Newsletter Operator
Learn how to grow and monetize your newsletter! We interview the best newsletter operators, founders, and creators on how they grow their audiences and make money. Hosted by Matt McGarry and Ryan Carr.
Episodes
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 ho...
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 subscribe...
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Matt and Ryan discuss why they’re pausing the podcast after nearly two years, reflecting on what worked, what didn’t, and where they’r...
Matt and Ryan discuss AI's role in advertising and content creation, and the 5 simplest ways to make your first $1000 online.
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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 @ry...
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.
Timestamps
00:00 Introduction and Background
02:56 Journey to Ship 30 for 30
05...
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.
Timestamps
00:00 The Power of Content Ownership
02:45 Transitioning from Social Media to Substack
05:55 Rebranding and Building a Publication
09:04 Navigating the Challe...
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.
Chapters
00:00 Scaling Webinar Strategies
02:43 The Challenge of Subscriber Growth
05:57 Consistency and Niche Selection
08:53 Building an Engaged Audience
11:56 Content Creation and Value ...
Chris Miquel is the founder of SoVi Digital and Audience Bridge. He helps clients maximize deliverability, engagement, and email list growth.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com
- Work with Matt's agency GrowLetter
Episode Topics & Timestamps
00:00 Introduction to Email Deliverability
01:26 Unders...
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.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter...
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.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.co...
Matt shares his journey of building a successful writing business despite his dyslexia. He breaks down 12 actionable rules that helped him succeed.
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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 Overcoming Dyslexia in Writing
02:55 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...
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.
Jordan DiPietro is the former CEO of Hampton, a community business that's scaled to over $10M in annual revenue.
Episode Topics & Timestamps
00:00 Introduction to Hampton and Community Business Models
03:07 Marketing Strategies for Community Growth
05:56 Sales Process and Lead Conversion Techniques
09:12 Content Marketing and Lead Generation
12:09 The Role of MoneyWise Podcast in Communit...
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 ...
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.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com
Epi...
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.com
- Work with Ryan's agency Tailwind
- Work with Matt&...
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.com
- Work with Ryan's agency Tailwind
- Work with Matt's agency GrowLetter
Follow Matt McGarry @JMatthewMc...
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
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