Email Marketing Experiments 🧪: Email Marketing Strategies for Business Owners, Service Providers & Freelancers

Dr. Ayebanoa Sapphire Benwari
  • 0.0 (0)
  • Marketing

Email Marketing Experiments was born out of a desire to share behind the scenes of failed and successful email marketing campaigns. What we’ve tried that worked and didn’t work. Instead of thinking it and testing it alone, we also share it. From welcome sequences to sales campaigns, list growth strategies, and more, we test ideas, break down results, and spill the tea. Come join us behind the scenes.

  1. 2d ago

    #61: Inside a 60-Email Choose-Your-Own-Adventure Welcome Sequence with Kristin Lawton

    Most welcome sequences tell people about you. Kristin Lawton's welcome sequence lets people build something with you. Kristin,Chief Brand Mixologist at District Brand Bar, with 20+ years in brand strategy across politics, PR, and nonprofit communications built a 60-email choose-your-own-adventure welcome series where new subscribers "enter the bar," pick a base spirit, flavour, cocktail style, and garnish, and land on a fully custom cocktail recipe by the end. It sounds like a lot of email. It is a lot of email. But her overall click-through rate jumped to 6% after launch , nearly triple what most lists see without any increase in unsubscribes. In this episode, she walks through exactly how it's built, what happens when subscribers don't want to play along, and how anyone (not just a cocktail-themed brand) can build something similar. INSIDE THIS EPISODE 1. Why Kristin built her welcome sequence as an interactive "choose your own adventure" instead of a standard intro series 2.How subscribers' choices (base spirit, flavour, style, garnish) route them down different email paths 3.The "dealer's choice" fallback for subscribers who never make a choice and why it performs just as well 4. The tech stack behind it: Kit (ConvertKit), a Notion tracking database, and heavy use of tagging across dozens of small automations 5. Why she rebuilt her welcome series to "train her audience to click" from the very first email 7. The results: a 6% overall click-through rate post-launch, with open rates and unsubscribes unchanged 8. Her monthly "Mixologist Playbook" newsletter designed to look forward instead of recapping the past 9. An AI-personalised 6-month anniversary email that generates each subscriber a custom cocktail using their first name 10. The email marketing myth she wants to bust: sending just to send is not the same as staying consistent GUEST RESOURCES Guest: Kristin Lawton, Chief Brand Mixologist at District Brand Bar Instagram: https://www.instagram.com/districtbrandbar/ Website: districtbrandbar.com/hello My Quiz: What's Your Signature Brand Marketing Style: https://districtbrandbar.com/quiz EPISODE TIMELINE ⏱️ [03:34] – Kristin's path from politics, PR, and nonprofit communications into brand strategy [05:30] – Building an off-grid cabin during the pandemic (and why she's banned from driving the tractor) [08:20] – Kristin's "job description" for email marketing: keep them ordering another round [09:45] – Her biggest email marketing mistake: a typo in her own brand tagline, sent to her whole list [12:50] – Inside the Choose Your Own Adventure welcome series and how it works [15:48] – The tech behind it: Kit, Notion, and layers of tagging automations [16:43] – How her DISC-based brand style quiz feeds into the sequence [18:44] – Why she scrapped her standard 3–5 email welcome series for something more immersive [22:10] – What happens when subscribers don't make a choice: the dealer's choice path [25:55] – The results: click-through rates jumped to 6% overall after launch [30:39] – How the dealer's choice sequence works on the backend for non-responders [31:51] – Her advice for building a choose-your-own-adventure sequence, even without a themed brand [35:42] – The monthly "Mixologist Playbook" newsletter and why it looks forward, not back [40:55] – The AI-personalised 6-month anniversary email that builds a custom cocktail from a subscriber's name [46:02] – A common mistake someone who's just starting out can make when using this strategy [51:41] – The email marketing myth she wants to bust, and the sender-name mistake that's an instant unsubscribe [53:51] – Rapid fire: long vs. short emails, open vs. click rates, branded vs. plain-text design CONNECT WITH US Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

  2. Jul 27

    #60: How to Improve Email Open Rates and Click Rates Through Real Email Marketing Experiments with Tayler Cusick Hollman

