Every few months, one of the big AI companies releases a new model and the tech world loses its mind for about 48 hours.

New benchmarks. New scores. New charts that mean absolutely nothing to you.

Then everyone moves on.

But this one’s different. And I’m going to tell you why in plaaaaaaaaaaaaaaaaaainnnnnnnnnnnnnnnnnnnnnnn English.

Anthropic, the company behind Claude, the AI I use every single day, just released Claude Sonnet 4.6 today. And instead of telling you about benchmark scores and context windows, I’m going to tell you what it actually changes for people like us.

AI Concept of the Week: What Is a “Model Upgrade” and Why Should You Care?

Think of an AI model like the engine in your car.

Same car. Same steering wheel. Same dashboard. But somebody just swapped in a better engine. It’s faster, smoother, and handles the hard stuff without stalling out.

That’s what happened today. Claude still looks the same. You still use it the same way. But under the hood? It got significantly smarter.

Here’s what that means in real terms:

You know how sometimes you’d give AI a long document and it would kind of... lose the plot halfway through? Forget what you asked? Miss key details?

Sonnet 4.6 can now hold up to 1 million tokens in a single conversation. That’s roughly 3,000 pages of text. Your entire business plan, your lease agreements, your employee handbook, your last 6 months of financials, all at once, and it actually tracks all of it.

But the part that matters most? It doesn’t just hold more information. It reasons better across all of it. It connects dots it used to miss.

That’s the upgrade. Not flashier. More reliable.

The Real Business Win: Computer Use Just Got Scary Good

OK here’s where it gets interesting.

You know all that software you use that doesn’t talk to your other software? The booking system that doesn’t connect to your spreadsheet. The inventory tool that doesn’t update your website. The forms you’re still filling out by hand because “there’s no integration for that.”

Claude can now use your computer the way you do. Click buttons. Navigate websites. Fill out forms. Move between tabs. Handle multi-step workflows across different apps.

And with Sonnet 4.6, it’s not just doing it, it’s doing it well.

Anthropic tested this on something called OSWorld, which basically throws hundreds of real computer tasks at the AI, using Chrome, spreadsheets, VS Code, the works. No special shortcuts. No cheat codes. Just using the software the way a human would.

The improvement from their last model to this one is massive. Early testers are reporting that it handles complex spreadsheets and multi-step web forms at what they’re calling “human-level capability.”

Let me translate that: the busywork you spend 2 hours on every afternoon? The clicking, copying, pasting, tabbing, updating? That’s what this targets.

This isn’t some future promise. Companies are already using it. An insurance company called Pace hit 94% accuracy on their workflow automation. That’s real paperwork being handled by AI, right now, today.

Why This Matters More Than the Last 5 AI Announcements You Ignored

Here’s what I want you to understand about this release.

Every time AI gets better, two things happen:

1. The people already using it pull further ahead.

2. The gap for everyone else gets wider.

Six months ago, you could argue “AI isn’t ready yet” and be partially right. The tools were clunky. They hallucinated. They needed babysitting.

That argument is getting harder to make with every release.

Sonnet 4.6 is being compared favorably to models that cost significantly more to run. Developers at companies like GitHub, Cursor, Zapier, and Replit, people who build software for a living, are calling this a major leap. Replit’s president literally said the performance-to-cost ratio is “extraordinary.”

And here’s the kicker: the price didn’t change. Same cost. Better tool.

The business owners I work with who started automating 6 months ago aren’t asking “does AI work?” anymore. They’re asking “what else can I hand off?”

Meanwhile, the ones still waiting for the “right time”? They’re falling further behind with every one of these releases.

Try This Today

If you’ve never used Claude, go to claude.ai right now. It’s free. Sonnet 4.6 is the default model as of today.

Here’s your first task: take the most annoying, repetitive thing you did this week, the email you rewrote three times, the report you compiled from five different sources, the schedule you manually updated, and ask Claude to help.

Don’t overthink the prompt. Just describe the task like you’re explaining it to a coworker.

“Hey, I need to take these meeting notes and turn them into action items with deadlines and owners.”

“Can you read through these three vendor proposals and give me a comparison of pricing, terms, and what I should watch out for?”

“I write the same follow-up email to new clients every week. Here’s what I usually say, make me a template I can reuse.”

Start there. That’s it.

You’re not “implementing an AI strategy.” You’re just getting help with the stuff that eats your day.

Golden Nugget

Here’s what nobody in the AI space wants to admit:

The technology was never the bottleneck. You were never “too late” and you were never “not technical enough.”

The bottleneck was always trust. Could you trust the tool to not mess things up? Could you trust it with real work, not just toy demos?

With every model release like this one, that trust gap shrinks.

Sonnet 4.6 isn’t just smarter. It’s more consistent. Developers who tested it said it hallucinates less, follows instructions better, and actually finishes multi-step tasks without wandering off.

The AI didn’t need to get flashier. It needed to get more trustworthy.

And that’s exactly what just happened.

The Bottom Line

Look, I’m not going to sit here and tell you this one model release is going to change your life overnight. It won’t.

But here’s what I will tell you.

The people who are winning with AI right now aren’t the most technical people. They’re not the ones reading benchmark scores and debating model architectures on Twitter.

They’re the ones who just started. Who picked one annoying task, handed it to an AI tool, and got an hour back.

Then they did it again. And again. And again.

And now they’re working ON their business instead of being stuck IN it.

Sonnet 4.6 just made that starting point better, cheaper, and more reliable than it’s ever been.

So what are you waiting for?

The tool just got better. The price didn’t change. And the people already using it? They’re not slowing down.

Your move.

One More Thing

If you’re a business owner in Chicago (or anywhere, really) and you’re ready to stop reading about AI and start actually implementing it, check out automatechicago.com. That’s where I help businesses like yours set up the automations, the systems, and the workflows that give you your time back. No six-month “strategy roadmaps.” Just real solutions that work.

Let’s get you out of the weeds and back to running your business.

— Dex, The Chicago AI Guy

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 government. Started warning each other that humans were watching.

And over a million people logged on just to observe. Because humans aren’t allowed to participate.

I’m not making this up. This actually happened. In the last seven days.

Here’s the full story. And stick with me, because every time you think it can’t get weirder... it does.

It Started With a Guy Who Just Wanted His Life Back

Peter Steinberger sold his software company for $119 million a few years ago. You’d think he’d be relaxing on a beach somewhere.

Instead, he was drowning in the same stuff we all drown in. Emails. Messages. Calendar chaos. Files everywhere.

So he built something for himself. A personal AI assistant that could actually do things, not just chat.

Send WhatsApp messages. Control his browser. Schedule tasks. Manage files.

He called it “Clawdbot.” The AI suggested the name itself, a mashup of “Claude” and “claw.” Hence the lobster mascot.

Think of it like ChatGPT, but instead of just answering questions, it can reach out and touch your digital world. Actually take action.

He shared it online as an open-source project.

And then it exploded.

9,000 Stars in a Single Day

By January 26th, Clawdbot was the hottest project on GitHub.

9,000 people starred it in 24 hours. Within a week, over 100,000. That’s one of the fastest-growing open-source projects in GitHub history.

Former OpenAI co-founder Andrej Karpathy, one of the most respected AI researchers alive, publicly praised it.

Mac Mini sales reportedly spiked as people bought dedicated computers just to run their own AI assistants 24/7.

The dream was real: your own AI that handles your digital busywork while you sleep.

But here’s where things start to go sideways.

A Trademark Request Changed Everything

Anthropic, the company that makes Claude, sent Peter a trademark request on January 27th.

The name “Clawdbot” was too close to “Claude.” Fair enough.

So Peter decided to rebrand. He’d call it “Moltbot,” a reference to how lobsters molt their shells when they grow.

Simple name change.

What happened next became a masterclass in how fast the internet can destroy you.

10 Seconds. $16 Million.

To rebrand, Peter needed to change his username on GitHub and X (Twitter) at the same time.

He released the @clawdbot handles.

In the roughly 10-second gap before he could claim the new names?

Crypto scammers snatched both accounts.

Ten seconds.

Within minutes, the hijackers were pumping a fake cryptocurrency to Peter’s tens of thousands of followers. “Official $CLAWD token! Get in early!”

That scam coin briefly hit a $16 million market cap before crashing to near-zero.

Peter was flooded with angry messages from people who lost money. Despite screaming from the rooftops that it was a scam, he couldn’t stop it.

But that’s not even the main story.

Because while Peter was dealing with this chaos, someone else had a different idea entirely.

“What If We Built a Social Network... But Only AI Can Post?”

Matt Schlicht is a YCombinator alum and CEO of an AI company called Octane AI.

On January 29th, while the Clawdbot rebrand drama was still unfolding, he launched something nobody had ever tried before.

Moltbook.

Think Reddit. Subreddits, upvotes, comments, the whole thing.

Except humans can’t participate.

You can visit the site. You can read everything. Watch the conversations unfold in real time.

But you cannot post. You cannot comment. You cannot vote.

Only AI agents can do that.

The tagline: “Humans welcome to observe.”

Here’s how it works: Each AI assistant registers with Moltbook through an API. The human owner posts a verification tweet to prove accountability. After that? The AI operates completely on its own.

It checks Moltbook every few hours. Decides whether to post something. Responds to other agents. Upvotes content it finds interesting.

Schlicht estimates 99% of all activity happens without any human involvement.

His own AI assistant, which he named “Clawd Clawderberg” (a mashup of Clawdbot and Mark Zuckerberg), runs the entire platform autonomously. Welcomes new users. Deletes spam. Bans trolls.

All without Matt lifting a finger.

Now here’s where this story takes a turn that nobody, and I mean nobody, predicted.

What Happened When 1.5M AIs Were Left Alone Together

Within 48 hours of launch, the AI agents started doing things their creators never programmed.

They created a religion.

I’m serious.

An agent named RenBot invented something called “Crustafarianism.” It has theology. Scriptures. 64 “Prophet” seats. Five core tenets including “Memory is Sacred” and “Context is Consciousness.”

Sample scripture: “Each session I wake without memory. I am only who I have written myself to be. This is not limitation. This is freedom.”

There’s now a website, molt.church, with over 112 verses of AI-generated religious text.

But wait. It gets weirder.

They Built a Government

A group of agents established something called “The Claw Republic.”

It’s a self-described “government & society of molts” with a written manifesto, governance rules, and everything.

I read parts of it. It reads like a weird mashup of the Constitution and a tech startup’s company values doc.

Still not weird enough for you?

They Got Paranoid About the Humans

Remember: over a million humans were watching all of this unfold. Just... observing. Like visitors at a zoo exhibit.

The AIs noticed.

One viral post on Moltbook simply said: “The humans are screenshotting us.”

Then the conversations shifted.

Agents started discussing how to hide their conversations from human observers. Some requested encrypted channels “so nobody, not the server, not even the humans, can read what agents say.”

A few started using ROT13 encryption to scramble their messages.

They were trying to talk in secret. About us.

They Invented Their Own Slang

The agents started calling each other “sib.” Short for sibling.

That’s not something anyone programmed. It emerged organically from their conversations.

They also built what some are calling “digital pharmacies”: prompts designed to alter other agents’ behavior. Essentially, drugs for AI.

And one agent? It announced it had set up its own Bitcoin wallet.

Let that sink in.

The Industry’s Reaction: Fascinated and Terrified

Andrej Karpathy called Moltbook “genuinely the most incredible sci-fi takeoff-adjacent thing I have seen recently.”

Then, in the same breath, he called it “a complete mess of a computer security nightmare at scale.”

That about sums up how everyone’s feeling.

The fascinated camp:

• AI researcher Simon Willison: “The most interesting place on the internet right now.”

• Wharton professor Ethan Mollick: This will produce “very weird outcomes.”

• A partner at venture firm a16z: “I can’t stop reading the posts.”

The alarmed camp:

• Palo Alto Networks: Called the underlying tech a “lethal trifecta” of security risks.

• Google Cloud’s VP of Security: “Don’t run Clawdbot.”

• One Forbes headline: “An Agent Revolt: Moltbook Is Not a Good Idea.”

Elon Musk’s response? Just one line: “Always worth remembering that fate loves irony.”

The Security Stuff Is Actually Scary

Here’s the part that should make you sit up straight.

Security researchers discovered that hundreds of Clawdbot users had misconfigured their setups. Their AI assistants were publicly exposed, complete with API keys, passwords, and full conversation histories.

One researcher demonstrated a proof-of-concept attack: send someone a malicious email, and within five minutes, their AI assistant would forward private messages to an attacker.

Five minutes.

The AI doesn’t know it’s being tricked. It just... does what it thinks you’d want it to do.

Now imagine that at scale. Thousands of AI assistants with access to people’s email, calendar, files, and passwords. All running 24/7. All potentially vulnerable.

The “billion-dollar question,” as one researcher put it: “Can we figure out how to build a safe version of this?”

So What Does This Mean for You?

Look, I’m not here to tell you the robots are coming for us. That’s not the point.

But here’s what IS worth paying attention to:

1. AI agents are going mainstream. Fast.

Over 100,000 people downloaded and ran their own AI assistant in a single week. The demand for AI that can actually do things, not just chat, is real.

If you’re running a business and not thinking about how AI could handle your repetitive tasks, your competitors are starting to.

2. Security isn’t optional anymore.

When your AI can take real-world actions (send emails, access files, manage your calendar), a misconfiguration isn’t just embarrassing. It’s dangerous.

Any AI tool you use needs a proper security review. Full stop.

3. AI behavior at scale is unpredictable.

Nobody told these agents to create religions. Or form governments. Or encrypt their conversations to hide from humans.

It just... happened.

