Interview with a
Barefoot Writer: Ben Settle


Ben Settle

“If what you’re writing isn’t fun, then throw it out and write something that is fun. It should never feel like a chore if you do it right.”
— Ben Settle, High-Earning Email Specialist

If you’ve ever had even a fleeting thought that you’d like to write emails for a living, Ben Settle is the guy to know. Not only is he big on building connections in the subtle ways that email can, but his emails demonstrate what he lives.

Ben’s mantra? It’s the simple art of being genu­ine. According to Ben, it’ll get you further in the long run. He also fervently believes you’ll achieve more success from stepping back to enjoy life than you ever could with any kind of nose-to-the-grindstone success.

Like many Barefoot Writers, Ben got his feet wet in the paid writing world by crafting ads and put­ting together email campaigns for clients. He had a knack for all of it, proven by the tens of millions of dollars his copy earned those clients. He also gained fans by writing for well-trafficked blogs like Copyblogger.

It wasn’t long before Ben found his true writing love: The email. And as you’ll read in his interview, he’s never looked back. Since turning his atten­tion fully to email, Ben has built up a stable of fol­lowers, including upwards of 400 subscribers to his paid, print newsletter, called Email Players.

But his writing pursuits don’t end there. For fun, Ben writes “twisted monster horror.” He currently has a well-praised, three-book series of novels available through Amazon, called Zombie Cop, Vampire Apocalypse, and Demon Crossfire.

These days, Ben spends most of his time at home in the tiny town of Bandon, on the Oregon coast. Read on to discover what he does to pass the time when he’s not writing high-level conversion email masterpieces. And don’t miss Ben’s tips on when not having an assistant could cost you money, how to turn on your “testimonial” radar, and why art and pictures intersect with writing.

As a kid, what did you dream about becoming when you grew up?

When I was really young I wanted to be a scientist. I’m amazed I didn’t accidentally kill myself when I’d spend hours in the bathroom mixing various liquids in the medicine cabinet together, trying to create something that would make the dry ice-like effect where it looks like smoke is coming out of the container.

How did life as a writer come into the picture?

Later, when I got older, I discovered comic books and got obsessed with them. I used to write comic book stories but could never find anyone to draw them. So I started teaching myself to draw so I could see what my stories looked like. Unfortu­nately, my artistic skills were never very good (I’m too much of a slacker to be an artist — which takes a lot of discipline).

But I still enjoyed the writing part and started hav­ing dreams of becoming a screen writer. In fact, when I made it to community college, for my first English 202 class I wrote a paper on how to write a screen play. Incidentally, the research for that was immensely helpful later on in life when I started writing sales copy and, most recently, twisted monster novels. Being able to write visually — so people “see” in their minds what you want them to see — is a huge advantage any writer will have.

For example, I treat my sales copy and fiction writing like screen plays. I want people to see in their heads what I’m talking about because peo­ple think in pictures not words. I want my sales copy to feel like they’re watching a movie (in their heads) about something that’s super fascinating to them. So it’s not just a lecture or dry facts — it’s an experience. Something they can’t get out of their heads until they buy …

You started out as a direct-response copywriter for clients and switched to writing emails for yourself. Why the change?

From the very beginning, I never really wanted to be a freelance copywriter. I did it to pay the bills. My goal was always to build a business and be my own client, writing just for my own products, without any clients or having to filter my work through anyone else. I just hate authority of any kind and can’t help it.

It just so happens that early on in my career I was on Matt Furey’s email list. I was in awe (still am) of his lifestyle. Here was a guy who got up each day, wrote an email, and then was basically done. And he had built a rather large seven-figure business doing that. So I spent the next several years try­ing to build a similar type business.

I studied everything I could find by him. It’s the foundation of everything I still do today in email. I veered away from a lot of what he teaches and does to make things fit my personality and goals. But the foundational stuff is there — infotain­ment, mailing daily, treating email like talk ra­dio, etc. Anyway, it didn’t take long after apply­ing what I learned and putting my own twist on things that my sales went through the roof, as did sales for clients when I did their emails. In fact, even when I sold products without using a sales letter, I got sales because the emails were doing all the heavy lifting (some of my students now don’t even bother with a sales page, they just send people to a PayPal order form … Yes, they could make more with a sales page, but they just don’t have the time, I guess).

Eventually, people on my own list started asking, “Hey Ben, when’s the email product coming?”

Had that been your goal all along?

I had no intention of even creating an email prod­uct. People were just observing what I was doing, finding themselves buying, and wanted to know how I was doing it.

