Episode 5: From Triplex to Chimney Sweeping Woes episode artwork

EPISODE · Feb 5, 2026 · 48 MIN

Episode 5: From Triplex to Chimney Sweeping Woes

from Simmons Sooty Stories · host Trent Simmons

Send us Fan MailWelcome back to Simmons Sooty Stories! In this episode, Jeff and Trent dive deep into the early, "scrappy" years of the business and married life. From living in a colorful triplex on 8th Street to the hard lessons learned while working out of a spare bedroom, this is a look at the "sooty" foundations of Top Hat Chimney Sweeps.In this episode, we cover:The 8th Street Triplex: Life in the "eclectic" neighborhood where their secretary lived next door, and the neighbors included a drug dealer and a prostitute.The "Devil" on the Porch: Jeff recounts the most terrifying night of his life involving a dark back porch, a lack of railings, and a "demon" with glowing red eyes that turned out to be much smaller (and furrier) than expected [22:32].Jeweler Screwdrivers & Justice: Hear the legendary stories of Jeff chasing down mailbox thieves, confronting a building intruder with nothing but a tiny screwdriver, and the bizarre encounter with a "naked" intruder in his shed [34:29].Preacher Landlords & Evictions: The frustrations of renting in Alabama, including a literal "runaround" with a policeman trying to serve an eviction notice for a landlord who couldn't spell Jeff’s name right [27:37].The $25 Business Mistake: Jeff opens up about "working his way out of business" by only charging $25 per sweep and how a life-changing pricing seminar (and his wife Denise’s boldness) saved the company [44:56].Key Takeaways for Entrepreneurs:Jeff shares the pivotal moment he realized that professionalism and thoroughness require a business model that actually covers the bills. If you’ve ever been scared to raise your prices, this episode is a must-listen!Watch the full episode on YouTube: https://youtu.be/zuym18DpgY8Follow us for more stories:Instagram: @TopHatChimneyAUWebsite: www.CallTopHat.comDon’t forget to participate in our listener challenge! The first person to accurately retell one of Jeff's stories wins a Dogfish Head bottle opener!#SimmonsSootyStories #ChimneySweep #SmallBusiness #EntrepreneurLife #AlabamaHistory #PricingForProfit #PodcastStoriesPodcast WebsiteFacebookYoutubeInstagram

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Send us Fan Mail Welcome back to Simmons Sooty Stories! In this episode, Jeff and Trent dive deep into the early, "scrappy" years of the business and married life. From living in a colorful triplex on 8th Street to the hard lessons learned while working out of a spare bedroom, this is a look at the "sooty" foundations of Top Hat Chimney Sweeps. In this episode, we cover: The 8th Street Triplex: Life in the "eclectic" neighborhood where their secretary lived next door, and the neighbors includ...

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Episode 5: From Triplex to Chimney Sweeping Woes

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