Newsletter Coaching Session: Scaling Deep Dives Into a Newsletter Growth Engine
“$250k is when growth changes. It’s when you need systems. You usually can’t do it solo.” — Matt Gira, The QuarterMatt Gira joins Chenell & Dylan — in person — to share how he went from building underwater drones to launching The Quarter: a newsletter that deep dives into how founders grow bootstrapped businesses to $250K. This is an interview, but also an impromptu coaching session with Matt as we help him figure out how he can grow his newsletter faster and get it in front of the right audience.We talk content strategy, growth experiments, and the surprising data he's uncovering along the way.PS - Matt is not only an up-and-coming newsletter creator, he's also a member of the GIR Pro community 🔥→ Take your newsletter to the next level with GIR Pro >>KEY TAKEAWAYSWhy $250k is the key milestone for bootstrapped foundersHow Matt turned a niche data set into a powerful newsletter growth leverHow he grew his newsletter to 1,200+ subscribers without chasing viralityCollaborations, events, and the tour that could 10x his reachThe power of being early, scrappy, and generous in your creator journeyHow Matt reverse engineers founder journeys from YouTube to written contentThe role of YouTube, LinkedIn, and in-person meetups in his growth flywheelStrategies he’s testing now: content swaps, data licensing, servicesLINKS MENTIONEDThe Quarter (Matt's newsletter)The Bootstrapped ReportMatt on LinkedInKit's Craft + Commerce conferenceChenell's Deep Dive on CJ Gustafson of Mostly MetricsAsk us a question or submit a podcast topic idea: growthinreverse.com/questionsCheck out the 30 Days of Growth FREE >>30 Days of Growth Course Pre-launchGrowth In Reverse PRO CommunityWant your newsletter roasted? Submit it here. Check out past Growth In Reverse Deep Dives: https://growthinreverse.com/archive/FOLLOW ON SOCIALChenell: Twitter | LinkedIn | SubstackDylan: LinkedIn | BlueskyOUR NEWSLETTERSgrowthinreverse.comgrowthcurrency.netSubscribe & Leave a Review:If you found this episode valuable, take a second to rate and review us on Apple Podcasts or Spotify! It helps more newsletter creators find the show. Plus, if you submit a review, you’ll get priority for your own newsletter roast!Thanks to Tim Forkin for editing these episodes.
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Your Newsletter Is Too Easy to Join — Here’s Why That’s a Problem
“I love unsubscribes. Don’t be here if you don’t want to be here.”It is insanely easy to subscribe to a newsletter—and even MULTIPLE newsletters all at once.But is that a good thing? Should newsletter creators be more choosy when determining who signs up? We're diving into one of the most overlooked and under-discussed aspects of newsletter growth: friction. Specifically, how adding friction—rather than eliminating it—can actually improve subscriber quality, open rates, and monetization.This one’s a must-listen if you’re growing via referrals, recommendations, or paid ads—or if you’re cleaning your list and still not seeing better open rates.→ Take your newsletter to the next level with GIR Pro >>KEY TAKEAWAYSWhy the "low friction" mindset can lead to worse subscribersWhat happened when Chenell got aggressive about cleaning her listBackend vs. frontend friction: which is better and whenBuilding a false double opt-in to retain more good subscribersWhy double opt-in purgatory can kill 20–40% of your growthHow paid ads can inflate list size but tank your qualityForm fields, first names, and checkbox tactics that workThe danger of creating “unsubscribe friction” (and why you shouldn’t use it)What Dylan includes in every single broadcast to improve list healthCreative ideas like gated quizzes, segmenting checkboxes, and engagement-driven welcomesLINKS MENTIONEDWorkweekbeehiiv Creator NetworkKit Creator NetworkChris Hutchins → AllTheHacks.comAsk us a question or submit a podcast topic idea: growthinreverse.com/questionsCheck out the 30 Days of Growth FREE >>30 Days of Growth Course Pre-launchGrowth In Reverse PRO CommunityWant your newsletter roasted? Submit it here. Check out past Growth In Reverse Deep Dives: https://growthinreverse.com/archive/FOLLOW ON SOCIALChenell: Twitter | LinkedIn | SubstackDylan: LinkedIn | BlueskyOUR NEWSLETTERSgrowthinreverse.comgrowthcurrency.netSubscribe & Leave a Review:If you found this episode valuable, take a second to rate and review us on Apple Podcasts or Spotify! It helps more newsletter creators find the show. Plus, if you submit a review, you’ll get priority for your own newsletter roast!Thanks to Tim Forkin for editing these episodes.
