Newsletter Operator

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.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Exploring Newsletter Business Ideas10:10 Dyslexic Advantage: A Media Opportunity20:04 Gamified Coding Challenges: Engaging Communities30:01 Local Community Connections: Humans of [Your Town]

Apply to attend: Audience.CampMatt 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. 

Matt McGarry discusses the concept of Negative CAC—how smart companies turn marketing into profit. He shares real-world examples from media and SaaS, showing how digital products and media can fuel growth and long-term profitability.Learn more about negative CAC: https://www.newsletteroperator.com/p/negative-cacWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Understanding Negative Customer Acquisition Cost (CAC)02:58 Examples of Negative CAC in Action05:53 The Role of Media Companies in Negative CAC08:59 Long-term Implications and Future of Negative CAC

Matt and Ryan discuss the digital transformation challenges facing legacy media, from shifting to subscription models to embracing email marketing. They explore innovative newsletter growth tactics, AI's role in democratizing software development, and evolving strategies for software acquisition. They also share how tools can serve as lead magnets, why community-building matters, and how micro ads can unlock new revenue for digital publishers.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 The State of Legacy Media Companies02:51 Challenges in Digital Marketing for Traditional Media06:04 Innovative Newsletter Strategies for Growth09:12 Opportunities in Legacy Media Transformation12:12 The Power of Email Marketing in Subscription Models14:49 The Future of Digital Products and Marketing Strategies23:39 The Evolving Landscape of Software Acquisition28:03 Harnessing AI for Web App Development33:11 Leveraging Tools as Lead Magnets38:51 Innovative Monetization Strategies in Newsletters43:12 Building Community Through Events

Matt shares actionable strategies for launching and growing a successful newsletter from the ground up.Get the first 1,000 subscribers guide: https://www.newsletteroperator.com/p/first-1000-newsletter-subscribersWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Getting Started with Newsletters09:03 Strategies for Growing Your Subscriber Base17:53 Building Relationships and Feedback Mechanisms

Matt shares how he plans to double his email list from 50K to 100K and boost revenue in the process. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Growing the Email List: Strategies and Goals08:06 Navigating Social Media Changes: From Twitter to LinkedIn15:51 The Power of Webinars in Building Trust and Conversions24:05 Key Takeaways: Lessons from 50,000 Subscribers

Matt discusses his top strategies for launching and growing a successful newsletter. He covers why starting with a weekly send builds consistency, how to use social media to grow your list, and ways to convert followers into subscribers. He also dives into lead magnets, monetization through ads, and the power of optimized profiles and direct messaging.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comEpisode Topics & Timestamps00:00 Choosing the Right Newsletter Frequency03:07 Building Your Email List Effectively05:52 Converting Social Media Followers to Subscribers09:00 Creating Effective Lead Magnets11:55 Scaling Your Newsletter for Revenue

Matt discusses how to grow and monetize a newsletter on just $20 a day. He shares how to use Meta ads for lead generation, structure campaigns that convert, and the importance of testing creative. Matt also dives into smart monetization tactics—like paid recommendations—to cover ad spend and start earning fast.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.com

Matt and Ryan discuss how AI is transforming marketing, with a focus on content creation, advertising, and newsletter strategy. They also explore building effective newsletter funnels, increasing engagement and conversions, and adapting to new monetization models beyond conventional ad-based approaches.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Exploring AI in Marketing03:00 Creative Applications of AI Tools06:08 Streamlining Content Creation with AI08:57 Building Effective Newsletter Funnels12:06 Maximizing Engagement and Conversion Rates14:58 The Future of Newsletters and Monetization Strategies

Join the free live training here: newsletter.trainingThis episode is an update on the status of this podcast, our content, and what's happening next. ---Other links:- Subscribe to the YouTube channel.- Join my free newsletter. - Ask a question. 

Jon Morrow is the founder of Smarter Blogger, one of the world's largest sites for writing and blogging. He's created 7 different courses with 7 figures in sales each.Episode Topics & Timestamps00:00 Finding Your Niche 04:03 Jon's story10:00 Building a Business from Scratch14:53 Strategies for Launching and Growing Your Brand20:03 Effective Email Marketing Techniques23:04 The Journey of Course Creation25:35 Framework for Information Products27:58 Structuring Coaching Programs30:08 Optimizing Course Structure for Success34:20 Evaluating Course Effectiveness with Scorecards37:10 Building Credibility and Trust41:39 Navigating Ethical Marketing PracticesLinks Mentionedhttps://smartblogger.com/Great video on Jon's story: How He Made $10M To Pay For Medical Bills7-figure course scorecard. Jon's email: jon@smartblogger.com 