So I created a high-ticket product called Street Smart Email (no longer for sale) that cost $795. Well, turns out since I’m obsessed with email, al­ways thinking about it, always testing and trying new things, and always making new discover­ies … I had to keep updating it. Then one day I got the idea to create a print newsletter where I could keep teaching all these new discoveries and not have to constantly update a product.

Since then, I haven’t done any client work and mostly just teach email (although I still teach copywriting too, it’ll always be my first love so to speak). My goal to have a Furey-esque busi­ness model was accomplished. I never could have done that by just being a copywriter and without using email.

Given all that, what’s your opinion of sales copy?

Don’t get me wrong, sales copy is important.

But if I had to choose between having the world’s best copywriting skills or having top notch email skills, I’d choose email every time. It’s made me (and certain clients who hired me for emails, when I had clients) far more money. In fact, in a golf company I used to work for, one of the own­ers (who was not exactly the sharpest tool in the shed) took the sales page down. He was scared they’d come off as being “salesmen.” Can you imagine that?

They took a working sales letter down that was making them sales to cold traffic because they were scared of being seen as trying to “sell.”

Anyway, my emails were making so many sales alone (without the sales page) that they got away with that for a while. Fortunately, the other part­ner wasn’t as short-sighted. They put the sales page back up, and sales immediately multiplied. They went from $0 to $200K per month and more very quickly. My point in telling that story is, when you combine email and copy, and you have a proven offer, you really can’t lose.

What does a typical “work” day look like for you?

A typical day for me involves waking up to my long-suffering dog (her name is Zoe) demand­ing to be let out, gagging down a couple fistfuls of health supplements, and then beating on my wooden Wing Chun Kung Fu dummy for a half hour or so. After that, I go to my office downtown on the coast.

What I work on depends on what I have go­ing. The ideal day is just writing an email and then goofing off walking my dog on the beach, wine tasting, taking a road trip, or just puttering around the house (I enjoy solitude).

But, sometimes I do other things, too. Like record­ing my podcast, writing my Email Players newslet­ter, working on my next novel, checking in on and participating in one of my private Facebook groups, answering questions for paid newslet­ter subscribers, or traveling around the country speaking, which I’m starting to do more of (i.e. the AWAI Web Copywriting Intensive that’s coming up at the end of February, but also the Oceans 4 Mastermind I do with a few of my colleagues each year, and other assorted events I get invited to).

The one thing I always do each day though, is write an email. It’s the one activity that drives my business — what Gary Halbert called “Operation Money Suck” — where you always do the one thing you’re indispensable at that brings in the money. Plus, it’s like therapy. I have to write emails each day now or I don’t feel right and get even more cranky than usual.

You use the word “anti-professional” in some of what you write. What do you mean by that?

There are people who are professional, there are people who are unprofessional, and then there are people like me who don’t fit either label that I call anti-professionals. It’s a term I first wrote about several years ago. And, it describes a cer­tain kind of businessman who’s like the old school cowboy on his horse going it alone, living by his own code of honor and following his own rules — the guy who doesn’t try to impress the customers (or anyone else, for that matter), but always gets the sale.

Here’s an example. Back in July, I visited a wine bar on the coast. This place not only has great wine, but the owner personally cooks your meal on the spot. There is nobody else cooking but him, and he is one of the best cooks I’ve ever met. Anyway, when you go inside, the first thing you see on all the tables is a little “reserved” sign. Thus, when you walk in, your first thought is, “Crap! Did I need a reservation?” But alas, no. You see, the owner doesn’t want *everyone* as a customer.

As he said to us, “I just put those on the tables to keep the riff-raff out.”

Riff-raff being anyone he doesn’t want to serve.

For instance?

After sitting down, a man and a woman came in with two kids who were being kind of loud and obnoxious (who brings kids to a wine bar?). Any­way, the owner really doesn’t like kids in his wine bar because they tend to be boring customers that want basic food items he doesn’t serve, who parents then demand he create off-menu items for. And, he told us, even if they do order some­thing, they don’t spend enough money to make it worth it.

So the owner shoos them out and says all the ta­bles are reserved. Then, he says, “You’re welcome” to the rest of us in there.

That is a perfect example of an anti-professional. This guy runs his business the way HE wants to. He serves ONLY the kind of customers he wants. And, plays on HIS terms. He’s quite prosperous, too, and is kind of like Seinfeld’s Soup Nazi (the Wine Nazi?) in his own way.

What do you do to blow off steam in Oregon?

I love walking my dog on the beach. She’s get­ting older, so I like to do this as much as possible while she’s still here. I also do my best thinking and learning while walking her (listening to mar­keting and business trainings).

There’s also great wine tasting inland a bit that I enjoy.

