In this episode of Simmons Sooty Stories, hosts recount their humorous struggles with recording, including a "third or fourth attempt" at part one of their first episode, losing the first half of a previous recording, and technical difficulties with sound and slow motion.

Jeff Simmons, owner of Top Hat Chimney Sweeps, shares the origins of his business, revealing he bought a "going concern" that included a bread truck, tarps, and a "timeless" logo designed by a graphic design student for the previous owner, Ed Weatherman. Jeff recounts working for Ed in the mid-80s while considering buying the business, initially as a side hustle to supplement income from his interior plant business, Interior Plantscapes. He shares how he supplied and maintained plants for various locations like doctors' offices, residences, restaurants, bars, and malls.

The episode delves into Jeff's childhood in Greenville, SC, and his family history, noting that the Simmons side has always been in the South, with ancestors eventually transported to Alabama. He discusses his father, John Riffe Simmons Jr., a dentist who dropped "Junior" from his name to avoid an awkward professional title. His mother, who he says studied "Home Ec" at the University of Minnesota where she met his father, is also mentioned.

Jeff also talks about his two sisters, Jan and Laurie. He shares a story about hitting Jan with a rock from a treehouse and another where he removed the chain from her bike, leading to her crashing into a car and landing on her head.

Finally, Jeff discusses his childhood activities from ages seven upwards, primarily focusing on his swim team days. He describes how his parents would drop him off at the club in the morning and pick him up in the evening. He tried golf but excelled at swimming, especially backstroke, despite it being his least favorite stroke. He was part of a relay team with close friends that set state and Junior Olympic records. He recounts making it to the Olympic trials for backstroke but narrowly missing the Olympics by "one one-thousandth of a second or one ten-thousandth of a second" He attributes his drive to a "Ricky Bobby" mentality: "If you're not first, you're last"