Conrad Thompson's interest in podcasting began after meeting ECW wrestler Shane Douglas, whom Thompson met after pledging a significant amount of money to a crowdfunding drive for a documentary about ECW. After a positive experience with Douglas, Thompson later approached wrestling manager Jim Cornette with an offer of $1,500 in exchange to come to his house and tell stories for a couple of hours.
In 2013, Thompson met Ric Flair while he was appearing at a local event. Flair and Thompson hit it off, exchanged contact information and became friends.
On July 31, 2022 as part of Starrcast V, Thompson, under the Jim Crockett Promotions banner, promoted his first ever wrestling card with Ric Flair's Last Match, featuring his father-in-law wrestling in his final professional wrestling match.
Thompson resides in Huntsville, Alabama, where he still operates his mortgage company. He married Megan Fliehr in 2018, becoming an in-law to Ric Flair and his children Charlotte Flair and David.