#884: How to Spot 10-Year Trends and Build Billion-Dollar Companies — Kevin Ryan of DoubleClick, MongoDB, Business Insider, and Many More
Episode of The Tim Ferriss Show · September 24, 2026 · 1 h 26 min
Tim Ferriss talks with investor Kevin Ryan about spotting 10-year trends, building DoubleClick, Gilt, Business Insider and MongoDB, psychedelic drug development, deep tech, and immigration.
Summary
Tim Ferriss interviewed Kevin Ryan, founder of the New York venture firm AlleyCorp and co-founder of companies including MongoDB, Business Insider, Gilt Groupe, Zola and Transcend Therapeutics. Ryan described his method of betting on trends he expects to last at least ten years, thinking through second-order effects, and recounted how he and colleagues foresaw falling bandwidth costs in 2003 but failed to start a YouTube-like company. He also described the curated gatherings and trips he organizes for learning and networking.
Ryan traced his career from finance and Euro Disney to United Media, where he launched the Dilbert website, then to DoubleClick, where he credited fast decision-making and rapid international expansion for its dominance. He explained AlleyCorp's early model of co-founding companies with Dwight Merriman, starting narrow and expanding, as with Gilt's single weekly sale and Business Insider's initial focus on New York tech. He discussed Gilt's decline as brands and department stores built their own e-commerce, his decision to sell, MongoDB's slow path to revenue, a failed 'Shopify for healthcare' venture, an early investment in nuclear company Valar Atomics, and his preference for keeping funds small.
Ryan explained how Michael Pollan's book How to Change Your Mind led him to fund the Yale Center for Psychedelic Research and co-found Transcend Therapeutics, which developed methylone for PTSD and was acquired by Otsuka. He described Transcend's public-benefit structure, under which initial shareholders committed 10% of gains to psychedelic causes. Ferriss and Ryan discussed robotics, robot massage and AI customer service, and Ryan closed by arguing for addressing income inequality, a more equitable tax system, expanded skilled immigration, and expressed strong optimism about New York.
Chapters
- 0:00
Introduction and Ryan's track record
Ferriss introduced Kevin Ryan and walked through a chronology of his career from Yale to AlleyCorp and the Transcend acquisition.
- 3:26
Spotting 10-year trends
Ryan explained why he bets on decade-long trends such as internet advertising, unstructured data, psychedelics, nuclear energy and value-based care.
- 6:31
Designing gatherings and trips
Ryan described his conferences and group trips and how he structures hikes, sessions and seating to foster conversation.
- 11:42
Second-order thinking and the missed YouTube
Ryan discussed second-order effects and recounted how his team foresaw cheap video bandwidth in 2003 but did not build YouTube.
- 16:54
Gilt Groupe's rise and sale
Ryan described Gilt's rapid growth, the erosion of its moat as brands went online, and his push to sell before further decline.
- 22:06
Early career, Dilbert and DoubleClick
Ryan recounted launching the Dilbert website, leaving United Media, and leading DoubleClick through fast global expansion.
- 27:53
AlleyCorp's model and Business Insider
Ryan explained co-founding companies with Dwight Merriman, starting narrow, recruiting founders like Henry Blodget, and growing Business Insider without marketing.
- 38:29
Choosing ideas, nuclear bets and fund strategy
Ryan discussed the 'business crush' test, the Valar Atomics investment, taking money off the table, and keeping funds small.
- 47:10
Ping-pong, family and vacation
Ryan described his table tennis coaching and how he prioritized family, fitness and long vacations.
- 51:51
Psychedelics and Transcend Therapeutics
Ryan explained his path to psychedelics, founding Transcend, choosing methylone for PTSD, and its public-benefit giving commitment.
- 1:05:43
Deep tech, robotics and AI
Ryan discussed AlleyCorp's shift toward deep tech, robotics in factories, robot massage, and AI customer support agents.
- 1:11:31
Failures, MongoDB and exits
Ryan described a failed healthcare software startup, MongoDB's slow road to IPO, and his approach to selling public shares.
