Mixed Signals from Semafor Media

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.

Paula Kerger, CEO of PBS, discusses the existential threats facing public broadcasting amid political attacks. She highlights how recent GOP efforts are more coordinated than before and the potential impact of losing federal funding on local stations. Kerger passionately defends PBS's unique role in providing quality children's programming and its importance as critical infrastructure for underserved communities. The conversation also touches on the influence of Trump's grievances, the ongoing fight to maintain bipartisan support, and comparisons to global public media challenges.

Jodi Kantor, an investigative reporter at The New York Times known for her groundbreaking work on the Weinstein case, dives into the secrets of the U.S. Supreme Court's internal culture. She reveals the court's enduring secrecy, the impact of recent justices on its public persona, and the nuances of liberal dissent between Kagan and Jackson. Kantor also discusses the cultural dynamics at play, the implications of the Dobbs leak, and how her experiences in the #MeToo era inform her journalistic approach to power and accountability.

Derek Thompson, journalist and co-author of Abundance, dives into the intriguing notion that all media is becoming television. He unpacks the rise of endless video flows in podcasting and social apps, predicting potential national attention deficits. Thompson discusses the survival of long-form media amidst quick bites of content and explores the charisma behind impactful on-camera performances. Additionally, he shares insights on his shift to independent publishing and the surprising success of his book, revealing a curiosity-driven approach to exploring diverse topics.

Will Welch, the Global Director and editor-in-chief of GQ US, dives into modern masculinity and the magazine's evolution. He discusses GQ's strategy to address the manosphere and embraces diverse male perspectives. Will reveals how GQ prioritizes quality storytelling over clickbait, emphasizing thoughtful engagement with subcultures. He highlights his collaborative experiences with celebrities like Robert Pattinson, touching on the impact of cultural shifts on men's fashion and the importance of hiring young talent to stay relevant.