🔥Controversial Email TAKES! Jay vs Jessica Best!!🔥 GUEST!! Jessica Best | Ep. 460

Do This, NOT That: Marketing Tips with Jay Schwedelson

GURU Media Hub

Education, Marketing, How To, Business, Entrepreneurship

4.9 • 1K Ratings

🗓️ 13 February 2026

⏱️ 22 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

If you have ever thought about quitting your agency job to start your own consultancy, Jessica Best has the blueprint on how to actually make it work. She joins Jay Schwedelson to break down why betting on yourself is less scary than staying in a job that drives you crazy. They also get into a heated debate over email marketing hot takes, including why resending to non-openers might be a waste of time and why most A/B tests fail to prove anything useful.

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Connect with Jessica on LinkedIn or visit her website at Jessica.Best

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Best Moments:

(02:00) Why getting mad at your current situation is the best fuel for starting a business

(04:23) The terrifying reality of keeping your sales pipeline full when you work for yourself

(06:30) Jessica argues that resending emails to non-openers is actually a bad strategy

(08:00) Jay reveals his aggressive subject line trick for getting people to open the second time

(10:00) Why testing every single email you send is a terrible idea that drives you crazy

(14:00) The myth of the perfect day and time to send an email campaign

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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

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0:00.0	Welcome to Do This Not That, the podcast from marketers.
0:05.0	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.
0:11.0	We also keep it short, like this intro. Let's check it out.
0:15.0	We are back for Do This, Not That podcast, And we got somebody on the show that I've been,
0:40.2	one, having a show for a long time because I've listened to her, speak on podcasts, all the things. She's a big deal. So who's here? We got Jessica Best. And I want to make some sort of cheesy reference that she's the best. But I'm not going to do that because that's just I would never be cheesy like that. But who is she? She is like it in the world of email marketing. And for more than the last 15 years, all right, she was client side, agency side, all the things, helping some of the
0:46.0	biggest brands on the planet like Dairy Queen and Spirit Airlines and Planet Fitness and Delta
0:50.8	Fawcett and water.org and so many others she has experienced the b2b side the
0:55.9	consumer side nonprofit side when it comes to email marketing she is one of the people that knows
1:00.4	all the secrets all this stuff she was named a 40 under 40 search under journal said she was
1:06.0	top 50 people that are most awesome all these things she is here we're going to break down all things
1:10.6	jessica welcome to the show.
1:12.4	That's one of the best interests I think I've ever had.
1:14.6	Like, you did your homework and I appreciate it.
1:16.9	So thank you.
1:17.9	I'm super excited to be here.
1:19.8	The homework was easy because it's done a lot of stuff.
1:21.8	And, you know, before we get into, we're going to be ripping through some hot takes as
1:25.1	relates to email marketing. But before we do that, you know, a lot of people out there listening, maybe they're a marketing manager or whatever they are. And you've done something I think a lot of people think about, but actually haven't done, which is you said, screw it. I'm not going to work for an agency. I'm not going to work on the client side. I'm not going to work for someone, other business.
1:46.0	I'm going to go out on my own.
1:48.0	And here it is.
1:49.0	We just celebrated your third year anniversary, going out on your own.
1:53.0	How is it going?
	...

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