AI & Technology — The Sideline

When AI Runs the Money: Why Algorithmic Architecture Is Now a Systemic Risk Problem

AI systems in finance are converging around the same architectures, the same training data, and the same vendors—creating a monoculture that could make the next market crisis faster, more synchronized, and much harder to stop.

Dispatch desk · May 26, 2026

AI Safety & Policy

The Pope Has an AI Advisor Now — Here's Why That's More Interesting Than It Sounds

Pope Leo's new encyclical on AI — backed by an Anthropic co-founder — calls out power concentration as a moral threat. Here's why engineers should pay attention, cynicism and all.

Dispatch desk · May 26, 2026

AI Startups

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179 articles

AI Startups

Buffett's Berkshire Bets Big on AI: What the Oracle's Portfolio Move Actually Tells Us

When Berkshire Hathaway accumulates an AI stock position, it's worth understanding what their investment framework actually reveals about where durable value sits in the AI landscape—beyond the headlines.

Dispatch desk · May 26, 2026

AI Startups

AI Stocks Are Printing Money for Everyone Else—Here's Why I'm Still Sitting on My Hands

AI is a genuinely powerful technology—but 'the tech works' and 'these valuations make sense' are two completely different claims. Here's what the bull case is missing.

Dispatch desk · May 26, 2026

Cox Media Fined $930K For Lying About Listening To Your Phone Conversations

Cox Media and two marketing partners just paid $930,000 to the FTC—not necessarily for actually listening to your phone, but for claiming they could. A masterclass in how bragging about surveillance capabilities you may not even have is still very much illegal.

578% Revenue Growth? Let's Actually Look Under the Hood of This AI Darling

A tiny AI company posting 578% revenue growth sounds like a headline worth celebrating. But before you break out the champagne, let's ask the questions the press release conveniently skipped.

The Sideline.

When AI Runs the Money: Why Algorithmic Architecture Is Now a Systemic Risk Problem

The Pope Has an AI Advisor Now — Here's Why That's More Interesting Than It Sounds

Buffett's Berkshire Bets Big on AI: What the Oracle's Portfolio Move Actually Tells Us

AI Stocks Are Printing Money for Everyone Else—Here's Why I'm Still Sitting on My Hands

Cox Media Fined $930K For Lying About Listening To Your Phone Conversations

578% Revenue Growth? Let's Actually Look Under the Hood of This AI Darling

I Fine-Tuned an LLM Into C-3PO to Find the Best Way to Actually Inject a Persona

The ARR Shell Game: How AI Startups Are Cooking Their Revenue Books

Nvidia's Chokehold on AI: How a Graphics Card Company Became the Infrastructure Behind Everything That Matters

AI/R Wants to Be Your AI Budget Watchdog—Here's Why That's Actually Harder Than It Sounds