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

17 Apr 2026 · 11 min · 2 chapters

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In short

Marketing Q&A plus rapid-fire dating advice. Work question: a marketer’s offer “isn’t doing well” despite internal and social testing; host argues the offer itself is likely weak and that you shouldn’t “throw more money” at it. Key claim: apply a “100% improvement rule”—ask if doubling performance (e.g., CTR 3% to 6%, conversion 5% to 10%) would make it a winner; if not, redesign the offer rather than optimize.

Notable examples

internal database testing; CTR/conversion hypothetical math.

Guests

none mentioned; it’s hosted by Jay Schwedelson answering questions from listeners (e.g., William “Bill” from Atlanta). Dating segment: Venmo after a bad date (host finds it “amazing” but not sure it’s wise), vacation timing, exclusivity doubts as a red flag, asking “what are you looking for” on date one as “weird,” and Googling someone before the first date.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Evaluating Your Marketing Offer

0:45 to 4:38

Strategies to assess and improve your marketing offers for better performance.

“The opposite because my name is Jay and people are like, oh, so your real name is Jason.”

Ridiculous Dating Advice Segment

5:20 to 10:38

Humorous insights and advice on dating questions submitted by listeners.

“So let's get into the ridiculous portion of this podcast.”
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Transcript

Automatic transcript. May contain errors.

0:01Welcome to Do This, Not That, the podcast for marketers. 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. We also keep it short, like this intro. Let's check it out. We are back for Ask Us Anything from the Do This, Not That podcast. And yeah, this is the podcast where we answer ridiculous questions and work questions. We try to answer one of each. If you want to submit a question, just go to jschwedelson.com. There's a button that says podcast. Another one says Ask Us Anything. And that's where we get these wild questions. So let's do the work question first.

0:37We got a question from William in brackets Bill from Atlanta, Georgia. so before we get to your question william in brackets bill i mean do you walk around is that what you say william in brackets bill but i i never understand how 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 gonna go with richard because it's 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? Like for me, it's annoying.

1:12The opposite because my name is Jay and people are 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? Um, Jay, we have this offer that we think is really awesome. We've sent it out to our internal database. It hasn't done well. We've tried on different social platforms. It hasn't done well, but we think it's really great. What are we missing? Seriously? What you're missing is your offer is not great. Okay. Just because you think it's great doesn't mean it's great.

1:49You have to test it. All right. And good move testing it to your internal database because that should be the database that performs the best. There's a simple rule that I live by with any offer, working with any client of any kind, business, consumer, you name it. And they'll come to us and say, hey, this thing's not doing well. Can you help us make it do better? And I'm like, oh, it's not doing well. You want me to help you to make it do better? And I always ask one question, which is, okay, so right now I'm making this up. Let's say their big thing was the click-through rate on something. Their click-through rate right now is, you know, 3%, right?

2:32If I said to them, what I normally say to them is this, if we increase your performance by a hundred percent, we get that to 6 % click-through rate. Or if it's their conversion rate is only, they're only converting on, you know, 5 % of the people to their landing page. If I get that to 10 % of the people on their landing page, literally a hundred percent increase, whatever your offer is that you think is not doing well, the number one question that you always have to ask yourself is, if we increase the performance by 100%, is that then deemed to be good? Will you then say, this is a winner? Now, why do you need to ask yourself that question?

3:13Why is that always my number one question? Because when you have something that's not performing really that well, the odds of you being able to take that thing that's not performing well and adjust some creative, adjust a little bit of copy, adjust the timing, adjust the social platform or whatever, and you to get more than 100 % increase on performance. The odds of that happening are almost zero, right? You might be able to increase it 20, 30%, 40%, whatever, but increasing something that's not performing well, 100 % is really hard. And if 100 % improvement is not actually going to get you to where it needs to be in terms of performance, then you are wasting your time with that offer.

4:00You need to go back to the drawing board, right? Just because you think an offer is great doesn't mean it's great. You got to test it, okay? And when the offer is not doing well, it's not, oh, let's throw more money at it, right? Because that's going to get it to do well. When something is not good, it's not good. It doesn't need to exist, you can do better. So this idea of the 100 % rule that you want to ask yourself is really important because you're not going to optimize your way to better than 100 % improvement on something that is not performing particularly well. So yeah, that's my answer on the offer.

4:37Before we get to the ridiculous question, I want you to know this podcast is sponsored by CallRail. And you're like, CallRail, I don't need to make phone calls. They gave me ad copy. I'm tell you something call rails about attribution and i'm giving you an offer that you could try it for free they help over 220 000 businesses actually track their attribution everybody knows everyone does last click attribution which is trash tracking stuff from your uh forms on your website calls that are coming in business consumer does not matter if you've never checked out call rail, go to callrail.com slash do this for it's a free trial callrail.com slash do this.

