New Media

Jonathan Hunt (VP of HubSpot Media) joins Matt and Kolby to talk about how HubSpot built a 50M-reach owned-media network, the four-part test they run on every acquisition (Hustle, Mindstream, Starter Story, Futurepedia), and why they killed every audio-only podcast on the network.

Timestamps: 

• 00:00 Intro
•  03:33 Why HubSpot Buys Media Companies
•  04:45 What HubSpot Media Actually Is (65 People, 3 Pillars)
•  07:15 The Editorial Thesis Behind Every Acquisition
•  12:26 The HubSpot Acquisition Test: 4 Criteria
•  14:53 Inside HubSpot's 150-Creator Program
•  22:24 Co-Creating Brands With Creators
•  25:06 Why HubSpot Went YouTube First
•  30:41 The Ad Fatigue Problem (And How They Solved It)
•  33:01 Scott Galloway and the Native Lead Magnet Play
•  36:15 How HubSpot Reinvests Profits Into Growth
•  39:46 Minority Report-Level Attribution
•  42:00 Why HubSpot Killed Audio-Only Podcasts
•  43:12 Reactions: Puck, TBPN, Sherwood, A16Z
•  51:31 Why HubSpot Won't Launch a Net-New Live Show
•  53:47 Where to Find Jonathan

📌 Resources: 

•  Mindstream
•  Starter Story
•  Futurepedia
•  HubSpot Creator Program

🔗 Connect with Jonathan: 

• LinkedIn

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Katelyn Bourgoin (founder of Unignorable) joins Matt and Kolby to break down the 6 types of ownable ideas, the 5-question framework she uses to engineer one, why courses are losing value to AI-enabled "brainware" agencies, and a live audit of Matt's ownable idea.

Timestamps: 

• 00:00 Intro 
• 00:39 The Why We Buy → Unignorable Rebrand 
• 04:16 Ownable Ideas: Test Round (Sinek, Welsh, Sanchez) 
• 09:30 What an Ownable Idea Actually Is 
• 12:22 The 6 Types of Ownable Ideas 
• 16:26 How to Create Your Own (and Why It's Hard) 
• 18:55 The 5-Question Framework 22:10 Brené Brown Broken Down by the Framework 
• 24:16 Lightning vs. Engineered Ideas 
• 27:06 Live Audit: Matt's Overlap Effect Framework 
• 39:58 Brainware: The AI-Enabled Agency Thesis 
• 43:32 Productized Services as the New Course 
• 50:37 Accountability as a Service 
• 52:36 Sunsetting What No Longer Fits 
• 54:38 Where to Find Katelyn

📌 Resources Mentioned: 

• UNIGNORABLE
• Why We Buy newsletter
• Brian Balfour's Four Fits Framework 

🔗 Connect with Katelyn Bourgoin: 

• LinkedIn  
• Website & Newsletter

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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 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 3
• 3:12 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:

• LinkedIn
• Newsletter

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 Rebooting
People 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 Review
• Google Postmaster Tools 
• Modern Wisdom

🔗 Connect with Ethan Brooks:  

• LinkedIn 
• Newsletter

🔗 Connect with Alyssa Dulin: 

• LinkedIn 

🔗 Connect with Jonathan Barshop: 

• LinkedIn

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Enrollment ENDS May 4th at 11:59 pm EST. 

This is the last opportunity to join Write, Grow, Sell for the next 5+ months and get in at the lowest price since 2024.

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