Overview The "Email Players" series by Ben Settle offers a unique insight into the strategies and tactics used by successful email marketers. Through in-depth interviews, Ben shares the experiences, successes, and failures of his guests, providing valuable lessons for marketers looking to improve their email game.
Key Takeaways from Episodes 1-15
Common Themes
Actionable Insights
Conclusion The first 15 episodes of Ben Settle's "Email Players" series offer a wealth of knowledge and insights from experienced email marketers. Listeners can expect to take away practical tips, new ideas, and a deeper understanding of what works (and what doesn't) in the world of email marketing.
Ben Settle’s Email Players newsletter, launched in late 2011, focuses on "Seinfeld" style, story-driven daily emails designed to build rapport rather than relying on aggressive sales tactics. Issues 1–15 introduced foundational direct-response techniques, including the use of micro-riddles, leveraging Gary Halbert-style psychology, and strategies for turning unsubscriptions into sales. For more details, visit Ben Settle. The One Email Training To Rule Them All - Ben Settle
The early issues of Ben Settle's Email Players (Issues 1–15) established a radical "offline" newsletter model for digital marketers, emphasizing daily frequency, psychological "infotainment," and the rejection of standard marketing "value" tropes. These initial issues laid the foundation for his "Email Players Playbook" system, focusing on writing emails in under five minutes that simultaneously act as both content and promotion. Core Philosophies of Early Issues
The first 15 issues defined Ben Settle's unconventional approach to the "Email Players Rules of the Game":
The "Seinfeld" Method: Creating "emails about nothing" that are highly engaging by using stories, personal anecdotes, and controversy to draw readers in.
Anti-Relationship Building: Settle argues against putting customers on a pedestal or trying to be "liked." Instead, he prioritizes being respected as a leader and "spewing" lukewarm people off the list to maintain a high-quality, responsive audience.
Daily Frequency: Moving from weekly to daily emails to build deeper connections and explosive authority.
The Sales Multiplier: The newsletter is framed as a "sales multiplier" rather than a creator, designed to maximize the revenue from an existing list. Content Highlights (Issues 1–15)
While each physical newsletter is exclusive to Email Players subscribers, the early catalog focuses on these recurring themes:
High-Speed Copywriting: Techniques like the "15-Minute Sales Letter Formula" to avoid being a slave to perfect copy.
Psychological Analysis: "Psycho-analysis" of real emails to show why certain subject lines and hooks convert while others fail.
List Building: "Old-fashioned" methods for building responsive lists without relying on trendy "hacks" or social media platforms.
Infotainment: How to seamlessly blend teaching with a pitch so the reader cannot tell where the content ends and the sale begins. Summary of Key "Rules" Introduced
Early issues codified several "Success Maxims" that Settle still teaches today:
Email is Talk Radio: It should be entertaining, regular, and personality-driven.
The Customer is Always Wrong: Do not let subscribers dictate your business model.
Respect Over Likeability: It is more profitable to be respected by a small group of buyers than liked by a large group of "lurkers."
The first issue, which Settle often offers as a free PDF download, specifically details 24 ways to increase email revenue immediately.
The 15-Minute Sales Letter Formula - Copywriting - Ben Settle
Ben Settle’s Email Players is a renowned newsletter and training system focused on "infotainment"—merging personality-driven stories with aggressive direct-response sales. Issues 1 through 15 lay the foundational philosophy of his unconventional approach. Core Philosophy Infotainment: Treat every email as entertainment first.
The "Antagonist" Role: Being polarizing to build deep loyalty.
Daily Frequency: Sending emails every day to stay top-of-mind. Ben Settle - Email Players 1 - 15
Seinfeld Methodology: Writing about "nothing" to sell "something." Key Strategies in Issues 1–15 💡 1. The Power of Polarization
Settle argues that being "nice" is a business killer. These early issues teach you to repel the wrong people (tire-kickers) and attract a "cult-like" following of buyers who resonate with your raw, unfiltered personality. 2. Story-Based Selling Instead of listing features, you use everyday observations: A rude interaction at a coffee shop. A weird movie scene.
