This week Francis Zierer speaks with Lindsey Stanberry, creator of The Purse, a newsletter focused on money, motherhood, work, and relationships. Lindsay shares her journey from working in corporate media to becoming an independent creator/entrepreneur.The Purse: https://thepurse.substack.com/00:00 Introducing Lindsey and The Purse 01:25 Transitioning from Corporate to Independent Creation 06:16 Developing a Blog into a Sustainable Brand 09:30 The Biggest Detriment to Journalists in Media 14:26 Defining Identity: Creator, Journalist, or Entrepreneur? 19:44 The Value of Collaboration and Partnership in Entrepreneurship 24:43 Choosing Your Niche for a Content Franchise 30:54 Growing an Organic Newsletter Audience 32:14 The Challenge of Paid Subscriptions 35:22 Fostering a Community Through Events 38:18 Creator's Concern of Financial Sustainability 42:24 The Evolution of the Newsletter Format 45:05 The Value of Transparency and Trust as a Creator 47:08 The Value of Quality Writing Amongst Abundant Free Content 54:29 Take Yourself Seriously

Daisy Alioto, the CEO and editor of Dirt Media, shares her insights on running a modern media company influenced by streetwear branding. She discusses the evolution of Dirt Media and emphasizes treating subscribers as collectors. Daisy explores the importance of understanding your audience and the value of collaboration for growth. She also reflects on the contemporary media landscape and the responsibilities of creators in contributing thoughtfully to the internet. Expect a unique blend of pop culture, creativity, and practical business strategies!

Michael Kauffman, founder of the Catskill Crew, dives into the world of community-led newsletters and sustainable revenue models. He discusses the importance of audience engagement and building local relationships. Kauffman emphasizes the emotional impact of branding, drawing parallels to nostalgia and comfort. He shares strategies for monetization while maintaining authenticity in the creator economy. The conversation highlights the uphill battle local newsletters face, but also the vast potential for growth and community collaboration.

John Hu, known online as Jayhoovy, is the founder of Stan, a comprehensive monetization tool for creators. He dives into the challenges creators face in today’s economy and the importance of personal branding for success. John emphasizes the power of consistency in content creation and the need for effective systems thinking. He discusses the potential of creator-led digital products and what it means to build in public, arguing that honesty fosters competitive advantage. Plus, he inspires with stories of perseverance and self-belief in the entrepreneurial journey.

Adam Ryan, CEO and co-founder of Workweek, shares his extensive experience in the newsletter industry. He discusses the delicate balance between creativity and sales, revealing key strategies for audience growth. Adam emphasizes consistency as crucial for content creators and reflects on how his early career shaped his marketing acumen. He explores the transformation of newsletters from mere accessories to vital marketing tools, highlighting the importance of authenticity and values in driving business growth.

Joining the discussion is Lex Roman, a freelance growth marketer and creative entrepreneur known for his newsletters, Journalists Pay Themselves and Revenue Rulebreaker. Lex delves into innovative monetization strategies, highlighting how to thrive with a small audience. He examines the significance of niche communities and the evolving role of newsletters for income. Lex also tackles subscription fatigue and the understated yet crucial business acumen of journalists, revealing fresh insights on ethical practices and community engagement in the creator economy.

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 Bottleneck01:09 Building a Strong Audience Relationship03:07 Lessons Learnt from the Startup World07:18 The Decision to Start a Newsletter13:31 The Structure of the Newsletter17:00 Experimenting with Different Writing Styles20:08 How the Newsletter Generates $30k a Month26:00 Building an Audience from Scratch to 28k Subscribers32:30 Are Creators Also Founders?37:27 Building a Team as a Founder40:57 The Many Failed Experiments that Led to The Bottleneck44:27 Building a High Value Community49:52 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