Newsletter Operator

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

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

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

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

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

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)

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

Welcome to the first episode of the New Media Podcast with Matt McGarry and Kolby Hatch. In this episode, we break down the business of media—from newsletters and YouTube to events and monetization strategies. We also dive into lessons from New Media Summit, building profitable media companies, and what's actually working right now. If you're building in the creator economy, this is the behind-the-scenes conversation you don't usually hear.

In this episode, I share an important update about the future of the podcast as we relaunch with a new name and direction. While the show started focused on newsletters and email marketing, the new version will expand into helping you build an independent media, education, or creator business. We'll be covering audience growth, newsletters, monetization, and the strategies behind modern media companies. Subscribe to the video version of the podcast and our YouTube channel here. 

Get the slides and resources mentioned from this episode linked here. In this video, I break down the 5 frameworks that helped my clients generate over $100 million in sales from email. These are the exact strategies top media, education, and creator businesses use to grow their email list, boost open rates and click-through rates, and drive more sales. Timestamps:00:00: Introduction01:16: Framework #1: The MAGIC Formula (turn social followers into email subscribers)15:22: Framework #2: First-Party Data & SMS19:11: Framework #3: The WE-PAC Welcome Email25:56: Framework #4: The Deliverability Detox30:37: Framework #5: The Newsletter FlywheelOther Resources:

Learn more about Uscreen https://www.uscreen.tv/In this episode, I sit down with Allison Yazdian, CEO of Uscreen, to break down how creators can build scalable, recurring revenue with video-first memberships. We cover what makes a compelling offer, how to price and tier it, and the features that drive engagement and retention. Allison shares real examples of creators generating millions through subscriptions, live streams, and community. If you want to own your audience and turn content into predictable monthly revenue, this is a must-watch.Connect with Allison on LinkedIn: https://www.linkedin.com/in/allisonyazdian/Timestamps:00:00: Meet Allison Yazdian (CEO of Uscreen)01:20: What Uscreen Does04:00: How Creators Make Money with Memberships06:00: Big Creators Using Uscreen 09:00: Why Memberships Beat Ads & One-Off Products12:00: What Makes a Great Membership Offer16:00: Free Tiers, Trials & Entry Offers18:00: Pricing Strategy & Benchmarks22:00: Structuring Your Membership Tiers24:30: Must-Have Features (Community, Live, Challenges)27:30: How to Market & Sell Your Membership31:30: Onboarding New Members the Right Way33:30: Reducing Churn & Increasing Retention36:00: One Thing That Improves Retention Fast38:00: Who Uscreen Is Best For + How to Get StartedOther Resources:

Learn more about Ezoic: https://www.ezoic.com/I sit down with Gavin Bechtold (Ezoic) to reveal how publishers, creators, and newsletter operators are leaving serious money on the table by ignoring website monetization. We break down programmatic ads, first-party data, and how sending traffic back to your site can dramatically increase subscriber lifetime value. If you run a newsletter or media business, this episode will change how you think about traffic and revenue.Connect with Gavin directly: https://www.linkedin.com/in/gavinbechtold/Timestamps:00:00: Intro & why website traffic is overlooked05:47: Website vs. newsletter monetization12:50: What RPMs can you actually expect?16:46: Myth busting: Do ads hurt user experience?29:21: How first-party data increases ad revenue36:56: Who Ezoic is a good fit forMore Resources:

Traditional online courses are dead. People don't need more information. They need execution. In this video, I break down why live cohort-based programs are the fastest way to turn your expertise into a $100K+ offer and eventually a $1M/year business. You'll learn how to craft your cohort in 8 simple steps, even if you have no audience, testimonials, or teaching experience. Get the full guide and next steps here.Timestamps:01:35 Introduction 3:00 Why courses are dead5:25 The execution problem5:48 Why cohorts win7:22 Step 1: Pick the outcome10:45 Step 2: Structure it14:22 Step 3: Homework plan15:06 Step 4: Build the system16:11 Step 5: Gamify + track19:40 Step 6: Track results20:43 Step 7: Scarcity21:22 Step 8: Social proof26:58 Step 9: Cohort outline30:15 Step 10: Build anticipation31:17 Step 11: Always sell, then build31:55 Step 12: Marketing scheduleWant to learn what's working in media right now? New Media Summit brings together 500+ founders in Austin Feb 26-27 with Codie Sanchez, Ryan Deiss, Matt Paulson, and more. Get tickets here!

What's changing in newsletters, email marketing, and the creator economy — and how do you grow, monetize, and scale in 2026?In this FREE online event, 8 industry experts share 15+ data-backed predictions on newsletter growth, email deliverability, audience development, and media monetization — plus actionable strategies you can apply immediately.

This episode is a complete 15-part breakdown of how to sell your first digital product from scratch. I walk through how to choose the right product, validate demand, and price it for maximum conversions. You'll learn why you don't need a huge audience to make real money. I also cover launch strategy, promotion timelines, and common mistakes that kill first launches. If you're a creator, founder, or newsletter writer aiming for your first $1k–$10k launch, this is for you.Watch the full episode on YouTube linked here.Watch my monetization masterclass here.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Timestamps:00:00 Introduction to Selling Digital Products01:09 Building an Email List for Success03:48 Understanding Your Audience's Needs06:08 Types of Media Products06:50 Pricing Your Product 08:15 Your Tech Setup10:26 Overcoming the Need for Testimonials11:31 Navigating Sales Without Being Salesy12:25 Mastering Copywriting13:56 Promoting Your Product Effectively15:29 Establishing Credibility as a Seller16:48 Your First Launch18:26 Refunds and Customer Concerns19:14 Creating a Minimum Viable Product20:04 Validating Your Product Idea20:53 Running a Pre-Sale for Your Product

In this video, I break down why so many people hesitate to start a newsletter— and why that fear once held me back too. You'll learn the biggest advantages of launching one, from owning your audience to building a scalable, high-profit media business with multiple revenue streams. I also share my full journey, including early failures, the lessons that changed everything, and how my newsletter eventually grew to 50,000+ subscribers and a multimillion-dollar business. By the end, you'll understand not only why a newsletter can transform your income, but also how it accelerates your skills, opportunities, and long-term growth—no matter your starting point.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Timestamps:00:00 Overcoming the Fear of Starting a Newsletter00:55 The Value of Owning Your Audience04:03 Low Startup Costs + Big Income Potential07:31 Scalability and Major Business Potential09:18 Multiple Revenue Streams You Can Build12:02 Building Skills Through Publishing15:07 The Right Motivation for Starting a Newsletter18:45 Personal Journey, Failures & Lessons Learned22:05 Taking Action: Launching Your Newsletter

In this Q&A, we discuss the future of media and why newsletters, YouTube, and podcasts will dominate. Matt shares his MAGIC Framework for converting social followers into email subscribers. We discuss Beehiiv's newest features, including dynamic content, native analytics, and its ad network. The Q&A also covers paywalls, reader behavior shifts, and the biggest newsletter design mistakes. Finally, Matt explains how to know when you've hit content–market fit and when to use paid acquisition.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Timestamps & Questions:00:00 Introduction00:48 What do you think the future of media will look like?04:39 How do you drive traffic from a discovery platform to your newsletter?11:01 How do you recommend utilizing paywalls and gated content?13:29 What's the best new Beehiiv feature for smaller creators?16:05 How do you know a discovery platform is working?16:53 How should you utilize dynamic content?19:08 Should Beehiiv integrate better with Shopify?20:00 Does this put pressure on Kit and Substack to evolve?22:03 What's the most underrated moat a newsletter can have?23:12 How will reader behavior change overtime?25:01 How will B2B newsletter evolve?26:38 Advice for someone sitting on an idea for 6 months?28:32 How do you know when you have audience market fit?30:04 When should you run paid ads?31:53 What are the biggest design mistakes you see?

In this episode, we break down how to build a profitable, future-proof content business. You'll learn why email subscribers are far more valuable than social followers, how to balance content frequency and quality, and how AI is reshaping media and audience engagement. We also cover how to identify real problems that lead to valuable products and how to test newsletter ideas to find your perfect niche.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Timestamps:00:00 Introduction00:30 How do you know if a Newsletter idea is worth pursuing? 2:15 What's more valuable: 10,000 email subscribers or 100k Instagram followers? 3:15 What are you thoughts on buying active email lists?4:57 How do you think about frequency vs quality?6:00 How to avoid last minute changes from sponsors? 8:25 What shift in the media industry are founders not ready for?11:43 How do you think about community building?14:01 How can you sell digital products to moms? 16:38 If you could only monetize your audience in one way, what would you choose?18:33 What's a contrarian opinion you have on the newsletter industry?19:10 How to launch a newsletter based newsletter while living abroad?20:26 How to approach content when competitors copy you?21:44 How do you think about standing out in a crowded market?

