Send It!

Download the 100 here: https://ecomemailmarketer.com/sendit-100This week, we’re celebrating episode #100 with a fun 100 things we know about retention.Here’s what we cover in the pod: → Lists and list growth (why size is a vanity metric, and what actually matters instead)→ Deliverability (the habits that quietly protect or destroy your sender reputation)→ Segmentation (why over-segmenting is procrastination in disguise)→ Flows (the automations every brand should have and rarely maintains)→ SMS (the rules that are different from email, and why)→ Copy and creative (what actually gets opens, clicks, and conversions)→ Offers and discounts (why discounting is a tool, not a strategy)→ Strategy and LTV (why retention funds acquisition, not the other way around)→ Metrics (which numbers actually matter, and which ones are just noise)→ Mindset (the operator habits that separate good retention marketers from great ones)Whether you’re brand new to retention marketing or you’ve been doing this for years, there’s something in this list that’s going to challenge how you’re currently running your program.We’re also giving away a free downloadable checklist of all 100 things:.*****Thank you our SPONSORS of the show who allow us to share valuable and free information to you every week: 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&utm_medium=podcastAllan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com/Want to learn more about all things email and sms marketing?Chase and I have a master course: 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/______00:00 Intro00:54 Welcome to 100!02:26 List Growth Truths06:05 Deliverability Essentials08:41 Segmentation That Works11:11 Omnisend is Awesome13:44 Flows Money Machine16:28 SMS Principles Start17:54 SMS Rules Recap18:55 Retention.com is great20:03 Coordinating Email and SMS20:24 Copy and Creative Wins22:09 Unsubscribes and Usefulness22:43 Discounts Without Damage26:21 LTV and Retention Strategy28:49 Allan Personalization is a must try29:56 Metrics That Matter33:07 Operator Mindset Final 1034:48 Wrap Up______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/______Follow Jimmy & 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 [email protected] for sponsorships, appearance requests, interviews, or general information!

Win-Backs Are Broken Because Everyone Treats Them Like One ThingMost brands treat “win-back” like it’s one flow. On this week’s show, Jimmy Kim and Chase Dimond argue that’s the exact reason win-backs underperform almost everywhere, because a win-back is actually two completely different problems wearing the same name.They break down the two buckets every brand needs to separate: the lapsed customer (someone who already bought and proved their intent) and the lapsed prospect (someone who joined your list but never converted). Treating them the same doesn’t just waste a message, it actively hurts both.What we cover:→ Why a lapsed customer deserves patience, not a panic discount→ The ladder approach to winning back customers without training them to wait for a sale→ Why a lapsed prospect’s intent has a shelf life, and why speed matters more than anything→ Why being aggressive with a cold prospect is the right move, not a risky one→ Why unengaged prospects need to be sunset, and how holding onto them hurts your deliverability for everyone else→ How to measure the two buckets differently instead of judging them by the same metricIf your win-back flow is just a single “we miss you” email going out to everyone who’s gone quiet, this episode explains exactly why it’s not working the way you think it is.Thank you our SPONSORS of the show who allow us to share valuable and free information to you every week: 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&utm_medium=podcastAllan helps you run your email marketing program like your ads! Leveraging AI, you can send real personalized 1 on 1 messages based on their behaviors and data. And the best part? it sits on top of your ESP! Try it for free: https://getallan.com/Want to learn more about all things email and sms marketing?Chase and I have a master course: 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/______00:00 Show Intro01:22 Two Winback Buckets04:22 Why Customer Lapse Hurts06:16 Reframe Patience vs Speed08:35 Customer Winback Ladder11:21 Timing by Purchase Cadence12:52 Prospect Window and Decay15:41 Prospect Sprint Playbook17:47 List Hygiene and Deliverability21:43 Stop Hoarding Subscribers23:18 Implementation and Metrics25:23 Wrap Up Key Takeaways______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/______Follow Jimmy & 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 [email protected] for sponsorships, appearance requests, interviews, or general information!