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9 Big Takeaways For Creators From Craft + Commerce 2025
“The real value wasn’t in the keynotes—it was the dinners, the hikes, the casual connections.” – Dylan Redekop, first-time C+C attendeeDylan and Chenell reflect on their time at Kit's Craft + Commerce email newsletter conference for creators in Boise. But this episode isn’t just a recap — it’s a deep dive into what made the conference unforgettable: the people, the ideas, and the big shifts in how creators are building authentic businesses. From mastermind dinners with Pat Flynn to keynote takeaways on AI, content strategy, public speaking, and creator community, they unpack what creators should actually focus on in 2025.→ Take your newsletter to the next level with GIR Pro >>KEY TAKEAWAYSThe irreplaceable power of in-person connectionThe difference between “insanely valuable” vs “insanely frequent” contentWhy mastermind-style events create outsized ROIHow to use AI without burning outThe importance of crafting your personal “what do you do” introCreator identity and the fight with impostor syndromeContent strategy lessons from Sam Vander Wielen and Amanda GoetzPat Flynn’s “lean learning” growth loop from 0 to millions of YouTube subsHow to run better meetups and create serendipitous opportunitiesWhat Craft & Commerce nailed — and why you might want to go next yearLINKS MENTIONEDKit's Craft + Commerce creator conferencePat Flynn's Deep Pocket Monster YT ChannelSam Vander Wielen's websiteAmanda Goetz's websiteUltraspeaking (Tristan de Montebello & Michael Gendler)Ask us a question or submit a podcast topic idea: growthinreverse.com/questionsCheck out the 30 Days of Growth FREE >>30 Days of Growth Course Pre-launchGrowth In Reverse PRO CommunityWant your newsletter roasted? Submit it here. Check out past Growth In Reverse Deep Dives: https://growthinreverse.com/archive/FOLLOW ON SOCIALChenell: Twitter | LinkedIn | SubstackDylan: LinkedIn | BlueskyOUR NEWSLETTERSgrowthinreverse.comgrowthcurrency.netSubscribe & Leave a Review:If you found this episode valuable, take a second to rate and review us on Apple Podcasts or Spotify! It helps more newsletter creators find the show. Plus, if you submit a review, you’ll get priority for your own newsletter roast!Thanks to Tim Forkin for editing these episodes.
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From Tweets to 70k: How Jesse "Accidentally" Built a Newsletter of 70k Subscribers
"Every time I try to be an expert, I lose readers. When I’m just me, they stick around." – Jesse J. Anderson, Extra Focus newsletterFor the first time ever, Chenell & Dylan have recorded LIVE, in-person podcast episodes! Coming at you in-person from Kit Studios in Boise ID, Chenell & Dylan connect with Jesse J. Anderson—better known online as ADHD Jesse—to uncover the evolution of his successful newsletter, Extra Focus. Jesse's grown Extra Focus to over 70,000 subscribers and a combined social following in the hundreds of thousands. Jesse shares the real, raw, and often hilarious truth about building a brand and business around ADHD while balancing a full-time job and raising three kids.We talk through the early days of posting atomic essays in Ship 30 For 30, stumbling into virality, learning what content resonated (and what didn’t), and how he’s navigated massive growth across platforms like Substack, Instagram, and YouTube. Whether you're managing life with ADHD or not our chat with Jesse is full of valuable insight into newsletter growth, business, and some brutal honesty.→ Take your newsletter to the next level with GIR Pro >>KEY TAKEAWAYSJesse’s unexpected entry into content creation through Ship 30 for 30The signal pointing him towards doubling down on ADHD contentHow he built a massive newsletter while working full-time and raising a familyLessons learned from running paid newsletters, courses, and planning a thriving ADHD communityWhat led to his viral Instagram and Twitter growth, and Jesse's simple content repurposing strategyThe emotional rollercoaster of getting laid off and turning that moment into a creative breakthroughWhy authenticity matters now more than ever in a post-AI content worldLINKS MENTIONEDAsk us a question or submit a podcast topic idea: growthinreverse.com/questionsJesse’s Newsletter: ExtraFocus.comJesse on: Instagram | Twitter | BlueskyShip30For30.com (←affiliate link)Recorded in Kit Studios, Boise IDCheck out the 30 Days of Growth FREE >>30 Days of Growth Course Pre-launchGrowth In Reverse PRO CommunityWant your newsletter roasted? Submit it here. Check out past Growth In Reverse Deep Dives: https://growthinreverse.com/archive/FOLLOW ON SOCIALChenell: Twitter | LinkedIn | SubstackDylan: LinkedIn | BlueskyOUR NEWSLETTERSgrowthinreverse.comgrowthcurrency.netSubscribe & Leave a Review:If you found this episode valuable, take a second to rate and review us on Apple Podcasts or Spotify! It helps more newsletter creators find the show. Plus, if you submit a review, you’ll get priority for your own newsletter roast!Thanks to Tim Forkin for editing these episodes.
