The Little-Known Way Creators Are Building BILLION Dollar Businesses

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