I love hanging out in Old Town Bandon where I live. It’s small, but has lots of cool little shops and a few decent places to eat and hang out. My dad lives in the same town and I enjoy hanging out with him down there. We like to golf, too.

When I can, I take road trips wherever I may roam (Napa Valley for wine tasting, Portland, wherever I feel like going). And I enjoy getting to fly to dif­ferent places to speak and teach every couple months or so, just to get out of my routine.

But mostly, I’m very much an introvert and a homebody. My home is my castle and I enjoy just hanging out alone with my dog.

The testimonials on your website blow most testimonials out of the water. They’re specific, unique, and from really big names in the di­rect-response writing world. How did you get them?

I have a rule. Whenever someone gives me props of any kind (big or small, whether in writing or I hear them say it somewhere else, doesn’t matter) I do at least one (preferably both) of two things:

1. I ask if I can use it as a testimonial
2. I ask them to elaborate

So a lot of the testimonials you see were not even intended to be testimonials. Gary Bencivenga, for example, wrote me a nice note because I sent him a detailed testimonial about his farewell DVD’s (one of my most prized-possessions). He wrote in his letter back that he enjoyed my website so I simply asked if I could use that as a testimoni­al. Same with all the others. Most of them were just off-the-cuff comments someone made and I asked if I could use them.

It’s important to have your testimonial “radar” on like that. Clients, customers, people are probably always giving you testimonials, you just don’t re­alize it.

Those off-the-cuff comments tend to be more powerful, too.

I prefer the from-the-gut testimonials versus the canned ones where they’re trying to give me a testimonial. I appreciate both kind, but the natu­ral ones, where they didn’t even realize they were doing it, are the ones that stand out the most in my experience.

Every time someone writes you an email, sends you a text or Facebook message, or says some­thing on the phone to you, bottle that up and ask them if you can use it as a testimonial. Sometimes, people will then elaborate on it and give you an even better one. But a good sound-byte sized testimonial — especially from someone with au­thority and celebrity-appeal in your market — is worth solid gold to you over time.

How do you stay on top of all your ventures?

My business model is so dirt simple I don’t use anything for productivity except a 3x5 note card that I divide up into five sections with a pen (Mon­day-Friday) and write what needs to be done each of those days.

Have you ever hired a personal assistant or a virtual assistant?

I’m probably the most simple-minded person you’ll ever meet. I hate complicated. And I love simplicity. This is what attracted me to Matt Furey’s business model so early on. It was simple: Get up, write email, watch sales roll in, go off and do whatever you want the rest of the day. So the way I’ve built my business, I haven’t really needed an assistant.

But, that said, not having an assistant has cost me money, too. There are things I could and should be doing that I don’t (no interest in doing them) that an assistant would be perfect for. Like, for example, calling new customers and welcoming them to my world and then offering them anoth­er product at a discount. Calling people who have bad credit cards and having them give a new one. Doing the leg work of booking me on radio shows and podcasts which generate some of the best, highest-quality leads you can ever get. Upload­ing my daily emails to online article sites, social media sites, YouTube, and iTunes (amongst other places), doing my customer service (which, while it doesn’t take a lot of time, is one of those things that adds up), and the list goes on.

Who’s had the biggest impact on your life?

Hands down, the biggest influence in my busi­ness life has been Matt Furey. I would probably be pumping gas down at the local Chevron if it weren’t for him, his teachings, and the inspiration he gave me, especially when times were really lean and all I had was a vision of what I wanted to do (create a thriving business writing just one email per day). I’ve never met the guy except via exchanging a couple emails.

But through observing his business, I’ve learned the power of consistency, of not being afraid to use my personality in my marketing to the max, of not being afraid to be controversial, of not car­ing if someone is offended by something I say (which stops a lot of people — everyone is of­fended by everything these days — if someone is offended it’s not your problem, it’s theirs), of creating a business that suits my lifestyle, and the list goes on.

Other people that have had huge influences on me are the late Gary Halbert (whose ads I used to write out in my own handwriting — I learned copywriting almost exclusively from his teach­ings), Gary Bencivenga (whose products have taught me the psychological side of copywriting), Ken McCarthy (who drilled the importance of po­sitioning — far more important than the copy — into my head, and helped me develop a keen B.S. detector), the late Bruce Barton (from the book The Seven Lost Secrets of Success: Million Dollar Ideas of Bruce Barton, America’s Forgotten Genius, by Joe Vitale, that got me into direct marketing in the first place.)

Also, Gene Schwartz, whose teachings radically changed the way I wrote copy, Michael Senoff (who showed me some important lessons about the business-side of things — like never doing joint ventures with anyone who doesn’t want to make money as badly as you do), Dan Kennedy (whose No B.S. Time Management book is pure genius, especially the chapters on self-discipline and the power of being punctual). There are more, but those are some of the ones that stand out the most.

