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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

Guest

Jerry Colonna

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.

01:22:49

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Episode notes

Powerful Questions for Self-Inquiry

Practice radical self-inquiry by asking difficult questions about what you’re not expressing and hearing.
Reflect deeply on communication gaps to foster personal and leadership growth.

Truth in Shared Experiences

Entrepreneurs often pretend everything is perfect, masking real struggles.
Authentic shared experiences in trusted groups create space for honest truth-telling.

Busyness Masks Insecurity

Busyness often masks deeper fears of inadequacy or impostor syndrome.
Success may quiet the critical inner voice but does not resolve it.

Get the Snipd Podcast app to discover more snips from this episode

Exploring Personal Complicity in Unwanted Circumstances

04:06 • 3min

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The Equation for Cultivating Leadership and Resilience

06:56 • 4min

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Redefining Success and Happiness

10:31 • 24min

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From Passion to Pressure

34:17 • 5min

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Innovations in Data Management and Insights from Buddhist Philosophy

38:52 • 4min

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Exploring Legacy and Personal Fulfillment

42:26 • 15min

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Navigating AI and Personal Development

57:14 • 22min

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The Power of Self-Awareness in Leadership

01:19:18 • 3min

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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.

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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.

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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.

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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.

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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.

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.

In our conversation, we cover:

1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”

2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience

3. Why teams most often fail (hint: it’s not lack of talent or strategy)

4. How busyness often masks deeper issues of self-worth

5. Why a “growth mindset” can be problematic

6. The importance of legacy and what it means to live a meaningful life

7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots

8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity

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Where to find Jerry Colonna:

• X: https://x.com/jerrycolonna

• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/

• Website: https://reunion.reboot.io/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Jerry Colonna

(04:12) Jerry’s key question

(06:55) The equation for great leadership

(09:37) The big lie of success and happiness

(12:12) The consciousness hack

(15:56) Getting over the fear of consequences

(20:23) The problem with bypassing our childhood baggage

(23:22) Radical self-inquiry: asking the tough questions

(27:05) Shared experiences: the power of community

(30:25) The trap of busyness and attachment

(40:45) Understanding our own intentions

(46:58) Legacy and purpose

(55:43) Writing for self-discovery

(57:12) The impact of AI on humanity

(01:05:00) Turning a growth mindset into a fixed mindset

(01:11:30) The role of radical self-inquiry in leadership

(01:19:24) Final thoughts and reflections

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Referenced:

• Naropa University: https://www.naropa.edu/

• Fitler Club: https://fitlerclub.com

• Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/

• Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired’: https://www.today.com/popculture/news/will-smith-fame-rcna127830

• Seth Godin’s best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

• The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism

• 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821

• Simon Sinek’s website: https://simonsinek.com/

• Mike Tyson Gives Morbid Response to Young Interviewer’s Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/

• Dan Shipper’s post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318

• Evernote: https://evernote.com/

• Claude: https://claude.ai

• Peter Senge on X: https://x.com/petersenge

• Carl Jung’s quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your

• Parker Palmer on LinkedIn: https://www.linkedin.com/in/parker-j-palmer-5a92b110/

• The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living

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Recommended books:

• Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536

• Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139

• Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511

• 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431

• Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586

• The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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