Creating luck through optionality

David and Michael discuss planting seeds, optionality, asymmetric upside, and expected value in career decisions.

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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.

More on in the episode:

Why loneliness is more dangerous than smoking
How Meetup grew into a global community platform spanning nearly every country
The surprising origin story of Meetup after 9/11
Turning around a WeWork company losing $20 million annually
Why social media increased loneliness instead of reducing it
The cultural and technological drivers behind rising social anxiety
Leadership lessons from building and selling companies
The power of decision-making and creating your own luck
Israel Tech Mission and bringing global tech leaders to Israel
Why David believes mandatory national service is the best solution to the loneliness epidemic
What Israel gets right about meaning, community, and belonging

David Siegel is the former CEO of Meetup, the largest platform for finding and building local community. He has had two exits over the last six years where he drove investor returns of 5x and 7x. Prior to Meetup, David served as CEO of Investopedia and President of Seeking Alpha. Today he advises CEOs, serves on boards, teaches strategy and scaling at Tel Aviv University, hosts the Keep Connected podcast, and leads the Israel Tech Mission, which has brought hundreds of global technology executives to Israel.

If you want to understand leadership, community, loneliness, company turnarounds, and what creates meaning in modern life, this episode is essential viewing.

Please rate this episode 5 stars wherever you stream your podcasts!

KEY TOPICS

00:01 — Loneliness Worse Than Smoking?

02:03 — The Anti-Wall Street Career Path

05:04 — The DoubleClick Mafia Explained

08:23 — From HR to CEO

11:13 — How Michael Changed David's Career

13:27 — Adam Neumann's ‘27 Interviews’

16:36 — Retired at 50. Then What?

18:08 — Meetup Was Born After 9/11

21:36 — Fixing A $20M WeWork Money Pit

24:02 — Revenue Is Not Evil