Ben Settle is a convicted felon (a story he does not hide, using it as a badge of honor). He is an anti-guru. He famously refuses to "grow" his business beyond a certain size because he values his time and sanity over chasing an extra zero in his bank account. His clients range from supplement sellers to B2B consultants to adult entertainment moguls.
Instead, the early issues introduce the concept of "Infotainment"—a calculated blend of information and entertainment.
The core takeaway of the early Email Players era is simple: build a clean list of people who align with your worldview, show up in their inbox every single day without fail, entertain them thoroughly, and never apologize for pitching your products or services.
Settle shares his formulas for blind curiosity subject lines. The goal of the subject line is not to sell the product; it is strictly to get the email opened. Ben Settle - Email Players 1 - 15
"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."
"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."
An entertaining story is useless if it doesn't sell. This block of issues focuses on the hardest part of email copywriting: . Ben Settle is a convicted felon (a story
: "Psycho-analysis" of real emails to show why certain subject lines and hooks convert while others fail.
Stop relying on automated "Welcome sequences." Turn them off. Instead, commit to 30 days of daily manual emails. Use current events, grudges, and customer wins as your content.
Because they are fun to read, people don't mind being sold to. His clients range from supplement sellers to B2B
: Moving from weekly to daily emails to build deeper connections and explosive authority.
When Settle launched Email Players in 2016, the idea of a physical newsletter about digital marketing seemed backwards. But that’s the point. Mailed copies ensure no algorithm, spam folder, or “promotions tab” gets between Settle and his readers. Issues #1–15 were written during what Settle calls his "pure napalm period"—less polished, more provocative, and packed with raw case studies from his own consulting clients.
: 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
The very first issue opens with a firecracker: "You want people to unsubscribe." Settle argues that trying to keep everyone on your list dilutes your message. He teaches the "Pre-emptive Unsubscribe"—putting controversial statements in your subject line to scare off time-wasters. The lesson: A smaller, rabid list of buyers is worth 10,000 tire-kickers.