Do This, NOT That: Marketing Tips with Jay Schwedelson

Partner with Jay: https://www.jayschwedelson.com/contact
ㅤ
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
ㅤ
Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter
ㅤ
Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com
ㅤ
Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com
ㅤ
Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/
Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson
Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/
Ask Jay anything: https://www.jayschwedelson.com/ask
ㅤ
Leave a comment and follow the show, it really helps us out!
ㅤ
MASSIVE thank you to our Sponsor, CallRail!
CallRail is the AI-powered lead intelligence platform that helps marketers prove exactly what’s driving results. With CallRail, you can connect every call, text, chat, and form submission directly to the campaign that generated it so you finally know what’s working and where to double down.
Plus, with built-in AI conversation intelligence, CallRail analyzes your customer conversations, captures leads 24/7, and gives you deeper insights into what your prospects actually care about.
If you’re tired of guessing about your marketing ROI and want real data behind your campaigns, CallRail has you covered.
Start a Free Trial Here: https://www.callrail.com/dothis
ㅤ
Every December, people can’t stop sharing their Spotify Wrapped, and most brands still act like that moment has nothing to do with them. Jay Schwedelson argues that every brand should have its own Wrapped-style content ready, whether it’s a consumer brand, a nonprofit, or a B2B plumbing supplier. He also shares a few email plays that work better in the next six weeks than at any other time of year, plus a reality check on how many people actually let AI agents run their errands.
ㅤ
Best Moments:
(00:27) Why Spotify Wrapped-style content is the format every brand should be prepping right now
(01:58) Brands that launched Wrapped content within five days of Spotify saw over 50% higher engagement
(03:09) Letter format emails to directors and above pull a 28% higher reply rate in early December
(04:07) “Your VIP status is ending” subject lines lift opens by over 40% with non-engaged subscribers
(06:04) Out of 320 million Uber trips and orders, only four rides were booked by an AI agent
(09:27) The 23-year marriage debate over “whup cream” and the word drawer

Partner with Jay: https://www.jayschwedelson.com/contact
ㅤ
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
ㅤ
Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter
ㅤ
Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com
ㅤ
Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com
ㅤ
Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/
Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson
Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/
Ask Jay anything: https://www.jayschwedelson.com/ask
ㅤ
Leave a comment and follow the show, it really helps us out!
ㅤ
Check out the new Bathroom Break podcast with Jay Schwedelson and Daniel Murray on Apple and Spotify.
ㅤ
Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights. Subscribe to Ari Murray’s newsletter at gotomillions.co for sharp, actionable marketing insights.
ㅤ
An Instagram auto-reply that says exactly the wrong thing at exactly the right moment kicks things off, and it only gets messier from there. Jay Schwedelson and Daniel Murray get into why lesser-known holidays might beat Black Friday in the inbox, why every marketer should be poking around personal AI agents right now, and how a routine automation setup got Jay locked out of Instagram. Stick around for a dinner story you won’t be able to unhear.
ㅤ
Best Moments:
(00:21) An automated DM replies “Boom, check your inbox” to a listicles joke, and Jay refuses to delete it
(01:16) Small Business Saturday, Giving Tuesday, and Green Monday can lift open rates over 20% in the subject line
(02:57) Grok Bot, Claude Duet, Dots, and Muse, and why marketers can’t afford to sit these out
(04:19) Why AI summaries could knock the subject line down a peg within a year
(04:59) Jay got blocked on Instagram over ManyChat, and the native tool that fixed it
(07:07) A family dinner ends with a projectile vomit trail through the restaurant