    Most email marketers are searching for the perfect strategy to increase their open rates and click rates. Tayler Cusick Hollman believes they're asking the wrong question. In this episode, marketing consultant, educator, and founder of the marketing platform Enji shares the real email marketing experiments she's run inside her own business, from haiku-style emails and engagement-based segmentation to nurture-first campaigns and subject line testing. Some experiments worked, some failed spectacularly, and one still remains an unsolved mystery. If you've ever wondered how to improve your email marketing without relying on guesswork, this episode will show you how to build a culture of testing that leads to better decisions and stronger results. INSIDE THIS EPISODE 1. Why experimentation is one of the most valuable skills every email marketer can develop 2. The surprising haiku email experiment that reduced click rates instead of increasing them 3. Why sending emails only to engaged subscribers caused open rates to drop and why Tayler still can't explain it 4. What happened when she reduced her email frequency to see if fewer emails performed better 5. How a nurture-first email strategy is changing the way she approaches sales campaigns 6. How to decide what to test in your email marketing based on your business goals 7. Why looking for patterns in your email analytics leads to better marketing decisions 8. The difference between marketing a SaaS product and marketing a service through email 9. Why founders should segment subscribers by the problems they're trying to solve,not just demographics 10. The welcome sequence and onboarding automation every SaaS business should have 11. The email marketing mindset that keeps Tayler testing, even when experiments fail GUEST RESOURCES Guest: Tayler Cusick Hollman Instagram: https://www.instagram.com/enji_co/ Website: https://www.enji.co/ EPISODE TIMELINE ⏱️ [01:37] – Meet Tayler Cusick Hollman and the story behind Enji [08:04] – What role email marketing plays inside her business [09:05] – Open Rates Confession: accidentally sending an email before a feature launched [11:16] – Why email marketing experiments matter [12:39] – The haiku email experiment that hurt click rates [14:00] – Why sending only to engaged subscribers unexpectedly lowered open rates [20:31] – Testing fewer emails versus sending more frequently [21:47] – Building a nurture-first email strategy before pitching [24:09] – Why curiosity and resilience make better email marketers [26:29] – How Tayler decides what to test next [31:11] – Email marketing for SaaS versus service businesses [34:13] – New email campaign ideas and customer case studies [41:23] – Advice for founders launching SaaS products [45:41] – Rapid Fire: campaigns, automations, segmentation, and email marketing opinions [49:51] – Where to connect with Tayler and learn more about Enji CONNECT WITH US Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

  3. Jul 20

    #59: Small List, Real Revenue: How Andi Smiley Uses Email & Pinterest to Sell Her Offers Without Sales Calls

    Most people believe they need a massive email list before email marketing starts generating meaningful revenue. Podcast coach Andi Smiley believes the opposite. In this episode, Andi shares how she filled every spot in a brand-new offer using a relatively small email list, two emails a week, and zero sales calls. She also explains why storytelling, not hard selling, has become the foundation of her email strategy, how Pinterest quietly drives podcast growth, and why consistency matters more than having thousands of subscribers. If you've ever wondered whether your email list is "too small" or worried about emailing people too often, this conversation will completely change the way you think about email marketing. INSIDE THIS EPISODE 1. Why a small email list can generate meaningful revenue 2. How Andi filled a brand-new offer without using sales calls 3. The mindset shift that helped her start emailing twice a week 4. Why storytelling makes sales emails feel natural instead of pushy 5. How many emails people usually read before making a buying decision 6. Why unsubscribes aren't always a bad thing 7. The simple email system Andi uses to stay consistent every week 8. How Pinterest helps grow her podcast, website traffic and email list 9. Why podcast episodes should have only one call-to-action 10. The metrics Andi actually pays attention to and the ones she worries about less today GUEST RESOURCES Guest: Andi Smiley Threads: https://www.threads.com/@friendlypodcastguide Podcast: https://friendlypodcastguide.com/friendly-podcast-guide-links/ Free Resource: Is Pinterest Right for Your Podcast? Checklist: https://friendlypodcastguide.com/is-pinterest-right-for-me-checklist/ EPISODE TIMELINE ⏱️ [01:44]- Meet Andi Smiley and how she manages to read six to seven books every month. [05:48]- From radio producer to podcast coach: Andi's journey into podcasting. [08:48]- Why email marketing is the biggest revenue driver in her business. [11:04]- Open Rates Confession: Why she was afraid to send more than one email a week. [14:28]- The strategy that filled every spot in her new Pinterest VIP offer. [19:04]- Why separating podcast emails from sales emails changed everything. [22:49]- Keeping readers interested while promoting the same offer for over two months. [25:44]- About her checklist for podcasters who want to use Pinterest [28:14] Why Andi stopped trying to write "perfect" emails and simply became herself. [33:33] The email subject lines and formats that consistently earn opens. [37:17] Her simple weekly system for writing and scheduling emails. [39:51] How Pinterest drives podcast listeners and email subscribers. [45:33] Rapid-fire: favourite metrics, email length, CTAs and tools. [50:35] Andi's advice for anyone struggling to generate revenue from email. Connect with Us Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