In this video, I break down 30 different newsletter growth channels—from social and search to partnerships and paid ads—and rank them based on scale, effort, and subscriber quality. I'll share surprising data showing just how wildly subscriber value can vary between sources, plus the framework I use to evaluate conversion and lifetime value. We'll cover channels like YouTube, LinkedIn, Instagram, SEO, Meta ads, cross-promotions, and more. If you're trying to figure out which few channels to focus on for real, sustainable growth, this video will point you in the right direction.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Timestamps:00:00 Overview of the Newsletter Growth Tier List01:33 How I'm Ranking 30+ Newsletter Growth Channels02:11 Organic Social: YouTube, LinkedIn, Instagram, Substack Notes, X, TikTok10:42 Paid Social: Meta, LinkedIn, X, and TikTok Ads14:41 Search & SEO: Organic vs. Google Ads18:05 Partnerships & Collaborations: Guest Posts, Podcasts, and Cross-Promotions24:07 Organic Growth Tactics: Referrals, Giveaways & Communities28:52 The Worst Channels Hurting Your Newsletter37:54 The Tier List Recap38:53 My Recommendation 40:09 Real Data Breakdown: Conversions & Revenue per Source45:01 What I've Learned From The Data

In this Q&A video, I answer questions about how to start, grow, and monetize a newsletter. I explain how to get 1,000 subscribers in 30 days using my “1K Challenge,” which includes daily posting, commenting, and outreach on platforms like LinkedIn or Instagram. I cover how niche is too niche, why cross-promotions between newsletters work best when both sides match clicks, and how to measure success beyond open rates by focusing on revenue and engagement. I also share thoughts on the future of newsletters— shorter formats, weekly cadence, and using them to drive product or service sales instead of relying only on ads.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Episode Questions & Timestamps00:00 Introduction & Q&A Overview00:18 Is it possible to get 1,000 subscribers in 30 days?09:58 How niche is too niche?11:15 How do you approach partnerships and cross-promotions?14:28 Can you still trust open rates and click-through rates?17:32 How many links are too many in a newsletter?18:20 How can you find and sell the right product to your audience?21:56 What's the next big shift in the newsletter industry?24:19 Is there opportunity for newsletter aggregators?

In this episode, I unveil the vision behind the new New Media Summit—our upcoming 2026 conference focused on the future of media—and how we're leveling it up with bigger speakers, more actionable sessions, and better networking. I also share why I'm shifting to a YouTube-first content strategy in 2025, how weekly Q&A episodes fit into that plan, and why newsletters remain the backbone of our business and monetization.New Media SummitFREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Timestamps:00:00 Podcast Direction & Content Strategy 02:21 Introducing New Media Summit 04:38 What You Can Expect This Year06:46 Networking, Community, and Venue Experience08:35 Our Commitment to Quality 

In this Q&A, I answer your biggest questions about building and scaling a newsletter in 2025. We cover everything from whether LinkedIn newsletters are still worth it, to what platform you should use (Beehiiv, Kit, Substack, or Klaviyo), and the most effective ways to grow your audience organically. I also share what I'd do if I had to start from scratch, how AI is reshaping content creation, when to pivot your strategy, and how to price your first sponsorships.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Episode Questions & Timestamps00:00 Introduction to Q&A00:26 The truth about LinkedIn newsletters in 202502:54 What newsletter business would you start if you had to begin from scratch tomorrow?07:43 Should you use Beehiiv, Kit, Substack, or Klaviyo?11:20 What are the best organic growth strategies for newsletters?14:06 How do you think about newsletter vs. YouTube content?16:16 How will AI impact the newsletter space?18:50 How do you decide when to pivot your content strategy?21:41 How should you communicate a publication name change to your audience?24:39 How do you approach newsletter sponsorship pricing?28:38 What's the best way to approach list cleaning and re-engagement?

