The Painful Truth About Why Most MSPs Can't Sell - Brian Gillette

In Episode 10 of MSP Insider, host Jeffrey Newton sits down with Brian Gillette, founder of Feel Good MSP and host of the MSP Sales Podcast, for a raw conversation about why most MSPs struggle with sales and the uncomfortable truths about what it takes to grow. Through candid discussion, Brian reveals why technology often creates distance between MSPs and their clients, and how to rebuild the human connection that drives real growth.

Key Topics Covered:
• Why most technical founders struggle with sales psychology
• How to overcome the "victim mindset" in MSP sales
• Why adding more technology often hurts client relationships
• The critical importance of human connection in managed services
• Practical steps for facing sales fears and taking action

Timestamps:
0:00 - Introduction
7:46 - The Victim Mindset in MSPs
15:29 - Overcoming Sales Fear
32:11 - The Human Side of Service
42:07 - Technology vs Connection
54:26 - Key Takeaways

Whether you're struggling with sales or looking to rebuild genuine client relationships, this episode delivers uncomfortable truths about what it really takes to grow an MSP in 2025 and beyond.

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