Conventional advice tells you to always be selling or at least always to be going for the click. Chances are, you hate writing emails, your audience hates reading them and they aren’t making you any money. What if email didn’t suck? What if you enjoyed writing emails that your audience would binge read like they watch Netflix and what if those emails actually made you money? 

In his new book, Email Marketing That Doesn’t Suck, Bobby Klinck will convince you that the old-school rules for email marketing are just plain dumb. He shows you how to do email right, teaching you the five phases of email marketing and how to infuse purpose into your message. You’ll learn to tell a really good story that people want to read but if you have a serious problem with laughing at yourself, if you’re a conversion copywriter or an online marketing guru, you probably shouldn’t read this book.

If the occasional curse word makes you cringe, then this definitely is not the book for you, so consider yourself warned.

Hey Listeners, my name is Drew Applebaum and I’m excited to be here today with Bobby Klinck, author of Email Marketing That Doesn’t Suck: Have Fun Writing Emails Your Subscribers Will Want to Read and That Will Actually Make You Money. Bobby, thank you for joining, welcome to The Author Hour Podcast.

Bobby Klinck: Thanks for having me, Drew. I’m looking forward to this conversation.

Drew Applebaum: Great. Well, why don’t you help us kick it off, can you just give us a brief rundown of your professional background?

Bobby Klinck: I’ll try to be brief, you just handed the mic to a reformed trial lawyer, so I make no guarantees. I am a Harvard Law grad and for the first 15 years or so of my professional career, I had the kind of career that would really make most lawyers drool. I after law school, graduated with honors, worked for a federal court of appeals judge. He was a judge who President Clinton, twice considered appointing to the supreme court. Then I went to work for top flight law firms here in Washington DC, including one where my mentor was this guy at the time, I just called Neil, now I have to refer to him as Supreme Court Justice Neil Gorsuch.

This was the kind of – yeah, this is the world I lived in and then I was a federal prosecutor for a period but the problem was, that kind of what happened was, I was finding myself as I was in my late 30s, kind of not happy and I didn’t know why. I started working with a life coach and this life coach we talked about, relationships and friends and hobbies and all the personal stuff, then, after we’ve been working together, I don’t know, about six months or so, she asked me a simple question: “Do you like what you do for a living?” 

At that point, I had my own law firm, I had hung my shingle and I was doing my thing and I was getting good results but the honest answer was, “No” I didn’t like it and so, I responded that way and then she, being a life coach, she wouldn’t let me just kind of wallow in self-pity. She asked then what I call the ultimate question which is, “Okay, what are we going to do about that?”

At that moment, we chatted about it and she said, “Look, I could see you going on podcasts, going on the radio and advising businesses and entrepreneurs about the legal stuff” and so that was like, “Okay, let me think about that” I got off the phone with her and I think we had calls every two weeks. By the time we got to our next call, I had hired a podcast booking agency to get me booked on I don’t know, 35 or 40 podcasts. I had no offer at that point in this space but I was like, “Why not?”

That’s how I started, that was in 2017 and since then, I no longer actively practice law. I started building an online business, first, it was a business that was around selling legal templates, so I like to say, I sold the most boring thing ever because nobody wants those but they need them and so I had to find ways to be creative and be fun in my marketing. 

Over time, I got to be known, not just as a legal guy but as the email guy and as the guy who could manage to connect with people in a very meaningful way and that led me to where I am now and so now, I’m a business coach who helps people with strategy and especially, I love email but I do way more stuff than that and really helped them with marketing and bring kind of fundamental marketing principles into their online businesses. That’s kind of the arc of my career over the last 20 or so years.

The Personality Behind The Brand

Drew Applebaum: Why was now the time to share these stories in the book? You started this new career, you say it’s a boring product but you were selling it and you’ve seen some success so why put that into a book now?

Bobby Klinck: What it came down to was, my team, I had jokingly asked them, I was saying, “Look, I’m going to write a book. I’m going to write a book. I’m going to write a book” and my team for a long time resisted and honestly, we would kind of do these prioritizations of projects and as we did, honestly, writing a book as much as I loved it, it always kind of came down at the bottom because it was going to be a big project and it was going to be a lot of issues.

Well, we ran a virtual event and this would have been December of 2020 and at the time, we announced some big things including, “I have a free training university called Bomb U where we give away our online courses about marketing” in that and now as we’re recording this, I think they’re 11 or 12 courses in there but it’s ever growing.