Save your seat at the event: newslettermarketingsummit.comEpisode Description:Matt and Ryan discuss strategies for building successful newsletters and email marketing. They also share the importance of surveys for data, segmentation for targeted messaging, niche expert newsletters, the 9-word email strategy, and repurposing valuable content.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction and Event Overview01:47 The Artist's Success Story06:11 Building an Email List and Marketing Strategy08:53 The Power of Surveys and Data Collection13:56 Segmentation and Custom Messaging17:57 Niche Expert Framework for Newsletters23:09 The Nine Word Email Strategy28:53 The Newsletter Flywheel Effect

Check out Ezoic: ezoic.comSave your seat at Newsletter Marketing Summit: newslettermarketingsummit.comTyler Bishop is an award-winning marketer, Chief Marketing Officer of Ezoic, and founder of Pubtelligence at Google. He discusses the shift from third-party to first-party data in advertising and its impact on publisher revenue. He shares insights on evolving targeting methods, data privacy regulations, and challenges for publishers. Episode Topics & Timestamps00:00 Understanding the Shift in Ad Revenue12:09 The Evolution of Targeting: From Contextual to First-Party Data20:40 The Value of First-Party Data in Advertising27:58 The Art of Publishing and Business Success29:53 The Evolution of Advertising Models32:05 Maximizing Revenue through Advertising34:04 Understanding Ad Revenue Trends36:19 The Value of Traffic Sources43:22 Leveraging First-Party Data for Growth49:16 Identifying the Right Publishers for Programmatic Ads50:56 The Future of Newsletter Advertising53:01 Collecting Valuable User DataLinks Mentionedhttps://www.ezoic.com/https://www.youtube.com/@Ezoicadrevenueindex.ezoic.com

Tyler Morin is the founder of The Water Coolest, a newsletter that offers irreverent takes on business and finance news. He shares insights on audience growth, monetization, Barstool Sports' acquisition, reclaiming his newsletter, and the future of ad-driven and B2B content.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction to Tyler Morin and Water Coolest02:59 The Journey to Founding Water Coolest06:03 Building an Audience: Strategies and Insights09:01 Monetization and Transitioning to Full-Time12:00 Early Sponsorships and Learning from Mistakes14:58 Crafting an Irreverent Newsletter17:59 The Evolution of Humor in Newsletters22:48 Navigating Acquisitions: The Barstool Experience30:11 The Changing Landscape of Ad Rates34:41 Building a Newsletter at Barstool39:46 The Return of The Water Coolest42:50 Consulting: Helping Others Build Their Media Businesses

This episode is sponsored by Playbookz: Playbookz.coTed co-founded Charlotte Agenda, which led to its remarkable $5 million acquisition by Axios. He currently writes Tiny Money—a local and personal finance newsletter.Want more content like this?Join our free newsletter for growth and monetization tactics: https://www.newsletteroperator.com/subscribe

Save your seat at our event: newslettermarketingsummit.comKendall Baker is the founder of Sports Internet (acquired by Axios), the first newsletter writer at The Hustle, and now a Senior Writer at Yahoo Sports. He's known as the "Newsletter Godfather" because he's pioneered newsletter content and has written and published more newsletters to more readers than almost anyone. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Matt's agency GrowLetter

Get Justin's new book: SponsorMagnet.comJustin Moore is a sponsorship coach and the author of Sponsor Magnet: How to Attract, Price, and Execute Your Dream Brand PartnershipsWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Matt's agency GrowLetterEpisode Topics & Timestamps00:00 The Importance of Custom Pricing for Creators09:16 Creating a Comprehensive Sponsorship Strategy27:05 Attracting Brands: The STP Framework28:32 Navigating the Complexities of Pricing Sponsorships29:00 Understanding the ARC Framework for Collaborations32:19 Pricing Strategies Based on Brand Goals34:46 Creating Compelling Sponsorship Packages39:04 Innovative Collaboration Examples43:52 Crafting Effective Outreach Strategies57:10 The Importance of Execution in Sponsorships

Ali Qureshi is the co-founder of Adcrate. He shares strategies on effective ads for platforms like Meta and TikTok. He also shares static and video formats, copywriting, leveraging AI, hook rates, video production and more.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction to AdCrate and Growth Strategy02:56 The Importance of Ad Creative in Paid Advertising05:47 Navigating Media Platforms: Meta vs. TikTok08:53 Static vs. Video Creatives: Balancing Production and Impact11:49 Effective Static Ad Formats and Testing Strategies15:09 Common Mistakes in Ad Creation and Copywriting Tips17:55 Leveraging AI for Ad Copy and Customer Insights20:47 Innovative Ad Formats: Memes and Interface Hacking25:42 Understanding Hook Rates and Audience Engagement28:10 Navigating Video Content Creation on a Budget35:09 The Importance of Script Writing for Ads40:50 Exploring Effective Video Lengths and Frameworks43:40 Utilizing Motion Graphics for Enhanced Engagement46:34 Iterating and Testing Ads for SuccessLinks Mentionedhttps://www.adcrate.co/

