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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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In this heartfelt solo episode, Jr opens up about a lesson that reshaped his entire podcasting journey. After his first speaking engagement left him questioning what he’d been teaching, he realized he’d been following templates instead of truth.
He shares how chasing formulas, quick monetization, and the “perfect” structure nearly stripped the authenticity from his voice—and how he rebuilt his creative foundation by focusing on community, experimentation, and real human connection.
💡 Key Takeaways:
- Don’t copy templates—customize your structure and stay flexible.
- Monetization should fit your growth, not force it.
- Ignore one-size-fits-all hacks—build a system that works for your audience.
- Remember why you started, and never lose the human side of your show.
🔥 Quote of the Episode:
“Monetization should fit your growth, not force it.”
🎧 Listen if you’ve ever felt burned out, boxed in, or pressured to follow someone else’s path. This one’s about rediscovering your voice, your purpose, and your podcast’s heart.
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