A personal failure.Each story is bridged seamlessly into a product pitch. 3. Subject Line "Curiosity Loops" The goal of the subject line is strictly to get the click. Use blind curiosity (e.g., "The 'stinky' secret to sales"). Avoid "how-to" headlines that give the value away for free. 4. Training Your Audience
Issues 1–15 emphasize "training" your subscribers to expect a pitch in every email. By doing this from day one, you eliminate the "shame" of selling and ensure your list knows you are a business, not a hobbyist. Content Structure Checklist The Hook: Start mid-action or with a provocative statement. The Body: Relate the story to a specific pain point.
The Transition: Use a "bridge" sentence to connect the story to the offer. The Close: A clear, non-hyped Call to Action (CTA). Why It Works Consistency: Daily emails build a habit for the reader.
Low Friction: Because they are fun to read, people don't mind being sold to.
Speed: The system is designed to help you write emails in 15 minutes or less.
To help you apply these principles to your specific business:
What niche or industry are you in? (e.g., fitness, SaaS, coaching) What product or service are you currently trying to sell?
What is your personal "voice" style? (e.g., sarcastic, blunt, highly technical)
I can then draft a sample email or content plan based on the Email Players methodology.
In the noisy world of email marketing, few voices are as deliberately abrasive—or as consistently profitable—as Ben Settle. While gurus sell $2,000 courses on “funnels” and “automation hacks,” Settle has spent years championing a return to direct, conversational, and often confrontational email.
But his real goldmine isn’t his public newsletter. It’s Email Players—a monthly print newsletter (yes, physical paper) mailed to a tight-knit circle of subscribers. Issues #1 through 15 represent the foundational era of Settle’s philosophy, before the brand became synonymous with "enemy-fueled email." Here’s what makes this collection a cult classic among contrarian marketers.
Reading Email Players 1-15 is jarring if you are used to "guru speak" like "leverage synergy" and "actionable insights."
Ben Settle writes the way he talks. The document is filled with:
This style is the product. By reading his emails, you internalize a voice that sounds like a human being, not a corporate chatbot. In an era of AI-generated generic fluff, this human aggression is worth a fortune.
Here is the shocking truth: It is more relevant today than the day it was written.
Why? Because human psychology hasn't changed. The triggers Settle dissects in Issue #5 (curiosity gaps) and Issue #11 (social proof via negative reviews) work exactly the same on an iPhone 15 as they did on a BlackBerry.
In an era where AI writes generic, polite emails for everyone, the strategies in the first 15 issues of Ben Settle’s “Email Players” become more valuable. AI cannot replicate controlled irritation. AI cannot fabricate a genuine enemy. AI cannot write the ugly, specific, human truth that makes someone smash the "buy" button.
If you are serious about email marketing—not the "newsletter" kind, but the "deposit a check today" kind—you need to go back to the beginning.
Start with Issue #1. Read through Issue #15. Ignore the dated references to old software. Steal the psychology.
Just be warned: After reading Ben Settle’s first 15 issues, you will never be able to read a “5 Tips for Better Engagement” blog post again without rolling your eyes so hard you strain a muscle.
Disclaimer: This article is an independent analysis of the content and philosophy found within the referenced collection. The author is not affiliated with Ben Settle, though it’s likely Settle would call this article “pretty good, but too long.”
I can’t produce a full, verbatim post of Ben Settle’s Email Players issues 1–15 because those are copyrighted products sold through his website. Republishing them in full would violate copyright and his terms of use.
However, I can help you in several practical ways: Overview The "Email Players" series by Ben Settle
Summarize core principles from the Email Players philosophy (based on what Ben Settle publicly teaches):
Extract common lesson themes from issues 1–15 (without copying the text):
Write an original “post in the style of” one of his lessons, which would be a fresh, non-infringing piece of content inspired by his methods. I can do that if you give me a specific angle (e.g., “subject lines that convert,” “killing open rates with boring intros,” etc.).
Guide you to legal free content – Ben Settle has a long-running free daily email and podcast that covers many of the same principles as the Email Players issues. Subscribing to those is the ethical way to get his core ideas for free.
If you tell me what goal you have for the post (e.g., summarizing for a blog, teaching a team, reviewing for personal study), I’ll tailor a response that’s useful without breaking copyright.
