347: Date Like A Salesman on DIYS w/@Charliewilsontvlive

Head to to get your free gift with purchase, and start The Good Habit today! If you like your money, Mint Mobile is for you. Shop plans at Patrick Cloud sits down with comedian, host, and luxury car salesman Charlie Wilson for one of the most honest and insightful conversations on Damn Internet, You Scary! This episode covers Charlie’s wild career journey from Louisiana to Dallas to New York to Vegas to Chicago to Los Angeles, and how he built a life across car sales, stand-up comedy, hosting, producing, and live entertainment. They talk about: what it was really like selling Volkswagens, Cadillacs, Range Rovers, and Maseratis how car sales taught Charlie how to read people and close how he got into stand-up comedy his first TV pilot experience how he became the host of a Star Wars burlesque show what life on the road is really like with live entertainment residencies tea rituals, anxiety, and creating a calmer morning routine stretching, health, and protecting your body while working nights leaving comfort behind to build something bigger why fear keeps people from betting on themselves how to balance multiple careers while still chasing the long game This episode is a real conversation about hustle, reinvention, timing, and building a creative life that actually fits who you are.

You can listen to 347: Date Like A Salesman on DIYS w/@Charliewilsontvlive online on Radio and Podcast. Open the player on this page to stream the available audio.

347: Date Like A Salesman on DIYS w/@Charliewilsontvlive is an episode from Dam Internet, You Scary!.

This episode is 61:37 long.

This episode was published on Mar 27, 2026.

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