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Reboot: CEO Coaching and the Emotional Side of Leadership (Jerry Colonna)

Jerry Colonna · Reboot.io Freemium Intermediate

Jerry Colonna was a top-tier VC before he became the coach founders call when the company is doing fine but they are not. Reboot is the canonical example of a practitioner who genuinely gets startups: his radical self-inquiry blends operating reality with the unconscious patterns underneath, which is exactly the coaching-that-shades-into-the-deeper-work you want. The free Reboot Podcast archive lets you hear real founders do this work before you ever pay for a session.

  • Look for a coach who has lived the founder or investor seat, not a generic executive coach, because startup pattern-recognition is the whole value
  • Colonna's radical self-inquiry treats your unconscious patterns from past experience as the real lever on present-day leadership behavior
  • Start free: the Reboot Podcast is founders working through their own fear and doubt out loud, a preview of what founder coaching actually feels like
Open on reboot.io ↗

The question it answers

  1. Is founder therapy or coaching actually worth it, and how do I find someone who gets startups?

Read with it

  1. Buechler was Y Combinator's in-house founder coach and therapist, so this is the rare piece written by someone who has sat... Scale Yourself (Amy Buechler) Article · 10 min read The Difference Between Coaching and Therapy (for Founders) Amy Buechler
  2. This is one of the earliest honest pieces from inside the Indian startup ecosystem to name founder depression out loud, with... YourStory Article · 8 min read Is Depression a Well-Guarded Secret in the Startup World? YourStory
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