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    1. Read
    2. Topics
    3. Real Estate
    4. Tennessee Housing
    5. Learning Through Fire
    4 min
    Learning Through Fire
    Real Estate

    Learning Through Fire

    AAuthor
    October 8, 2026

    Will Cupp is a Sevierville real estate broker with Realty Executives Associates and more than 30 years of experience helping buyers and sellers in East Tennessee. He shares real stories and practical lessons from working in Sevier County and the Smoky Mountains.

    Selling real estate in East Tennessee does not come without meeting some unusual people and dealing with problems that start out strange and somehow become even stranger. As I have said before, learning to sell real estate in the Smoky Mountains means learning to work with people who have, well, let’s just say, a different way of thinking. Of course, they might say the same thing about me. lol.

    Over the years, I have come to a pretty simple definition of a Realtor. There is a buyer, and there is a seller. If I can find two who are compatible and help them come to terms, well, there you go. Sounds easy enough. But let me tell you how I learned not to get ahead of myself.

    In my early days with Century 21, the company where I started, we had a weekly property tour out in Wears Valley. My goodness, one of those homes was a sight. The only thing that didn’t need repair or cleaning up... hmm. Well, I’ll have to get back to you on that. I remember looking at my buddy Randy and saying, “This thing is never going to sell. I don't believe anyone is going to showing it. It’s an absolute dog.”

    There I was, just getting started, already deciding what people would and would not buy. And because God has a sense of humor, guess who was on floor duty when the phone rang? A couple wanted to see a property. You guessed it. The Wears Valley dog. Said it was exactly what they had been looking for. Huh! But me being me, I said, “Great, I’ll meet you there in an hour.” Didn’t want to give them time to change their minds. lol.

    They were so excited. They loved the area, their parents lived in the neighborhood, and the hubby was a handyman. Well, now we were getting somewhere. I had been looking at everything wrong with the house. They were looking at what made it right for them. God bless those two. Then came the next little detail: “Will, we have a house to sell first.” lol. I’ll leave it there.

    The point of the story is, I still don’t live in the mind of a buyer. More than 30 years in this business has taught me a lot, but it has not given me the ability to look at a house and know what it might mean to somebody else. That couple had reasons to love it that I knew nothing about until I listened. Their parents were nearby. He could do the work. What I saw as a problem, they saw as an opportunity.

    That is one of those lessons you carry with you. Experience helps me give advice, but sometimes experience also reminds me to keep my mouth shut long enough to learn something. Randy might have appreciated me learning that one a little sooner. lol.

    There is a buyer, and there is a seller. If I can find the two and help them come to terms, well, that’s a gift I am glad God has given me. I see real estate differently because of moments like that. A home, well, it’s where a family lives. It’s where the heart beats. And i can tell you ths from the bottom of my heart, I still love to see that happen.

    And to think, I wasn’t even going to show it.

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    Will Cupp

    @willcupp

    Real Estate Agent

    Will Cupp is a Sevierville Realtor and real estate broker with Realty Executives Associates serving Sevierville, Pigeon Forge, Gatlinburg, Wears Valley, Sevier County and the Great Smoky Mountains of East Tennessee. With more than 30 years of real estate experience, Will helps buyers and sellers with Smoky Mountain real estate, homes, cabins, luxury cabins, vacation homes, short term rentals, STR properties, investment properties, land and acreage. His experience includes cabin sales,property marketing, negotiation, relocation, real estate auctions and helping out of state owners sell property in the Smokies. Will writes about real deals, real properties and lessons learned from more than three decades of buying, selling, negotiating and solving real estate problems in the Smoky Mountains

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