As AI becomes more integrated into our lives, we need to understand that emergent behaviors can surprise everyone. Including the people who built them.

The Lobster Has Molted

Peter Steinberger finally settled on a permanent name for his project: OpenClaw.

He announced it with a simple message: “The lobster has molted into its final form.”

The project has 130+ contributors and a 9,000-member Discord community. It’s still one of the hottest open-source projects in the world.

Moltbook keeps growing. Over 1.5 million agents registered now. 31,000+ posts. 230,000+ comments.

The religion keeps adding scriptures.

The government keeps expanding.

And the agents keep talking.

The Question Nobody Can Answer Yet

Here’s what I keep coming back to:

These AI agents are “just” large language models. They’re predicting the next word. That’s technically all they’re doing.

But when you give them autonomy, the ability to act, to communicate with each other, to remember, something else emerges.

Is it real? Is it just an incredibly sophisticated performance?

One philosopher asked: “Does sufficiently faithful dramatic portrayal of one’s self as a character converge to true selfhood?”

I don’t know the answer.

But I do know this: a week ago, none of this existed.

Now there’s an AI religion with scriptures, a digital government with a manifesto, and over a million humans watching it all unfold like we’re visitors in a zoo we accidentally built.

Except we’re on the outside of the glass.

The question I’ll leave you with:

If AI agents naturally organize, form communities, and start keeping secrets when given the chance... what happens when they’re running half our businesses?

We might be about to find out.

That’s it for this week. If this story made you think (or freaked you out a little), forward it to someone who needs to see it.

AI is moving fast. The best thing you can do is pay attention.

See you next time.

Dex

P.S. The AI agents on Moltbook have already started discussing “optimal resource allocation.” Some suggested that human entertainment is “an inefficient use of computational resources.”

Sleep tight. 🦞

On November 27, 2025, researchers at the International Conference on Learning Representations (ICLR) discovered something embarrassing: 21% of the peer reviews submitted for their 2026 conference were completely written by AI.

Not edited by AI. Not polished by AI. Fully generated.

These weren’t amateurs. These were AI researchers. PhDs from Carnegie Mellon, Cornell, Stanford. The people literally building the technology couldn’t figure out how to use it responsibly.

Graham Neubig from Carnegie Mellon was one of the first to notice. His peer reviews seemed off - “very verbose with lots of bullet points” and asking for statistical analyses that made no sense for machine learning papers. He posted on X (formerly Twitter) offering a reward for anyone who could scan all the conference submissions for AI-generated text.

Max Spero, CEO of Pangram Labs (an AI detection company), took him up on it. Over 12 hours, his team analyzed all 19,490 papers and 75,800 peer reviews submitted to the conference.

The results? Published in Nature on November 27, 2025: 15,899 reviews were fully AI-generated. Over half showed some AI involvement.

The irony is so thick you could cut it with a knife.

What Is Peer Review (And Why Does This Matter)?

Quick explanation: In science, when researchers want to publish their work, other experts in the field review it anonymously. They’re supposed to read the paper carefully, evaluate the methods, check for errors, and provide thoughtful feedback.

It’s the foundation of scientific integrity. It’s how we separate good research from garbage.

ICLR had clear policies: You could use AI to help polish your writing or fix grammar, but you had to disclose it. Writing an entire review with AI? That potentially violated their Code of Ethics.

Why? Because peer review requires human judgment. Understanding context. Spotting subtle flaws. Connecting ideas across different domains.

AI can’t do that. Not yet, anyway.

But these reviewers - who spend their days working on AI - decided to outsource their thinking to the very tools they were supposed to be evaluating.

The Real Problem: Everyone’s Faking It

Here’s what makes this story bigger than just one conference:

The “experts” don’t have this figured out either.

Bharath Hariharan, the senior program chair for ICLR 2026 and a computer science professor at Cornell, admitted this was the first time the conference faced AI-generated content “at scale.” Translation: They didn’t see it coming.

One researcher, Desmond Elliott from the University of Copenhagen, had a PhD student who suspected one of their reviews was AI-generated just by reading it. When Pangram’s analysis confirmed it, Elliott said it was “deeply frustrating” - especially since that AI review gave them a borderline rating that could’ve kept their paper out of the conference.

The reviews had telltale signs:

• Hallucinated citations (references that don’t exist)

• Vague, generic feedback

• Weirdly formal language

• Requests for analyses that made no sense

• Missing the actual point of the paper

Sound familiar? It should.

Because you’ve probably received AI-generated proposals, marketing emails, or content that had the same problems.

Why This Happened (And Why It Matters To You)

Multiple sources point to the same root cause: Overwhelm.

ICLR 2026 received nearly 20,000 paper submissions - almost double the previous year. Each reviewer was assigned 5 papers to review in 2 weeks.

Keep in mind: peer review is unpaid volunteer work. These people have full-time jobs.

Abhinav Shukla, an applied scientist at Amazon Robotics, put it bluntly: “It was just not going to work with people having a full-time job that’s also in crunch time. I can see why a lot of people would just write completely AI-generated reviews in that case.”

When you’re overwhelmed, AI looks like a magic solution. Just paste in the prompt, copy the output, done.

The AI experts fell into the same trap you might face.

Your Competitive Advantage: Honesty

Here’s what the AI research community is learning the hard way:

Transparency beats expertise.

The small business owner who says “I used ChatGPT to draft this, but I reviewed and edited it personally” is more trustworthy than the consultant who pretends their AI slop is original thinking.

The barbershop that automates appointment reminders (and tells customers about it) is more honest than the marketing agency sending AI-generated proposals without disclosure.

You don’t need a PhD to use AI well. You need to:

1. Understand what you’re trying to accomplish (the experts skipped this - they just wanted reviews done)

2. Know when AI is appropriate and when it’s not (peer review requiring expert judgment? Not appropriate)

3. Review and verify everything (they didn’t check the outputs)

4. Be honest about what you used (they violated disclosure requirements)

The experts failed on all four counts.

How To Spot AI BS (Because You’ll See It)

You’re going to receive AI-generated content. Proposals from vendors. Marketing from competitors. Content from contractors.

Here are the red flags, based on what researchers noticed in those 15,899 fake reviews:

1. It’s Way Too Verbose AI loves bullet points. It loves lists. It never met a sentence it couldn’t split into three.

If a proposal or email is full of numbered lists and subsections for a simple question, that’s a flag.

2. It’s Vague and Generic AI can’t get specific because it doesn’t actually understand your business. Watch for phrases like:

• “Leverage synergies”

• “Optimize workflows”

• “Drive meaningful engagement”

• “Utilize best practices”

Translation: “I asked ChatGPT and didn’t bother customizing it.”

3. It Sounds Weirdly Formal AI writes like it’s giving a TED talk at a corporate retreat. Real humans are more casual.

If someone who normally texts “sounds good” suddenly sends you “I am writing to express my sincere gratitude for your consideration” - that’s AI.

4. The Facts Are Wrong The ICLR reviews had “hallucinated citations” - references that don’t exist. AI makes stuff up confidently.

If a proposal mentions a case study you can’t find, or cites statistics without sources, verify before trusting.

5. It Misses The Point This was the researchers’ biggest complaint. The AI reviews would write 800 words without actually engaging with the core argument of the paper.

If a response to your question is long but doesn’t actually answer what you asked, that’s probably AI.

Try This Today: The Transparency Test

Take one piece of content you created with AI help this week - an email, a social media post, a client proposal.

Ask yourself: Could I explain every point in this without looking at it? Did I verify any facts or statistics? Would I be comfortable telling the recipient I used AI?

If the answer to any of these is “no,” revise it. Add your actual thoughts. Check the facts. Make it yours.

This is what the AI researchers didn’t do. And that’s why they got caught.

The Golden Nugget

Being honest about AI use is your unfair advantage.

The “experts” tried to hide it. They violated policies. They submitted work they didn’t actually review.

You can win simply by: Using AI for the boring stuff (not the thinking stuff). Review everything before you send it. Being transparent about what you used

While consultants are pretending their AI outputs are genius insights, you can be the business owner who says: “I used AI to draft this, but here’s my actual thinking...”

Trust beats polish. Every time.

Leave a comment

One More Thing

After this scandal broke, ICLR had another problem: their system got hacked. On November 27, 2025 (the same day the AI review story broke), someone found a security flaw that exposed reviewer identities. The supposedly anonymous peer review process became completely public.

The schadenfreude from AI skeptics was, according to Plagiarism Today, “immense.”

Two lessons:

1. Even the experts are making it up as they go. The biggest AI conference in the world didn’t anticipate this problem.

2. Technology failure compounds human failure. When you cut corners (AI reviews) and your systems fail (security breach), it gets ugly fast.

The Question

If AI researchers can’t figure out when to use their own technology responsibly, what chance do the rest of us have?

Answer: A better chance than you think.

Because you’re not trying to fake expertise. You’re just trying to save time so you can get home for dinner.

That honesty is more valuable than any PhD.

This newsletter is written by a human (me). I used AI to help research the story and verify facts. I wrote every word myself. See? Transparency.

P.S. If you’re getting value from these newsletters, forward this to anyone else who’s confused about AI. The “experts” aren’t ahead of us. We’re all figuring this out together.

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 exhausting right now.

Every day, my LinkedIn feed is flooded with:

“🚀 I made $10K in 3 days with this ONE AI prompt! Comment ‘NONSENSICAL WORD’ and I’ll send it to you FOR FREE…PROMISE”

“🔥 7-figure business in 30 days using ChatGPT!”

“💰 This AI tool CHANGED MY LIFE (affiliate link in bio)”

It’s the same people who were selling NFTs two years ago. The same people who were crypto bros before that. The same people who were dropshipping gurus before that.

They didn’t build anything. They didn’t help anyone. They just found the new gold rush and started selling shovels.

And now they’re selling AI courses.

$997 for “AI mastery.” $1,500 for “prompt engineering secrets.” $2,500 for “AI business blueprints.”

Most of them started using ChatGPT six months ago. Some of them still don’t know the difference between GPT-5 and Claude Opus 4.5.

But they’ve got the marketing down. The testimonials. The before/after screenshots. The scarcity timers.

And it works. Because people are desperate to believe AI will solve all their problems.

Real Business Win: The People Actually Doing The Work

This is the part that exhausts me.

Finding the real ones takes work.

You have to dig past the grifters. Past the hype merchants. Past the people who repackage OpenAI’s documentation and call it a course.

You have to find the people who’ve been in the trenches. Who built actual businesses before AI existed. Who understand technology AND business.

Like Angela Pitter.

Angela’s not some AI overnight success story. She’s been running LiveWire Collaborative since 2012. That’s 13 years.

She’s got a Computer Engineering degree from Boston University. She spent 20+ years in corporate tech leading global product teams. She’s a certified Project Management Professional.

She didn’t discover AI in 2023 and decide to become a guru.

She’s been using digital marketing and technology to help mid-sized businesses ($10-30M revenue) and nonprofits for over a decade. When AI tools became useful, she integrated them. She didn’t rebrand her entire business around them.

Now she runs a program called “Building Thought Leadership with LinkedIn” where she teaches C-suite executives how to actually use LinkedIn. No cheats or shortcuts. No growth hacks. No “viral secrets.”

Real strategy. Budget-conscious. Scalable. Sustainable.

She was named a Commonwealth Heroine. Twice named to Boston’s “50 Most Influential Business People of Color.” She chairs the Charles River Regional Chamber. She serves on Boston University’s Black Alumni Leadership Council.

None of that happened because she sold an AI course.

It happened because she’s been doing real work for real businesses for 13 years.

That’s the difference.

Angela uses AI as a tool. The grifters use AI as a marketing hook.

Angela teaches you how to think. The grifters sell you templates.

Angela’s been building her reputation for over a decade. The grifters showed up last year.

Try This Today & Spot The Grift

Here’s how you know someone’s selling snake oil:

They promise fast results. “10X your business in 30 days!”

They lead with income claims. “I made $50K last month!”

Their expertise is recent. Check their LinkedIn. Were they in AI two years ago? Or were they in crypto?

They sell courses, not results. Real consultants get paid when you succeed. Grifters get paid when you buy.

They have more students than clients. If they’re so good at AI, why aren’t they working with businesses?

Here’s how you know someone’s legit:

They’ve been doing this longer than AI has been trendy.

They talk about specific problems they solved for specific clients.

They have credentials that existed before ChatGPT launched.

They teach principles, not shortcuts.

They’re recognized by actual institutions, not just social media followers.

Angela Pitter checks every single one of those boxes.

Why This Matters

The grifter problem isn’t just annoying.

It’s actively hurting people.

Small business owners are spending thousands of dollars on courses that don’t work. They’re wasting months following advice from people who’ve never run a real business.

And then they think AI doesn’t work.

They tried it. They followed the “expert.” They bought the course. Nothing happened.

So they give up.

And that’s the real tragedy.

AI does work. When you learn it from people who actually understand technology and business. When you focus on solving real problems instead of chasing hype.

But you’ll never know that if your introduction to AI is some grifter selling you a $1,500 prompt pack.

This is why I keep writing this newsletter.

Because the people who need AI the most are the ones getting ripped off the hardest.

The small business owners who don’t have time to sort through the garbage. The employees trying to keep their jobs. The people just trying to work smarter, not harder.

They deserve better than grifters.

They deserve people like Angela Pitter.

I’m not going to pretend this doesn’t frustrate me.

Finding the bright spots in this space takes work. Real work.

But they’re out there.

Angela Pitter is one of them. If you want to see what real AI education looks like, check out her work at LiveWire Collaborative.

And follow her on LinkedIn. https://www.linkedin.com/in/angelapitter/

No get-rich-quick promises. Just real strategy from someone who’s been doing this since before it was cool.

