Episódios
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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.
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Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Exploring Newsletter Business Ideas
10:10 Dyslexic Advantage: A Media Opportunity
20:04 Gamified Coding Challenges: Engaging Communities
30:01 Local Community Connections: Humans of [Your Town]
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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 & Timestamps
00:00 Understanding Negative Customer Acquisition Cost (CAC)
02:58 Examples of Negative CAC in Action
05:53 The Role of Media Companies in Negative CAC
08:59 Long-term Implications and Future of Negative CAC
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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?
Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 The State of Legacy Media Companies
02:51 Challenges in Digital Marketing for Traditional Media
06:04 Innovative Newsletter Strategies for Growth
09:12 Opportunities in Legacy Media Transformation
12:12 The Power of Email Marketing in Subscription Models
14:49 The Future of Digital Products and Marketing Strategies
23:39 The Evolving Landscape of Software Acquisition
28:03 Harnessing AI for Web App Development
33:11 Leveraging Tools as Lead Magnets
38:51 Innovative Monetization Strategies in Newsletters
43:12 Building Community Through Events
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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-subscribers
Want more content like this?
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps
00:00 Getting Started with Newsletters
09:03 Strategies for Growing Your Subscriber Base
17:53 Building Relationships and Feedback Mechanisms
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Matt shares how he plans to double his email list from 50K to 100K and boost revenue in the process.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com
Episode Topics & Timestamps
00:00 Growing the Email List: Strategies and Goals
08:06 Navigating Social Media Changes: From Twitter to LinkedIn
15:51 The Power of Webinars in Building Trust and Conversions
24:05 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 & Timestamps
00:00 Choosing the Right Newsletter Frequency
03:07 Building Your Email List Effectively
05:52 Converting Social Media Followers to Subscribers
09:00 Creating Effective Lead Magnets
11:55 Scaling Your Newsletter for Revenue
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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.
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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?
Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Exploring AI in Marketing
03:00 Creative Applications of AI Tools
06:08 Streamlining Content Creation with AI
08:57 Building Effective Newsletter Funnels
12:06 Maximizing Engagement and Conversion Rates
14:58 The Future of Newsletters and Monetization Strategies
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Jon Morrow is the founder of Smarter Blogger, one of the world's largest sites for writing and blogging. He's created 7 different courses with 7 figures in sales each.
Episode Topics & Timestamps
00:00 Finding Your Niche
04:03 Jon's story
10:00 Building a Business from Scratch
14:53 Strategies for Launching and Growing Your Brand
20:03 Effective Email Marketing Techniques
23:04 The Journey of Course Creation
25:35 Framework for Information Products
27:58 Structuring Coaching Programs
30:08 Optimizing Course Structure for Success
34:20 Evaluating Course Effectiveness with Scorecards
37:10 Building Credibility and Trust
41:39 Navigating Ethical Marketing Practices
Links Mentioned
https://smartblogger.com/
Great video on Jon's story: How He Made $10M To Pay For Medical Bills
7-figure course scorecard.
Jon's email: [email protected]
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Save your seat at the event: newslettermarketingsummit.com
Episode Description:
Matt and Ryan discuss strategies for building successful newsletters and email marketing. They also share the importance of surveys for data, segmentation for targeted messaging, niche expert newsletters, the 9-word email strategy, and repurposing valuable content.
Want more content like this?
Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Introduction and Event Overview
01:47 The Artist's Success Story
06:11 Building an Email List and Marketing Strategy
08:53 The Power of Surveys and Data Collection
13:56 Segmentation and Custom Messaging
17:57 Niche Expert Framework for Newsletters
23:09 The Nine Word Email Strategy
28:53 The Newsletter Flywheel Effect
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Check out Ezoic: ezoic.com
Save your seat at Newsletter Marketing Summit: newslettermarketingsummit.com
Tyler Bishop is an award-winning marketer, Chief Marketing Officer of Ezoic, and founder of Pubtelligence at Google. He discusses the shift from third-party to first-party data in advertising and its impact on publisher revenue. He shares insights on evolving targeting methods, data privacy regulations, and challenges for publishers.Episode Topics & Timestamps
00:00 Understanding the Shift in Ad Revenue
12:09 The Evolution of Targeting: From Contextual to First-Party Data
20:40 The Value of First-Party Data in Advertising
27:58 The Art of Publishing and Business Success
29:53 The Evolution of Advertising Models
32:05 Maximizing Revenue through Advertising
34:04 Understanding Ad Revenue Trends
36:19 The Value of Traffic Sources
43:22 Leveraging First-Party Data for Growth
49:16 Identifying the Right Publishers for Programmatic Ads
50:56 The Future of Newsletter Advertising
53:01 Collecting Valuable User Data
Links Mentioned
https://www.ezoic.com/
https://www.youtube.com/@Ezoic
adrevenueindex.ezoic.com
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This episode is sponsored by Playbookz: Playbookz.co
Ted co-founded Charlotte Agenda, which led to its remarkable $5 million acquisition by Axios. He currently writes Tiny Money—a local and personal finance newsletter.
