TCC Podcast 10: Daily Emails in 10 Minutes a Day with Ben Settle - The Copywriter Club
TCC Podcast 10: Daily Emails in 10 Minutes a Day with Ben Settle

In the 10th episode of The Copywriter Club Podcast, Kira and Rob talk with “don’t-call-him-an-A-list copywriter” Ben Settle about whether he really works 10 minutes a day, his process for writing the Email Players newsletter, his approach to learning (and a great list of books and courses he recommends) and a whole bunch of other subjects that copywriters can learn from. The audio is a touch fuzzy in parts, but what you’ll take away from this episode more than makes up for it. Click the play button below, or scroll down for a full transcript.

The people and stuff we mentioned on the show:

elBenbo’s Lair
The Copywriter Club Facebook Page
Persuasion Secrets of the World’s Most Charismatic and Influential Villains
Dan Kennedy’s Ultimate Sales Letter
John Carlton’s Kick Ass Secrets of a Marketing Rebel
Start with No by Jim Camp
Breakthrough Advertising by Eugene Schwartz
Ken McCarthy’s Copywriting Clinic
Gary Halbert’s Newsletter
Scott Haines
Gray Bencivenga’s 7 Master Secrets for Copywriters
Matt Furey’s Email Course
Jim Kamp and Michael Senoff Interview
The Boron Letters by Gary Halbert
Paul Hartunian’s Million Dollar Publicity Course
Email Players Newsletter
Parris Lampropolous
Product Launch Formula
Eugene Schwartz talk to Philips Publishing
Bob Bly
Bob Bly Interview with Michael Sennoff
Brian Kurtz
Victoria LaBalme Rock the Room
Ray Edwards
Agora Financial
David Deutch
Beverly Hills 90210
Ben’s Podcast
Jonathan Rivera
Ryan Lee
Ben’s Old Podcast
Dan Meredith
Ben’s Zombie books
Kira’s website
Rob’s website
The Copywriter Club Facebook Group
Intro: Content (for now)
Outro: Gravity

Full Transcript:

KH: What if you could hang out with seriously talented copywriters and other experts, ask them about their successes and failures, their work processes and their habits, then steal an idea or two to inspire your own work? That’s what Rob and I do every week at The Copywriter Club podcast.

RM: You’re invited to join the club for episode 10 as we chat with A-list copywriter Ben Settle about mailing his list every day (or more), pulling in six figures by working ten minutes a day (or less), zombie fiction, and stirring up controversy.

KH: Hey Rob, hey Ben. How’s it going?

RM: Ben.

BS: It is going good. I do have to say one thing, because I gotta keep the record clear on this. I can’t let you guys get away with this.

RM: You’re gonna say you’re not an A-list copywriter.

BS: That’s exactly what I was gonna- I’m not even close to that. Not only am I not in the same league, I’m not even in the same sport as- And I know several of them and I can just tell you, I don’t work as hard as they do. I don’t have their talent either. Anyway, I just wanted to clear that.

RM: For the record, I put that in on purpose knowing that you were going to say that exact thing, because I’ve been on your list long enough to know you don’t talk about yourself that way.

BS: And I gotta give you guys some props on something.

KH: Ooh, all right.

BS: Now, Kira, when you first contacted me and you kind of self-deprecated, you’re like, “Well, the name of our podcast isn’t … that cool.” Something.

KH: Did I say that? Oh no.

BS: But here’s what I think. I think it’s a perfect name because it’s so clear. There is no question what this is about. Like, you’re not trying to get fancy. I actually prefer that, so I wanted to give you guys some-

KH: Sorry Rob. Rob came up with it, so that’s all him.

RM: It’s not nearly as cool as having a lair.

BS: It’s not a lair. A lair is- Are you guys both in there? Are you both in El Benbo’s lair?

RM: We are.

KH: Yeah! I just joined recently.

BS: God. You know, that’s a whole other podcast in and of itself. It’s so crazy.

RM: Exactly. Hopefully after we’re done talking, we’ll still be part of the lair, we won’t be kicked out. But we’ve got some questions. We really want to dig into the real Ben Settle and what goes on in the background.

Ben, my first question for you has to with a lot of the stuff that you talk about in your email list, and in the recent program you did with AWAI where you talk about working ten minutes a day. To me, that sounds a little bit like one of those claims that just can’t possibly be true. I think you must work way more hours than ten minutes a day.

You’ve written four books in the last couple of months. You write the daily emails. You write this 12-page paper newsletter … I think it’s 12 pages … that you send out to your list every month. So, I’m calling bull on the ten minutes a day. Tell us the truth. How do you work? How much do you work?

BS: All right. So, it’s a good question, but if you were really on my list, and really paying attention, you would already know the answer to this. But I’m gonna do it anyway, Rob, because I like you.

RM: I really am on your list. But yeah, let’s do this.

BS: My main thing is my email players’ newsletter. That’s my main thing. It’s not going to be my only main thing soon, but for the last several years, that’s been my main thing.

I get up. I let my dog out first because priorities. I come back in. I get a tall glass of water and I gag down a bunch of health supplements, which I have no idea if they work or not, or just give me the most expensive piss in town. I don’t know. I open the computer up. I write an email to sell email players, and then I’m done. It could be four minutes a day, it could be 15 minutes a day, but generally it doesn’t take me very long. That’s all I have to do.

Now, I will go bonkers, okay? I will go bananas if that’s all I did all day. What am I supposed to do with the rest of my day, you know? That’s when I write novels, I do joint ventures with other stuff, I do podcasts like this. I don’t have to do these things, it’s just fun. But, what I have to do usually only takes me about ten minutes, so in a way you’re right but in a way you’re wrong, like a politician would say.

I mean, I have to do it. I have to pull the goal card on that answer because there’s no way- It is what it is, but I only have to work ten minutes. Sometimes I don’t work at all. I’ll go a whole week without doing anything because I’ll just preload the emails up. When I launched my villains book a few weeks ago, I wrote all those emails on a Thursday. It was 16 or 17 emails, that took me a few hours. And then, I didn’t do anything for a week. I didn’t have to write anything.

I did the math on that and it came out to about ten minutes per email. So, yeah. I stand by my ten-minute work day. I really do.

