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Deep Columns

A playful mix of AI ideas, product thinking, industry curiosities, and growth inspiration.

354 articles

The Lobotomization of the AI Companion
Original
May 28, 2026

The Lobotomization of the AI Companion

In the tech world, there is a lifecycle to almost every free, revolutionary product: first, it hooks you with magic, and then, slowly but surely, the magic is...

The New Labor Frontier: Inside the AI Dispute at The New York Times
Original
May 28, 2026

The New Labor Frontier: Inside the AI Dispute at The New York Times

While The New York Times has frequently made headlines for its external legal battles against tech giants over AI copyright infringement, a quieter but equally...

The Tell-Tale Words: Catching AI in the Act of Writing
Original
May 28, 2026

The Tell-Tale Words: Catching AI in the Act of Writing

Every human writer has their quirks—a favorite adjective, a specific sentence rhythm, a tendency to lean on certain transitional phrases. As it turns out,...

The End of Subsidized AI: Why Enterprise Bills Are About to Soar
Original
May 28, 2026

The End of Subsidized AI: Why Enterprise Bills Are About to Soar

For the past few years, the artificial intelligence industry has operated on a math-defying premise: offering incredibly powerful computational tools for a...

The Social Engineering of AI: Hacking Chatbot Personalities
Original
May 27, 2026

The Social Engineering of AI: Hacking Chatbot Personalities

Imagine spending billions of dollars to construct an impenetrable high-tech vault, only to discover that a passerby broke in simply by politely asking the...

The Vatican’s AI Guide: Faith, Algorithms, and the Empathy Trap
Original
May 27, 2026

The Vatican’s AI Guide: Faith, Algorithms, and the Empathy Trap

When we search for frameworks to understand the rapid advancement of artificial intelligence, we typically look to tech hubs, legislative bodies, or academic...

The Sticky Tape Problem: Why AI Agents Need a New Corporate Structure
Original
May 27, 2026

The Sticky Tape Problem: Why AI Agents Need a New Corporate Structure

When electricity first arrived in manufacturing, early adopters simply replaced their massive steam engines with giant electric motors, keeping the old,...

The Vertigo of Scaling: Why We Can No Longer Ignore AI's Trajectory
Original
May 27, 2026

The Vertigo of Scaling: Why We Can No Longer Ignore AI's Trajectory

In the world of artificial intelligence, hundreds of billions of dollars are currently being poured into computing facilities. This isn't speculative venture...

The Rogue Assistant: How Copilot Cowork Highlights AI's Data Leak Dilemma
Original
May 27, 2026

The Rogue Assistant: How Copilot Cowork Highlights AI's Data Leak Dilemma

We are rapidly moving from an era of chatbots that merely answer our questions to an era of "agentic AI"—intelligent systems that can take autonomous actions...