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by Matt McGarry and Ryan Carr
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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 ...
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 Connec...
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 (...
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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 S...
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?...
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.newslett...
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/sub...
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