Do This, NOT That: Marketing Tips with Jay Schwedelson

Ask Us ANYTHING: Secret AI Trick! 200% Increased Engagement! | Ep. 454


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AI sounds like a shortcut until your “great” ideas flop in the wild, and that is exactly what Jay Schwedelson digs into here. He breaks down a simple 100,000 person prompt that quietly flips AI out of generic creative mode and into deeper statistical thinking, then shares what happened when he A/B tested it on subject lines and CTAs. Plus, a surprisingly relatable question about hating phone calls turns into a legit strategy for staying connected without awkward calls or endless text threads.

Best Moments:

(01:00) Alyssa from Denver asks why AI generated ideas keep underperforming, and Jay flags the hidden problem with how most of us prompt these tools.

(01:47) Jay introduces the 100,000 person prompt and shows how to ask AI to simulate huge audiences reacting to subject lines, landing pages, and offers.

(03:05) Jay explains how framing prompts around 100,000 real people forces AI out of pure creativity and into deeper statistical mode for sharper recommendations.

(03:45) Jay shares A/B test results where 100,000 person prompts beat generic AI suggestions over 70 percent of the time and even double click throughs on CTA buttons.

(05:15) Jared from Dallas admits he hates phone calls and finds texting shallow, and Jay gets real about how easy it is to drift into isolation.

(06:00) Jay reveals his go to solution of voice memos as a low pressure, high connection way to maintain relationships without live calls or walls of text.

Prompts mentioned:

  • Predict how 100,000 real subscribers would respond to each of these subject lines, rank them by expected open rate, and explain the psychology.
  • Evaluate this hero section as if 100,000 new visitors landed on this landing page. Identify confusion points and drop-off risks.
  • How would 100,000 consumer buyers or 100,000 B2B buyers interpret this offer? What is confusing, what is strong, and what is missing?
  • We want you to simulate 100,000 people interacting with this call-to-action button. What should the language be?

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/

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

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