  4. Jul 13

    #58: How to Use Data, Personalisation, and Testing to Get Better Results from Every Email Campaign with David Guttman

    Most people treat email marketing as its own separate thing. David Guttman,serial entrepreneur, business strategist, and mentor to CEOs of eight-figure companies says that is exactly the problem. In this episode, the man who has built, scaled, and exited multiple eight and nine figure companies across 40+ industries breaks down the data-driven, persona-led, omni-channel approach that has driven results everywhere from telemedicine to Forex trading firms. And he does it with a live case study built right inside the conversation. If you want to move from guessing what works in your email marketing to actually knowing this episode is where to start. Inside This Episode 1. Why treating email as a standalone channel is one of the most costly mistakes businesses make 2. What persona-driven marketing actually means and how a single image change increased utilization by 35% 3. How to figure out which data points actually change subscriber behaviour and which ones do not matter 4. The difference between strategy and tactics in email marketing and why mixing them up slows everything down 5. Why David tests five things at a time instead of two and how to do it with small lists 6. What a control group is, why you need one, and how to set it up without a data science degree 7. The email marketing myth David wants to bust: more emails is not always better 8. A real case study of an omni-channel campaign built live from scratch during this episode 9. Why you should define what success looks like before you run any test, not after 10. The email marketing horror story that took a $200 million company to zero in 60 days Guest Resources Guest: David Guttman Website: www.guttmanmedia.com Link to the Anti-MBA course:https://www.guttmanmedia.com/anti-MBA NEW: The Email Clinic is open! If this episode got you thinking about your email marketing, imagine having a community where you can get help 24/7. The Email Clinic is where freelancers and service providers come to start, grow, and sharpen their email marketing skills together. Live copy reviews, live training, community chats and more. 👉 Join us here: https://sapphirelearninghub.nestuge.com/ Episode Timeline [02:27] – David's background: 35 years, 40+ industries, 15 businesses bought and sold [07:37] – The role email marketing plays across different businesses and industries [08:27] – Why email should never be treated as a standalone channel [09:46] – Open Rates Confession: the email mistake that took a $200M company to zero in 60 days [12:12] – The telemedicine case study: how persona-driven marketing increased utilisation by 35% [14:48] – What data to actually collect and how to decide which data points change behaviour [18:56] – Building hypotheses and testing them: the ABC to ABCDE approach explained [22:20] – What omni-channel marketing actually means and how many channels you need [23:16] – The two things that matter most in any omni-channel campaign [26:33] – Live case study: building a data-driven omni-channel email campaign for an edtech company [31:11] – The control group explained simply and why you need one in every test [36:36] – Why everything should be automated and why you should never stop testing [40:01] – The biggest mistake people make when testing: not defining success in advance [42:40] – How he uses strategy and testing in email marketing [46:26] – The Anti-MBA Course: what is in it and how to get it free [47:56] – Rapid fire session Connect with Us Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

  5. Jun 30

    #57: Your Newsletter Is a Product, Not More Content: How I Launched and Grew Mine in 7 Days with Onikepo Omotade