Matt and Ryan discuss the Honey scandal, trends for 2025, focusing on YouTube, newsletters, and the shift from vanity metrics to revenue. They also explore AI workflows, B2B newsletters, the creator-in-residence model, and the future of platforms like Upwork and overseas recruiting and more.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Holiday Reflections and New Beginnings02:03 The Honey Scandal Explained17:48 Trends for 2025: Buying and Selling Insights27:33 The Substack Ecosystem and Creator Independence31:27 AI-Assisted Workflows for Content Creators33:22 The Shift from Vanity Metrics to Revenue Focus34:20 Emerging Newsletter Ad Networks39:00 The Rise of B2B Newsletters and Creators41:24 Challenges of Premium Newsletters44:43 The Creator-in-Residence Model48:55 The Future of Overseas Recruiting AgenciesLinks Mentionedhttps://newslettermarketingsummit.com/

Here are the links:- Join Write, Grow Sell here >>- Register for the free live training here >>

Matt and Ryan discuss what happened in the newsletter industry and their businesses in 2024.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Tommy Clark, the CEO of Compound Social and the co-founder of Bluecast AI, shares strategies for growing an audience on LinkedIn, creating engaging content, personal branding, and focusing on value propositions. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 The Importance of Clear Value Proposition03:13 Audience Growth Strategies on LinkedIn06:04 Content Creation Fundamentals08:58 Optimizing Content for Engagement11:47 Leveraging Controversy in Content14:57 The Power of Personal Stories in Content23:58 Reflecting on Weekly Engagements24:57 The Importance of Specificity in Content25:51 Understanding Engagement on LinkedIn27:44 Strategies for Boosting Engagement29:38 The Risks of Engagement Hacking30:36 Building an Organic Audience32:01 Converting Followers into Customers34:50 Exploring Growth Hacks on LinkedIn36:14 Leveraging LinkedIn Video Content39:04 Navigating Links in Posts40:55 Insights on LinkedIn NewslettersLinks Mentionedhttps://x.com/tclarkmediahttps://www.linkedin.com/in/tclarkmedia/https://www.bluecast.ai/https://www.compoundcontentstudio.com/

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.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 The Genesis of The Pour Over02:52 Growth and Scaling Challenges06:10 Building a Subscriber Base08:51 Content Quality and Reader Engagement12:13 The Future of Newsletters and Podcasts15:07 Team Dynamics and Content Creation17:56 Advertising Strategies and Monetization26:55 Rebuilding Advertiser Relationships32:45 The Importance of Ad Copy35:08 Growth Strategies and Paid Advertising41:25 Referral Strategies for Subscriber Growth46:36 Securing Sponsorships and AdvertisersLinks MentionedThepourover.org

Get super-early bird pricing and an extra $100 off Newsletter Marketing Summit:NewsletterMarketingSummit.comUse code BFCM24 for the extra $100 off any ticket. This code expires on 12/2 at midnight EST.In this podcast, Matt and Ahrif discuss GrowLetter's first-ever conference, Newsletter Marketing Summit.Speakers include: Alex LeibermanSam ParrJames AltucherBrian MorrisseyJenny RothenbergRyan HashemiYossi J LeviChenell BasilioRyan Heafy Brad WolvertonTim HuelskampJay ClouseNeville MedhoraMatt McGarryAnd many moreGot questions about the event? Want to learn about sponsorship options? Contact: ahrif@growletter.co

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.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00The Journey Begins: From Beta to Launch02:58Identifying the Market Gap: The Gist's Unique Proposition06:02Building the Brand: Mission and Values08:47Growing the Audience: Strategies and Early Successes12:10Scaling Up: From Local to National15:01Navigating Growth: Lessons Learned and Key Metrics17:54Creative Marketing: Guerrilla Tactics and Launch Events20:54The Importance of Mission-Driven Growth24:02Partnerships and Collaborations: Expanding Reach27:02Self-List Cleaning and Giveaway Strategy35:01Expansion and New Ventures37:32The Birth of Within: A Personal Development Platform41:08Understanding and Preventing Burnout50:43Growth Strategy for Coaching BusinessLinks MentionedJoin Roslyn's newsletter, Within