This is the the most Important number in Retention Marketing nobody tracksEvery brand celebrates new customer count. On this week’s episode, Jimmy Kim and Chase Dimond argue that’s the wrong number to be proud of, and that the real moment that determines a customer’s lifetime value is the second purchase, not the first.They break down why a first-time buyer isn’t really a customer yet, just someone willing to give you a chance, and why the shift from trial to identity is the actual psychological threshold every retention program should be built around.What we cover:→ Why repeat purchase probability compounds after the second order, and what that means for your acquisition budget→ The psychological difference between a first purchase (trial) and a second purchase (identity)→ Why discounting the second purchase trains the exact behavior you don’t want→ How to find your product’s natural reorder window instead of guessing→ 5 concrete playbooks for the post-purchase window: post-purchase sequence, replenishment nudge, cross-sell, bounce-back offer, and subscription conversion→ The two numbers almost no brand tracks: cohort-based repeat purchase rate and median time to second orderIf you’ve ever wondered why your acquisition numbers look great but revenue feels flat, this episode explains where the leak actually is.Subscribe for new episodes every week.Thank you our friends at Omnisend 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/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&utm_medium=podcastCreate Emails like Ads: getallan.com 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/______00:00 Intro01:12 New Customers Aren’t Loyal03:29 Why Second Purchase Matters07:03 Trial to Identity Shift08:49 Omnisend Migration Sponsor10:57 Post Purchase Builds Trust13:25 Timing by Category16:19 Retention.com BFCM Sponsor17:29 Email vs SMS Phases19:16 Five Second Purchase Playbooks24:03 Ecom Email Certified Plug25:13 Measure Cohorts and Timing28:10 Wrap Up and Homework#retentionmarketing #ecommerce #emailmarketing #dtc #customerretentionSend It! is the podcast where Jimmy Kim and Chase Dimond break down everything retention marketing — email, SMS, and ecommerce growth.______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/______Follow Jimmy & 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 [email protected] for sponsorships, appearance requests, interviews, or general information!

The Legal Loophole Behind Non-Opt-In Email MarketingIs it actually legal to email people who never opted in? This week, Jimmy Kim sits down with Adam Robinson, founder of Retention.com and RB2B, to break down how identity resolution and non-opt-in email marketing actually work, and why it’s compliant under U.S. law even though most people assume it isn’t.Adam built Retention.com (formerly GetEmails) into the market leader in this space, and in this episode he explains exactly how the legality works, how deliverability actually gets protected, and what separates a smart list growth strategy from one that gets a brand blacklisted.What we cover:→ Why non-opt-in email marketing is legal under CAN-SPAM, and why so many people think it isn’t→ The 1-2% rule that keeps deliverability safe when adding non-opt-in contacts→ Who this strategy actually works for (hint: it’s not a brand new store)→ The difference between Retention.com’s two products: aggressive list growth vs. conservative cart recovery→ Why the biggest Shopify brands use multiple identity vendors at once, not just one→ How Adam priced RB2B at $79/month instead of a $12,000 sales-led deal, and why→ Why events and in-person relationships still drive most vendor decisions in ecommerceIf you’ve been skeptical about identity resolution tools or unsure whether they’re worth the risk, this episode answers the questions most people are too embarrassed to ask.Thank you our friends at Omnisend 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/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&utm_medium=podcastWant 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 & SMS marketer. Use code: SENDIT! for $300 OFF https://www.ecomemailcertified.com/______00:00 Intro00:47 Welcoming our guest01:43 Is this legal? Breaking down CAN-SPAM02:48 Compliance Explained05:22 Deliverability Strategy: The 1-2% deliverability rule07:43 Who Should Use It10:40 Optimization Not Magic12:05 Real World Use Case14:00 Grow vs Reclaim15:46 Competitors Copycats17:50 Data Sources Providers21:28 Events, community, and how this market actually buys23:01 Pricing Shakeup: You lowered the price?26:21 Final questions and outro______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/______Follow Jimmy & 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 [email protected] for sponsorships, appearance requests, interviews, or general information!

Everyone's copywriting "rules" 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 "one CTA per email" 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'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'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&utm_medium=podcastLet'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 & 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, & 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 & 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 [email protected] for sponsorships, appearance requests, interviews, or general information!