In this week's Q&A, I break down the real tactics that work for growing and monetizing newsletters in 2025. I cover my personal content workflow, why newsletter recommendations are dead, and what actually matters for sponsors beyond list size. I also discuss local newsletters, when to start running paid ads, and the revenue potential at different subscriber levels.FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Episode Questions & Timestamps00:00 Introduction to weekly Q&A podcast00:46 How do you draft your newsletter each week?03:25 How do you curate your best links section?05:15 What growth tactics worked two years ago that are completely dead now?07:38 What growth tactics are working right now?09:19 What's your hot take on local newsletters?12:28 How do you overcome the fear of starting a media company?14:10 What metrics matter most for sponsors and list quality?17:33 When should you start running paid ads?19:57 How should you approach selling a premium newsletter offer?26:24 When should you hire someone to help with content?28:12 What revenue is possible at different subscriber levels?30:28 Should you be using Beehiiv Boosts or Sparkloop?32:01 Conclusion and wrap-up

Comment on the YouTube video if you have ideas on what content you want to see next: https://youtu.be/fm5O0lGLMuESubscribe to Ryan's YouTube channel: YouTube.com/@vibemarketingwithryanJoin Ryan's newsletter here >>Join Matt's newsletter here >>Matt and Ryan discuss why they're pausing the podcast after nearly two years, reflecting on what worked, what didn't, and where they're headed next. Timestamps00:00 The Announcement: Shutting Down the Podcast02:23 Podcast Performance: Analyzing Numbers and Trends10:20 Exploring Alternatives: New Directions for Content12:35 Individual Goals: Focus on Newsletters and YouTube20:43 Long-Term Strategy: Investing in Sustainable Channels30:05 Reflections: Lessons Learned from the Podcast Journey

Matt and Ryan discuss AI's role in advertising and content creation, and the 5 simplest ways to make your first $1000 online.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Exploring AI in Advertising02:55 Innovative Uses of AI for Content Creation05:54 The Future of AI in Marketing08:46 Leveraging AI for Solopreneurs12:02 Automating Newsletter Creation with AI15:06 Creative Approaches to Content Generation18:00 Monetizing Your Online Presence30:48 Strategies for Earning Your First $1,000 Online

FREE Guide: How to get your first 1000 newsletter subscribers in 30 days >>Daniel Bustamante is the COO at Premium Ghostwriting Academy and the founder of Funnel Breakdowns newsletter. He specializes in million-dollar email marketing prompts, tactics, and strategies for 6 and 7-figure creators on LinkedIn and X.Timestamps00:00 Introduction and Background02:56 Journey to Ship 30 for 3005:59 Building a Personal Brand on LinkedIn08:40 Growth Strategies on LinkedIn11:51 Engagement Tactics and Community Building15:00 Email List Growth Strategies18:02 Marketing Funnels and Email Sequences20:56 Insights from Hermosi and Industry Events24:05 Relaunching Ship 30 and Premium Ghostwriting Academy26:52 Conclusion and Future PlansLinks Mentionedhttps://www.linkedin.com/in/dbusta/https://funnelbreakdowns.com/

FREE GUIDE: How to get your first 1000 email subscribers in 30 days >>The Culturist is a newsletter with over 200,000 subscribers that explores art, literature, music, and the layered histories of culture and religion. Timestamps00:00 The Power of Content Ownership02:45 Transitioning from Social Media to Substack05:55 Rebranding and Building a Publication09:04 Navigating the Challenges of X (Twitter)11:49 Strategies for Engaging Content on X15:07 Expanding to Other Platforms: Instagram and Beyond17:40 The Importance of Evergreen Content20:54 Advice for Non-B2B Creators23:54 Building a Sustainable Audience26:51 Revenue Models and Subscriber Conversion29:49 Future Plans and Community EngagementLinks Mentionedhttps://www.theculturist.io/

FREE GUIDE: How to get your first 1000 email subscribers in 30 days >>In this conversation, Matt McGarry and Ryan Carr discuss the challenges and strategies for growing a newsletter audience and generating revenue. Chapters00:00 Scaling Webinar Strategies02:43 The Challenge of Subscriber Growth05:57 Consistency and Niche Selection08:53 Building an Engaged Audience11:56 Content Creation and Value Sharing14:58 Organic Growth Strategies18:01 Quality Over Quantity in Audience Building21:03 Tactical Growth Insights23:49 Leveraging Social Media for Growth27:00 Monetization Strategies for New Creators

Chris Miquel is the founder of SoVi Digital and Audience Bridge. He helps clients maximize deliverability, engagement, and email list growth. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Matt's agency GrowLetterEpisode Topics & Timestamps00:00 Introduction to Email Deliverability01:26 Understanding Email Service Providers (ESPs)04:10 The Importance of Custom Domains09:16 Email Authentication: DKIM, SPF, and DMARC12:33 Shared vs. Dedicated IPs17:31 Building a Base Sending Segment22:57 Managing Engagement and List Health30:18 Improving Inbox Placement38:01 The Future of Email and AI ImpactLinks Mentionedhttps://www.audiencebridge.io/https://www.youtube.com/@audiencebridge

Chris Hoffmann is the CEO of Hoffmann Brothers & Deutschmann Lane Holdings, leading home service brands across multiple cities. He scaled his family business from $9M to $150M+ in revenue. He is also the founder of The Path Less Traveled, a newsletter on growing service companies without outside capital.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Introduction to The Path Less Traveled02:52 Understanding the Audience and Content Strategy05:44 The Home Service Business Landscape08:54 Entrepreneurship Through Acquisition Insights11:56 The Media and Newsletter Journey14:55 Sponsorships and Monetization Strategies17:48 Tracking Performance-Based Sponsorships21:02 Leveraging Paid Subscriptions24:03 Onboarding and Welcome Email Strategies26:51 Using Social Media for Growth29:54 Paid Advertising Strategies32:57 Building Community and Engagement36:00 Final Thoughts and Future DirectionsLinks Mentionedhttps://www.linkedin.com/in/stlchrishoffmann/https://thepathlesstraveled.beehiiv.com/

Matt and Ryan Carr discuss webinar marketing and sharing strategies for boosting sign-ups, keeping audiences engaged, and increasing show-up rates. They also cover lessons from building courses, leveraging lead magnets, and using AI meta-prompting to structure content effectively.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 The Power of Webinars02:46 Paid Ads and Webinar Strategies05:49 Building an Audience and Community Engagement08:44 The Importance of Show-Up Rates12:03 Transitioning to a Course and Community Model15:08 Creating Effective Lead Magnets17:45 Meta Prompting for AI Tools20:40 Structuring Your Course for SuccessLinks Mentionedhttps://moodboard.beehiiv.com/ https://moodboard.beehiiv.com/p/5-prompts-for-building-in-lovable 

Matt shares his journey of building a successful writing business despite his dyslexia. He breaks down 12 actionable rules that helped him succeed.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Overcoming Dyslexia in Writing02:55 12 Rules for Writing Useful Content

Join the Write, Grow, Sell waitlist here >>Anastasia Negru is the cofounder of AffordiHome, a media brand focused on affordable properties in Europe. She discussed the growth of their newsletter, audience engagement strategies, revenue generation challenges, and the introduction of consultation services. The discussion highlights the importance of understanding customer needs, effective marketing strategies, and the potential for future growth in the real estate sector.Episode Topics & Timestamps00:00 Introduction to AffordiHome and Its Business Model02:51 Growth of the Newsletter and Subscriber Engagement05:53 Content Strategy and Audience Acquisition09:00 Revenue Generation and Business Challenges11:50 Consultation Services and Client Engagement14:46 Future Growth Strategies and Business Model ExplorationLinks Mentionedhttps://www.affordihome.com/ https://x.com/affordihome 

Matt and Ryan discuss various strategies for building an audience, leveraging AI in marketing, and innovative sales techniques. They share insights on content creation, the importance of copywriting, and the effectiveness of using Google Docs for marketing. They also highlight the value of building a media brand and the tools to help entrepreneurs streamline their processes.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction and Milestones02:58 Content Creation Strategies05:55 Leveraging AI in Marketing08:54 Building an Audience on LinkedIn11:39 Sales Strategies and Funnels17:58 Innovative Marketing Techniques23:45 Tool Recommendations for EntrepreneursLinks Mentionedhttps://moodboard.beehiiv.com/https://lovable.dev/

