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.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 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]

Apply to attend: Audience.Camp

Matt 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-cac

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 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

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