SPECIAL GUEST!! #1 RANKED Email Marketer, CHASE DIMOND 🤖 The 15-Minute Newsletter Built by Two AIs | Ep. 583

Jay: We are back for Do This, Not That, and I am a big deal. I’ve never had a guest on three times. It has not happened. First time ever.

Now, you know this guy is important if he’s on three times. So who’s here? Chase Dimond is here. If you do anything in the world of email, you know who Chase is.

He’s unavoidable. First of all, his business is out of control. All right? They’ve generated more than two hundred million dollars in email revenue for clients.

They’ve sent over, he sent over a billion emails for people, and the guy is a total beast. He has probably, not probably, he has the single largest following for anybody in the world of email marketing on social media. I mean, hundreds of thousands of followers, over four hundred thousand people on LinkedIn, over a hundred and fifty thousand on X, over a hundred thousand newsletter subscribers. He’s everywhere.

I’ve learned so much from him. And today, we’re gonna be talking about AI and email, and Chase, you are the GOAT. Thanks for being here, my guy Chase: Thanks for having me. I forgot this is my third time.

I, I hope I deliver. This is amazing Jay: Be like, um, why am I here again? No, seriously. So let’s jump right into it.

Um, first off, before we get into AI and your email newsletters and stuff, you’re sitting right there at the epicenter of email, especially in the world of direct-to-consumer email and all that. How has email marketing changed in the last year or two years? Chase: I mean, for one, it’s gotten so much harder. I feel like email was so slow to change, probably for the better for so long, and then I feel like so much has changed in the past couple years, right?

Everything from, like, open rates basically being masked to now, like, AI is trying to summarize and categorize emails, and they’re basically reading it what you s- what you said, and then they’re kind of basically digesting it and saying something different for you. So I feel like it’s been chaotic, dude. Um, there’s - E- especially in B2B, like click rates are just absurd. There’s so many bot clicks now.

I feel like it is a hot mess. It’s kind of a dumpster fire, for lack of a better word. It’s hard Jay: So wait a minute, this is depressing. Does that mean we should, you know, that’s it, email’s over from a marketing perspective?

We shouldn’t put our energy there? Or does it matter we should be sending more because there’s so much garbage out there? What is the simple path that Chase is recommending to people in the email space? Chase: Yeah, and I guess that was a little pessimistic.

That being said, right, like I want to empathize that it is hard, and B, I guess the solution, right, is, is a number of things. Like in the day of age of AI and all these types of things, the best way to do it is to send more, but more specific, more targeted, more segmented, right? I think the issue before was it was so much work to create an email that you just created one email for anyone and everyone, you press send, and you’re kind of on your way. Now, right, it is so easy to take kind of that email that you wanted to send to most people and just kind of slice and personalize and make it way more specific, and then you can go send an email to a group of 100 people.

Whereas before, it would just be so much work to send to a group to 100 people that you would just ignore those folks, and you would just include them in the, the 10,000 or the 100,000-person send. So that’s, uh, f- for, for one. Um, number two, right, is like I think you have to be more data-minded. I think everyone just went off of gut and hope and feelings.

Now it, it, it is about the data, and the data does get a little bit muddier, so it is a little bit more difficult with opens being inflated. You know, in B2B, like I mentioned before, click rates are kind of through the roof. So we do kind of like a bunch of, I don’t wanna say sneaky things, but a bunch of clever things around like just including kind of hidden links within the email, and if people are clicking those, then we’re segmenting those as like bot clicks, right? So we’re just doing a lot more kind of strategic, almost like hidden things to be able to understand, like what isn’t a legitimate open?

What’s a legitimate click? Who are the people that are actually buying? And really focusing more on like the behavior more than anything else. Jay: You know, I think the hidden click thing, people are sleeping on that, and you segment- segmenting that, that’s super smart.

And so I do wanna pivot though into your newsletter that you send out. I’m not just saying this ’cause you’re here. It’s one of the few email newsletters that I actually wanna read. I look forward to getting and all of that.

