Jerry Colonna on Radical Self-Inquiry for Startup Founders and Investors

The Capital Stack

Jerry Colonna, executive and life coach of Reboot.io, discusses the importance of personal growth and self-inquiry for startup founders. He shares his own journey of rebooting and how it led him to become a coach. Colonna emphasizes the need for founders to confront their own brokenness and take responsibility for their actions. He also explores the challenges faced by investors and the need for empathy and self-soothing in the startup ecosystem. Jerry Colonna discusses the state of investing and the need for a shift in focus from financial returns to building meaningful relationships. He shares the genesis of his work with Reunion and the importance of personal growth and being a better human. Jerry also explores the impact of systematic racism and oppression, as well as the fear of the other in society. He emphasizes the moral responsibility of business leaders to address these issues and create positive change. The conversation concludes with a discussion on the next iteration of Jerry's work and the importance of asking meaningful questions. You can watch/listen to the podcast on YouTube, Spotify, and Apple.

Takeaways

• Personal growth and self-inquiry are essential for startup founders to navigate the challenges of entrepreneurship.
• Confronting one's own brokenness and taking responsibility for one's actions is a crucial step in personal growth.
• Investors should lead with empathy and self-soothe their own anxieties to create a healthy and supportive environment for founders.
• The startup ecosystem needs to address systemic issues and lower expectations to foster a more realistic and sustainable approach to entrepreneurship. Investing should focus on building meaningful relationships rather than solely pursuing financial returns.
• Personal growth and being a better human are essential for effective leadership.
• Systematic racism and oppression must be acknowledged and addressed.
• Business leaders have a moral responsibility to create positive change in society.

Chapters

03:20 Rebooting and Radical Self-Inquiry

08:57 Reunion and Personal Growth

16:05 The Importance of Painful Work

25:15 The Role of Investors in Founder Dishonesty

27:48 The Systemic Issues in Startup Culture

29:09 The State of Investing

30:06 The Importance of Relationships

31:15 The Genesis of Reunion

33:03 A Pointing Out Instruction

34:29 Systematic Racism and Oppression

36:00 Fear of the Other

37:00 Radical Self-Inquiry and Leadership

39:08 Attacking Ideologies and the Real Problems

40:30 The Moral Responsibility of Business Leaders

42:22 The Next Iteration of Jerry's Work