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.

Want more content like this?

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

• 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

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 @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

• 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 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]

Apply to attend: Audience.Camp

Matt 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.