Jordan DiPietro is the former CEO of Hampton, a community business that's scaled to over $10M in annual revenue. Episode Topics & Timestamps00:00 Introduction to Hampton and Community Business Models03:07 Marketing Strategies for Community Growth05:56 Sales Process and Lead Conversion Techniques09:12 Content Marketing and Lead Generation12:09 The Role of MoneyWise Podcast in Community Engagement15:06 Building Relationships in Community Spaces18:04 Core Groups and In-Person Retreats21:12 The Evolution of Community Dynamics25:51 The Importance of In-Person Connections26:40 Confidentiality and Community Integrity27:57 Balancing Exclusivity and Growth30:57 Criteria for Membership in Exclusive Communities33:29 Staying Focused as a CEO35:38 The HubSpot Acquisition of The Hustle42:07 The Future of SaaS Companies Acquiring Media45:47 Jordan's Next Chapter: Writing and CoachingLinks MentionedJordan's newsletter: https://jordandipietro.beehiiv.com/ Jordan's website: https://jordandipietro.com/

Matt and Ryan discuss Ryan's recent venture into creating a newsletter focused on AI-assisted marketing workflows. He shares how he grew his AI-focused marketing newsletter from 0 to ~900 subscribers in 15 days using LinkedIn. The discussion covers effective content marketing tactics, the importance of high-quality lead magnets, and lessons learned from experimenting with email marketing. They also explore a case study of Ted Williams, who successfully launched a local newsletter with impressive engagement metrics.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction and Overview of New Ventures03:03 Growth Strategies for Newsletters06:04 Engagement Tactics on LinkedIn08:58 Shameless Content Marketing12:09 Lessons Learned from Subscriber Growth15:03 Experimenting with Email Marketing19:52 Case Study: Ted Williams and Local NewslettersLinks Mentionedhttps://moodboard.beehiiv.com/ 

Matt shares a step-by-step guide to launching a newsletter and landing your first 1,000 subscribers. He breaks down niche selection, category design, the “job to be done” framework, and tactical strategies for idea validation, social media outreach, and subscriber growth.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Introduction to Newsletter Growth03:09 Choosing the Right Niche06:07 Hyper Scale vs. Hyper Niche Newsletters08:56 Category Design and Unique Positioning11:55 Defining Your Job to Be Done14:57 Validating Your Idea and Gaining Subscribers19:48 Maximizing Your Announcement Post24:31 Building Your Subscriber Base25:11 Leveraging Social Media for Growth30:43 Converting Followers into Subscribers

Matt and Ryan share strategies for growing on LinkedIn, converting engagement into email subscribers, and building long-term content engines. They also explore video content, email optimization, and rebranding the podcast. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Growing Your Audience on LinkedIn02:42 Lead Magnet Strategies for Engagement06:52 The Challenges of Email Subscriber Growth08:07 Exploring Organic Channels for Email Signups11:18 The Shift to Video Content13:38 YouTube as a Growth Platform20:04 Finding Effective Content Formats24:51 The Long-Term Commitment to Audience Building25:48 Optimizing Email Engagement through Base Sending Segments30:05 Strategies for Managing Dormant Subscribers33:52 The Importance of Email Frequency and Engagement38:01 Rebranding and Expanding the Podcast's Focus44:18 Exploring New Terminology for Audience-First Businesses

Chenell Basilio is the founder of Growth in Reverse, a newsletter and podcast that reverse engineers how top creators grow their audiences to 50,000+ subscribers. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction and Background02:48 Content Creation Essentials05:58 Choosing the Right Platforms09:11 Niche Selection and Audience Engagement11:51 Strategies for Subscriber Growth14:50 Collaboration and Networking17:53 Tactics for First 1000 Subscribers27:58 Strategies for Growing Your Audience30:53 Leveraging Substack for Engagement34:29 The Power of Pop-Up Newsletters39:54 Analyzing Growth Metrics42:20 Building Community and Networking47:18 Business Models and Revenue StreamsLinks Mentionedhttps://growthinreverse.com/30-days-of-growth-list/

