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August 6, 2025 15 mins

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On Sunday night, I found myself in Golden Gate Park, surrounded by 60,000 fans swaying to “Shakedown Street” and “ Scarlett Begonias” at Dead and Company’s 3 Day Festival celebrating the 60th anniversary of The Grateful Dead. It wasn’t just a concert, it was a living, breathing ecosystem built over decades.

In this episode, I break down what makes the Grateful Dead’s community so unique — from Shakedown Street flea markets to setlists that never repeat, and how their organic growth holds lessons for us as content creators. We’ll talk about why you can’t engineer content that hits the mark, how to nurture an audience once it starts forming, and why authenticity always outlasts trends.

If you’ve been trying to grow your own tribe, this one’s for you.

What you’ll learn in this episode:

  • How the Grateful Dead built a loyal, self-sustaining fan culture
  • The role of surprise, improvisation, and authenticity in keeping audiences engaged
  • Why you can’t “growth hack” your way to a real community
  • How to notice and feed audience behaviors when they start to emerge
  • Why sustainable growth starts with creating what you love

Resources & Links:

  • Try Riverside.fm’s new Co-Creator feature — get 20% off any individual plan with code CLIPPED at riverside.fm
  • Follow me on YouTube: @podcasthaven - The page is growing!
  • More tips, tools, and resources: The Podcast Haven

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