podcast

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

24.09.2026
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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:

Intro from Tim

Kevin Ryan’s entrepreneurial track record

Spotting long-term trends and turning them into businesses

Designing gatherings and trips for great conversations

Second-order thinking and the missed YouTube opportunity

Gilt’s rise, shrinking moat, and knowing when to sell

From Dilbert to DoubleClick: early lessons and fast decisions

AlleyCorp’s model: start narrow, then scale

Recruiting founders and building Business Insider

Recognizing a business crush and choosing what to build

Investing in nuclear energy

Taking money off the table and keeping funds small

Ping-pong and the value of coaching

Making time for family, fitness, and vacation

Psychedelics and the origins of Transcend Therapeutics

Methylone, PTSD trials, and navigating the FDA

Transcend’s public-benefit mission and giving back

Deep tech, robotics, and the next wave of opportunities

Failed startups, MongoDB, and knowing when to persist

A more caring society: inequality, taxes, and opportunity

Immigration and attracting the world’s best talent

Why Kevin is bullish on New York

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