Tales Behind The Sales

Comedy EN ↓ 5 episodes

Tales Behind The Sales pulls back the curtain on real estate - the wins, the chaos, and the wildly unpredictable humans in between. Hosted by real agents who live this life daily, every episode dives into the stories we usually only tell in private: deals that almost died, miracles pulled off at the last minute, clients who tested our faith, and the moments that remind us why we love (and occasionally question) this business. It’s real. It’s raw. It’s occasionally ridiculous. But every tale comes with a lesson, and a laugh.

Author

Tales Behind The Sales

Episodes

When Showings Go Feral 16.04.2026 33:08

Debb kicks things off with a home inspection that quickly takes a turn straight into the wild kingdom—because apparently, some properties come with more… wildlife than listed. What starts as a routine walkthrough turns into something that feels better suited for Animal Planet than real estate. Then Winston brings the story of a mother and daughter heading out for what should’ve been a normal home...

The Father, the Son, and the Haunted Home 29.10.2025 27:32

In this episode of Tales Behind the Sales , Debb dives into one of her most confusing transactions yet — a father and son duo same name, buying at the same time, with the same lender, in the same area. One smooth deal… one MIA seller… and a whole lot of “Wait, which one are you talking about again?!” Then Winston keeps the Halloween vibes alive with the story of a 1920s Victorian home that might’v...

Termites, Trouble, and a Fugitive on the Loose 22.10.2025 24:24

In this episode, Debb unpacks a jaw-dropping story of a buyer who ignored every red flag — including a listing that literally admitted the home had five years of termite history. Sometimes “as-is” means run while you can! Then Winston raises the stakes with a wild tale straight out of a true-crime special: an agent trying to show an investment property while a wanted criminal was on the run nearby...

The Worst Deal Ever… and the Satanic Surprise Showing 15.10.2025 20:33

This week, Debb drops a doozy — the kind of deal so chaotic her own, then, broker declared it “the worst she’d ever seen.” From last-minute disasters to a buyer demanding a closing gift… AFTER closing, this transaction had more audacity than paperwork. Meanwhile, Winston takes us on a trip to Reddit Hell — and we mean that literally — retelling a showing that may or may not have taken place in a f...

Pilot - Tales Behind The Sales 09.10.2025 45:33

Winston and Debb kick off Tales Behind The Sales with two deals straight out of a sitcom. One starts with a “scheduled” Zillow showing that wasn’t actually scheduled — cue contracts, chaos, and unstable legal advisor. The other? Debb brings the heat with a showing that involved more keys than a high school janitor… and one of those keys opened a shed with a completely naked man living inside. No u...