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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/

Brent Davidson built a 500-person trade show for HVAC contractors from scratch — and in this episode, he breaks down the business model behind it: how exhibitors and sponsors pay the bills, how to design attendee flow, and why in-person marketplaces are more durable than anything algorithm-dependent. Matt and Kolby dig into the operational side of running a trade show — from booth pricing and venue logistics to speaker strategy and influencer relationships. If you're thinking about events as a media business model, this is the blueprint.Timestamps:00:00 Introduction & What Is the US Heat Pump Summit02:12 Why Build a Trade Show 05:15 Trade Shows vs. Conferences07:03 Ticket Pricing, Booth Costs & Revenue Model09:39 Balancing Attendee Tickets With Exhibitor Value11:29 Vendor Tickets13:13 The Role of Media & Content in Growing the Event17:41 How Brent Sells Tickets19:26 Post-Purchase Surveys 21:27 HVAC Influencers 24:28 Should Influencers Attend the Event to Drive Tickets?26:34 Promo Codes, Measurability & Implied Endorsement28:35 Audience-Event Fit30:29 Getting Your First Sponsors & Exhibitors32:35 Proving ROI to Sponsors 35:02 What Other Trade Show Opportunities Exist Right Now37:35 Hosted Buyer Programs & The Hidden Revenue Model38:16 How Big Can the Heat Pump Summit Get?41:24 Exit Strategies & Building an Event Conglomerate43:52 Private Equity in the Trades & the Blue Parachute Idea44:10 Mike Rowe & the Role of Celebrity at Trade Events47:23 Final Advice🔗 Connect with Brent Davidson:LinkedInUS Heat Pump Summit🐝 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.

In today’s episode, we sit down with Matt Ragland to break down how top creators actually build leverage, grow audiences, and scale sustainable media businesses. We dive into frameworks that make you memorable, the reality of plateauing on YouTube, and how to evolve from solo creator to true operator. Matt also shares lessons from working behind the scenes with some of the biggest names in newsletters and creator education.Timestamps:00:00 Introduction to Matt Ragland03:42 Why Every Creator Needs a Framework07:19 The Gap & Wrap System Explained10:34 What Makes a Framework Actually Work13:48 How Frameworks Drive Content & Growth16:36 Types of Frameworks (Acronyms, Visuals, Mental Models)20:05 The Real Shift: From Creator to Operator25:55 Why Growth Plateaus (And What Changes Next)31:28 The Truth About YouTube Growth Today36:41 The Substack Trap (And Why Most People Get It Wrong)🔗 Connect with Matt Ragland:MattRagland.comMatt's YouTube Channel🐝 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.

In today’s episode we break down four media companies including Breaking Points, Starter Story, Lenny's Newsletter, and Colin and Samir's creator summit, pulling out what's working, what's being left on the table, and what every media founder should take notes on. Plus, we get into the AI slop debate and what it actually means for creators trying to build something real.Timestamps:00:00 Overview of Topics01:04 Breaking Points: A Case Study in New Media Success13:39 Starter Story's Acquisition by HubSpot24:15 Lenny's Newsletter: A B2B Creator's Journey33:30 Colin and Samir's LA Creator Summit35:03 The Importance of Marketing for Creators37:14 How To Make A Great Event43:17 Monetization Strategies for Events49:58 The Rise of AI-Generated Content57:02 Navigating the Future of AI in Media🔗 Resources Mentioned:Breaking Points Starter Story Lenny's Newsletter Colin and Samir's LA Creator Summit🐝 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.