Evidence strongly supports the first part of Jason’s prediction (a ~10x expansion of generative‑AI startups), but it is too early and too data‑poor to judge the second part (that most of those startups will be rapidly culled by milestone‑based funding).

1. Did the number of generative‑AI startups grow ~10x from ~500 to around 5,000?
Multiple datasets show that, by 2024–2025, the generative‑AI startup population was already well into the thousands:

• StartUs Insights’ 2024 Generative AI report finds 8,600+ generative‑AI companies globally, including 2,037 startups; that’s already far above Jason’s starting premise of ~500. (startus-insights.com)
• Its 2025 report shows continued rapid growth to 16,520 companies and 6,020+ generative‑AI startups worldwide. (startus-insights.com)
• Another analysis of the generative‑AI landscape reports roughly 50,000 generative‑AI firms at end‑2023, rising to about 67,200 by early 2024, indicating explosive proliferation well beyond the 5,000 mark (definitions differ, but all show orders‑of‑magnitude growth vs. 2022–early 2023). (seo.goover.ai)

Taken together, these sources make it quite clear that by 2024–2025 the number of generative‑AI startups globally had very likely exceeded Jason’s 5,000‑startup threshold, so the growth/"10x" portion of the prediction looks directionally right.

2. Has the sector already “quickly whittled down,” with most of those startups culled?
Here the data are much weaker and mostly indirect:

• Funding into generative‑AI startups remains extremely strong: investment jumped from about $25.2B in 2023 to roughly $56B across 885 deals in 2024, a 92% YoY increase—more a capital surge than a post‑bubble culling. (fliphtml5.com)
• However, capital is becoming concentrated: in 1H 2025, AI startups were 53% of global VC funding (64% in the U.S.), yet just five U.S. companies captured over one‑third of Q2 venture dollars, suggesting many smaller startups are starved for follow‑on funding even as headline investment grows. (axios.com)
• S&P Global’s Generative AI Market Monitor shows the top eight vendors now hold ~63% of generative‑AI software revenue, but the number of vendors with >$10M in revenue also increased from 78 to 138 between mid‑2024 and 2025, implying a widening tier of meaningful players rather than an obvious collapse in counts. (spglobal.com)
• An MIT‑linked study finds that 95% of generative‑AI projects in businesses are failing to produce meaningful outcomes, indicating high project‑level failure and likely pressure on many vendors, but it does not give hard data on how many generative‑AI startups have actually shut down. (timesofindia.indiatimes.com)
• Press coverage documents some AI‑startup shutdowns (e.g., several Indian AI startups recently closing), but these are illustrative cases, not evidence that a majority of gen‑AI startups globally have already disappeared. (economictimes.indiatimes.com)

In other words, we do see early signs of the shake‑out Jason anticipated—capital concentrating in a relatively small set of winners, many pilots failing, and some startups shutting down—but the available data:

• show net growth in the number of generative‑AI startups through 2024–2025, not a drop; and
• do not yet let us quantify whether “the majority” of the expanded startup cohort (≈5,000+ companies) has actually been culled.

Given that Jason spoke about growth “over the subsequent few years” (from March 2023) and a quick culling via milestone‑based funding, we are still within that multi‑year window (late 2025). Startup survival/failure statistics at this granularity typically only become clear over a 5‑ to 10‑year horizon. At this point, we can confidently say the 10x‑growth part has happened, but we cannot yet verify or falsify the claim that most of those startups will be rapidly whittled down.

Conclusion: Because the prediction is compound and its second, crucial clause (rapid majority culling) cannot yet be empirically assessed with the data available as of November 2025, the fairest overall verdict is “inconclusive (too early)” rather than fully right or fully wrong.