The Chicago AI Guy

The 10-Minute Skill That Changes Everything

The difference between "meh" and WOW THAT'S AMAZING!

Oct 2 • 

Dex

September 2025

The 5 AI Tools That Ran My Business While I Was in Greece (Plus That Fish Story)

The exact 5-tool system I promised

Sep 25 • 

Dex

𝐓𝐡𝐞 𝐂𝐡𝐢𝐜𝐚𝐠𝐨 𝐀𝐈 𝐆𝐮𝐲 𝐀𝐈 𝐓𝐢𝐩 𝐨𝐟 𝐭𝐡𝐞 𝐃𝐚𝐲: 𝐓𝐡𝐞 𝟐-𝐌𝐢𝐧𝐮𝐭𝐞 𝐂𝐮𝐬𝐭𝐨𝐦𝐞𝐫 𝐅𝐀𝐐 𝐆𝐞𝐧𝐞𝐫𝐚𝐭𝐨𝐫

Create an auto-responder in your DMs (EXPERT MODE)

Sep 18 • 

Dex

The Newsletter That Almost Didn't Happen (Because I Was Eating Feta in Greece)

Where I've been for 2 weeks (and the AI lesson hidden in Greek islands)

Sep 17 • 

Dex

August 2025

Why Your Brain Won't Let You Stop Checking Email (And The 6-Minute Fix)

The dopamine truth about email addiction and the 3-check-per-day solution

Aug 28 • 

Dex

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5 ChatGPT Prompts That Just Gave You Back Your Tuesday Nights

How Business Owners Are Saving 15 Hours Weekly With These Advanced Prompts

Aug 21 • 

Dex

1

3 AI Automations That Give You Your Life Back Right Now

How to reclaim 5+ hours every week without working harder

Aug 14 • 

Dex

2

The Cat Olympics AI Tool That's Saving Business Owners 15 Hours a Week

I've sat and read and watched about Cats this week more than I'd like to admit.

Aug 7 • 

Dex

2

July 2025

The Chicago AI Guy Newsletter: Issue #1

Your Weekly Guide to Getting Time Back with AI

Jul 30 • 

Dex

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