Inside a Top 10 Spotify Podcast Business, Local Newsletters To Agency Funnel, Will AI Change Email Marketing Forever?

Ryan Deiss (DigitalMarketer, Scalable.co) joins Matt to talk about why he killed an eight-figure course business, the 80% sales drop that forced the pivot, why AI is replacing courses faster than anyone wants to admit, and how to actually monetize expertise in a post-course world.Timestamps: 00:00 Intro 00:28 Why Ryan "Retired" From DigitalMarketer 03:32 The Real Reason Course Sales Collapsed 06:37 Why AI Beats Courses Every Time 11:54 DigitalMarketer's 80% Revenue Drop 13:05 Why "Course Business" Is the Wrong Frame 16:53 Build Your Own Media First 21:19 The 4 Ways Media Companies Make Money 22:23 Sell AI Trained on Your IP, Not the Course 28:23 Why Coaching On Top of Courses Won't Save You 33:12 The Truth About Cohort-Based Programs 35:14 The 3 Event Business Models 41:36 Sponsorships, Exhibitors & Critical Mass 48:07 Sponsorship Tiers and Protecting the Stage 58:00 Activations, Meetups & Sponsored Experiences 1:02:28 Where to Find Ryan📌 Resources: The Scalable Company DigitalMarketer 🔗 Connect with Ryan Deiss: LinkedInNewsletter

Brian Morrissey (The Rebooting) joins Matt and Kolby to talk about his three-archetype theory of modern media, why most TBPN streaming-show clones will fail, the real strategic value of SMS, and why aging out of LinkedIn is a bigger flex than flying private.Timestamps: 00:00 Intro 00:06 The 3 Media Archetypes: Artists, Suits, Engineers 05:54 Streaming Media and MTS vs TBPN 08:00 Why Webinars Punch Above Their Weight 12:37 The Power of Parasocial Podcast Connections 16:09 Is Streaming A Fad? Neo-Traditional Media 20:18 The Underpants Gnome Problem With Clips 24:03 Is SMS The New Email? 26:45 The Hardest Part Is Having The Audience 29:51 Brian's Writing Process (No Audience In Mind) 34:36 Smart SMS Use Cases (Events, Subtext) 40:00 Building A Strategic Reserve Of Phone Numbers 42:59 Why SMS Crushes For Webinar Registrations 49:47 NoScroll And Anonymous X Accounts 53:22 Aging Out Of LinkedIn Is The Real Flex 54:05 Where To Find Brian📌 Resources Mentioned: The RebootingPeople vs Algorithms (podcast) Monitoring The Situation (MTS) Breaking Points 🔗 Connect with Brian Morrissey: LinkedIn Website & Newsletter Enjoying the show? Leave a 5-star review on Apple or Spotify, then email [email protected] or [email protected] with a screenshot and a question — we'll answer it on the show.

In today's episode, Ethan Brooks (Austin Business Review), Alyssa Dulin (Kit), and Jonathan Barshop (Modern Wisdom) join Matt and Kolby to discuss how to monetize a local newsletter with services instead of ads, what AI is actually doing to email deliverability, and the unconventional growth tactics that move a podcast in 2026. Timestamps: 00:00 Intro 03:00 Ethan Brooks on Austin Business Review and Local Media 07:30 Why Local Newsletters Are Best Monetized as Services (Not Ads) 10:40 Selling Austin: $300K From Under 1,000 Readers 13:00 The $25K-in-8-Weeks Concrete Leads Side Business 22:00 Ethan's Two Frameworks: Valuable Audience + Media Monetization 32:00 Alyssa Dulin on AI in the Inbox 35:00 The New Curator in Town — How AI Is Rewriting Deliverability 46:00 The One-Word Reply Tip That Beats Every Other Engagement Tactic 52:00 Google Postmaster Tools: The Most Overlooked Deliverability Tool 1:01:00 Jonathan Barshop on Building a Podcast That Actually Grows in 2026 1:11:00 Why Premise Beats Production 1:18:00 The Cross-Promo That Supercharged My First Million 1:25:00 Engineering "Viral" Moments — The Tim Ferriss + Edward Norton Trick 1:42:00 Modern Wisdom's Tour Model and 12-Partner Sponsorship Strategy 📌 Resources Mentioned: Austin Business ReviewGoogle Postmaster Tools Modern Wisdom🔗 Connect with Ethan Brooks:  LinkedIn Newsletter🔗 Connect with Alyssa Dulin: LinkedIn 🔗 Connect with Jonathan Barshop: LinkedIn