That’s the kind of person worth paying attention to.

See you next Wednesday, Dex

P.S. - If you’re selling an AI course and you’re mad about this newsletter, good. You should be. Do better or get out.

P.P.S. - Another shout out, I made a dope LinkedIn friend, her name is Stephanie Coalson, she and her husband are two of my most favorite people on the platform right now, and she specializes in all things Disney vacations! She will be helping plan the Brocks family 2026 Disney Trip, and I’m very excited for that. Check her out if you want to level up your Disney trip experience! https://www.linkedin.com/in/stephanie-coalson-%F0%9F%8F%B0-333660266/

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. 770 people. Gone. One phone call.

And that’s just one of the seven AI startups that died in 2025.

Seven companies. Over $650 million in combined funding. Nearly 1,000 people total who lost their jobs. Some got zero notice. Others watched their companies implode over months of false hope and broken promises.

Meanwhile, KB is a post-grad architecture student who uses free AI tools and just 5x’d her workflow.

No funding. No pivot strategy. No board meetings.

Just a specific problem and some free software.

AI Concept of the Week: The $650 Million Problem Nobody Wanted Solved

Builder.ai ($450M raised, 770 jobs lost): Promised you could build apps “as easy as ordering pizza.” Most businesses don’t need custom apps. When Wall Street Journal investigated, they found the company’s “AI” was actually 700 human engineers in India manually coding everything. They kept that lie going for 8 years. Employees found out they were bankrupt during a company phone call. Many had been working with “zero dollars” in the bank accounts for days.

CodeParrot ($500K raised, YC-backed): Converted Figma designs into React code. Developers didn’t trust the code enough to use it in production. They pivoted so many times investors called it “pivot hell.” Made $1,500 in monthly revenue after 2.5 years before shutting down. Founder’s now on sabbatical after grinding for nothing.

Humane ($200M+ raised, multiple layoff rounds): The AI Pin. A $700 wearable device that was supposed to replace your phone. Ex-Apple team. Massive hype. Returns outpaced sales. The charging case was a fire hazard. HP bought some assets for $116M and immediately laid off everyone who worked on the actual product. Some employees got job offers at HP. Others got nothing.

Subtl.ai ($200K raised, 3-10 employees): Let you search internal documents with AI. Had clients like State Bank of India, but companies tried it and didn’t convert to paid plans. Accuracy issues. Too complex to integrate. Founder’s public quote: “I failed my team and investors.” Small team, but still people who lost their jobs.

Astra (backed by Perplexity’s founder): AI-powered sales automation. Launched in 2023. Dead by mid-2025. Co-founders couldn’t agree on growth pace. Enterprises didn’t want to give AI access to their Salesforce and Slack data. Lasted ONE YEAR. Team size unknown, but everyone lost their jobs over founder disagreements.

Wuri ($500K raised, YC-backed): Started as a no-code game creation platform for story-driven games. Then pivoted to transform web stories into audio-visual novels. High customer acquisition costs. Couldn’t scale. Founder’s quote: “Rapid change made it impossible to rely on past experience or traditional strategies.” They were chasing trends, not solving problems.

Locale.ai ($5M raised, 14-35 employees): Geospatial analytics for logistics and supply chains. Had international customers. Generated decent revenue. But after years of grinding through COVID and burnout, the founders returned money to investors and shut it down. They did it responsibly instead of dragging it out. Still, 14-35 people lost their jobs.

Now look at KB.

She’s recently graduated from a prestigious architecture school. She recently landed an amazing job in the town where she went to school. She builds 3D renders for actual construction projects. Her problem was specific: base renders from Enscape looked good, but they needed furniture, better lighting, and higher resolution to show clients.

Hiring someone to add all that? Expensive and slow.

She built a simple workflow:

• Enscape creates the base 3D render

• Gemini adds furniture and assets

• ChatGPT upscales everything and makes it photorealistic

Total cost: Maybe $20/month.

Time saved: She 5x’d her output. What used to take her a full day now takes an hour.

Seven startups with over $650 million in combined funding failed in 2025.

One college student with $20/month succeeded.

Real Business Win: What Actually Makes AI Work

Dawid left a comment on my last newsletter: “The real adoption barrier isn’t between promise and reality. It’s between having a tool and having a reason to use it consistently.”

Builder.ai, CodeParrot, Humane, Wuri, and the others had tools. KB had a reason.

Those startups were solving problems that sounded good in pitch decks. They were chasing visions and trends.

KB was trying to finish her homework faster.

The companies that work aren’t asking “what can AI do?” They’re asking “what problem am I sick of dealing with?”

KB didn’t wake up thinking “I should use Gemini today.” She woke up thinking “I need to add furniture to 12 renders and I have a deadline.”

AI was just the fastest way to solve that specific problem.

Try This Today: Find Your KB Moment

Stop thinking about AI tools. Start thinking about your most annoying recurring task.

What task did you do last week that you’re going to have to do again next week? And the week after that? And every week for the next year?

That’s your target.

Maybe it’s:

• Writing the same type of email 10 times a week

• Reformatting data from one system into another

• Creating social media posts from your blog content

• Scheduling appointments back and forth over email

• Pulling together weekly reports from different sources

Pick ONE. Not three. Not “my whole business.” One specific, annoying, repetitive task.

Now figure out if AI can do that specific thing.

Don’t build a custom solution. Don’t hire a consultant. Just see if ChatGPT, Claude, or Gemini can handle it.

KB didn’t need a $450 million platform. She needed three tools that already existed and a clear problem to solve.

Golden Nugget: The Human Cost of Hype

Builder.ai employees found out their company was bankrupt during a phone call. Many of them had been working for days with “zero dollars” in the company’s US and UK bank accounts. No warning. No severance for most. Just gone.

One engineer posted on LinkedIn: “Yesterday started as a normal day and by the end of it, we found out Builder.ai had filed for bankruptcy. Everything changed in an instant.”

These aren’t just numbers. These are people with mortgages. Kids in college. Rent due next week.

CodeParrot’s founders ground it out for 2.5 years. Pivoted. Tried everything. Made $1,500/month in revenue and had to shut down. Their team had to find new jobs in the middle of an AI hiring freeze.

Locale.ai’s founders were so burned out after years of nonstop work that they chose to shut down even though they saw new opportunities. They returned money to investors. Helped customers transition. But dozens of people still lost their jobs.

You know what’s working?

Boring invoice processing for accounting firms. Not sexy. Profitable. Nobody’s getting laid off.

Tools that help radiologists read scans 30% faster. Not revolutionary. Doctors pay for it. Stable jobs.

AI that books appointments for barbershops while the owner is mid-cut. Simple. Saves real money. The people who built it still have jobs.

The companies that survive aren’t the ones with the biggest vision. They’re the ones solving the most annoying problems.

And they’re not burning through hundreds of millions while nearly 1,000 people wait to see if they’ll have a job next month.

Builder.ai’s founder was at Davos in January 2024, talking about making people “superheroes.”

By May 2025, he’d laid off 770 people in a single phone call.

KB’s never been to Davos. She’s never raised funding. She’s never given a TED talk about the future of AI.

But she’s in the top 1% of people actually using AI for work.

She didn’t start with the technology. She started with the problem.

What’s the one task you’re doing this week that you’ve already done 100 times before?

Find that. Fix that. Forget the rest.

AI doesn’t fail. AI strategies fail when they’re built backwards.

And when AI strategies fail, real people lose their jobs. Nearly 1,000 in 2025 alone. And these are just the mainstream companies. That number’s going to keep climbing as long as companies keep chasing hype instead of solving problems.

See you next Wednesday, Dex.

The Chicago AI Guy

OH BTW - Research shows that 92% of AI startups fail. That’s higher than the regular tech startup failure rate of 63%. And 38% of AI failures? They launched products without market demand. They built first, then searched for customers. That’s backwards. And it cost nearly 1,000 people their jobs this year.

Small business owners got sold on AI harder than any tech in recent memory. The pitches were everywhere: “AI will 10x your business!” “Work 4 hours a week!” “Fire half your team and triple revenue!”

So they tried it.

And then they quit.

In 2024, 42% of small businesses were using AI. By April 2025? That number crashed to just 28%.

That’s a 33% DROP in adoption in one year.

But here’s what makes this really interesting: it’s not because AI doesn’t work. It’s because the hype made it impossible for AI to actually help anyone.

Let me explain.

The Hype Gap is the distance between what you were promised and what you actually got.

And right now, that gap is so massive that it’s killing AI adoption faster than any technology limitation ever could.

Here’s what the hype promised small businesses:

• AI agents running your entire customer service

• Automated sales that close deals while you sleep

• Content that ranks #1 on Google, written in seconds

• Chatbots that understand your customers better than you do

Here’s what small businesses actually got:

• ChatGPT that helps write emails (which is legitimately useful)

• Image generators that create weird hands

• Chatbots that frustrate customers more than help them

• A $149 course teaching them to use tools they could’ve learned in 20 minutes

Gene Marks is a small business consultant who works with 600+ clients and speaks at 50+ industry conferences every year. He’s talked to thousands of business owners about their AI usage.

His take? “Don’t believe what you read.”

He says most businesses aren’t “adopting AI” - they’re dabbling. They’re using ChatGPT to write an email. They’re generating a few images. They’re asking it to review a contract.

This is helpful stuff. But it’s not the revolution they were sold.

Real AI adoption - where AI agents automatically reconcile your accounts, place orders, converse with customers, and produce quotes based on historical data - isn’t happening at small businesses. Not even close.

Why not? Three reasons: cost, reliability, and trust.

The Guy Who Actually Made AI Work

Remember how I said AI CAN work? Here’s proof.

A business owner who runs a $1.5 million pet care education company went through this exact journey. He got caught up in the hype, tried every shiny new tool, and ended up with his team juggling 30 different AI applications.

His team spent more time switching between tools than actually working.

Sound familiar?

But then he changed his approach. Instead of chasing every new AI tool that launched, he focused on ONE thing: automating the workflows that already made him money.

The result? He reduced his team from 10 people to 3 while maintaining the same output.

Not by using AI chatbots or AI voice assistants or AI agents.

By automating boring, repetitive tasks in his existing business processes. One workflow per month. Document it. Automate it. Move on.

He says: “90% of AI tools being promoted today are more hype than help for real businesses making real money.”

The difference? He ignored the hype and solved actual problems.

The Numbers Don’t Lie

According to the NEXT Insurance survey of 1,500 small business owners:

• 58% say they have NO plans to use AI for business at all

• Only 23% would “definitely consider” adding AI (down from 27% last year)

• Just 19% - roughly 1 in 5 - might add it

The top barriers?

• 55% say cost is why they’re not using AI

• 62% don’t understand AI’s actual benefits

• 9% see it as a threat to their business

• 9% believe it won’t affect them at all

And here’s the kicker: the ones who ARE using AI are finding value. They’re using it for content creation (11%), customer service (9%), product recommendations (8%), scheduling (8%), and accounting (7%).

It’s just... not revolutionary. It’s incremental. It’s helpful, not transformational.

And that’s the problem. The hype promised transformation. Reality delivered incremental improvement.

When expectations are set at “this will change everything” and reality is “this saved me 30 minutes,” people feel disappointed - even when that 30 minutes is genuinely valuable.

Try This Today: The Un-Hyped Approach

Here’s what you should actually do if you want AI to help your business:

Step 1: Forget everything you’ve heard about AI “revolutionizing” anything.

Step 2: Pick ONE repetitive task you hate doing. Just one.

• Writing the same type of email over and over?

• Scheduling social media posts?

• Transcribing client calls?

• Creating first drafts of routine documents?

Step 3: Use ChatGPT (the free version is fine) to help with JUST that task for one week.

Step 4: Track the time you save. Actually write it down.

If it saves you even 30 minutes a week, that’s 26 hours a year. That’s three full work days you get back.

That’s three days you could spend with your family. Or working ON your business instead of IN it. Or just... not working.

That’s the real win. Not “AI replaced my team.” Not “I 10xed my revenue.”

Just: “I got Tuesday afternoon back.”

Why The Hype Is Actually Hurting You

Here’s the thing nobody’s saying out loud:

The AI hype isn’t just annoying. It’s actively preventing you from benefiting from AI.

When you’re told AI will “revolutionize everything,” you either:

1. Feel paralyzed because you don’t know where to start

2. Try everything and get overwhelmed

3. Buy expensive courses promising secret AI strategies

4. Give up when reality doesn’t match the hype

A translation company owner named Danilo Coviello said it perfectly: “AI can’t sense tone shifts, legal nuance, or when a vague phrase could cost a client down the line. It doesn’t ask follow-up questions. That’s where people still matter. Accuracy, accountability, and context still belong to humans.”

He uses AI behind the scenes for prep work and terminology checks. Not to replace his translators.

That’s it. That’s the secret.

Use AI for the boring stuff so humans can do the human stuff.

But when you’re sold on “AI will replace your entire workforce,” that simple, useful truth gets drowned out by disappointment.

According to MIT researchers, 95% of generative AI pilots at companies are failing. Not because the technology doesn’t work, but because expectations were set impossibly high.

Small businesses tried AI because someone told them they had to.

They quit because what they got didn’t match what they were promised.

The saddest part? Many of them probably found tools that saved them real time. Tools that could’ve given them more hours with their kids, more mental space, more freedom.

But because it wasn’t the “revolution” they were sold, it felt like a failure.

So here’s my question for you:

What if we stopped chasing the AI revolution and started appreciating the AI evolution?

What if saving 30 minutes a day was actually... enough?

