Ben Settle Bares It All (Well, Almost)

Today I’ve got a special written interview with Ben Settle — 12 questions, 12 answers, and a goldmine of valuable information for copywriters, marketers, and online entrepreneurs.

In addition to being the most committed member of our meet-when-we-feel-like-it mastermind group (he actually gets the “shakes” if we don’t meet every month or so), Ben is one of the strongest copywriters I know. He’s consistently writing stuff that makes me scratch my head and say, “How does he do that?”

And, lucky for both you and me, Ben graciously agreed to a really in-depth interview. I’ve published all 12 questions and answers below. I think you’ll see Ben tells it like it is and doesn’t hold anything back.

If you like the interview, please Tweet it, Stumble it, Digg it, bookmark it, etc. Thanks!

Exclusive Interview: 12 Questions
with Copywriter Ben Settle

1. How did you first learn about the field of direct response copywriting?

I stumbled onto it by complete accident.

What happened was, my wife and I had spent a couple years slugging it out in MLM with zero success.  Complete and utter failures in every way.  We spent so much money on leads and products and got into so much debt we couldn’t even afford to live in a real apartment or house.

Instead, we lived in a little two room office.

Not our finest hour, let me tell ya.

Anyway, it finally dawned on me this MLM thing was not working and something had to change.  I still remember it like it was yesterday.  It was about 3 am, I was laying there on the floor (we didn’t have a bed or anything, the joys of office living) plagued with insomnia and praying to God to tell me what to do.  My wife and I had only been married 9 months.  She left everything she knew and everyone she loved 2,500 miles away to marry me and look where I had gotten her?

I felt like such a loser — with a capital “L”.

So I got up and started looking for something to read.  There was a book by Joe Vitale called “The 7 Lost Secrets Of Success.”  It is about an old school advertising man named Bruce Barton.  I started flipping through it and read a story about a man Bruce helped during the great depression.  Apparently this guy was in sales and had a reputation for writing sales letters, in particular.  So Bruce took the guy to the window and said something like, “Take a look at all those buildings out there.  Why don’t you write them a sales letter selling them on hiring you?”

I don’t know what it was, but that story grabbed me.

And everything just seemed so clear — writing sales letters.

From there I ran into the usual suspects like Dan Kennedy, Gary Halbert, etc and haven’t looked back since.

2. Once you decided to become a freelance copywriter, how did you get your first clients?

After stumbling onto Gary Halbert’s site I saw a newsletter he wrote that immediately caught my eye (for obvious reasons).

The title was: “Why Multi-level Marketing Sucks.”

And in it, Gary described a way to get clients where you don’t collect an up front fee.  Instead you are basically “investing” your time and abilities in someone else’s product in exchange for a cut of the sales.

That seemed logical to me since I had no real experience.

So I found this business-to-business email based forum type thing where people just sent each other offers.  Back then this kind of thing was more widespread as we didn’t have the mass spamming problem we have now.  And I offered to write ads for people for no fee, just 5% of the sales.

Which, looking back, was really stoopid.

But even so, I got about 4 or 5 clients out of it, learned how to dig in and write ads, deal with clients and some of the other realities (good and bad) about freelancing.

I then used those ads as my portfolio on Elance.

From there, I got a couple gigs and made some money.  Eventually, I ran into my friend Michael Senoff and we did some projects together and things took off from there.

3. You send out an email 5 days a week to your subscribers. How do you generate so many good ideas to write about?

They’re just everywhere.

I’m always thinking about emails in the back of my mind and am, I suppose, receptive to them. It’s like an antenna and I’m just looking for anything that can be turned into a fun and interesting read for people.

A lot of it comes from pop culture.

Like, for example, movies, TV shows, comic books, something I read on yahoo news, etc.  I also draw on real life.  Everything is an email — from my dog pooping, to the movie I just watched to the latest adventure with a clueless business or customer service department.

It’s not always peaches and cream, though.

Sometimes I can’t think of anything. When that happens I consult a folder on my hard drive where I am always logging random thoughts, ideas, phrases, news headlines, etc.  From there I can usually find something to talk about.

The key for me is to remove all pressure.

I don’t really buy this whole “gun to the head” mindset thing.

