Episode Details

You never know where someone’s career will take them, and Jay Schwedelson is totally fascinated by Adam Ryan’s unconventional path—from ninth-grade American government teacher to building the B2B creator community platform Workweek. Adam breaks down why the future of content and community isn’t about brands, but about real, trusted personalities—and why “community” might be the most overused word in marketing right now.

Check out everything Adam and his team are building at Workweek, and explore their creator-led communities and content: https://workweek.com/

Best Moments:

(01:45) Lesson plans at 6:30 AM and why Adam left teaching for good

(02:33) Your career isn’t linear—scroll Adam’s LinkedIn if you need proof

(04:45) People crave learning from individuals, not faceless brands

(07:45) When you need trust, a real human should lead your newsletter—even if it’s ghostwritten

(11:13) Why most brand “communities” flop and how Workweek thinks differently

(14:06) Engagement loops are the secret sauce to keeping communities alive

(17:01) The TikTok lesson: relevance is everything for ongoing community value

Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

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Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out April 21, 2026). All net proceeds are donated to The V Foundation for Cancer Research—let’s kick cancer’s butt: https://www.amazon.com/Stupider-People-Have-Done-Marketing/dp/1637635206