5:17It is awesome for attribution tracking all that. All right. So let's get into the ridiculous portion of this podcast. So the funniest thing about the form on my website, jschwellison.com where people submit questions, um, is that people submit a lot of dating advice questions. I did an episode a few weeks ago when I gave some dating advice based on questions I came in. And then we got inundated with more. And the weird part is, so my team gathered another like five or six of these random dating advice questions, which I will answer. I've not seen them yet. The weird thing is that I am clueless.

5:50You should not listen to me. I know nothing about dating. I've never even opened the dating app, thank God. I've been married for over 22 years to the greatest person of all time. And I'm an old nerd. But you want my answers on your questions, I will give them to you. but is absolutely based in no good information. So here we go. All right. So we're not going to be from any one person. We got these a bunch in from a bunch of different people and I'm going to answer them really quick. And here we go reading them now. Here we go. I said, here we go six times. Great. All right. First one. Is it weird if I Venmo request someone after a bad date?

6:25That is amazing. I have no idea if that's weird. I just hope you do it and then I want to hear about it because that is awesome. I mean, like, what is that? How does that go down? Oh, that was a horrible day. I'm going to tell the person that really wasn't that much fun. I want to get my money. I mean, you probably shouldn't do it, but please do it and then tell me what happens. Okay. Next one. How soon is too soon to go on vacation together? You know, I screwed this up when I was younger. Okay. I was dating somebody for not that long. We went on a vacation together and it was horrendous because I was more into the person than they were into me.

7:01And by day two, it was like, oh no, we're sharing a room. It was super awkward. It was horrendous. Okay. So my advice there is if you want to go on a one night, you know, staycation with somebody that you're early on with, I'm pro, but a multi-night thing, I think you've got to be in it for a while. That's where I land on that. All right. Jay, how do I know if I'm the only one they're talking to? So like, if you need to ask that question yourself, then you're in a bad situation, in my opinion. Meaning like, if you think the person that you're hanging out with could also be talking to somebody else, that means they're not that into you and you're nervous about it.

7:42I don't like that. So I think that's a red flag. If you have to ask yourself, that's not good. That's not good. So I don't know how long or whatever, but don't get out of that. All right, next one. Is it weird to ask someone what they're looking for on date one? 100 % that is total weirdness. Do not do that. You cannot be on date one. You're like 45 minutes into the date and you're like, oh, I like this person. I'm going to now ask them what they're looking for in a long-term relationship. If someone did that to me, I would run away. I'd be like, yo, I barely ate my appetizer. I can't give you my outlook on the rest of life.

8:26That's weird. That is a red flag. That person's probably scary. I don't know. I don't like it. All right, last one. Jay, is it okay to Google someone before the first date? Yeah, hello. You have to do that. Unless you're like going on a date with someone you know. Okay, fine. But if you're being set up, or I don't even know if you go on a dating app, date somebody or whatever. Listen, I was watching Netflix last night and all of the top shows are true crime. Every single one. You need to Google somebody or you're going to wind up on Netflix in a true crime story because there's a lot of weird human beings out there.

9:08And you need to find out if you're about to go on a date with somebody that's going to be a true crime story. By the way, the true crime things are wild. These shows are wild. There's so many of them. I, I, it's just, and they're all, it's just so sad and so terrible. And I don't, I don't know why they're so popular. I watch them. That's why they're so popular. I don't know. Anyway, listen, you'd be awesome if you go to jschwedelson.com. In the upper right-hand corner, there's a button that says partner. I want to collab with your company. I want to promote your stuff. My agency, we're with business, consumer, you name it, big brands, medium-sized brands.

9:43We do all sorts of consulting and media buying and net new and all sorts of stuff. Hit me up. JaySchwedelson.com. You rock. We'll see you at the next one. Later. Wait, the party is not over. Go to JaySchwedelson.com because I want to do stuff with you. I want to partner with you. When you click on the button, partner with Jay, you let me know what you got going on. Work with my agency. Work with me directly. get access to all of my free resources at jschwedelson.com. And I got a book coming out this April. It's called Stupider People Have Done It. And all of the net proceeds are going to the V Foundation for Cancer Research.

10:24Go on Amazon, buy Stupider People Have Done It. That way you can help kick cancer's butt with me. And if this podcast wasn't the worst podcast you've ever listened to, it might have been, leave it a review, follow the show. You are awesome. Go out there and crush it.

From the publisher

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

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