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.

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Episode Topics & Timestamps

00:00 Introduction to Tyler Morin and Water Coolest

02:59 The Journey to Founding Water Coolest

06:03 Building an Audience: Strategies and Insights

09:01 Monetization and Transitioning to Full-Time

12:00 Early Sponsorships and Learning from Mistakes

14:58 Crafting an Irreverent Newsletter

17:59 The Evolution of Humor in Newsletters

22:48 Navigating Acquisitions: The Barstool Experience

30:11 The Changing Landscape of Ad Rates

34:41 Building a Newsletter at Barstool

39:46 The Return of The Water Coolest

42:50 Consulting: Helping Others Build Their Media Businesses

This episode is sponsored by Playbookz: Playbookz.co

Ted 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.

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Kendall 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.

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Get Justin's new book: SponsorMagnet.com

Justin Moore is a sponsorship coach and the author of Sponsor Magnet: How to Attract, Price, and Execute Your Dream Brand Partnerships

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Episode Topics & Timestamps

00:00 The Importance of Custom Pricing for Creators

09:16 Creating a Comprehensive Sponsorship Strategy

27:05 Attracting Brands: The STP Framework

28:32 Navigating the Complexities of Pricing Sponsorships

29:00 Understanding the ARC Framework for Collaborations

32:19 Pricing Strategies Based on Brand Goals

34:46 Creating Compelling Sponsorship Packages

39:04 Innovative Collaboration Examples

43:52 Crafting Effective Outreach Strategies

57:10 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.

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Episode Topics & Timestamps

00:00 Introduction to AdCrate and Growth Strategy

02:56 The Importance of Ad Creative in Paid Advertising

05:47 Navigating Media Platforms: Meta vs. TikTok

08:53 Static vs. Video Creatives: Balancing Production and Impact

11:49 Effective Static Ad Formats and Testing Strategies

15:09 Common Mistakes in Ad Creation and Copywriting Tips

17:55 Leveraging AI for Ad Copy and Customer Insights

20:47 Innovative Ad Formats: Memes and Interface Hacking

25:42 Understanding Hook Rates and Audience Engagement

28:10 Navigating Video Content Creation on a Budget

35:09 The Importance of Script Writing for Ads

40:50 Exploring Effective Video Lengths and Frameworks

43:40 Utilizing Motion Graphics for Enhanced Engagement

46:34 Iterating and Testing Ads for Success

Links Mentioned

https://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.

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Episode Topics & Timestamps

00:00 Holiday Reflections and New Beginnings

02:03 The Honey Scandal Explained

17:48 Trends for 2025: Buying and Selling Insights

27:33 The Substack Ecosystem and Creator Independence

31:27 AI-Assisted Workflows for Content Creators

33:22 The Shift from Vanity Metrics to Revenue Focus

34:20 Emerging Newsletter Ad Networks

39:00 The Rise of B2B Newsletters and Creators

41:24 Challenges of Premium Newsletters

44:43 The Creator-in-Residence Model

48:55 The Future of Overseas Recruiting Agencies

Links Mentioned

https://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.

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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. 

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Episode Topics & Timestamps

00:00 The Importance of Clear Value Proposition

03:13 Audience Growth Strategies on LinkedIn

06:04 Content Creation Fundamentals

08:58 Optimizing Content for Engagement

11:47 Leveraging Controversy in Content

14:57 The Power of Personal Stories in Content

23:58 Reflecting on Weekly Engagements

24:57 The Importance of Specificity in Content

25:51 Understanding Engagement on LinkedIn

27:44 Strategies for Boosting Engagement

29:38 The Risks of Engagement Hacking

30:36 Building an Organic Audience

32:01 Converting Followers into Customers

34:50 Exploring Growth Hacks on LinkedIn

36:14 Leveraging LinkedIn Video Content

39:04 Navigating Links in Posts

40:55 Insights on LinkedIn Newsletters

Links Mentioned

https://x.com/tclarkmedia

https://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.

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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