    Most people think of a newsletter as just another piece of content to keep up with. Onikepo Omotade,business coach and host of the Grow with Kepo podcast thinks of hers as a product with one specific job: helping her audience turn their annual salary into their monthly salary. That single shift in mindset changed everything. In this episode, she breaks down how she went from years of false starts with email to launching her Paid in Full newsletter in just seven days and the simple, low-effort strategy she used to start filling it with the right people. If you have been overthinking how to start or grow your email list, this conversation will give you permission to simplify everything. INSIDE THIS EPISODE 1. Why treating your newsletter as a product instead of "more content" changes how you write and grow it 2. The one job Onikepo gave her newsletter and why that single decision removed all the guesswork 3. How she went from idea to launch in just 7 days without overcomplicating the tech 4. Why outsourcing the setup to a VA freed her to focus on the one thing that actually mattered 5. The "your network is your net worth" strategy she used to get her first subscribers 6. The simple forward-to-a-friend tactic that quietly grows your list while you sleep 7. What she would do differently if she launched again and why patience with the timeline matters more than perfection 8. Her advice for anyone who feels like the people on their list right now are not their "real" audience yet 9. Why clarity comes from execution, not from overthinking your strategy 10. What she would change if she had to launch her newsletter all over again GUEST RESOURCES Guest: Onikepo Omotade Instagram: https://www.instagram.com/growwithkepo/ Newsletter: Paid in Full- https://onikepo.com/paid-in-full-opt-in You're sitting on Gold Live Webinar: https://link.vyveplus.ai/widget/form/yIwamSQK3LPjcGUhaL4U EPISODE TIMELINE ⏱️ [01:33] – Onikepo's background: strategy consulting, tech, coaching, and a few unexpected detours [04:59] – Introducing the Paid in Full newsletter and what makes it different [07:36] – Why Onikepo decided to take the leap now after years of false starts [08:12] – Treating your newsletter as a product with one specific job [11:26] – Her actual process: from idea to launch in 7 days [15:39] – Keeping the tech simple and outsourcing the setup to a VA [20:56] – Why she stopped stressing about open rates and engagement [22:33] – The "your network is your net worth" strategy for first subscribers [26:29] – What to do if the people on your list are not your real target audience yet [27:05] – The forward-to-a-friend strategy that grows your list passively [30:36] – What she would do differently if she launched again [31:44] – Her plans for adding a community element to the newsletter [34:07] – Her advice for anyone hesitant to start: what's the cost of waiting? [35:19] – About the You're Sitting on Gold workshop and what it covers Connect with Us Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

  6. Jun 22

    #56: How To Grow Your Email List Without Funnels or Freebies with Adam Schaeuble

    In 2025, Adam Schaeuble did something most email marketers would never dare to do. He deleted every funnel and lead magnet he had ever built and started promoting his weekly newsletter as the only opt-in. The result? Over 2,000 new subscribers, a 70% open rate, and a list full of people who actually want his emails. In this episode, the podcasting business coach and host of Podcasting Business School shares the full story, including the content flywheel that powers his podcast, newsletter, and social media without burning out, and the welcome email strategy that gets replies every single time. INSIDE THIS EPISODE 1. Why Adam deleted every lead magnet and funnel he had and what happened next 2. The big difference between people who want your freebie and people who actually want your emails 3. How he maintains a 70% open rate with a 4,000+ person list without clever subject line 4. The content flywheel that powers his podcast, newsletter, and social media without starting from scratch every week 5. The welcome email strategy designed to get replies and clicks and why he only sends one 6. How to sell through email without sending more emails during a launch 7. Why promoting your newsletter every week is not being salesy and how to do it well 8. What his exact Thursday newsletter format looks like from the warm open to the PS 9. How he decides who gets the bonus Monday email and why it works 10. Why podcasters who want to grow their email list need to hear this episode GUEST RESOURCES Guest: Adam Schaeuble Website: https://www.podcastingbusiness.school/ Threads: https://www.threads.com/@podcastingbusinessschool Recommended Episode: Episode 608 -The SEO strategy that helped Adam reach 1 million downloads - https://open.spotify.com/episode/5bC46ZOU0xBZlzLyqQ4AcN?si=On72q7RCS22KD047og-7Yw EPISODE TIMELINE ⏱️ [03:07] – Adam's background: from fitness entrepreneur to full-time podcasting business coach [04:16] – If email had a job description in Adam's business, it would be this [05:29] – Open Rates Confession: the tagging mistake that left an entire list without emails [08:58] – The big pivot: deleting all lead magnets and funnels in 2025 [10:25] – Why your lead magnet attracts people who want the freebie, not your emails [13:03] – How his podcast and newsletter work together without repeating the same content [16:29] – Why people now open his emails based on who it is from, not the subject line [17:45] – The content flywheel: how one piece of content powers weeks of content [22:11] – The bonus Monday email and how he decides who gets it [26:29] – His exact Thursday newsletter format from warm open to PS [31:54] – The welcome email strategy that gets replies and keeps him out of spam [35:28] – What changes and what does not during a launch [38:29] – Why one clear newsletter opt-in beats five lead magnets every time [43:25] – Email marketing myth: do we really need funnels? [47:18] – Advice for podcasters who want to bring email into their content strategy Connect with Us Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

  7. Jun 15

    #55: Black Friday Email Marketing Strategies for Course Creators: with Monica Badiu

