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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