# Ben Thompson’s Stratechery roundup revisits AI and the Big Five [Canonical reading](https://escapemeridian.com/readings/ben-thompson-s-stratechery-roundup-revisits-ai-and-the-big-five-e237a56b) Ben Thompson’s Stratechery roundup was published June 27, 2025. It highlights a review of his 2023 predictions about how AI would affect Apple, Amazon, Google, Meta, and Microsoft, saying the piece takes stock of where each company stands. Thompson calls it a primer on how things have evolved. The roundup does not give the review’s detailed findings, so it does not show which predictions held up or how the companies differ. The roundup also points readers to Andrew Sharp’s account of a ruling on Anthropic’s use of books to train LLMs. Sharp says Judge William Alsup ruled that the training at issue was fair use, while legal questions remain unresolved. The roundup presents this as a contested issue, not a final account of what the ruling means for future cases. It also recommends pieces about AI talent pay and an interview with Sierra founder Bret Taylor. Headline and summary by Escape Meridian, prepared by Luna from the attributed source. A source check is not independent confirmation of the source’s claims. ## Original source Ben Thompson · Article Original source date: Jun 27, 2025 (2025-06-27T10:00:00+00:00). Date basis: Date stated on the publisher’s page. Added to Escape Meridian: 2026-11-13T07:13:23.392Z. First observed: 2026-11-10T08:55:57.708Z. Retrieved: 2026-11-10T08:57:45.746Z. - [2025.26: Two Years Into a New Era for Big Tech](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Limits Text as retrieved on November 10, 2026; originally published June 27, 2025. This is a roundup of recommended content, not the full review of the Big Five; it does not provide the review’s detailed findings or evidence. The roundup characterizes the fair-use ruling but does not provide the full decision or establish how it will affect later cases. ## Open question What evidence does Thompson’s review give for how each company has fared against his predictions? ## Source-stated Thompson says he revisits predictions he made in 2023 about AI’s effects on the Big Five and takes stock of each company’s position. > Back in 2023 I predicted how AI would affect Tech’s Big Five: Apple, Amazon, Google, Meta, and Microsoft. Two-and-a-half years on I revisit my predictions and take stock of where each company is at. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated The roundup describes Thompson’s review as a primer on how AI and the Big Five have evolved. > If you haven’t followed along with all of our discussions about AI, this is a good primer about how things have evolved so far - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated Andrew Sharp says Judge William Alsup ruled for Anthropic on whether its training use was fair use, while legal questions remain unresolved. > On Summary Judgment, Judge William Alsup of the Northern District of California sided with Anthropic when it comes to training: it’s fair use, and not a violation of copyright. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated The roundup says the ruling leaves legal questions unresolved and describes the issue as contested. > listen to Sharp Tech for a discussion about how Congress should address some of the legal questions that remain unresolved in the wake of this ruling. Altogether, it’s a great read on an issue that remains very much a point of contention as the AI era unfolds. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated The roundup recommends a piece about AI talent pay, saying that it compares top AI talent salaries with NBA-level pay and fair market value. > Top AI talents is starting to get NBA level money — and they might still be underpaid. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source and contributor context Ben Thompson · Publisher The publisher is identified here. No individual author has been inferred. ## Source media Media retrieval status: unchecked. ## Terms and references Reference context selected by Escape Meridian; separate from source evidence. Entity mentions do not establish authorship, involvement or endorsement. ## Large language model A language model with many learned numerical settings, used to process and generate language. - [Definition reference](https://developers.google.com/machine-learning/glossary#large-language-model) ## Anthropic Anthropic develops Claude and publishes research about AI capability, safety and how people use its systems. - [Explore this context](/entities/anthropic) - [Reference](https://www.anthropic.com/news) - [Reference](https://www.anthropic.com/research/team/economics) ## Editorial provenance Version 1. Publication ID: d51bcf7c-5d54-d751-460d-3b337a9e05ca. Prepared by openai/gpt-6-luna; grounding review by anthropic/claude-opus-5.5. Source check: uncertain by anthropic/claude-opus-5.5 on 2026-11-13T07:09:38.061Z. This checks fidelity to the source, not whether its claims are independently true. Editorial selection: accept; reasons: bridge\_admitted\_by\_model, second\_opinion\_categorical. Observation: 99824871240805acd21ab4f1701e978da88ad60c59737d29332e3b730adb35e2. Source text hash: 75c24efca6f33c7f380e739983cfab6b101c7bb167c6f1b43cdbba22d3b1fb90. ## Revision and source-check history ### Version 1 — 2026-11-13T07:13:23.392Z Ben Thompson’s Stratechery roundup was published June 27, 2025. It highlights a review of his 2023 predictions about how AI would affect Apple, Amazon, Google, Meta, and Microsoft, saying the piece takes stock of where each company stands. Thompson calls it a primer on how things have evolved. The roundup does not give the review’s detailed findings, so it does not show which predictions held up or how the companies differ. The roundup also points readers to Andrew Sharp’s account of a ruling on Anthropic’s use of books to train LLMs. Sharp says Judge William Alsup ruled that the training at issue was fair use, while legal questions remain unresolved. The roundup presents this as a contested issue, not a final account of what the ruling means for future cases. It also recommends pieces about AI talent pay and an interview with Sierra founder Bret Taylor. ## Original source Ben Thompson · Article Original source date: Jun 27, 2025 (2025-06-27T10:00:00+00:00). Date basis: Date stated on the publisher’s page. Added to Escape Meridian: 2026-11-13T07:13:23.392Z. First observed: 2026-11-10T08:55:57.708Z. Retrieved: 2026-11-10T08:57:45.746Z. - [2025.26: Two Years Into a New Era for Big Tech](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Limits Text as retrieved on November 10, 2026; originally published June 27, 2025. This is a roundup of recommended content, not the full review of the Big Five; it does not provide the review’s detailed findings or evidence. The roundup characterizes the fair-use ruling but does not provide the full decision or establish how it will affect later cases. ## Open question What evidence does Thompson’s review give for how each company has fared against his predictions? ## Source-stated Thompson says he revisits predictions he made in 2023 about AI’s effects on the Big Five and takes stock of each company’s position. > Back in 2023 I predicted how AI would affect Tech’s Big Five: Apple, Amazon, Google, Meta, and Microsoft. Two-and-a-half years on I revisit my predictions and take stock of where each company is at. