Lenny's Podcast: Product | Growth | Career

How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

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May 8, 2025

Jerry Colonna, a renowned executive coach and CEO of Reboot, emphasizes radical self-inquiry as a tool for transformative leadership. He poses a thought-provoking question about complicit behaviors in creating undesirable conditions. The conversation explores why teams fail beyond mere talent and the personal implications of busyness. Colonna also critiques the concept of a 'growth mindset' and discusses the evolving role of AI in self-discovery. Ultimately, he urges listeners to redefine success by prioritizing authenticity and meaningful legacy.

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00:00 / 00:00

Agency Through Radical Questioning

Ask yourself how you've been complicit in creating the conditions you claim to dislike.
This question evokes your agency and reveals unconscious patterns holding you back.

00:00 / 00:00

Leadership Equation Explained

Leadership success combines practical skills, radical self-inquiry, and shared experiences.
This blend fosters enhanced leadership and greater resilience.

00:00 / 00:00

Success without Assholery

A 19-year-old once asked Jerry if he had to be an asshole to be successful.
Jerry affirmed you can be successful without being miserable or unkind.

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Reboot

Leadership and the Art of Growing Up

Jerry Colonna

In 'Reboot,' Jerry Colonna shares his approach to leadership development through radical self-inquiry. The book helps leaders identify and address the emotional baggage and psychological habits that have both driven their success and hindered their relationships and well-being. Colonna draws on his experiences as a venture capitalist and executive coach, blending Buddhism, Jungian therapy, and entrepreneurial insights to guide leaders in finding meaning, building healthy interpersonal bonds, and becoming more compassionate and bold leaders. The book emphasizes the importance of self-awareness, mindfulness, honesty, and self-critique in transforming both personal and professional lives[2][4][5].

Born to Run

Cathy Freeman

This book recounts Cathy Freeman's journey from a little girl who loved to run to a world champion athlete. It includes her experiences growing up in a loving family, her relationship with her severely disabled sister who inspired her, and her rise to the top in athletics. The book also touches on the challenges she faced, including racism and personal losses, and how she overcame them through hard work, self-belief, and the support of her family. The narrative is honest and simple, making it relatable to young readers. The book is accompanied by black and white photos, some of which are family shots, adding a personal touch to the story[2][4].

10% Happier

Dan Harris

In '10% Happier,' Dan Harris shares his personal journey of discovering the benefits of meditation. Initially a skeptic, Harris, a news anchor, found himself on a path of self-discovery after a nationally televised panic attack. He delves into the world of spirituality and self-help, encountering various figures including brain scientists, CEOs, and spiritual leaders. The book explores how meditation can reduce stress, improve focus, and enhance overall well-being without compromising one's ambition or edge. Harris emphasizes the importance of mindfulness in making one more resilient and better equipped to handle life's challenges, though it does not eliminate problems entirely[2][4][5].

The Giving Tree

Shel Silverstein

The Giving Tree is a children's picture book that follows the relationship between an apple tree and a boy from childhood to old age. The tree selflessly provides for the boy's needs at each stage of his life, from apples and branches to a trunk for a boat. Despite the boy's increasing demands and eventual neglect, the tree continues to give, highlighting themes of unconditional love, selflessness, and the consequences of human actions on nature. The book is a powerful metaphor for life, love, and the importance of appreciating and respecting the gifts of nature and relationships.

Soldiers and Kings

Survival and Hope in the World of Human Smuggling

Jason DeLeon

Jason DeLeon's "Soldiers and Kings" delves into the world of human smuggling along the US-Mexico border. Through extensive fieldwork and interviews with smugglers, DeLeon offers a nuanced perspective on the complexities of migration. The book challenges conventional understandings of smuggling, highlighting the motivations and experiences of those involved. It explores the human cost of migration, the impact of US policies, and the interconnectedness of global issues. DeLeon's work humanizes the often-dehumanized individuals involved in this dangerous trade, prompting reflection on the ethical and political dimensions of migration.