We announce that and the outpouring at that event, people were in tears, people were just going nuts and so in the afterglow, I’m smart enough to know the right time to ask my team permission for things, so in the afterglow as I was talking, I talked to my number two, Katie who is in my team, I said, “Hey, can I write my book now?” She said, “Yeah, go eat your cake.” Because we have this joke that she says, I got to eat my vegetables before I can eat my cake.

Drew Applebaum: That’s fair. 

Bobby Klinck: But honestly, I think she thought that it was going to be a book and I don’t want to say sappy but would have been more inspirational and about the idea of creating a surfer’s mentality and being a radical gamer and those kinds of things and I thought about that at first but then I said, “Nah. That’s not the right first book.”

The right first book is the snark-filled book about how to do email right, which is really still my bread and butter of what I think a lot of people enjoy about me is how I do email in a very different way. That’s how we got to that point and then we started writing it and just decided that it was working and we kept going with it ever since.

Drew Applebaum: When you started writing the book, in your mind, who were you writing this book for? Is this for entrepreneurs that are really doing their own marketing, established coms teams, agencies?

Bobby Klinck: So, I mean, I think the book could be used by just about anybody who is – what I like to say, they’re a personality brand and that means, it doesn’t have to be personal brand but there’s personality behind the brand, not a big product company, right? Because the big product company, I don’t know about you but I don’t really care about the personality of Nike or Adidas or anything like that. I mean, that’s just not what drives it. I had in mind, a very specific group. 

Now, the people I’ve traditionally worked with, I call, knowledge brand so there are people who are selling knowledge, knowhow expertise but a software company or some other folks like that could use it too. I had that in mind but really, I was thinking mainly about the people who struggle with email and they know they’re supposed to be doing it but it just feels like one of the things that they’re just checking the box on, because, writing the emails really sucks for them and then, they know that their audience doesn’t really want to read these crappy emails they’re sending and it’s not driving any revenue in their business.

I was trying to help people understand, email doesn’t have to be that way, you can use email marketing to build these connections that just make life more fun, and you’ll enjoy doing it, your audience will enjoy receiving the emails and then on top of that, it will start making you money. That was really the audience. Now, again, I had some friends since then who have businesses where they have teams and they’re buying it for their teams, and they want to do that. I really had in mind, the people who are doing it themselves as the first audience but give advice that could be used by a team as well.

Drew Applebaum: So, it’s a funny question to ask but, how do emails suck? What makes certain emails suck, what makes certain emails shine and can you think of an example recently as something you’ve gotten in your email, whether it was a subject line that you immediately deleted or something you opened up and you’re like, “I wish I didn’t do that.”

Why Do Emails Suck? 

Bobby Klinck: So, the thing that makes email suck, I mean, separate from it not being fun for you is, there’s a couple of problems with it. Number one, they’re boring. So many emails are just boring and that’s it. I mean, there’s nothing to it, there’s no reason why I would want to read it and the typical example of this is a person who has heard the advice, “Hey, I’m supposed to create new content each week as part of my content marketing and then I’m supposed to email my list every week.”

“What I’m going to do is I’m just going to summarize my blog post” or something like that and I like to tell people, “Look, if people wanted the content, they’re going to consume the content.” That’s one thing that people do, because it’s just, check the box. Now, the other thing, the far extreme other end of that is it’s more a practice where suddenly, I’ll start getting emails from people who I haven’t heard from in six months and the reason why is they only ever email me when they’re selling something. 

It’s literally, they only ever email and ask. I like to compare that to, what would you do if you had a friend who, the only time they ever called you is if they were going to ask you to come help them move? Would they be your friend that long?

Drew Applebaum: Right.

Bobby Klinck: No, they wouldn’t. That’s kind of the other thing that makes email suck. I don’t really care how you do things, how you – there’s a lot of ways you could write emails. So for me, I wouldn’t really enjoy inspirational emails but that doesn’t mean that an inspirational email can’t be good, I’m just not the right audience for it. I’m more the demotivational guy who jokes about those types of posters instead of the motivational quotes but that’s not what makes an email good or not, it’s about how you approach email in a first instance that really matters.

Drew Applebaum: Now, you say this in the book so don’t get mad at me but, early on, you sucked at emails too.

Bobby Klinck: Yes.

Drew Applebaum: There’s a really interesting story very early in the book where something happened to you and you wrote an email about the situation and then it all clicked like this was the email that worked. You want to tell me a little bit about that situation?

