This week Francis is joined by Michael Kauffman to discusses his journey building a local newsletter business, Catskill Crew. He shares insights on audience engagement, growth strategies, and the importance of branding in the creator economy.

Catskill Crew: https://catskillcrew.com

Newsletter Club: https://thenewsletter.club

00:00 Building a Community-Led Newsletter

05:57 Local Relationships are Crucial for Newsletter Success

12:29 Building Businesses Around a Local Newsletter

14:28 Why You Must Begin With Organic Growth

17:50 The Importance of Branding and Identity

24:41 The Internal Desire to Create

28:55 Building a Sustainable and Authentic Revenue Model

38:43 The Local Holding Company Model

41:50 Revenue Breakdown and Business Structure

43:12 The Importance of Community Engagement

47:12 Financial Realities of Starting a Newsletter

50:48 The Newsletter Club: A Community for Creators

53:41 The Future of Local Journalism

This week Francis is joined by content creator and entrepreneur John Hu, also known as Jayhoovy. John is the founder of Stan, an all-in-one monetization tool for creators. He shares insights on the challenges creators face in the business landscape and how his platform, Stan, aims to empower them.

Check out Stan: https://www.stan.store/

John's YouTube: https://www.youtube.com/@jayhoovy

00:00 Introducing John and his company, Stan

01:24 Building an Audience and Personal Brand

05:05 The Artist to Entrepreneur Spectrum

07:45 Allocating Time as a Content Creator vs CEO at Scale

11:18 Celebrating Creator Success Stories

14:40 The Importance of Consistency in Content Creation

17:49 All Humans Will Be In the Creator Economy

21:30 The Value of Systems Thinking as a Creator

25:33 Scaling a Team and Hiring a Professional Memer

29:00 The Opportunities in Creator Led Digital Products

32:07 Attention Economy: The Limited Resource

33:56 Navigating Different Social Platforms for Success

36:25 Is Building in Public a PsyOp?

This episode is with one of the best business minds in the newsletter world, Adam Ryan of workweek.com

Workweek: https://workweek.com

Adam: https://x.com/adamry_n

00:00 Introducing Adam Ryan and Workweek

03:44 The Balance of Creativity and Sales

06:21 Key Levers for Audience Growth

08:53 Content Trends and Audience Engagement

10:03 Current Projects and Initiatives at Workweek

12:39 The Difficulties of Balancing Creativity and Entrepreneurship

15:59 The Importance of Consistency as a Creator

20:40 From Campus Rep to Brand Builder

27:59 The Evolution and Future of Newsletters

38:04 Advising the Next Generation of Newsletters

44:59 Vision for the Future of Workweek

This week Francis is joined by creative entrepreneur, Lex Roman. Lex is a freelance growth marketer with two newsletters, Journalists Pay Themselves and Revenue Rulebreaker.

Journalists Pay Themselves: https://journalistspaythemselves.com/

Lex's Website: https://lexroman.com/

00:00 The Multi-Hyphenate Journey of Lex Roman

04:00 Defining Creators and Creative Entrepreneurs

10:53 Monetization Strategies for Creators

15:43 The Boutique Creator Model

19:00 Revenue Streams and Success in the Creator Economy

23:33 The Role of Journalists in the Creator Economy

26:22 Virtual Events and Controversial Takes

33:27 Understanding Subscription Fatigue

40:44 The Overvaluation of Social Media for Growth

45:19 The Future of Internet Columnists

This week Francis is joined by Alex Dobrenko, a comedian and writer of the newsletter Both Are True.

Both Are True: https://botharetrue.substack.com

Alex's Twitter/X: https://x.com/dobrenkz

00:00 Intro

01:23 The Journey to Comedy and Writing

08:20 Writing Style and Honesty

15:02 The Role of Improv Comedy in Creativity

22:07 The Growth of an Audience

30:26 Professionalization of Content Creation and "Selling Out"

38:57 Whoa: Exploring Deeper Conversations through Interviews

45:37 Navigating the Solitary Nature of Creation

49:15 The Evolution of Social Media Engagement

This week Francis is joined by Penn Weinberger, founder and head of the agency Bad Behavior. Bad Behavior works with creators to produce original short-form shows for brands; they’ve worked with clients like Lyft, Columbia Records, Cash App, and Stanley.