- 1:15:03
Inequality, immigration and New York
Ryan argued for addressing income inequality and taxes, welcoming skilled immigrants, and expressed optimism about New York.
Key points
What was said, by whom, with the exact words. Timestamps jump to the moment.
- Kevin Ryan
Ryan argues that building an important company takes about ten years, so founders must bet on long-term trends.
“First of all, 10 years is important because to build an important company, unfortunately, you can't do it in two or three years”
- Kevin Ryan
Ryan recounts that in 2003 his team foresaw video serving costs falling below ad revenue but failed to start a YouTube-like company.
“we looked at the trend and thought, you know, by 2005, 2006, they're going to cross. And we should have started YouTube, and we didn't”
- Kevin Ryan
Ryan says he pushed Gilt's board to sell because the business was declining, ultimately getting $250 million.
“I said, we have a falling knife here. And so we went out and we only got $250 million”
- Kevin Ryan
Ryan says he has avoided e-commerce since Gilt because he views the problem as already solved.
“I can get anything delivered to my house in like 27 seconds. I can return it. It's inexpensive. So I don't know how to do better”
- Kevin Ryan
Ryan claims DoubleClick, if still independent, would be worth $100 billion.
“DoubleClick today, as an independent company, would be worth $100 billion”
- Kevin Ryan
Ryan says Business Insider deliberately never did marketing, betting on quality content to reach 100 million uniques.
“Our strategy was, we're never going to do marketing. So by the way, you've never seen an ad for Business Insider”
- Kevin Ryan
Ryan says he pursues an idea if his intellectual 'business crush' on it persists for about two weeks, without building a business model.
“And if that sticks with me for like two weeks, I generally do it”
- Kevin Ryan
Ryan credits the Trump administration with advancing nuclear energy and psychedelics despite otherwise not being a fan.
“I'm not always the biggest fan of the Trump administration, but on psychedelics and nuclear, I think they're right on both”
- Kevin Ryan
Ryan says small funds like AlleyCorp should sell about a third of a position in later rounds four or five years in.
“we think it's a good idea for a smaller fund like us in rounds four or five years in to sell a third of our position”
- Kevin Ryan
Ryan says AlleyCorp prefers small funds focused on returns rather than management fees.
“VC funds are typically 2% and 20% on the upside. Big funds focus on the 2%. We focus on the 20%”
- Kevin Ryan
Ryan says the high cost of FDA approval is why psychedelic development needed a for-profit company rather than philanthropy alone.
“it takes roughly $200 to $250 million to get one compound through the FDA process”
- Kevin Ryan
Ryan argues methylone has advantages over MDMA, including being safe to dose weekly in trials.
“you can take meth alone once a week in our trials. You actually can't take MDMA once a week”
- Tim Ferriss
Ferriss argues that bundling psychotherapy with MDMA, as Lykos did, hurt approval because the FDA could not evaluate standardized psychotherapy.
“the combining of psychotherapy right the bundling of psychotherapy and then you put it in front of the fda advisory committee”
- Kevin RyanPrediction · due Jun 2027
Ryan says Transcend's initial shareholders' foundation will give $20 million to psychedelic-related causes within nine months.
“so we will be giving 20 million dollars in the next nine months to causes linked to psychedelics”
- Kevin Ryan
Ryan says sexual assault is the leading source of PTSD, which is why Transcend's trials were 60% women.
“The number one source is sexual assault. And that's why our trials were actually 60% women”
- Kevin Ryan
Ryan says cost is the main barrier to psychedelic therapy and he wants to show group therapy works as well.
“One of the biggest challenges we have, it's too expensive. And one of the things I am interested in is trying to show that group therapy works as well”
- Kevin Ryan
Ryan predicts robots will see their biggest opportunity in single-use factory applications rather than varied tasks like restaurants.
“So single use is the best way, and factories are the best way for that. So that's going to be colossal in every single factory”
- Kevin Ryan
Ryan says robot massage is a solvable problem that is largely solved already.
“It is a solvable problem, and we're probably 70% of the way there to solving it”
- Kevin Ryan
Ryan attributes MongoDB's decade-long path to IPO partly to having no revenue for its first three and a half years.
