

190: Box of Cigars and A Bottle of Whiskey & Reverse Benjamin Button
Jul 21, 2025
Jake and Gareth tackle advertising strategies while hilariously addressing how two youthful callers can gain respect at work. They explore nostalgia with funny stories about a quirky windowless van and brainstorm creative marketing ideas. The hosts also dive into the challenges of youthful appearances in professional settings, sharing tips on how to project maturity. Expect lighthearted banter and a vibrant discussion about friendship, community engagement, and the joy of looking youthful when working with the public.
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Creepy Van Turned Friendly
- Paige's boyfriend acquired a creepy, windowless 2003 white astro van near a grade school for just a box of cigars and a bottle of whiskey.
- The hosts pitched turning the van into a friendly, branded work van wrap to make it less scary and promote the podcast.
Wrap Van for Friendly Branding
- Wrap the creepy van in colorful, friendly artwork advertising Connor's plumbing and handyman business.
- Use cartoon versions, contact info, and brand it as a work van to reduce creepiness and promote the business.
Connor Embraces Van Wrap Idea
- Connor, the boyfriend, joined the call and expressed excitement about wrapping the van with podcast and Chicago Bears branding.
- The hosts joked about the wrap improving podcast numbers and protecting kids by making the van inviting and fun.