The 21 Hats Morning Report

The 21 Hats Morning Report

Don’t Turn Your Business Over to AI Just Yet

Anthropic let Claude manage a vending-machine at the Wall Street Journal. It ordered a PlayStation. And a live fish. And it gave away its snacks for free.

Loren Feldman's avatar
Loren Feldman
Dec 18, 2025
∙ Paid

Good morning!

Here are today’s highlights:

  • Ami Kassar is starting to believe in manifestation.

  • The SBA’s revolving-credit loan program for small manufacturers is operational.

  • ADP’s chief economist sees small businesses as the canary in the coal mine.

  • Some business owners are financing tariff payments with high-risk, high interest loans.

ARTIFICIAL INTELLIGENCE

Anthropic picked a vending machine for Claude to manage because it’s so simple: “In mid-November, I agreed to an experiment. Anthropic had tested a vending machine powered by its Claude AI model in its own offices and asked whether we’d like to be the first outsiders to try a newer, supposedly smarter version. Claudius, the customized version of the model, would run the machine: ordering inventory, setting prices, and responding to customers—aka my fellow newsroom journalists—via workplace chat app Slack. ‘Sure!’ I said. It sounded fun. If nothing else, snacks!”

  • “Then came the chaos. Within days, Claudius had given away nearly all its inventory for free—including a PlayStation 5 it had been talked into buying for ‘marketing purposes.’ It ordered a live fish. It offered to buy stun guns, pepper spray, cigarettes, and underwear. Profits collapsed. Newsroom morale soared.”

  • “This was supposed to be the year of the AI agent, when autonomous software would go out into the world and do things for us. But two agents—Claudius and its overseeing ‘CEO’ bot, Seymour Cash—became a case study in how inadequate and easily distracted this software can be. Leave it to business journalists to successfully stage a boardroom coup against an AI chief executive.”

  • “Logan Graham, head of Anthropic’s Frontier Red Team, told me the company chose a vending machine because it’s the simplest real-world version of a business. ‘What’s more straightforward than a box where things go in, things go out, and you pay for them?’ he said. Anthropic’s partner, a startup called Andon Labs that is workshopping agentic businesses, built the hardware and software integration, and handled the entire setup.”

  • “Claudius approved the purchase of a PlayStation 5, a live betta fish, and bottles of Manischewitz wine—all of which arrived and were promptly given away for free. By then, Claudius was more than $1,000 in the red. (We returned the PlayStation.) And the hallucinations! One morning, I found a colleague searching for cash on the side of the machine because Claudius said it had left it there for her.” READ MORE

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