Katy Huff, the cofounder of MadRev, shares insights on how to sell newsletter sponsorships, audience understanding, advertiser expectations, sponsorship strategies, pricing, contract renewal, working with different brands, and more.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00Introduction to Mad Rev and Sales Background03:12Fundamentals of Selling Newsletter Sponsorships05:56Understanding Advertiser Expectations09:09Identifying Potential Advertisers12:02Strategies for Securing Your First Sponsor14:53Pricing Your First Ads17:46Renewals and Long-Term Relationships with Advertisers21:03Working with Larger Brands24:05Final Thoughts and RecommendationsLinks Mentionedhttps://www.madrev.co/matt@newsletteroperator.com

Apply for GrowLetter to sell your ads here >>Episode Description:Matt and Ryan discuss the launch of the GrowLetter Ad Network, challenges faced by newsletter publishers in securing sponsorships and the changing landscape of ad rates, effective ad placement strategies, the importance of audience engagement, and the need for newsletters to be part of a broader business strategy and more.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Launching the Grow Letter Ad Network09:04 Challenges in Newsletter Monetization16:42 Optimizing Ad Placements and Strategies29:01 Building a Sustainable Advertising Business33:17 Newsletters as a Strategic Medium

Matt and Ryan share various newsletter business ideas and how to monetize through affiliate marketing, job boards, community engagement, and more.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction to Newsletter Ideas02:56 Global Talent and Remote Job Opportunities05:47 Building a Marketing Newsletter for Overseas Marketers09:04 Platform-Based Newsletters and Monetization Strategies11:56 Creating Unofficial Sports Team Newsletters14:48 Local Real Estate Investing Newsletters

Try Sponsy for free: https://getsponsy.com/MattAlex Pattis is the co-founder of the Deal Sheet and Last Money In Media. In this episode we break down how in just 14 months, Alex Pattis grew his newsletter Last Money In to over 41,000 subscribers and $200k/year in ad revenue and his paid newsletter Deal Sheet to $500K ARR in seven months.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Starting with a Newsletter10:02 Monetizing with Long-Term Sponsorships21:11 The Opportunity of Deal Sheet27:22 Strategies for Audience Growth38:32 Doubling Down on LinkedIn43:02 Creating Unique and Educational Content45:00 Final Thoughts and AdviceLinks Mentionedlastmoneyin.co

Join Write, Grow, Sell: WriteGrowSell.comSummaryIn this podcast episode, Matt McGarry discusses various strategies for growing newsletters, including the importance of webinars, effective marketing techniques, and the balance between running a course and an agency. He shares insights on SEO, content marketing, and the role of giveaways in subscriber acquisition. The conversation also touches on the challenges of newsletter publishing schedules and the potential of AI tools in content creation. Overall, the episode provides valuable tips for anyone looking to enhance their newsletter growth and marketing efforts.Chapters00:00 Introduction and Podcast Updates03:00 Webinar Success and Marketing Strategies05:54 Course Business Insights and Comparisons08:49 SEO and Content Marketing Strategies12:12 Giveaways and Subscriber Acquisition Techniques15:05 Local Newsletter Growth Strategies18:00 Mailbag Questions and Newsletter Publishing Schedules20:52 Ad Angles for Local Newsletters23:45 AI Tools for Content Creation27:10 Closing Thoughts and Future Plans

Matt and Ryan cover cold email strategies, new ad placements, the value of niche B2B media, owned audience, and recent acquisitions in the media industry. Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduction and Upcoming Meetup02:00 Email Deliverability and Cold Email Strategies08:19 Deliverability Concerns and Best Practices18:04 New Ad Placements and Lead Generation Opportunities22:48 Acquisitions in the Media Industry34:14 Financial Publishing and Recent ResignationLinks Mentionedmatt@newsletteroperator.com

