Jerry Colonna on 'Reunion': sustaining founder drive, enlightened leadership, and more! | E1864

This Week in Startups is brought to you by… Corient. Real wealth requires real solutions. Corient provides wealth management services centered around you. For more information, speak with an advisor today at Corient.com Lemon.io - Hire pre-vetted remote developers, get 15% off your first 4 weeks of developer time at https://Lemon.io/twist Coda. A new doc that brings words, tables and teams together. All your valuable data, plans, objectives, and strategies in one place. Go to https://coda.io/twist to get a $1,000 credit! * 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/ * Follow Jerry X: https://twitter.com/jerrycolonna LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot * Follow Jason: X: https://twitter.com/jason Instagram: https://www.instagram.com/jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin * Subscribe to the Founder University Podcast: https://www.founder.university/podcast