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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• 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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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.

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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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

• 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 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