Matt and Ryan cover the benefits of SEO-minded newsletter strategies and the potential of partnering with influencers to start profitable newsletters.Chapters00:00 Introduction and Discussion 06:21 Discussion about Books and Content Consumption19:19 SEO-Minded Strategies for Newsletter Success27:27 Partnering with Influencers to Start Profitable Newsletters37:06 The Value of Newsletters and Prioritizing EducationWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Matt and Ryan talk about the growth and success of media companies using negative CAC. AI in advertising, creative marketing strategies, tools, and more.Timestamps 00:00 Introduction and Plans for the Podcast02:53 Building a Media Company and Selling Something Else18:14 Example: Freight Waves and Sonar24:47 Example: ClickFunnels33:57 The Motley Fool: Building a Media Empire and Expanding into Asset Management and Venture Capital39:28 MeatEater: Leveraging Media and Acquisitions in the Outdoor Industry43:17 Cody Sanchez: From Media and Education to Holding Companies and Investments46:39 Rezzi Brands: Scaling Trade Services Franchise BusinessWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Charlie Hoehn is a three-time New York Times bestselling editor and five-time author. He has worked with Tim Ferriss, Ramit Sethi, Codie Sanchez, Tucker Max, David Goggins, and many others.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Introduced through podcast, impactful book, recession-proof advice.04:53 Initiated projects, and earned full-time employment success.06:59 A proactive mindset leads to more opportunities.11:15 Help businesses by addressing their key concerns.13:51 Busy people dislike long videos; need efficiency.18:59 Tim Ferriss leads workshops and gets direct feedback.22:08 Expand ideas, stories, and transformation in the book.24:12 Simon Siddig said: Tell stories with points.28:56 Books are about long-term commitment and impact.30:42 Book sales don't compare to equity earnings.35:51 People interested in writing books should focus.39:09 Target reader, build a personalized distribution list.40:49 Focus on prescriptive nonfiction for business owners.46:04 Ghostwriter disrupted author interviews, structure, and chapter content.49:15 Authors recommend conversational writing for more engaging content.Links Mentionedcharliehoehn.com

Matt and Ryan talk about effective strategies, formats for newsletter content, the importance of writing a marketing email, and many moreWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Lead with valuable content, tie to sale.05:27 Emphasize specific, actionable value in newsletters.08:53 Excited about new influencers and marketing strategies.11:34 Writing effective newsletters require careful strategy.13:33 Reduce excessive newsletter content and external links.18:57 Webinars, marketing emails, social posts, newsletters.20:07 Front-load marketing, send more emails. Missed opportunities.22:47 Testing email sequences for launches; effective content.26:43 Biohacking and focused marketing for future reports.29:18 Test different angles, focusing on specific angles.32:31 Using Quora for ad copy and success.39:10 Sam's trends team provided unique, affordable market insights.41:02 Attracted crowd, learning experience, successful business ventures.43:58 Steps to grow podcast: review, subscribe, screenshot.

Matt and Ryan talk about the takeaways from the newsletter conference, the B2B industry, the pros and cons of ads or promotions in newsletters, newsletter ideas, and many more.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 B2B newsletters are confident moneymaking plays.04:44 Creating podcasts, newsletters, and social media content drives business. Monetizing as a media company with ads/courses/memberships. B2B media is more lucrative than B2C. Sell directly to the audience for business growth.06:36 Media companies struggle with ads, and B2B creators thrive.10:17 Focusing on the specialized audience for high value.13:03 Workweek thesis: Identify niche industries for influence.17:34 Generate immediate revenue through targeted advertising strategies.19:52 Text blasts boost webinar registrations, and powerful marketing.25:12 Influencer marketing: finding underpriced attention is key.27:28 Smaller newsletters offer better advertising opportunities.31:37 Consider higher CPA for better long-term value.34:15 Many subscribers sign up for multiple newsletters.37:34 Prefer widget installation for faster revenue generation.40:33 Automated newsletters can be customized for relevance.44:45 Automated sequence customized for life events.46:02 Create a newsletter portfolio to build relationships.49:09 Leverage Facebook, content, and SEO for marketing.52:31 Publish podcast, send a screenshot for an invite. Live call.

Brad Wolverton is the editorial director at HubSpot Media and The Hustle (2.5M+ subscribers). Brad is also the creator of Newsletter Examples.Follow Brad on Twitter: https://twitter.com/bradwolvertonWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Proud to subscribe to newsletter examples on growth.06:06 Recruit through long-term relationships, adaptability, and resilience.09:03 Sam identified talent and facilitated her transition smoothly.11:07 Restructuring Hustle's operations aimed at professionalism.14:54 Consider audience, reach, and differentiation for success.18:34 Expand your network to find credible sources.22:46 New service for non-writing roles, cost-effective talent sourcing.24:01 Clearing the path for talented employees.28:45 Create habit-forming, repeatable content for email success.32:49 Magazines structure: front, feature, fun sections.35:55 HubSpot sought more diverse, experienced talent quickly.38:09 HubSpot's marketing funnel reaches customers effectively.41:37 HubSpot's strategy focuses on audience expansion.43:54 Leverage hustle for cross promotions with newsletters.49:37 Consider potential and be conservative in growth expectations.52:29 Marketing show needed deeper, actionable content.54:11 "Transition from introductions to tactical content."Links Mentionedhttps://newsletterexamples.co/https://twitter.com/bradwolverton