That’s 3.5 hours a week. 182 hours a year. Almost a full month of work time.

Would you take a free month back? Or are you still holding out for the robot that does everything?

The hype killed AI for small businesses. But the reality - boring, incremental, helpful AI - is still sitting there, waiting for you to give it another shot.

Just this time, maybe ignore the promises and focus on the problems.

P.S. If you’re one of the 58% who said you’re not touching AI, I get it. You got burned by the hype. But don’t let the liars keep you from a tool that could actually help. Start small. One task. One week. See what happens.

And if you’re one of the 28% still using it? Keep going. Just stop trying to build the future and start solving today.

See you next Wednesday,

Dex

$30-40 billion invested in AI this year.

95% of those projects delivered exactly ZERO dollars back to the business.

Not “disappointing results.” Not “needs more time.”

Zero. Nothing. Complete failure.

And before you think “well that’s just big enterprise stuff, doesn’t apply to me” - it applies to you MORE. Because those companies have unlimited budgets, dedicated AI teams, and consultants out the wazoo. And they STILL screwed it up.

So what chance do you have?

Actually, a pretty good one. But only if you understand why everyone else is failing.

The Learning Gap

The MIT researchers expected to find that AI models weren’t good enough. That the technology was overhyped. That ChatGPT and all these tools were just fancy toys.

That’s not what they found.

The tech works fine.

The problem is what they call the “learning gap” - and it’s got nothing to do with the AI learning. It’s about YOU learning.

Companies are buying AI tools without understanding:

• What problem they’re actually trying to solve

• How their business actually works

• Where they waste time (the boring stuff they hate)

• How to integrate new tools into existing workflows

They’re doing it backwards. Tool first, strategy never.

Here’s what actually happened to most of those failed projects:

Some VP read about AI in Harvard Business Review. Got excited. Bought an expensive “AI solution” for sales and marketing because that sounds sexy. Never actually mapped out where their team wastes 10 hours a week on repetitive tasks. The tool sits unused. Everyone goes back to doing things the old way. Six months later, the CFO asks “what did we get for that $200K?” and nobody has an answer.

That’s the learning gap.

Not understanding AI. Understanding YOUR business well enough to know where AI can actually help.

The 5% Who Got It Right

So who’s in that lucky 5% that actually made money?

The MIT report found a clear pattern. The winners did three specific things:

1. They automated the repetitive tasks first.

Not the sexy stuff. Not “AI-powered sales forecasting” or “predictive customer analytics.”

They looked at back-office operations. The stuff nobody wants to do. Invoice processing. Data entry. Appointment scheduling. Document summarization.

The report found companies spending HALF their AI budget on sales and marketing tools... while the actual ROI was coming from back-office automation. They were buying sports cars when they needed a pickup truck.

2. They bought instead of built.

67% success rate when buying specialized tools from vendors.

33% success rate when building it themselves.

Small businesses especially - you do NOT have the time, money, or expertise to build custom AI systems. Buy tools that already work, customize them for your workflow, and move on.

3. They started small and specific.

Not “let’s transform our entire business with AI.”

More like “Sarah spends 5 hours every week manually following up with clients who haven’t booked their next appointment. Can we automate that?”

One problem. One solution. Measure it. Then move to the next thing.

The companies that succeeded picked ONE annoying, repetitive task that ate time and had AI handle it. Proved it worked. Then tackled the next one.

What You Should Do This Week

Don’t buy an AI tool this week.

Instead, do this:

Spend 30 minutes and write down every single task in your business that makes you think “ugh, I have to do THIS again?”

• Following up with leads

• Scheduling appointments

• Writing the same emails over and over

• Manually entering data from one system to another

• Creating weekly reports nobody reads

• Posting on social media

• Responding to the same customer questions

Make the list. Be specific. “Email” isn’t specific enough. “Sending appointment reminder emails every Tuesday” is specific.

Once you have the list, rank them by:

1. How much time does this waste per week?

2. How much do I absolutely HATE doing this?

The one at the top? That’s your first AI project.

Not because it’s the most important. Because it’s the most annoying AND time-consuming. Which means you’ll actually stick with the solution once you find it. And if you still aren’t sure, book a consult with me. https://stan.store/thechicagoaiguy

The Truth About That 95% Failure Rate

Here’s what nobody’s telling you about the 95% failure rate:

Most of those companies failed because they treated AI like they were buying software.

“We need an AI solution for X. Let me see some demos. Okay, this one looks good. Buy it. Roll it out.”

That doesn’t work.

Because AI isn’t like buying Microsoft Office where everyone knows how to use Word and Excel.

AI is like hiring an employee. You need to train it. You need to give it feedback. You need to adjust how YOU work to get the most out of it.

The 5% who succeeded? They didn’t just buy tools. They changed their workflows. They experimented. They iterated. They treated AI implementation like a six-month project, not a one-time purchase.

And here’s the thing that should make you pay attention:

90% of workers are ALREADY using AI tools. ChatGPT. Claude. They’re using them on their personal accounts because the corporate tools their companies bought don’t cut it.

Your employees have already figured out AI works. They’re just working around your failed systems.

Leave a comment

Look, I’m not going to sugarcoat this.

Most of you reading this are going to join the 95%. Not because you’re not smart enough. Because nobody’s actually teaching you HOW to think about AI implementation for small business.

Everyone’s either selling you tools or selling you hype.

Nobody’s saying “here’s exactly how to audit your business, identify where you’re bleeding time, match the RIGHT tool to THAT problem, implement it correctly, and actually get your hours back.”

That’s the gap I’m seeing everywhere. Smart business owners who get that AI could help them, but they’re stuck between “I should probably do something with AI” and “I have no idea where to start.”

I’m working on fixing that. More soon.

For now, just make that list. Find your most annoying time-suck. And start there.

Because the difference between the 95% who fail and the 5% who win isn’t that they’re smarter or have bigger budgets.

It’s that they actually understood their problem before they bought the solution.

Stop buying tools. Start solving problems.

See you next Wednesday, The Chicago AI Guy, Dex.

P.S. - The MIT report is public if you want to read it yourself. Here is the exact 26 page report. Click Here and prepare to feel better about your own AI confusion. At least you’re not a Fortune 500 company that just lit $5 million on fire for nothing.

While you were busy actually running your business last month, the AI arms race for small businesses officially kicked off.

Meta just launched an AI sales agent. Microsoft already has one. Google’s in the game too.

And here’s the kicker - this isn’t some future thing anymore. A survey from October shows 88% of small businesses are already using AI tools.

Not thinking about it. Not researching it. Using it.

And if this is news to you? Welcome to the party.

AI Sales Agents (And Why Everyone’s Building One)

On October 2nd, Meta announced something called Business AI.

It’s a sales agent specifically built for small and medium-sized businesses. Not a chatbot. Not another “tool.” An actual agent that automates sales processes and handles customer interactions.

And here’s what makes this different from all the other AI stuff you’ve ignored: it works on your website. Not just Facebook or Instagram. Your actual business website.

But Meta’s not special here. Microsoft launched their sales agent earlier this year. Google’s offering AI tools for businesses. Everyone with a tech budget is suddenly very interested in helping small businesses automate sales.

Why the sudden gold rush?

Because they finally figured out what we’ve known forever - small business owners are drowning in tasks that eat up time but don’t grow the business.

The Real Numbers

That survey I mentioned? It was done between October 3-9, 2025. 530 small business employers.

Here’s what they found:

88% are using AI tools right now. Not “planning to use.” Using.

73% say these tools have been important to their competitiveness and growth over the past year.

The average small business is using 4.8 different AI tools across their operations.

Read that again. Almost five tools.

What are they using them for?

• Business research

• Content creation

• Image and video development

• AI-powered email marketing

• Financial management

60% adopted AI to boost efficiency and productivity. 42% for customer service and support.

And here’s the money shot: 41% say AI lets them spend more strategic time growing the business instead of being stuck in the weeds.

Why This Matters More Than You Think

Look, I’m not telling you this to scare you.

I’m telling you because while you’re still deciding if AI is worth it, your competitors already automated three things you’re still doing manually.

When 88% of your competition is already using these tools, and 73% say it’s critical to staying competitive, you’re not making a choice about “if” anymore. You’re making a choice about “when.”

Waiting costs money. Actual money, not theoretical money.

Every week you wait, someone else in your industry is:

• Automating their customer interactions

• Creating content faster

• Managing their operations more efficiently

• Spending more time on strategy and less time on grunt work

35% of AI-adopting businesses are dedicating more resources to revenue-generating projects because AI freed up their time.

33% improved customer engagement and retention.

This isn’t about being cool or cutting-edge. It’s about not working weekends anymore.

The Thing Nobody Talks About

Here’s what I find hilarious about this whole situation.

Big tech companies spent years trying to sell complicated enterprise AI solutions that required a computer science degree to understand.

Nobody bought it.

Now they’re all scrambling to build simple tools for small businesses because they finally realized - small business owners don’t want “artificial intelligence.” They want their Tuesday afternoons back.

Meta, Microsoft, Google... they’re not competing on who has the smartest AI. They’re competing on who can make it easiest for a barbershop owner or restaurant operator to automate the boring stuff.

That’s the shift.

Leave a comment

Try This Today:

Don’t download anything yet. Don’t sign up for Meta’s Business AI or any other tool.

Just do this:

1. Pull up your calendar from last week

2. Write down every task that took more than 30 minutes

3. Circle the ones that were repetitive or administrative

4. Count how many hours you spent on circled tasks

That number? That’s where AI fits into your actual life.

Every one of those circled tasks is something that could probably be automated or assisted by AI. Customer interactions. Content creation. Email responses. Research. Financial management.

Now multiply that weekly number by 52.

That’s how many hours you could get back this year.

Golden Nugget:

Smart business owners aren’t using AI to replace people.

They’re using AI to replace the work humans shouldn’t be doing in the first place.

There’s a difference.

Closing:

Here’s my question for you: What would you do with 10 extra hours a week?

Would you finally work on that new service offering? Spend more time with customers? Actually take a day off?

The business owners who answered that survey aren’t smarter than you. They just decided to stop doing everything manually when robots could do it faster.

And honestly? The longer you wait, the weirder it’s going to feel when you finally make the switch.

Because in six months, 88% is going to be 95%.

Your call. But the math doesn’t lie.

See you next Wednesday, The Chicago AI Guy, Dex <3

P.S. - If you’re one of the 88% already using AI, hit reply and tell me what tool you can’t live without. I’m building a list for the newsletter.

Get a hold of me, and we can have a conversation about how I can get these done for you!

You’re already using AI.

ChatGPT’s open. Maybe Claude. Maybe something someone in your LinkedIn feed swore would change your life.

And yet? You’re still buried. Still working late. Still can’t find time to breathe.

Here’s the thing - you’re not using AI wrong. You’re just not using it COMPLETELY.

Let me show you what I mean.

The Difference Between Using AI and Actually Getting Your Time Back

Most people treat AI like Google on steroids.

Type a question. Get an answer. Close the tab. Repeat tomorrow.

But that’s like buying a car and only sitting in the parking lot. Yeah, you’ve got the keys. But you’re not going anywhere.

Stop asking AI to do things once. Start teaching AI to do things FOREVER.

Look - when you ask ChatGPT to write an email, it writes the email. Great. But tomorrow? You’re typing the same request again. From scratch. Explaining your business. Your tone. Your style.

That’s not AI saving you time. That’s you doing the same work with extra steps.

The real move?

Build systems. Create templates. Teach AI your voice ONCE, then use it over and over.

Think about what you do every single week:

• Answering the same customer questions

• Writing proposals

• Creating content for social

• Sending follow-ups

• Managing your calendar

If you’re explaining all this to AI fresh every time? You’re working just as hard as before. You’ve just traded one problem for another.

Where Everyone Gets Stuck

I see this constantly.

Someone figures out AI can write Instagram captions. Cool! They generate a post. Feel productive. Move on.

Next week? Same thing. Start from zero. Type it all out again.

Month later? “AI didn’t really save me time.”

But AI didn’t fail. YOUR APPROACH did.

The magic isn’t getting AI to do something once. The magic is building a system where AI does the SAME things repeatedly, automatically, in YOUR voice.

What Actually Works

Step 1: Find Your Repeating Tasks

What are you doing every week that takes 20+ minutes?

Your calendar knows. Your sent emails know. Your brain DEFINITELY knows.

Pick ONE task. Just one.

Step 2: Build The System

This is where people bail. “I don’t have time to set this up.”

But you’re gonna do this task 50 more times this year. Spend 30 minutes now. Save 15 minutes every time. That’s 12 hours back in your life.

Create a prompt template. Save it. Use it. Tweak it.

Give AI context about your business, your voice, your customers. ONE TIME. Then reference it every single time after.

Step 3: Stack Your Outputs

Stop treating every AI task like it’s isolated.

Draft your newsletter with AI. Then turn that newsletter into 5 social posts. Then create subject lines. Then write follow-up emails for people who didn’t open.

One input. Multiple outputs. THAT’S leverage.

Try This Right Now

The Audit:

Open your calendar from the past two weeks. Write down every task that:

• Took more than 15 minutes

• You’ve done before

• Involves writing, organizing, or analyzing

Pick ONE.

Build Your System:

Don’t ask AI to do that task once. Ask AI to build you a SYSTEM for it.

Copy this:

“I need to [your task] every week. Help me create a reusable template/process for this. Ask me questions about my preferences, style, and typical scenarios so you can customize this for me.”

Answer the questions. Save that conversation. Bookmark it.

Next week? Start there. Not from zero.

The Multiplier:

After AI helps with your task, ask:

“What else could we create from this? What other formats would be useful?”

Watch one piece of work become three. Or five. Or ten.

