no revenue for three and a half years—do not copy that. We gave it away, built trust in smaller uses, and eventually adoption accelerated.

Michael Pollan’s book changed my mind about psychedelics. I had assumed they weren’t useful, then saw research around PTSD, depression, and anxiety. Transcend became for-profit because moving a compound through regulators takes hundreds of millions. Methalone seemed promising—potentially gentler than MDMA, shorter, and more compatible with repeated clinical use—but you still need proper blinded trials. We made Transcend a public benefit corporation, with ten percent of gains for related causes. Access is far too expensive, and I’m interested in whether group treatment can lower cost.

If I could put up one message, it would be that we need a more caring society. I worry about inequality, weak upward mobility, poor schools, and job displacement from AI. We need a more equitable tax system, stronger training and retraining, and pathways for people to feel their children can do better. We also need talented immigrants. Borders need rules, but blocking highly trained AI and technical people makes no sense. America has always benefited from ambitious people arriving and working incredibly hard.

New York is absolutely on fire. Kevin, lovely to see you. For everybody listening, we’ll put the links in the show notes. Until next time, be a bit kinder than necessary—to other people and to yourself. Thanks for tuning in.