Summary5 min read

Podcast Episode Summary

Podcast: Do This, NOT That: Marketing Tips with Jay Schwedelson | Presented By Marigold
Episode: Ask Us ANYTHING!! 🧪 How to Convince Your Boss to TEST! ➕ Got Pooped on by a Bird 💩 | Ep. 409
Date: September 10, 2025
Host: Jay Schwedelson
Produced by: GURU Media Hub

Episode Overview

This episode features a dynamic "Ask Us Anything" format, blending sharp, actionable marketing advice with a final, more lighthearted personal story. Jay Schwedelson dives into listener-submitted questions, the highlight being strategies for convincing reluctant bosses to embrace marketing experimentation. Jay details both cultural and tactical steps to foster testing environments within teams, emphasizing the importance of innovation while tying tests to business outcomes. The episode concludes with a humorous story about an unfortunate parking lot experience, keeping the show’s signature informal and relatable tone.

Key Discussion Points & Insights

1. How to Convince Reluctant Bosses to Test New Marketing Ideas

[00:54–13:50]

The Challenge

Listener Josh asks: How do you persuade a CEO who resists new email marketing tactics, insisting on doing things their own way?

Jay's Two-Pronged Solution

A. Create a Culture & Structure for Testing

Highlight broader organizational benefit: The need for a culture of testing is “an overall problem” if missing, but just telling your boss that won’t work (“they're going like, later, dude” – Jay, 01:35).
Establish a “10% Laboratory” environment:
- Propose dedicating 10% of your database/social posts/campaigns for ongoing tests.
- Don't frame as risky testing, but as a 10% insurance program—guarding against being left behind by more innovative competitors.
- “We need this 10% insurance environment.” (Jay, 02:32)
Tie innovation to business concerns:
- Pitch the risk of “profit leakage” if you don’t test and evolve; frame experiments in terms of dollars and lost opportunity.
Emphasize risk mitigation and the small scale:
- “It's only going to 10% [of the audience], and then if you can show traction with that 10%, then you could win.” (Jay, 03:00–03:15)
Measurement is critical:
- Build a dashboard for every test: include the hypothesis, result, lift or fail to make results clear and repeatable.
- Big enough test groups are essential—small, trivial changes (e.g., different “Webinar” subject lines) won’t show meaningful data.
- Suggest bold A/B tests (“Free Webinar” vs. “Three Secrets to Boost ROI”) instead of minor tweaks.

B. Leverage Fear of Competition, Using AI Tools

Highlight what the competition is doing:
- Management responds to the threat of being left behind.
Use modern AI tools (ChatGPT, Claude, etc.) to pull competitive intelligence:
- Prompt examples: “Act as a competitive marketing strategist, compare [My Company] and [Competitors] across digital marketing… Highlight where our brand is falling behind… Make it simple, visual, tactical so a non-marketer executive could grasp the gaps in under two minutes.” (Jay, 05:20–06:43)
“If it’s not even your competition, it’s who you aspire to be, have [AI] give you all this stuff and then you go back and say listen, we need a laboratory environment because this is what our competition is doing.” (Jay, 06:50–07:15)

2. Ridiculous Question Segment: Most Unhinged Parking Lot Incident

[13:52–19:48]

Listener Dana from Long Island asks: “What’s the most unhinged thing you’ve seen in a parking lot?”
- Jay’s relatable story: Recently got pooped on by a bird right before grocery shopping. Debated whether to go in (“I dug in my car while the stuff was, like, kind of dripping on my arm. It was so disgusting... but I said, you know what? I’m going in.” – Jay, 15:23)
Another memorable parking lot moment:
- Witnessed a woman yelling at a man for not returning his shopping cart. Jay reflects on his own cart habits, oscillating between “cart putter-backers” and “non cart putter backers.”
- “I am now back on the cart putter backer team… what percentage of people are on that team? ...I’m going to go with 50%.” (Jay, 18:00)
Invites listener responses on the cart dilemma for fun engagement.

