David Siegel - CEO of Meetup | Decisions That Make or Break All Leaders

David Siegel is the CEO of Meetup, the largest platform for finding and building the local community. He has over 20 years of experience as a technology and digital media executive leading organizations through innovative product development, rapid revenue growth, and digital traffic acceleration. Prior to joining Meetup, David was CEO of Investopedia and before that, President of Seeking Alpha. David holds a BA in Philosophy, Politics & Economics and an MBA from the University of Pennsylvania. He is an adjunct professor at Columbia University where he teaches strategic planning and entrepreneurship. He hosts the podcast Keep Connected, which is dedicated to the power of community. David’s book, Decide & Conquer,(HarperCollins) lays out the framework for decision-making that leaders can use to ensure organizational and personal success.

➡️ Talking Points

00:00 — Intro

04:02 — David Siegel's origin story

06:33 — David’s pre-Meetup life

09:36 — Assistant to the CEO

11:27 — Early career struggles

15:10 — The most notable part of David Siegel's career

19:41 — David’s leadership book

21:55 — The serial CEO

22:26 — What is the definition of a leader?

23:31 — Leadership principles & shareholder expectations

29:11 — Leadership principles

37:00 — Decision-making process

38:46 — How to hire

40:33 — Skills to hire for

44:25 — The importance of de-prioritization

46:15 — Lessons from David’s book

47:34 — Where do people connect with David Siegel?

48:19 — What was the biggest challenge of David's career?

48:51 — David Siegel’s mentor

49:39 — David Siegel’s book or a podcast recommendation

50:38 — What would David tell his 20-year-old self?

51:04 — What does success mean to David Siegel?