RM:And if we’re gonna add in the other products, though, things like Copy Slacker, obviously you’re working on these, these are the things that keep you sane. It becomes a product that eventually you sell through your list, through the ten-minute emails. But there’s a lot of things going on in the lair on a daily basis.

BS: Yeah, but I don’t have to do it. I’m in there because it’s freaking pandemonium in there and it’s fun and I’m building this crazy society. I don’t know anyone who’s done with Facebook what we’re doing in there, and it’s not just me. I have some people helping me. Obviously they don’t realize they’re helping me, but they’re helping me. I’m pulling some puppet strings every day. It’s so fun in there that we’ve all started calling it real life in there and everything else is fake life, because so many people spend so much of their time in there.

KH: Can you share a little bit more about what’s happening in there? Because I did just recently join, and it sounds even more intriguing now. What makes it different as far as Facebook groups go?

BS: For one thing, I don’t allow value in there unless I’m doing it. One of my … who I call my “Head B*tch in Charge” vice president Misty, she’s sort of like an unofficial business partner of mine for the last year or so. She does the introduction voice on my podcast. I’ve partnered with her on some other things. She’s always there to help with stuff. My audience loves her, she loves them. She does things like contests and she does these things called Misty Massacres. I’ll give value, she’ll give value, but no one else is allowed to give value. I literally ban people who try to give value when they know better.

That’s one thing that makes it stand out, because that’s all you ever hear from people. “I need value!” Screw value. What we do is we’re plumbing the depths of human psychology in there. We have these things that we call thread holes. This is where our thread starts and suddenly it’s a thousand comments and it takes ten different twists and turns, and usually we’re talking about real life, deep stuff, the way that people think. We’re not trying to; it’s not something you go in, like, “I want to talk about human psychology.” It just comes out. And the few people who understand that are benefiting from this hugely with their copywriting, with their marketing. People who are in there, just involved in this, and they’re not trying to pike anything, they’re not trying to sell anything, are finding their options going up because they’re just interesting people.

I want people to have personality in there, and what most groups do is they encourage value, which just has people swinging their dicks around trying to act like they’re better than everyone. That’s all they have. They don’t have personality, all they have is value. I’ve reversed that. Now, they have to have a personality if they want to participate, or they get ignored. This is a very new thing. I’ve had it planned out in my mind for months, but I really didn’t start executing it until recently when I had more time to play with it and that sort of thing.

That’s one of many, many things. I’m building a world in there. I just wrote about this today, I think, actually, in my email. All my emails are preloaded for a while, I’m not sure if it went out today or not. A big influence of mine was Dungeons & Dragons when I was a kid, you had to build worlds. I’m building an actual world. It has its own language; we literally have our own language, lexicon being built in there. It has its own culture, it has borders. I’m always joking around about my immigration and my wall that’s being paid for by the tears of the people I reject. It’s just, I don’t let everyone in. In fact, I probably reject 70% of people if they don’t fit certain criteria. I’m not even sure how Rob got in there, quite frankly.

RM: I wonder about that too.

BS: Somehow he got past my wall, I don’t know. He’s an illegal immigrant.

KH: Okay, well, this is a selfish question, but as we’re building our club, and we just started the Facebook group for that, we just hit 100 people today, we are trying to add value but we also want it to be our own world. Can we have value and personality and make it interesting and not sickening? Do you have any advice for us based on your experience so far?

BS: Yeah. The “No value” thing is just something I did originally to position myself as something different than my friend Dan Meredith, who’s a genius with Facebook groups. I learned a lot from him. His is all about value. His is all about sharing feelings and all this stuff. I’m the opposite. I’m in there with constant satire and entertainment; you don’t even know if I’m being serious or not.

There’s a girl in there who I call her my main chick. I’ve got side chicks in there, I’ve got main chick in there, I’ve got a booty call in there. And nobody knows if I’m being serious or not. Her dad has been a fan of mine for a very long time and made her read my emails when she was 18 years old, and she’s been reading them for like ten years. So I made her my main chick in there, right? And I made this video for her dad because she asked me to: a Merry Grinchmas video. I basically told her dad in this video I plan to impregnate her and give her my demon seed.

RM: Yikes.

BS: Now, nobody knows if I’m being- You can’t tell. I’m getting private messages. “Ben, are you really?” And that’s the beauty of it. It’s satire and entertainment, which is the future, in my opinion, of marketing, is entertainment. That’s the whole point. It keeps people constantly on their toes, it never gets boring.

That’s my goal with it. Your goal might be completely different, so it depends on your mission and purpose with this, with what your trying to do with your Facebook group. To me, you can get value anywhere. I tell people, “If you want value, go to this group or that group.” I’ll send people to your guys’ group if you want. But I don’t want to do that; I want to have deep, psychological conversations where people don’t even realize they’re involved in this experiment I’m doing, and they love it. And they know what I’m doing, but they don’t know when I’m doing it. So its a whole different thing. It’s six months of just deep thought and trying to figure it out.

With what you guys are doing, whatever your goal is, is to position yourselves as high in the copywriting world or whatever, you’d want to go about it differently. So it really just depends on what you guys want or are trying to achieve.

RM: Yeah, good point. Earlier, I think, this week, you wrote about your 10x rule for reading books. And this seems like a really good idea that I think a lot of people who might be interested, listening to our podcast that maybe aren’t exposed to the way you conduct your business, or are on your list, could really benefit from. Will you talk a little bit about why, when you find a great copywriting book, you read it a minimum of ten times? Why you focus so hard on that and why your not out there looking for new stuff?

BS: Yeah. It’s weird because the only reason I figured this out was because I was so broke when I got started, I couldn’t afford a lot of stuff. I would get a book, and I would do a lot of my homework on it, because literally, buying a $9 book was a big deal for me back then. That’s how completely broke I was. So I would buy something … for example, I think my first book was Dan Kennedy’s  The Ultimate Sales Letter. I read it at least ten times. That’s the only book I had.

And I thought, “Man, I sure am getting a deep knowledge.” I started writing copy and I was getting people who’d been in the business for three or four years, and I’d been in it for three weeks, asking me to critique their stuff. I’m thinking, “Don’t you guys already know this stuff?” But the fact is I just had a deep knowledge of that one thing.

