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

Lenny's Podcast: Product | Career | Growth

2025/05/08
Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

2025/05/08
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 experie...

Highlights

In this episode, Jerry Colonna, a renowned executive coach and former venture capitalist, delves into the complexities of leadership and personal growth. With over two decades of experience, Jerry explores how self-awareness and introspection can transform leaders and teams. The conversation covers powerful questions for self-reflection, the pitfalls of unchecked ambition, and the evolving role of AI in personal development.
00:00
Pretense in entrepreneurship leads to superficial engagement.
04:14
The question 'how have I been complicit?' aims to evoke agency.
06:55
Practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resiliency.
09:37
Success does not guarantee happiness; rethinking leadership without misery.
12:12
Asking what success means helps take control of your life instead of being driven by learned behaviors.
15:59
Ignoring discomfort won't make it go away.
20:30
Avoiding childhood baggage can lead to depression or self-sabotage
23:22
Radical self-inquiry involves asking tough questions like 'What am I not saying that I need to say?'.
27:06
Shared experiences involve telling the truth in a non-judgmental group setting.
33:25
Attachment to outcomes can cause suffering.
40:45
Trying to push away suffering by acquiring material things can increase suffering.
50:27
Thinking purposefully about life eases suffering and improves character.
55:43
Legacy might be being a voice of comfort and sanity.
1:04:14
Continuous inquiry is both exhausting and enlivening.
1:05:03
Hold the growth mindset loosely and stay present to changes.
1:11:33
Without individual radical self-inquiry skills, groups repeat patterns from family of origin.
1:19:24
Radical self-inquiry can reduce suffering and increase resilience.

Chapters

Introduction to Jerry Colonna
00:00
Jerry’s key question
04:12
The equation for great leadership
06:55
The big lie of success and happiness
09:37
The consciousness hack
12:12
Getting over the fear of consequences
15:56
The problem with bypassing our childhood baggage
20:23
Radical self-inquiry: asking the tough questions
23:22
Shared experiences: the power of community
27:05
The trap of busyness and attachment
30:25
Understanding our own intentions
40:45
Legacy and purpose
46:58
Writing for self-discovery
55:43
The impact of AI on humanity
57:12
Turning a growth mindset into a fixed mindset
1:05:00
The role of radical self-inquiry in leadership
1:11:30
Final thoughts and reflections
1:19:24

Transcript

Jerry Colonna: We're socialized to bullshit, not only ourselves, but everybody else, especially in the entrepreneurial community. All our companies are moving up and to the right. Every product is working. We don't really have any problems because we're cr...