And so I know upcoming at the Guru Conference, which is that virtual free event that I’m involved with, you’re gonna be speaking, and the topic you’re speaking about is how to create your newsletter faster with AI. So can you give us a little bit of behind the scenes? How are you using AI in creating your newsletter? ’Cause your newsletter does not feel like the generic piece of garbage coming out of AI.

Chase: Oh, yeah. Thank you. So for context, I send, uh, three times a week, um, Mondays and Thursdays to talk about email marketing, marketing, copywriting, mostly about e-commerce, but also trying to cater to an audience that is not just e-com focused. And then on Friday, I kinda send this, um, comical series called Alex in My Inbox that is basically my friend that writes this series about kind of a day in his life, but teaching people copywriting through it.

Um, and he actually had been writing that for, I wanna say, like three or four years, and he recently was like, “Dude, I can’t keep doing this every week.” So I replaced him actually with AI and, and no one’s actually, I don’t think, has noticed yet. Um, but essentially, like, my whole thing is, like, I send three newsletters a week. We all see, consume, absorb, kind of digest so much content.

So essentially the, the, the three parts of my content is, uh, number one is I just am obsessed with vo-voice notes. So I’m at my computer. As I see things, I bookmark it, and I basically have, like, a running tab every week where I will send a voice note just saying like, “Okay, pretend Jay has a brand. I got a email from Jay’s brand that sells apparel.

I really, really like how he focused on this specific campaign topic or this specific campaign idea. I love how it’s super timely and super relevant, and I haven’t seen anyone else in my inbox doing it.” So I’ll literally say that type of a thing. I’ll take a screenshot or grab a link or download your email, and then I’ll keep it in this kind of Google Sheet, spreadsheet, whatever.

Um, and then throughout the day, I might be on LinkedIn, and I might notice, oh, someone did this really, really cool influencer drop. I want to figure out why that did so well and how we can replicate that for e-commerce and other industries. So basically, throughout my day, I’m just constantly searching for content. I’m creating voice notes and just keeping tabs.

And then essentially what I’m doing, um, for each edition, each edition I try to focus on four different things that someone could learn in a different bucket of content, email, copywriting and marketing. That way, there’s a little bit of something for everyone, and it’s kinda more fun for me to write ’cause there’s diversity. So what I’ll essentially do is I’ll take that process. I’ll just du-dump that into ChatGPT.

ChatGPT will be like, “Uh, we talked about this thing last week. Don’t do this one,” or, “Organize it this way,” or, “Hey, have you actually seen the campaign from Nike that’s similar to what Jay said? But I think the example is probably better because, um, they did it like this.” So it’s basically me and kinda ChatGPT as, like, my sparring partner going back and forth, and I’m popping voice notes saying, you know, “This is exactly what I wanna say.

Here’s the writing.” And then they’re kind of editing it ’cause sometimes a voice note doesn’t come back perfect. They’ll basically provide me this draft based on what we said. They’ll include the images.

They’ll format it. Then I’ll basically take that, and I’ll go to Claude. And Claude basically will proofread. They’ll kind of do a second opinion.

Um, they’re really trained. They’ll basically help me edit ChatGPT. So they do those. I’ll send those notes back to ChatGPT.

ChatGPT will come up with the next version. I’ll put my notes in. They’ll fix it We’ll edit it, and then it’ll go back to Claude. And eventually, when it’s done, Claude will basically take everything that ChatGPT and I worked on, and it will literally build it within my ESP for me.

So it will do all the formatting, it’ll do all the links, it’ll do all the images. It’ll actually even reduce the image sizes because, you know, you don’t want massive, massive images there. So it will go to Tiny or whatever the platform that you use is, it will upload it there, it will decompress the image, or I guess compress the image so it’s really small and really lightweight. It will do all the alt text.

So Omnisend is my ESP, so it literally will build it all within Omnisend for me. You know, Constant Contact, whoever you use, it will build it within the browser for me. That used to be the most annoying part for me, was like having to then put the subject line, the preview text, then having to go do all the image stuff, the alt text, the, the links. It literally does it for me.