So what I would do is I would make money from one client and I would reinvest that into another, what I would consider very high-quality product. So I think my second part was John Carlton’s “Kick-Ass Copywriting Secrets of a Marketing Rebel.” I went through that probably more than ten times. I would get this deep knowledge base, and over the years when I could afford to buy whatever the hell I wanted, I realized I don’t want all this. Most stuff out there is just crap. Why don’t I read the ten best products, and when I say ten, it could be more than ten, but just generally speaking. I’d rather have the ten best products ten times than 100 mediocre products one time.

I really believe it helped give me a deep foundation. There’s things that, to me, seem very basic, that when I teach it people are awed by it. I’m thinking, “This is basic stuff.” But that’s because they’ve been wasting their time with nonsense instead of just going deep into the really tried and true proven things. That’s the way I look at it.

Right now I’m reading a book called, No: The Only Negotiating System You Need for Work and Home. It’s by the late Jim Camp, who was considered the world’s most feared negotiator when he was alive. Died a couple of years ago. This book, right now I’m on my second reading. I know I’ll read it ten times. It’s so deep, there’s so much going on in it. I’m not just gonna toss this to the side and read somebody else’s book just because, you know, I get people sending me books all the time unsolicited, which kind of annoys me actually. I don’t know what to do with it.

You know what it’s like, and I’m gonna go on a little side-trip here. The last place I lived at in this town called Roseburg, Oregon, which I called the Burgle. They all call it the Burg, I call it the Burgle because it was high crime and stuff there. When I first moved there, I noticed one day a little snake came in under the front door and then the next day this little salamander did. I’m like, “What the hell’s going on?” I opened the door and there’s this cat out there, and I believe the cat was just trying to welcome me to the neighborhood. He’s giving me unsolicited gifts. That’s like what these books are. They’re like snakes and salamanders coming through the door. I didn’t ask for this. I don’t yell at people for it because they’re trying to be nice and everything, but it’s just like, “I gotta figure out what to do with these books” because I hate throwing them out.

Anyway. Ten times is what I do, and it’s worked out pretty good.

RM: So, what’s on the list? You mentioned The Ultimate Sales Letter. You mentioned John Carlton’s class and now Camp’s book No. What else is on that list?

BS: Breakthrough Advertising by Gene Schwartz. I’ve probably gone through that 19 or 20 times. That’s so deep, I read it once a year.

RM: Agreed with that.

BS: Ken McCarthy’s copywriting course. Not a lot of people understand how brilliant that guy is. There’s nothing bright shiny objecty about his course, other than he has a whole section on how to identify social paths, which is actually really fascinating. I wrote the ad for it. He hired me to write the ad for it, so I had to go through it several times. I think I went through it 13 or 14 times, and I just kept imbibing this stuff, and I think it made a huge difference.

Another one would be all the copywriting issues of Gary Halbert’s newsletter. They’re not all found on, I had to buy them. There was this guy named Scott Haynes, who, if you guys know him, he’s actually not doing too good right now. As of today, I believe he’s got like a 25% chance of living. He’s in the hospital, he’s had a stroke on Christmas. But he’s one of the most brilliant copywriters I’ve ever met. I got to hang out with him a couple of times. He was one of Gary Halbert’s only proteges. One of the few. So I guess he had the rights … this was back in 2003. He had the rights to sell just those copywriting issues, and so I bought those and I went through those well over ten times.

There’s probably some other ones I’m not thinking of right now, but that was the foundational stuff. That’s the stuff that I still go through these things. I still go through Breakthrough Advertising once a year. Gary Bencivenga had his $5,000 farewell seminar DVDs. For some sick, OCD reason I actually count through how many times I’ve gone through it, it’s like 28 times now. Once a year I go through it and I just keep imbibing stuff.

Matt Field’s original email course, which is really hard to find unless you just talk to him directly. I’ve gone through that probably 20, 30 times. I just go through these things over and over and over. There was this interview- I mentioned Jim Camp. There’s this interview he did with my friend Michael Senoff, which is only like an hour and 20 minutes long. I’ve probably gone through that 40 or 50 times. The Boron Letters is another one. I know I’ve gone through that 30 or 40 times. I actually copied that whole book out by hand, that’s how much I liked it.

Paul Hartunian’s publicity course, How to Get a Million Dollars Worth of Publicity. It’s not a copywriting course, but I learned so much. I’ve gone through that at least 10 or 12 times because I wanted to do publicity, I wanted to master it. The stuff I learned about just tight writing from learning how to write press releases, the way he teaches, has been invaluable for my emails and copywriting. There’s probably more but those are the only ones I can think off the top of my head.

KH: Wow. Well, it’s good to hear that, especially since people listening are like, “Ben Settle has it figured out. He writes great copy.” But you’re in it, and you’re reading this over and over again and revisiting it each year, which is just good to hear. But Ben, I want to ask you about email players. I’m a recent subscriber, I don’t know why it took me so long to finally…

BS: Yeah, what’s with that? Why did it take you so long? What’s going on?

KH: I don’t know! I really don’t know. And I don’t know what finally did it, but anyway. I’m there. When I received my package, I remember thinking … I was blown away, and I also was like, “I wonder how he does this each month?” And I was picturing you putting together these packets and the different colored paper. So, I just want to know more about what happens behind the scenes with the creation of that each month, and how much time goes into it, if you have anybody helping you with it?

BS: Some months it takes me an hour and a half to write an issue, some months it’ll take me four or five hours because … For example, I think your first one was probably the December issue, right?

KH: Yep.

BS: You got the Gene Schwartz call… By the way, those CDs, that’s another thing I went through. Especially the third one, which has Parris Lampropoulos on it. He’s one of my all time favorites. He’s a true A-list copywriter, that’s why I can’t allow myself to be called one. I met that guy and I can’t even hold a candle to the stuff he does. But that third one in that I’ve probably listened to 20 or 30 times, it’s just fascinating.

I don’t normally add big packages like that. That was just kind of a Christmas thing. The January issue will have a bonus in it but it’s just a transcript of a call. Let’s say an issue has a lot of email examples; it’s gonna take me less time to write that. I mean, it’s 16 pages. I purposely keep it at 16 because I have learned over the years that if I give too much information away, people get overwhelmed and they don’t implement, and they just can’t keep up with it. So I purposely keep it limited to 16 pages.

