Part 3: Ashtrays, Idiots of the Week, and Betting on Yourself

Episode 6 – Part 3 Ashtrays, Idiots of the Week, and Betting on Yourself

Part 3 opens in classic Shaffer RULES fashion, by accidentally discovering that ashtrays might actually be an age-appropriate hobby. From handmade elementary school ashtrays (which would absolutely not fly today) to granite cigar ashtrays and repurposed barn lightning rods, the conversation turns into a surprisingly thoughtful take on collecting, cigars, and why pairing bourbon with the right smoke can completely change the experience.

That segues into hobbies, side hustles, and the realization that the podcast itself might be the most “age-appropriate” hobby of all.

Then things take a sharp turn into one of the most unhinged stories of the episode: Idiot of the Week. Corey breaks down a real-life Whatnot auction meltdown where a $24 jewelry purchase spirals into a jaw-dropping, multi-paragraph oversharing saga involving buyer’s remorse, family tragedy, prison sentences, cancer, property taxes, and canceled auctions. It’s a masterclass in how not to handle losing an auction, and a perfect example of why boundaries matter when running a side business.

From there, the episode shifts into something deeper. Corey reflects on Whatnot becoming a legitimate second income stream, the grind behind making it work, and how side hustles can turn into real opportunities, if you’re willing to commit.

The back half of Part 3 gets real. Brian opens up about hitting 50, being done working for “the man,” and finally betting on himself. The guys talk candidly about corporate burnout, being a Swiss Army knife employee, getting pushed out of “forever jobs,” and the difference between surviving and actually being happy. There’s honesty about fear, money, stability, and why taking the shot now matters more than waiting for perfect timing.

The episode closes with wild car-business stories, drunk salesmen, demo cars destroyed in days, repossessions gone sideways, and the kind of characters you only meet in dealerships, before wrapping up a long, loose, but unexpectedly meaningful session.

Part 3 is funny, raw, and reflective, equal parts chaos and clarity, and a fitting close to Episode 6.

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