How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna

Jerry Colonna, executive coach and former VC, argues that team failures and personal suffering stem from unexamined childhood patterns, not lack of skills or strategy.

• Colonna co-founded Flatiron Partners with Fred Wilson, one of the most successful early-stage VC funds of its era.
• His core equation: practical skills + radical self-inquiry + shared experiences = enhanced leadership and greater resilience.
• Teams most often fail not from lack of talent or strategy, but from unresolved childhood patterns playing out in group dynamics.
• Busyness frequently masks a deeper need to silence an impostor-syndrome voice; the packed calendar is the symptom, not the identity.
• A growth mindset becomes harmful when the ego fixes it as the “correct” approach — turning a flexible tool into an attachment that causes suffering.
• One colleague uploaded 10 years of Evernote journal entries to Claude and used it to surface blind spots, making him a measurably better coach.
• Peter Senge’s observation: it is virtually impossible to challenge the assumptions that made you rich in the first place — beginner’s mind erodes with success.
• The CEO who complained no one made decisions without her had also admitted she became furious whenever they disagreed with her — a textbook complicity example.

2025-05-08 · Watch on YouTube