Notable Quotes & Memorable Moments

On pitching testing to leadership: “You want to try to establish a laboratory environment… really what you’re saying is, listen, we’re going to dedicate 90% to what we know works… this 10% ongoing is our insurance against being left behind.” (Jay, 02:09)
On competitive benchmarking using AI: “Act as a competitive marketing strategist…create a side by side table… highlight where our brand is falling behind, where the competitor is aggressive and the easy wins we could implement immediately, keep it simple, visual and tactical so a non marketer executive could grasp the gaps in under two minutes.” (Jay, 05:43)
On parking lot misadventures: “I got out of my car, and a bird took a deuce on me... I debated this for 30 seconds… I found an old, weird napkin, and I wiped it off. And I said, you know what? I’m going in.” (Jay, 15:17)
On the shopping cart debate: “I am now back on the cart putter backer team... Does everybody? Am I just a horrible person? …You gotta pay it forward. Or I don’t know what I’m supposed to do, but she scared me.” (Jay, 18:13)

Key Takeaways

Leadership Buy-in: Cultivate a “laboratory” culture, positioning testing as low-risk, high-value insurance against stagnation.
Pragmatic Framing: Link experiments directly to revenue, profit, and competitive edge to win executive support.
Use of AI for Persuasion: AI-powered competitive analysis can quickly, powerfully illustrate where your company is lagging versus peers.
Bold Testing: Make tests big enough to produce actionable results; minor tweaks rarely move the needle or persuade skeptics.
Keep Things Human: Tie in relatable, offbeat stories to build connection and encourage audience engagement.

Timestamps for Major Segments

| Segment | Timestamp | |-----------------------------------------------|-------------| | Intro & Show Format | 00:01–00:53 | | Listener Q: Convincing Boss to Test | 00:54–13:50 | | Testing Tactics: 10% Laboratory, Framing | 01:30–09:40 | | AI/Competition Benchmarking | 05:18–07:15 | | Ridiculous Q: Parking Lot Stories | 13:52–19:48 | | Takeaways, Call to Action | 19:49–End |

Episode Tone & Style

Upbeat, approachable, and a bit irreverent—Jay balances sharp marketing acumen with relatable anecdotes and plenty of humor. The practical tips are straightforward and actionable, while the personal stories foster a down-to-earth atmosphere.