Partner with Jay: https://www.jayschwedelson.com/contact
ㅤ
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
ㅤ
Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter
ㅤ
Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com
ㅤ
Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com
ㅤ
Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/
Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson
Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/
Ask Jay anything: https://www.jayschwedelson.com/ask
ㅤ
Leave a comment and follow the show, it really helps us out!
ㅤ
Catch CEO of Constant Contact Frank Vella's keynote at GURU Conference, the free virtual email marketing event. Register at guruconference.com.
ㅤ
A cold LinkedIn message to a CEO he’d never met ended with Constant Contact acquiring GURU Conference. Jay Schwedelson and Frank Vella retrace how that one note got a reply within an hour and a call within a day, and why the fit felt obvious from the first conversation. Frank also gets candid about who really reads his inbox and where messages from strangers actually get noticed, which is gold for anyone trying to reach a busy executive.
ㅤ
Best Moments:
(01:21) The angry morning after GURU 2025 that led to a cold message to a CEO Jay had never met
(02:54) An hour later Frank replies, and the two are on a call within 24 hours
(05:12) Why the tagline “We’ll make you a better marketer” never sat right with Frank
(09:42) The outreach move that makes a CEO look unresponsive without meaning to
(11:40) Why LinkedIn notifications get seen long before connection requests do
(14:12) Frank’s promise that GURU will never turn into a sales pitch

Partner with Jay: https://www.jayschwedelson.com/contact
ㅤ
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
ㅤ
Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter
ㅤ
Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com
ㅤ
Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com
ㅤ
Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/
Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson
Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/
Ask Jay anything: https://www.jayschwedelson.com/ask
ㅤ
Leave a comment and follow the show, it really helps us out!
ㅤ
Your email numbers are about to look broken, and the strange part is that nothing is actually wrong. Jay Schwedelson explains why the stretch between November and mid December plays by its own rules, and why the AI tools reading your emails might stop paying attention halfway down. Plus a reality check on that nagging feeling that your phone is listening, and a turkey jerky story that makes no sense at all.
ㅤ
Best Moments:
(01:12) Consumer unsubscribes jump 260% while opt-ins spike 210%, and both are completely normal
(02:06) Why any offer with 2027 in it gets a 71% bump in consumption right now
(03:17) AI inbox summaries pull almost everything from the first half of your email
(05:27) The FTC’s surprising finding on a product that claimed to hear your conversations
(07:09) A snack in a Theranos documentary turns into an influencer pitch nobody saw coming
(08:28) Paramount gives Scrooge a real Venmo account, and he pays out exactly one penny

Partner with Jay: https://www.jayschwedelson.com/contact
ㅤ
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
ㅤ
Subscribe to Jay's newsletter for weekly marketing tips and tactics: https://www.jayschwedelson.com/newsletter
ㅤ
Register for GuruConference (FREE + VIRTUAL!) https://www.guruconference.com
ㅤ
Check out Eventastic (FREE + VIRTUAL!) https://www.eventastic.com
ㅤ
Connect with Jay on LinkedIn: https://www.linkedin.com/in/schwedelson/
Check out Jay's YouTube channel: https://www.youtube.com/@schwedelson
Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/
Ask Jay anything: https://www.jayschwedelson.com/ask
ㅤ
Leave a comment and follow the show, it really helps us out!
ㅤ
Check out the new Bathroom Break podcast with Jay Schwedelson and Daniel Murray on Apple and Spotify.
ㅤ
Follow Daniel on LinkedIn and check out The Marketing Millennials podcast for sharp, no-fluff marketing insights. Subscribe to Ari Murray’s newsletter at gotomillions.co for sharp, actionable marketing insights.
ㅤ
LinkedIn posts that look almost identical are getting 8,000 impressions one day and 80,000 the next. Instagram has dropped its years of resistance to long-form video. And more inboxes now let AI decide what people actually read. Jay Schwedelson and Daniel Murray work out which of these shifts should change how you market, and they settle once and for all whether bottle service makes you a tool.
ㅤ
Best Moments:
(02:58) Jay stopped liking his own posts from company pages, and reach went up
(06:09) Why Instagram may be a much easier growth play than YouTube
(06:49) How brands can tease a launch and keep viewers on Instagram for the full reveal
(07:49) The first 200 characters of live text are email’s new North Star
(08:50) Image-heavy emails are invisible to AI summaries
(09:32) Why AI agents could make email matter more than ever