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ChatGPT Group Chats, Meta and the Encryption Trade-off, Network Effects and Ad Models

Monday, November 17, 2025

ChatGPT is getting group chats, a long-standing Stratechery feature request. It’s also a clear attach against Meta, who can’t respond because of encryption, while Google looms.

Perplexity Search Ads, Inventory-Defined Advertisers, Telegram Follow-Up

Tuesday, August 27, 2024

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Perplexity’s upcoming advertising model looks a lot different than traditional search advertising; it may always look different.

Telegram CEO Arrested, Telegram’s Non-Encrypted Advantage, Telegram Complexities

Monday, August 26, 2024

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Telegram’s CEO was arrested. The case is very complex, in part because the realities of messaging and security and encryption are very complex.

The WhatsApp Kerfuffle, Comparing Messaging Services, Network Effects

Thursday, January 14, 2021

Some number of people are downloading alternative messaging apps after WhatsApp changed its privacy policy; Facebook’s problem is a narrative one, not a factual one.

The NBA on Christmas: Best Games, Banner Talk, Wemby vs. the Thunder, Anta Claus, and a Quarter-Zip Ultimatum

Perplexity Search Ads, Inventory-Defined Advertisers, Telegram Follow-Up

The NBA on Christmas: Best Games, Banner Talk, Wemby vs. the Thunder, Anta Claus, and a Quarter-Zip Ultimatum

The Knicks Silence the Haters, Closing the Book on the Cup, Chris Paul Sadness and Giannis Weirdness

2025’s Top Apps

ChatGPT Image 1.5; Apple v. Epic, Continued; Holiday Schedule

An Interview with Rivian CEO RJ Scaringe About Building a Car Company and Autonomy

Disney and OpenAI, Totems in an AI World, Google Versus the World

The NBA on Christmas: Best Games, Banner Talk, Wemby vs. the Thunder, Anta Claus, and a Quarter-Zip Ultimatum

The Knicks Silence the Haters, Closing the Book on the Cup, Chris Paul Sadness and Giannis Weirdness

2025’s Top Apps

An Interview with Rivian CEO RJ Scaringe About Building a Car Company and Autonomy

An Interview with Ryan Jones About Flighty and Building Apps in 2025

An Emergency Interview with Michael Nathanson About Netflix’s Acquisition of Warner Bros.