Jason Woodruff, founder of The Pour Over, shares how to build a mission-driven newsletter, focusing on content quality, subscriber engagement, and sponsor-driven growth. He also offers insights on managing advertiser relationships and use referrals to build a loyal, sustainable audience.

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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 The Genesis of The Pour Over

02:52 Growth and Scaling Challenges

06:10 Building a Subscriber Base

08:51 Content Quality and Reader Engagement

12:13 The Future of Newsletters and Podcasts

15:07 Team Dynamics and Content Creation

17:56 Advertising Strategies and Monetization

26:55 Rebuilding Advertiser Relationships

32:45 The Importance of Ad Copy

35:08 Growth Strategies and Paid Advertising

41:25 Referral Strategies for Subscriber Growth

46:36 Securing Sponsorships and Advertisers

Links Mentioned

Thepourover.org

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Speakers include:

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Roslyn McLarty, is an executive coach and founder at Within. She is also the co-founder of The Gist, a sports media company for women and underserved sports fans. In this episode, Roslyn shares key insights on identifying market gaps, building a brand with a strong mission, and the strategies used to grow their audience from a few hundred to hundreds of thousands of subscribers. She also discuss managing burnout, and fostering self-growth, and introduces Within, a coaching business focused on trust-based client relationships.

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 Journey Begins: From Beta to Launch

02:58

Identifying the Market Gap: The Gist's Unique Proposition

06:02

Building the Brand: Mission and Values

08:47

Growing the Audience: Strategies and Early Successes

12:10

Scaling Up: From Local to National

15:01

Navigating Growth: Lessons Learned and Key Metrics

17:54

Creative Marketing: Guerrilla Tactics and Launch Events

20:54

The Importance of Mission-Driven Growth

24:02

Partnerships and Collaborations: Expanding Reach

27:02

Self-List Cleaning and Giveaway Strategy

35:01

Expansion and New Ventures

37:32

The Birth of Within: A Personal Development Platform

41:08

Understanding and Preventing Burnout

50:43

Growth Strategy for Coaching Business

Links Mentioned

Join Roslyn's newsletter, Within