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

Tim opens by laying out Kevin Ryan’s unusually broad career: Yale economics, investment banking at Prudential, an MBA at INSEAD, Euro Disney, United Media, the Dilbert website, DoubleClick, and then AlleyCorp. Ryan later co-founded or backed companies including Gilt Groupe, Business Insider, MongoDB, Zola, Nomad Health, and Transcend Therapeutics. He also mentions Ryan’s South Pole expedition and his focus on companies spanning software, healthcare, AI, consumer technology, nuclear energy, and deep tech. Ryan says important companies generally take about 10 years to build, so he prefers trends that should persist for a decade rather than short-lived hype. He cites internet advertising as the trend behind DoubleClick, unstructured data as the trend behind MongoDB, psychedelics as a mental-health trend, and nuclear energy, the creator economy, and value-based care as other areas where AlleyCorp has invested. He says he has not yet found the right product in longevity, although he is studying the field through his DOC conference. His process begins by listing roughly 20 trends and asking both whether each will continue and what will exist in 10 years that does not exist today. He emphasizes that the second question is where he often finds opportunities. Ryan also looks for second-order beneficiaries: if Shopify grows, for example, which suppliers, infrastructure companies, or businesses shaped by changed consumer behavior will benefit?

Ryan describes four events he organizes: Deep Tech New York, focused on fundamental developments in areas such as materials science; Digital Health New York; DOC, focused on longevity and science; and the Odyssey, which is less commercial and brings together roughly 100 intelligent people for “intellectual nourishment.” He says these gatherings are not primarily direct business-generation exercises. His premise is that meeting fascinating people from different fields and creating conditions for good conversations will eventually produce useful relationships or ideas. He gives several examples of deliberately structured experiences. He is taking about 20 people to China to study what China does better, including venture-capital leaders and other people who can assess the country’s strengths firsthand. He has taken 16 off-piste skiers to Val d’Isère, plans a 30-person hiking trip in Switzerland, and runs an annual eight-person cycling trip in which each participant leads a 20-minute discussion over a meal. For a 30-person hiking trip, Ryan expects four- or five-hour morning hikes, afternoon sessions on subjects such as climate change, nuclear energy, or consciousness, and dinners that consolidate the conversations. He uses assigned seating for the first two nights so people mix across backgrounds, then leaves the final night unstructured so attendees can spend more time with people they particularly connected with. Tim compares this with small, assigned discussion tables from the early days of the Dialogue conference.

Ryan explains that Gilt Groupe adapted the French flash-sale model of Vente-Privée for the United States. The company offered high-end branded merchandise at a particular time each day, effectively giving people outside New York access to the kind of sample sales that were otherwise concentrated in New York fashion circles. Gilt reached $175 million in revenue in its second year and about $500 million in revenue in its fourth year, despite the operational complexity of buying, packaging, shipping, and processing returns. The market later changed. When Gilt started, brands such as Marc Jacobs often had no direct websites and relied on department stores. By 2008 or 2009, brands began selling and discounting their own products online; Macy’s and other department stores improved their sites; and companies such as Farfetch competed for the same merchandise. Ryan says Gilt had filled a gap that was becoming commoditized. The central lesson was the importance of a moat. Gilt tried to become large enough to influence vendors, but it never became large enough. Ryan recalls telling the board that the company was a “falling knife” and arguing that it should be sold while it could still command a meaningful price. The company was worth about $1 billion at one point, but ultimately sold to Saks for $250 million; three years later, Saks offered to sell it back for $5 million. Ryan says the experience made him stop pursuing e-commerce because he could not identify a sufficiently important unresolved problem in the market.