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Transcript3 lines

[00:01]
A
Welcome 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 presented by Marigold. This were all week long. We get in work questions. We get in ridiculous questions. We try to tackle one of each. And if you want to submit a question, it's real easy. Just go to jschwetelson.com there's a button that says podcast, another one that says ask us anything. We love getting your questions. And now we're getting a little fancy. People have been submitting audio questions. So this week, for the first time ever, and we'll see how it all goes, we're going to play some of the audio questions that we've gotten in and we're going to try to answer them. Ooh, very fancy. All right, so let's hear the first. First question.
[00:55]
B
Hi, Jay, this is Josh. I have a question for you. I attended a session. You gave a lot of really great tips on how to boost my emails and my open rates. And a lot of these tips I have pitched to my CEO and she is against all of them. And you said something really specific, that it's not about what we like or what I like, it's about what works. And so how do I convince my CEO that these are the tricks that we should be testing and this is what works and we have to move away from what she likes and what she thinks is right.
[01:30]
A
Thanks, Josh. That is a great question. How do you win over your boss? How do you win over your team when they are totally against trying the new things, the things that you keep hearing that are working and that can be super, super frustrating. There's two very specific things that you can do. But before we get into the specific things that you can do, you need to have a culture of testing. Whatever it is. Doesn't even matter if it's email related, social media marketing related, whatever it is, if there's not a culture of testing and trying to innovate in the business that you're in, that's an overall problem. Okay? Now that's not going to win the day. If you tell your boss or whoever that they have an overall problem, they're going like, later, dude. So that's not it. So what are the two things that you could actually do to get people to jump on board with this idea of Testing. So the first one is this idea of creating a laboratory environment and you want to win the day not just on a singular test. You don't want to go and say, hey, can we test, you know, putting an emoji in the subject line or something ridiculous like that. No, that is very transactional. That's a one off thing. You want to try to establish a laboratory environment. And what you want to really do is say, we need a 10% laboratory. That's the number. A 10% laboratory where you can take 10% of your database, okay? Or maybe it's 10% of the social media posts or 10% of your email signs, whatever it is, and say with this 10%, this is where we're going to test stuff always and ongoing, right? And you really don't want to pitch internally as this is just for testing. What it really is, it's really an insurance policy, okay? Because a lot of times, you know, bosses or whatever, they don't like testing because it sounds like it's a risk. But when you call your 10% insurance program and basically what you're saying is, listen, we're going to dedicate 90% to what we know works, no doubt about it. But this 10% ongoing is our insurance against being left behind. Our competitors are evolving every single week. We need this 10% insurance environment. And then you really always want to frame it in terms of money, okay? If we're not testing this, this and this, then we may have profit leakage. And that's what bosses care about. They care about money. Okay? Now the other big thing is that you always want to make sure that they realize it's kind of risk free. You're not going to your whole audience, okay? It's only going to 10%. And then if you can show traction that 10%, then you could win. And the showing traction is what's really. You need to go into this with a dashboard that you've created to show how you're going to show whether the test was successful or not. And you want to be able to show in your dashboard, you know, what was the hypothesis about why you were doing the test, what was the result, you know, what was the lift, what was the fail? And the reason you want to create this laboratory environment is there's a really good chance that your test doesn't work. And if you do it transactional, we just want to try this one thing and it doesn't go well, then that's it. You're never gonna be able to do another test again. You need to create this environment, this testing laboratory environment. And when you do do the test, make sure it is big enough. That is absolutely critical. It's a giant mistake to be like, okay, let's test a subject line that says, you know, webinar this Thursday versus this Thursday's webinar. You're going to see a nominal difference. You've got to go bigger to make sure there's a test that has result good or bad in the test. Right? So instead of doing that, you would say something like, let's test free webinar. And you capitalize the word free versus three. Three secrets to boost roi. Two completely radically different things. And that way you can actually see if the results happen. Now what is the second thing that I would do to win over my boss? What is every company in fear of? They're in fear of their competition. So what you want to do is to be able to show what your competition is doing and saying, listen, we're being left behind. They're doing this. And AI is a great thing to be able to tap into what your competition is doing. So you can go in the free version of ChatGPT or Cloud or whatever and you use a prompt like this, okay? You go and you put this prompt in something like this and you say this. Act as a competitive marketing strategist, compare. And then you put your company name and the URL of your company. Compare Acme Company and Acme