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In today's episode, Neville Medhora (Swipefile, Copywriting Course, ex-AppSumo) joins Matt and Kolby to talk about how good copy delivered AppSumo's first $10,000 day, why his flagship Copywriting Course business is being eaten by AI while Swipefile.com is soaring, Neville's content workflow, and why selling software is dead in 2026.Timestamps:01:19 House of Rave and Dropshipping in High School03:21 Finding Copywriting and AppSumo's First $10K Day05:53 Copywriting Course Dying, Swipefile Soaring11:27 Brand, Style, and Standing Out From AI16:33 How Swipefile's Business Model Works18:44 Why Selling Software Is Dead22:51 The Hybrid Sponsorship Model That Actually Pays26:45 Custom Content and Evergreen Sponsorship Deals33:47 Acquired's $4.8M Pre-Rolls and B2B Ad Math35:57 Why Blogging Is Social Media Now37:15 Neville's Content Flow: Swipefile → Newsletter → Social40:43 Growing a Newsletter in 202645:00 Why Neville Won't Sell Claude Skills (Yet)52:34 Where To Find Neville📌 Resources Mentioned:The Gary Halbert Letters — https://www.thegaryhalbertletter.comWait But Why (Tim Urban) — https://waitbutwhy.com🔗 Connect with Neville Medhora:LinkedIn — https://www.linkedin.com/in/neville-medhora-654749/Swipefile — https://swipefile.comYouTube — https://www.youtube.com/channel/UCSN1tlH1nvAXkv9nnBCmfiQ🍿 Watch on YouTubehttps://www.youtube.com/@growletter

Walker Deibel (Buy Then Build) joins Matt and Kolby to talk about how he wrote a category-defining book, built a newsletter to 300,000 subscribers, and used that list to raise $4 million in four hours. They cover his grassroots book launch strategy, why he believes newsletters are the most impactful asset any entrepreneur can build, and his framework for navigating private capital markets as what he calls the "new family office."Want to get your first 1,000 newsletter subscribers in 30 days? Go here 👉 https://www.newsletteroperator.com/subscribeApply To Work With My Agency 👉 https://www.growletter.comTimestamps:00:00 Intro03:53 The Shift from Startups to Acquisitions05:36 How Buy Then Build Changed Entrepreneurship08:33 Grassroots Marketing and Book Launch Strategy12:18 Creating a Movement and Defining a New Category16:15 Frameworks for Exceptional Content19:14 Writing the Book and Defining Entrepreneurship22:29 Monetizing the Book and Building Community29:14 Why In-Person Events Still Matter35:43 Transitioning from Acquisition Lab to New Ventures36:59 The Power of Email Lists in Investing39:33 Building a Private Market Investing Community43:15 Creating Value Through Direct Investments46:35 The Economics of Being a Family Office48:04 Newsletters as the Most Impactful Business Asset48:59 Where to Find Walker📌 Resources Mentioned: Buy Then Build (book)Acquisition LabGood to Great by Jim Collins🔗 Connect with Walker Deibel: LinkedIn — https://www.linkedin.com/in/walkerdeibel/ Website — https://walkerdeibel.com Newsletter — https://wealthstack1.com/

