This Week in Startups

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

Dec 13, 2023

01:01:51

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Jerry Colonna, founder drive and enlightened leadership, joins Jason for a philosophical dialogue about the search for meaning as an entrepreneur. They explore Jerry's journey from venture capitalist to founder coach, the challenges leaders face as startups evolve, and how Jerry helps entrepreneurs transition from founder to CEO.

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Quick takeaways

The podcast emphasizes the importance of addressing inner suffering and finding meaning beyond professional achievements.

The episode highlights the unique challenges faced by founders in building and scaling their businesses.

It explores the transformative power of shifting from a purely competitive mindset to one focused on helping others and making a positive impact.

Deep dives

The Importance of Resolving Inner Suffering

The podcast episode discusses the journey of a successful founder and venture capitalist who went through personal struggles and realized that success does not guarantee happiness. The speaker emphasizes the importance of addressing inner suffering and finding meaning beyond professional achievements. The episode delves into the concept of purpose and how it evolves over time. It explores how material success and external validation may lead to a hollow sense of self-worth. Ultimately, the episode highlights the significance of self-reflection and cultivating a sense of fulfillment beyond traditional measures of success.

Introduction

3min

From Homeless to Magazine Founder

6min

The Misconception of Wealth and Fame: Exploring the Negative Correlation

2min

Reflections on Friendship and Personal Experiences

10min

Personal experiences during the dot-com crash and September 11th, and the struggle of startups in fundraising

5min

The Emotional and Existential Aspects of Being a Founder

12min

Managing applicants and attendees with CODA & the struggle of finding enjoyment in success

3min

Reflections on Competitiveness and Shifting Motivations

21min

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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/

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