Leigh Stein, a six-time author and cultural critic, shares her insights on navigating the modern writing landscape. She argues that now is the best time to be a writer, emphasizing the need to view art as a product. Stein discusses the impact of platforms like TikTok and BookTok on the literary world and advocates for destroying the stigma around self-publishing. She also delves into creating shareable content, the evolving dynamics of the creator economy, and offers valuable advice for aspiring writers.

This time, Eric Silver joins the conversation. Eric is a seasoned podcaster and head of development at Multitude, a prominent podcast studio. They delve into podcasting techniques, emphasizing audio storytelling over video. Eric shares insights on crafting a unique interview style and the rise of Actual Play podcasts. The discussion also highlights the ethical considerations in creator businesses and the importance of fresh perspectives in interviews. Listeners gain valuable tips on what makes a great podcast guest and the future of independent media.

This week Francis is joined by Matt Brown of Extra Points. With a laser focus on writing high quality content, Matt is an independent sports journalist covering the world of college sports in America. Extra Points: https://www.extrapointsmb.com 00:00:00 Introducing Matt Brown and Extra Points 00:01:47 The focus on producing quality content 00:05:26 The unique story of acquisition and reacquisition 00:13:11 Striving to make the internet a better place 00:19:36 Balancing creativity and business in the creator economy 00:22:53 The values and integrity of independent journalism 00:26:27 Vox Media: The bootcamp for independent journalists 00:35:28 Understanding your community 00:42:29 Providing value with high-ticket and low-ticket offers 00:55:41 Analytics are not money 00:59:59 Bridging the gap between communities through sport 01:04:09 The decentralization of media

This week Francis is joined by essayist and culture critic, Alicia Kennedy. Alicia is primarily a food writer, however also has many refined takes on writing, the algorithm, and the attention economy.Alicia's Newsletter: https://www.aliciakennedy.news/00:00:00 Introducing Alicia Kennedy00:01:38 Rejecting the idea of the creator00:07:06 Declining media literacy in the digital age00:12:36 The fragmentation of public intellectualism00:17:09 Attaching value to greatest achievements00:19:32 The creator economy tradeoff of freedom and instability00:29:33 The need for publications that challenge food writing norms00:35:08 The blurred line between influencers and creators00:40:13 Building a like-minded diverse community00:43:58 The key to consistent organic growth00:47:10 The need for a more horizontal media ecosystem00:52:32 Navigating platforms with limited audience engagement control00:57:51 Experience of writing a book vs newsletters

This week Francis is joined by Kofie Yeboah a versatile creator in the sports media landscape. Kofie does it all, social media, long-form, short-form, podcasts, research and writing. He's here to tell us how he does it all.Kofie's YouTube: https://www.youtube.com/@KofieWhy00:00 Introducing Kofie Yeboah01:25 Kofie's early introduction to sports05:35 The evolution from long-form to short-form10:21 TikTok's endless opportunities and constant insecurity14:37 Balancing roles as a content creator and producer19:43 Successful strategies for repurposing content26:56 The best and the worst of social platforms29:57 Fostering a positive and engaged community32:23 Revenue reinvestment strategies43:24 Balancing a full-time job with content creation46:55 Kofie's relationship with different sports leagues48:33 The path to 100k subscribers

Jenna Stoeber, a video essayist and content creator with a master's in media, discusses her unique approach to creating engaging content. She reveals the secrets behind navigating YouTube’s algorithm and the importance of authenticity over optimization. Jenna shares her insights on balancing diverse revenue streams and maintaining creativity amidst pressures of social media. Additionally, she dives into the art of scripting video essays, emphasizing viewer engagement while pushing the boundaries of educational media.

This week, Francis is joined by Henry Winslow, founder and writer of Tricycle Day, a newsletter focused on psychedelics research, policy, and business. Francis interviewed Henry exactly one year ago, and this conversation is centred around Henry's growth over the past year. Tricycle Day Newsletter: https://www.tricycleday.com Tricycle Day Instagram: https://www.instagram.com/tricycleday 00:00 Sustaining a creator-led business following rapid growth 06:27 The key to growing your first 1000 subscribers 09:23 Understanding your audience and utilizing data 12:44 Hiring an successful team as a creator 16:47 Scaling to a $250k business in year two 18:53 The benefits of advertising to a niche audience 23:27 The struggles of operating in a controversial space 28:03 Building an audience around trust 35:21 Expanding your business beyond the newsletter 38:09 Community is a buzzword, but not this time 41:42 Goals for 2025

Matt McGarry, known as the Newsletter Guy, is the mastermind behind Growletter, an agency that helps creators build their subscriber lists. In this chat, he unveils the challenges of monetizing newsletter-only businesses and the importance of valuable content. Discover why newsletters are more of a strategic communication tool than a standalone business model. Matt also shares insights on effective subscriber acquisition strategies, the newsletter landscape's saturation, and emerging trends in B2B content. A must-listen for aspiring creators!

Lindsey Stanberry, creator of The Purse newsletter, discusses her inspiring transition from corporate media to entrepreneurship. She highlights the challenges of defining her identity as a creator and the significance of targeting a niche audience. Lindsey emphasizes the importance of quality content, community engagement, and collaboration in building a sustainable brand. She shares her insights on navigating subscription fatigue and the value of transparency in fostering trust with her audience. Her journey showcases the evolving landscape of journalism and the entrepreneurial skills needed to thrive.

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!