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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 for future growth in the real estate sector.
Episode Topics & Timestamps
00:00 Introduction to AffordiHome and Its Business Model
02:51 Growth of the Newsletter and Subscriber Engagement
05:53 Content Strategy and Audience Acquisition
09:00 Revenue Generation and Business Challenges
11:50 Consultation Services and Client Engagement
14:46 Future Growth Strategies and Business Model Exploration
Links Mentioned
https://www.affordihome.com/
https://x.com/affordihome
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.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com
Follow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Introduction and Milestones
02:58 Content Creation Strategies
05:55 Leveraging AI in Marketing
08:54 Building an Audience on LinkedIn
11:39 Sales Strategies and Funnels
17:58 Innovative Marketing Techniques
23:45 Tool Recommendations for Entrepreneurs
Links Mentioned
https://moodboard.beehiiv.com/
https://lovable.dev/
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 Community Engagement
15:06 Building Relationships in Community Spaces
18:04 Core Groups and In-Person Retreats
21:12 The Evolution of Community Dynamics
25:51 The Importance of In-Person Connections
26:40 Confidentiality and Community Integrity
27:57 Balancing Exclusivity and Growth
30:57 Criteria for Membership in Exclusive Communities
33:29 Staying Focused as a CEO
35:38 The HubSpot Acquisition of The Hustle
42:07 The Future of SaaS Companies Acquiring Media
45:47 Jordan's Next Chapter: Writing and Coaching
Links Mentioned
Jordan's newsletter: https://jordandipietro.beehiiv.com/
Jordan's website: https://jordandipietro.com/
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 Williams, who successfully launched a local newsletter with impressive engagement metrics.
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Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com
Follow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Introduction and Overview of New Ventures
03:03 Growth Strategies for Newsletters
06:04 Engagement Tactics on LinkedIn
08:58 Shameless Content Marketing
12:09 Lessons Learned from Subscriber Growth
15:03 Experimenting with Email Marketing
19:52 Case Study: Ted Williams and Local Newsletters
Links Mentioned
https://moodboard.beehiiv.com/
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
Episode Topics & Timestamps
00:00 Introduction to Newsletter Growth
03:09 Choosing the Right Niche
06:07 Hyper Scale vs. Hyper Niche Newsletters
08:56 Category Design and Unique Positioning
11:55 Defining Your Job to Be Done
14:57 Validating Your Idea and Gaining Subscribers
19:48 Maximizing Your Announcement Post
24:31 Building Your Subscriber Base
25:11 Leveraging Social Media for Growth
30:43 Converting Followers into Subscribers
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
Follow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Growing Your Audience on LinkedIn
02:42 Lead Magnet Strategies for Engagement
06:52 The Challenges of Email Subscriber Growth
08:07 Exploring Organic Channels for Email Signups
11:18 The Shift to Video Content
13:38 YouTube as a Growth Platform
20:04 Finding Effective Content Formats
24:51 The Long-Term Commitment to Audience Building
25:48 Optimizing Email Engagement through Base Sending Segments
30:05 Strategies for Managing Dormant Subscribers
33:52 The Importance of Email Frequency and Engagement
38:01 Rebranding and Expanding the Podcast's Focus
44:18 Exploring New Terminology for Audience-First Businesses
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
Follow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.
Episode Topics & Timestamps
00:00 Introduction and Background
02:48 Content Creation Essentials
05:58 Choosing the Right Platforms
09:11 Niche Selection and Audience Engagement
11:51 Strategies for Subscriber Growth
14:50 Collaboration and Networking
17:53 Tactics for First 1000 Subscribers
27:58 Strategies for Growing Your Audience
30:53 Leveraging Substack for Engagement
34:29 The Power of Pop-Up Newsletters
39:54 Analyzing Growth Metrics
42:20 Building Community and Networking
47:18 Business Models and Revenue Streams
Links Mentioned
https://growthinreverse.com/30-days-of-growth-list/
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
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]
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