Bad Behavior: https://www.bad-behavior.com/

00:00 Introducing Penn and Bad Behavior

01:42 Working with Creators vs. Influencers

05:00 The Impact of Viral Marketing

07:14 Empowering Creators

09:35 Upsetting the Traditional Advertising Model

13:42 Starting and Then Diversifying the Agency

17:12 The Blur Between Creator and Celebrity

22:22 The Revenue

26:07 The Increase in Management Amongst Creators

30:06 Rules for Building a Creator-Led Show

32:47 Finding Brands as a Creator

36:35 Red Flags for Brands and Creators

41:06 Unpredictable Virality

This week Francis is joined by Rameel Sheikh, founder and writer of The Bottleneck which, in his words, is the only weekly newsletter offering stories, frameworks, and tactics to sharpen how you execute.

thebottleneck.io

00:00 Introducing Rameel Sheikh and The Bottleneck

01:09 Building a Strong Audience Relationship

03:07 Lessons Learnt from the Startup World

07:18 The Decision to Start a Newsletter

13:31 The Structure of the Newsletter

17:00 Experimenting with Different Writing Styles

20:08 How the Newsletter Generates $30k a Month

26:00 Building an Audience from Scratch to 28k Subscribers

32:30 Are Creators Also Founders?

37:27 Building a Team as a Founder

40:57 The Many Failed Experiments that Led to The Bottleneck

44:27 Building a High Value Community

49:52 Future Dreams or Goals of The Bottleneck

Today’s guest is Swapna Krishna, creator of Ad Astra, a YouTube channel and beehiiv newsletter about space. She’s a professional writer with over a decade of experience doing everything from journalism to content marketing to authoring a book.

She’s been all-in on Ad Astra, her first venture as an independent creator since the start of 2024.

00:00 Intro

01:20 The Journey of Writing and Publishing a Book

04:35 Transitioning to Video Content Creation

07:22 Developing Presentation Skills Through Podcasting

12:42 Defining the Creator and Journalist Identity

18:31 Swapna's Journey Through the Content Creation World

22:22 The Differences in Solo Creating and Working in a Team

30:25 All of Swapna's Projects 31:50 Production Process: From Idea to Execution

41:58 The Relationships with Swapna's Different Audiences

48:34 Space-X's Media Dominance

50:40 The Monetization

54:25 Defining Goals and Editorial Mandate

Today’s guest is Alex Emery, a creative director and content strategist who spent the first 8 years of his career at Sky Sports before leaving 2 years ago to work with creators. His first client was John Nellis, a YouTuber with 5,000 followers at the time — they’ve since increased that number to 1.74 million and counting, and Alex is working with John full-time.

00:00 Intro

01:10 Getting into the world of football content

04:43 Tripling the growth of Sky Sports YouTube channel

07:27 The partnership with John

13:52 Combining the business and creative mind

16:24 How the business operates

18:41 How big is the team?

20:05 Producing content from in-front the camera

24:49 Why John Nellis is the best to work with

29:50 Growing and reinvesting into the business

35:10 The importance of the title and thumbnail

37:34 The myth behind "retention editing”

40:46 How the channel is monetized

44:27 Why you should delete your old videos

46:09 How much money is the channel making?

48:23 The work/life balance of a content creator

51:54 The goal for the channel

55:52 YouTube vs TV

Today’s guest is Caitlin Dewey, creator if Links I Would Gchat You If We Were Friends, a newsletter she started nearly 11 years ago, when she was the social media reporter for the Washington Post. She wrote it for 2 years, taking a 4-year break before bringing it back in 2020; earlier this year, she decided to go all-in and make it her main gig.

We spoke about the particular challenges of being a creator-journalist, how to write an actually good links aggregation newsletter, and choosing to build a lifestyle business instead of a media empire.

00:00 Introducing Caitlin Dewey

03:27 The Origins of the Newsletter

06:16 Taking a Break and the Pressure of a Rebrand

13:36 Building a Community With Readers

17:53 Building a Good Salary From Subscriptions

19:49 The Definition of Creators vs. Journalists

27:42 Bring Back Comfortable Middle Class Lifestyles

32:59 Collaboration in the Newsletter Community

37:37 The Painful Art of Content Planning

43:21 Substack's Shift in Business Model

50:13 The Craft of an Aggregation Newsletter

53:19 Fake News Is Now Just News