Ben Settle's Email Philosophy: Extracting the Signal from the Noise

Ben Settle is one of the most polarizing figures in email marketing.

His philosophy: send daily emails, be unapologetically yourself, never apologize for selling, and let the unsubscribes flow.

Some marketers swear by it. Others think it’s irresponsible advice that burns lists and alienates customers.

The truth? Both camps are partially right. Settle teaches principles that work brilliantly in certain contexts—and fail spectacularly in others.

Here’s how to extract the signal from the noise.

The Core Settle Philosophy

For those unfamiliar, here’s what Ben Settle advocates:

Daily emails: Send every single day. Consistency builds habit and relationship.

Entertainment first: Be interesting. Boring emails get deleted and forgotten.

Personality-driven: Write like yourself, not like a corporation. Let your quirks show.

Sell without apology: Every email should sell something, directly or indirectly. Don’t be shy about it.

Let them leave: Unsubscribes are good. They clean your list of people who won’t buy.

Anti-templates: Don’t follow formulas. Write from the hip. Sound human.

These principles have made Settle wealthy and built a devoted following. But they’ve also led countless imitators into trouble.

---

Want to build a content system that feeds your email? Get the free training—it shows you how to create content that converts, including email.

---

What Works Brilliantly

1. The Relationship Model

Settle’s core insight: email is a relationship medium, not a broadcast medium.

Most marketers treat their list like a billboard—post messages and hope someone reads. Settle treats it like a friendship where you show up consistently.

Why it works:

Regular contact builds familiarity. Familiarity builds trust. Trust makes selling easier.

When you email daily, you’re top of mind when they’re ready to buy. When you email monthly, they’ve forgotten you exist.

How to apply:

You don’t have to email daily. But you do need consistency. Weekly minimum, same day each week, reliable as clockwork.

The relationship model works regardless of frequency—as long as you’re consistent.

2. Entertainment as Utility

Settle argues that being entertaining is itself valuable. People want to be amused. Give them that, and they’ll keep opening.

Why it works:

Attention is the scarcest resource. If your emails are genuinely enjoyable to read, you’ve delivered value before you’ve sold anything.

Entertainment also differentiates. Most business emails are boring. Be the one that’s actually fun to read.

How to apply:

Entertainment doesn’t mean jokes or gimmicks. It means:

• Interesting perspectives
• Stories that pull people in
• Unexpected connections
• A voice that’s distinctive

See how to turn your blog into a sales funnel for more on value-first content.

3. Personality as Positioning

Settle’s writing is unmistakably him. You could pick it out of a lineup. That voice is a moat competitors can’t copy.

Why it works:

In commoditized markets, personality differentiates. When everyone offers similar services, you become the product.

Strong personality also attracts true fans while repelling poor fits. That’s efficient marketing.

How to apply:

You don’t need to be abrasive or controversial (though Settle often is). You need to be distinctive.

What opinions do you hold that others don’t? What’s your unusual take on your industry? What would make your emails unmistakably yours?

4. The Permission to Sell

Many marketers are apologetic about selling. “Sorry to bother you, but…” or “I hate to be salesy, but…”

Settle says: never apologize for selling. You’re providing value. Selling is serving.

Why it works:

Apologizing undermines your offer. If you seem embarrassed about it, why should they want it?

Confidence in your offer transfers to the reader. Sell like you mean it.

How to apply:

This doesn’t mean aggressive or pushy. It means unapologetic.

State your offer clearly. Explain why it’s valuable. Make the CTA direct. Skip the hedging and qualifiers.

What Doesn’t Work (For Most People)

1. True Daily Emails

Daily emailing works for Settle because he’s built a persona around it, has decades of material to draw from, and his audience expects it.

Why it fails for most:

• Quality drops when you force daily output
• Most businesses don’t have enough to say daily
• It can feel spammy in professional contexts
• Burnout kills consistency (which matters more than frequency)

What to do instead:

Find your sustainable frequency. For most businesses, that’s 1-3 emails per week. Consistency beats frequency.

See what Ben Settle doesn’t tell you about daily emails for the hidden requirements.

2. The Abrasive Persona

Settle’s writing is often combative, dismissive of criticism, and deliberately polarizing. That works for his brand.

Why it fails for most:

Most businesses can’t afford to alienate large portions of their audience. Settle can because he’s a one-person business with low overhead.

Abrasiveness also doesn’t fit every personality. Forcing it feels fake.

