Mixed Signals from Semafor Media

Stephen Dubner, co-creator and host of Freakonomics, discusses the evolution of journalism and the value of curiosity-driven reporting. He reveals how he resisted selling to Spotify, critiques insider trading laws, and shares his new TV experiment that blurs the line between live discussions and podcasting. Dubner also dives into prediction markets versus traditional punditry, and amusingly contemplates opening a pizza place with a renowned chef. He argues that long-form storytelling remains vital, even in the face of industry shifts.

Sarah Rogers, Undersecretary of State for Public Diplomacy and a former First Amendment litigator, dives into the complex world of free speech regulation. She discusses her proactive stance against European tech laws, claiming they may chill speech. Rogers shares her early internet experiences, from Gawker comment sections to today’s digital challenges, framing them within a broader context of media evolution. She addresses accusations of partisanship regarding her advocacy for platforms like X and warns against selective enforcement of speech rules.

Justin Smith, CEO of Semafor, shares insights on the company’s impressive $30 million raise and its journey to profitability in just three years. He discusses future expansions in regions like the Gulf and East Asia, emphasizing a balance between quality journalism and sustainable growth. Ben Smith, editor-in-chief, dives into the importance of newsletters and editorial strategy, while reflecting on lessons learned from earlier digital media ventures. Together, they navigate the complexities of building a modern media company and the significance of events in enhancing brand relationships.

Veteran political journalist Ryan Lizza discusses his bold decision to publish an extensive Substack series about a personal and professional crisis. He reveals why New York Times coverage and Olivia Nuzzi's book motivated him to share his story. Lizza highlights the challenges he faced with legacy media, the impact of his series on his Substack audience, and his insights into RFK Jr.'s alleged influence on media reporting. With sharp critiques of traditional journalism, he reflects on lessons learned in today’s evolving media landscape.

Kevin O’Leary, Canadian businessman and Shark Tank star, dives into his role as a ruthless tycoon in the film Marty Supreme. He shares insights on collaborating with directors and actors like Josh Safdie and Timothée Chalamet. O'Leary discusses how reality TV shaped his public persona and emphasizes the value of earning respect over seeking popularity. He evaluates the future of movie theaters, the impact of media presence on policy, and reflects on his Canadian political experiences, providing a candid look at his multifaceted career.

Join Julian Shapiro-Barnum, creator of Recess Therapy, who shifts from theater to interviewing kids; Ananiya Williams of Gaydar, an LGBTQ quiz-show host advocating for safety and representation; and Jack Coyne of Trackstar, who books high-profile musical guests. They dive into how TikTok creators are reshaping media, the ethics of monetization, the awkward encounters with politicians like Kamala Harris, and the challenges of maintaining audience trust amidst growing fame and industry attention.

Janice Min, CEO of The Ankler and veteran entertainment journalist, and Emily Sundberg, founder of the Feed Me newsletter, dive into the chaotic media landscape of 2025. They discuss YouTube's overwhelming influence and the collapse of traditional right-wing media following Charlie Kirk’s saga. The duo critiques media newsletter insularity and debates the future of Substack, including new monetization strategies. With predictions for 2026, they see growth in niche media startups and a shifting audience dynamic around partisan personalities.

Adam Mosseri, the Chief Executive of Instagram, dives into the future of the platform, highlighting its evolution toward more TV-like content and the primacy of Reels and DMs. He discusses Instagram's strategic competition with TikTok and YouTube, addressing the challenges of 'AI slop' and the importance of raw, authentic content. Mosseri envisions how users will interact with Instagram on TV and the shifts in creator dynamics, all while predicting a more personalized and participatory future for the app.

Join comedian Andy Richter, best known as Conan O’Brien's sidekick, in a hilarious and insightful chat about his three-decade career. Andy reflects on the decline of late-night shows as cultural staples and his adaptation to new media, notably gaining TikTok fame from 'Dancing With the Stars.' He discusses the challenges of Hollywood's evolving landscape, the disparity in pay between sitcoms and talk shows, and the fun of podcasting compared to traditional interviews. With candid humor, he shares his life, career highs, and the thrill of game shows.

David Remnick, the longtime editor-in-chief of The New Yorker, discusses the magazine's evolution over its century-long existence. He shares insights on shifting from ad revenue to subscription models, emphasizing reader expectations for depth over hot takes. Remnick reflects on the challenges of adapting to digital media, reveals the role of AI in storytelling, and criticizes social media's toxic environment. He also shares a humorous anecdote about meeting Trump and highlights the importance of defending press freedom in today's landscape.