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 School
• 03:21 Finding Copywriting and AppSumo's First $10K Day
• 05:53 Copywriting Course Dying, Swipefile Soaring
• 11:27 Brand, Style, and Standing Out From AI
• 16:33 How Swipefile's Business Model Works
• 18:44 Why Selling Software Is Dead
• 22:51 The Hybrid Sponsorship Model That Actually Pays
• 26:45 Custom Content and Evergreen Sponsorship Deals
• 33:47 Acquired's $4.8M Pre-Rolls and B2B Ad Math
• 35:57 Why Blogging Is Social Media Now
• 37:15 Neville's Content Flow: Swipefile → Newsletter → Social
• 40:43 Growing a Newsletter in 2026
• 45:00 Why Neville Won't Sell Claude Skills (Yet)
• 52:34 Where To Find Neville

📌 Resources Mentioned:
The Gary Halbert Letters — https://www.thegaryhalbertletter.com
Wait But Why (Tim Urban) — https://waitbutwhy.com

🔗 Connect with Neville Medhora:
LinkedIn — https://www.linkedin.com/in/neville-medhora-654749/
Swipefile — https://swipefile.com
YouTube — https://www.youtube.com/channel/UCSN1tlH1nvAXkv9nnBCmfiQ

🍿 Watch on YouTube

https://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/subscribe

Apply To Work With My Agency 👉 https://www.growletter.com

Timestamps:
00:00 Intro
03:53 The Shift from Startups to Acquisitions
05:36 How Buy Then Build Changed Entrepreneurship
08:33 Grassroots Marketing and Book Launch Strategy
12:18 Creating a Movement and Defining a New Category
16:15 Frameworks for Exceptional Content
19:14 Writing the Book and Defining Entrepreneurship
22:29 Monetizing the Book and Building Community
29:14 Why In-Person Events Still Matter
35:43 Transitioning from Acquisition Lab to New Ventures
36:59 The Power of Email Lists in Investing
39:33 Building a Private Market Investing Community
43:15 Creating Value Through Direct Investments
46:35 The Economics of Being a Family Office
48:04 Newsletters as the Most Impactful Business Asset
48:59 Where to Find Walker

📌 Resources Mentioned:

Buy Then Build (book)

Acquisition Lab

Good 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/subscribe

Apply To Work With My Agency 👉 https://www.growletter.com

Timestamps:

00:00 Intro

05:29 Why the Founders Were the Real Asset

11:03 Editorial Independence Concerns

16:29 The Future of Infotainment in B2B

22:54 Media as a Tech Acquisition Strategy

28:43 Focus on Your Core Thing

📌 Resources Mentioned:

TBPN (Tech Business Programming Network)

🍿 Watch on YouTube

https://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/subscribe

Apply To Work With My Agency 👉 https://www.growletter.com

Timestamps:

00:00 Intro

01:00 Creator Diaries and the Creator-to-Founder Gap

03:44 The Starter Story Acquisition — What Creators Can Learn

05:23 Are Big Companies Still Buying Creator Brands?

07:32 How to Make Your Creator Business Acquisition-Ready

09:45 Key Face Risk — How to Build a Brand Beyond Yourself

13:27 IRL Events and Why Every Creator Should Think About Them

18:21 The Business Models Behind Creator Events

24:12 Scaling Pains — What Creators Avoid (But Shouldn't)

31:47 Taylor's Mom Accidentally Built a Business in Italy

37:21 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/subscribe

Watch on YouTube

Timestamps:

00:00 Stardew Valley and the Indie Creator Model

05:31 Fandom vs. Impressions: What Actually Builds an Audience

10:52 Cross-Promotion Strategy with Chenell Basilio

16:09 Pop-Up Newsletters and Re-engaging Churned Subscribers

30:01 Why Every Creator Needs a Framework

41:17 What's Next: SMS, Live Events, and YouTube

46:55 The Case for Live Streaming in B2B Media

01:02:05 Is Mr. Beast the Next BuzzFeed?

01:12:15 Betting on Emerging Creators

01:17:32 The Culturalist and the Future of Thoughtful Content

🔗 Connect with Chenell:

https://growthinreverse.com/

Chenell's Podcast

30 Days of Growth

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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 Summit

02:12 Why Build a Trade Show

05:15 Trade Shows vs. Conferences

07:03 Ticket Pricing, Booth Costs & Revenue Model

09:39 Balancing Attendee Tickets With Exhibitor Value

11:29 Vendor Tickets

13:13 The Role of Media & Content in Growing the Event

17:41 How Brent Sells Tickets

19:26 Post-Purchase Surveys

21:27 HVAC Influencers

24:28 Should Influencers Attend the Event to Drive Tickets?

26:34 Promo Codes, Measurability & Implied Endorsement

28:35 Audience-Event Fit

30:29 Getting Your First Sponsors & Exhibitors

32:35 Proving ROI to Sponsors

35:02 What Other Trade Show Opportunities Exist Right Now

37:35 Hosted Buyer Programs & The Hidden Revenue Model

38:16 How Big Can the Heat Pump Summit Get?

41:24 Exit Strategies & Building an Event Conglomerate

43:52 Private Equity in the Trades & the Blue Parachute Idea

44:10 Mike Rowe & the Role of Celebrity at Trade Events

47:23 Final Advice

🔗 Connect with Brent Davidson:

LinkedIn
US Heat Pump Summit

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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 Ragland
03:42 Why Every Creator Needs a Framework
07:19 The Gap & Wrap System Explained
10:34 What Makes a Framework Actually Work
13:48 How Frameworks Drive Content & Growth
16:36 Types of Frameworks (Acronyms, Visuals, Mental Models)
20:05 The Real Shift: From Creator to Operator
25:55 Why Growth Plateaus (And What Changes Next)
31:28 The Truth About YouTube Growth Today
36:41 The Substack Trap (And Why Most People Get It Wrong)

🔗 Connect with Matt Ragland:

• MattRagland.com
• Matt'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 Topics
01:04 Breaking Points: A Case Study in New Media Success
13:39 Starter Story's Acquisition by HubSpot
24:15 Lenny's Newsletter: A B2B Creator's Journey
33:30 Colin and Samir's LA Creator Summit
35:03 The Importance of Marketing for Creators
37:14 How To Make A Great Event
43:17 Monetization Strategies for Events
49:58 The Rise of AI-Generated Content
57:02 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.