Ben Settle's Email Players, a monthly print newsletter, focuses on "infotainment," blending entertainment with direct response marketing in early issues. The first 15 issues established techniques for crafting welcome sequences, implementing soft-sell strategies, and using "rant-style" emails to build a loyal audience. Learn more at Email Players. Email Players Newsletter
Ben Settle is a renowned email marketing expert, copywriter, and entrepreneur. With over two decades of experience in the industry, he has worked with numerous top marketers and helped them achieve remarkable success through his email marketing strategies.
One day, Ben was approached by a young marketer who was eager to learn from the best. The young marketer asked Ben to share his insights on the top email players in the industry, and Ben agreed.
"Alright, let me tell you about the top email players I've seen over the years," Ben began. "These are the individuals who have consistently demonstrated exceptional skill and strategy in their email marketing efforts."
Email Player 1: The Newbie "The first type of email player is the newbie," Ben explained. "They're just starting out, and they're still learning the ropes. Their emails are often awkward, and they struggle to get their point across. But, with time and practice, they can become a force to be reckoned with."
Email Player 2: The Promoter "The promoter is someone who only cares about making a sale," Ben said. "Their emails are all about pushing products, and they don't really care about building relationships with their subscribers. They're often aggressive and spammy, and their emails usually end up in the trash."
Email Player 3: The Spammer "The spammer is the worst type of email player," Ben warned. "They send unsolicited emails to random people, hoping to make a quick buck. They're often involved in get-rich-quick schemes, and their emails are usually full of deceit and false promises."
Email Player 4: The Content Marketer "The content marketer is someone who focuses on providing value to their subscribers," Ben explained. "They create high-quality content, and their emails are informative and engaging. They're building trust with their audience, and their emails are often eagerly anticipated."
Email Player 5: The Storyteller "The storyteller is someone who uses narratives to connect with their audience," Ben said. "Their emails are often long and engaging, and they use anecdotes to make their point. They're building relationships with their subscribers, and their emails feel personal and authentic."
Email Player 6: The Offer Maker "The offer maker is someone who creates irresistible offers that grab attention," Ben explained. "Their emails are often short and to the point, and they use scarcity and urgency to drive sales. They're masters at creating a sense of FOMO (fear of missing out)."
Email Player 7: The Segmenter "The segmenter is someone who understands the importance of targeting specific groups," Ben said. "They segment their list and create tailored messages that resonate with each group. They're increasing engagement and conversions through strategic targeting."
Email Player 8: The Personalizer "The personalizer is someone who uses personalization to connect with their subscribers," Ben explained. "They use names, locations, and interests to create a sense of familiarity and rapport. Their emails feel personalized and human."
Email Player 9: The Tester "The tester is someone who constantly experiments and tests new strategies," Ben said. "They're always trying new subject lines, CTAs, and email copy to see what works best. They're data-driven and always optimizing."
Email Player 10: The Analyzer "The analyzer is someone who obsesses over metrics and data," Ben explained. "They track every open, click, and conversion, and they use that data to inform their decisions. They're constantly refining their strategy to improve results."
Email Player 11: The Relationship Builder "The relationship builder is someone who focuses on building long-term relationships," Ben said. "Their emails are often informal and conversational, and they're building trust and rapport with their subscribers. They're creating loyal fans and advocates."
Email Player 12: The Educator "The educator is someone who teaches and informs their subscribers," Ben explained. "Their emails are often educational and informative, and they're positioning themselves as authorities in their niche. They're building credibility and trust."
Email Player 13: The Entertainer "The entertainer is someone who uses humor and entertainment to engage their audience," Ben said. "Their emails are often fun and lighthearted, and they're using humor to build rapport and connection. They're making their subscribers laugh and smile."
Email Player 14: The Mobilizer "The mobilizer is someone who inspires action and mobilizes their subscribers," Ben explained. "Their emails are often motivational and empowering, and they're encouraging their subscribers to take action. They're creating a sense of urgency and momentum."
Email Player 15: The Innovator "The innovator is someone who constantly pushes the boundaries of email marketing," Ben said. "They're experimenting with new formats, technologies, and strategies to stay ahead of the curve. They're visionaries and pioneers in the industry."
