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5 Piercing Questions You Need To Ask Yourself If You’re Considering Selling Your Startup

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Should I exit or should I stay the course?

It’s THE single biggest question that nearly every successful founder will eventually be met with.

And after taking my coaching clients for a private sit down with Chris Savage at Wistia…

… it got us all thinking about the best ways to evaluate whether or not it’s time to exit and start fresh… or buckle in and continue down the path.

Inspired by Wistia (and many other founders I’ve had the privilege of sitting down with), this week’s episode covers the five key questions you need to ask yourself to arrive at a clear decision that feels both aligned and in the highest interest to your team members and stakeholders.

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At a high level, the five questions to consider are as follows:

  1. Passion or exhaustion?
  2. If crushing?
  3. Build it again?
  4. Pivot or persevere?
  5. Perfect execution?

The FIRST question you need to ask yourself is whether or not you’re still in love.

Meaning, are you still absolutely passionate about the problems you’re solving and the audience you’re solving it for? Or are you just going through the motions?

I see so many founders that pivot their way “out of love” and end up with something that while successful, just leads to exhaustion and constant curiosity around new possibilities.

As a founder and leader, your passion is your fuel.

It MUST be protected at all costs.

And if you find it waning… it might be time to start considering your next move.

Give the full episode a spin here, and then drop me a comment letting me know any major insights or points of clarity that come from it.


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