On the Move with Matt Podcast

On the Move with Matt: How a Home Inspector Fell Off a Roof & Still Grew His Business


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Welcome to Episode 18 of On the Move with Matt Podcast
This week’s guest is Ben Morehead, owner of Old Towne Inspection—and yes, he once fell off a roof mid-inspection and lived to tell the tale (with 18 stitches).
In this episode, Ben walks us through how he went from a desk job to building one of the most trusted home inspection companies in Winchester. We talk about what actually happens during a home inspection, what every buyer and seller should know, and how Old Towne Inspection helps people decide with confidence.
Whether you’re in real estate, buying your first home, or just curious what an inspector actually sees in a crawl space—this is a must-watch episode.
What You’ll Learn:
• What really happens during a home inspection
• Why even brand-new homes should be inspected
• How Ben built (and almost overbuilt) his business
• The biggest lessons from nearly burning out
• Why education—not fear—is at the heart of Old Towne’s mission
• And yes… what it’s like to fall off a roof during an inspection
Join the Conversation:
Have questions about home inspections or starting a business the hard way? Drop them in the comments!
About the Podcast:
On the Move with Matt highlights local businesses, stories, and the people who make Winchester and the surrounding area a great place to live. Whether you’re a local or planning a move, we’re here to help you discover everything this community has to offer.
Matt Kilmer -Realtor®/Salesperson
Samson Properties
Licensed in VA & WV
📱 540-931-6089
VA Broker - Katie Jordan
2 N Kent Street
Winchester, VA 22601
540-348-4911
WV Broker - Nancy Williams
1355 Edwin Miller Blvd Ste A
Martinsburg, WV 25404
304-918-2740
Equal Housing Opportunity
...more
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On the Move with Matt PodcastBy Matt Kilmer