Ask Us ANYTHING!! 💀 Stop Throwing MONEY at Bad Offers & DATING Advice??? | Ep. 493

Do This, NOT That: Marketing Tips with Jay Schwedelson

GURU Media Hub

Business, Marketing, Education, How To, Entrepreneurship

4.9 • 1K Ratings

🗓️ 17 April 2026

⏱️ 11 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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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MASSIVE thank you to our Sponsor, CallRail!

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Start a Free Trial Here: https://www.callrail.com/dothis

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

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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

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

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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

Check out Jay's Instagram: https://www.instagram.com/jayschwedelson/

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

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

Transcript

Click on a timestamp to play from that location

0:00.0	Welcome to Do This, Not That, the podcast from marketers.
0:05.4	We share quick tips, things you can do right now, and then we add a little bit of chaos at the end of every episode.
0:11.6	We also keep it short, like this intro. Let's check it out.
0:16.5	We are back for Ask Us Anything from the Do This, Not That podcast.
0:21.0	And yeah, this is the podcast where we answer ridiculous questions and work questions.
0:25.0	We try to answer one of each.
0:26.6	If you want to submit a question, just go to jswettelson.com.
0:30.0	There's a button that says podcast.
0:31.3	Another one says, ask us anything.
0:32.7	And that's where we get these wild questions.
0:34.8	So let's do the work question first.
0:37.3	We got a question from William in
0:40.4	Brackett's Bill from Atlanta, Georgia. So before we get to your question, William in Brackett's Bill,
0:46.2	I mean, do you walk around? Is that what you say? William in Brackett's Bill. But I never understand how
0:50.5	he got there. You know, like my son's name is Andrew. We call him Drew. If I want to annoy him, I call him Andy. Like, how are our names, not like our names? Like, I'm not even going to go with Richard because this is a family-friendly show, but I know this woman named Margaret, and she tells everyone to call her Peggy. Like, I don't know. Like, how did this happen?
1:11.6	Like, for me, it's annoying the opposite because my name is Jay and people's like, oh, so your real name is Jason. I'm like, no, it's not. No, it's not. It's Jay. Why is that annoying? What am I talking about? I don't know. All right, William in brackets, Bill. What do you got? Jay, we have this offer that we think is really awesome.
1:29.6	We've sent it out to our internal
1:31.5	database. It hasn't done well. We've tried on different social platforms. It hasn't done well,
1:36.6	but we think it's really great. What are we missing? Seriously? What you're missing is your offer's
1:42.8	not great. Okay? Just because you think it's great
1:47.4	doesn't mean it's great. You have to test it. All right. And good move testing it to your
1:53.7	internal database because that should be the database that performs the best. There's a simple rule
	...

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