04: How Shawn Freeman Scaled an MSP to $5M and Exited at 1.4x Revenue

From Angel To Exit

Shawn Freeman, founder of a successful managed service provider (MSP), joins Bruce Eckfeldt to share his journey from launching a tech side hustle to scaling a $5M business and executing a 1.4x revenue exit. He reflects on key inflection points in leadership, recurring revenue strategy, and the emotional and operational complexities of being acquired. Shawn’s insights are essential for founder-CEOs preparing for strategic exits.

Key Takeaways

• Recurring revenue is essential for building valuation and predictable growth.
  
• Exit readiness includes tax planning and proper corporate structure from day one.
  
• Leadership means getting out of your own way and empowering others.
  
• Always assume key employees may leave—design systems that don’t rely on them.
  
• Company culture must be intentional, with clear values and psychological safety.
  
• Be cautious of acquirers unwilling to adapt or integrate new ideas.
  
• Involve your leadership team early in potential exit conversations.
• A premium service model requires aligned pricing and long-term thinking.

Links & Resources

• Shawn Freeman

  https://leaderstechacademy.com/
  https://www.linkedin.com/in/shawnfreeman-/

• Subscribe to the Podcast:

  • Find From Angel to Exit on Apple Podcasts, Spotify, Google Podcasts, or wherever you listen. Be sure to hit “Subscribe” so you never miss an episode.

• Newsletter & Exclusive Content:

  • Sign up for the free newsletter at eckfeldt.com/podcast for episode transcripts, bonus insights, frameworks, and community updates.

• Connect with Bruce & the Community:

  • LinkedIn: Bruce Eckfeldt

  • Instagram: @bruce_eckfeldt

  • Email:

    • [email protected]

    • [email protected]