Bobby Klinck: Yeah, when I was in the online space, in 2017 but really, in 2018 as I was getting going and I was starting to have some success, honestly, selling my legal templates and doing those things but I was doing one of those things that makes email suck. I would send emails each week when my podcast came out that said, “In this week’s episode of…” at the time, it was called the Your Online Genius Podcast, “In this week’s episode of Your Online Genius Podcast, we’re talking about X. When you listen, you’ll learn” bullet, bullet. Again, it was just like that, so that’s what I was doing. 

Then, in August of that year, I went to an event, it was an event where it was all online entrepreneurs, we had all kind of met virtually in a group about six months earlier and we had been in this group, going through an experience together and in the meantime, I had become a lawyer who was helping the person who ran this group, who ran this community and her team.

It was this get together of 400 of my closest friends who I’ve never met in real life until this event. Well, the night before it started, the host had this little event, I mean, it’s not little but it was a hundred or 200 people I guess were there from the attendees and there was this big photo line of people getting in line to go take a picture with her, whatever.

I get in line, I’m just chatting with my new friends then we get to the front and one of her employees, the person that I had been interacting with the most is up there and so, I was like, “I want to take a picture with her just as much as with the host.” So, we take a selfie, then I go, I chat with the host and take a picture. 

Then the rest of the night goes and you know, just kind of becomes a blur of a dinner, drinks, having fun and just enjoying being with these people. Then I get back to my hotel room and the event was in California, I live on the East Coast, it’s about midnight there and I started looking through my phone at the pictures and in that selfie, this team member had taken with me, the main host, this woman, Amy Forterfield, she’s photobombing us with her tongue out in just the most ridiculous expression ever.

I’m sitting there, I don’t want to say I rolled on the floor laughing but almost, I laughed out loud and I’m like, who do I share this with? There’s no one here so I think, just text it to my wife. I do, but of course, it’s 3AM where we live so my wife’s long asleep. I go to sleep, I wake up the next morning, pick up my phone to a notification from my wife that says, “Why are you sending me pictures of you with random women?”

Drew Applebaum: Never good. 

Bobby Klinck: Right and again, because she knew that there was this woman Amy, who I worked with and all of that so she had that sense but it never occurred to me she didn’t know what she looked like. 

She literally just thinks I’m sending her a picture of me having a grand old time with these random women. Later that day at the event, there was a presentation about email and I was talking to one of my new friends and I told her what had happened that morning. She looked at me and she said, “Well, I think we know what your next email has to be” and so I decided there in the moment. 

I was like, “Okay, fine. I’m going to do it” so my next email that I sent out, the subject line was in quotes, “Why are you sending me pictures of you with random women?” and I told the story. The email was primarily the story with just a little call to action about my podcast and the reaction was amazing. The people were blown away, I had multiple people respond, I never had anyone hit reply to an email before. 

I didn’t asked them to hit reply but they were hitting reply and asking me questions. They wanted to talk, they wanted to have this kind of engagement and actually have a conversation with me and as I pointed out in the book, my audience is about 85 to 90% women. The funniest thing is that email got the most responses for men but it was because they thought they’d been hacked. 

When they opened the email they thought that I was asking them, “Why are you sending me pictures of you with random women?” and so it was this funny little thing so that was the shift and then the next week I sent another story based email and it was not anything that funny or uproarious or anything like that but it was another story and after that second email, I got a response from someone, a woman who said: 

“You know, I’ve been on your list for a long time and this is the first time that I feel like you’re a person not a big company and it’s the first time I want to do business with you” and I say that there are a lot of things that I do wrong but one thing I do well is I am very trainable. I’m like Pavlov’s dogs. I hear that, “Hey, this is working and so I leaned in” and I really just started using my emails as a chance to connect with my audience. 

That’s one of the big things I try to get across in the book is that if you’ll use email as a way to connect with people, you’ll find that it will pay off in spades. That’s how you make money with email is it’s this counterintuitive thing. It’s not the sales emails that make me money, it’s all of these weekly emails where I am connecting with my audience that prime the pump so that when I then do go to sell people like, “Hey, if I need what he’s got to sell I’m buying it.” I don’t have to work hard to sell anymore because of that. 

The CATCH Method

Drew Applebaum: You know, breaking down communications with clients and subscribers, I really want to start from the beginning and you talk a lot about in the book about really hooking the audience from email one, their systems probably the most important email and alongside of that, you have a “CATCH” method that you created for readers and listeners to just know how to go about making that email. 

So, I’ll say it not suck, so can you break down the CATCH method and then just talk about why email one is so important? 