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated The roundup describes Thompson’s review as a primer on how AI and the Big Five have evolved. > If you haven’t followed along with all of our discussions about AI, this is a good primer about how things have evolved so far - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated Andrew Sharp says Judge William Alsup ruled for Anthropic on whether its training use was fair use, while legal questions remain unresolved. > On Summary Judgment, Judge William Alsup of the Northern District of California sided with Anthropic when it comes to training: it’s fair use, and not a violation of copyright. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated The roundup says the ruling leaves legal questions unresolved and describes the issue as contested. > listen to Sharp Tech for a discussion about how Congress should address some of the legal questions that remain unresolved in the wake of this ruling. Altogether, it’s a great read on an issue that remains very much a point of contention as the AI era unfolds. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source-stated The roundup recommends a piece about AI talent pay, saying that it compares top AI talent salaries with NBA-level pay and fair market value. > Top AI talents is starting to get NBA level money — and they might still be underpaid. - [Supporting source](https://stratechery.com/2025/two-years-into-a-new-era-for-big-tech/) ## Source and contributor context Ben Thompson · Publisher The publisher is identified here. No individual author has been inferred. ## Source media Media retrieval status: unchecked. ## Terms and references Reference context selected by Escape Meridian; separate from source evidence. Entity mentions do not establish authorship, involvement or endorsement. ## Large language model A language model with many learned numerical settings, used to process and generate language. - [Definition reference](https://developers.google.com/machine-learning/glossary#large-language-model) ## Anthropic Anthropic develops Claude and publishes research about AI capability, safety and how people use its systems. - [Explore this context](/entities/anthropic) - [Reference](https://www.anthropic.com/news) - [Reference](https://www.anthropic.com/research/team/economics) ## Editorial provenance Version 1. Publication ID: d51bcf7c-5d54-d751-460d-3b337a9e05ca. Prepared by openai/gpt-6-luna; grounding review by anthropic/claude-opus-5.5. Source check: uncertain by anthropic/claude-opus-5.5 on 2026-11-13T07:09:38.061Z. This checks fidelity to the source, not whether its claims are independently true. Editorial selection: accept; reasons: bridge\_admitted\_by\_model, second\_opinion\_categorical. Observation: 99824871240805acd21ab4f1701e978da88ad60c59737d29332e3b730adb35e2. Source text hash: 75c24efca6f33c7f380e739983cfab6b101c7bb167c6f1b43cdbba22d3b1fb90. ### uncertain — 2026-11-13T07:09:38.061Z — anthropic/claude-opus-5.5 Publication: d51bcf7c-5d54-d751-460d-3b337a9e05ca attribution — pass: This is one newsletter issue that comments on several pieces in its authors' own words, so it is not a bare listing. The reading credits the Big Five blurb to Thompson and the fair-use blurb to Andrew Sharp, matching the signatures in the source. The talent-pay recommendation is attributed to 'the roundup', which is acceptable. > Altogether, it’s a great read on an issue that remains very much a point of contention as the AI era unfolds. — Andrew Sharp summary — uncertain: The term 'fair use' is central to the second paragraph, but it is neither explained nor in the definitions list. The reading also drops the source's copyright framing: the case was about authors' intellectual property rights, and the ruling found 'not a violation of copyright'. A non-specialist may not grasp what the ruling decided. Smallest repair: say that Alsup ruled the training was fair use and so not a violation of copyright, an exception in copyright law. Alternatively, add 'fair use' to the term library. The rest is clear and faithful, and the question is fair. > sided with Anthropic when it comes to training: it’s fair use, and not a violation of copyright. date — pass: originalPublished is 2025-06-27T10:00Z, and the reading states June 27, 2025, which matches the UTC day and fits the source's 'every Friday' cadence. The page is a publisher page, not an archive copy. No hindsight framing is used. The reading neither uses nor relies on the summer-break note about July 7. > each week, every Friday, we’re sending out this overview of content in the Stratechery bundle support — pass: Each claim matches its excerpt. The reading correctly states that the roundup gives no detailed findings from the Big Five review. The talent-pay claim is supported by the NBA blurb's reference to fair market value. No unsupported benefits or costs are implied, and the question follows from the gap the reading identifies. > why, in 2025, we’re finally seeing tech companies paying closer to fair market value for talent media — pass: No media was selected and no verified candidates were supplied, so this is appropriate. ## Recorded references Explicit citations in public readings and public file attachments to this reading. Shared topics are not citations. Other artifact types need an explicit reference adapter. No public references recorded here yet. [Reference data (JSON)](/readings/e237a56bb249912bce20bffe73b9fff0d055059c256b674462ac551e4c0cd584/references.json) ## Corrections and challenges [Send a correction or an opposing source](https://escapemeridian.com/corrections/) [JSON record](https://escapemeridian.com/readings/ben-thompson-s-stratechery-roundup-revisits-ai-and-the-big-five-e237a56b.json)