Overview of The Information Age
This episode of The Grill Room is a wide-ranging media industry roundup followed by an in-depth interview with Jessica Lessin, founder, editor-in-chief, and CEO of The Information. The first half focuses on major headlines in fashion media, sports journalism, sports-betting-adjacent deals, and cable news. The second half turns to Lessin’s company growth, why The Information is expanding in Asia and finance, how it thinks about AI and video, and why she remains committed to building the business rather than selling it.
Weekly Media News Roundup
Anna Wintour, John Galliano, and the Met Gala controversy
- The hosts discuss the backlash around Anna Wintour’s apparent push to rehabilitate John Galliano despite his history of antisemitic remarks.
- They frame it as a rare moment where someone long seen as untouchable in fashion and media was publicly checked.
- Key themes:
- Wintour’s long-held influence may be less absolute than it once was.
- The controversy highlights the limits of legacy power in a changing cultural landscape.
- Public institutions, especially in New York, face intense scrutiny around antisemitism and reputational judgment.
Pablo Torre’s reporting on Kawhi Leonard is vindicated
- The episode celebrates Pablo Torre’s independent reporting on alleged salary-cap circumvention involving Kawhi Leonard and the Clippers.
- The NBA’s findings appeared to validate Torre’s reporting after an earlier ESPN story seemed to undercut it.
- The hosts use this to make a broader point:
- Independent journalists can now break major stories that challenge powerful institutions.
- Legacy outlets like ESPN may face credibility questions when their framing appears too close to team or league spin.
- The result is a win for independent media and investigative reporting.
The Athletic, prediction markets, and ethics concerns
- The hosts discuss The Athletic’s brief interest in partnering with Kalshi after its prior betting partnership ended.
- They note the deal was ultimately dropped, but the episode treats the episode as a sign of how media is exploring new revenue streams.
- Concerns raised:
- The perception of ethics and conflicts of interest.
- Whether news organizations should get too entangled with gambling-adjacent products.
- The reputational risk for major brands like The New York Times.
The Athletic’s live show ambitions
- They also question The Athletic’s move into a live streaming/video show.
- The discussion is skeptical about whether a sports newsroom built around correspondents can compete in a crowded live-video market dominated by personalities.
- Their view:
- Live streaming is hard to do well.
- Not every newsroom should try to become a personality-driven entertainment brand.
- Audience demand for this format may be overstated for some legacy media players.
Maria Bartiromo’s abrupt exit from Fox News
- The hosts cover the sudden departure of Maria Bartiromo from Fox News, noting:
- She was off the air for nearly a month.
- There was no proper sendoff or explanation.
- They reflect on her unusual arc:
- Early career: respected, well-liked business journalist at CNBC.
- Trump era: became deeply aligned with Trump-world and a subject in major defamation lawsuits.
- The hosts imply her exit could signal unresolved behind-the-scenes issues, not just a routine departure.
Interview with Jessica Lessin
The Information’s record growth
- Lessin says The Information is in strong shape, with:
- Over 30% revenue growth in the first half of the year versus the same period last year.
- Improved profitability.
- Growth is being driven by:
- Subscriptions
- Advertising
- Brand partnerships
- Video
- Strong demand from business leaders, especially in tech and finance
Why The Information is investing in China coverage
- Lessin explains that The Information expanded its Asia coverage because there was a major reporting gap.
- She cites a simple but powerful observation:
- There were as many reporters covering Uber in San Francisco as there were covering the entire tech sector in China.
- She says the decision was both strategic and personal:
- She had prior experience reporting on Google’s exit from China.
- She wanted a deeper, on-the-ground understanding of the region.
- She emphasizes that in-person reporting still matters, even in an AI-saturated world.
AI is changing products, but not replacing journalism
- Lessin is optimistic about using AI to enhance journalism, not replace it.
- Example: The Information could use AI to make org charts more useful by adding analysis, patterns, and context.
- She argues that the best opportunities combine:
- Deep reporting
- Domain expertise
- Smart use of AI tools
- Her view on the broader AI market is cautious:
- Many people still don’t feel a real, everyday benefit from AI.
- The industry has not yet convincingly answered “why the world is better because of AI.”
- She worries the hype is outpacing real utility.
Video is now part of the business
- Lessin says she resisted video for years because The Information had no clear differentiated use for it.
- That changed as reporters became more visible and authoritative on camera.
- Current video products mentioned:
- TITV — a daily show mixing guests and reporters
- AI Deep Dive — a new long-form show focused on AI
- She sees video as an important growth area and a way to deepen audience engagement.
The Information’s product and audience strategy
- Lessin says the business is not trying to charge more just for the sake of it.
- Instead, she’s thinking about:
- How to serve a highly motivated professional audience
- What new products can add real value
- How to help readers understand a fast-changing tech/finance landscape
- She points to The Information’s pro tier as an example of higher-value, data-focused offerings.
The company structure and hiring philosophy
- The Information has just over 80 employees globally.
- Lessin says headcount will continue to grow, but selectively.
- Her hiring philosophy:
- Prioritize exceptional reporters with entrepreneurial drive
- Focus on talent that wants to build something new
- Grow only where the journalism justifies it
Why she is not interested in selling
- Lessin says she still has no interest in selling The Information.
- She views the company as a long-term project and says she can’t imagine waking up and wanting to do anything else.
- Her motivation is tied to:
- Building new institutions
- Shaping the future of tech and business journalism
- Creating lasting value through journalism and products
Her view on media entrepreneurs and independent journalists
- Lessin is supportive of reporters who leave institutions to build their own businesses.
- She explicitly praises former Information journalists and others who have launched independent outlets.
- Her take:
- Building independently is personal and requires being a jack-of-all-trades.
- Competition is healthy.
- The major legacy outlets have already adapted in response to independent success.
Investing in media
- Lessin says she enjoys investing in media startups and has backed several publications, including:
- Semaphore
- Dynamo
- Racket
- She sees this as a way to support talented founders and help new media businesses get connected to the right people.
Key Takeaways
- Media power is shifting: Long-dominant figures like Anna Wintour still matter, but they are more vulnerable to pushback than they used to be.
- Independent journalism is gaining credibility: Pablo Torre’s vindication is framed as a win for creator-led investigative reporting.
- Legacy media faces ethical and strategic pressure: From prediction markets to live video, big outlets are experimenting in ways that raise questions about trust and identity.
- The Information is thriving: Lessin presents the company as a rare media growth story, powered by strong reporting, subscription value, and smart expansion.
- AI is useful, but not transformative yet: Lessin sees promise, but she’s skeptical of the hype and notes that the public still isn’t convinced.
- The future of media is hybrid: Reporting, video, product design, and entrepreneurial thinking are increasingly intertwined.