Partner with Jay: https://www.jayschwedelson.com/contact

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Check out Jay Schwedelson's new book: Stupider People Have Done It

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

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Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter

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Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com

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Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/

Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson

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Ask Jay anything: https://www.jayschwedelson.com/ask

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Leave a comment and follow the show, it really helps us out!

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Register for Guru Conference at guruconference.com to catch Chase’s session on building your newsletter faster with AI. Find Chase Dimond, spelled D-I-M-O-N-D, on all social platforms.

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Hosting a guest three times is rare enough, but this visit stands out for how Chase Dimond, one of the best-known copywriters in email, now writes his newsletter. Voice notes, a running spreadsheet, and a back-and-forth between ChatGPT and Claude get each edition drafted in about 15 minutes, and then AI builds the whole thing inside his ESP. Jay Schwedelson wanted to know if that means AI writes it, and Chase Dimond explains why it doesn’t, starting with one word he refuses to let through.

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Best Moments:

(01:37) Masked opens, AI summaries, and bot clicks have made email harder than ever

(03:30) A hidden link in the email separates bot clicks from real humans

(05:19) Every edition starts with voice notes and a running spreadsheet of ideas

(07:31) Claude builds the finished email inside Omnisend, alt text and compressed images included

(10:54) The word Chase has banned from AI drafts because it gives the game away

(13:09) A text-based AI assistant now drafts Chase’s inbox replies in his own voice