Episode Details

Convincing your boss to embrace testing isn’t easy, but Jay Schwedelson has a smart way to flip the conversation. Instead of begging to try new subject lines or tactics, he shows how to reframe experiments as an insurance policy against being left behind. Plus, he shares a hilarious story about a supermarket parking lot that’ll make you think twice about where you stand with your shopping cart.

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Best Moments:

(01:00) Josh asks how to convince a CEO to try proven email tactics instead of sticking to personal preference

(02:28) Why creating a 10 percent “laboratory environment” changes the way testing is perceived internally

(03:31) Framing experiments as an “insurance program” to prevent competitors from pulling ahead

(05:26) Using AI prompts to quickly benchmark your marketing against competitors and show executives the gaps

(08:00) Jay debates whether to shop after being dive-bombed by a bird in the parking lot

(09:26) A cart-return showdown in the supermarket lot sparks Jay’s reflection on being a “cart putter backer”

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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