I worked with Steve Jobs at Apple, where every OS update killed startups. AI founders are about to face the same thing
The article discusses how Apple has historically rendered many startups obsolete with its OS updates, a phenomenon known as 'Sherlocking.' It highlights examples of companies like Tile and Pebble that struggled against Apple's competitive advantages. The author warns that AI founders may face similar challenges as the tech landscape evolves.
- ▪Apple's OS updates have consistently eliminated the need for many third-party tools and startups since the mid-2000s.
- ▪Companies like Tile and Pebble faced existential threats when Apple integrated similar features into its products.
- ▪Surviving startups like Dropbox and Spotify adapted by expanding their offerings beyond consumer features to thrive in a competitive environment.
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| Original publisher | Fortune |
| Canonical URL | https://fortune.com/2026/05/30/matt-rogers-nest-apple-sherlocking-ai-founders-hyperscalers/ |
| Publication time | Sat, 30 May 2026 12:30:00 +0000 |
| Retrieval time | 2026-05-30T12:49:36.360Z |
| Last seen | 2026-05-30T12:49:36.360Z |
| Headline source | Publisher (no WeSearch rewrite) |
| Excerpt source | publisher body |
| Excerpt method | First ~120 words (~800 chars) of extracted publisher body, fair-use limited. |
| Summary | WeSearch · cerebras-chat (WeSearch summarizer) |
| Summary source text | contentText |
| Citation coverage | Summary is a WeSearch-generated derivative; primary citation is the original publisher URL. |
| Cluster | qlkh4Ls5VLXf |
| Cluster logic | Grouped by semantic title/content similarity across sources within a rolling window. Same-publisher template collisions are excluded from coverage comparison. |
| Ranking reason | Story pages are not engagement-ranked. Hub feeds use recency, with optional source-diversified chronological ordering (cap consecutive stories per source). No personalized ranking. |
| Publisher visit | Yes — open original |
| Substitutes article? | No — link-out required for full text |
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| Indexing | May the item be indexed (stored, ranked, made findable)? | Allowed |
| Snippet | May a short excerpt of the publisher's text be shown? | Allowed |
| AI summary | May WeSearch generate its own short summary of the article? | Limited |
| Retrieval / RAG | May the content be exposed for third-party retrieval-augmented generation? | Not asserted |
| Model training | May the content be used to train AI models? | Not asserted |
| Commercial reuse | May the content be reused commercially? | Not permitted |
Basis: Derived from the published RSS/Atom feed. Contact: [email protected]. Reviewed: 2026-07-24.
Opening excerpt (first ~120 words) tap to expand
Apple famously rendered scores of startups and third-party tools obsolete with nearly every OS update since the mid-2000s. “Sherlocking” regularly kicked promising companies to the curb by effectively erasing their reason to exist — in many cases, by delivering nearly identical features and functionality.Recommended Video I saw it firsthand when I worked on the iPhone, iPod, and iPad under Steve Jobs. Every product launch and OS upgrade generated excitement for users and existential fear for founders. Founding teams spent years building capabilities that Apple could absorb into the operating system overnight. Life’s work became dead on arrival.
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Excerpt limited to ~120 words for fair-use compliance. The full article is at Fortune.
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