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.com

• Work with Ryan's agency Tailwind
• Work with Matt's agency GrowLetter

Follow 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

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.com

Episode Topics & Timestamps

00:00 Getting Started with Newsletters

09:03 Strategies for Growing Your Subscriber Base

17:53 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.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.com

Episode 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

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.com

• Work with Ryan's agency Tailwind
• Work with Matt's agency GrowLetter

Follow 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

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: jon@smartblogger.com

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?

Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com

• Work with Ryan's agency Tailwind
• Work with Matt's agency GrowLetter

Follow 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