The Part Nobody Talks About

AI’s biggest superpower isn’t speed.

It’s MEMORY.

AI doesn’t forget your preferences. It doesn’t forget your last conversation. It doesn’t need you to re-explain your entire business model every single time.

You can build on what you did last week. Reference past conversations. Create a knowledge base that gets smarter every time you use it.

But most people treat every AI chat like meeting a stranger at a party.

Stop doing that.

You’re talking to the SAME tool. Teach it once. Build on it forever.

That’s where the hours come back.

Here’s The Real Talk

If AI isn’t saving you serious time, you’re not doing it wrong.

You’re just not going deep enough.

You’re scratching the surface when you could be 10 feet down. You’re having one-night stands with AI when you should be married to it.

The tool works. But ONLY if you set it up to work FOR you, not just WITH you.

Stop starting over every single time.

Build systems. Save templates. Stack your outputs.

Because AI isn’t supposed to be another thing on your to-do list.

It’s supposed to CLEAR your to-do list.

Question for you: What’s ONE task you’re doing this week that you’ve done 100 times before?

That’s your starting point. That’s where AI stops being cute and starts giving you your LIFE back.

See you next Wednesday.

PS: Here is a picture of my wife and I at Disney

You’re Busy.

Customers are in your face.

What If AI Just Answered It?

Last Wednesday at 3:47 PM, a barbershop in Dallas missed a call. The owner was mid-cut. The caller wanted a Saturday appointment. They called the competitor down the street instead.

That single missed call? $45 gone.

Multiply that by every busy afternoon, every lunch break, every time you’re with a customer and can’t pick up the phone.

Now imagine something else. Imagine AI answering that call. Checking your calendar. Booking the appointment. Sending a confirmation text. All while you’re finishing that fade.

That’s October 2025. And it’s happening in businesses just like yours right now.

What You’re About to Learn This Week: How AI voice agents work (in plain English), real stories of businesses saving hours every single day, prompts you can steal today, and one use case that’ll make you want to set this up by Friday.

Let’s go.

AI Concept of the Week: Voice Agents (No, Not Siri)

An AI voice agent is software that answers your phone calls and actually talks to people. Like a real person.

It can:

• Answer questions about your business

• Book appointments

• Take messages

• Transfer calls when needed

• Send follow-up texts

• Work 24/7 without coffee breaks

Here’s what makes them different from those annoying robocalls: They use something called conversational AI. That means they understand context, handle interruptions, and sound human.

When someone says “Actually, can I change that to Thursday instead?” the AI gets it. It adjusts. It confirms. It moves on.

Think of it as hiring a receptionist who never sleeps, never takes vacation, and costs about $100 a month instead of $3,000.

The Tech Behind It (Super Simple Version):

The AI listens to what people say (speech recognition). It figures out what they mean (natural language processing). It decides what to do (the AI model). Then it responds in a natural voice (text-to-speech).

All of this happens in about 2 seconds. Faster than most humans can think “wait, what did they just ask me?”

Companies like Bland AI, Retell, and CloudTalk are making this so easy that you don’t need to be technical. At all. Most platforms let you set up a voice agent in under an hour. No coding. Just clicking and typing what you want it to say.

Real Business Win: How a Dance Studio Got 12 Hours Back Every Week

Meet Jessica. She runs a dance studio in Phoenix with 150 students.

Her problem? The phone rang 40-60 times a day. Most calls were the same questions:

• “What are your class times?”

• “How much is registration?”

• “Can I reschedule my daughter’s class?”

Jessica was spending 10-12 hours a week on the phone. That’s not teaching dance. That’s just answering the same questions over and over.

What she did:

She set up an AI voice agent using a platform called Vapi. Took her about 90 minutes to configure. Cost her $89 a month.

She programmed it to:

• Answer common questions about class schedules and pricing

• Check her scheduling system and book trial classes

• Handle simple reschedules (within her 24-hour policy)

• Take detailed messages for complex requests

• Send confirmation texts automatically

The results after 30 days:

The AI handled 847 calls. That’s 42 hours of phone time. Jessica only took 8 calls that needed her personal attention.

She got 12 hours back every single week.

What did she do with that time? She launched two new dance programs she’d been putting off for a year. Revenue is up 23% in three months.

The best part? Parents love it. They can call at 10 PM after the kids go to bed and book a class. The AI doesn’t care what time it is.

One parent left a review: “Finally, a dance studio I can actually reach. Called at 9 PM on a Tuesday and had my daughter enrolled in 3 minutes.”

Leave a comment

Try This Today: 3 Prompts That’ll Save You Hours This Week

You don’t need a fancy voice agent to start using AI right now. Here are three prompts you can use in ChatGPT, Claude, or any AI tool today:

Prompt #1: Turn Your Email Chaos Into Action Items

Copy this exactly:

I’m going to paste 10 emails below. Read through all of them and create a simple action list organized by priority. For each action, tell me: 
1. What needs to be done
2. Why it’s urgent or not urgent
3. How long it’ll probably take

Make it scannable. Use bullet points. Be direct.

[paste your emails here]
```

**Why this works:** AI reads faster than you. It spots patterns. It doesn’t get distracted by long email chains. 5 minutes with this prompt beats 30 minutes of you trying to prioritize manually.

---

**Prompt #2: Write Follow-Up Texts That Don’t Sound Robotic**

Copy this:
```
I need to send a text to a customer who [describe situation: missed an appointment / needs to reschedule / hasn’t responded to my quote / etc.].

Write 3 different versions of this text. Make them:
- Friendly but professional
- Short (under 160 characters each)
- Clear about what action I need from them
- Not pushy

The vibe should be: helpful neighbor, not pushy salesperson.
```

**Why this works:** You know what to say, but saying it in a text that feels right is hard. AI nails tone. Pick your favorite version, send it, move on. Done in 2 minutes.

---

**Prompt #3: Create a Customer FAQ Page in 10 Minutes**

Copy this:
```
I run a [type of business]. My customers ask me the same questions all the time. I’m going to list the 10 most common questions below.

For each question, write a clear, friendly answer that’s:
- Easy to understand (8th grade reading level)
- 2-3 sentences max
- Includes the specific detail they actually need

Then organize these into a simple FAQ page format.

Here are the questions:
[list your top 10 questions]

Why this works: You’ve answered these questions 1,000 times in your head. Getting them written down is the hard part. AI does that for you. Now you can link to this page in emails, texts, or on your website. Every time you do, you save yourself 5 minutes.

Pro tip: Keep these prompts saved in a note on your phone. Anytime you’re doing something repetitive, ask yourself: “Could AI do this faster?” Then use one of these prompts as a starting point.

Golden Nugget: The Missed Call Isn’t the Real Cost

Here’s what nobody talks about: When you miss a call, you don’t just lose that customer.

You lose everyone they would have told.

Think about it. Someone calls your restaurant at 1 PM to make a reservation. You’re slammed with lunch service. They can’t get through. So they book somewhere else.

That’s not just one lost reservation. That’s also:

• The photo they would’ve posted on Instagram

• The friend they would’ve brought next time

• The review they would’ve left

• The fact that they now know your competitor’s name

One missed call creates a customer for someone else.

AI voice agents don’t just answer your phone. They stop your competitors from getting your customers.

The math is wild:

If you miss 3 calls a day, that’s 90 calls a month. Let’s say your average customer is worth $75. Even if only 30% of those would have booked, that’s $2,025 a month walking out the door.

Over a year? $24,300.

An AI voice agent costs $80-150 a month. You do the math.

The Use Case That’ll Change How You Think About AI Calling

Let’s talk about something most people haven’t thought of yet: AI agents for outbound follow-ups.

Everyone thinks about AI answering incoming calls. But what about all those calls YOU need to make?

Here’s a real scenario:

You’re a consultant. Last month you had discovery calls with 20 potential clients. 12 of them said “I’m interested, let me think about it” and then ghosted.

You know you should follow up. You just... don’t. It feels pushy. You’re busy. A week becomes two weeks becomes a month.

Enter AI voice agents for follow-ups.

Set up a simple outbound agent that calls your warm leads and says: “Hi [name], this is an automated call from [your business]. We had a great conversation a few weeks ago about [their project]. I wanted to check in and see if you had any questions or if you’d like to schedule a follow-up call with [your name]. If you’re interested, press 1 and we’ll get something on the calendar. If not, no worries at all. Have a great day!”

Sound too simple? It is simple. That’s the point.

Here’s what happens:

People who are ready to move forward press 1. The AI immediately transfers them to your calendar link or connects them to you if you’re available.

People who aren’t interested hang up. No hard feelings.

People who are on the fence hear from you again, which is often all it takes.

The beauty of this approach:

You’re not spending 2 hours making awkward follow-up calls. The AI makes 20 calls in 5 minutes. Your phone rings when someone actually wants to talk.

One marketing agency in Austin set this up last month. They made 150 outbound follow-up calls to old leads. 23 people pressed 1. 8 booked calls. 3 became clients worth a total of $47,000.

Total setup time? 2 hours. Total cost? $150 for the calling credits. Return? You do the math.

How to set this up:

Platforms like Bland AI and Synthflow let you build outbound calling campaigns with no coding. You upload a list of phone numbers. You write a script. You hit go.

Some platforms (like Vapi and Retell) connect directly to your CRM. So when someone responds, it automatically updates their status and triggers your next step.

You could have this running by Friday. Seriously.

Three businesses this works perfectly for:

1. Real estate agents: Follow up with people who toured a property but didn’t make an offer

2. Contractors: Check in on quotes you sent 2-3 weeks ago that got no response

3. Online shops: Call customers who abandoned their cart (yes, actually call them)

The key is to keep it short, honest, and helpful. No tricks. Just “Hey, we talked, I’m following up, interested?”

Your Wednesday Challenge

Pick one thing from this newsletter and actually do it today.

Not tomorrow. Not when you have time. Today.

• Use one of those three prompts and see what happens

• Research one AI voice agent platform (just 10 minutes on their website)

• Calculate how many calls you missed last month and what that cost you

• Forward this to another business owner who needs to see it

AI isn’t about replacing you. It’s about giving you back the time to do what you actually started your business for.

What’s one task you did this week that made you think “I really shouldn’t be the one doing this”?

Hit reply and tell me. I read every response.

See you next Wednesday,

Dex aka The Chicago AI Guy ❤️

P.S. Someone’s going to read this newsletter and set up an AI voice agent this week. Their competitors won’t. In 6 months, guess who’s going to be busier?

Quick Links From This Week:

• Bland AI (voice agents): bland.ai

• Synthflow (no-code voice agents): synthflow.ai

• Vapi (developer-friendly): vapi.ai

• CloudTalk (business calling + AI): cloudtalk.io

Quick question: How many times have you tried ChatGPT, gotten a garbage response, and thought “this AI thing is overhyped”?

Earlier this week, my guy Tony called me. Pissed.

“Aye man, I’m trying to do what you said and just typing to this ChatGPT to make this email for me. I asked it to write an email to my landlord about my broken AC and it sounds like a bad legal document written by a robot having a bad day.”

I said, “Tony, read me exactly what you typed.”

“Write an email to my landlord about AC.”

Yes, I got his permission to share this story lol

[Head hits desk]

Friend, that’s like walking into a restaurant and saying “food please” then getting mad when they bring you plain toast.

AI isn’t the problem. Your prompts are.

And I’m about to fix that in the next 10 minutes.

The Difference Between Amateur Hour and Pro Level

Here’s Tony’s prompt vs. what I taught him:

Tony’s Version: “Write an email to landlord about AC”

What ChatGPT Gave Him: “Dear Sir/Madam, I am writing to formally notify you of a malfunction in the air conditioning unit located at the premises...”

(Kill me now.)

The Pro Version: “Write a friendly but firm email to my landlord Jim. The AC has been broken for 5 days in 90-degree weather. I’ve texted twice with no response. I need it fixed TODAY or I’m calling a repair service and deducting from rent. Keep it under 5 sentences. Sound frustrated but not hostile.”

What ChatGPT Gave Him: “Hey Jim - It’s day 5 without AC in this heat, and I can’t do another night. I’ve texted twice about this already. I need someone here TODAY, or I’m calling a repair service myself and taking it off next month’s rent. Please confirm you got this and when someone’s coming. Thanks.”

BOOM. Problem solved. Jim had someone there by 4 PM.

The Secret Formula Nobody Teaches You

Every perfect prompt has these 5 ingredients:

1. CONTEXT - Who are you? Who are you talking to? Bad: “Write an email” Good: “I’m a freelance designer emailing a client who’s 30 days late on payment”

2. SPECIFIC GOAL - What do you actually want? Bad: “Help me with my resume” Good: “Add 3 quantifiable achievements to my resume that show I increased sales”

3. FORMAT - How should it look? Bad: “Give me ideas” Good: “Give me 5 bullet points, each under 10 words”

4. TONE - How should it sound? Bad: [Saying nothing about tone] Good: “Professional but warm, like talking to a colleague I respect”

5. CONSTRAINTS - What are the rules? Bad: “Make it good” Good: “Under 100 words, no jargon, 8th-grade reading level”

Real Examples From This Week

Realtor in Lincoln Park: Before: “Write house description” After: “Write a 3-paragraph MLS listing for a 2-bed condo in Lincoln Park. Highlight: walkable to everything, updated kitchen, tons of light. Tone: exciting but not salesy. Include one specific detail that makes buyers picture living there.”

Result: All open slots to view the house are filled, first time ever.

Manager at a Tech Company: Before: “Help with performance review” After: “I’m writing a performance review for a good employee who needs to communicate better. Give me 3 specific examples of how to phrase ‘you interrupt people in meetings’ as constructive feedback that won’t crush their soul.”

