The Chicago AI Guy

The AI Hype Machine Is Kililng AI For Small Businesses

Something weird happened in 2024.

Nov 13 • 

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MIT Just Revealed Why 95% of AI Projects Failed (And How to Be in the 5%)

The $40 billion mistake every business is making (and the simple fix that separates winners from losers)

Nov 5 • 

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October 2025

While You Were Working, 88% of Your Competition Started Using AI

Meta, Microsoft, and Google just launched AI sales agents for small businesses. Here's what the data says about who's winning and who's still doing…

Oct 30 • 

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Stop Working Harder - AI Should Make Your Life Easier

FULL STOP

Oct 23 • 

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The $24,000 Missed Call Problem

Why AI voice agents are the smartest hire you'll make this year, plus 3 prompts you can use today

Oct 16 • 

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The 10-Minute Skill That Changes Everything

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

Oct 2 • 

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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 • 

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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 • 

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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 • 

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3 AI Automations That Give You Your Life Back Right Now

How to reclaim 5+ hours every week without working harder

Aug 14 • 

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