Some issues, like the February issue, assuming you stick around for the February issue, you will read all of my misogynist and sexist- No, I’m just kidding. It’s satire, but it’s very thick. There’s no examples of emails in there. It’s all deep thinking, philosophical stuff about selling and the relationship between the dating world and selling and marketing. That issue took me a lot longer because it’s just wall-to-wall copy. It’s just 16 pages of thick copy. People make fun of me, they’re like, “Ben, don’t you know how to use the return key?” Because they see paragraphs that are like, two pages long.

So that took me longer, so it kind of depends. The inserts I put in there, like I always put a sales pitch for a back-issue, for the most part. A lot of those, I just look back whatever I put in there a year ago and just send that same PDF over, so I don’t even have to make new information for that. It kind of depends. I would say on average it takes me two to three hours to write an issue. That would be on average.

KH: Are you getting ahead a couple of months? You mentioned the February issue. Well, I guess that’s not really that far ahead, but do you have March planned out already as well?

BS: Yeah, I’ve actually just wrote the April issue. Now, I might say I wrote the issue, it’s like 80% done. It’s the first draft: there’s stuff I’ll add to it, there’s stuff I’ll take away. But I like to be ahead because I don’t like- See, I’m like a lot of copywriters, and I’m just not this way. I wish I was, kind of, sometimes. But I’m the guy who had to get his homework done early in high school. I don’t like working under pressure. I like to be relaxed, I like to get everything done early so I don’t have to think about it. I’m always at least three to four months ahead on that.

RM: Ben, I’d love to talk a little bit more about being controversial.

BS: Okay. I’m not that good at it.

RM: I don’t know, you’ve said twice that it’s satire. You’ll call girls “Chicks” and “Dames” which is very un-PC. I’m curious. It feels like this is something that you cultivate in order to make your brand stand out.

BS: I don’t actually try to offend- Like, when I call Kira a dame, I’m not trying to offend her. It’s actually a term of affection. It’s not meant as an insult. People in my world understand that I’m just trying to be entertaining, that’s it. And the fact that people get so wound up, over like- Say that I’m calling people b*tches, you know? Something like that. I’m not calling girls “Hos.” To me it’s fun. It’s old-school, 1940s gangster talk. To me it’s fun.

Now, I mentioned my villains book earlier. One of the chapters is about the Joker. The thing about Joker, he doesn’t have any super powers, yet all the super powered villains and heroes fear him. He’s the scariest dude out there and he’s just this regular guy, you know? Well, why is that? I’m a big comic book fan, and the movies and all that, and I just analyze 13 things that really stood out. I noticed that all these 13 things give him impact.

All I’m trying to do is have impact. If using the word “Dame” or “Chick”- Unfortunately we do live in this mush-cookie society where people get offended by that. I’m gonna use it. I’m gonna use it and I’m gonna give people what I call “The medicine.” I’m gonna give them medicine, I’m gonna show them how to calm down and relax, and have fun, and stop taking life so seriously. Because those are the best kind of customers that I’ve ever had, at least. I don’t like these uptight people. It’s like the old-school southern preacher: I gotta get them lost before I can get them saved.

So I gotta give them the medicine and sometimes that means being this- I just take my personality in real life, which is what you guys are listening to now, I’m not putting a show on or anything. This is just how I talk. And I ratchet it up a couple of notches in my writing. I take the personality and I just add a couple notches of exaggeration to it. Am I saying that everyone should do that? I don’t know. But it works for me, so that’s why I do it.

KH: You talk a lot about fun and I’ve heard you mention fun in a couple other interviews, and I think that’s kind of what gets pulled out of the writing process, especially when you are working with clients. It really … the fun is drained out of it very quickly.

So, how do you keep it fun? I don’t know if there’s a trick to it, but especially, you’ve worked with clients in the past, so I’m just thinking, in the client atmosphere, when you do have that deadline, and it doesn’t feel like fun, what are some ways to shift your perspective?

BS: This is one reason I don’t do client work. I was just helping someone recently. I don’t do a lot of coaching, I was just helping her because we’re friends and all that. She’s only been in this business for six months, and she’s already got a job writing copy for a very well-known- I’m not sure if I’m supposed to name this guy, but let’s just say he’s probably the number one name in direct marketing and has been for 30 years.

She’s got that, right? She’s writing product launch formula style emails for them right now. Now, I don’t know jack about product launch formula, because I just … I don’t know, I never got into it. But, I understand the basics of it. And she’s wisely, wisely making these emails her own, putting her own twist on these things, even though they said, “Just follow the system and write exactly like this, use these swipes.” She’s wisely doing it in her own way. My guess would be, and we’ll find out soon enough, that they will appreciate her more as a result because she’s not backing down to anyone.

When somebody says “Just swipe this,” that’s a terrible goal to have. I think a copywriter has to realize that your client is not necessarily the person writing the check. In fact, I don’t believe that is the client. I think the client is the market. This is something I learned from listening to something over and over, these Eugene Schwartz- He did two talks. One to Rodale Books, and one to Philips Publishing back in the 90s. They’re both excellent. I know I’ve listened to those probably 50 times. I never get tired. I remember him saying, “When you’re writing copy, you have no client except the market.” They’re really the ones that pay the bills, they’re the ones that pay your client, so you have to serve them.

This is going to cause problems with the guy or girl writing the check, in some cases. It just depends. It depends how well you pick your clients. I got really lucky with clients. I make fun of client work, but the reality is I had some really good ones who just- For example, in the self-defense niche, I would write this most violent stuff. I would write copy about “Hit somebody here and he’ll be pissing blood for the next two days.” I would write stuff like that thinking, “Ah, he’s gonna make me”- He would just add to it. He would actually run with it and say, “Wait, let’s make this even more bloody.” That was a cool client.

On the other hand, I had some clients who were really reserved, and they would get really nervous if I would do anything outside of what they considered normal. I would push them even harder. I would push it as far as I could possibly go, and then they could rein it in if they want, and it’s still gonna be better than what they thought. So, my point is that you have to serve the market first. What do they need? Give the market what they want, and always be willing to make your case.

