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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 Sharing
14:58 Organic Growth Strategies
18:01 Quality Over Quantity in Audience Building
21:03 Tactical Growth Insights
23:49 Leveraging Social Media for Growth
27:00 Monetization Strategies for New Creators

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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• Work with Matt's agency GrowLetter

Episode Topics & Timestamps

00:00 Introduction to Email Deliverability

01:26 Understanding Email Service Providers (ESPs)

04:10 The Importance of Custom Domains

09:16 Email Authentication: DKIM, SPF, and DMARC

12:33 Shared vs. Dedicated IPs

17:31 Building a Base Sending Segment

22:57 Managing Engagement and List Health

30:18 Improving Inbox Placement

38:01 The Future of Email and AI Impact

Links Mentioned

https://www.audiencebridge.io/

https://www.youtube.com/@audiencebridge

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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Episode Topics & Timestamps

00:00 Introduction to The Path Less Traveled

02:52 Understanding the Audience and Content Strategy

05:44 The Home Service Business Landscape

08:54 Entrepreneurship Through Acquisition Insights

11:56 The Media and Newsletter Journey

14:55 Sponsorships and Monetization Strategies

17:48 Tracking Performance-Based Sponsorships

21:02 Leveraging Paid Subscriptions

24:03 Onboarding and Welcome Email Strategies

26:51 Using Social Media for Growth

29:54 Paid Advertising Strategies

32:57 Building Community and Engagement

36:00 Final Thoughts and Future Directions

Links Mentioned

https://www.linkedin.com/in/stlchrishoffmann/

https://thepathlesstraveled.beehiiv.com/

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.

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 Power of Webinars

02:46 Paid Ads and Webinar Strategies

05:49 Building an Audience and Community Engagement

08:44 The Importance of Show-Up Rates

12:03 Transitioning to a Course and Community Model

15:08 Creating Effective Lead Magnets

17:45 Meta Prompting for AI Tools

20:40 Structuring Your Course for Success

Links Mentioned

https://moodboard.beehiiv.com/ 

https://moodboard.beehiiv.com/p/5-prompts-for-building-in-lovable 

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

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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.

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 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.

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 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