It will screenshot it for me, it will review it on desktop, it will review it on mobile. We’ll pass it to ChatGPT. ChatGPT will then proofread that. So it ki- kind of takes a couple back and forth.

Um, but now I’m at a point where like between my voice notes, the ChatGPT, and the Claude, I can get a newsletter written, edited, and done within like ten to 15 minutes, and then Claude will literally take that and, and build it. And I do it a couple days in advance, so I don’t know how long it takes. Maybe it takes a half hour, hour for Claude to go build it out for me. It is fantastic.

So it is - I’d say it’s probably 75%, 80 me, and then them are kind of editing, p- poking holes at things. Maybe in a given week I only have three ideas, I need a fourth one. It will help me find that fourth one Jay: That’s incredible, and I love the back and forth between ChatGPT and Claude, because I do think people make the mistake of I’m team Claude, team ChatGPT, team Gemini, when really they’re good at different things. Like, is that, is that how you landed there?

Like you like one for something adverse to the other? Chase: Yeah, and I like the way that like I - At this point right now, I like ChatGPT more often than I like Claude, but I think they specialize in different things. Like I love ChatGPT right now for the writing and the image gen. I really love how Claude actually can build it out within Omnisend within my browser.

I feel like that’s so much better than the other alternatives. So yeah, I feel like each one has slight nuances that I prefer, and I wanted to find a way to incorporate both so that way it was a little bit less guess and check on my own part physically Jay: All right, now I got a loaded question for you. If somebody said to me, “Who’s, like, one of the best copywriters that you know?” I would say it’s Chase.

Chase Dimond is, right? And for years I’ve been following your newsletter and a lot of - you do a lot of copywriting tips. Same thing on Silk, a lot of copywriting tips. So here you are, Chase Dimond, master copywriter, and you work with AI to help you write your newsletters.

I know a lot of it’s you, but help you write your newsletters, and it gives you the output. Do you then go back and be like, “Oh no, it put, you know, the word unlock as the start of my subject line,” or it said you have to harness whatever. I would never... That’s a terrible thing.

Or are you just like, you’re trying to move so fast that you just let AI kind of do its thing? Where does Chase land on some of the generic stuff that AI spits back? Chase: Yeah, so I definitely do all the final editing. So essentially the, the last process that I do is once it gets loaded into the ESP, I will then go do like my final revision.

So throughout I’m kind of editing things saying, “No, not this, let’s do that,” rewriting it. And at the very end when it’s actually loaded in the ESP, before I go, you know, test it myself and press send, I am editing things. Like I don’t wanna use the word quietly. I’ve told you a million times not to use the word quietly.

That’s such an AI giveaway. I would never say that in real life. I’m not gonna say it here. Um, so I basically will rewrite it or edit it, you know, at that point now that I’m kind of dialed in, this is...

It, it’s gotten pretty good. It’s not perfect, but it’s gotten pretty good. Um, because I’ve created so much content on the internet and because I’ve been creating content for so long without AI, I literally have scraped thousands and thousands and thousands of my own posts, hundreds and hundreds of my own editions, um, of my newsletter. So it just has so much information that it is quite good.

Um, I would say in a given newsletter, um, I’m probably spending a couple minutes editing. Um, before, right, it used to be so much work. Now it’s pretty dialed. And then at the end of that, what I’ll basically do is I’ll send it, it to myself, the final version.

I’ll double check everything. I’ll export that newsletter as a PDF, and then I’ll upload that back to Claude and ChatGPT and say, “Hey, these are the few edits that I made. You know, make sure that we don’t make those mistakes again.” So obviously every week it presents new mistakes, but it doesn’t typically repeat the mistakes that I’ve corrected in the past.

Jay: All right, that makes me feel better. ’Cause if you were just one of these, you know, copy and paste guys from AI, I’d lose my mind and be like, copywriting is, uh, is over for the universe. All right, I got one last question before we talk about other stuff, which is you probably are one of the most efficient people I’ve ever met in my life. Every time I talk to you, you’re like, “Well, I’m doing these 12 things.

