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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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A decade-long dream finally materializes! After years of creating content and navigating the ups and downs of podcasting, the Trading Post podcast has secured its first official sponsorship deal. This unexpected milestone arrived suddenly, catching me off guard despite having uploaded only 11-12 episodes total with sometimes months between releases.
The sponsorship opportunity involves exchanging airtime or mentions for tickets, opening exciting possibilities but also raising numerous questions. I'm now working with a consultant to navigate the business side of content creation—exploring everything from legal disclosures to potential tax implications and whether establishing an LLC makes sense. What started as a passion project about trading and bartering has suddenly transformed into what I jokingly call a "side come"—where opportunities come your way through consistent effort.
Recording challenges remain a fascinating part of my podcasting journey. Despite having access to workspace facilities, my car provides the environment where I feel most authentic and animated. I've experimented with various GarageBand settings from "narrator" to "radio ready" to find the right sound quality. Looking ahead, I'm considering using professional recording spaces for guest interviews while dreaming of an ultimate mobile podcast studio—perhaps a customized RV that embodies the rugged Trading Post brand. The lesson for fellow podcasters? Stay consistent, create content that excites you, and view sponsorships as a welcome bonus rather than the primary goal. Subscribe to follow this exciting new chapter and discover how persistence eventually pays off, even when the path feels slow and unpredictable.
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Chapters
1. The Unexpected Journey: When Your Podcast Gets Sponsored (00:00:00)
2. Exciting sponsorship announcement (00:00:24)
3. Ten years of content creation (00:01:51)
4. Audio quality and recording challenges (00:03:17)
5. Future plans and dream setup (00:05:20)
6. Closing thoughts and next steps (00:08:00)
39 episodes
