CANADALAND CANADALAND

The A.I. App for Rich People to Fight Journalists Who Embarrass Them

May 4, 2026 · 41m

Summary

Jesse Brown interviews Aaron D'Souza, CEO of Objection.ai, an AI-powered tribunal designed to hold journalists accountable for alleged inaccuracies. D'Souza, known for helping Peter Thiel bankrupt Gawker, argues his platform offers a faster, more transparent alternative to traditional defamation lawsuits. The episode explores the tool's mechanics, including paid investigations by former intelligence agents and AI verdicts, while debating whether this adversarial model protects the wealthy or undermines press freedom and anonymous sourcing.

Topics discussed

Intro, ads, and episode overview Objection.ai and the Gawker/Hulk Hogan backstory How Objection.ai works: AI judges and honor indexes Interview with Aaron D'Souza on media accountability Ad break and Slow Burn promo Critiquing Objection.ai: Gaming the system and bias Journalist incentives, truth, and transparency Press councils, origin stories, and conclusion Outro, credits, and final ads
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