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

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 public-benefit mission and giving back 01:05:46 Deep tech, robotics, and the next wave of opportunities 01:11:35 Failed startups, MongoDB, and knowing when to persist 01:15:06 A more caring society: inequality, taxes, and opportunity 01:17:26 Immigration and attracting the world’s best talent 01:20:04 Why Kevin is bullish on New York * For show notes and past guests on The Tim Ferriss Show , please visit tim.blog/podcast . For deals from sponsors of The Tim Ferriss Show , please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter ( 5-Bullet Friday ) at tim.blog/friday . For transcripts of episodes, go to tim.blog/transcripts . Discover Tim’s books: tim.blog/books . Follow Tim: Twitter : twitter.com/tferriss Instagram : instagram.com/timferriss YouTube : youtube.com/timferriss Facebook : facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .