1.5: Eddie Shleyner: Every Conversation Starts with a Good Hook

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This is a podcast episode titled, 1.5: Eddie Shleyner: Every Conversation Starts with a Good Hook. The summary for this episode is: <p>Curiosity, exclusivity, brevity, and promise. These are the four nouns Eddie Shleyner keeps top of mind whenever he writes a subject line. As the founder of VeryGoodCopy.com - a copywriting blog and newsletter boasting some 31,000 subscribers - it's safe to say that Eddie knows a thing or two about how to write a hook that will start a conversation.</p><p><br></p><p>This episode of Conversation Starters focuses on the importance of a good hook. Because whether it's the opening line of a movie, the first sentence in a book, or the first message from a chatbot, those first few words are critical to determining how long your audience engages with your brand.</p><p><br></p><p>Like this episode? We'd love it if you could leave us a ⭐️⭐️⭐️⭐️⭐️⭐️ review! And make sure to subscribe, so you never miss an opportunity to learn more about starting conversations in the Revenue Era.</p><p><br></p><p>You can connect with Sammi, Eddie, and the Drift Podcast Network on Twitter @sammireinstein, @VeryGoodCopy, and @DriftPodcasts.</p>
How Eddie thinks about writing a great subject line
02:01 MIN
How to keep people reading past the subject line
03:43 MIN
The importance of promising value in your content
00:50 MIN

Sammi Reinstein: Hey, this is Sammi Reinstein, and you're listening to Conversation Starters. On this show, we talk all about bringing conversations back to B2B marketing and selling, because if there's one thing we know about doing business in the revenue era, it's that the best customer experience wins. Through the power of our own conversations with Drifters, customers, and special guests, we'll learn how to deliver a sales and marketing experience that puts the buyer first. Let's get into it. Hey, Elizabeth.

Elizabeth: Hey, Sammi. It's been a while since we've been in the studio. What have you been up to?

Sammi Reinstein: I know it has been a while. What have I been up to? Been watching a lot of TV. I love Bravo.

Elizabeth: Bravo? I was going to ask what-

Sammi Reinstein: It's my guilty pleasure, but to balance that-

Elizabeth: You're not the only Drift marketer to say that either. crosstalk It's a big thing.

Sammi Reinstein: I know we have a crosstalk big Bravo fan marketing base. But to balance my Bravo watching, I have been also trying to read.

Elizabeth: Balance is good. Yeah. A little this and that kind of thing.

Sammi Reinstein: Yeah. A little bit of guilty pleasure, and then a little bit of trying to feed my brain. But this book that I'm reading, it's called Seven Husbands of Evelyn Hugo, very popular right now. And I get why it's popular. It really just drags you in from the very start. That first sentence, everything, you're hooked. And I'm glad that it hooks me because I hate when you're reading a book, and it's a hundred pages in and you're like," Wait, where is the part that's actually getting me to continue to read?"

Elizabeth: Yes, I 100% agree with that. There's so many books that people recommend to me and they're like," Just give it a hundred or so pages." And I'm like," That's a lot of my time to hopefully enjoy the book." Which our guest today knows a thing or two about hooking readers from the start.

Sammi Reinstein: Definitely. Today we are interviewing Eddie Shleyner and he knows a thing or two about copy. He runs a website called VeryGoodCopy, which is all tips and tricks on copywriting and marketing and creative. And I'm so excited to get to speak with him today and dive in in how he thinks about writing good copy that sparks conversations. Eddie, thank you so much for coming on Conversation Starters.

Eddie Shleyner: Yeah. Thanks for having me, Sammi. Appreciate it.

Sammi Reinstein: Elizabeth and I were very excited to talk to you. We both are subscribed to your newsletter and very familiar with VeryGoodCopy.

Eddie Shleyner: Wow.

Sammi Reinstein: But I want the listeners to hear from you. Can you give everyone a little bit of background on what you do and a little bit of background on VeryGoodCopy?

Eddie Shleyner: Sure. Well, I'm copywriter and VeryGoodCopy is my blog and newsletter about copywriting and marketing and creativity. And it goes out once a week and there's a lot of cool, smart folks on it from all sorts of industries. Mostly copywriters, marketers, entrepreneurs, various creatives. So yeah, come on by, you could sign up at verygoodcopy. com.

Sammi Reinstein: I definitely recommend signing up. It was also recently nominated for HackerNoon's Email Newsletter of the Year, and that's no easy feat because you were up some really impressive brands like the Morning Brew and the Hustle. So I think it's all very safe to say, that you know how to write a very good email, and an email that makes someone click, an email that starts conversations. So I want to dive a little bit deeper into that, and let's start all the way at the top. So the very first part of that email is the subject line. So how do you think about writing a great subject line?

Eddie Shleyner: Well, so first, I guess, I think about who it's going to, who's the recipient. If it's somebody that knows me and trusts me and appreciates me, like a long time newsletter subscribe, then the subject line doesn't really matter as much as the from line, actually. I think Dave Gerhart talks about this a lot, just the fact that the sender of the email usually has a greater impact on the open rate, when you're emailing warm recipients. But if it's a cold email, then I'm usually doing one of a few things. First of all, you can make them curious. So for example, the subject line I use to promote... What is it? My referral program is," Only for VGC subscribers," I think with a colon and that implies that something's coming. So a few things are at play there, curiosity being one of them. People want to know what's on the other side of the click. So you're opening a loop in the subject line that can only be closed by opening the email. So that's one really clear way to think about it, open a loop in the mind of the reader based on what you know about that person or that group of people, and then make opening the email the only way that they can close the loop. So there's that going on in the subject line. But also I think there's an appeal to exclusivity. It makes people feel special, or like they're on the inside of something. It's also very short, almost incomplete, and that's something Joe Sugarman, who's an excellent copywriter. I study him a lot. He's always suggesting that people do this in their headlines, keep them short, because it's just easier to grab attention, and I guess, get people into the next sentence. And I guess, you could also promise them immediate value. So in my welcome sequence, the subject line is," Welcome. Your six courses and series are inside." And so naturally, there's a pretty compelling promise that you're making to folks so they're going to want to open it and get that value.

Sammi Reinstein: Yeah, Eddie, this is one of those podcasts where I wish I had a notepad and pen with me. I will definitely be going back and listening to this.

Eddie Shleyner: Yeah, good thing it's recorded inaudible.

Sammi Reinstein: Those were so many good tips just within that. I love what you say about it's who and then closing the loop. I am someone, who in my job, I'm building a lot of chatbots and I think that's something that I could definitely take into that, where you have your hook and the only way to close that loop is by clicking in and taking action within there.

Eddie Shleyner: Yeah.

Sammi Reinstein: So, I will certainly take that into my bot building. And just generally that level of exclusivity is something that... Everyone wants to feel special.

Eddie Shleyner: Yeah. It's the fundamentals, but you can never do them too well or know them too well.

Sammi Reinstein: Yeah.

Eddie Shleyner: So, would start there for sure.

Sammi Reinstein: Age old question, I'm kind of curious, from someone who writes so many emails, when you're thinking about the subject line, are you writing your subject line and then letting that inform the body of your email? Or are you writing the body of your email and then letting that inform the subject line?

Eddie Shleyner: So I usually write them first and then I'll write the copy and then I'll circle back and make any changes. Because sometimes you just find a better angle as you're writing it and then that becomes the headline or the subject line or whatever. So there's no hard and fast rule, I think, about when's the best time to write the subject line. In the beginning or at the end, I think as long as you are leading with curiosity and exclusivity and maybe instant gratification, you're doing fine. So you could write in the beginning, like me, write your email and then go back and be like," Oh, maybe I can amend this and ramp up the curiosity here, ramp up the exclusivity," or whatever it is.

Sammi Reinstein: Yeah. We're probably going to talk a lot about Dave in this podcast, but something else I've heard Dave say too, is when you are writing those headlines, write 50, or the subject lines. Just keep going and keep iterating so that's... Write all of those and then let that inform whatever that body is.

Eddie Shleyner: Yeah, for sure. Well, I think, quality comes from quantity. If you write one or two headlines or subject lines, they're probably going to be pretty bad. But if you write 50 or a 100, and you have this enormous selection and you have the benefit of writing all those headlines, the thought processes that went into everything, I think you're going to be able to whittle that down to the best 10% and then whittle that down. So Dave's not wrong.

Sammi Reinstein: Yeah. It's so funny too because when I do go through that exercise, by the end of it, I go back up to the ones I wrote originally and I'm like," Whoa, whoa, whoa, thank God I did this."

Eddie Shleyner: Right.

Sammi Reinstein: "Because these are just not it. These don't cut it."

Eddie Shleyner: Right. It's like on VeryGoodCopy, if I go back to my first articles, oh my God, they're horrible. They're just so cringe worthy. And I think, that's kind of... This is a writing subject lines, writing 50 of them, or a 100 of them, it's kind of like a microcosm of that process of having a blog that you've been writing for years and then you go back and you just can't stand to look at your first pieces. By the time you've written 50 or a 100 subject lines or headlines, you'll go back to ones and you'll have a pretty similar experience. I think, you'll kind of cringe at bad they are.

Sammi Reinstein: Through all of that experience of writing and writing copy, do you have any must haves or must nots, in terms of writing subject lines?

Eddie Shleyner: Well, I guess, a subject line shouldn't be too long. I think that just makes it harder to read, harder to focus on. It'll probably get cut off too. So it shouldn't be too long. It shouldn't have too many emojis. I think emojis are kind of... I don't know, in my opinion, I think they look kind of spammy. And then also, I don't know if a one off email is somebody's going to put an emoji in the subject line. You know what I mean? I feel that's something that a big email blast might have. I think subject line should be short. It's got to be easy to read, it's got to be easy to digest, and just get through and understand. Subject lines should create a curiosity gap so they got inaudible what's inside. I think they should limit punctuation. And this is overlooked, I think, a lot and taken for granted. But every punctuation mark, every comma, every exclamation point, every em dash, it's just another thing the reader has to interpret, and comprehend. So you want to make it as easy as possible to read your writing, and even if it's on a subconscious level, because so much of our decision making happens below the surface. Below our conscious thought. So in general, the easier something is to read, the smoother something is to read, the more likely it's going to get read and acted upon.

Sammi Reinstein: I'm so guilty of the em dash overload.

Eddie Shleyner: Right. I use it a lot too.

Sammi Reinstein: It's become my new thing.

Eddie Shleyner: I use it a lot too. It's just try to avoid using it in your subject lines, I guess.

Sammi Reinstein: Yeah. Yeah. I mean, it's being buyer- reader centric, by making it as easy as possible for someone to be able to read this email.

Eddie Shleyner: Right. Exactly. And by very nature of having an em dash in there, that means that the sentence is just going to be more complex. There's going to be another clause in it. There's going to be something else that has to be read and understood digested. So if you don't have an em dash, then by the very nature of that, you're keeping the message very clean and tight in the subject line.

Sammi Reinstein: Definitely. Okay, Eddie.

Eddie Shleyner: Yeah.

Sammi Reinstein: So, we've gotten someone now to open the email. Right. We've kept it short. We've understood who it's going to. We have made it somewhat curious in that we want to make them close the loop. So I've opened the email, now, how would you get someone to continue reading that email?

Eddie Shleyner: Right. Well, so now, I guess, we're getting into a different, much more broad territory. But I can give you a couple approaches, I guess, ways to think about it. First of all, in direct response copied, there's a concept called the slippery slide. And basically, that's just saying that every element in your copy, the headline, the subject, the subhead, the images, the image captions, the formatting, all of those elements should be working towards one goal and that's to get the reader to read the first sentence. And the goal of the first sentence is to get the reader to read the second and so on and so on until the very bottom until you reach the CTA. So it sounds simplistic, but actually if you put yourself in that mindset of focusing on a single sentence at a time, asking yourself," Is this sentence compelling enough to move the reader into the next sentence?" Then the task of writing becomes much less overwhelming, I think, and much less uncertain because you're making it a smaller and more manageable task. And that decision boils down to appealing to the reader's needs and desires.

Sammi Reinstein: Yeah.

Eddie Shleyner: And actually a good way to think about it is through the lens of the seven deadly sins. So there's gluttony, greed, sloth, envy, rath... How many is that? Five? Pride and lust, right? And if you think about it, these are the things that are really moving people and compelling people. Now, so if you can promise the reader an abundance of something, i. e. gluttony or greed, or if you can make something easier, so sloth, or if you can appeal to ego, so that's envy or pride, or if you can appeal to an intense desire, that's lust, you'll probably keep people reading. So that's one way to think about it, at a very high level, you're trying to appeal to human nature in each sentence you write. And another is by thinking of about emails as a series of elements or links. And you're only as good as your weakest link, or your email is only as good as your weakest link. So for example, many direct response emails have five elements, and each element has a purpose to fulfill or a job, basically. So element number one, is the from line. And the job of the from line is to gain trust and credibility, basically, by presenting familiarity. So either a familiar person or a familiar brand. Element number two is a subject line, which we're talking about, right? And then the job there is to create a curiosity gap or a loop that can only be closed by clicking the email. Element number three is the lead, or the first few sentences of the email. And the job there is just to get read and get you invested in the email because conventional wisdom says that if you read 20% of anything, you'll likely finish it. So the goal of the lead is to be interesting and easy to read, and basically, compelling enough to get folks into the body of the copy. And that's element number four, the body copy, and it should always answer what's in it for me because that's what everybody who's ever read an ad is thinking like," If I keep reading or if I take this action, what's in it for me?" And then element number five is the CTA, the call to action. And that should clearly and concisely tell the reader what to do next. And it should be, I think, as easy as possible to take that next step. So, yeah, so to recap, you should think about each email as a series of elements, and when you drill down into each element into the actual sentences and words to at make each element, you can think about those through the lens of the seven deadly sins and use them to make it as compelling as possible.

Sammi Reinstein: Yeah.

Eddie Shleyner: Sorry, that was a lot. I feel like I just talked forever.

Sammi Reinstein: No, that is a great framework. I literally, internally, was like," Okay, step one." But inaudible I am going to write that framework on a sticky note, put it on my computer, and make sure that I'm thinking about that every time. I also love the, withem, what's in it for me, right? And just always keeping that in mind. Do you think any of those tips or framework change when you change the channel in which you're delivering copy? So we've been talking about an email, do you keep that same framework when you write say a blog, or do you then shift your mindset?

Eddie Shleyner: I think it's really similar, because in theory, it's really just the first thing people see. So if you don't write a good headline your ad, or your article probably won't get read. It's the draw for your content. And I think same goes for subject lines. It's the first thing people see, it's the first thing people read, and if they don't like it, they're not going to open email in theory.

Sammi Reinstein: Yeah.

Eddie Shleyner: So whether you're writing a headline or a subject line, remember, I think, to lead with curiosity, open loops, create intrigue, promise value, promise immediate gratification, right. Make it instant. And if you're doing those things, I think you're doing fine. Yeah.

Sammi Reinstein: You have written in one of your blogs on VeryGoodCopy, that one of the keys to a good headline is the element of surprise. And I thought that was very interesting. And it's sort of what we've been talking about in terms of the loop, but can you give me a little bit more insight into why surprise works?

Eddie Shleyner: Yeah. So surprising headlines basically just captivate the reader and make it more likely that she'll read the next sentence. So I think in that article you're referring to, I cite an example from a newspaper ad from the seventies and the headline was" How to make money with your credit cards." And it was written by Gary Halbert, he was a really famous copywriter, and he wrote it for an ad selling a book called How to Turn Plastic Into Gold. So he was selling a book. And to set up the offer, Halbert grabs the reader's attention with, basically a paradox, basically presenting a statement that appears to contradict itself. So how to make money with your credit cards is outwardly a contradiction because credit cards help us spend money and not make money usually. So it just begs the question how, and that this question compels folks into the next sentence, and that's the goal of the headline. So yeah, it's just using surprise, using a paradox, is really just another way to get people curious, asking how is this possible? Or I thought this was impossible, how does it work? That's how it works.

Sammi Reinstein: Yeah. Finally, Eddie, I'm curious for people listening who might be a sales rep or an SDR or a BDR, and they listened to this and they're thinking about how they can implement it, what is the one thing that you would do in the subject line to grab their attention?

Eddie Shleyner: Well, I think as an SDR, when you're writing to extremely cold prospects, you have to lead with a promise of value. Basically a bribe. One of the biggest mistakes you can make is to ask for something in exchange for nothing, because no nobody's going to take you up on that because why would they. So it goes back to that whole what's in it for me question that's constantly running through people's minds. So as an SDR, you have to look at it from their perspective, from the prospect's point of view, you have to become that person sitting in that seat, reading that subject line, and you have to ask yourself," What's in it for me?" And if you can't answer that question with a clear and compelling benefit, don't send the email. You should always feel confident about the reason you gave people to respond. And I think if you follow that rule of thumb, your open rates will go up.

Sammi Reinstein: Awesome. Eddie, thank you so much for coming on the podcast. Again, I'm going to re- listen to this right when we get off, take a bunch of notes, and implement all of this into my writing. I think it's super applicable for marketers and for sales people looking to write better emails that actually create conversations.

Eddie Shleyner: Well, thank you so much for having me, Sammi. I really appreciate it too.

Elizabeth: Well, I had just hit send on email before recording this podcast, and that podcast episode made me really wish I had saved it as a draft.

Sammi Reinstein: I totally agree. As I was talking to Eddie, I was like," Oh, there is at least two emails and a blog that I'm going to get back to right after this and edit and get rid of my em dashes."

Elizabeth: Yeah, you got to tone down on the em dashes, girl. But in the spirit of being succinct, we will keep this outro succinct. I'm really excited for next week because we are getting in the spirit of Valentine's day, which is all about relationships. But don't worry, we're not getting too mushy. We are focusing on the sales and customer success relationship with two of our own Drifters, Trent Mosley and Jacqueline Van.

Sammi Reinstein: Yeah. I'm really excited for this because we talk a lot about the sales and marketing relationship, and we wanted to shine some light on the customer success and sales relationship, because that's really so important to creating a good customer experience and a great kickoff.

Elizabeth: For sure. The life cycle does not end after you sign a deal so I'm really excited to hear what they have to say and talk about Trent's high emoji usage. So make sure to tune in next week. And if you want to see how Sammi's doing with her content copywriting skills, make sure to check out her sales newsletter linked in the show notes. And for more information from Eddie, we're also linking his website in the show notes.

Sammi Reinstein: See you next week. Thanks so much for listening to Conversation Starters. If you like this episode, please leave us a six star review by clicking the link in the show notes, and hit subscribe so you never miss another one. You can connect with me on Twitter at @ sammireinstein and follow all of our shows at @ DriftPodcasts.


Curiosity, exclusivity, brevity, and promise. These are the four nouns Eddie Shleyner keeps top of mind whenever he writes a subject line. As the founder of VeryGoodCopy.com - a copywriting blog and newsletter boasting some 31,000 subscribers - it's safe to say that Eddie knows a thing or two about how to write a hook that will start a conversation.

This episode of Conversation Starters focuses on the importance of a good hook. Because whether it's the opening line of a movie, the first sentence in a book, or the first message from a chatbot, those first few words are critical to determining how long your audience engages with your brand.

The Highlights:

  • (2:53) What is VeryGoodCopy.com?
  • (3:55) How Eddie thinks about writing a great subject line
  • (11:57) How to keep people reading past the subject line
  • (16:14) Email subject lines vs. blog headlines: What’s the difference?
  • (17:16) Using an element of surprise in subject lines
  • (18:58) The importance of promising value in your content

Check out all of Eddie's copywriting tips at https://www.verygoodcopy.com/.

Learn more sales and marketing tips from Sammi at https://now.drift.com/drift-sales-tips.

Like this episode? Let us know by leaving a review!

Today's Host

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Sammi Reinstein

|Product Education Marketing Manager

Today's Guests

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Eddie Shleyner

|Founder, VeryGoodCopy