You guys know Bob Bly, I’m sure, right? The great Bob Bly. One of the best copywriters to walk the face of the planet. Him and I have become … I don’t want to say we’re friends, but we’re definitely pen pals. He’s on my daily email list and he’ll write me back a lot and sometimes he’ll agree with me, sometimes he’ll disagree, it’s fine. We just kind of have this banter.

He said something very brilliant once on this interview he did with my friend Michael Senoff. He said, “I can work with clients who are ignorant, and I can work with clients who are arrogant. I cannot work with clients who are both.” An ignorant client is someone who knows they don’t know. They’ve hired you for a reason; they expect you to run with everything, and they want you to, and they’re great. Those are great clients. They’re fine.

You also have arrogant clients who are very talented. They know what they want. They’re kind of pricks, okay? But you’re gonna learn something working for them, because they really do know their market, they know what they’re talking about. They will make you grow, and they will challenge you. I’ve had one client like that once and it was great. I mean, it sucked when I was working for him but now I look back, and I’ve even told him, “Dude, I thought you were a dick, but man, I learned a lot of cool stuff” because he would run and test stuff.

But I can’t work with someone who’s both, someone who doesn’t know they don’t know, you know? Those are the ones I would say you’re kind of in a lost cause with because they think they know but they don’t. You can just grit your teeth and do the work and cry all the way to the bank, I guess, but I would try to turn those types of clients away if I was taking clients.

RM: Ben, I want to change directions again a little bit. I think, if I’m not mistaken, you’ve been in a Mastermind with Brian Kurtz and a really good group of marketers and other writers. You may have been in another one with Ray Edwards, if I remember. I may have heard you talking about something like that in the past. What have those kinds of groups and experiences done for you and your career?

BS: I have to admit something. Brian Kurtz has been trying to get me in his Mastermind group for a year and a half. I love Brian Kurtz; I think he’s one of the most brilliant people I think I’ve ever met, and he’s certainly the classiest person I’ve ever met. I talk to this guy and I feel like such an uncouth jerk here because he’s so cool. That said, I’ve never been in his Mastermind, I spoke at a Mastermind of his a couple months ago, and I told him, “You know, I just hate traveling to these things. The only way I’ll go to one of these is if I’m speaking or training. That’s my rule now.” So I just want to clarify, I’ve never been a member of his Mastermind, but I did attend it. There is some really, really powerful stuff, especially … it wasn’t his Mastermind, it was his Master Class that I went to, actually. I don’t think that’s the same as his actual Mastermind. It was the same thing though.

I’ll tell you what. I don’t usually get a lot when I do go to … I don’t go to them anymore. I’ve been to a couple masterminds and I always get really bored. I get fidgety and, I don’t know, I’m just not into it. But I always walk away with at least one thing, and from Brian Kurtz’s thing, this last one in October. He had a speaker there named Victoria Labalme, who, she teaches TedX speakers how to rock the room. That’s her website,, I think.

Anyway, she gave a talk, and I don’t remember her talk at all except one thing she said. It just stuck with me and I’m pretty sure that’s what she was going for. She just wanted you to walk away with something you’ll remember. She says, “When you’re giving a talk,” and this goes with copywriting, sales letters, emails, videos, whatever you’re doing, it all applies. “When you’re giving a talk, the audience should feel like time has stopped.” I’ll tell you what, that is some of the most valuable advice I’ve ever gotten, and I never would’ve got it had I not gone to that and been invited to speak there.

So, even though I’m kind of a snob about going to Masterminds and all that, I probably should go to them, but I don’t like leaving my dog and all that, so unless I’m speaking I don’t go to them. I was never in Ray Edwards’ Mastermind but he did interview me for his thing he did in the summertime, which was really cool. Him and I have been friends for a long time but I’ve never been in a real- Well, I take that back. I know what you’re saying now.

Ray and I used to be in a real informal Mastermind several years ago with Ryan Healy and John Anghelache, and Daniel Levitz.

RM: Exactly, I remembered Ray talking about that on maybe his podcast.

BS: Yeah, he probably did. Here’s the interesting thing about that Mastermind. There was no pressure. I mean, unfortunately because nobody was paying to be in it, usually we never had quorum, like three of us would show up. But that was fine. One thing I learned from that, and I think this would help copywriters, actually. It really helped me. I learned to not send them copy to critique it. This isn’t because they weren’t brilliant copywriters. They were. But they didn’t understand my market, so the advice they would give I knew was just bullsh*t. Not because they were bullsh*t but because they didn’t know the market.

I learned years ago, from that Mastermind, I would talk about other stuff with them. Business stuff and all that. But as far as critiquing my copy? No. What I would do is send my copy to people who were in the market. It’s funny because I’m not … I had this told to me before that experience by a guy named Doug Deana who’s an A-list copywriter, one of the best of the best out there. You talk about A-list, he’s up there. And I remember him saying, “I don’t do critiques. I can’t critique someone’s ad if I don’t know their market, otherwise I don’t know what I’m telling them.”

That was something I had reinforced at the Mastermind with Ray Edwards. It’s not that those guys weren’t brilliant, they all actually are better copywriters than me. But they never knew the markets I was writing to so they couldn’t … like, they didn’t know the golf market at that time so I’d send them an ad and they’d be giving me advice that I know just isn’t good advice. Not because they aren’t good copywriters, because they just didn’t know the market.

Any copywriters listening to this, which I assume everyone listening to this is a copywriter, take your copy to someone in the market. I’ll give you a real life example. A couple years ago, Agora Financial flew me into Baltimore to teach three things to their editorial and copywriters that were on staff that day. They wanted me to teach email marketing, infotainment, and storytelling.

And somehow, I ended up talking to this copywriter there. I don’t want to name him or anything, not because it’s bad, not because he did anything wrong or anything, but just because he probably doesn’t want me saying anything. Just his own privacy. But him and I got to talking. I was like, “You know, you guys at Agora have the best legal department for writing supplements. Like, I hear you guys have the best.” And I had this ad that was selling a prostate product for people who have prostate problems.