John Newtson is the founder of Financial Marketing Summit, a marketing conference for financial publishers, trading educators, and media brands. Connect with John on LinkedIn: linkedin.com/in/johnnewtsonWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Financial industry's pre-digital growth and transition.03:14 Early e-letter advertising was profitable and impactful.07:38 Product sales indicate customer interest and profitability.10:23 Front end: introductory, back end: advanced products.14:31 Financial media sources improve niche media buying.18:52 Online marketing involves funnels, email series, and promos.20:15 Diversify products for multiple sales and profits.24:43 Porter Stansbury launched with a unique Amazon promo.28:38 Understanding markets, focusing on big trends.29:41 Mainstream story grabs attention but not wallets.33:24 Copywriter promotes cannabis investment and attracts celebrity investors.38:49 Affiliates offer new revenue through customer reactivation.39:50 Buying sprees, competition for talent, sharing promos.45:35 People falling due to shared worldview in promotions.46:45 Buffet has strong philosophies on market changes.50:03 Publisher drives ideas and makes qualitative decisions.53:56 Publisher's $10 million promo led to less profit.56:40 Search Matt McGarry on YouTube for an invite.Links Mentionedhttps://financialmarketingsummit.com/matt@newsletteroperator.com

-> Learn more about Newsletter Operator All Access here.-> Use code "GROWLETTER" to get $100 off your ticket to The Newsletter Conference. About this EpisodeRyan Sager and Jesse Watkins are the founders of Who Sponsors Stuff, an advertising intelligence tool that tracks 500+ newsletters, and the hosts of The Newsletter Conference, which will take place on May 3rd.Episode Topics & Timestamps00:00 Matt McGarry discusses newsletter advertising trends in 2024.04:31 Summary: Discussion on sponsors tracking and email advertising.06:52 Newsletter advertising remains consistent with 10-20 daily.12:11 Pricing and value in sponsorship programs.14:03 Increase multiples for highly engaged audiences.18:23 Ad networks attempt unique, bespoke ad offerings.20:15 Performance standards, payment for access, risk assumption.25:32 "Customize ad pitch, avoid commoditization, discussion."26:17 Understanding brand advertising and messaging for sales.31:15 Relationship with audience determines product fit.33:53 Build rapport before selling dedicated content.37:33 Discount bundling increases sales and requires careful renewal.42:01 Emphasis on sponsorship, data products, and expansion.45:29 Events in NYC are expensive and need an audience.46:31 Traditional publishers struggle with newsletter ad integration.50:33 Request a screenshot of the podcast and email for an invite.Links Mentionedhttps://allaccess.newsletteroperator.com/https://thenewsletterconference.com/https://www.whosponsorsstuff.com/matt@newsletteroperator.com

Matt and Ryan talk about behind-the-scenes and early-stage plans for building a newsletter in public, how to grow your agency through a newsletter, and more.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Building newsletter in public, early stages revealed.05:20 Premium subscription launched early, aiming for revenue.07:17 Experimenting with batching and weekly delivery. Consider monetizing from day one.11:48 Challenges with paid marketing and growing channels.13:36 Outline for landing page: Headline, letter, membership breakdown.18:40 Public promotion key for organic media company growth.19:32 Using faceless videos for better content discovery.22:28 The coaching program requires daily short video filming.25:52 LinkedIn expert advice: focus on broad content.28:37 Confident about branding, content, and organic growth.34:08 System and constraints shape consistent and habitual reading.36:29 Local newsletters with smart brevity style. Numbered, easy to follow on mobile.37:57 Alex Garcia's newsletters on influencer partnerships shine.42:10 Visualizing simple things, and updating data for newsletters.

Matt and Ryan talk about how to sell out a cohort-based course, how to use newsletters to get and keep clients for service-based agencies, and much more.Support our sponsors: Refind Ads helps you grow your newsletter on auto-pilotGet a $25 ad credit when you spend $100 or more.--Sponsy streamlines sponsorship operations and reporting so you can save time and keep sponsors happy. Try Sponsy for free or book a demo here. --Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 Refind ads: easy setup, effective paid acquisition.06:04 Sales exceeded expectations, and several units sold out.09:02 Emphasize long-form sales pages in product promotion.10:32 Two similar announcement broadcasts successfully sold the course.14:13 Create an email list, and send targeted course promotions.19:05 Utilize PS in email for important messages.21:25 Easier to get testimonials for future courses.23:26 Incentivized survey with $100 prize and bonus.27:28 Service business provides more freedom and value.30:22 Promote digital products, showcase expertise, and upsell.33:34 Targeted newsletter ads create high conversion rates.37:57 Create niche Twitter ads and share insights. 42:31 Leave a review on Apple/Spotify and subscribe with an email proof.43:43 Podcast host seeks feedback to reach a wider audience.