Matt and Kolby break down OpenAI's acquisition of TBPN for over $100 million and what it actually means for media. They dig into why the deal was less about audience size and more about an aqua hire of founders John Coogan and Jordi Hayes, how tech companies consistently use media as a PR and storytelling asset, and what lessons indie creators can take from TBPN's 18-month run to a nine-figure exit.Want to get your first 1,000 newsletter subscribers in 30 days? Go here 👉 https://www.newsletteroperator.com/subscribeApply To Work With My Agency 👉 https://www.growletter.comTimestamps:00:00 Intro05:29 Why the Founders Were the Real Asset11:03 Editorial Independence Concerns16:29 The Future of Infotainment in B2B22:54 Media as a Tech Acquisition Strategy28:43 Focus on Your Core Thing📌 Resources Mentioned:TBPN (Tech Business Programming Network) 🍿 Watch on YouTubehttps://www.youtube.com/@growletter

Taylor Cromwell (Creator Diaries) joins Kolby to talk about what it actually takes to go from creator to founder — and what makes a media business acquisition-ready. They break down the Starter Story and Salary Transparent Street deals, how to eliminate key-face risk, why IRL events are the next big creator play, and the surprising business Taylor's mom accidentally built in Italy.Want to get your first 1,000 newsletter subscribers in 30 days? Go here 👉 https://www.newsletteroperator.com/subscribeApply To Work With My Agency 👉 https://www.growletter.comTimestamps:00:00 Intro01:00 Creator Diaries and the Creator-to-Founder Gap03:44 The Starter Story Acquisition — What Creators Can Learn05:23 Are Big Companies Still Buying Creator Brands?07:32 How to Make Your Creator Business Acquisition-Ready09:45 Key Face Risk — How to Build a Brand Beyond Yourself13:27 IRL Events and Why Every Creator Should Think About Them18:21 The Business Models Behind Creator Events24:12 Scaling Pains — What Creators Avoid (But Shouldn't)31:47 Taylor's Mom Accidentally Built a Business in Italy37:21 Where to Find Taylor📌 Resources Mentioned: Starter Story, Salary Transparent Street, StoryArb🔗 Connect with Taylor: LinkedIn Creator Diaries

In today's episode, Matt and Kolby dig into what's actually working in audience building right now — fandom vs. impressions, the channels that actually build real community, and why frameworks are the ultimate cheat code for creator brands. Chenell Basilio (Growth in Reverse) joins to talk pop-up newsletters, cross-promotion strategy, and what's next after email. Plus, the guys debate whether Mr. Beast is the next BuzzFeed and what the rise of AI slop means for creators who actually give a damn about their craft.Want to get your first 1,000 newsletter subscribers in 30 days? Click here: https://www.newsletteroperator.com/subscribeWatch on YouTubeTimestamps:00:00 Stardew Valley and the Indie Creator Model 05:31 Fandom vs. Impressions: What Actually Builds an Audience10:52 Cross-Promotion Strategy with Chenell Basilio16:09 Pop-Up Newsletters and Re-engaging Churned Subscribers30:01 Why Every Creator Needs a Framework41:17 What's Next: SMS, Live Events, and YouTube46:55 The Case for Live Streaming in B2B Media01:02:05 Is Mr. Beast the Next BuzzFeed?01:12:15 Betting on Emerging Creators01:17:32 The Culturalist and the Future of Thoughtful Content🔗 Connect with Chenell: https://growthinreverse.com/ Chenell's Podcast30 Days of Growth🐝 Looking for the best newsletter and email marketing platform? Beehiiv is what I use and recommend: Click here to get a discount through my referral link: https://www.beehiiv.com/?via=matt-mcgarry

Register here: https://workshop.growletter.com/I’m hosting a free live workshop THIS Thursday on… The New Media Model: How To Build A Media Business AI Can't KillYour business model is under attack by AI and market saturation. The old ways to make money from content don’t work anymore.This will show you how to fix it in 60 minutes. Plus, break down the “New Media Model” your business can use to get stronger as AI rises (not get replaced by it).Join us for free: https://workshop.growletter.com/