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EP 007 · 13 Oct 2025 · 60m

Tomorrow's World with Jerry Colonna

Jerry Colonna portraitPortraitJerry Colonna

EP 007 · 13 Oct 2025 · 60m

Tomorrow's World with Jerry Colonna

Jerry Colona is the co-founder and CEO of Reboot, a leadership coaching company built on the belief that better humans make better leaders. Before Reboot, he was a venture capitalist in New York, co-founding Flatiron Partners and later working with JPMorgan Partners.

EP 007·60m
Tomorrow's WorldDo Radio

The conversation

What we talked about.

Jerry Colonna talks about leadership, money, depression, second adulthood and the private cost of public success. The conversation moves from venture capital and the early internet to Buddhism, psychoanalysis and the question of whether a successful life can still be the wrong life.

This episode explores:

  • Why can outward success still leave someone asking, 'is this all there is?'
  • What happens when the inner life and the outer career are no longer aligned?
  • How did the early internet and venture capital shape a generation of leaders?
  • Why do so many high-achieving adults reach midlife with broken hearts?
  • Can technology help us become more connected, or does it mostly amplify our disconnection?
  • What would leadership look like if it started with honesty about suffering?
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