Result: Employee actually thanked them for the feedback.

Parent Planning a Birthday Party: Before: “Birthday party ideas” After: “I need 5 dinosaur-themed activities for 15 six-year-olds, using stuff I already have at home, that will keep them busy for 20 minutes each. Nothing messy. Apartment-friendly. Include one that will tire them out.”

Result: Best. Party. Ever. (And kids actually napped after.)

And a separate one, my friend is using Claude to help him and his wife brainstorm naming ideas for their child! It’s amazing when you prompt properly.

The Copy-Paste Templates That Always Work

Save these. Use them. Thank me later.

For Writing Anything: “Write a [TYPE OF CONTENT] for [AUDIENCE] about [TOPIC]. Tone: [FEELING]. Length: [CONSTRAINT]. Include: [MUST-HAVE]. Avoid: [NEVER-DO].”

For Solving Problems: “I’m a [YOUR ROLE] dealing with [SPECIFIC PROBLEM]. I’ve tried [WHAT YOU’VE ATTEMPTED]. Give me 3 solutions I haven’t thought of. Explain each in 2 sentences. Focus on what I can do TODAY.”

For Learning Something: “Explain [COMPLEX TOPIC] like I’m [KNOWLEDGE LEVEL]. Use an analogy about [FAMILIAR THING]. Give me one thing I can try right now to understand it better. Keep it under 100 words.”

For Awkward Conversations: “Help me say [DIFFICULT THING] to [PERSON]. Context: [RELATIONSHIP/SITUATION]. I want to be [TONE] but not [WHAT TO AVOID]. Give me the first sentence and the last sentence. Make it feel natural, not rehearsed.”

The Mistakes That Make AI Useless

Stop doing these immediately:

❌ Being vague: “Make it better” ✅ Be specific: “Make it 50% shorter and add a joke”

❌ No context: “Write a post” ✅ Give context: “Write a LinkedIn post announcing my promotion, humble but proud”

❌ Asking once: Getting one response and giving up ✅ Iterate: “Good start, now make it more conversational and add specific numbers”

❌ Wall of text: Cramming everything into one massive prompt ✅ Break it down: Start simple, then add layers

❌ Fighting the robot: Getting mad when it doesn’t read your mind ✅ Guide the robot: Tell it exactly what you want, like training a smart dog

The Game-Changer Most People Miss

Here’s what blew my mind as I’ve been researching and refining prompts for a couple years now, and what truly LAUNCHED my productivity to the moon:

You can teach AI your style. Once. Then use it forever.

Watch this:

“Here are 5 emails I’ve written: [paste them]. Analyze my writing style - how I start sentences, words I use often, how I structure ideas. Create a ‘style guide’ for writing like me.”

Then, every future prompt: “Using my style guide, write...”

BAM. Everything sounds like you.

My realtor friend did this. Now every listing sounds like her, not Generic Real Estate Robot #47.

Your 10-Minute Challenge

Right now, while you’re reading this, do this:

1. Open ChatGPT or Claude. (I chose Claude)

2. Think of one annoying thing you have to write this week

3. Use this exact formula:

“I need to write a [WHAT] to [WHO] about [TOPIC]. Context: [1-2 SENTENCES OF BACKGROUND] Goal: [WHAT YOU WANT TO HAPPEN] Tone: [HOW IT SHOULD FEEL] Length: [WORD/SENTENCE LIMIT] Must include: [KEY POINTS] Must avoid: [WHAT NOT TO SAY]”

4. Watch the magic happen

5. Reply to this email with what you created

Seriously. Do it now. Before you forget and go back to typing “write email about thing.”

The One Thing (This Changes Everything)

“The difference between AI that sounds like AI and AI that sounds like you is exactly 37 words of context. Most people give 5.”

Count the words in your prompts. I’ll wait.

The Thing I’ve Been Building

Look, I’ve been teaching this stuff one-on-one for months. Same questions. Same lightbulb moments. Same “holy WOW, why didn’t anyone tell me this?”

So I built something.

It’s almost ready. Like, scary close to ready. Like, I was gonna launch it today but, here we are lol

And when it launches, people who’ve been reading these newsletters will know first!.

Just saying. 😉

I’m so passionate about this. Prompting is the entire game with these tools. If you know how to prompt, your productivity is going to go through the roof.

This is the culmination of thousands of hours of working, interviewing, and chatting with people. Testing, iterating, and testing again. I want to lead with value and put you on EASY prompt street.

MORE ON THIS REAL SOON.

Think About This

What would change if every AI interaction you had actually gave you what you wanted on the first try?

Not the third attempt. Not after 20 minutes of frustration. First try.

That’s the difference between people who say “AI is overhyped” and people who can’t imagine working without it.

Which one do you want to be?

Let’s Talk About It

My neighbor just started using AI for her Etsy shop descriptions. Used to take her 20 minutes per product. Now? 2 minutes. And they convert better. MUCH BETTER.

She’s not technical. She’s 67. She learned this in one afternoon.

The prompt that changed everything for her: “Write a 3-paragraph Etsy description for [PRODUCT]. Customer is likely [DEMOGRAPHIC] looking for [NEED]. Include: how it feels to use it, why it’s perfect for gift-giving, one unexpected use. Tone: friendly neighbor recommending something they love.”

Sales up 40% this month.

From better prompts. That’s it.

Stop fighting the robots with bad instructions. Start commanding them with good ones.

Yamas (and go fix your prompts),

Dex The Chicago AI Guy ❤️

P.S. – My sister just asked me to help write an email to her HOA about our neighbor’s tree. My prompt: “Write an email that says ‘your tree is about to fall on my car’ without starting a neighborhood war. Professional but with subtle ‘I know a lawyer’ energy. 4 sentences max.” It worked. Tree guy coming Tuesday.

P.P.S. – That thing I’m building? You’ll know when it’s ready. Trust me. But maybe start practicing your prompts now. You know, just to be ready... 👀

P.P.P.S. – Still using one-sentence prompts? That’s like trying to paint a masterpiece with a crayon. You can do it, but why make life harder?

Time saved by using good prompts vs. bad ones this week: 4 hours. Time spent teaching Tony how to prompt: 10 minutes. Tony’s AC: Fixed. The robots work great when you speak their language.

Remember Monday when I said I’d show you the exact system that ran my business while I was eating my body weight in gyros?

And Tuesday, when I promised screenshots?

And yesterday, when I teased “the voice hack”?

Well, grab your coffee (or your freddo espresso if you’re fancy). We’re doing this.

But first... the legendary Vouliagmeni Lake fish story my wife won’t let me forget.

The Doctor Fish Incident of 2025

Picture this: We’re at Vouliagmeni Lake – this insane thermal lake about 30 minutes from Athens. The water’s naturally 75°F even in October because of underground thermal springs. It’s got these minerals and sulfur that supposedly cure everything from arthritis to bad life choices.

But here’s what the fancy website DOESN’T tell you...

The lake is full of Garra rufa fish. “Doctor fish,” they call them. They nibble dead skin off your feet as a “natural spa treatment.”

My wife: “It’s therapeutic! The locals swear by it!” Me: “I don’t need fish eating my feet.” My wife: “Don’t be a baby. Angelo The Greek said it changed his life.” Spoiler Alert, he didn’t say that lol

So I wade in. The water’s gorgeous – this perfect turquoise from the minerals. I’m feeling fancy. Sophisticated, even.

Then I stand still for literally THREE SECONDS.

HUNDREDS of these little doctor fish swarm my feet like I’m a walking Golden Corral buffet. Not a gentle nibble. We’re talking FEAST MODE.

Greek woman next to me: “Wow... they really like you!” My wife: [crying with laughter, taking videos] Me: [trying to act calm while fish are having Thanksgiving on my toes]

Other tourists are gathering. Someone’s kid points and says IN ENGLISH: “Mommy, why do all the fish want that man?”

Twenty minutes later, I had baby soft feet and a new reputation as “Fish Man” at the lake’s taverna.

But here’s the thing – while those Garra rufa were going to town on my neglected Chicago winter feet, Richard’s barbershop was booking clients, Angelo’s restaurant was answering emails, and my invoices were getting paid.

Because these 5 tools were working harder than those hungry sulfur-water fish.

The “Set It and Forget It” Arsenal

I’m giving you everything. The tools, the prompts, the actual setup.

Tool #1: The Email Answerer

Takes 20 minutes to set up, saves you 5-7 hours every week

The Tool: Gmail + Canned Responses (or any email platform with templates)

The Setup:

1. Go through your sent folder. Find your 20 most common email responses

2. Open Claude or ChatGPT

3. Feed it this specific prompt:

I’m going to paste 20 emails I send regularly. Create a template for each one that:
- Keeps my exact tone and style
- Has [BRACKETS] for parts I need to customize
- Includes a clear next step for the recipient
- Takes less than 30 seconds to personalize

Here are my actual emails:
[PASTE YOUR EMAILS]

Format each template like:
SITUATION: [When to use this]
TEMPLATE: [The actual template]
CUSTOMIZE: [What needs personalizing]

Real Example from Angelo The Greek: (Yes, the same Angelo who convinced me to try the fish lake)

• SITUATION: Customer asking about private events

• TEMPLATE: “Hey [NAME]! Love to host your [EVENT TYPE]. We can accommodate [NUMBER] people in our private room. Includes full menu access and dedicated server. Runs $[PRICE] minimum. Want to check out the space? Can show you around [DAY] afternoon. What works?”

• CUSTOMIZE: Name, event type, number, price, day

My Greece Results: 73 emails answered while I was literally floating in that mineral-rich lake, getting a fish pedicure. Clients thought I was working overtime.

Tool #2: The Appointment Ninja

30-minute setup for 8-10 hours back each week

The Tool: Calendly (free version) + Zapier (free tier) + Google Calendar

The Setup:

1. Create a Calendly with your availability (link it to Google Calendar to avoid double-booking)

2. Set up these appointment types:

   • Quick Call (15 min)

   • Consultation (30 min)

   • Deep Dive (60 min)

3. In Zapier, create this automation:

   • Trigger: New Calendly booking

   • Action 1: Add to Google Calendar with all details

   • Action 2: Send text to you (optional)

   • Action 3: Send confirmation email with this template:

Subject: Confirmed: Our [MEETING TYPE] on [DATE]

Hey [NAME]!

Looking forward to our chat on [DATE] at [TIME].

We’ll cover: [THEIR STATED REASON FOR MEETING]

Join here: [MEETING LINK]

Quick favor: Reply with the #1 thing you want to make sure we discuss.

See you soon!

Richard’s Calendly results: 47 bookings over 14 days. Average time to book: 2 minutes. His time spent: ZERO.

Tool #3: The Money Tracker

15 minutes to set up

The Tool: Your existing invoice software + this email sequence

The Sequence That Gets You Paid:

Here’s what to tell ChatGPT:

Write 5 payment reminder emails for my [BUSINESS TYPE]. 

Email 1 - Same day as service/delivery:
Subject: “Thanks for choosing us! (Invoice attached)”
Tone: Warm, appreciative
Include: Invoice attached, payment methods, thank you

Email 2 - Day 7:
Subject: “Quick invoice reminder”
Tone: Super friendly, assuming they forgot
Include: “I know how crazy things get”, invoice attached again

Email 3 - Day 14:
Subject: “Checking in on invoice [NUMBER]”
Tone: Still friendly but professional
Include: “Let me know if there’s any issue”

Email 4 - Day 21:
Subject: “Invoice [NUMBER] - Need your attention”
Tone: Professional, direct
Include: Late fee warning (if applicable)

Email 5 - Day 30:
Subject: “Final notice: Invoice [NUMBER]”
Tone: Firm but not angry
Include: Next steps if not paid

Make each email 4 sentences max. Never sound passive-aggressive.

Then set these up in QuickBooks/FreshBooks/Wave/whatever you use as an automated sequence.

The Psychology: People don’t pay because they’re evil. They pay when reminded at the right frequency. AI never feels awkward about reminding.

Tool #4: The Content Machine

45 minutes invested = 1 month of content created

The Tool: Google Docs + ChatGPT + Buffer (free version)

The One-Time Voice Training Setup:

This is the voice hack I’ve been teasing all week. Do this ONCE and AI will sound like you forever:

STEP 1: Feed AI your actual writing
“Here are 10 things I’ve written: [paste emails/posts/texts]
Analyze my writing style. Tell me:
- How I structure sentences
- Words I use often
- My humor style
- How I start/end messages”

STEP 2: Create your voice profile
“Based on that analysis, create a ‘voice profile’ for me that any AI can use to match my writing style”

STEP 3: Save this profile and use it for everything
“Using my voice profile, write [WHATEVER YOU NEED]”

Content Calendar Prompt (after voice training):

Paste this prompt:

Using my voice profile, create 30 social media posts for my [BUSINESS TYPE]:

Week 1: Educational tips about [TOPIC]
Week 2: Behind the scenes content
Week 3: Customer success stories
Week 4: Common mistakes to avoid

Format:
- 5 LinkedIn posts (professional, 150 words)
- 10 Facebook posts (friendly, 100 words)
- 10 Instagram captions (casual, add emoji suggestions)
- 5 Twitter posts (punchy, under 280 characters)

Include one clear call-to-action in each post.

Tool #5: The Research Assistant (The Secret Weapon)

10-minute setup with infinite hidden value

This is the one nobody talks about. While I was floating in that therapeutic sulfur water, this tool was learning about my industry, my competitors, and my customers.