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Join our free newsletter for growth and monetization tactics:https://www.newsletteroperator.com/subscribe
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Save your seat at our event: newslettermarketingsummit.com
Work with Matt's agency GrowLetter
Kendall Baker is the founder of Sports Internet (acquired by Axios), the first newsletter writer at The Hustle, and now a Senior Writer at Yahoo Sports.
He's known as the "Newsletter Godfather" because he's pioneered newsletter content and has written and published more newsletters to more readers than almost anyone.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com -
Get Justin's new book: SponsorMagnet.com
Work with Matt's agency GrowLetter
Justin Moore is a sponsorship coach and the author of Sponsor Magnet: How to Attract, Price, and Execute Your Dream Brand Partnerships
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com
Episode Topics & Timestamps00:00 The Importance of Custom Pricing for Creators
09:16 Creating a Comprehensive Sponsorship Strategy
27:05 Attracting Brands: The STP Framework
28:32 Navigating the Complexities of Pricing Sponsorships
29:00 Understanding the ARC Framework for Collaborations
32:19 Pricing Strategies Based on Brand Goals
34:46 Creating Compelling Sponsorship Packages
39:04 Innovative Collaboration Examples
43:52 Crafting Effective Outreach Strategies
57:10 The Importance of Execution in Sponsorships
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Ali Qureshi is the co-founder of Adcrate. He shares strategies on effective ads for platforms like Meta and TikTok. He also shares static and video formats, copywriting, leveraging AI, hook rates, video production and more.
Want more content like this?
Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Introduction to AdCrate and Growth Strategy
02:56 The Importance of Ad Creative in Paid Advertising
05:47 Navigating Media Platforms: Meta vs. TikTok
08:53 Static vs. Video Creatives: Balancing Production and Impact
11:49 Effective Static Ad Formats and Testing Strategies
15:09 Common Mistakes in Ad Creation and Copywriting Tips
17:55 Leveraging AI for Ad Copy and Customer Insights
20:47 Innovative Ad Formats: Memes and Interface Hacking
25:42 Understanding Hook Rates and Audience Engagement
28:10 Navigating Video Content Creation on a Budget
35:09 The Importance of Script Writing for Ads
40:50 Exploring Effective Video Lengths and Frameworks
43:40 Utilizing Motion Graphics for Enhanced Engagement
46:34 Iterating and Testing Ads for Success
Links Mentionedhttps://www.adcrate.co/
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Matt and Ryan discuss the Honey scandal, trends for 2025, focusing on YouTube, newsletters, and the shift from vanity metrics to revenue. They also explore AI workflows, B2B newsletters, the creator-in-residence model, and the future of platforms like Upwork and overseas recruiting and more.
Want more content like this?
Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Holiday Reflections and New Beginnings
02:03 The Honey Scandal Explained
17:48 Trends for 2025: Buying and Selling Insights
27:33 The Substack Ecosystem and Creator Independence
31:27 AI-Assisted Workflows for Content Creators
33:22 The Shift from Vanity Metrics to Revenue Focus
34:20 Emerging Newsletter Ad Networks
39:00 The Rise of B2B Newsletters and Creators
41:24 Challenges of Premium Newsletters
44:43 The Creator-in-Residence Model
48:55 The Future of Overseas Recruiting Agencies
Links Mentioned
https://newslettermarketingsummit.com/
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Here are the links:
- Join Write, Grow Sell here >>
- Register for the free live training here >> -
Matt and Ryan discuss what happened in the newsletter industry and their businesses in 2024.
Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Want more content like this?
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
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Tommy Clark, the CEO of Compound Social and the co-founder of Bluecast AI, shares strategies for growing an audience on LinkedIn, creating engaging content, personal branding, and focusing on value propositions.
Want more content like this?
Work with Ryan's agency Tailwind Work with Matt's agency GrowLetter
Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 The Importance of Clear Value Proposition
03:13 Audience Growth Strategies on LinkedIn
06:04 Content Creation Fundamentals
08:58 Optimizing Content for Engagement
11:47 Leveraging Controversy in Content
14:57 The Power of Personal Stories in Content
23:58 Reflecting on Weekly Engagements
24:57 The Importance of Specificity in Content
25:51 Understanding Engagement on LinkedIn
27:44 Strategies for Boosting Engagement
29:38 The Risks of Engagement Hacking
30:36 Building an Organic Audience
32:01 Converting Followers into Customers
34:50 Exploring Growth Hacks on LinkedIn
36:14 Leveraging LinkedIn Video Content
39:04 Navigating Links in Posts
40:55 Insights on LinkedIn Newsletters
Links Mentioned
https://x.com/tclarkmedia
https://www.linkedin.com/in/tclarkmedia/
https://www.bluecast.ai/
https://www.compoundcontentstudio.com/
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