#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 (alleycorp.com), 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.
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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
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