Bobby Klinck: Yeah. So I mean, I’ll start with the second part first, why is email one the most important? Because that will have the highest open rate of any email you’ll ever get and in a sense, that’s the first impression and if you don’t make a good first impression, you’re not going to get a second impression for a lot of people. 

They’re gone and so that email is incredibly important and the problem is that so many people use it in a horrible way of just saying because in my audience or in my world, normally someone gets on your list because they signed up for a freebie, a lead magnet of some sort, a checklist, a guide, something like that and so most people send an email that says, “Here’s your thing.” 

I mean it doesn’t literally say that but it literally just says, “Here’s your checklist or here’s your guide” or whatever and that’s about it and I say that’s the biggest wasted opportunity and so instead, you need to do something powerful and before I’d heard people who talk about email say, “Oh that email needs to have feeling” or “It needs to do something more” but no one ever broke down exactly what that meant. 

I am someone [who] like coming up with frameworks and so the catch email framework is just an abbreviation. C is you congratulate them, so you literally say, “Hey, congratulations on grabbing…” signing up or whatever it is and then fill in the blank. 

Then you acknowledge the pain point, so you’re really kind of acknowledging the struggle that they have and the reason you’re doing that is that if you can speak into their pain point and describe it in a way that they say, “Oh, Bobby gets what I’m struggling with” guess what? Subconsciously they’re going to assume, “Hey, if he knows what I am struggling with, he must have the solution” and so it kind of frames you right there as the expert. 

Then after you acknowledge the pain, the T is, “This tells me about you” and essentially I kind of shift by saying, and the essential point is saying them downloading that freebie or joining my list or whatever it is tells me that they’re going to be among the successful people, the people who get past that pain point and so you kind of do that and you explain why in some level, then you have the credibility boost, which is a little bit about you. 

Now, this is not where you put a whole bio, it’s not anything like that but you give them a little bit about you that will make them believe that hey, you are a good person to guide them through it, right? So that is kind of that piece. 

Then the H is for hook. You are going to hook them into wanting to read the next email with a curiosity hook. If for example, my next email in the next sequence was going to be that story of me getting that text from my wife, what I would say the hook would be something like, “And in my next email, I’ll tell you how I managed to stay married even after getting a text from my wife that said, ‘Why are you sending me pictures of you with random women?’” right? 

That’s just like making people say, “I don’t know what his next email is but I got to read it” and so that’s the hook and that’s the structure of that email and if you do that, the point of it is to build trust in that very first email, so that people are then open to getting to kind of know you and figure out whether they like you. 

Drew Applebaum: Now, let’s say you have that first email ready to go but you are working on building a larger funnel and having multiple emails go out in a series, do you wait until you have that whole series figured out until you launch or can you be ready to go and if you think you’ve perfected email launch you just go out of the gates right then? 

Bobby Klinck: I mean again, all of these things are strategy questions that I tell people and in some level, it is kind of how long is it going to take you to get the rest ready but I don’t want people to feel like because I teach people that you have the catch email and then most people will then have what’s called a nurture sequence and then a welcome sequence, which depending on what’s going on in your business that could be between those two sequences, 10, in some cases even 15 emails when you get more advanced. 

I tell people, “Look, I don’t want you to wait” to wait to start building your list and emailing them until it’s all perfect. I’d rather you send that catch email and then start sending them weekly emails if nothing else. 

Now, if you do that, the catch email, you kind of have to take that H off, right? Because you can’t hook them into the next email because you don’t know what it’s going to be necessarily, but other than that, I tell people if you are willing to just do the work and kind of once you get up and running with your basic email sequences, I tell people that look, when you create a new freebie, you just need to understand that there’s some emails you’re going to have to write as part of it and those need to be part of your process where you write the catch email. 

Then for me and my world, I would say a nurture sequence for that freebie and so that could be four or five emails total but if you are willing to put in the work, you can get that done pretty quickly but I know a lot of business owners are perfectionist and so I say, don’t worry about being a perfectionist. Just get it going and just get it out there. 

Drew Applebaum: Now throughout the book, you also have smaller sections, which are aptly named, “Bobby’s Swift Kick in the Ass.” Do you want to tell listeners what readers of the book can find here and why you felt you needed to add these sort of action item sections? 

A Swift Kick in the Ass

Bobby Klinck: Yeah, so what those are and I think that sometimes are Bobby’s swift kicks in the ass and sometimes they’re other random names but you’ll find these like the idea was that I am kind of known as someone who I kind of rant a little bit and I kind of do those things. So those are sometimes something like that, like a kick in the ass where I am telling people to just do something. 

