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Today’s show:

Jerry Colonna joins Jason in person for a philosophical dialogue about the search for meaning as an entrepreneur, drawing on their multi-decade friendship. They explore Jerry's personal journey from venture capitalist to founder coach (11:08), the challenges leaders face as startups evolve (40:03), how Jerry helps entrepreneurs transition from founder to CEO (28:54), and much more!

Timestamps:

(0:00) Jerry Colonna joins Jason (1:14) Jason's early internet days and first taste of money/power (10:08) Corient - Speak with one of Corient's wealth management advisors today at http://corient.com (11:08) Jerry's journey as a venture capitalist during the peak Dot-com era to founder coach (18:32) What pushed Jerry to his limits, and how did Jerry overcome his depression (23:36) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (24:56) Jerry's Book "Reboot" and what Jerry sees drives founders (28:54) How to transition from a founder to a CEO (38:31) Coda - Get started for free at https://coda.io/twist (40:03) Finding the right motivation and the steps to being an enlightened leader (57:01) Acute issues that founders contact Jerry about * Check out Reboot: https://www.reboot.io/reboot-leadership-and-the-art-of-growing-up/ Check out reunion: https://www.reboot.io/reunion-leadership-and-the-longing-to-belong/