Skip to main content

In this episode of Do This, Not That, host Jay Schwedelson answers listener questions in an “Ask Us Anything” segment, sharing smart email marketing tactics for win-back campaigns and his current TV picks.

=================================================

Best Moments:

(01:46) Win-back campaigns should start much earlier than one year of inactivity

(02:11) 70% of people who haven’t engaged with emails after 60 days never will again

(03:00) 30-day win-back strategy: value-driven special content

(03:57) 60-day win-back strategy: create FOMO with mistake messaging

(04:33) 90-day win-back strategy: confirmation status emails

(05:41) 120-day win-back strategy: go nuclear with timing and sender changes

(06:17) Sponsor segment: Emma from Marigold email platform

(07:27) TV show recommendations including Paradise, Love Hotel, and House Hunters

=================================================

Check out our 100% FREE + VIRTUAL EVENTS! -> 

EVENTASTIC – The worlds LARGEST event about EVENTS! June 5-6 2025 

Register HERE: https://www.eventastic.com/Registration

Guru Conference – The World’s Largest Virtual EMAIL MARKETING Conference – Nov 6-7! 

Register here: www.GuruConference.com

=================================================

AND Don’t miss out on these awesome FREE upcoming Quick Hits!

WunderKind: 20 Ideas in 40 Mins! Would You Rather?! Topic: Owned Channel Performance SECRETS!

May 8th – Register HERE: https://www.linkedin.com/events/wouldyourather-ownedchannelperf7310021407273304064/theater/

Marigold: May 30th 11am est. More info coming soon!

=================================================

MASSIVE thank you to our Sponsor, Marigold!!

Email chaos across campuses, branches, or chapters? Emma by Marigold lets HQ keep control while local teams send on-brand, on-time messages with ease.

Podcast & GURU listeners: 50 % off your first 3 months with an annual plan (new customers, 10 k-contact minimum, terms apply).

Claim your offer now at jayschwedelson.com/emma.

Transcript

Jay: We are back for ask us anything from the do this, not that Podcast presented by Marigold. This is our short episode where all week long we get in questions, we get in work questions, we get in ridiculous questions, and we try to tackle, I. One of each. And if you wanna submit a question, well, you'd be extremely cool.

Jay: All you do is go to jay schon.com. There's a button that says podcast. Another one. This is ask us anything and we get in wild questions. So let's do the work. Question before the ridiculous question. We got a question from William from Cleveland, Ohio. I. Oh boy, Cleveland Rocks, you know, that's where the, um, rock and Roll Hall of Fame is.

Jay: I always have issues. I have issues with everything. I have an issue with the Rock and Roll Hall of Fame, not through Ass William, because the Rock and Roll Hall of Fame lets in bands and singers that are not worthy. You know, not everybody is, uh, is Guns N Roses on the Beatles? I remember they let in, uh, the zombies who are the zombies.

Jay: They had like two hits in the sixties. Nobody's a fan of the zombies. I'm gonna get so much hate mail. I don't care. Or, how about Percy Sledge? One song when a man loves a woman. You don't get in when you have one song enough. Anyway, sorry. I'm, I get worked up. William, what is your question, Jay? We are, we are starting a win back campaign for contacts in our database who have not opened or clicked on email in over a year.

Jay: It's more than half of our database. Any tips that we should consider? Well, the first tip that you should consider is that you, you've waited way too long. Everybody waits way too long on their win back program. Here's the stat that's gonna make everybody cry out there. This is for your email database, okay?

Jay: 70% of people, whether it's a business or a consumer database, 70% of people that have not opened and clicked on one of your emails after 60 days of, of that, of non-activity, never will. Again, meaning after 60 days passed and the person doesn't open, click on one of your emails. Over 70% of people of that population will never open and click on one of your emails again, the only exception to that rule is if you sell stuff kind of around the holiday season and then people kinda wake back up.

Jay: But beyond that. Business and consumer, you need to have your win back. Programs going way, way sooner. You need to have a win back program starting at 30 days of non-activity, 60 days, 90 days, 120 days. If you're waiting for a year, forget it. A year ago was a, was a million years ago. Nobody cares. So the way that we look at it.

Jay: Is that at 30 days what your win back campaign should be to people that have not opened or clicked on one of your emails should be intense, value driven, uh, special drops to that population of business decision makers or consumers. So what I mean by that is sending them special emails that say things like, three things you missed.

Jay: In the last two weeks. That's your subject line, that's your content. Or in case you missed it, these two, these two things just dropped. You want it to be very intentional about the value that they have missed over those last 30 days, right? And then you could also layer in some fomo. You miss something big, dot, dot dot.

Jay: You are being intentional about telling them in the last 30 days you miss stuff because that 30 day period is where they're starting to get closer to the cliff of never coming back. Then you get this 60 day marker. Then we like to layer in kind of the mistake that uhoh, I think you're making mistake, you've missed out on what we're doing.

Jay: So you start to say things like this and like your subject lines, your body, copy everything. You know, literally your subject line would say, you know, wait, are you still seeing this question mark? Or it might say, you used to love this dot, dot, dot. You have to be all over your contacts that are no longer paying attention to you.

Jay: If you are treating them like everybody else after they haven't engaged for 30 days and then for 60 days you're failing. You're just absolutely failing. And then at 90 days you start to get really aggressive. And this is the time to use the tactic that works better than any other winback tactic that exists for business and consumer targets.

