#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/timShopify global commerce platform, providing tools to start, grow, market, and manage a retail business: Shopify.com/TimMomentous high-quality creatine for cognitive and muscular support: LiveMomentous.com/TimAG1 all-in-one nutritional supplement: DrinkAG1.com/TimTimestamps:00:00:00 Intro from Tim00:01:25 Kevin Ryan’s entrepreneurial track record00:03:40 Spotting long-term trends and turning them into businesses00:06:33 Designing gatherings and trips for great conversations00:11:42 Second-order thinking and the missed YouTube opportunity00:17:47 Gilt’s rise, shrinking moat, and knowing when to sell00:22:06 From Dilbert to DoubleClick: early lessons and fast decisions00:27:52 AlleyCorp’s model: start narrow, then scale00:32:26 Recruiting founders and building Business Insider00:38:28 Recognizing a business crush and choosing what to build00:41:44 Investing in nuclear energy00:43:26 Taking money off the table and keeping funds small00:47:15 Ping-pong and the value of coaching00:49:05 Making time for family, fitness, and vacation00:51:52 Psychedelics and the origins of Transcend Therapeutics00:54:20 Methylone, PTSD trials, and navigating the FDA00:59:57 Transcend’s public-benefit mission and giving back01:05:46 Deep tech, robotics, and the next wave of opportunities01:11:35 Failed startups, MongoDB, and knowing when to persist01:15:06 A more caring society: inequality, taxes, and opportunity01:17:26 Immigration and attracting the world’s best talent01:20:04 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-sponsorsSign up for Tim’s email ne