#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.

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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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