I’m not knocking it as I know some people who thrive on it.  But it doesn’t work for me at all.  If someone put a gun to my head and told me I HAD to write an email, or an ad or perform in any way, I’d probably just tell ’em they might as well blow my brains out.

Because it just ain’t happening, Bugsy.

Instead, I give myself permission NOT to write anything.

I have a goal, yes.

But whether I make it or not is cool either way.  Usually, that results in a lot easier writing and flowing forth of ideas.

4. I often think of you as the “John Carlton” of our Mastermind Group. How have you developed your style — and what do you do to continue becoming a better copywriter?

While I am extremely flattered you’d call me that, I’m not even in the same ballpark as John Carlton. I’m not even in the league or even the same sport as him.

That dude can dang near make his keyboard turn water into wine.

I look at his ads and just think, “How in the hell does he DO this?” He’s taken copywriting to a level I can’t even begin to fathom.  One of the true greats and someone who really does deserve to be called a “guru” (IMHO).

Anyway, now that I’m done kissing John Carlton’s ass, I’ll answer your question.

I focus on two things:

The first is writing almost every day via emails, etc.  I generally send out 5 per week, sometimes 6.  Other times I may only send 2 or 3.  But usually I write something every working day.

The second thing is always studying my market.

It’s ALL about the market.

The writing truly is secondary.

If you know your market like you know your best friend or whatever, the writing pretty much takes care of itself.  You know what they want to hear, how they want it presented and what their hot buttons are.

It’s probably not as “sexy” as the writing.

But it really makes a big difference.

5. My first exposure to you was when I somehow found myself on your “Private Details about Ben Settle” page. (This was before you had a blog.) And I gotta tell you, I read the whole thing right then and there and decided I had to get in touch with you somehow. What were you thinking when you sat down to write that “bio”?

I was inspired by how Michael Senoff did it on his site.

He told some of the highlights of how he got in business and the events that shaped his life and ideas and business philosophies.  So I sat down one day and just started writing, starting with how I took my wife away from everything she knew and loved and dumped her in a two room office 9 months later.

That then led into writing about some other things.

Like, for example, how I found my first clients, some of my business philosophies and spiritual beliefs and why the best “luck” is the kind you make for yourself.

It all just kind of brain-farted out.

6. How badly have you been “screwed over” by a client, and what did you learn from that experience?

The worst was a well-known (pretty much a household name, or used to be, anyway) asset protection company out of Nevada.  One of those companies that sets up Nevada corporations for people.

I was kind of a fan of the company.

And I wrote the owner a letter offering him the same percentage (no up front fee) deal I originally started out with. He called me back and we got along (he is an old school direct marketer and perfectly understood what I was talking about).

Anyway, all was good until a few days later.

I got a call from some lady at the company telling me the owner, who understood direct marketing, retired and now his daughter was in charge.  They were putting together a committee and all this other corporate nonsense and wanted updates with the ads, etc.

I was still kind of new to the whole thing and went with it.

However, a pit in my stomach told me not to.

Something was big time wrong.  And I just knew it.  When I was talking with the owner all was cool.  But I didn’t know his daughter from Adam.  And this whole committee approach was really annoying — especially since they didn’t pay me anything up front.

Well, I sweated over the ad and sent it in.

This new owner chick was just clueless.

She tried picking it apart and it was obvious (even to a newbie like I was) she had no clue what she was talking about.  And after asking her some questions, the REAL truth came out — she didn’t really understand the deal I’d made with her dad. So I spent all this time writing a sales letter on pure commission, on their deadline, for someone who never had any intention of ever running it in the first place.

Still, it was an extremely valuable experience.

I learned 1.) Never deal with a client who doesn’t understand direct response marketing and 2.) Always, Always ALWAYS trust your gut.  I believe God designed our minds and bodies and spirits to sense danger and when things are “off.”

It’s like a geiger counter seeking out toxic people and danger.

Ignore it at your peril.

7. Gary Halbert is famous for claiming that “All clients suck!” Do you agree with this statement? Why or why not?

I think it’s both incredibly genius and incredibly stoopid at the same time.