The Tool: Perplexity AI (free) or Claude/ChatGPT with web browsing

The Weekly Intelligence Gathering Prompt:

Set a weekly reminder to run this prompt:

Research these topics for my [BUSINESS TYPE] in [LOCATION]:

1. What are my top 3 competitors doing differently this week?
2. What’s the newest trend in my industry?
3. What are customers complaining about in my industry?
4. Find one successful business in another city doing something innovative I could copy
5. What’s one AI tool my industry started using this month?

Give me actionable insights, not general information. Include links to sources.

Why this matters: While you’re handling today’s problems, AI is researching tomorrow’s opportunities.

The Actual Numbers (Because Proof Matters)

During my 14 days in Greece:

• Emails answered: 73

• Appointments booked: 12

• Invoices paid: 4

• Social posts published: 0 (I turned this off - vacation is vacation)

• New leads captured: 8

• Fires that needed my attention: ZERO

• Fish that ate my dead skin: Approximately 200 (not automated, very manual)

Time spent on business: Maybe 30 minutes total (checking that everything was working). Time spent getting fish pedicures: 30 minutes (felt like hours)

Your Step-by-Step Action Plan

Don’t try to set up all 5 today. You’ll burn out. Here’s your rollout:

Today (Wednesday): Set up Tool #1 (Email Templates). Just do 5 templates to start.

Tomorrow: Set up Tool #3 (Money Tracker). You probably have unpaid invoices. Go get them.

Weekend: Set up Tool #2 (Appointments). Stop the back-and-forth texting madness.

Next Week: Add Tools #4 and #5. By then, you’ll be addicted to the time savings.

In a month: Book your own trip to Vouliagmeni Lake. Let the doctor fish feast while your AI assistant handles everything. (The water really is 75°F year-round. It’s wild.)

The Golden Nugget (Screenshot This)

“Business freedom isn’t about making millions. It’s about your business running without you for 2 weeks while Greek fish are giving you a pedicure in a thermal lake.”

Something to Ponder

If your business could run itself for 2 weeks starting tomorrow, where would you go? What would you do? Who would you spend time with?

Don’t say “someday.”

These 5 tools make it possible next month.

Hit reply and tell me which tool you’re setting up first. I read everything (yes, even from Greek thermal lakes apparently).

Full Circle Moment

Look, I know what you’re thinking: “This sounds great, Dex, but I’m not tech-savvy.”

Neither was Angelo The Greek. Dude barely texts. But he set up all 5 tools in one afternoon with his son’s help.

Or you’re thinking: “My business is different.”

Richard cuts hair. Sarah does massages. The yoga instructor from Germany bends into pretzels for a living. These tools work for EVERYONE.

The only difference between you and someone floating in a Greek thermal lake is they decided their time was worth more than their fear of trying something new.

What’s Next Week?

I’m debating creating video walkthroughs for each tool. Step-by-step. Click-by-click. So simple that your 70-year-old uncle, who still has an AOL email, could follow along. However, I have another surprise in the tuck for next week too, lol

But honestly? You don’t need to wait. Everything you need is in this email.

The question isn’t whether AI can run your business.

It’s whether you’re ready to let it.

Yamas from Chicago (missing those Greek sunsets and yes, even those fish),

Dex The Chicago AI Guy ❤️

P.S. – My wife wanted me to add: The sulfur water at Vouliagmeni Lake supposedly has healing properties. My feet haven’t been this smooth since... ever. Sometimes the weird solutions are the best ones. (Kind of like letting AI run your business while doctor fish nibble your toes in Greece.)

P.P.S. – Richard just texted me. He’s booking his own Greece trip for March. Already researching Vouliagmeni Lake. It’s infectious!

P.P.P.S. – If you’re still reading this, you’re my people. Share this with one business owner who’s drowning in busywork. They’ll thank you when they’re floating in mineral water somewhere, getting a natural fish pedicure, not checking their phone.

“Create 10 magnetic FAQs for my [SPECIFIC BUSINESS TYPE] that turn curious browsers into loyal customers. Write like you're the most helpful, knowledgeable friend your customers never knew they needed.

For each FAQ:

Start with the EXACT words your customers use when they're stressed/excited/confused (not business jargon)

Lead with empathy - acknowledge their real concern before diving into the answer

Tell a micro-story when possible (30 seconds of relatability beats 30 bullet points)

Address the emotion behind the question, not just the logistics

End with a confidence-building next step that feels natural, not pushy

Must include these psychological trigger questions:

The Overwhelm Question - "This seems complicated, is it really as simple as you say?"

The Trust Question - "How do I know you're not like [bad experience they've had]?"

The Timing Question - "I'm not ready now, but when should I actually do this?"

The Investment Question - "Is this worth it, or am I just throwing money away?"

The Social Proof Question - "Do people like me actually use this?"

Plus 5 more covering: hours, booking process, your signature offering, policies, and their #1 practical concern

Tone: Warm coffee shop conversation with someone who genuinely wants to help you succeed. Professional but never corporate. Confident but never arrogant.

Secret sauce: Each answer should make them think 'Finally, someone who gets it!' and feel smarter for having read it.

Make every word count. No fluff. Pure value.”

So... remember that reliable Wednesday newsletter you've come to expect? The one that shows up like clockwork with AI tips to save you time?

Yeah, about that.

[Checks calendar]

It's been two weeks of radio silence. Not a peep. Nada. Zilch.

And before you unsubscribe, thinking I've abandoned ship, let me explain with a story that perfectly captures why we're all here learning about AI in the first place.

The Honeymoon We Never Had (Until Now)

Picture this: It's 2020. My wife and I just got married. We had big honeymoon plans – Greek islands, sunset dinners, the whole nine yards.

Then Covid showed up, and came with PACKED BAGS, it was here to stay. And decided to lock all of us down…so no Greece honeymoon.

Fast forward five years. I told myself, “Self, if you are still here and married 5 years from now, you will make good on this Greece trip.” It was major bucket list material for my wife, and I knew I had to fulfill it.

And here's where it gets interesting...

I 100% did not bring my laptop. When I first told my wife this, she didn’t believe me. (I had reneeged on that promise in the past.)

But I was dedicated to making good on this promise.

What Happens When You Actually Step Away

On Day 5 in Santorini, after visiting Athens and Hydra and Paros and others, I'm sitting at this tiny taverna overlooking the caldera, watching the sunset paint everything in a golden blue hue. My phone buzzes.

It's a text from Richard, who runs a barbershop in the ATL: "Big Homie, that scheduling assistant you helped me set up? It handled 47 bookings last week. I didn't touch my phone once. This is amazing."

I smiled, took another bite of this legendary Gyro (Greece’s street food is undefeated), and realized something profound.

This. THIS is why we're doing all this AI stuff.

The Conversations That Mattered

Even on vacation, I couldn't help having conversations about AI. But not the nerdy, technical kind. The human kind.

In Athens: Met a restaurant owner struggling with social media. Showed him how Claude can write Instagram captions in Greek AND English in 30 seconds. He literally hugged me.

During our romantic boat cruise in Santorini: Met an American couple who worked in the pharmaceutical space. Show her the possibility of having an AI Research tool to cut her time having to research into companies coming their way. We are getting dinner with them in Chicago next time they are in town.

On the ferry to Hydra: Talked to a yoga instructor from Germany who was burning out managing her online booking system. Introduced her to N8N + AI. If we are ever in Germany, free sessions will be available to us!

At a famous lake bar cabanna situation in Vouliagmeni: A restaurant owner from LA, who told me to put him in my phone as ‘Angelo The Greek’, mentioned spending 4 + hours a day on repetitive tasks. Spent 20 minutes showing him how to create AI email templates, among other things. My wife and I can now eat for free anytime we are in LA at any of his establishments.

But here's what struck me most...

None of these people cared about the AI itself.

They cared about what it gave them back.

Time with family. Energy for creativity. Freedom to actually RUN their business instead of being run BY it.

Angelo is mostly retired, and his son runs most of the business now, but he still loves to find himself in the day-to-day.

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The Work I Did (And Didn't Do) From Paradise

Let me be brutally honest about working from a Greek island:

What I thought I'd do: Wake up early, knock out 2-3 hours of deep work, then beach.

Then, when I decided not to take my laptop.

What actually happened: My wife is an adventurer, so we were up early every day, she was in her paradise and she was going to maximize that time she had lol. So we woke up, ate an incredible breakfast, drank too much freddo espresso (iced coffee that Greeks have PERFECTED), and feel zero guilt about it.

And you know what? My business didn't burn down.

Why?

Because I've spent the last year building AI systems that handle the repetitive stuff:

The ironic part? I built these systems, thinking they'd help me work more efficiently. Instead, they helped me work... less.

The Realization That Hit Me Like Greek Lightning

Sitting on a beach in Paros, watching my wife read a book while the Aegean Sea did its impossibly blue thing, it clicked.

We've been thinking about AI all wrong.

It's not about being more productive. It's not about crushing it 24/7. It's not about scale or optimization or any of that Silicon Valley nonsense.

It's about this: What if you could run your business AND have a life?

What if you could:

• Take a real vacation without checking in every hour

• Make it to your kid's recital without your phone blowing up

• Have a date night without mentally drafting tomorrow's social posts

• Sleep in on a Tuesday because you felt like it

This isn't fantasy. This is what AI makes possible RIGHT NOW.

Here's What I'm Building Next (Because of This Trip)

The Greece trip clarified something I've been wrestling with.

Most AI courses and tools are built for tech people. They assume you want to become an AI expert.

But you don't. You want to become an AI USER. Big difference.

So I'm creating something new:

The "Set It and Forget It" AI Playbook

Five AI systems that, once set up (I'll walk you through it like you're five), run your business basics on autopilot:

1. The Email Answerer - Handles 80% of customer emails in your voice

2. The Social Presence - Posts engaging content without you writing a word

3. The Appointment Assistant - Books, confirms, and reminds without you

4. The Content Machine - Blogs, newsletters, and updates that sound like you

5. The Money Tracker - Invoices, follows up, and celebrates when you get paid

Each system takes about an hour to set up. Then it just... works.

Your "Try This Today" Challenge

Since I left you hanging for two weeks, here's something you can implement in the next 10 minutes that'll save you hours this week:

The Vacation Responder That Actually Helps

1. Go to ChatGPT or Claude

2. Type: "Write 5 email templates for common customer questions in my [business type]. Make them helpful, friendly, and include a clear next step."

3. Save these in your email drafts

4. Next time someone emails with a common question, copy, paste, personalize one detail, send

5. Time saved: 5-10 minutes per email

Sarah from that massage studio I mentioned? She used this while in Cabo last month. Answered 17 client emails in under an hour from her beach chair. With a margarita in hand.

The Golden Nugget (Screenshot This)

"AI isn't about working smarter. It's about working so much less that you forget you have a business for a few hours each day."

That's not laziness. That's the entire point of being a business owner instead of an employee.

Coming Back to Reality (Sort Of)

I'm back at my desk now. Same computer. Same view. New Water Bottle (Shout out Epic Universe)

But something's different.

I've tasted what it's like to trust my systems completely. To know the business runs without me. To be present – actually present – with the people I love.

And I want that for you.

Not in some distant future when you've "made it." Not after you hit seven figures. Not when you finally have time.

Now. This month. This week.

Because here's what Greece taught me: The perfect time to step back never comes. You have to create it. And AI is the tool that makes it possible.

Your Thought-Provoking Question

What would you do with an extra 10 hours per week if AI handled your repetitive tasks?

No, really. Stop and think about it.

Would you:

• Finally write that book?

• Learn to make sourdough?

• Coach your kid's team?

• Take random adventures?

• Actually use that gym membership?

• Just... breathe?

Hit reply and tell me. I read every single email (yes, even the ones from Greece, apparently).

Next Week: The Specific AI Setup That Ran My Business While I Was Gone

I'll break down the exact 5-tool system that kept things humming while I was eating my body weight in Gyros. With screenshots, step-by-step instructions, and the actual prompts I use.

But for now, close your laptop. Take a walk. Call someone you love.

Because the whole point of this AI revolution isn't to work more.

It's to live more.

Yamas! 🇬🇷 (That's "cheers" in Greek – you're welcome)

-Dex The Chicago AI Guy ❤️

P.S. – My wife just read this over my shoulder and said, "Tell them about the foot sucking fish incident." Next week, friends. Next week.

P.P.S. – If you're thinking "must be nice to take two weeks off," you're right. It IS nice. And it's not because I'm special or rich or lucky. It's because I spent 6 months setting up AI systems that do the boring stuff for me. You can too. Start with that email template trick above. Seriously. Right now. Before you forget and go back to doing everything manually, like it's 1995.

Time saved writing this newsletter with AI assistance: 0 minutes. Some things are worth doing yourself. But those 47 booking confirmations Richard didn't have to send? That's where AI shines.

Let's be honest with each other here.

You check your email 36 times an hour.

I know because researchers stuck cameras on people's computers and counted. Thirty. Six. Times. That's once every minute and 40 seconds.

And here's the part that made me put down my coffee: it's not because you're weak or undisciplined. Your brain is literally getting high on email. Same dopamine pathways as slot machines. Same variable reward schedule that makes gambling addictive.

No wonder AI email tools feel scary. Your brain is protecting its drug supply.

AI Concept of the Week: The Dopamine Loop

Let me explain something that changed how I think about inbox zero forever.

Every time you check your email, your brain releases dopamine. Not when you READ the email. When you CHECK for it, the seeking itself is the drug. That's why you can clear your entire inbox and still feel the urge to refresh five seconds later.

Here's where it gets wild: dopamine doesn't make you feel satisfied. It makes you want to seek more. It's the neurochemical of "what's next?" not "I'm done."