I’m doing - I have this system for this and everything. This takes five minutes, this takes 12 minutes.” And it’s like, I feel like an incompetent dork after I talk, talk to you, right? So I wanna know something.

What is your, like, AI, uh, MarTech stack? Like, what are you using besides for Claude and ChatGPT? Are you like a Wispr Flow guy, a Gamma guy? Like, what are you using Chase: Yeah, that’s a good question.

Um, I, I have my days so focused that, like, it - I just have no point to other than be done. Like, I’ve got two young kids. I know you’ve got kids. I basically work from like eight thirty to three thirty every day.

Most often I don’t do these types of video calls, podcast calls, just because it’s so hard to get work done. Um, so I pretty much have the day mapped out. But yeah, other than Ch-Claude, ChatGPT, I do use Wispr. So when I talk about like just dropping voice notes, I literally hit two, uh, functions on the keyboard, and I just speak.

So I use that as well. Um, I’ve been using... Are you familiar with the AI called Instinct? It’s a kinda a newer one.

Um, so basically what’s cool about that one is it’s all done via text, so it has access to my email, it has access to my types of things. It is now basically like my AI kind of email assistant helping me kind of draft, um, responses within the inbox. So I get a lot of inbound requests for agency work, freelance work, uh, sponsorship. So basically what it’s doing is it’s going through and it’s basically writing drafts because it has access to how I write.

So it’s going writing drafts and then it’ll ping me saying, “The draft for J-for Jay for your speaking opportunity is ready. Do you have any thoughts?” And I’ll be like, “Hey, delete this part, delete that part, press send.” And then it will go send it for me.

So Instinct literally dropping voice notes, texting back and forth with it, helping me manage my email. Um, I’ve been messing a little bit w-around with kind of Grok. Um, I think it’s cool. Not an expert there.

I’ve been messing around a little bit with like Muse. Again, not an expert there, but I like it. Yeah, exactly. So I’d say like the, the staples for me are like Wispr, Claude, ChatGPT, and now Instinct, and then it probably will be a Muse or kind of Grok here soon as well.

Jay: Dude, I don’t get any money from, from Meta for saying this, but Muse is a game changer. I, uh, I, I love it so much. All right, you know what else I love? I love the fact that Chase is going to be speaking at Guru Conference.

Listen, Guru Conference is the world’s largest email marketing event. It is 100% virtual, 100% free, but we, there’s limited spots ’cause they only buy so many virtual seats. And if you wanna see Chase speak, the guy does not speak a lot, okay? But we twisted both of his arms.

He’s gonna be there. He’s gonna be speaking more about AI and your newsletter and how to do all the things. All you gotta do is go to guruconference.com.

Chase, are you fired up to speak at Guru? Chase: I’m stoked. I, I leave my house once a year to go to one event, and I speak at maybe one or two events max. So I think this is probably my third or fourth year speaking at Guru.

What I love is just how fired up the attendees are. The chat’s fired up. You - The number of people that reach out to me after saying thank you and asking questions, it, it makes me really feel good about it. And, and most of the time when you do these types of things, it’s crickets.

There’s no energy. I don’t know if anyone’s on the other side. It is very clear that people that go to this Guru Conference virtually are so engaged and so with it, and that’s why I come back every year. It is just this r- I don’t know how to explain it.

It’s just this feeling of excitement, enthusiasm, and feeling like the work that you actually are sharing makes a difference Jay: Dude, well, it does make a difference, and, uh, you’ve been incredible. I told Chase this before we recorded, but back when I had like 500 connections on LinkedIn, I hit up Chase out of the blue. He had no idea who I was, and I said, “Will you just take a call with me? I wanna pick your brain.

” The guy said yes, and we’ve become good buddies since, and I appreciate the partnership. Everybody go register for Guru Conference and find Chase on all social. His name is Chase and then Dimond, D-I-M-O-N-D. No A.

D-I-M-O-N-D. We’re gonna put it all in the show notes. Uh, Chase, man, you’re a legend. Thanks for being here.