5 • 715 Ratings
🗓️ 10 September 2025
⏱️ 12 minutes
🔗️ Recording | iTunes | RSS
🧾️ Download transcript
Convincing your boss to embrace testing isn’t easy, but Jay Schwedelson has a smart way to flip the conversation. Instead of begging to try new subject lines or tactics, he shows how to reframe experiments as an insurance policy against being left behind. Plus, he shares a hilarious story about a supermarket parking lot that’ll make you think twice about where you stand with your shopping cart.
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Best Moments:
(01:00) Josh asks how to convince a CEO to try proven email tactics instead of sticking to personal preference
(02:28) Why creating a 10 percent “laboratory environment” changes the way testing is perceived internally
(03:31) Framing experiments as an “insurance program” to prevent competitors from pulling ahead
(05:26) Using AI prompts to quickly benchmark your marketing against competitors and show executives the gaps
(08:00) Jay debates whether to shop after being dive-bombed by a bird in the parking lot
(09:26) A cart-return showdown in the supermarket lot sparks Jay’s reflection on being a “cart putter backer”
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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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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. |
| 0:16.0 | We are back for Ask Us Anything from the Do This Not That podcast, presented by Marigold. This is where 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. It's go to jswettleson.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. |
| 0:37.8 | People have been submitting audio questions. |
| 0:41.5 | So this week for the first time ever, and we'll see how it all goes, |
| 0:44.7 | we're going to play some of the audio questions that we've gotten in and we're going to try to answer them. |
| 0:49.2 | Ooh, very fancy. |
| 0:51.2 | All right, so let's hear the first question. Hi, Jay. This is Josh. I have a question for you. |
| 0:58.6 | I attended a session. You gave a lot of really great tips on how to boost my emails and my open rates. |
| 1:05.3 | And a lot of these tips I have pitched to my CEO. And she is against all of them. |
| 1:12.6 | And you said something really specific that it's not about what we like or what I like, it's about what works. |
| 1:17.6 | And so how do I convince my CEO that these are the tricks that we should be testing and this is what works? |
| 1:25.6 | And we have to move away from what she likes and what she |
| 1:28.5 | thinks is right. Thanks. |
| 1:31.0 | Josh, that is a great question. How do you win over your boss? How do you win over your |
| 1:37.0 | team when they are totally against trying the new things, the things that you keep hearing |
| 1:42.6 | that are working? And that can be super, |
| 1:44.6 | super frustrating. There's two very specific things that you can do. But before you get into |
| 1:48.6 | the specific things that you can do, you need to have a culture of testing. Whatever it is, |
| 1:53.9 | doesn't even matter if it's email-related, social media, marketing-related, whatever it is, |
| 1:59.9 | if there's not a culture of testing |
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