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Should your newsletter have a podcast? (Our take after 6 months of episodes)
"Podcasting isn’t a shortcut to growth—but it’s a hell of a way to deepen relationships." – Chenell BasilioWhat can happen when you commit to a weekly podcast for six straight months? You're about to find out. Chenell & Dylan pull back the curtain on the Growth In Reverse podcast—sharing the behind-the-scenes of what’s worked, what hasn’t, and what we’ve learned along the way.We get real about the numbers: subscribers, downloads, YouTube stats, and more. Plus, we chat through the very real question—should newsletter writers even start a podcast? You’ll hear our honest take on the ROI (or lack thereof), and the surprising benefits that go beyond metrics.→ Take your newsletter to the next level with GIR Pro >>KEY TAKEAWAYSReflecting on 6 months of consistent podcasting and what kept us goingWhy podcasting isn’t a fast-track to newsletter growth—and what it is great forThe powerful trust-building impact of being in your audience’s earsOur top-performing content and what formats resonated mostHow YouTube fits into our podcast strategy and where Shorts fell flatLessons from other creators like Jay Clouse, Lenny Rachitsky, and Aakash GuptaEasy ways for newsletter creators to test podcasting without going "all in"LINKS MENTIONEDAsk us a question or submit a topic idea: growthinreverse.com/questionsThe Pour Over podcast (on Spotify)Riverside.fmMatt Giovanisci (MoneyLab)Jay Clouse's YT ChannelLenny Reaches 1M Subscribers (past GIR episode)Lenny Podcast (YT Channel) Check out the 30 Days of Growth FREE >>30 Days of Growth Course Pre-launchGrowth In Reverse PRO CommunityWant your newsletter roasted? Submit it here. Check out past Growth In Reverse Deep Dives: https://growthinreverse.com/archive/FOLLOW ON SOCIALChenell: Twitter | LinkedIn | SubstackDylan: LinkedIn | BlueskyOUR NEWSLETTERSgrowthinreverse.comgrowthcurrency.netSubscribe & Leave a Review:If you found this episode valuable, take a second to rate and review us on Apple Podcasts or Spotify! It helps more newsletter creators find the show. Plus, if you submit a review, you’ll get priority for your own newsletter roast!Thanks to Tim Forkin for editing these episodes.
About Growth In Reverse (Newsletter Growth & Email Marketing)
Growth In Reverse is the must-listen podcast for anyone serious about growing an email list and turning a newsletter into a thriving business. Hosted by Chenell Basilio and Dylan Redekop, two leading voices in the newsletter space, this show pulls back the curtain on how today’s top newsletter operators actually grow and make money.
Episodes include deep-dive teardowns of the strategies behind the most successful newsletters. You’ll hear how creators like Justin Welsh, Codie Sanchez, Sahil Bloom, and other creator founders are building loyal audiences and turning subscribers into revenue. Learn how they attract traffic, increase conversions, boost retention, and scale without burning out.
Whether you're launching your first newsletter or refining your growth engine, Growth In Reverse gives you proven tactics you can use right away. From onboarding systems and referral programs to sponsorships and paid products, this podcast helps you grow faster and smarter. If you’re ready to stop guessing and start applying what works, tune in and learn how the best are building newsletters that last.
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