I think it’s genius because I know what Gary Halbert was up to after talking to Doberman Dan Gallapoo recently.  Doberman Dan used to work with Gary and he told me it was Gary’s way of getting clients.  It was the ultimate take away.  People go crazy when you tell them they cannot have something.  Gary would (according to Doberman Dan) spend a lot of time in seminars telling people not to bother even thinking about hiring him, he’s not taking clients, doesn’t want to deal with clients and leave him the hell alone.

The result?

He’d often have a line of people practically writing him checks on the spot!

So in that sense it’s genius.

On the other hand, if you don’t have Gary’s posture and positioning and reputation for writing big winners, it’s absolute stoopidity.

If you can’t walk the walk then don’t talk the talk.

And besides that, your clients are paying for your car, your house, your kids’ college and all the toys you play with.

So why not treat them that way?

Frankly, anyone who outright resents the people who write their paychecks, ought to pick a more compatible career.

Like, for example, as a government bureaucrat.

8. Who is your #1 role model in the copywriting field? Why do you look up to this copywriter more than all others?

I’d have to say it’s a tie between Gary Bencivenga and Gary Halbert.

I learned a LOT about using drama, story-telling and structuring an ad from studying Gary Halbert.  At the same time, I learned all the really cool mental game about overcoming skepticism, proving my claims and the exact psychological process people go through when buying from Gary Bencivenga.

When I merged it all together, my response starting taking off.

Especially in the more competitive niches like self defense and golf.

9. What’s one thing you wish knew about copywriting before you got started?

That it’s all about the market first, and not the tricks and tips.

Most copywriting is about the fireworks — the “killer” guarantees or the “cool” headlines or whatever. When, in reality, it’s your market that matters most. What do THEY think?  What do THEY want?  What are THEIR hot buttons?  What do THEY find cool (as opposed to what other copywriters find cool)?

It’s not as glamorous as the sales choke holds and magic phrases.

But it’s far more important.

10. What is the best book you’ve read during the last 3 months? Why did you like it?

Ken McCarthy’s “The System Club Letters.”

Not only have I read it over the past 3 months, but I’ve read it (almost non-stop over and over) for the past year and a half.

Maybe that sounds like overkill.

All I can say is there’s a lot going on in that $20 book.  A lot of solid tips and fundamentals that are lost in all the big guru fireworks displays. Plus, each chapter is bite-sized — easy to read, digest and implement.

11. What one daily habit has contributed to your success more than any other?

Writing daily emails.

I’ve more than doubled my productivity, write probably 5 times faster than I used to, get more ideas with less strain, have attracted lots of cool marketers to my site, bonded myself with my list in ways I never dreamed possible before and, in a lot of ways, it’s been therapeutic.

There’s something about writing that does that.

It clears the cobwebs, helps you formulate your ideas and thoughts, and lets you get things “out” like if you were paying a psychologist.  I think I heard Stephen King say something like this in the past, and now I finally know what he means.

It also keeps me thinking about my list 24/7.

How can I serve them?

How can I help them?

What can I say to them to brighten their day?

What do they WANT?

12. Where can people learn more about you?

They can find me at

And, if they sign up for my daily tips, they’ll get a free eBook with 30 powerful and entertaining selling tips they can use for whatever they sell and for whatever media they use (face to face, phone, copywriting, emails, blogs, etc — it’s all about selling in the end no matter how it’s “dressed”.)  Not blatant, endless pitches, either.  I usually link to something I sell, but the vast majority have value whether your click anything or not.

Also, as I mentioned earlier, my email tips are daily.

If you don’t want a daily tip, then please do us both a favor and don’t sign up.

Otherwise, you’ll probably just end up complaining and I’ll have to send you over to:


If you enjoyed this interview with Ben Settle, you may also want to check out the interview I did for him. He grilled me with 12 tough questions and, seeing as we’re good friends (and he answered my questions), I was obliged to respond in kind.

Check it out here: How to Get Lots of New Clients in Hard Times

-Ryan M. Healy

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Ryan Healy

Ryan Healy is a freelance copywriter, list manager, and the author of Speed Writing for Nonfiction Writers. Since 2002, he has worked with scores of clients, including Agora Financial, Lombardi Publishing, and Contrarian Profits. He writes a popular blog about copywriting, advertising, and business growth, has been featured in publications like Feed Front magazine, and has been published on sites like,, and

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