E35 - It Got Hard. We Kept Going - A Conversation with 2025 Franchise Business Owner of the Year Greg Dupey

E35 - It Got Hard. We Kept Going - A Conversation with 2025 Franchise Business Owner of the Year Greg Dupey

From PTPPodcast by Pillar To Post Home Inspectors

April 13, 2026 · 44 min · Episode 35

About this episode

Greg Dupey discusses leadership and business strategies during challenging market conditions.

What does strong leadership really look like when the market turns against you? In this episode of the PTPPodcast, Charles sits down with 2025 Franchise Business Owner of the Year Greg Dupey for a candid conversation about navigating one of the most difficult stretches many business owners have faced in recent years - and what it takes to come out stronger on the other side. Greg shares how waived inspections reshaped his local market almost overnight and why survival itself became the short-term goal for a period of time. He also explains what helped rebuild momentum, including a return to growth of more than 30 percent and the strategic purchase of another inspection company. More importantly, this conversation gets into the thinking behind those moves. Greg talks about the role of long-range vision, staying disciplined when conditions get uncomfortable, surrounding yourself with strong people, and continuing to invest in the business even when the timing doesn’t feel perfect. If you’re thinking about what the next level of your business could look like, or how to stay steady while you build toward it, this is a conversation worth spending time with.

People in this episode

Host: Charles

Guest: Greg Dupey

Topics covered

Keywords

Mentioned in this episode

Organizations: Pillar To Post Home Inspectors

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