On with Kara Swisher
On with Kara Swisher

Journalists or Creators? How Media Entrepreneurs Are Reshaping News

Legacy media isn’t dead, but journalists are leaving traditional outlets in swarms to launch their own newsletters, podcasts and social media ventures, and they may be forcing a reboot. As one of the early media entrepreneurs (and a trusted advisor to many of those who aspire to follow in her footst

Featured Speakers

Katie Drummond Guest

Topics Discussed

Episode Summary

Executive Summary: Kara Swisher moderates a lively discussion with Katie Drummond, Oliver Darcy, and David Jorgenson about the reinvention of media through subscriptions, newsletters, video, creator-style branding, and entrepreneurial independence. The panel agrees legacy media is shrinking and consolidating, but not dead, while independent outlets can thrive by prioritizing original reporting, direct audience relationships, and legal/financial discipline. AI and platform dependence are major threats, but also catalysts for a more human-led, multi-platform future.

Main Topics: Legacy media is consolidating, not disappearing (Priority: 5/5): The panel argues that legacy institutions still have brand value, but they are shrinking, leaner, and increasingly unable to sustain the bloated newsroom models of the past. Independent media as an entrepreneurial path (Priority: 5/5): Darcy and Jorgenson describe building newsletter/podcast/video businesses outside large organizations, emphasizing speed, autonomy, and audience ownership. Traffic apocalypse and platform dependence (Priority: 5/5): Drummond explains how Google AI overviews and shifting algorithms weaken publisher traffic, making old reliance on search and social distribution unsustainable. Creator culture and journalist authenticity (Priority: 4/5): All three discuss the rise of personality-driven journalism, with enthusiasm for direct audience connection but concern about creators impersonating journalists. AI as a threat to quality and discoverability (Priority: 4/5): The panel sees AI-generated content and summaries as degrading the information ecosystem, while still allowing limited use for research and administrative tasks. Legal risk and defamation insurance (Priority: 4/5): They discuss the rising costs and chilling effect of litigation from powerful figures, especially for small publishers without large legal infrastructure. Subscription-first business models with selective advertising (Priority: 4/5): Subscriptions are framed as the core revenue engine, though advertising can support accessibility and growth if managed carefully.

Key Arguments: Legacy media will likely survive in smaller, leaner forms, but many titles and jobs will disappear as consolidation continues. Independent publishers have an advantage because they start with lower overhead and can move faster than large institutions. Original reporting is the best defense against AI slop, search disruption, and audience fragmentation. Direct audience relationships through newsletters, podcasts, YouTube, and TikTok reduce dependence on Google/Facebook algorithms. Journalists should embrace creator tools and personality, but must not confuse authentic journalism with performative creator branding. Legal protection is now a major hidden cost for independent media, making insurance and lawyers essential. Subscriptions create the most durable connection to readers, but advertising can still subsidize free access and expand reach. Entrepreneurial newsroom culture should reward staff who build breakout products and allow them to become stars, even if they eventually leave. The key to avoiding audience capture is to lead with facts and originality rather than tailoring work to partisan or subscriber preferences. AI can assist with back-end functions and research, but not replace source-driven reporting or nuanced editorial judgment.

Data Points: Oliver Darcy total subscribers: Over 90,000 - Status newsletter audience size, with several thousand paid subscribers Oliver Darcy paid subscribers: Several thousand - Paid portion of Status's subscriber base Status age: 11 months - Darcy says the publication is less than a year old and already near 100,000 total subscribers Katie Drummond subscriber growth: Triple-digits growth - Wired saw very strong subscriber growth over the last six months Wired growth period: Last 6 months - Timeframe for the subscriber surge Drummond mentions Washington Post Universe engagement: 75x more engagement per video - Jorgenson says his YouTube account outperformed the Washington Post flagship account Washington Post Universe views: 6.6x more overall views - Compared with the Washington Post flagship account YouTube audience: Just over 100,000 subscribers - Jorgenson's Local News International YouTube following Trump settlements with media: $16 million and $15 million - CBS and ABC settlements referenced as examples of legal pressure on media Meta settlement: $25 million - Referenced as another example of high-cost legal disputes Trump lawsuit against WSJ: $10 billion - Example of litigation risk from powerful figures Defamation insurance (Beehive): Up to $1 million - Darcy cites insurance coverage available through Beehive Daily vet bills over $1,000: Every 6 seconds - Sponsor copy for Fetch Pet Insurance, not editorial content

Pivotal Quotes: "I really think about it less as death and more as consolidation." — Katie Drummond: On whether legacy media is dying "We are reaching, I think, like the end of that game." — Katie Drummond: On the collapse of traffic dependence and the traffic apocalypse "I do think that the incentive model in journalism has to account for that entrepreneurial ship." — Katie Drummond: On rewarding staff who create successful new media products

Implications: Media will be increasingly direct, video-heavy, and subscription-led, with journalists expected to act like entrepreneurs while retaining reporting rigor. The winners will be outlets that build trust, own their audience relationships, and can survive platform volatility and legal pressure.

🔓 Sign Up for Unlimited Episode Search

About On with Kara Swisher

View all episodes from On with Kara Swisher