This live episode of Bloomberg's Odd Lots podcast features hosts Joe Wiesenthal and Tracy Alloway interviewing Henry Blodget, CEO of Insider and former Wall Street analyst, at the On Air Fest 2026 conference.

The conversation explores AI's impact on financial markets, comparing current valuations and market dynamics to the dot-com bubble of the 1990s. Blodget discusses Open AI's meteoric rise from a $300 billion to $800 billion valuation and questions whether the company can justify such numbers.

The discussion shifts to media industry transformation, examining how AI tools are reshaping newsrooms while traditional distribution channels collapse. Blodget shares insights from his own AI newsroom experiments and the backlash they generated.

The hosts and Blodget analyze broader economic implications, from job displacement fears to the sustainability of current AI business models, drawing parallels between today's AI boom and previous technology cycles.

AI Valuations Reach Stratospheric Heights

Open AI's valuation skyrocketed from $300 billion to $800 billion since May 2024, with Blodget noting 'we are climbing' but questioning the sustainability of such multiples.

Unlike the 1990s dot-com era, AI companies face 'incredibly difficult' economics, losing money on power users while competitors like Google generate 'tens of billions of dollars of free cash flow' to fund chip purchases.

Private AI company shares are trading on secondary markets, with people offering stakes in Anthropic at $350 billion valuations despite no public financials available.

The Job Displacement Debate Gets Nuanced

Blodget challenges AI doom scenarios, pointing out that even pessimistic reports predict 'ten percent unemployment, which means ninety percent employment' - not economic armageddon.

Historical technology transitions like agriculture to industrial (from 93% to 2% farm employment over 200 years) created more jobs overall, suggesting AI may follow similar patterns.

The fear that 'no one will ever buy software anymore' because of AI code generation is 'hysteria' - enterprises won't replace billion-dollar software with junior employees using AI tools.

AI Lacks the Network Effects That Built Tech Giants

Unlike Google's search dominance, AI platforms have minimal switching costs - users can move from ChatGPT to Claude 'with almost no issues,' undermining Open AI's moat.

When Google Gemini matched ChatGPT's capabilities, Blodget realized 'maybe this actually is going to be like the Internet' where early leaders don't necessarily win long-term.

Of the first 500 companies that went public in the 1990s dot-com boom, only Amazon 'went on to actually make investors a lot of money after the crash.'

Media Industry Faces Structural Transformation

The media industry suffers from 'way too much capacity' with distribution shifting away from Facebook and Google back to direct subscriber relationships.

Blodget's AI newsroom experiment, creating five AI reporters with personalities and headshots in two hours, generated significant backlash but demonstrated practical applications.

Quality brands like Bloomberg, New York Times, and Wall Street Journal will benefit as AI-generated content creates more demand for trusted, edited sources.

AI tools excel at research and drafting but human skills in story selection, curation, and understanding 'what people care about and what a good story is' remain irreplaceable.

Corporate Leadership in the Trump Era

Despite promises of 'free speech' liberation, CEOs have become more timid and 'obsequious' to Trump, making pilgrimages while privately opposing policies like tariffs.

Blodget attributes CEO behavior to 'pragmatism' - public company leaders are 'easily removed' and must prioritize shareholders over personal political beliefs.