Shoot The Moon

The Sell Side Masterclass for Tech Services Founders: Knowing When It’s Time to Sell

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EPISODE 237: In this first installment of the M&A Master Class Series for Sellers, the Revenue Rocket partners break down one of the toughest decisions for any founder: knowing when it’s time to sell. Mike, Matt, and Ryan explore how to read the signals that you’re ready, the emotional and financial factors at play, and the difference between “selling out” to move on versus “selling in” to grow bigger. Whether you’re feeling burned out, hitting growth ceilings, or just wondering what’s next, this episode helps you self-assess where you are and what comes next in your journey.

 

In This Episode:

  • Why deciding to sell your business is one of the hardest calls a founder makes
  • Emotional factors behind the decision — purpose, identity, and timing
  • Early “readiness signals” and how to spot them
  • The difference between selling out vs. selling in
  • The “Sunday Test” and “Three-Year Test” how to self-assess your motivation
  • The importance of alignment at home before you make the decision
  • Low-stakes steps to start preparing today: valuation, readiness checks, and building your advisory team

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    Key Takeaways:

    • Selling isn’t quitting: it’s moving to the next chapter.
    • If you’re dreading Monday, it may be time to sell out.
    • If you’re energized about new growth, selling in might be the better path.
    • Confidence, alignment, and preparation are the foundation of M&A readiness.
    • A trusted advisor helps you navigate both the emotional and financial journey.

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      Related Episodes:

      • Episode 235: Tell Tale Signs it is Time for an Exit. Listen now >>
      • Episode 222: Seller Readiness: What to Do When a Buyer Comes Knocking. Listen now >>
      • Episode 214: When to Sell Employees you are Selling the Business. Listen now >>

        • Listen to Shoot the Moon on Apple Podcasts or Spotify.

        Buy, sell, or grow your tech-enabled services firm with Revenue Rocket.

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