Ben Settle's Copywriting Method: Daily Emails, Print Newsletters, and Infotainment

Ben Settle is the contrarian’s contrarian in email marketing. While most marketers optimize for opens and clicks, Settle optimizes for sales—and deliberately ignores everything else. While others test subject lines and segment obsessively, Settle writes one email per day, same approach, for years.

His methodology is polarizing by design. He mocks “internet marketing weenies,” celebrates unsubscribes, and sells primarily through a physical print newsletter in an age of digital everything. And he’s built a multi-seven-figure business doing it.

Understanding Settle means understanding a specific philosophy: email as relationship, entertainment as value, and consistency as the ultimate conversion mechanism.

Who Is Ben Settle

Settle’s origin story is unusually honest for the marketing world: he failed repeatedly before finding what worked.

He started as a musician, playing in bands that went nowhere. Moved to Los Angeles chasing the dream. It didn’t work out. He ended up broke, depressed, and looking for something—anything—that could generate income.

He discovered direct response copywriting through Gary Halbert’s work. Started learning. Started practicing. Eventually started freelancing. The freelance work led to his own products. The products led to a list. The list led to daily emails.

The daily email habit started almost by accident. He committed to showing up every day because he had nothing else going on. No sophisticated strategy—just consistency born from having no better options.

What he discovered: daily contact built a relationship that monthly or weekly contact couldn’t match. His audience started treating his emails like a daily ritual. Open rates stabilized. Sales became predictable. The business model emerged from the habit.

Key insight from his origin: Settle didn’t start with a master plan. He started with desperation and stumbled into principles through practice. This matters because his advice often assumes the same trial-by-error foundation he has.

Core Philosophy

The A-Pile Principle

Settle’s central concept comes from Gary Halbert’s “A-pile/B-pile” distinction. When people sort their mail, they create two piles:

• A-pile: Personal letters, cards from friends, things that look interesting
• B-pile: Bills, junk mail, obvious marketing

Most marketing emails land in the B-pile (mentally, if not literally). They look like marketing. They read like marketing. They get deleted like marketing.

Settle’s entire approach is designed to land in the A-pile. Personal tone. No corporate voice. Stories from daily life. The email should feel like it’s from a person, not a brand.

Practical application:

• Write like you’re emailing one person, not a list
• Use stories from your actual life
• Have opinions that a committee would never approve
• Sound like a human with a personality, not a company with a style guide

Infotainment Over Information

Pure information is commodity. Anyone can Google what you’re teaching. Entertainment—genuine enjoyment in reading—is scarce.

Settle’s framework: every email should inform AND entertain. The entertainment makes them open tomorrow. The information makes them trust you. Together, they make buying feel natural.

What infotainment looks like:

• Lead with a story or observation, not a lesson
• Have a point of view that’s distinctively yours
• Make them smile, think, or feel something
• Teach through narrative, not bullet points

This doesn’t mean jokes or forced humor. It means writing that’s genuinely interesting to read—writing with personality and perspective.

The Anti-Swipe-File Philosophy

Most copywriters worship swipe files—collections of proven ads and emails to model. Settle argues this creates derivative, soulless copy.

His position: study principles, not templates. Understand why something works, not just what it says. Then write from scratch in your own voice.

The controversial implication: Settle believes most copywriters are “swipe file junkies” who can’t think originally. They copy surface elements without understanding underlying psychology.

Whether you agree or not, the principle has merit. Heavy swipe file dependence can produce copy that technically follows formulas but lacks authentic voice.

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Email Players: The Print Newsletter Model

Settle’s flagship product is “Email Players”—a physical print newsletter delivered monthly by mail. In an age of digital courses and membership sites, he sends paper.

Why print works for his model:

1. Perceived value: Physical products feel more valuable than PDFs
2. Consumption rate: People actually read print; digital gets filed and forgotten
3. Commitment filter: $97/month for paper attracts serious buyers only
4. Retention psychology: Canceling a physical subscription feels more significant
5. Differentiation: Nobody else in his space does this

The business model:

• Monthly print newsletter (~$97/month)
• Back issues available as one-time purchases
• Occasional standalone products
• No complex funnel, no webinars, no sales calls

The daily emails exist primarily to sell Email Players subscriptions and keep current subscribers engaged. Everything feeds the newsletter.

What He Teaches in Email Players

Each issue covers a specific topic in depth:

• Email psychology and persuasion
• List building and management
• Offer creation and positioning
• Mindset and business philosophy
• Critiques of mainstream marketing advice

The format is dense text—no graphics, no fancy design. Just Settle’s voice teaching through examples and rants. Subscribers either love the style or cancel quickly.

Key Techniques

The Daily Email System

Settle’s emails follow a loose but consistent structure:

1. Hook: Story, observation, or provocative statement (2-3 sentences)
2. Riff: Expand on the hook, connect it to a principle (bulk of the email)
3. Pivot: Turn to the offer or lesson
4. CTA: Link to Email Players or relevant product

The whole thing typically runs 400-800 words. Conversational. One idea per email. Minimal formatting.

What he doesn’t do:

• Segment by behavior
• A/B test subject lines
• Optimize for open rates
• Use fancy email design
• Apologize for selling

Subject Line Philosophy

Settle’s subject lines are deliberately un-optimized by conventional standards. No emoji. No urgency words. No “power words” from headline formulas.