Company.com and then you put in your competitor or competitors names. You can put five of them in their URLs or whatever across key digital marketing channels and email marketing. And create a side by side table that shows email marketing frequency, subject line styles, social media posting frequency, engagement levels, content types, data collection, use of pop ups, gated content surveys, newsletters, website optimization, CTA is above the fold. All this stuff, okay? And then at the end you say highlight where our brand is falling behind, where the competitor is aggressive and the easy wins. We could implement immediately, keep it simple, visual and tactical so a non marketer executive could grasp the gaps in under two minutes. It doesn't have to be this exact prompt, but something like that, where you're asking AI to go out there, give it the URLs, give it your competition. Okay? And, and if it's not even your competition, it's who you aspire to be, have it give you all this stuff and then you go back and say listen, we need a laboratory environment because this is what our competition is doing. I just need 10% ongoing that I can market To. And this is how you win the day. So. All right, let's get into now the ridiculous question. We always get in ridiculous questions again. We're getting fancy because we have an audio question coming in. So let's hear the audio question. Hi, Jay. This is Dana from Long Island. My question is, what is the most unhinged thing you've seen gone down in a parking lot by Dana? What is up? I appreciate the question. I, too. And from Long Island. Go Jericho. Moved down to Florida when I was 15. I always say I'm from Florida, but be like, no, you're not. I'm like, yes, I am. I don't have that whole New York whatever vibe. But, Dana, let's get into your question. Unhinged things that have happened in parking lots. So, first off, this happened to me just the other day, which was difficult for me to process. I got out of my car, and a bird took a deuce on me. Yeah, bird dropped. I got crapped on by a bird. I don't know how to say it. Hit my shoulder. As I got in my car, I looked at my shoulder. I'm like, what? What? What just happened? And I looked around. Of course, nobody was near me. Nobody cared. And then I was like, do I go into the supermarket and still buy my stuff with knowing I just got, you know, a bird just went to the bathroom on me. And so I debated this for 30 seconds. I dug in my car while the stuff was, like, kind of dripping on my arm. It was so disgusting. And I found an old, weird napkin, and I wiped it off. And I said, you know what? I'm going in. And I went to the supermarket. I got what I needed to get. And the whole time I was thinking about, I have bird duty on my arm. What do I do about this? And then I got home. It was disgusting. Everything about was disgusting. But in terms of unhinged things, I did see a few weeks ago, and I made me nervous. I saw a woman yelling at this dude because he didn't put his cart back. You know, like in a supermarket, like, after you go food shopping, and then you're in the parking area and you have your cart, and then they have those, like, areas where you bring your cart to, like, line them up in that little kind of cart area, whatever. So the dude unpacked his car, and then he just put the cart next to his car, and he was getting into his car, and this woman went crazy. Like, you got to bring your cart back. That's not right. You know, all just screaming and the guy's like, what, what is, what is your deal now? I, I can relate to both sides. No, I would never scream at somebody for bringing their cart back. But, but I then debated in my mind. So I, I, I had a new solution, like two years ago. This is so random. It just popped in my head that I was going to be a person that always brought my cart back when I was in the parking lot, that I was always going to bring my cart back. I was never not going to do it. And for like, I don't know, six months, I did it. Anytime I went shopping at Target or supermarket, whatever, I would take my cart, I would find the little area you're supposed to put your card in. I did it. But then over time, I started to become a non cart putter backer, if that's an official term. And so, but after I saw this woman screaming at the guy go, whoa. I got to get back on the train of putting the cart back because you got to pay it forward. Or I don't know what I'm supposed to do, but she scared me. So I am now back on the card putter backer team. I don't know. Is that like, I wonder what percentage of people are on that team. I'm going to go with just by the sheer volume of carts I see not in that area. I'm going to go with 50%. Everyone that listen, you got to tell me, do you put your cart back? I don't know. Does everybody? Am I just a horrible person meanwhile? Yeah. So that's what goes on. Me. What did we just talk about? I don't know. Listen, I appreciate you. I'm being real. We are running out of our free virtual spots at Guru Conference. It's our large email marketing event. It is free. It is virtual. It is two days. We, we have Nicole Kidman, we have Ann Hanley, we have Amy Porterfield, we have Donald Miller. It is going to be wild. Okay. Guruconverts.com grab a free virtual seat before it runs out. You are awesome. And watch out for them birds in the parking lot later. You did it. You made it to the end. But wait, the party is not over. Listen, I want to keep hanging out. Subscribe to this podcast and if it wasn't the worst podcast you've ever listened to, give it a five star review. Why not? But you know what? I want to do even more with you. Go to gurumediahub.com and we can partner there. You can find out about all of our free events, all of our stuff. And if you're epically bored, go to jschwetelson.com and we could stay connected. You could find my newsletter and everything else I got going on. Thanks for being here and hope you subscribe.