Before becoming an internet entrepreneur, Ryan worked in finance and operations. At Euro Disney, he was exposed to a huge launch involving 15,000 hotel rooms and about 50,000 visitors per day. At United Media, he became CFO and COO of a 180-person division, managing roughly 50 people during a turnaround. He says these roles made him comfortable with numbers, operating details, and understanding a business at a fundamental level, but also convinced him that he did not want to spend his career at large companies. After reading a 1990s BusinessWeek article about the Internet, Ryan launched the Dilbert website in 1995 because United Media owned the intellectual property. The site attracted substantial traffic from technically sophisticated users who could access the early Internet without a browser. Ryan sold IBM the first advertising placement, inventing a price for a medium that had never existed, and added merchandise such as T-shirts and ties. When he asked the parent company for a few million dollars to build an internet division, an executive rejected the proposal, saying they would wait for “the next Internet.” Ryan says that moment showed him the organization was not his future. Ryan joined DoubleClick as roughly its tenth or twelfth employee, initially as CFO, then president, and ultimately CEO. He attributes the rapid promotion to acting like a founder, making decisions quickly, understanding the numbers, taking risks, and adapting to the speed of the new market. DoubleClick opened offices in 25 countries before its first country was profitable, while competitors were in about six countries. That global footprint helped it win major customers such as Microsoft and Procter & Gamble, after which smaller customers followed. Ryan says DoubleClick became the world leader and would be worth roughly $100 billion as an independent company today.

Ryan explains that AlleyCorp initially differed from a conventional accelerator. He and technical partner Dwight Merriman generally invested about $500,000 each, built the product for roughly a year, often launched it, and then raised outside venture capital. They started six companies in the 2005–2008 period; Gilt, Business Insider, and 10Gen—later MongoDB—became major successes. Merriman handled the technical side, while Ryan focused on the business, recruiting CEOs, fundraising, and operations. Ryan says both Gilt and Business Insider began narrowly and expanded only after proving demand. Gilt started with one women’s clothing sale per week, then added more sales and eventually men’s clothing, children’s products, travel, and home. Business Insider began with three people covering New York technology. It later added Wall Street and other verticals as the audience and staff grew, eventually reaching about 600 journalists, including six covering defense at the time of the sale. Business Insider’s original insight was that there was no major business-news site built natively for the Internet. Established publications such as The Wall Street Journal and BusinessWeek did not update continuously during the day. Business Insider published repeatedly, used punchy headlines, and tested several headlines for five minutes each before keeping the one that attracted more readers. Ryan says the company never bought marketing; its strategy was to create content good enough to reach 100 million unique visitors. He believes acquiring those readers was 90%–95% of the challenge, while selling advertising afterward was comparatively easy. For founders, Ryan says AlleyCorp’s credibility mattered: he and Merriman had just sold the most valuable New York startup of its time and could help new CEOs raise money. He does not start by targeting a particular venture firm or planning an exit. Instead, he focuses on whether the product is something people want and says the financing, hiring, and eventual outcome follow if that problem is solved.

When asked how he chooses what to build, Ryan says the early process was simply him and Merriman sitting in a conference room, brainstorming and sometimes going months without an idea. He describes the signal as a “business crush”: an idea that he cannot stop thinking about. If the enthusiasm is still building after roughly two weeks, he usually proceeds rather than spending months on a detailed business model. For an early company, he wants a great product person first, not a finance or marketing executive. Ryan discusses AlleyCorp’s investment in Valar Atomics, a small-modular-nuclear-reactor company. His deep-tech team found the company about three years earlier, when it had a $20 million valuation. After raising from Sequoia at a publicly announced $6 billion valuation, it became an example of the scale of the opportunity Ryan sees in nuclear energy. He says government support for nuclear was not strong when they invested, but that the U.S. government has since moved nuclear and psychedelics forward substantially. He believes nuclear should be an important part of the energy future and points to France’s roughly 70% nuclear electricity generation as evidence that it can provide stable energy. Ryan says AlleyCorp has only sold part of a position once. Going forward, he thinks a smaller fund should consider selling roughly one-third of a position in rounds four or five, returning money to investors and teams while reducing risk. He is the largest LP, with mostly family offices and some institutions among roughly 40–50 LPs. He says the first fund and family office were around 60% IRR, and the $335 million second fund is in that ballpark, while emphasizing that the results have been unusually fortunate. He rejects the conventional goal of accumulating assets. Whereas large venture firms may emphasize the 2% management fee, he says AlleyCorp focuses on the 20% upside by building companies during their first five years. Funds may grow as the firm adds verticals, time horizons, or geographies, but not simply to collect more assets.