If you're running a “newsletter business” the way most people do, you're doomed to fail. To explain why and what to do now, I'll break down the history of newsletters and why founders and publishers must pivot to what I call newsletters 3.0.Want help building a media brand? Get in touch here: GrowLetter.com

Matt and Ryan discuss newsletter-first business ideas—from niche media brands to local community stories—sharing insights on engagement, monetization, and building with purpose.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Exploring Newsletter Business Ideas10:10 Dyslexic Advantage: A Media Opportunity20:04 Gamified Coding Challenges: Engaging Communities30:01 Local Community Connections: Humans of [Your Town]

Apply to attend: Audience.CampMatt and Ahrif give you a behind-the-scenes look into Audience Camp, a new event for founders and creators in Asheville, North Carolina, this fall. 

Matt McGarry discusses the concept of Negative CAC—how smart companies turn marketing into profit. He shares real-world examples from media and SaaS, showing how digital products and media can fuel growth and long-term profitability.Learn more about negative CAC: https://www.newsletteroperator.com/p/negative-cacWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Understanding Negative Customer Acquisition Cost (CAC)02:58 Examples of Negative CAC in Action05:53 The Role of Media Companies in Negative CAC08:59 Long-term Implications and Future of Negative CAC

Matt and Ryan discuss the digital transformation challenges facing legacy media, from shifting to subscription models to embracing email marketing. They explore innovative newsletter growth tactics, AI's role in democratizing software development, and evolving strategies for software acquisition. They also share how tools can serve as lead magnets, why community-building matters, and how micro ads can unlock new revenue for digital publishers.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 The State of Legacy Media Companies02:51 Challenges in Digital Marketing for Traditional Media06:04 Innovative Newsletter Strategies for Growth09:12 Opportunities in Legacy Media Transformation12:12 The Power of Email Marketing in Subscription Models14:49 The Future of Digital Products and Marketing Strategies23:39 The Evolving Landscape of Software Acquisition28:03 Harnessing AI for Web App Development33:11 Leveraging Tools as Lead Magnets38:51 Innovative Monetization Strategies in Newsletters43:12 Building Community Through Events

Matt shares actionable strategies for launching and growing a successful newsletter from the ground up.Get the first 1,000 subscribers guide: https://www.newsletteroperator.com/p/first-1000-newsletter-subscribersWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Getting Started with Newsletters09:03 Strategies for Growing Your Subscriber Base17:53 Building Relationships and Feedback Mechanisms

Matt shares how he plans to double his email list from 50K to 100K and boost revenue in the process. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Growing the Email List: Strategies and Goals08:06 Navigating Social Media Changes: From Twitter to LinkedIn15:51 The Power of Webinars in Building Trust and Conversions24:05 Key Takeaways: Lessons from 50,000 Subscribers

Matt discusses his top strategies for launching and growing a successful newsletter. He covers why starting with a weekly send builds consistency, how to use social media to grow your list, and ways to convert followers into subscribers. He also dives into lead magnets, monetization through ads, and the power of optimized profiles and direct messaging.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Choosing the Right Newsletter Frequency03:07 Building Your Email List Effectively05:52 Converting Social Media Followers to Subscribers09:00 Creating Effective Lead Magnets11:55 Scaling Your Newsletter for Revenue

Matt discusses how to grow and monetize a newsletter on just $20 a day. He shares how to use Meta ads for lead generation, structure campaigns that convert, and the importance of testing creative. Matt also dives into smart monetization tactics—like paid recommendations—to cover ad spend and start earning fast.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com

Matt and Ryan discuss how AI is transforming marketing, with a focus on content creation, advertising, and newsletter strategy. They also explore building effective newsletter funnels, increasing engagement and conversions, and adapting to new monetization models beyond conventional ad-based approaches.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Exploring AI in Marketing03:00 Creative Applications of AI Tools06:08 Streamlining Content Creation with AI08:57 Building Effective Newsletter Funnels12:06 Maximizing Engagement and Conversion Rates14:58 The Future of Newsletters and Monetization Strategies

Join the free live training here: newsletter.trainingThis episode is an update on the status of this podcast, our content, and what's happening next. ---Other links:- Subscribe to the YouTube channel.- Join my free newsletter. - Ask a question.