What Ben Settle Doesn't Tell You About Daily Emails

Ben Settle sends an email every day. He’s done it for years. He’s built a loyal audience, sold millions in products, and become the poster child for daily email marketing.

So people copy him.

They commit to daily emails. They try to be entertaining. They adopt the irreverent, personality-driven style. They wait for the sales to roll in.

Three weeks later, they’re burned out, their list is shrinking, and they’ve made zero sales.

What went wrong?

They copied the visible output without understanding the invisible system.

The Ben Settle Model (What People See)

From the outside, Settle’s approach looks simple:

1. Send an email every day
2. Be entertaining and opinionated
3. Mention your product at the end
4. Let the right people buy and the wrong people leave

It seems almost too easy. Just show up daily, be yourself, and money follows.

But this surface-level understanding misses everything that makes it work.

What People Miss

1. The Backend Makes the Frontend Work

Settle doesn’t just sell one thing. He has multiple products at different price points, recurring revenue from memberships, and backend offers that multiply customer value.

When someone buys once, they often buy again. And again. The daily emails aren’t just generating new sales—they’re nurturing existing customers toward more purchases.

If you have one product and no backend, daily emails become a lot of work for limited upside. The math doesn’t work the same way.

2. Years of List Building Came First

Settle has a large, loyal list built over many years. His daily emails go to people who already know him, like him, and trust him.

When you’re starting with a small list of people who barely know you, daily emails don’t have the same effect. You’re asking for attention from people who haven’t decided you’re worth it yet.

The strategy that works for a mature list doesn’t necessarily work for a growing one.

3. The “Unsubscribe” Philosophy Requires Volume

Settle famously doesn’t care if people unsubscribe. “Good riddance”—they weren’t buyers anyway.

This works when you have consistent lead flow replacing those unsubscribes. If you’re losing 50 people a day but gaining 100, you’re growing.

If you’re losing 50 and gaining 10, you’re shrinking. The cavalier attitude toward unsubscribes becomes a death spiral.

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4. Entertainment Requires Actual Skill

Settle is genuinely entertaining. His writing voice is distinctive, his opinions are strong, and his stories are engaging.

Most people aren’t naturally entertaining writers. When they try to force it, they produce awkward copy that feels like they’re trying too hard.

Being boring and consistent beats being forced-entertaining and inconsistent. But “just be entertaining” isn’t actionable advice for most people.

5. The Opinions Are Real

Settle has genuine opinions. He’s not manufacturing controversy for engagement—he actually believes what he writes.

When people copy the “controversial opinion” approach without having real opinions, readers sense it immediately. Manufactured controversy is transparent and off-putting.

Strong opinions work when they’re authentic. When they’re calculated, they backfire.

6. The Products Match the Audience

Settle sells to a specific audience: marketers and entrepreneurs who value independence, irreverence, and unconventional thinking. His style attracts exactly those people.

His products are designed for that audience. The email style and the offer are aligned.

If your audience values professionalism, seriousness, or corporate credibility, Settle’s style will repel them—even if your product would serve them well.

The Deeper Problem: Copying Outputs Instead of Systems

The Ben Settle trap is a specific case of a general problem: copying visible outputs instead of understanding the system that produces them.

Settle’s daily emails are an output of:

• Years of list building
• A specific audience attracted to his style
• Multiple products with strong backends
• Genuine personality and opinions
• Consistent lead generation
• Writing skill developed over time

You can’t copy the output and expect the system to magically appear.

What Actually Works About Daily Emails

Daily emails aren’t wrong. But understanding why they work (when they work) matters:

Consistency Builds Trust

Regular contact keeps you top of mind. When someone needs what you offer, they think of you first.

But “regular” doesn’t have to mean daily. Weekly, twice weekly, or three times weekly can build the same trust with less burnout risk.

Personality Creates Connection

People buy from people they like. Showing personality in your emails creates connection that faceless marketing can’t match.

But personality doesn’t require Settle’s specific style. Your authentic voice—whatever it is—works better than a copied voice.

Selling in Every Email Normalizes Buying

Settle mentions his products constantly. This normalizes the idea of buying from him and keeps offers visible.

But you can do this subtly—relevant links, case studies, natural mentions—without the hard-sell approach.

Polarization Filters the Audience

Strong opinions attract the right people and repel the wrong ones. This makes your audience more responsive.

But polarization requires genuine opinions. And it works best when you have enough volume that filtering improves quality rather than eliminating quantity.

A More Sustainable Approach

If you want to learn from Settle without burning out:

1. Start With Frequency You Can Maintain

Daily is great if you can sustain it. But three times a week, consistently, beats daily for three weeks followed by nothing.

Find your sustainable frequency first. You can always increase later.

2. Build Your List Before Relying on Email Sales

Email works best when you have a substantial, engaged list. Focus on list building through content, lead magnets, and audience development.

See how to turn blog readers into email subscribers for strategies.

3. Develop Your Authentic Voice

Don’t copy Settle’s voice. Develop your own. What do you actually believe? What opinions do you genuinely hold? What stories are authentically yours?

Authenticity beats imitation every time.

4. Create Backend Offers

A single product with email marketing has limited upside. Build a product ladder so each customer can buy more over time.

This makes the daily email math work much better.

5. Match Strategy to Audience

If your audience would be put off by irreverent, daily sales emails, don’t send them. Match your email strategy to what your specific audience responds to.

Professional audiences might want fewer, higher-value emails. Casual audiences might enjoy more frequent, lighter content.

The Real Lesson

Ben Settle built something that works for Ben Settle. His style, his audience, his products, his backend—they all fit together.

The lesson isn’t “send daily emails like Ben Settle.” The lesson is: build a system where all the pieces fit together for your situation.

That might include daily emails. It might not. The strategy should serve your goals, not imitate someone else’s outputs.

Study Settle for principles:

• Consistency matters
• Personality creates connection
• Selling is okay
• The right audience beats a big audience

But build your own system. One that fits your voice, your audience, your products, and your sustainable effort level.

Related Reading

• Ben Settle’s Email Philosophy: Extracting the Signal from the Noise — What actually works from his approach
• What Joanna Wiebe Gets Right (That Most Copyhackers Students Miss) — Research-driven copy vs. formula-driven
• The Hidden Assumptions in Classic Copywriting Advice — Why context matters for all guru advice

Explore more lessons from the masters: The Copywriting Legends.

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Ready to build an email system that works for you? See the Blogs That Sell system—it shows you how to create content that nurtures readers into customers, at whatever pace works for your business.

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