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

Episode Summary

Executive Summary: In this episode of This Week in Startups, Jason Calacanis interviews Jerry Colonna, a venture capitalist turned executive coach. Colonna shares his journey from a driven, aggressive founder and VC to a coach focused on founder well-being. He discusses the dark side of success, including depression and suicidal ideation, and emphasizes the importance of self-inquiry, purpose, and evolving from a 'berserker' to a 'deft' leader. The conversation explores how founders can maintain competitiveness without sacrificing happiness, and the need to redefine success beyond external validation.

Main Topics: Jerry Colonna's Journey from VC to Coach (Priority: 5/5): Colonna recounts his early career, from hawking a magazine to becoming a successful VC at Flatiron Partners, and his eventual pivot to coaching after experiencing depression and a pivotal moment of suicidal ideation. The Dark Side of Success (Priority: 5/5): Discussion on how success can lead to misery, anxiety, and a sense of emptiness, illustrated by Colonna's own experience and the example of Michael Jordan. Founder Psychology and Motivation (Priority: 4/5): Exploration of the psychological drivers behind founders, including childhood wounds, the need to prove oneself, and the transition from founder to CEO. The Role of a Coach (Priority: 4/5): Colonna explains when and how he works with founders, focusing on helping them navigate transitions, manage people, and find purpose. Evolving Leadership Style (Priority: 4/5): The shift from a 'berserker' aggressive style to a more 'deft' approach, using a sword only when necessary, as a way to maintain effectiveness without burnout. Redefining Success and Enough (Priority: 3/5): The importance of asking 'how much is enough?' and detaching self-worth from external achievements to find genuine fulfillment.

Key Arguments: Success does not guarantee happiness; it can often lead to increased misery and anxiety. Founders often have unconscious drives (e.g., rescuing a parent) that fuel their ambition but can never be satisfied by external success. It is possible to be competitive and successful without being a jerk, but it requires conscious effort and self-inquiry. The transition from founder to CEO is challenging because it requires managing people and scaling processes, which can be painful. Coaching can help founders navigate difficult decisions like firing co-founders and finding purpose beyond the business.

Data Points: Number of board seats held by Colonna at one point: 27 - Colonna mentions he had too many board seats after leaving venture capital. Years Colonna has been coaching: 23 - He has been coaching for 23 years after training to become a coach. Age when Colonna left venture capital: 38 - Colonna was 38 when he left Flatiron Partners and experienced a crisis. Number of boot camps Reboot has been doing: 10 years - Reboot has been conducting multi-day immersive boot camps for ten years.

Pivotal Quotes: "The more successful I got, the more miserable I became." — Jerry Colonna: Colonna describing his experience as a venture capitalist during the dot-com boom. "I made the best decision of my life at that moment. I decided not to jump in front of that train." — Jerry Colonna: Colonna recounting his moment of suicidal ideation at Ground Zero in 2002. "The problem is not the process. The problem is not the industry as much as the setup of what we believe as we go into it." — Jerry Colonna: Colonna explaining how founders' beliefs about success can lead to suffering.

Implications: This episode underscores the need for founders to prioritize mental health and self-awareness. It challenges the myth that success equals happiness and encourages a redefinition of success. For the startup ecosystem, it highlights the value of coaching and the importance of evolving leadership styles to sustain long-term fulfillment and effectiveness.