10 Email Copywriting Rules You Should Break in 2026

<p>Everyone&#39;s copywriting &quot;rules&quot; are recycled from 1960s direct mail and copywriting Twitter . In this episode, Jimmy Kim and Chase Dimond go through 10 sacre copywriting rules and explain why most of them no longer hold up in 2026 inboxes and beyond.From why long-form email is quietly outperforming short copy, to why the &quot;one CTA per email&quot; rule is only half right, to why first name personalization barely moves the needle anymore, this episode breaks down what actually converts vs. what copywriters keep repeating because everyone else does.What they cover:- Why long-form email copy is winning (and how AI changed the math)- The real rule behind CTAs: one goal, not one button- Why personalization tokens are overrated and segment-level relevance wins- Statement hooks vs. question hooks- Why most brand storytelling in email is wasted space- The most under-optimized line in your email (hint: it&#39;s not the subject line)- Why the PS line still converts and nobody uses it- Why trying to be funny in email usually backfires- Why fake urgency has trained your customers to ignore you- Writing email copy like you&#39;re texting a friend, not presenting to a boardThank you our friends at Omnisend and Retention.com for sponsoring the podcast!Omnisend is an all in one eCommerce email and SMS marketing automation platform that enables marketers to engage customers and drive sales through personalized experiences. https://www.omnisend.com/sendit/Retention.com helps ecommerce brands turn anonymous website visitors into opted-in email subscribers, making it easy to grow your list with flexible, pay-as-you-go pricing. https://Retention.com?utm_source=send_it&amp;utm_medium=podcastLet&#39;s hang out IRL! Want to spend two days learning alongside some of the smartest operators in ecom? Join us at Commerce Roundtable in San Diego on September 21-22 for tactical sessions, great conversations, and networking that actually leads somewhere. Use code SENDITVIP to save 40%. https://www.commerceroundtable.comeCom Email Certified is a hands-on, results-driven program with a step-by-step guide to mastering retention marketing and driving serious results. Access over 25 hours of learnings and become a certified email &amp; SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/______02:59 Hot Take 1: Long Copy06:46 Hot Take 2: Goal12:09 Hot Take 3: Personalization15:24 Hot Take 4: Question Hooks18:15 Hot Take 5: Storytelling21:20 Hot Take 6:The first line matters more than your headline25:02 Hot Take 7: PS Line Comeback28:21 Hot Take 8: Stop Trying Humor31:38 Hot Take 9: Urgency Overuse Trap36:29 Hot Take 10: Write Like You Text38:21 AI Makes It Corporate39:57 TLDR Wrap______Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, &amp; exclusive industry news! http://ecomemailmarketer.com/#emailmarketing #copywriting #ecommerce #retentionmarketing #klaviyoSend It! is the podcast where Jimmy Kim and Chase Dimond break down everything retention marketing: email, SMS, and ecommerce growth.Subscribe for new episodes every week.______Follow Jimmy &amp; Chase on social!Follow Jimmy Kim at: https://x.com/yojimmykimhttps://www.linkedin.com/in/yojimmykim/https://www.instagram.com/yojimmykim/https://www.tiktok.com/@yojimmykim Follow Chase Dimond at: https://x.com/ecomchasedimondhttps://www.linkedin.com/in/chasedimond/https://www.instagram.com/chasehunterdimond/https://www.tiktok.com/@chasehunterdimondContact us at hellosenditpodcast@gmail.com for sponsorships, appearance requests, interviews, or general information!</p>