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

• 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