“Because, first of all, we didn't have any revenue for three and a half years”
Linked moment · 1:16:06Skip to 1:16:06 using a listen link in the info box.
Kevin RyanRyan worries about income inequality and argues the U.S. is unprepared for job losses from AI.
“We can debate the time. We're going to lose jobs to AI. And I don't think we're in a good position to help people have successful lives”
Listen from 1:16:06 · Income inequality in the United States
- Kevin Ryan
Ryan argues for a more equitable tax system in which the wealthy pay 30% and for reducing the budget deficit.
“We're going to have to end up having a more equitable tax system where the wealthy pay 30% taxes, which they don't right now”
Listen from 1:16:34 · Income inequality in the United States
- Kevin Ryan
Ryan argues the U.S. should admit one to two million highly skilled immigrants while not allowing unlimited border crossings.
“And we shouldn't take 100 million of them, but we should take a million of them. Two million of them”
Listen from 1:18:43 · Illegal immigration to the United States
- Kevin Ryan
Ryan says New York is booming, with many people moving from Europe to start companies there.
“I see so many people moving from Europe, coming to New York, starting up companies”
People
In the conversation
- Tim FerrissAmerican author, podcaster and investor, host of The Tim Ferriss Show
- Kevin RyanAmerican entrepreneur and investor, founder and CEO of AlleyCorp and former CEO of DoubleClick
Discussed
- Dwight MerrimanTechnologist and co-founder of DoubleClick, MongoDB and AlleyCorp
- Henry BlodgetFormer Wall Street analyst and co-founder of Business Insider
- Michael PollanJournalist and author of How to Change Your Mind
- Benjamin KelmendyYale psychiatry researcher who worked with Ryan on Transcend Therapeutics
- John KrystalYale psychiatrist known for foundational ketamine research
- Blake MandelAlleyCorp alumnus who became CEO of Transcend Therapeutics
- Tobi LütkeCo-founder and CEO of Shopify
- Alexander ShulginChemist known for psychedelic research and popularizing MDMA
- Travis KalanickUber co-founder working on industrialized restaurant kitchens
- Donald TrumpPresident of the United States whose conduct of the Iran war is the episode's main subject
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From the publisher
Kevin Ryan is one of the leading entrepreneurs and investors in New York. Often called the “Godfather of NYC tech,” he is the founder and CEO of AlleyCorp , a New York based venture capital firm that incubates and invests across healthcare, AI and software, consumer tech, deep tech, and more. Kevin is also the co-founder of several notable companies including MongoDB, Business Insider, Zola, Gilt Groupe, and Transcend Therapeutics. 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. This episode is brought to you by: Eight Sleep Pod 6 which cools or heats each side of the bed, with custom elevation and snoring reduction, and wearable-free sleep tracking: EightSleep.com/tim Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: Shopify.com/Tim Momentous high-quality creatine for cognitive and muscular support: LiveMomentous.com/Tim AG1 all-in-one nutritional supplement: DrinkAG1.com/Tim Timestamps: 00:00:00 Intro from Tim 00:01:25 Kevin Ryan’s entrepreneurial track record 00:03:40 Spotting long-term trends and turning them into businesses 00:06:33 Designing gatherings and trips for great conversations 00:11:42 Second-order thinking and the missed YouTube opportunity 00:17:47 Gilt’s rise, shrinking moat, and knowing when to sell 00:22:06 From Dilbert to DoubleClick: early lessons and fast decisions 00:27:52 AlleyCorp’s model: start narrow, then scale 00:32:26 Recruiting founders and building Business Insider 00:38:28 Recognizing a business crush and choosing what to build 00:41:44 Investing in nuclear energy 00:43:26 Taking money off the table and keeping funds small 00:47:15 Ping-pong and the value of coaching 00:49:05 Making time for family, fitness, and vacation 00:51:52 Psychedelics and the origins of Transcend Therapeutics 00:54:20 Methylone, PTSD trials, and navigating the FDA 00:59:57 Transcend’s publi…
Summary, chapters and key points were generated from the episode transcript on October 3, 2026. Quotes are checked word for word against the transcript.