04: How Shawn Freeman Scaled an MSP to $5M and Exited at 1.4x Revenue
Shawn Freeman, Founder and MSP Coach
In this episode of From Angel to Exit, Shawn Freeman recounts his journey from tech enthusiast to founder and successful exit. Starting his career in IT roles during and after university, Shawn discovered both a passion for technology and a firsthand education in scaling organizations. Dissatisfied with stalled promotions in a fast-growing startup, he began building his own IT consultancy on the side—ultimately evolving into a full-time managed services business.
Shawn launched the business in 2011, just ahead of a downturn in the oil industry, but thanks to early recurring revenue models and a managed services approach—rare at the time—he established financial stability and steady growth. By 2020, his firm had reached $5 million in annual revenue with 25 employees. Key to this success was his early decision to embrace monthly recurring revenue, hire based on predictable sales forecasts, and build a strong, values-based culture with psychological safety.
His exit wasn’t planned. A conversation with a friendly competitor turned into a strategic acquisition offer, driven by the buyer’s need for a Calgary presence. The deal closed at 1.4x revenue and 7x EBITDA, with Freeman retaining equity and the leadership team receiving stock options. However, post-acquisition integration presented cultural challenges, as the acquiring firm resisted change and undervalued Freeman’s premium service model.
Ultimately, Shawn left the company after realizing that his vision and ideas were no longer being heard. He emphasizes the importance of understanding exit readiness, involving the team in exit planning, and maintaining ownership of company culture through transitions. Today, Shawn runs Leaders Tech Academy, a venture focused on empowering executives to manage technology as a strategic asset.
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.
Contact Information:
https://www.linkedin.com/in/shawnfreeman-/
