Uploaded June 2026 | Updated September 2026, 2 days ago
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
27:15 — Why Young People Are Lonelier
29:21 — Meetup's Biggest Product Mistake
34:22 — The DEI Debate at Meetup
40:08 — October 7th Changed Everything
59:57 — Mandatory Service Ends Loneliness
RESOURCES
Follow David on Linkedin: linkedin.com/in/davidmsiegel
Subscribe to Invested: https://content.aleph.vc/invested
Learn more about Aleph: aleph.vc
Sign up for Aleph’s monthly email newsletter: https://newsletter.aleph.vc/
Subscribe to Aleph’s YouTube channel: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: https://x.com/aleph?s=20
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: instagram.com/aleph.vc
CREDITS
Executive Producer: Erica Marom
Producer: Sofi Levak, Myron Shneider, Dalit Merenfeld
Video and Editing: Nadav Elovic
Music and Creative Direction: Uri Ar
Content and Editorial: Jackie Goldberg
Design: Nimrod Sapir
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
27:15 — Why Young People Are Lonelier
29:21 — Meetup's Biggest Product Mistake
34:22 — The DEI Debate at Meetup
40:08 — October 7th Changed Everything
59:57 — Mandatory Service Ends Loneliness
RESOURCES
Follow David on Linkedin: linkedin.com/in/davidmsiegel
Subscribe to Invested: https://content.aleph.vc/invested
Learn more about Aleph: aleph.vc
Sign up for Aleph’s monthly email newsletter: https://newsletter.aleph.vc/
Subscribe to Aleph’s YouTube channel: youtube.com/@aleph-vc
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: linkedin.com/in/mieisenberg
Follow Aleph on Twitter: https://x.com/aleph?s=20
Follow Aleph on LinkedIn: linkedin.com/company/aleph-vc
Follow Aleph on Instagram: instagram.com/aleph.vc
CREDITS
Executive Producer: Erica Marom
Producer: Sofi Levak, Myron Shneider, Dalit Merenfeld
Video and Editing: Nadav Elovic
Music and Creative Direction: Uri Ar
Content and Editorial: Jackie Goldberg
Design: Nimrod Sapir
