There is something oddly relatable about getting dating advice from a guy who hasn't opened a dating app in over two decades. Jay Schwedelson tackles two very different kinds of questions this episode - one sharp and practical about why your "great" offer is probably not great, and one completely unhinged series of dating questions submitted by listeners who really should know better than to ask him.

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Best Moments:

(01:45) Jay drops the cold truth: if you think your offer is great but results say otherwise, the offer just isn't great

(02:58) The 100% Rule - the single question you should always ask before trying to save a failing campaign

(04:18) Why throwing more money at a bad offer is a trap, and what to do instead

(06:15) Venmo requesting someone after a bad date - Jay's take is exactly what you'd expect

(07:45) Why going on vacation too early in a relationship is a recipe for disaster (he learned this the hard way)

(08:45) The real reason you need to Google someone before a first date, according to Netflix true crime

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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

Zoom became a verb for a reason, but most people are still sleeping on what it can actually do. Kimberly Storin, the CMO of Zoom, joined Jay Schwedelson with a take that might make you rethink your entire webinar strategy - the problem was never the format. It's the death spiral of treating every webinar like a lead machine. There's a smarter way to play it, and it starts with a phrase most marketers have never heard: preference formation.

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Follow Kimberly Storin on LinkedIn for her takes on modern marketing, webinar strategy, and building a brand at scale. Check out Zoom's webinar and virtual events platform if you haven't looked at it beyond the meetings product.

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Best Moments:

(03:34) Why "most webinars deserve to die" is actually about behavior, not the format itself

(06:00) The idea that buying decisions are already made before a prospect ever wants to talk to you - and what that means for your webinars

(12:45) Why segmenting your webinar strategy by audience type is just as important as segmenting your email list

(15:04) The CMO of Zoom just said don't call it a webinar when you're trying to get someone to show up

(17:17) Kim's monthly "table talk" playbook - including the one question she asks every guest that gets 50 CMOs typing in the chat instantly

(18:49) The data point that should change how you think about chat engagement - people who comment go to the pipeline faster

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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 June 9, 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

The data landed this week, and it quietly changes how you should be titling just about everything. Jay Schwedelson unpacks three tactics that are already moving the needle on AI visibility and email open rates, including one that produces what he describes as the most poorly written subject lines imaginable, and it still outperforms. Add in a genuinely spicy Coachella take and some unexpected news from Levi's, and this one earns its 10 minutes.

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Best Moments:

(00:30) Content titles that start with a number are getting picked up by AI overviews nearly 22% of the time, the highest rate of any content type

(01:45) Starting your subject line with "And," "But," or "Plus" is lifting email open rates by around 15%, and yes, it looks as weird as it sounds

(03:00) Comparison-style content like "X vs Y" is showing up in AI answers 45-60% more than other formats

(04:45) Levi's 517 jeans saw a 25% sales spike this quarter, and a JFK Jr. TV show gets partial credit

(05:30) Why Kylie Jenner's cigarette post at Coachella is one 90s trend that should stay buried

(06:00) Jay's full-throated defense of Justin Bieber's Coachella set and why calling it lazy is just wrong

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Big shoutout to our sponsor, Knak!

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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/

ㅤ

Pre-order Jay Schwedelson’s new book, Stupider People Have Done It (out June 9, 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