Instead, he writes subject lines that:

• Sound like a friend texting
• Create curiosity without clickbait
• Often reference the story, not the lesson
• Sometimes make no sense without context

Examples of his style:

• “The stripper and the preacher”
• “Why I hope you unsubscribe”
• “My embarrassing confession”
• “The 3pm rule”
• “What my dog taught me about email”

These work because his audience knows his voice. They open for him, not the subject line. This is crucial context: his subject lines work because of list relationship, not despite unconventional approach.

The Reluctant Hero Frame

Settle positions himself as reluctantly successful—someone who figured things out despite himself, not a polished guru with all the answers.

This frame includes:

• Stories of past failures and struggles
• Admission that he’s “lazy” and “anti-social”
• Dismissal of complex tactics as unnecessary
• Positioning against the “guru” archetype

The effect: he becomes relatable and trustworthy. He’s not selling from a pedestal. He’s sharing what worked for someone who’s probably like you.

Worked Example: A Complete Email

Here’s an email in Settle’s style, demonstrating his techniques:

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Subject: The gas station incident

Yesterday I’m at a gas station and this guy walks up asking for money.

Standard story, right? Happens all the time.

But here’s where it gets interesting.

He doesn’t ask for “spare change” or say he needs bus fare. He walks up and says:

“Hey man, I’m trying to get drunk and I’m two dollars short. Can you help me out?”

I gave him five bucks.

Not because I support alcoholism. Because he told the truth.

In a world of fake sob stories and manufactured sympathy plays, this dude just… said what he actually wanted.

And you know what?

It worked way better than the “I just need to feed my kids” script I’ve heard 400 times.

There’s a lesson here for your emails.

Most people write what they think subscribers want to hear. They craft careful messages designed to avoid offense. They hide their real personality behind “professional” language.

It doesn’t work.

Because people can smell fake from a mile away. Just like I can tell when someone’s lying about needing bus fare.

The weird truth about email: the more you try to sound “right,” the less anyone trusts you. The more you just say what you actually think—even if it’s uncomfortable—the more people pay attention.

This is why I don’t use templates.

This is why I don’t follow best practices.

This is why my emails sound like… me. For better or worse.

If you want to write emails that actually sell, the first step isn’t learning formulas. It’s getting comfortable saying what you really mean.

I teach exactly how to do this in this month’s Email Players.

Including the one question that instantly kills “professional” writing and forces your real voice onto the page.

Link to subscribe: [link]

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That’s roughly 300 words. Story → principle → pivot → offer. One idea. Conversational throughout. No hedging or corporate-speak.

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Are you writing copy for clients, or running your own offers? The answer changes which frameworks matter most. Get the free training tailored to your situation.

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When NOT to Use Settle’s Approach

Settle’s methodology fails in specific contexts. Knowing these prevents forcing his style where it doesn’t fit.

Don’t use daily emails if you can’t sustain them for years.

The power of Settle’s approach comes from compounding consistency. Three weeks of daily emails followed by burnout and silence is worse than steady weekly emails. If you can’t commit to daily for the long haul, don’t start.

For sustainable frequency, see email philosophy decoded.

Don’t use his casual style for B2B enterprise or regulated industries.

A healthcare company can’t write “why I hope you unsubscribe” emails. A B2B SaaS selling to Fortune 500 procurement can’t sound like a guy ranting from his home office.

Settle’s voice works for entrepreneurs, coaches, and info-product businesses. It doesn’t work for contexts requiring institutional credibility. For professional direct response, adapt the principles without copying the tone.

Don’t use anti-swipe-file philosophy if you’re still learning fundamentals.

Settle can write without templates because he’s internalized principles through decades of practice. Beginners who skip templates don’t become original—they become lost.

Learn the formulas first. Practice them until they’re automatic. Then you’ve earned the right to improvise. See PAS formula for foundational structure.

Don’t use his approach with a small, cold list.

Daily emails to 50,000 loyal subscribers generates different results than daily emails to 500 people who barely remember signing up. The math doesn’t work the same.

Build list size and relationship first. Prove you’re worth daily attention through occasional valuable content. Earn the right to show up daily before demanding it.

Don’t celebrate unsubscribes if list growth is slow or expensive.

Settle treats unsubscribes as list cleaning. But if you’re paying $5 per subscriber through ads and losing 10% monthly, you’re just burning money.

The “let them leave” philosophy works when replacement is easy. When growth is constrained, retention matters more than Settle’s approach acknowledges.

Related Practitioners

Gary Halbert — Settle’s primary influence. The A-pile concept, story-driven copy, and anti-corporate voice all trace to Halbert.

Dan Kennedy — Another major influence on Settle’s business model and no-nonsense positioning.

Frank Kern — Similar casual style but different application. Kern focuses on launches; Settle on daily consistency.

Email philosophy decoded — Deep dive on what works and doesn’t from Settle’s approach.

What Settle doesn’t tell you — The hidden requirements behind his success.

The Bottom Line

Ben Settle’s contribution is demonstrating that consistency and authenticity can outperform optimization and sophistication. His daily email practice, print newsletter model, and infotainment philosophy offer a genuine alternative to mainstream marketing advice.

But his approach requires specific conditions: strong voice, long-term commitment, appropriate audience, and sustainable list growth. Without these, his tactics produce burnout and list destruction.

Study Settle for the principles: relationship over broadcast, entertainment as value, consistency as strategy, voice as differentiation. Apply them in your own sustainable way rather than copying his specific implementation.

The practitioners who learn most from Settle are those who understand he’s describing his own path—not prescribing a universal system.

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