Other times it’s, “Hey, I got to point something out” and an example, an apt example of that is as a lawyer who understands the law and has read FTC, the Federal Trade Commission guidelines, I recognize that the way most people are using testimonials and case studies is actually illegal. If I am going to write a book where I am going to tell you to send some testimonials and case studies, I want to make sure that I tell you, “Oh, by the way but here is what the law is just so you know.” 

I kind of do things like that and then other times, I think there’s at least one where I make a Princess Bride joke reference. They’re just a chance to kind of lighten things up a bit but also tell people what to do or give them things that don’t exactly flow in the series but are kind of an aside but an important aside for you to have. 

Drew Applebaum: What impact do you hope the book will have on a reader and are there any immediate steps that you hope a reader will take either during or after finishing the book? 

Bobby Klinck: I think from my perspective, in a lot of ways what I want people to get out of this is that I want people to understand that email number one isn’t going away. Now, at some point is email marketing going to stop being important? Yes, but people have been predicting email’s death for a long time now and it continues to be the highest ROI of almost every marketing channel, so getting it right is pretty important. 

But at the same time, I really want people more than anything else to just get to the point that it doesn’t seem overwhelming to them, that email doesn’t seem like this huge challenge that they have to undertake to make it work but instead, they can just view it as, “Hey, you know maybe I can get up and have some fun writing emails” and make it that point. I just know a lot of people that I talk to that they tell me that that blinking cursor almost feels like it’s cursing at them. 

You know, it’s just kind of sitting there laughing and, “Ha-ha, you don’t know what to write ha-ha!” and I want people to say it doesn’t have to be that way. Literally, I’m at a point now where I can sit down and write my weekly email in about 10 to 15 minutes and people love it but it’s not going to be that easy to start out but as you do it and kind of build your muscle of doing these things, it can be to the point that sending out an email to your list doesn’t have to be daunting. 

It can just be something you look forward to as a chance to start building that relationship, so that’s what I wanted them to take from the book. Now, what I want them to do is just start doing, start writing and just get an action on this because the sooner you do, the better you’re going to get at it. 

Drew Applebaum: Wow, if you can break down the email creation overthink that is just a huge step in life.

Bobby Klinck: Yeah, that’s right and look, most people, I joke. I have a coaching program, a group coaching program for entrepreneurs and I always joke that I should have – we get shirts every year for them and I feel like I should just get shirts that say, “Overthinkers Anonymous” because that’s the curse of just about everything we do in marketing and especially with email, I just said, “Hey, when you get time…” and there are places where you do have to really think things through like your sales sequences. 

There you have to use conversion, copywriting, you have to think through the stuff in a deeper level but those weekly emails that you are sending out to connect with people, man, they don’t need to be that hard. They need to just be a chance to let them know who you are and give them something that gives some value and to me, the value that I think my emails provide on a weekly basis is give people a smile. If I can give people a smile for a couple of minutes each day, I feel like I’ve done a pretty good job. 

Drew Applebaum: Well Bobby, you know we just touched on the surface of the book here and there is so much more inside the book but just writing this book to really just help folks bring better content to their audience and monetize their email better is no small feat, so congratulations on having your book published. 

Bobby Klinck: Well, thank you. I mean, it was a labor of love and I really like it and you know, I think readers who pick it up are going to enjoy it and they may get a chuckle and just so you know, I like to warn people that if you like perfect grammar, you might not love this book not because it is not edited. It’s edited but there are some split infinitives, there is definitely some dangling participles, there is some changing parts of speech because I viewed it very much as a casual way of having a discussion with people and I wrote it very much like I wrote my emails as a chance to make it not so daunting and so, I hope readers enjoy it and appreciate it. 

Drew Applebaum: Well Bobby, this has been a pleasure and I’m excited for people to check out the book. Everyone, the book is called, Email Marketing That Doesn’t Suck, and you can find it on Amazon. Bobby besides checking out the book, where else can people connect with you? 

Bobby Klinck: You can find me at and Bobby Klinck on all the socials and we actually have a page that has extra resources about email, which is and so you can go there and get more info and find out some things and one other thing that’s worth mentioning, we’re actually as part of the launch doing something special and we’re going to actually have a virtual event at the end of May.

Everybody who buys the book is going to get to go for free and we’re going to have some fun writing emails, so I look forward to connecting with as many people as possible at that event as well. 

Drew Applebaum: Very cool. Bobby, thank you so much for coming on the show today and best of luck with your new book.

Bobby Klinck: Thank you very much.