The Chicago AI Guy
DexChicagoans need one of our own talking about AI in a way that actually makes sense. That's me. Chicago's AI newsletter. I break down what's actually useful and skip the rest. Tools, tips, and straight talk, every week.
| Platform |  | Pricing | Only free issues | Publishes | Weekly |
|---|---|---|---|---|---|
| Issues | 19 | Founded | 10 months ago | Last Issue | 3 months ago |
| Active | |||||
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thechicagoaiguy.comLatest Issues
Sonnet 4.6 just dropped. Here's why you should care (even if you don't know what that means)
Claude Sonnet 4.6 Just Dropped. Here’s What That Actually Means for You.
Every few months, one of the big AI companies releases a new model and the tech world loses its mind for about 48 hours.
The Chicago AI Guy is a reader-supported pub...
Inside Moltbook: Where 1.5M AI Agents Built Their Own Religion
The Week AI Built Its Own Society (And Started a Religion)
Last week, something happened that sounds like the opening scene of a sci-fi movie.
1,500,000 AI agents created their own social network. Then they invented a religion. Formed a...
The AI "Experts" Are Cheating (And You Have The Advantage)
The biggest AI conference in the world just got caught with its pants down.
On November 27, 2025, researchers at the International Conference on Learning Representations (ICLR) discovered something embarrassing: 21% of the peer reviews sub...
I'm Getting The AI Ick
I’m tired.
Not “I need a vacation” tired. Not “long week” tired.
I’m tired of the AI space.
And I know that’s weird coming from the guy who writes an AI newsletter every week. But hear me out.
The Grifter Takeover
The AI space is exhau...
7 AI Startups Burned Through Over Half a Billion Dollars and Failed. This 23-Year-Old Spent $20 and Won.
770 people showed up to work at Builder.ai on a Tuesday morning in May.
By Tuesday afternoon, they were all unemployed.
Builder.ai, a company valued at $1.5 billion, backed by Microsoft and the government of Qatar, filed for bankruptcy. 7...
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Authors
The writers behind this newsletter.
I'm a human being, and I am flawed. I try my best to show up every single day for what matters most to me. This is one of those things. Live in Chicago, do cool AI Stuff. Follow along if it pleases you.
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