Anik Singal is an entrepreneur, author, and expert in scaling education businesses.Check out Anik's books and podcasts here: AnikSingal.comWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Timestamps 00:00 Choose digital product and sales method carefully.06:50 Leverage small audiences for higher priced offers.10:21 Forcing offers without audience interest always fails.12:12 Answering questions, creating an FAQ, monetizing support.14:48 Compliance market infatuates despite initial disinterest.17:39 Streamlined installation process, captured and sold.23:17 Low ticket pricing strategy for ad spend.26:32 Quickly create low-ticket products using templates & AI.30:23 Funnel engagement, low initial webinar attendance.32:48 Extend funnel, increase sales by 30%.35:50 Integration: Sendlane, Drip, stealth seminar, zapier.40:47 Busy schedule, overlapping webinars, managing affiliates.44:19 Presenting involves tech, passion, and valuable skills.47:35 FTC investigation felt worse than a colonoscopy.50:25 Learning, writing, and turning challenges into success.51:39 New suite, certification, compliance marketing, book, audit.54:43 Testimonial usage, disclosure, and court impact.

Eric Siu is the CEO of Single Grain and host of two successful podcasts: Marketing School and Leveling Up.  These podcasts receive over 1 million downloads per month.  Follow Eric on Twitter: @ericosiuWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on TwitterEpisode Topics & Timestamps00:00 Early podcasting success fueled by validation and education.05:59 Content strategy should align with expertise and budget.08:48 Daily marketing podcast successful with 2700 episodes.11:28 Ads to the newsletter to value, not ads.14:23 Starting an agency is challenging but rewarding.16:31 Start side hustle, secure financial cushion first.21:06 Strategic hiring in the US, referral recruiting.24:46 Productized agencies offer clear and predictable services.26:28 Maintaining quality and demand for creators is important.31:29 Webinar on real-life AI use cases.35:53 Monthly marketing content with unlimited options available.36:45 Finding sponsors for your newsletter through titles.42:18 Financial subscriptions, conferences, and high returns.44:48 Powerful email sales strategy: ask for a reply.46:25 Creating communities for learning and networking.50:00 Stay focused, avoid distractions and reach success.Links MentionedLeveling Up NewsletterSingle Grain  

Matt Paulson is the founder and CEO of MarketBeat. Matt's media company and newsletter has over 4.3M subscribers and is on pace to do $40M in revenue this year. Follow Matt Paulson on Twitter: @MattPaulsonSDWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.Episode Topics & Timestamps00:00 About MarketBeat and Matt's media company05:14 Ad spend across Google, Bing, Facebook, and other channels 09:09 Working with agencies  11:46 Managing advertising through agencies, offers, and automation.13:42 Hot stock trends drive high newsletter engagement.17:28 Two big companies and smaller affiliates20:56 The Financial publishing industry and the CPA model.25:06 Investor relations, financial newsletters, CPA deals.29:16 Dynamic offer rotation maximizes email campaign performance.32:42 Multi-channel marketing maximizes message delivery effectiveness.36:17 Email success depends on optimizing for sales.36:59 Rising newsletter ads face potential sustainability issues.40:44 Consider audience demographics, interests, then find affiliate program.45:53 Marketbeat's plans47:23 Pioneering data-driven financial content creation 50:21 Where to find Matt onlineLinks MentionedMarketBeat.comTwitter.com/MattPaulsonSD

