Why paid paywall newsletters struggle

Most creators have no idea how powerful newsletters are right now. In this episode, you’ll learn why email is outperforming every social platform and how top operators are turning simple weekly emails into six-figure profit machines. Kevin King and Norm Farrar break down their own newsletter playbooks (including selling $4,500 dedicated sends and hitting 62 percent open rates) and sit down with Matt McGarry, widely regarded as the newsletter expert behind The Hustle, HubSpot, and Newsletter Operator. Matt reveals exactly why newsletters outperform every other channel for trust, retention, monetization, and audience ownership. You’ll hear the mistakes beginners make, how to actually grow a newsletter, and what it takes to turn email into a real business. If you’re a marketer, founder, creator, or ecommerce operator, this will change how you think about email forever.

What You’ll Learn:

• Why newsletters outperform social and YouTube for monetization

• How Kevin charges $4,500 per email and sells out months in advance

• Newsletter vs. marketing email: the real difference

• How Matt built newsletter systems from The Hustle to HubSpot

• Why most newsletters fail after 10 issues

• How to grow from 0 to thousands of subscribers

• How to design newsletters people actually read

• Deliverability tactics to stay out of Promotions

• How to segment your list for 5–10x higher revenue

• How to blend AI with human writing without sounding robotic

• Why churn kills paid newsletters and what to do instead

• How to use LinkedIn, YouTube, and Instagram to grow email fast

• Real-world monetization strategies that actually work in 2025

Chapters

00:00 The Power of Newsletters

00:46 'Email is Dead' Myth

01:43 The Billion Dollar Sellers Newsletter

03:29 Introducing Matt

04:22 Matt's Journey

08:54 Consistency in Newsletters

14:10 Editorial vs. Promotional Emails

27:52 Effective Newsletter Strategies for Beginners

39:57 LinkedIn Newsletters: Are They Worth It?

40:38 LinkedIn Newsletters

43:04 Organic vs. Paid Newsletters

43:18 Challenges of Paid Newsletters

48:26 Newsletter Design Tips

50:29 AI in Newsletter Writing

01:01:24 Deliverability Strategies

01:11:09 Power of Email Segmentation

01:19:55 Final Thoughts

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