Evidence from 2024 shows that owners of large, high‑quality datasets did in fact start to earn recurring and strategically important licensing income from AI companies, even if the effect was not yet a full "turnaround" for the entire content industry.

• Reddit as a clear ‘major winner’: In its 2024 IPO filings, Reddit disclosed data‑licensing contracts signed in January 2024 with an aggregate value of about $203 million over 2–3 years, expecting at least $66.4 million of revenue in 2024 from these deals alone. This revenue was large enough that Reddit highlighted data licensing as a central growth driver, with non‑advertising revenue up sharply due to AI data deals (notably including Google). (techcrunch.com)
• Additional AI training deals for Reddit: In May 2024, OpenAI announced a partnership to use Reddit’s real‑time content for training its models and powering features in ChatGPT, reinforcing that Reddit’s corpus had become a paid, recurring input to leading AI systems rather than being scraped for free. (techcrunch.com)
• News publishers winning multi‑year, recurring contracts: In May 2024, OpenAI and News Corp (owner of The Wall Street Journal, The Times of London, The Sun, etc.) signed a five‑year licensing agreement giving OpenAI access to current and archived content for training and for direct use in responses; reporting put the deal’s value at over $250 million over the term, i.e., tens of millions of dollars per year. (apnews.com) OpenAI also struck multi‑year content and training deals with outlets like The Atlantic, Vox Media, Time, Condé Nast and others, turning a growing set of premium archives into recurring AI‑licensing revenue streams. (reuters.com)
• Broader shift toward paid licensing, not just scraping: By 2024, multiple publishers (e.g., AP, Axel Springer, Le Monde, Prisa Media, Dotdash Meredith) had signed structured content‑licensing agreements with OpenAI and similar firms, typically for recurring annual payments (often estimated in the low‑million‑dollar‑per‑year range). Collectively, these deals represent a new, industry‑wide revenue line built specifically on selling training and product‑use rights to AI companies, which is exactly the mechanism the prediction described. (reuters.com)
• Not universal, but directionally correct: Some of Jason’s named examples did not fully cash in during 2024 itself—e.g., The New York Times was still litigating against OpenAI/Microsoft and did not sign its first major AI licensing deal (with Amazon, worth an estimated $20–25M per year) until 2025, and YouTube’s opt‑in system for creators to authorize third‑party AI training launched only in December 2024, with no material 2024 revenue disclosed. (theverge.com) There was also substantial litigation (NYT, Ziff Davis and others) showing that not every rights‑holder had yet turned conflict into cash. (theverge.com)

Netting this out: 2024 did see major rightsholders with valuable datasets (Reddit, large news conglomerates and other premium publishers) emerge as clear economic winners from the AI boom via multi‑year, recurring licensing deals for training data and product integration. While the impact was uneven and smaller for some sectors than Jason’s "entire content industry" framing implies, the core prediction—that such rights‑holders would secure meaningful, recurring AI‑licensing income and become major business beneficiaries—was borne out by events in 2024.