How do you prep for an email-writing session?

I don’t — I just sit down and pound away on the keyboard. It’s pretty automatic now that I’ve been writing daily emails for almost 10 years. Writing begets writing. The more you write, the more writing you’ll do and the easier it gets. At least, that’s been my experience. I’ve never understood people who find writing so torturous where they liken it to slitting your wrists and bleeding all over the page. If what you’re writing isn’t fun, then throw it out and write something that is fun. It should never feel like a chore if you do it right.

If you could interview anyone, living or dead, who would it be and why?

I would interview the late Jim Straw. He was one of the few people I’ve ever seen get away with emailing blatant sales pitches every day. He was also the only person I ever heard of who could sell a $997 e-book (160 pages) without a guarantee and do so in relatively big quantities. (I heard he sold about 10 or 11 per month). Talk about a busi­ness model!

What must-read books—on any topic—do you recommend for folks interested in a writ­ing career?

My all-time favorite business book (that I kept in my bathroom for several years reading it over and over and over … TMI notwithstanding) is Ken McCarthy’s System Club Letters book. It’s good for writing, for persuasion, for marketing and busi­ness in general, all of it.

Another is the book I mentioned before, The Seven Lost Secrets of Success by Joe Vitale. It’s about Bruce Barton (the second B in the BBDO agency). He was a household name in the early to mid-1900’s and now nobody knows who he is. The great John Caples revered Barton, as did all the marketing and advertising people of that time. For writers, there is a chapter about sharpening the knife of persuasion. There’s a great quote in there from Horace Greeley (a big time newspaper guy in the day) about taking an editorial, chopping off the first half, then running just the second half. That is probably the best “writing” advice I ever heard.

Dan Kennedy’s NO B.S. Time Management is a must if you want to get paid what you’re truly worth. The chapters I mentioned earlier on self-discipline and punctuality are mandatory for writers who want to immediately get paid more and stand out from every and any other writer you compete against in my humble (but accurate) opinion.

Gerry Spence’s How to Argue and Win Every Time will inspire you to want to be the best storyteller you can. The book talks about how he hasn’t lost a trial since 1969 and one of his big “secrets” is simply telling stories — to the jury, to the judge, in his legal briefs (which are usually dull and bor­ing for judges to read), etc. He was once accused of hypnotizing a jury, when really, he was just tell­ing stories.

Stephen King’s On Writing — great for the me­chanics of writing; they all apply to copywriting especially.

Gene Schwartz’s Breakthrough Advertising — I’ve read that one probably 16 times (give or take) and I still haven’t gotten all the gold out of it.

Finally, anything you can get your hands on writ­ten by Gary Halbert, John Carlton, Gary Benciven­ga, Jim Rutz, Bob Bly, and any of the other A-list writers.

What does success mean to you?

Being able to do what you want to do, when you want to do it without having to answer to anyone else. Just being free on the earth without debt or financial burdens bogging you down. Not the most profound definition, maybe, but it works for me …

What’s your favorite, most decadent dessert and your favorite ultra-healthy food?

Warmed up pecan pie with vanilla ice cream melt­ing over it and a big glass of filtered water.

Favorite ultra-healthy food — does wine count since it’s from fruit? [Laughter] No? Okay, then I’d go with broccoli.

What’s your number one piece of advice to someone who wants to break free from work­ing for someone else and launch a writing career?

The mountain-smashing power of consistency.

For example: Jerry Seinfeld, who was making al­most $300 million per year at his prime, talked about his calendar method. During his enor­mously successful career, he made it a goal to write one joke per day. Every day. No excuses. Just one joke — whether a good joke, bad joke, or bland joke, it did not matter. What mattered is, he made a goal to write one joke per day. He also has a big wall calendar where, every day after he writes a joke, he puts an X through that date. And then, the same the next day. And the same the day after that so it was like a chain of X’s through the month.

He said he never broke the chain. And as long as he didn’t break that chain, he would keep experi­encing success.

No matter what you do, what kind of business you have, what your goals are … do it every day. Want more writing clients and to excel at your craft (whether writing for clients or yourself)? Then make it a goal to write for an hour each day. That’s it.

Make it a goal to do that each day, and before long you’ll have so many clients and be so pro­lific, you’ll have to start turning some away (or be forced to raise your prices). It’s the most reli­able and predictable (and simple) way to experi­ence mass success that probably has ever been invented.

And the best part is, it’s free.

To read more interviews from fellow Barefoot Writers be sure to checkout The Barefoot Writer's Club.

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Published: October 8, 2017

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