And he goes, “Yeah, we do.” I’m like, “Well, can you give me some pointers on this? Like, how can I avoid getting in trouble with the law, and all that, even on that making claims.” He was like, “Well, let me talk let me take a look at your ad.” So he did, and a few days later I get this long email from him saying, “Ben, I think I have prostate problems.” That was the sales letter. And he’s only in his upper 20s, he does not have prostate problems.

But he was part of that. I didn’t even know he was in the market. But you know, his feedback was invaluable. He didn’t try to critique the copy. He was basically … he bought the product, and then he bought another product that I was selling from that product because of the copy. That’s the kind of feedback that helps me, you know? That’s how I know I was doing right. Now, he wasn’t coming at it from a copywriting point of view, he was coming at it from just a guy. Guys tend to read this prostate copy and they get scared. I put some scary stuff in there. I don’t know if that helps anyone, but I say go to your market for critiques, don’t go to other copywriters.

Unless it’s like technical stuff, then it’s okay. For example, I had that same prostate ad … I was talking to David Deutsch. He’s probably the best direct mail guy out there right now in the game, and him and I’ve known each other for a while. He’s an email player subscriber. And he’s like, “Hey, you know, Ben, let’s get on Skype and just kind of talk once in a while.” So we did. And he looked at my headline and he was like, “God, Ben, this is”- In his own way. He was much nicer about it than he needed to be. Basically said the headline was boring, right? I mean, not in so many words. He was, “I’d like to Ben Settle this thing up a little bit, like you do in your emails.”

That one piece of advice … No, he actually was looking at it from a copywriting point of view, actually was very helpful. And so I changed it and made a much better headline, but that’s because he was he wasn’t trying to critique the whole ad without understanding the market, and all that. That was a technical thing and that was helpful. So you can get good information from really high level copywriters, but, generally speaking, take that to the market. That’s where you get your best feedback.

KH: Ben, that’s a huge help, because I love getting critiqued, but I realize as you’re saying that, that I probably sometimes am asking the wrong people to critique my work. So, yeah, I have to think about that. Ben, I joined your apprentice program. I don’t remember what it was called or if that’s what it was called. A couple of months ago?

BS: Yeah.

KH: Six months ago?

BS: That was in July. Yeah.

KH: July. Okay. July. I have a bunch of questions. Answer whatever you want, but you always mention an ex-apprentice and I really want to know who she is, or he, because you mention her all the time and I’m dying to know. That’s one question.

And then, I just want to hear about how that program, when I know you shut it down and you were really wonderful with your transparency, and I think that’s when I really started to like you, because I thought you handled that so well and so I had a lot of respect for your team. I didn’t know as much about you at the time. That was my first experience. So I want to hear about that process, and then why you never want to do that again. If that’s true.

BS: Okay. No, those are very good question, actually, and I haven’t talked a lot about this stuff because, to me, it’s not that big of a deal. It seems a bigger deal to everybody else.

Okay. So, starting with the ex copywriting apprentice, let’s just get this out on the air, because everybody was ask me about this. So when I moved to Roseburg, Oregon- And I don’t live there anymore, I live on the coast now, back in Bandon, Oregon now, thank god. When I moved to Roseburg, Oregon, I needed someone to clean my house, because I’m just too lazy to do such things. Ten-minute work day keeps me very busy. So, my friend Trevor Mauch, who’s the most prominent businessmen in that town, and he’s a good friend of mine. He’s the one actually got to move out there. He’s like, “Well, I know this girl who could clean your house,” and he gave me her information. I contact her, I hired her. She was great. I mean just great at it, just made my life so easy.

And then, later on, she she started another business where she would cook meals, gourmet meals, because she’s an excellent cook. I mean, just one of the best I’ve ever had. She would deliver those to your house. So after that I thought, “Well, she’s already cleaning my house. She’s already cooking my meals. I might as well date her.”

So I started dating her, and very early on while we were dating … we kind of dated on the sneak, actually, for a couple of months, cause I just don’t like the spotlight. This is the one of those towns I just don’t feel like … whatever. But, after a couple of months, she was on my list. Right when she started cleaning my house, before we even dated, she got on my email list. It was a whole new world to her, this direct marketing stuff. And she was just reading my emails every day, and she’d respond to them because she thought I was actually writing her personally, which is a good thing. That didn’t go on forever, but she kind of figured it out. But that’s the effect you’re going for, you know? Anyone who’s not in this business, they don’t realize that that’s what you’re going for.

Anyway, she would read my daily emails, and she got into it, and when she started that business where she was delivering meals, she started … She didn’t have any of my products or anything. Just by observing what I’m doing, she started writing some email, which she would also turn those into these Facebook group posts. She’d go to local Facebook groups, that’s how she was selling herself. And she wrote this ranting email about minute rice. She was just real passionate about how much she hates instant rice. I’ve never seen anything quite like it.

And I said, “Jill, this is a really good email,” and I said, “I’m going to use this as an example in one of my email players issues,” and she got really excited. And then, I made what I believe is a mistake in hindsight, of taking her on as an apprentice, which basically just screwed everything up. It’s hard to work with people that like in that capacity. Our personalities just did not really mesh that well in that relationship.

She was my apprentice for a few months and then she soon became my ex copywriting apprentice. Which, to me, adds the entertainment level to the whole thing. Even in my Facebook group, I go from this 90210 type feel to everything, it’s like a little soap opera going on. That’s why I’ve got a main chick and a side chick.

RM: Trying to figure out if your Dylan, the bad boy, or Brandon, the kind-of-bad boy, or…

BS: I don’t know who the hell I am. I think I’m just like the dad or something. I don’t know, maybe I’m David, the little geeky guy.

KH: No, don’t be David. Don’t be David.

BS: I’m up there rapping.

Anyway, long story short, that’s how she became the ex-apprentice. And she just didn’t really, you know, she just had to go her own way. Honestly, her and I have not talked since June because we had a falling out. I actually have no idea what she’s up- I saw one of your questions. I couldn’t even tell you what she’s up to because she doesn’t speak to me anymore. So, take that for what it is.

Soon after that is when I launched El Benbo’s Apprentice, which had now whole lots- Even though I wanted to use her story, I couldn’t after the falling out, I didn’t want to use her story. In fact, that was the last thing she ever told me, was like, “I don’t want you using any of the … telling people how much money I made or anything,” so I’m like, “Fine.” That’s fine, that’s fine. I understand that, I don’t have a problem with it.

