Barry Diller, a legendary media mogul and the chairman of IAC and Expedia, joins Dylan for a dynamic conversation about the shifting media landscape. They discuss the future of Comcast's cable assets and whether they'll find success as a reimagined bundle. The pair dives into The Daily Beast's potential evolution into a business powerhouse. Barry also shares his optimistic outlook on the Democratic Party’s future amid the challenges posed by Trump and Elon Musk, offering a fresh perspective on resilience in the industry.

Troy Young, former president of Hearst Magazines and now a media advisor and investor, joins Dylan for an insightful discussion. They dissect the challenges faced by The Washington Post and CNN, questioning whether current leadership can steer these giants through turbulent times. Troy highlights the need for authenticity in media, critique scripted news, and the importance of engaging content to attract modern audiences. The conversation also touches on the transformative impact of digital platforms and the evolving dynamics of media consumption.

Andrew Morse, CEO of The Atlanta Journal-Constitution and former digital chief of CNN, shares insights from his extensive media career. He discusses the unceremonious cancellation of CNN+ and what it reveals about challenges in the news landscape. Morse also reflects on his clashes with CNN's leadership and the necessity for a direct-to-consumer model. He emphasizes revitalizing local journalism by investing in quality content and technology to engage diverse audiences, all while navigating the complexities of today’s media environment.

Jeremy Boreing, co-founder of The Daily Wire, dives into the explosive growth of alternative media and its influence on politics. He critiques legacy media's failures to resonate with modern audiences and sheds light on the effective strategies that helped his company approach $200 million in revenue. The conversation highlights the shifting political narratives ahead of the 2024 election, the challenges media faces in reflecting public sentiment, and the importance of fostering authentic discussions in a polarized landscape.

Jake Sherman and Anna Palmer, co-founders of Punchbowl News and former Politico stars, share their journey from top journalists to media innovators. They discuss the inception of Punchbowl and its laser focus on Capitol Hill news. The duo dives into the challenges of navigating the ever-changing media landscape, the revolutionary data integration tool for Capitol Hill professionals, and the potential of niche subscription markets. They reflect on the importance of audience engagement and the competitive spirit needed to thrive in today's journalism.

Jon Kelly joins Dylan to discuss the cascading effects of Brian Roberts’ monumental decision to spin off NBCUniversal’s declining cable assets. Then they get into Rachel Maddow’s $125 million contract renegotiation and how MSNBC survives without the NBC mothership. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

It’s a food media-themed doubleheader in The Grill Room! First, Dylan convenes with The Infatuation C.E.O. Paul Needham, who discusses the economics of his restaurant recommendation empire. Then acclaimed food writer and entrepreneur Alison Roman stops by to discuss her journey from legacy media to entrepreneurship and why her defenestration from The New York Times turned out to be a blessing in disguise. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

CNBC's Alex Sherman joins Dylan for the ultimate dish-fest across a series of juicy and mission-critical topics--Disney succession tea leaves, Dana Walden versus the outsiders, John Malone's Maffei moves, NBC's "Roundball Rock" deal blockers, Comcast's cable trial balloon, and much more. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Jim VandeHei, co-founder and CEO of Axios, shares insights on the shifting media landscape post-Trump victory. He discusses Elon Musk's influence on conservation media through X, and how traditional outlets like CNN struggle to retain relevance. VandeHei emphasizes the need for legacy media to adapt and maintain journalistic integrity amidst fragmentation. The conversation also touches on the changing dynamics of political coverage, highlighting the challenges in nurturing passionate journalists and the call for objective reporting in today's climate.

Dylan is joined by veteran Republican strategist and never-Trump media darling Tim Miller for an incisive post-election postmortem. Together, they dissect how the election unfolded, examine the failures of Democrats and the media to anticipate this new reality, and discuss what lies ahead for the political-media landscape. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices