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Two years ago, Katie Parrott was laid off from a crypto firm and couldn’t afford a career coach—so she turned to a $20-a-month ChatGPT subscription instead.

The Every staff writer’s habit of feeding AI good context eventually became compound writing, a codified system for brainstorming, drafting, and editing with AI. Today, that system is a plugin any writer can use.


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Will England is the CEO of Walleye Capital, a hedge fund managing nearly $10 billion in assets. An engineer by training with a math background from Oxford, he has spent his career at the intersection of machines and markets—and has made AI fluency mandatory for all 400 employees.


England believes refusing to use AI is like refusing to use the internet in 19...


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LLMs are a new medium for storytelling.That’s according to the creators of Portola, the company behind Tolan: an embodied AI companion that lives on its own planet and chats to you with a distinct personality. In 2025, Portola's founder and CEO Quinten Farmer and Head of Story Eliot Peper joined Dan Shipper to explain how they’re building this new medium from scratch. Their a...


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In 2025, Kevin Scott bet that the agentic web would be the next big thing in AI.

The Microsoft CTO argued that for agents to be genuinely useful, they'd need to be able to take action on our behalf—which would mean giving them access to the same sprawl of tools, data, and systems that make up the internet. Today, that bet is starting to pay off, as the foundational infr...


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Most consumer AI so far has been single-player: you and a chatbot, alone.

Benchmark partner Sarah Tavel, one of Pinterest's first 30 employees, is betting that's about to change. She's looking for a product genius who can build an AI product with social DNA: status, network effects, and multiplayer dynamics. That'll enable users of ChatGPT and other models to learn from...


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