What to do instead:

Be distinctive without being abrasive. Have strong opinions without being dismissive. The goal is memorable voice, not conflict for its own sake.

3. The Anti-Template Stance

Settle is famously anti-formula. He mocks marketers who follow templates and advocates “writing from the hip.”

Why it fails for most:

Templates exist because they work. Formulas capture proven patterns. Beginners especially need structure before they can improvise.

“Write from the hip” is advice for someone with 20 years of experience, not someone starting out.

What to do instead:

Learn the formulas. Practice them until they’re internalized. Then you can improvise. Masters know the rules before breaking them.

See Hook-Story-Offer: when it works and when it doesn’t for framework application.

4. Letting the List “Clean Itself”

Settle celebrates unsubscribes. “Good riddance” to people who can’t handle his style.

Why it fails for most:

When list growth is slow or expensive, every subscriber matters. Deliberately provoking unsubscribes is a luxury not everyone can afford.

Some unsubscribes are people who would have bought later. Not everyone on a “buyers list” had timing align with your first few emails.

What to do instead:

Accept unsubscribes as natural—but don’t manufacture them. Let people self-select through quality and relevance, not through provocation.

The Hidden Context

Settle’s advice works for Settle because of context most people lack:

He’s been doing this for decades. His “writing from the hip” draws on thousands of emails written. That’s not beginner advice.

He sells information about email marketing. His daily emails are the product demonstration. Every email proves his competence.

His audience expects it. People who subscribe to Ben Settle know what they’re getting. Selection bias creates a receptive audience.

He has no boss, no board, no brand guidelines. Solo business owner saying what he thinks. Most people have constraints he doesn’t.

He can be wrong. If an email flops, he’ll send another tomorrow. Low stakes create space for experimentation.

Understanding this context helps you adapt his principles rather than blindly copying his tactics.

The Principles Worth Keeping

Strip away the specific tactics, and Settle teaches fundamentals that work for everyone:

Consistency matters more than perfection. Regular communication builds relationship. Sporadic brilliance doesn’t.

Your voice is an asset. Develop it deliberately. Make your writing recognizably yours.

Don’t hide from selling. If you’re providing value, selling is a service. Be direct about it.

Entertainment has value. Interesting is better than purely informative. People remember what they enjoyed.

Some people aren’t your customers. Not every unsubscribe is a failure. Fit matters more than list size.

These principles work at any frequency, in any industry, with any level of abrasiveness (including zero).

The 2025 Application

Here’s how to apply Settle’s philosophy to modern content marketing:

Find Your Voice

Not his voice. Yours. What makes your perspective distinctive?

• What opinions do you hold that your industry doesn’t?
• What stories only you can tell?
• What would make your content unmistakably recognizable?

Write more like that. Less like everyone else.

Set Sustainable Frequency

How often can you email without sacrificing quality or burning out? That’s your frequency.

Weekly? Great. Twice weekly? Fine. Daily? Only if you can actually sustain it for years.

Consistency is the variable that matters most.

Value + Sell

Every email should do both. Value makes them open the next one. Selling converts the ready ones.

Don’t separate “value emails” and “sales emails.” Integrate them. Teach something, then offer the next step.

Build Your Own List Philosophy

Your list, your rules. Maybe you’re warm and welcoming. Maybe you’re tough-love. Maybe you’re academic and precise.

Whatever your style, own it. Consistency of voice builds trust, regardless of what that voice sounds like.

The Meta-Lesson

Ben Settle built a career by being Ben Settle. The lesson isn’t to copy his tactics—it’s to develop your own with similar intentionality.

What works for him works because of who he is, who his audience is, and what he sells.

Your situation is different. Your approach should be too.

Take the principles: consistency, voice, value, directness about selling. Apply them in your way, to your audience, for your offers.

That’s what Settle actually did. He didn’t copy anyone else’s playbook. He created his own.

Your job is to do the same.

Related Reading

• What Ben Settle Doesn’t Tell You About Daily Emails — The hidden requirements behind his success
• What Joanna Wiebe Gets Right (That Most Copyhackers Students Miss) — A different approach to copy mastery
• What All the Copywriting Legends Agree On — The universal principles that transcend any guru

Explore more lessons from the masters: The Copywriting Legends.

---

Ready to build your content system? See the Blogs That Sell system—it shows you how to create consistent content that converts, in your voice.

Or start with the free training to get the core framework.