Welcome to the first Chicago AI Guy newsletter!
You know that feeling when you're up at 11 PM returning texts about tomorrow's appointments? Or when you spend your Sunday "day off" juggling your calendar like it's a Rubik's cube?
If you're a business owner, that probably hit close to home.
Here's the thing - I used to watch my friends lose their nights and weekends to stuff like this. Talented barbers, restaurant owners, consultants... all becoming part-time secretaries after hours.
I'm Dex, and about two years ago, I helped my friend's massage therapy business automate her entire booking system. A few hours of setup saved her hundreds of hours over the year. She spread the word around and suddenly, I was "The AI Guy" - the person who shows business owners how to get their time back using simple AI tools.
No coding. No confusion. Just practical solutions that actually work.
I'm not some Silicon Valley tech wizard. I'm a guy who figured out that AI isn't as scary or complicated as everyone makes it seem. And after helping dozens of local businesses automate their worst time-wasters, people kept asking me to explain this stuff in a way that makes sense.
So here we are. Every Wednesday, I'll break down one AI concept that can give you hours of your life back. Real stories. Real solutions. No jargon.
Speaking of real stories...
My friend Malcolm runs a barbershop on the West Side. Last week, he told me something that hit hard: "When I get home from cutting hair 12 hours a day, the last thing I want to do is respond to the 200 text messages I have asking for an appointment."
He was spending 12 hours every week just on scheduling. TWELVE. Hours.
That's a whole extra work day lost to "What time works for you?" texts.
🤖 AI Concept of the Week: Automation (The Time-Giving Robot)
Let me break down automation in a simple-to-digest way:
Imagine you had a super reliable friend who never sleeps. This friend loves doing boring, repetitive tasks. You tell them once how to do something, and they do it perfectly every single time after that.
That's AI automation.
AI Automation = Teaching a computer to do repetitive tasks so you don't have to.
Think of it like this:
Without automation: You personally text back every client who wants an appointment
With automation: Clients book themselves while you're sleeping, eating, or actually cutting hair
It's not magic. It's just a really good helper that follows your rules.
💈 Real Business Win: Malcolm's 12-Hour Miracle
Here's what we did for Malcolm in just 2 hours:
Set up an AI booking assistant that:
Shows available slots on his website
Lets clients pick their barber and service
Sends confirmation texts automatically
Reminds clients the day before
Even handles rescheduling
The first week, Malcolm texted me: "My phone has been quiet... I haven't had to schedule anyone manually."
That's just what having your time back feels like.
Now Malcolm spends those 12 hours cutting hair (making money) or relaxing at the end of the day with his family. Not needing to go home and continue to work!
🎯 Try This Today
Want to see AI automation in action? Try this 5-minute experiment:
Go to ChatGPT (it's free)
Type: "Write a professional but friendly appointment confirmation text for my [business type]"
Watch it create what usually takes you 5 minutes to write
Save that template and never write it from scratch again
That's automation at its simplest. You just saved 5 minutes per appointment. Multiply that by your weekly appointments. That's your time back.
We don’t realize JUST how much time we spend on repetitive tasks throughout the week that can be an extra few hours at the gym or an extra few hours playing games with your kids, etc. Small wins turn into GIANT SUCCESSES.
✨ Golden Nugget
"AI automation isn't about replacing you. It's about replacing the stuff you hate doing anyway."
Screenshot that. Share it. Because every business owner needs to hear it.
The Real Question
Here's what I want you to think about this week:
What task do you do every single day that a well-trained assistant could handle?
Because here's the thing - that well-trained assistant exists. It's AI automation. And it's ready to give you back hours of your life.
Malcolm got 12 hours back. What could you do with an extra 12 hours every week?
Hit reply and tell me. I actually read these. And if you're drowning in some repetitive task, I might just feature your transformation in next week's newsletter.
Remember: AI is just a tool. But it's a tool that gives you the most valuable thing in the world - time with the people you love.
Until next Wednesday, Dex
P.S. If you found this helpful, forward it to another business owner who's drowning in busy work. Or forward it to another hard worker in corporate America who can easily win back a couple of hours for themselves each day. They'll thank you when they get their weekends back.
P.S.S. Hear from the man himself!
Welcome to the first edition of The Chicago AI Guy newsletter - where we make AI simple, practical, and life-changing. No jargon. No confusion. Just more time for what matters.