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Reboot.io

2 resources from Reboot.io we point founders to, and the questions each answers.

🛠️ Tool
✓ Link checked Freemium Intermediate

Why we picked it 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.

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

From Reboot.io by Jerry Colonna Site plus podcast archive

  • 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 reboot.io →
Answers Is founder therapy or coaching actually worth it, and how do I find someone who gets startups?
🎧 Podcast
✓ Link checked Free Intermediate

Why we picked it This is the canonical first-hand account of exactly what you are describing. Rand Fishkin walks through his 'long, ugly year' of depression after years of scaling Moz, and Jerry Colonna, the coach founders go to when they crash, names the mechanism: your identity got fused to the company, and the numbness is the bill coming due. The episode opens with a room of VC-backed CEOs asked who struggles with serious depression, and nearly every hand goes up. It reframes numbness as a common late-stage founder state, not a personal defect, and models the radical self-inquiry that starts the recovery.

Depression and Entrepreneurship (Jerry Colonna in conversation with Rand Fishkin)

On Reboot.io by Jerry Colonna (Reboot) with Rand Fishkin (Moz) ~50 min listen (full transcript linked)

  • The emotional flatness after years of hustle is common among founders and tied to fusing your self-worth to the company, not to laziness.
  • You cannot think or grind your way out; recovery starts with honest self-inquiry into why you kept riding the tiger.
  • Saying it out loud to even one other founder breaks the isolation that keeps the numbness in place.
Open reboot.io →
Answers After years of always-on hustle, I feel completely numb and don't care about anything anymore. Is this the end, and how do I recover?