Send It!

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!

No matter how good your abandoned cart emails are, most of that lost revenue never comes back. What if an AI could just call and ask why?In this episode of Send It, Jimmy and Chase talk with Will Nauseda, founder of Outcraft about the retention channel almost no one is using: voice. Outcraft built an AI that calls abandoned-checkout shoppers and has real conversations, answering the questions email and SMS can't. They get into why AI voice finally sounds human, why a call often recovers the sale without a discount, where it fits in your flow, what it actually costs, and why the early-mover advantage looks a lot like SMS three years ago.Find Will and Outcraft:Outcraft: https://www.outcraft.ai/?utm_source=Podcast&utm_medium=SendItWill Nauseda: https://www.linkedin.com/in/will-vilius-nauseda-a10278b1/Here's what they get into:- Why voice is the overlooked fifth retention channel- How AI voice got good enough to feel human, while staying disclosed- Why a call often recovers the sale without a discount- Where voice fits in your abandoned-checkout flow, and the quiet-hours rules- What it actually costs, priced per profile instead of per callThank 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.comUpPromote is the #1 affiliate & referral marketing platform on Shopify, trusted by 250,000+ merchants and have tracked over $2 billion in affiliate-driven revenue. Podcast listeners get 30% off for 3 months, applied automatically when they sign up through this link: https://partners.secomapp.com/apps/up_promote/CHASE/b0957000a616 ______00:00 Welcome to the show02:14 Meet Will Nauseda and the Outcraft story07:17 The abandoned cart intent email misses12:23 Breaking down a real AI voice call18:33 Where voice fits in your flow24:45 Why aggressive cart recovery wins26:31 The risks and guardrails of voice32:24 The low-risk way to test it35:10 The omni-channel, conversation-first philosophy38:33 Wrapping up and the future of voice40:16 Final thoughts and what to comment below______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!

(Free download) Ready Made Demand: The Retention Marketer's Guide to Cashing in on The Calendar - https://ecomemailmarketer.com/ready-made-demandRight now your customers are rebuilding their whole routine, and almost no brand is marketing to it.In this episode of Send It, Jimmy and Chase break down how to own a seasonal moment even if you've never sold a school supply in your life. Using back to school as the case study, a $147 billion season and the second biggest of the year, they lay out what actually makes a "moment," the framework for attaching your brand to one without it feeling forced, and the five plays that turn it into revenue. EP 94: The $147B season you're ignoringHere's what they get into:- Why back to school is a mindset, not a date, and the second New Year for your list- The three things that make a moment worth stealing- The stretch test for attaching your brand without it feeling forced- The five plays: bundles, routine stories, segmentation, urgency, and offers- The timing calendar, and why the moment already started back in JulyThank 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.comUpPromote is the #1 affiliate & referral marketing platform on Shopify, trusted by 250,000+ merchants and have tracked over $2 billion in affiliate-driven revenue. Podcast listeners get 30% off for 3 months, applied automatically when they sign up through this link: https://partners.secomapp.com/apps/up_promote/CHASE/b0957000a616______00:00 Welcome to the show03:14 Why this $147B moment matters right now04:22 What actually makes something a moment06:40 How any brand plays the routine reset11:27 The three-question framework for any moment12:58 The five plays that turn a moment into revenue18:31 Why the moment beats a discount19:32 The timing calendar, and why July already started it23:58 The metrics that tell you it actually worked24:47 Key takeaways and your low-risk first move26:13 Final thoughts and what to comment below______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!