Tim Huelskamp, co-founder of 1440, shares insights from his journey in creating a successful newsletter with 4 million readers. He discusses the art of delivering concise news and the challenges of competing in a saturated market. The conversation explores the evolving landscape of advertising, the role of AI in media, and the importance of maintaining genuine relationships with readers. Huelskamp emphasizes fostering a positive workplace culture, which he believes translates to better product quality and customer satisfaction.

Renee DiResta, an academic and researcher at Georgetown, specializes in online abuse and disinformation. She shares her experiences with harassment while studying the 'Stop the Steal' movement. The conversation highlights the rising challenges of content moderation as political dynamics shift, especially with Trump back in the spotlight. DiResta warns of a chilling effect on research and the importance of transparency in combating misinformation. She also humorously reflects on what not to do when appearing on popular podcasts.

Jason Koebler, co-founder of 404 Media and former Vice Media tech head, shares his journey of launching a successful media company with just $4,000. He discusses the challenges of creating a sustainable model without relying on rich investors and emphasizes the importance of quality journalism. Koebler highlights the innovative strategies behind their subscriber-based funding and the impact of community-driven tech journalism. They also explore the dynamics of independent media and the need for diverse voices in tech reporting, bridging niche narratives with audience engagement.

Chris Balfe, Founder and CEO of Red Seat Ventures, is a powerhouse in online media, having previously collaborated with Glenn Beck. He discusses how prominent figures like Tucker Carlson and Megyn Kelly are reshaping the media landscape as they transition to digital platforms. Balfe dives into the dynamics of monetization for podcasts, challenges in brand advertising, and the significance of genuine audience connections. He also highlights the political impact of independent media and the evolving nature of content creation in today's digital world.

Taylor Lorenz, a sharp observer of internet culture and former journalist for major publications, shares her insights on the political landscape post-election. She discusses the pitfalls of the Harris campaign and why Democrats struggle to mirror Joe Rogan's media dominance. Lorenz reflects on her transition to independent content creation, highlighting the importance of personal branding in an era where traditional media's influence wanes. She also critiques the disconnect between online narratives and real-world issues, emphasizing the need for effective engagement with younger voters.

You want up-to-the minute election analysis? Sorry, not on this episode.But: If you want smart thoughts about politics and media and tech all merged together? We got you here, courtesy of The Atlantic’s Charlie Warzel, who came on to discuss how we should think about Elon Musk, Donald Trump supporter, being the same person as Elon Musk, guy who owns Twitter. Plus, because it’s Charlie: A useful way to think about what misinformation is, and isn’t.And! If you don’t want politics in your podcast today, we can accommodate that too, via a chat with Griffin Gaffney, the CEO/publisher of the San Francisco Standard. The Standard, owned by billionaire Mike Moritz, is a three-year-old news startup that lots of people in the Bay Area seem to love. And I wanted to know how he’s making it work, and the pros and cons of having a billionaire owner, and how he thinks the paper might actually turn a profit some day.Ideally, you’ll listen to both of these chats. But it’s a podcast! You do you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jon Lovett, co-founder of Crooked Media and former Obama aide, shares insights on successfully navigating the turbulent political media landscape since the 2016 election. He discusses the challenges of engaging with an increasingly divided electorate, especially amid the Trump era. Lovett reflects on the uninspiring election season, the personal impacts of a digital detox, and the humor found in political commentary. He also weighs in on Biden's debate performance and the concerns surrounding his age, adding a light-hearted touch with tales from reality TV.

Emma Tucker, the new Editor-in-chief of the Wall Street Journal, is shaking things up with her bold vision for modern journalism. She shares insights on increasing subscriptions through punchier stories and strategic staffing changes. Tucker also discusses her British journalism background and her recent controversial piece on President Biden. Additionally, she provides an update on reporter Evan Gershkovich, who's facing a challenging situation in Russia, underscoring the importance of journalist safety in today’s world.

Anjali Sud, CEO of Tubi and former head of Vimeo, dives into the revolutionary world of free streaming. She discusses how Tubi's ad-supported model is reshaping the entertainment landscape, allowing diverse stories to flourish beyond Hollywood's norms. Sud emphasizes the importance of data-driven content creation to cater to niche audiences and underrepresented demographics. With strategic partnerships and innovative marketing approaches, Tubi aims to redefine viewer engagement and challenge traditional streaming paradigms in an ever-competitive market.

Gabriel Sherman, a Vanity Fair writer and producer of the movie 'The Apprentice', discusses the tumultuous journey of creating a film about Trump's early career and his relationship with Roy Cohn. He reveals how the movie, seen as a complex and provocative portrayal, faced significant hurdles, including investor conflicts. Meanwhile, Jason Schreier, a Bloomberg reporter, dives into the troubled state of the video game industry, outlining the effects of layoffs, stagnation, and the challenges posed by new technologies while emphasizing the need for serious journalism in gaming.