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: https://EightSleep.com/tim Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: https://Shopify.com/Tim Momentous high-quality creatine for cognitive and muscular support: https://LiveMomentous.com/Tim AG1 all-in-one nutritional supplement: https://DrinkAG1.com/Tim 00:00 Coming up. 00:25 The chronology, prepared by the robots. 02:40 20 trends on a whiteboard, 10 years out. 05:36 Four conferences, a China trip, and how to seat 30 people. 10:54 The YouTube Kevin didn't start. 13:45 Gilt: $500 million in year four, then a falling knife. 18:06 "We're going to wait for the next internet." 21:59 DoubleClick: 25 countries before one was profitable. 24:00 The AlleyCorp model: $500K each, a year to build, then raise. 28:31 Recruiting Henry Blodget in 30 minutes. 31:34 The two-week business crush. 34:55 Valar Atomics: $20 million to $6 billion in three years. 38:35 Why the fund stays small: 2% vs. 20%. 40:25 Ping pong, red wine, and Ibiza dance floors. 42:15 Three things only; everything else cut 80%. 45:05 The book that changed Kevin's mind at 54. 47:36 Methylone: MDMA's gentler, shorter cousin. 50:16 The second mouse gets the cheese. 53:13 A public benefit corp that actually pays out. 59:13 Is early-stage venture dead? 1:01:37 Robot massage and the AI agent that switched to Spanish. 1:05:13 The healthcare Shopify that failed; MongoDB's revenue-free years. 1:08:44 Kevin's billboard. 1:10:00 Pulling levers: taxes, training, and immigrants. 1:13:45 New York is booming. 1:15:24 Parting thoughts. Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded one billion downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/