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David Siegel, Former CEO of Meetup & Investopedia, on Solving the Loneliness Crisis, Rescuing Meetup from WeWork, and Why Israelis are Happier than Americans

Invested by Aleph · 2026-06-03 · 1h 3m

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Episode notes

On this episode of Invested, Michael Eisenberg sits down with David Siegel, former CEO of Meetup, former CEO of Investopedia, former President of Seeking Alpha, author of Decide & Conquer, and founder of the Israel Tech Mission. David has spent more than 25 years building and leading technology companies, but his most passionate mission has been tackling one of society’s fastest-growing challenges: loneliness. As CEO of Meetup, he led the global community platform through a dramatic turnaround, transforming it from a money-losing business into a profitable company while helping millions of people connect around shared interests, passions, and causes. In this wide-ranging conversation, Michael and David explore the roots of the loneliness epidemic, why social media and screens may be making people less connected than ever, and what can actually be done to rebuild community in modern society. David shares lessons from leading Meetup through COVID, selling multiple companies, scaling organizations, and retiring from full-time operating roles at age 50.

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