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

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 Dewey03:27 The Origins of the Newsletter06:16 Taking a Break and the Pressure of a Rebrand13:36 Building a Community With Readers17:53 Building a Good Salary From Subscriptions19:49 The Definition of Creators vs. Journalists27:42 Bring Back Comfortable Middle Class Lifestyles32:59 Collaboration in the Newsletter Community37:37 The Painful Art of Content Planning43:21 Substack's Shift in Business Model50:13 The Craft of an Aggregation Newsletter53:19 Fake News Is Now Just News

Tommy Clark, a B2B social media expert and founder of Compound Content Studio, began his content journey while studying nutrition. He shares how he inadvertently built a successful agency and reflects on the dynamics of team building. Discussions shift to the art of viral posts, emphasizing trendjacking and audience engagement. Clark also explores striking a balance between personal branding and business management, revealing strategies for creator-led monetization and the evolution of YouTube for trust-building and lead nurturing.