Ryan says Michael Pollan’s 2018 book How to Change Your Mind changed his view of psychedelics when he was 54. He began studying the research, learned about Yale’s work on PTSD, depression, and anxiety, and became a major donor to Yale’s Center for Psychedelic Research. In 2021, he concluded that a for-profit company was needed because moving one compound through the FDA process costs approximately $200 million to $250 million—more than philanthropy alone could support. Working with Yale professor Ben Malcom and AlleyCorp team member Blake Mandel, Ryan helped create Transcend Therapeutics around methylone. Ryan says methylone had potential advantages over MDMA: it could be administered weekly in their trials, appeared less likely to deplete serotonin, generally lacked the same post-treatment “downer,” and had a duration more compatible with ordinary healthcare. Transcend’s patent covers PTSD, depression, and anxiety, although the company initially had to focus on one indication because each additional indication requires substantial clinical spending. Ryan says the PTSD results were “incredible.” Tim and Ryan discuss lessons from earlier psychedelic companies. Long sessions lasting four to six hours can be difficult and expensive to scale, while bundling psychotherapy creates problems because the FDA has difficulty evaluating and standardizing therapy. Ryan says Transcend tried to learn from those mistakes. He also notes that PTSD affects many more women than commonly assumed; Transcend’s trials were about 60% women, and sexual assault is the largest source of PTSD, even though veterans receive much of the public attention. Transcend was established as a public-benefit corporation. The original shareholders committed 10% of their gains to a philanthropic effort, and Ryan says roughly $20 million will be distributed during the next nine months to psychedelic-related causes. The team is reviewing about 50 organizations and expects to make roughly 20 substantial grants rather than hundreds of small ones. Ryan is especially interested in lowering treatment costs, including testing whether group therapy could work as well as or better than individual treatment. He says the industry has made little progress in reaching the vast majority of people with depression or PTSD because treatment remains too expensive.

Ryan says AlleyCorp has increasingly focused on deep tech because energy, robotics, healthcare, space, and AI offer large, defensible opportunities that are less crowded than consumer products. He expects dramatically more robots within a decade—possibly 100 to 10,000 times more—and says the best initial applications are narrow, single-purpose tasks in factories, textiles, automotive production, and similar environments. General restaurant work is harder because it combines chopping vegetables, carrying garbage, and fetching supplies, tasks humans handle flexibly. He remains bullish on robotic massage, noting that the United States had roughly 17,000 unfilled massage jobs two years earlier. A robot could serve people who prefer privacy or who cannot find an available human therapist, and he estimates the technology is about 70% of the way to working. He also describes an AI customer-support agent that switched into Spanish after recognizing that a caller was struggling to explain a medical issue in English. Ryan sees opportunities in the second-order effects of large-scale deployment, including satellites, factories, and specialized services. Ryan says maintaining balance became necessary during DoubleClick’s intense growth. He prioritized family, fitness, and work, cutting other activities by about 80%. He took his children to school and made sure to spend four or five weeks on meaningful vacations with them. Now he spends eight to ten weeks away from the office each year, usually working two or three hours daily, although some days require a full shift. He also plays competitive table tennis every two or three weeks and credits coaching from Musa, an Olympic-level Nigerian player, with helping him improve. Asked what he would put on a billboard, Ryan calls for a more balanced, open, and caring United States. He worries about income inequality, declining upward mobility, poor schools, job losses from AI, and the country’s lack of preparation for retraining. He favors a more equitable tax system, reducing the budget deficit, expanding professional training beyond conventional college degrees, and accepting more highly skilled immigrants. He argues that immigrants have historically created companies and jobs, and that the United States should remain the place where the world’s best talent wants to build. He closes by saying New York is booming in restaurants, startups, sports, and technology, and that the United States remains exceptionally strong in future industries while needing to take China’s progress seriously.