Episode 14  ·  May 12, 2025

Rebuilding the Business You Actually Want to Run

With Brian Gillette and Michael Bakaic

What do you do when your MSP is technically successful - but you’re bored, burned out, or questioning whether you want to keep going? 

In this episode, Michael Bakaic shares the honest story of how he hit a wall and what happened next. After years of grinding through service work that no longer energized him, Michael made the bold decision to pivot. He didn’t just tweak his offer; he rebuilt his entire business around what actually felt good to create, sell, and deliver.

We talk about:

          • Why burnout is often a signal, not a failure

          • The difference between fixing your business vs. reimagining it

          • How simplifying his offer unlocked more freedom

          • Why storytelling closes sales


We also dig into the surprising evolution of Michael’s lead magnet - a cybersecurity audit tool that became his most effective conversation starter. You’ll hear how he repositioned a technical feature into a multi-stage trust-building funnel MSPs can actually use.

If you’re an MSP who’s hit a plateau, or is just tired of white-knuckling your way through growth, this episode is a powerful reminder that you can build something that works for your clients and feeds your soul too.

Learn more about Iceberg Cyber at https://www.icebergcyber.com/

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.

Michael Bakaic

I spent the first 6 years of my entrepreneurial journey being a tech guy that hated sales. That led to burning through $4M and hitting rock bottom. Now I'm paying back that debt by showing tech entrepreneurs how to use cybersecurity as a way to sell without feeling salesy. When you have the right tools, sales feels a lot like helping people solve problems. That's Iceberg Cyber.