How would you start an MSP in 2026?
Most would copy what’s already been done.
Same services.
Same pricing.
Same positioning.
That’s the problem.
In this solo episode, Brian Gillette breaks down exactly how he’d go from $0 to $1M ARR today - without reinventing the tech, but completely rethinking how it’s packaged and sold.
→ The 3 core offers I’d build: MSP, AI as a Service, and vCSO
→ How to sell outcomes (time, growth, productivity) instead of tools
→ How to reframe managed services as “insurance” (but why you shouldn’t lead with it)
→ Why most MSP marketing fails - and how to fix it without changing your stack
This isn’t about doing more. It’s about saying the right thing, to the right audience, in the right order.
If I were starting over today - this would be the playbook.
Episode Hosts
Brian Gillette
Brian Gillette, the founder of Feel-Good MSP, stands out in the Channel with his unique, empathy-driven approach to sales and client relationships.
Formerly a VP of Sales for an MSP, his expertise now shines as a consultant, where he transforms traditional sales tactics with a focus on understanding and meeting client needs.
Renowned for his strategies in overcoming sales objections, Brian champions selling outcomes over technicalities, emphasizing value, trust, and the importance of peace of mind and productivity for clients. His dynamic, client-centered philosophy makes him an invaluable asset in the MSP landscape.
He is the host of The MSP Sales Podcast and author of the book, "How to Sell a Sh*tload of Managed Services: Without Selling Your Soul"