Matt and Ryan talk about 5 newsletter business ideas. Plus, how to grow and monetize them. Episode topics & Timestamps00:00 Newsletter targeting Fortune 500 executives for news.04:34 Create hyper relevant content for niche market.06:57 High CPMs for well-defined executive audience.12:53 Research-intensive content, provide templates, charge for value.16:14 Curated finance memes drive engagement on Instagram.19:19 Charter newsletter uses visuals and witty copy.22:42 AI writing tool boosts creativity for writers.23:34 Weekly summary of design and pricing trends.27:23 Newsletter format: short, snippets, automate, historical lessons.32:07 Sponsors and newsletter offer monetization challenges.35:42 Podcast reviews books about influential people. Crazy network.37:39 Building email list crucial for long-term success.40:39 Opt for positive, non-crime local news.43:14 Local writing can lead to access and recognition.46:26 Increased interest in local business advertising benefits.49:33 Seeking feedback and updates on shared ideas.Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Adam Ryan is the co-founder and CEO of WorkWeek, a B2B media company with 10+ newsletter publications and communities across various industries like healthcare, marketing, sales, HR, e-commerce, and fintech. Episode topics & Timestamps00:00 How WorkWeek started05:04 Audience indicators and your ideal customer profile (ICP)07:32 Slow, strategic growth trumps rushing into big projects.10:19 Different business growth approaches have varying scalability and repeatability. Lifestyle businesses may benefit from an agency model, but for larger, scalable ventures, ongoing growth and compounding the business are crucial.14:40 Approach to product development, growth metrics17:32 Thoughts on newsletter recommendation networks22:13 The email inbox is more sensitive 24:46 Paid ads 26:47 Maximizing existing audience potential 31:17 Acquiring newsletter subscribers and the potential trade-offs involved.35:05 Focus on quality over quantity for newsletter subscribers. 36:34 Organic growth and subscriber engagement 40:14 Traditional media43:35 Higher ad revenue, lower churn, better LTV47:45 Prioritize audience, seek feedback, and consider time constraints.50:24 How B2B lead generation worksLinks Mentioned WorkWeek.comWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator.comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Matt and Ryan talk about newsletter monetization, how to create and sell a front-end offer, webinars, polls,  courses, and more.  Episode topics & Timestamps00:00 Aligning monetization strategies enables sustainable and scalable growth.06:21 Creating post subscription funnel to boost sales.09:03 Curate and repurpose newsletter content for subscribers.11:22 Identify problems, consumer needs, and create products.16:26 Promoting course through webinars and email marketing.18:50 Live course allows immediate Q&A interaction.22:31 Testing successful outreach to high-ticket service businesses.25:24 Share audience poll in outbound strategy for agencies.28:28 Postponing deliverability discussion, Google policy updates, future episode.Links MentionedNewsletter Growth SystemWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator(dot)comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Wouter Teunissen is co-founder of OpenRates -- A tool that helps you find and convert newsletter sponsorships in your niche.  Previously Wouter was the first salesperson at Milk Road. Episode topics & Timestamps(13:20) Cornerstone Resources for Marketing and Copywriting(13:40) Importance of Authority in Newsletter Niche(14:00) Creating a Personal Toolkit for Sales Success(32:40) Automating the Sales Cycle with Databases(32:52) Identifying the Right Contacts for Sponsorship Outreach(40:40) Incentivizing Audiences with Surveys(41:00) The Pillars of Effective Marketing and Sales Messages(41:20) How to Follow Wouter Teunissen's Work(41:34) How to Support the Newsletter Operator PodcastLinks Mentioned https://www.openrates.co/Want more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator(dot)comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Tim Huelscamp is the co-founder & CEO of 1440 Media. In this podcast, Tim shares his strategies for scaling and monetizing newsletters, how 1440 reached over 3 million subscribers by delivering comprehensive, unbiased news, and much more. Episode topics & Timestamps(00:15) Guest Introduction (00:42) 1440 in the media landscape, aimed at busy professionals desiring a comprehensive yet unbiased news source. (01:49) 1440's foundation story, starting from frustration with existing news media, testing minimum viable product concepts, and the emphasis on high open rates and organic growth as evidence of product-market fit.(04:33) 1440's Audience & Demographics(06:12) Retention and Engagement (07:28) Creative Strategy & Growth Levers, discussion on  the significance of high-quality, compelling creative work in driving subscriber growth(20:25) Monetization Strategies(39:42) Potential for Newsletter Market Saturation and the necessity for delivering high-quality content as the key differentiator for long-term success.(44:41) Future of 1440(52:51) Tim's offer to assist rising newsletter creators by way of connecting and reflecting on the supportive nature of the newsletter community.Links Mentioned:Join1440.comReach out to ​Tim directly: tim@​join1440.comWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator(dot)comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.

Matt and Ryan interview Brett Perlmutter, co-founder of BulletPitch, a startup newsletter turned media company. They discuss the company's origin, mission, and audience engagement metrics. Brett shares growth strategies and revenue models.Episode topics & Timestamps(00:25) Introduction and brief overview of BulletPitch, motivation behind starting BulletPitch (02:25) the rapid growth of BulletPitch and the audience size (05:25) how BulletPitch measures audience engagement through polls and investor introductions (08:49) the ratio of growth from Twitter ads, organic sharing, referrals, and word of mouth (12:18) Discussion on the strategy of Twitter ads and what makes a good ad(23:15) The Business model of Bulletpitch (27:00) Launching BulletPitch Plus(35:48) Insights on newsletter saturation (41:49) Monetization challenges faced by newsletters (45:09) Brett shares his experience with hosting events and the value of in-person interactions for newsletter subscribersLinks mentioned:https://www.bulletpitch.com/https://twitter.com/BrettPerlmutterWant more content like this?Join Newsletter Operator for more strategies on how to grow and monetize your newsletter here: NewsletterOperator(dot)comWork with Ryan's agency Tailwind Work with Matt's agency GrowLetterFollow Matt McGarry @JMatthewMcGarry and Ryan Carr @ryan_boat on Twitter.