A bad email gets ignored. A bad SMS gets you blocked.

In this episode of Send It, Jimmy Kim and Chase Dimond unpack why SMS keeps falling flat for so many brands and walk through the copywriting formulas that actually convert. The problem isn't the channel, it's that nobody learned how to write for it. With only 160 characters up for grabs, every word has to earn its place, every hook has to land in the first three seconds, and every send has to feel worth interrupting someone's day for. Jimmy and Chase break down the three part structure every high-performing SMS follows, the specific formulas for abandoned cart, replenishment, VIP drops, and flash sales, and the AI prompts they use to write and tighten copy fast.

EP 82: The 160-character masterclass: Writing SMS that actually converts

Here's what we're diving into:

- Why SMS copywriting is a different skill than email and the four constraints that make it harder

- The hook → value → action formula every high-performing SMS follows

- Specific formulas for abandoned cart, replenishment, VIP drops, and flash sales

- The AI prompts they use to generate, compress, and A/B test SMS copy

- The frequency, segmentation, and testing rules that protect opt-out rates

Thank you our friends at Omnisend, Superscale, Retention Roadshow and eCom Email Certified 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/

Superscale is the first AI agent built for social marketing. It connects to your Meta, TikTok, and Google ad accounts, researches your competitors, and turns a single prompt into hundreds of high-converting creatives built on real performance data. Trusted by Taxfix, SumUp, and backed by Creandum. https://superscale.ai/?utm_source=Sendit

Lone retention marketer no more. Meet Chase, Jimmy, & 75+ hands-on marketers at the Retention Roadshow this June. Get tickets 20% off with ROADSHOW20: https://commerceroundtable.com/roadshow?utm_source=send_it&utm_medium=podcast

eCom 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 & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/

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02:57 Why SMS Is Different

03:25 Space And AI Compression

04:43 Context And Attention

05:39 Intimacy And Tone

06:43 Cost Frequency Segmentation

08:02 Hook Value Action Framework

10:48 Putting The Formula Together

13:27 Abandoned Cart Playbook

15:03 Replenishment Timing Texts

16:27 VIP Early Access Drops

17:06 VIP Drop Specifics

17:56 Flash Sale Formula

18:33 Mystery Discount Tests

19:59 AI Prompts For SMS

22:47 Prompt For Shortening

24:02 AI Variations For Testing

25:34 Replenishment Reminder Prompt

27:21 Testing Framework Basics

30:18 Common SMS Mistakes

31:40 Advanced SMS Tips

33:09 Final Recap And Wrap

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Enjoying the pod? Subscribe to The eCom Email Marketer Newsletter for your weekly dose of retention strategy, actionable insights, & exclusive industry news! http://ecomemailmarketer.com/

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Follow Jimmy & Chase on social!

Follow Jimmy Kim at:

https://x.com/yojimmykim

https://www.linkedin.com/in/yojimmykim/

https://www.instagram.com/yojimmykim/

https://www.tiktok.com/@yojimmykim

Follow Chase Dimond at:

https://x.com/ecomchasedimond

https://www.linkedin.com/in/chasedimond/

https://www.instagram.com/chasehunterdimond/

https://www.tiktok.com/@chasehunterdimond

Contact us at [email protected] for sponsorships, appearance requests, interviews, or general information!