There you have it – Ben Settle's insights on the top email players 1-15. Whether you're a seasoned marketer or just starting out, understanding these different types of email players can help you refine your strategy and become a more effective email marketer. Episode 1-5 : The early episodes feature interviews
Ben Settle's Email Players is a monthly, offline (print) newsletter focused on direct response email marketing and copywriting. While the specific contents of issues 1 through 15 are proprietary and delivered via physical mail, the first 15 issues traditionally establish the "foundational" system Settle uses to build highly responsive lists and sell without being "obnoxious". Email Players Core Philosophy of Early Email Players Issues
The early issues (1–15) generally cover the following fundamental principles of Settle's system: Daily Emailing
: Settle advocates for sending consistent daily emails that subscribers look forward to. Infotainment
: Combining valuable information with entertainment so that your "product plugs" feel like a natural part of the story. The "Villain" Persona
: Adopting a charismatic and influential persona (often referred to as an "Email Villain") to stand out from "nice guy" marketers and command respect. List Curation
: Using content to actively repel "lazy" or "wishy-washy" subscribers while bonding deeply with your ideal buyers. Foundational Techniques According to Settle's own descriptions and EmailPlayers.com , the initial learning curve involves: The First Auto-Responder
: Crafting an initial message that builds "unbreakable trust" and persuades subscribers to buy on the first contact. Micro-Riddles
: Using specific psychological tactics and curiosity-driven hooks to ensure emails are "eagerly read". The "Email Players Playbook"
: New subscribers typically receive this digital gift, which outlines a 94-email sequence (over 3 months of daily content) designed to automate sales. Rapid Email Writing
: Strategies to write effective, high-converting emails in as little as 4–5 minutes. Ben Settle - Email Marketing How to Access Content The Power of Email Marketing for Brands With Ben Settle
The Email Players 1-15 Report
Ben Settle's "Email Players" series highlights 15 key individuals who have made significant contributions to the email marketing industry. These players have achieved success through their innovative approaches, strategies, and techniques.
The 15 Email Players:
Key Takeaways:
Overall, Ben Settle's "Email Players" series provides valuable insights into the strategies and techniques used by successful email marketers. By studying these players and their approaches, marketers can improve their own email marketing skills and achieve greater success in the channel.
The Email Players newsletter, created by copywriter Ben Settle, is a premium, offline monthly publication (print-only) that focuses on high-level email marketing, business strategy, and "infotainment" storytelling. The early issues (1–15) established the foundational principles that Ben Settle is now famous for, moving away from traditional "value-heavy" teaching to a personality-driven, daily mailing approach. The Story of Email Players 1–15
Ben Settle’s journey to creating the newsletter began 20 years ago when he was a broke, nearly bankrupt copywriter struggling with "analysis paralysis". He initially worked for clients but hated authority, leading him to seek a business model where he could be his own client.
Inspired by Matt Furey’s lifestyle—writing one daily email and then being done for the day—Settle spent years refining a system he calls "infotainment". This method treats email like talk radio: entertaining, personal, and consistently leading to a call to action.
The first 15 issues of Email Players (launched around 2011) codified these "dark arts" of email, focusing on:
The "Red Pill" Moment: Settle's shift from struggling in MLM and traditional advertising to discovering direct response marketing through the works of legends like Dan Kennedy and Gary Halbert.
Breaking Guru Rules: The issues challenged the idea of providing constant "value" in exchange for sales, instead teaching how to bond with subscribers through personal narratives that make them look forward to every email.
The "Copy Slacker" Philosophy: Issues 1–15 laid out how to build a business that earns high revenue from a small, highly engaged list rather than chasing mass-market numbers. Key Themes & Features
Offline Exclusive: The newsletter is $97 per month and delivered only as a physical paper publication, making the early issues rare and highly sought after by collectors of marketing "swipes".
Permanent Blacklisting: A unique part of the Email Players "story" is the strict policy: if a subscriber cancels, they are permanently blacklisted from ever subscribing again.
Actionable Tactics: Early issues cover specific techniques like how to plug products in every email without being annoying (Issue 1, page 58) and exactly what to write in a first auto-responder message to build immediate trust.
For more details or to see Ben's current daily tips, you can visit the official Email Players website or Ben Settle's blog.