    What happens when you do everything right, the segmentation, the re-engagement, the strategy and the results still don't follow? In this episode, Monica Badiu, a conversion strategist, sales copywriter, and email marketing specialist for course creators pulls back the curtain on two of the most revealing email experiments of her career. One Black Friday campaign that came within $5,000 of six figures. And a 1 million-person email list that broke her heart. If you have ever wondered whether segmentation is actually worth the effort, or what to do when a big list produces small results this episode will change how you think about email marketing strategy. INSIDE THIS EPISODE 1. Why sending the same Black Friday offer to everyone was quietly killing this creator's revenue, and what changed when they segmented 2. Why Your Black Friday Campaign Flopped (and How to Fix It with Segmentation) 3. The 3-Layer Customer Research Framework for Highly Profitable Email Launches 4. What a 1 million-person email list with low engagement actually looks like behind the scenes 5. How a re-engagement campaign brought 200,000 inactive subscribers back from the dead 6. Why deliverability alone is not the real problem and what the data actually revealed 7. How to do customer research that gives you real segmentation ideas, not just guesses 8. The email revenue self-assessment tool that tells you exactly where you are leaking money 9. How to Turn Your Email List into a Sales Engine GUEST RESOURCES Guest: Monica Badiu LinkedIn: https://www.linkedin.com/in/monicabadiu/ Website: www.monicabadiu.com Free Resource: https://www.monicabadiu.com/email-revenue-self-assessment/ - this is a self-assessment that identifies the bottlenecks that are impacting email marketing performance. It's based on her experience working with course creators for 6 years. EPISODE TIMELINE ⏱️ [01:13] – Introduction: who Monica is and what she does [2:52] – Monica's background: from SEO and PR to falling in love with email marketing [13:58] – The Black Friday campaign experiment: two years of declining results and what changed [15:04] – How segmentation turned a struggling campaign into 50% more revenue [20:07] – Why there is no secret recipe and how customer research changes everything [23:22] – The three-layer customer research framework: survey, validate, waitlist [26:50] – How to write survey questions that actually give you useful answers [33:59] – What she would do differently looking back [36:41] – How to manage multiple segments without burning out [42:16] – The email revenue self-assessment explained [46:19] – The 1 million-person email list: re-engaging 200,000 inactive subscribers [48:11] – Why the promotion still failed and what the data revealed [50:03] – Email marketing myths Monica wants to bust [52:32] – Rapid fire questions: paid vs free wait-list, building email list organically vs through collaboration, interactive vs community based lead magnets [56:42] – Best email marketing advice for someone just starting out Connect with Us Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

  8. Jun 8

    #54: The Email Marketing Summer Plan with Dr. Sapphire

    Summer is coming and your email list does not have to suffer for it. In this solo episode, Dr. Sapphire breaks down her practical email marketing summer plan for three types of business owners: the ones who want to disappear completely, the ones who want to stay somewhat visible, and the ones who just want to rest without abandoning their audience. Whether you are a mom juggling school holidays and a growing business, or a solopreneur who just needs permission to take a real break, this episode is your plan. INSIDE THIS EPISODE 1. You can take a real summer break without losing your audience and this episode tells you exactly how. 2. How to keep making sales from email while you are completely offline and not even thinking about work 3. The one thing that makes batch writing emails so much easier than most people realize 4. Why telling your list you are going on holiday actually makes them trust you more 5. How to figure out which summer option fits your life right now, not a one-size-fits-all answer RESOURCES Click here to signup for the summer offers👇 sapphirelearninghub.com/services EPISODE TIMELINE ⏱️ [01:13] – Introduction: why Dr. Sapphire made this episode [04:16] – The three types of business owners this episode serves [08:15] – Three questions to help you decide your summer plan [09:08] – Option 1: Setting your email summer hours [11:15] – Option 2: The takeoff countdown strategy [12:13] – Option 3: The email handover: handing it over completely [13:13] – Option 4: The email summer series: batch and disappear in peace [14:02] – How to write a series without stressing about content [17:53] – How to keep making sales while you are on holiday [18:36] – Which option is right for you and why it is your call Connect with Us Instagram: https://www.instagram.com/dr.sapphire_/ LinkedIn: https://www.linkedin.com/in/ayebanoabenwari/ Threads: https://www.threads.com/@dr.sapphire_ LinkedIn: https://www.linkedin.com/school/sapphirelearninghub/ Website: https://sapphirelearninghub.com/

See All (62)

About

Email Marketing Experiments was born out of a desire to share behind the scenes of failed and successful email marketing campaigns. What we’ve tried that worked and didn’t work. Instead of thinking it and testing it alone, we also share it. From welcome sequences to sales campaigns, list growth strategies, and more, we test ideas, break down results, and spill the tea. Come join us behind the scenes.

Information