Jay: And that is confirmation status sends. So literally you'd put in the subject line things like this. You'd have the word confirmation written in all capital letters with a colon, it would say confirmation colon, VIP, status ending. Or on the business side you might say. Are you still in? And then you put the industry, are you still in the retail industry?

Jay: Question mark. You are asking the person to basically confirm, not actually confirm, but just by opening up the email and clicking on the email and engaging that they're confirming that they are still, you know, interested in that VIP status. They are still in that industry. Uh, and when they open up you go.

Jay: Okay, great. You're still interested in the VIP status. Great. We have a special deal for you. Okay, great. You opened up the email, you're still in the retail industry. Great. Here's some stuff going on in the retail industry. Confirmation status. Emails kind of freak people out a little bit, but it's the number one driver to doing a a, a, an aggressive win back that actually does really, really well.

Jay: And then when you get to 120 days, you basically have lost the person. So now's when you gotta go nuclear, okay? And you have to do things that are completely different. You need to send your emails out at a completely different time of day, okay? You might need to layer in a new, from name, not a different email address, but just changing the from name, from maybe your brand to maybe a person's name like Alyssa from brand.

Jay: Okay? You need to do something. You need to jump up and down. You need to have more coffee because whatever you're doing. Is not working. So Winback doesn't start at a year, it starts at 30 days. Alright, before we get to the ridiculous question, I want you to know that this podcast is presented by Emma from Marigold.

Jay: Now I use this platform to send out my emails. I've been using this platform for years. I send out billions of emails, consumer and business emails, and I have an offer only for listeners of this podcast. Emma is an in. Credible sending platform that if you've never looked at it, uh, it is grade four loyalty programs for getting your email in the inbox for all of it.

Jay: For the best type of segmentation, the exclusive offer for listeners here is 50% off your first three months of using it. This is wild. You gotta check that out, 50% off. All you gotta do is take advantage of the offer is go to jay sch welson.com/emma EMA. That's jay sch shettleston.com/emma. Check it out, 50% off.

Jay: Wow. All right. Let's get into the ridiculous question. We got a question in from Jackie for, from, uh, for from, where are you from? Fer, Andina Beach, Florida. What is that? I live in Florida for 30 years. What is that? Fer, Andina Beach. I have no idea where that is. I'm probably gonna more hate mail. I should probably go there, but I hope it's nice there.

Jay: How do you live in a state and never heard of something? I'm an idiot. Whatever. Alright, what's your question, Jackie? The ridiculous question, Jay. How can you not be watching the best show on TV? Paradise? Aha. Well, I am watching, I did watch Paradise. First of all, I'm gonna give you a rundown on what I'm watching right now.

Jay: Not because anybody cares, but because I don't know why. Um, paradise if you haven't seen it. Okay, great question. Jackie. I'm glad you brought this up. This is on Hulu. The guy that stars in it. Sterling Hay Brown is awesome if you've not tried it. This is kinda like, uh, dystopian type stuff, like the end of the world type stuff.

Jay: This is a great. Great show and it's been renewed for season two, so if you haven't watched it, watch that I'm watching right now, which nobody else, I was watching it last night, my wife and we, I was sitting on the couch with her. I turned to her. I go. I don't think anybody else in the entire country is watching this show but us.

Jay: And she goes, I think you're right. We're watching Love Hotel on Peacock, which is so good. It's a reality dating show. It's with the, uh, some of the all-star cast from The Real Housewives and they're dating all these dudes and it is a great. Reality dating show that's on Peacock. I've also started watching Four Seasons with, uh, um, uh, what's her name?

Jay: Oh, what's her name? Amy PO's friend. Oh, I, why do I forget her name? Uh, but, and, and Steve Carell from, um, the Office. What, uh, why am I a doofus? I can't remember anybody's name. Uh, and she was in, uh, mean Girls. I can't remember her name. Who cares? Anyway, four Seasons. It's okay. It's mildly depressing. I don't know if I recommend watching this show.

Jay: I don't even know if I want to continue watching the show. I just finished episode uh two. It's fine. And then the other thing we've been watching more of, Lily, I don't know why, is House Hunters. I don't know why I'm watching House Hunters. House Hunters is the strangest show. Everybody's watched House hunters like 400 seasons of it.

Jay: But it's, it's the strangest thing because the couple never is on the same page, right? They're like, okay, uh, we need a new house. And one person's gonna be like, well, I want like a sleek, you know, modern condo townhouse thing or whatever. And the other person's like, well, I wanna a log cabin in the forest with no electricity.

Jay: And I'm like. How do these people wind up together? They're not on the same page and the dude never wins. Uh uh, the wife or or whatever always gets wins and they look at three houses and then you try to guess which one they're gonna pick. And they never pick the one that they should pick. They pick the worst option possible.

Jay: So I don't even understand what really goes. I need to get behind the scenes on house hunters because I've watched like 400 episodes. I would say my ability to pick which one they're going to pick. Is at like a, a, a 19%. I'm terrible at it. Anyway, what am I talking about? I have no, I have absolutely, uh, no idea.

Jay: So thanks for being here. I appreciate you. If you leave this thing a review, you would be really cool human being. I would really appreciate it. It actually helps circulate this show and, uh, check out the next one later.

Leave a Reply