When I launched El Benbo’s Apprentice, which had been in the works for months before that, which was a membership site because I was giving so much free information out on my podcast on accident, I wasn’t intending to. I’m like, “I need to be charging for this. Why don’t I have a paid podcast? Let’s just see what happens.” I told my producer- Jonathan Rivera is my producer, and we partnered on all that. And then I brought Misty the podcast, babe and she’s the one who does my introduction voice and all that. I brought her in on it because she was writing my emails for me to that list, the podcast list, and she was great at it. And she’s really the only person I’ve ever let write emails for me because our personalities are so similar.

So we decided we’d do a three-way partnership on El Benbo’s Apprentice, and it was probably the most successful launch I’ve ever done, just looking at the upsales. I think each buyer was worth $27 or something, for a $7- You know, they they got in for $7. Well, you were there, you got in for $7, but we upsold four things to you and all that. It was very successful.

But the problem was, it was a total nightmare. I knew I wanted to end it before … in fact, I purposely didn’t send out emails out the last day because I’m like, “Ahh, this sucks. I hate this.” Nobody knew how to use support ticket system, they’re coming to me personally. I got 50, 60, 70 people coming to me. They had legitimate problems, I’m not saying they shouldn’t. But it was like, if it’s like this at 1,000 members, what’s it going to be like when it gets to 10,000 members? They’re hunting me down on Facebook, they’re hunting Misty down, asking her technical questions. And Jonathan, he was going crazy. And so, I just said, “I’m ending this. I don’t need it. It’s not worth it.” I’d rather live life in a way that I enjoy. I don’t really need the money, it’s not … I mean, it’s nice but I don’t need it. I’d rather go put this energy into something else.

So, that’s the story behind that, and I literally killed it off the day after the launch. It took a couple of months, though, we had to still deliver on some stuff and all that, but that nightmare is long past and I still wake up in a cold sweat thinking about it.

But that’s the lesson. My lesson from that is I don’t belong in a membership site. Some people love that. My friend Ryan Lee, for example. He’s been doing membership sites for 18 years, and he says, “Man, a print newsletter was so much easier.” But he’s good at it. He’s a social guy. I’m just not that social. I’m not this extroverted guy, I’m like this introverted Grinch. I’d rather be yelling at people, you know?

Now, I know people who are great at membership sites, and they should. There are people who like doing print newsletters who should do that. There are people who hate doing print. I know someone who hates doing print newsletters but he does one anyway. Makes no sense to me. So, yeah. You’ve got to build your business to suit your preferences, and I think that’s the big lesson out of that. A lot of people like to follow people and trends and all that. “Well, that’s what so-and-so is doing, that must be what’s working.” No that’s what’s working for that person. What works for you might be completely different.

So, we talk about Facebook groups, right? What you guys are doing, your goal for your group is completely different than the one I have going. But if somebody just said, “Oh I’ve got to do this. Ben’s doing no value I need to do no value.” They may not get any members that way. I’ve been building this audience up for 15 years. I mean, they’re used to me. They understand what I’m doing. There’s a relationship and a bond there. It’s all intangible, it’s not something that can be tracked or measured in any way other than my gut feeling, and knowing my market.

So that’s why I think everybody has to make their own way in this and if they do they will stand out and they will be much more successful and have more peace of mind.

RM: So, Ben, I have one more question for you. When you launched the community, you killed off the podcast, or at least you going to put it … pulled it into the community, and then killed it off and, I have to say, one of the most valuable podcasts I ever listened to was the series that you did when you tore apart one of Misty’s sales pages.

You basically went step by step, and I can’t remember if it was three or four episodes, but I listened to that three or four times. Even for experienced writers, this stuff his gold.

But then the podcast was gone, and I think you just brought it back. It doesn’t look like it’s on iTunes yet but it’s on your site. Are those kinds of things coming back? Is the podcast a weekly reality now? Is it something that you’re throwing time into? Tell us a little bit about that.

BS: Yes. I always knew I’d come back in a podcast, but I wanted to do it very methodically, different than before. The podcast, which is called the Ben Settle Show, which is dead. I have it on my site as archived, so they’re all on my site. I don’t think those will be on iTunes ever, but they’re on my site. They’re on my producer’s site, too. So, those are easily accessed on my site now.

The new one is on iTunes and we just finally … you know, I don’t know why I didn’t do this originally, but I just finally put an iTunes button on there for people who prefer iTunes. I just launched it on January first, New Year’s Day. We’ve got the first 20 shows in the can, so all the way through May. One a week. We like to get ahead. And so I can assure you, that gets really crazy, and really controversial. I’m not trying to be, but for example, I do a whole episode on why I think equality is bullsh*t. Not because I don’t think it’s a good thing, but I just don’t think historically it’s ever been a reality. I don’t think it ever will be.

So there’s just things like that I get into. I’m trying to keep it less how-to and more mindset, like thread holes like I would do in my group. Just deep thinking on stuff. Sometimes it’s how-to, some of it is, but hopefully like in the power one you can read stuff that goes beyond business.

KH: Ben, you know I’ve got my last question, just from your perspective on everything you’ve learned with clients, beyond clients. What should new copywriters take advantage of in today’s market? Have you seen anything where like there’s a big hole because we’re all focused on writing sales pages and emails and web copy, but there’s something else that we could step into? Is there something that we should be paying attention to today?

BS: Yeah. So, what we have is a glut of copywriting information. Right? It’s like, when I was starting out, they didn’t have podcasts or any of this stuff. It’s great. I mean, there’s so much out there. It’s like, now you have to figure out what not to pay attention to.

Here’s what we have going for us, and this stuff has been around since the internet’s inception, but man, it makes life so much easier at the research stage when you can just go be a fly on the wall in a forum somewhere. For example, I was in the weight loss niche for a couple of years, and the guy who did the traffic and the stats is my friend Jim Yaghi, and he’s like an AdWords guy. When I did Copy Slacker, I asked him, I said, “Can you give me some kind of testimonial about how I’ve helped you?” The product hadn’t existed yet, but I just wanted testimonials about how I helped them. And he goes, “Ben, I don’t think I told you this, but you’re emails and your copywriting, and your sales letters converted the front-end list at 40% to buyers,” which is pretty good.

