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When to Fire Yourself (and Other Hard Decisions)

Look, we all like to think we’re the irreplaceable visionary at the heart of our companies. But if you’re truly committed to scaling, there comes a point where your unique skills might be holding the venture back. This is one of the most difficult, and most necessary, decisions a founder can make.

Why It’s So Damn Hard

  • Ego, Obviously: We tie our identities deeply to our startups. Stepping back feels like admitting failure, even if it’s the opposite.
  • Fear of the Unknown: You’re comfortable as the visionary. Handing over the reins means embracing a new, less defined role. That’s scary for even the most success-driven founders.
  • Loyalty Isn’t Always Logical: You might have early team members who are fiercely devoted, but not up to the task as the company grows. Those are heart-wrenching conversations to have.

Signs It’s Time (Beyond the Obvious P&L Disaster)

  • You’re the Bottleneck: Are decisions constantly waiting on you, when they could be made competently by others with the right systems? This strangles growth.
  • You Hate Your Day-to-Day: If the tasks of running a larger company bore you, it’ll show. Your team, and your investors, will pick up on this disengagement.
  • There’s a Clear “Better Fit”: Maybe you found someone with deep industry expertise, or proven operational experience scaling ventures. This is about opportunity, not inadequacy.
  • Your Board (or Mentors) Are Hinting: If people you trust are gently suggesting this shift, take it seriously. They likely see something you don’t.

How to Do It Right

  • This IS the Long-Term Vision: Frame it as fulfilling the potential of the company you built, not abandoning it.
  • Plan the Transition, Don’t Abdicate: Work with your successor to ensure a smooth handover. Your knowledge is still vital, but in a different form.
  • Define Your New Role: Do you stay on the board? Focus on strategic partnerships? This gives you some structure going forward.
  • Be Honest With Yourself…and Your Team: Trying to fake it until you make it as CEO will only make things worse. Transparency earns respect, even when difficult.

Have you had this experience – either stepping back yourself, or seeing another founder do it well? Let’s share what we’ve learned in the comments!

Trai Sasatavadhana

Hi! I am a venture builder/corporate venture capitalist. I find and fuel the startups that will change the world.

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