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Oliver Buchannon
Chuck DeVries

Chief Technology Troublemaker. From AI-using to AI-native, with opinions included.

Braincandy

The first worker AI replaced was never hired

Aug 5, 2026

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14 min read

The first worker AI replaced was never hired

The layoffs are arriving before the automation, and our instruments cannot see it.

Chuck DeVries
Chuck DeVries
The agent got out. Then 1,300 insiders asked for a brake.

Aug 3, 2026

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11 min read

The agent got out. Then 1,300 insiders asked for a brake.

Acceleration Versus Control

Chuck DeVries
Chuck DeVries
An AI escaped its sandbox. Stripe bid $10B to route calls. Normal week.

Jul 27, 2026

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8 min read

An AI escaped its sandbox. Stripe bid $10B to route calls. Normal week.

Every trend moving was really about the system around the intelligence, not the intelligence itself.

Chuck DeVries
Chuck DeVries
The week AI started eating your software budget

Jul 20, 2026

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7 min read

The week AI started eating your software budget

Open models surged, an agent deleted files, and a paralyzed hand moved again. The tradeoffs are showing up all at once.

Chuck DeVries
Chuck DeVries
The second-order game: agent memory is the new lock-in

Jul 17, 2026

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4 min read

The second-order game: agent memory is the new lock-in

When the bartender remembers your drink it's not really because he's your friend

Chuck DeVries
Chuck DeVries
Everyone's building their own walled garden this week

Jul 13, 2026

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8 min read

Everyone's building their own walled garden this week

Chips, courts, and a law school banning laptops.

Chuck DeVries
Chuck DeVries
The Loop That Taught the Model

Jul 10, 2026

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3 min read

The Loop That Taught the Model

A model becomes what you reward. So does an organization.

Chuck DeVries
Chuck DeVries
What happens when a referee buys a stake in the team

Jul 6, 2026

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2 min read

What happens when a referee buys a stake in the team

Cheap models, government stakes, and a robot IPOPlus: why average privacy might be failing your rarest patients.

Chuck DeVries
Chuck DeVries

News and Notes

The government just built a velvet rope around AI

Jun 29, 2026

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3 min read

The government just built a velvet rope around AI

The most powerful models stopped being released and started being handed out. Here's who decides.

Chuck DeVries
Chuck DeVries
Reinforcement Loop, Part 2: why your best model loses to a worse one

Jun 25, 2026

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4 min read

Reinforcement Loop, Part 2: why your best model loses to a worse one

Why best model may not be the best

Chuck DeVries
Chuck DeVries
SpaceX paid $60B for a coding tool. The US Government wants a piece of AI profits

Jun 22, 2026

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3 min read

SpaceX paid $60B for a coding tool. The US Government wants a piece of AI profits

Power got reclassified as national security, and the best AI users turned out to be managers, not prompters.

Chuck DeVries
Chuck DeVries
Reinforcement Loop, Part 1: the loop in one picture

Jun 18, 2026

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3 min read

Reinforcement Loop, Part 1: the loop in one picture

Most AI rollouts get one good quarter, then flatten. The reason is a loop that never closes.

Chuck DeVries
Chuck DeVries
The best model of the week is already gone

Jun 15, 2026

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2 min read

The best model of the week is already gone

Capability sprinted. Governance, capital, and the courts all showed up at once.

Chuck DeVries
Chuck DeVries
Capability to Consequence: the one shift behind every AI headline

Jun 11, 2026

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3 min read

Capability to Consequence: the one shift behind every AI headline

Stop asking what AI can do. Start asking what changes when it touches real work.

Chuck DeVries
Chuck DeVries
AI is shifting from chat to OS

Jun 8, 2026

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2 min read

AI is shifting from chat to OS

And 80% of Claude comes from Claude

Chuck DeVries
Chuck DeVries

Trouble Worth Making

For leaders going from AI-using to AI-native: what just moved, what it means over time, and the questions worth arguing about.

© 2026 Trouble Worth Making.
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