RM: That’s not bad at all.

BS: And even in a rabid market like that. No, I’m not an overweight woman. I don’t know, I mean, maybe people might think I am, but I’m not. I don’t really understand the problems they have, right? So how can I write someone?

Well I did all my research in just going to forums where heavy women hang out and they think it’s anonymous, because it is, it’s the internet, but they don’t realize there’s lurkers and all that. And they will say stuff that they would never say to anyone else in real life. There’s just no way. I would get so much insight by just being a fly on the wall and really understanding where they’re coming from, really empathizing with them. Really, there’s so much about that market that the average weight loss marketer just doesn’t see because they’re not doing that. They’re just looking at all the other ads out there and saying, “Well, I’ll swipe that, and that’s what’s working.”

That’s a terrible way to go about it. You’ve got to go deep into these markets and really try to become one of them mentally. Like, get inside them. And these forums make it so easy, especially for writing emails. I’ll give you an example. Some of the best emails I wrote were I would go to these weight loss forums, and most of them, the software would let you sort the threads by the number of views. So the most viewed thread would be at the top. And a lot of times, those titles were just subject lines I could just pluck right out. Those were obviously getting a lot of views, and I would read the stories people would write in them.

One of my highest selling emails in that market was, the subject line was, “Humiliating fat Facebook pics,” and that was actually the name of the thread, and it was about this lady in there who was trying to lose weight. She’s eating right, she’s exercising. You really rooted for this girl, you wanted her to be okay, but her friends, her passive aggressive so-called friends were tagging her heavy pictures on Facebook just to bring her down. And so I wrote an email about that.

Now, no other weight loss marketer that I know would have thought of that. I wouldn’t have thought of that. I had to go to the market to get that. Never would have thought, copywriter would never think that. You have to go into the market. And, incidentally that made us a lot of sales, but when I got out of weight loss, there’s these guys that are really two of the highest selling affiliates on Clickbank in that market out there, like this really high level. And I said, “Dude, why don’t you take this email and just tell me how it works?”

So he used it during this lunch where they were competing against people with two million person lists, like BioTrust and all this. And he said they were just killing it. They beat everybody, and they weren’t even mailing as much as these other guys because he was using these emails I wrote three or four years earlier that were just purely market-based. There weren’t even any claims in them. I was just walking people through stories, like these horror stories that they were going through. I don’t know if that adds to anyone’s life, but that was a very very profitable lesson for me to learn.

RM: Message mining is a tactic that I think just about everybody could improve their copy by asking the market what they should be saying to them. That’s fantastic advice. So, Ben, we haven’t really talked about zombie fiction.

You know there’s all kinds of things that we can talk about as far as mailing you every day, but we are running out of time. So, hopefully we can have you back in a future episode. In the meantime, though where would people find you if they want to connect with you online?

BS: First of all, I would be I would be honored to come back whenever you guys want. So it’s no problem on that. You can find me at, and if you give me your snowflake, precious precious email address that you’re so scared of giving, up I will send you the first issue of my email players newsletter as a PDF. It’s a print newsletter, but I’ll send you the PDF of the first issue. It’s a very real $97 retail value and there’s 24 ways in there to start making more sales with your email, starting right away. I’ve had people literally tell me that free issue made them thousands, and in one case tens of thousands of dollars, and that’s just the free issue. And you can have it if you go to

If you don’t opt in, if you say, “Ben, I don’t trust you. I don’t like you,” which is understandable by the end of this. And you say, “I’m going to give you my”- Or you think you’re just going to give me some like bullcrap hotmail address, that’s fine. If you click through you don’t have to give it to me. You can click through and there’s almost 2,000 pages of blog posts, there’s well over a dozen hours of interviews I put up there, and plus, my podcast is up there, my old podcast is up there. That’s like, 60 hours worth of content and it’s all there. It’s all free. It’s just, you know, there it is.

RM: Fantastic.

KH: And Ben, can we hang out with you anywhere? Do you go to conferences or can we hang out with you in person ever?

BS: Yeah. Only when I’m speaking do I go, and if so- Okay, so here’s what’s on the agenda for 2017 as of now, and hopefully more will be added. In February, in New York, I’m doing an event with Dan Meredith and Ryan Lee. We call it Good Cop, Bad Cop, Insane Cop. And Ryan is the good cop, I’m the bad cop, Dan’s the insane cop. And we’re going to teach about continuity, how we make a living with continuity. I do print newsletters, Ryan with those memberships sites, and Dan does a paid Facebook group. That’s gonna be a one day, it’s only going to be $200 to attend. That’s in New York. That’s February 4th, I believe.

The week after that I’ll be in Orlando speaking at my friend Ray Higdon’s event on email marketing, so that’ll be in Orlando. I think the 11th or something like that. Later on in the year, me and Misty, who I mentioned before, and another friend of mine named Troy. We’re doing an event in Napa, California, at a winery and we haven’t even promoted that yet but we already have the place. We can fit 20 or 30 people in there, it’s going to be like a wine tasting event. We have four hours. The first hour will be just talking, whatever. The second and third hour I’ll be teaching, and the fourth hour just mingling again, and then we’re going to go have fun in Napa for a day or two.

So that’s that. And then later in the year, probably in the fall time, definitely in the fall time, October probably. My friend Kevin Rogers, him and I do this … we started an event this last October called Email Addiction, and that’s like three or four people that we bring in, and we just really get deep into their problems with email and stuff, and it’s not super pricey but it’s up there.

But those are the four events I have so far, and you know, whenever people ask me to speak I rarely ever say no, so probably there’ll be more than that. But that’s what I got for now.

KH: Perfect. All right, well, thank you Ben. We really appreciate it.

BS: Well, thank you guys.

RM: You’ve been listening to The Copywriter Club Podcast with Kira Hug and Rob Marsh. Music for the show is a clip from Gravity by Whitest Boy Alive, available in iTunes. If you like what you’ve heard, you can help us spread the word by subscribing in iTunes and by leaving a review. For show notes, and full transcript, and links to our free Facebook community, visit We’ll see you next episode.

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