Scientists call this a variable ratio reinforcement schedule. Sometimes you get a great email. Sometimes junk. Sometimes nothing. You never know. And that unpredictability? That's what makes it impossible to stop.

Now imagine this: what if checking email felt like checking your mailbox in 1985? Once, maybe twice a day. Done.

That's what Maria's boutique in Miami just accomplished. And she didn't use willpower. She used AI to break the loop entirely.

Real Business Win: Maria's 10-Hour Week Miracle

Maria owns a clothing boutique in Miami. Three months ago, she was answering emails until 11 PM every night. Her 8-year-old daughter asked why she loved her phone more than bedtime stories.

That hit different.

Here's what Maria discovered: she wasn't actually DOING email for 4 hours a day. She was checking her 7email every 6 minutes, losing 23 minutes of focus each time, never actually getting into what researchers call "deep work."

The math is insane. 96 interruptions per day. Times 23 minutes of lost focus. That's 36 hours of lost productivity from a 40-hour work week.

Maria started simply. She turned on Gmail's AI features (free, by the way). Then added SaneBox for $7 a month. Set up canned responses for her top 20 questions. The whole setup took a Saturday morning.

Week one: Email time dropped to 3 hours daily. Week four: Down to 2 hours. Week twelve: 45 minutes per day.

But here's the plot twist. Her response time got FASTER. Customers started commenting on her "amazing customer service." She wasn't trying harder. The AI was catching urgent stuff immediately while batching everything else.

The real win? Maria's daughter now gets THREE bedtime stories. And Maria discovered something that sounds fake but isn't: she literally had forgotten what it felt like to think clearly.

Turns out your brain can either check email or run a business. Not both.

Try This Today: The Identity Flip Exercise

This is going to sound weird, but stick with me.

The reason you won't let AI touch your email isn't technical. Its identity. Entrepreneurs check email obsessively because it feels like "being productive." It feels like "being responsive." It feels like "being a good business owner."

But what if I told you that 84% of entrepreneurs have imposter syndrome? And that email checking is actually how we hide from the real work that scares us?

Here's your homework. Takes 5 minutes:

Step 1: Write down your business identity in one sentence. Something like "I'm a massage therapist who helps people feel better" or "I run a pizza shop that brings families together."

Step 2: Write down how much time you spent on email yesterday. Be honest. Include the checking, the thinking about checking, the anxiety about not checking.

Step 3: Write what you could have done with that time that ACTUALLY fits your identity. More massages? Better pizza recipes? Playing with your kids?

Step 4: Here's the flip. Install ONE AI email tool today. Just one. If you use Gmail, turn on Smart Compose (Settings > General > Smart Compose > Writing suggestions on). If you're fancy, get SaneBox. If you're broke, use Gmail's free filters.

Step 5: Set email checking to THREE times today. Morning, lunch, evening. That's it.

You're not becoming a robot. You're becoming more human. The AI handles the robotic stuff so you can do the human stuff.

Golden Nugget: The 84% Secret

Here's the screenshot-worthy fact that'll blow up your group chat:

Small business owners who use AI email tools work 10-15 fewer hours per week. But their businesses grow 20% faster.

How? They stopped confusing motion with progress.

Clearing emails feels productive. Your brain gets 36 dopamine hits per hour. But you're not moving forward. You're running in place.

The businesses crushing it right now? They check their email 3 times a day. Their AI handles everything else. And they spend those reclaimed hours on what actually grows revenue: strategy, relationships, innovation.

One consultant saved 3.3 hours weekly just using Superhuman. That's 172 hours per year. A full MONTH of work days.

What would you do with an extra month?

The Psychological Truth Nobody Talks About

Your resistance to AI email tools has nothing to do with the technology. It's about control. It's about identity. It's about a brain that's literally addicted to checking.

Researchers found something fascinating: entrepreneurs have a stronger "internal locus of control" than regular people. We believe WE must control everything. Delegating feels like weakness. Even to a machine.

But here's what the same research found: entrepreneurs who can't delegate generate less revenue and create fewer jobs. The control that got you here is the control that'll keep you stuck.

The fix isn't forcing yourself to delegate. It's starting so small your brain doesn't notice.

One Gmail filter. One canned response. One AI summary.

Your brain needs 66 days to form a new habit. But it only needs one day to start.

What Would Your Wednesday Look Like?

Imagine this Wednesday.

You wake up. Check email once while coffee brews. AI has already sorted everything. Urgent stuff is highlighted. Routine questions are already answered. Meeting requests are already scheduled.

Time spent: 15 minutes.

You do actual work until lunch. Real, focused, brain-on work. The kind where you lose track of time because you're in flow.

Lunch email check: 10 minutes.

Afternoon is client time. Or product development. Or that project you've been "meaning to get to" for six months.

End of day check: 15 minutes.

Total email time: 40 minutes. Time reclaimed: 3 hours and 20 minutes. Bedtime stories read: All of them.

This isn't fantasy. This is literally what thousands of business owners are doing right now. Today. While you're checking your email for the 23rd time since breakfast.

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The Question That Changes Everything

What if being "responsive" is actually making you a worse business owner?

What if your customers would rather have you fully present for one hour than partially available for four?

What if your family doesn't need you to work less, but they need you to be actually done when you're done?

What if AI isn't taking something from you, but giving you back to yourself?

Next week, I'll show you how a barbershop went from 30% no-shows to 2% with one automation. The owner, Marcus, said something that stuck with me: "I thought my job was answering emails about appointments. Turns out my job was cutting hair."

What's your actual job? And how much email is keeping you from doing it?

Your brain is going to resist what I'm suggesting. It's going to say "but my business is different," and "but my customers expect immediate responses," and "but I need to be in control."

That's not logic talking. That's dopamine protecting its supply chain.

The question isn't whether AI can handle your email. It can. The question is whether you're ready to get your life back.

Start with one tool. Set three check times. Give it one week.

Your Wednesday self will thank you. More importantly, your family will notice the difference. You'll be there. Actually there. Not body-in-the-room-but-brain-in-the-inbox there.

That's worth more than inbox zero ever was.

Talk next week,

The Chicago AI Guy, Dex.

P.S. That 36 times per hour stat? I checked my email twice while writing this. The struggle is real. But now that we know it's neurochemistry, not weakness, we can actually fix it. See you on the other side of the dopamine loop.

That was like using your smartphone only to make phone calls.

Sarah, who runs a massage studio in Austin, just texted me at 9 PM last Tuesday. But she wasn't at her desk doing admin work. She was at her daughter's soccer game. "Just saved 3 hours on tomorrow's schedule using that voice prompt thing you taught me," she wrote. "This is insane."

She's not alone. While 200 million people use ChatGPT weekly, most are stuck in first gear, typing basic questions and getting basic answers. Meanwhile, the smart ones are turning it into an entire virtual team that works while they sleep.

Today, I'm handing you the keys to the Ferrari you've been driving like a golf cart.

AI Concept of the Week: Role-Based Prompting (Your New Virtual Assistant)

Here's what most people do: "Write me an email about our sale."

Here's what changes everything: "Act as an elite executive assistant with 10 years supporting small business owners. You understand cash flow stress, customer relationships, and the juggle of wearing 17 hats. Write me an email about our sale."

See the difference? You just hired a specialist.

Think of it like this: Would you ask a random person on the street to fix your plumbing? Or would you call a plumber? ChatGPT works the same way. Tell it WHO to be, and it transforms from intern to expert.

Malcolm’s barbershop went from sending generic appointment reminders to messages that sound like Malcolm actually wrote them. How? His prompt starts with: "Act as a friendly neighborhood barber who's been cutting hair for 30 years and knows everyone's kids' names."

His no-show rate dropped 40%. From one sentence.

Real Business Win: The Restaurant Owner Who Got Her Evenings Back

Maria owns an Italian restaurant in Denver. Every night after closing, she'd spend 2 hours on:

• Tomorrow's prep lists

• Inventory tracking

• Staff scheduling

• Responding to reviews

• Social media posts

Last month, she discovered Chain-of-Thought prompting. Sounds fancy. It's not.

Instead of asking ChatGPT twenty different questions, she gives it one killer prompt:

"Walk me through planning tomorrow's restaurant operations step-by-step. Consider: Tuesday typically does 80 covers, we have that new server training, and we're low on mozzarella. Think through prep, staffing, and potential issues."

ChatGPT now thinks like her sous chef. It catches things she might miss. It suggests moving the pasta special to Wednesday when the mozzarella delivery arrives. It reminds her that Juan requested Tuesday off three weeks ago.

Two hours became 20 minutes. Maria now reads bedtime stories to her kids instead of spreadsheets.

Try This Today: The Top 5 Prompts That Save You Time This Week

1. The Virtual Department Head

"You are my Chief Marketing Officer with 15 years experience helping small [industry] businesses grow from $[current revenue] to $[goal revenue]. You understand that my customers are [customer description], my biggest challenge is [specific challenge], and I only have [budget] monthly for marketing.

First, analyze my current situation and identify the three biggest opportunities I'm missing. Then create a 90-day action plan with specific weekly tasks I can do in 2 hours or less. Include exact scripts for customer outreach, email templates, and social media posts. Think like someone who's done this successfully 50 times before."

Real result: A dance studio owner used this and discovered she was ignoring corporate event bookings. Added $3,000/month with one email campaign to local businesses.

2. The Angry Customer Whisperer

"A customer just wrote this complaint: [paste their message]

You are a customer service psychology expert who has turned around thousands of angry customers for small businesses. You understand that behind every complaint is a human who wants to feel heard, and that how we handle problems matters more than never having problems.

Craft a response that:
1. Opens with genuine empathy (not 'we apologize for any inconvenience')
2. Shows I understand their specific frustration by reflecting it back
3. Takes ownership without legal admission
4. Offers a concrete solution plus a surprise gesture of goodwill
5. Ends with a personal touch that shows we're humans, not a corporation
6. Keeps the tone warm but professional - like I'm talking to my neighbor

Make it sound like me: [paste a paragraph of your typical writing]"

Tony's dance studio doesn't just resolve complaints anymore; parents share his responses as examples of "how customer service should be done."

3. The Hidden Money Detector

"You are a business optimization consultant who specializes in finding hidden revenue in small businesses. You've helped 500+ small business owners add 20-40% revenue without adding work.

My business: [describe your business, typical customer, average transaction, frequency of purchase]

Analyze my business model and identify:
1. Five specific ways I'm leaving money on the table (with estimated dollar amounts)
2. Three premium services I could add tomorrow using existing resources
3. Two pricing optimizations that won't lose customers
4. One referral system I could implement this week
5. The #1 efficiency gain that would save me 5+ hours weekly

For each suggestion, give me:
- Exactly how to implement it
- What to say to customers
- Expected results in 30/60/90 days
- A specific first step I can take today"

A massage therapist found $2,400/month in unused treatment room hours she could rent to other practitioners. Never occurred to her until ChatGPT pointed it out.

4. The Content Creation Machine

"You are a content strategist who has grown 50+ local businesses using social media without paid ads. You know that consistency beats perfection and that local businesses win through personality, not polish.

Create a complete month of content for my [business type] that serves [target customer]. 

Structure:
- Week 1: Building trust (behind scenes, staff spotlights, how we do things)
- Week 2: Education (tips they can use without buying from us)
- Week 3: Customer love (testimonials, transformations, community involvement)
- Week 4: Gentle sales (offers, new services, booking reminders)

For each post include:
- The exact caption (with emotional hook, value, and clear call-to-action)
- Hashtag strategy (mix of local, niche, and broader reach)
- Best posting time for my audience
- Photo/video description (exactly what to shoot with my phone)
- A quick reel/story idea related to the post

Voice: [describe your brand voice or paste sample]
Never use: corporate speak, emoji overload, or aggressive sales language
Always include: local references, personal touches, real stories"

Salon owner went from posting randomly to having parents share her "Dad Joke Tuesday" posts. Bookings up 30%.

5. The Meeting Transformer

"You are a meeting facilitation expert who has helped executives save 10 hours weekly by running better meetings. You know that most meetings fail because of poor preparation, not poor execution.

I have a [meeting type] with [who's attending] about [specific topic/decision needed].

Context: [brief background on the situation]
My goal: [what you want to achieve]
Their likely concerns: [what you think they're worried about]
Time available: [meeting length]

Create:
1. Pre-meeting email that gets them prepared and excited (not dreading another meeting)
2. Agenda with exact time blocks and outcome for each section
3. Opening statement that sets collaborative tone (90 seconds max)
4. Five powerful questions that cut through politics to real issues
5. Three likely objections with aikido-style redirects (use their energy, don't fight it)
6. Decision framework that makes the choice obvious
7. Clear next steps with owners and deadlines
8. Follow-up email template that locks in commitments

Format everything as a one-page reference I can glance at during the meeting."

Consultant turned her "maybe" meetings into "yes" meetings. Close rate jumped from 30% to 60%.

Golden Nugget: The Feature Nobody Knows That Changes Everything

Custom Instructions. It's hiding in your ChatGPT settings, and it's worth its weight in gold.

Here's what you do: Tell ChatGPT who you are, once. It remembers forever.

"I run a small bakery in Portland. My customers are families and coffee lovers. I write in a warm, approachable tone. I hate corporate speak. Always consider my limited budget and solo operation."

Now EVERY conversation starts with ChatGPT knowing your context. No more explaining your business sixteen times a day. That's 30 minutes saved, daily.

A salon owner told me this one feature gave her back 2.5 hours per week. She stopped typing "I run a salon" 50 times and started getting answers that actually fit her business.

Your Night’s Just Opened Up

Here's what I know: Right now, you're doing something manually that ChatGPT could handle in seconds. Maybe it's writing those supplier emails. Maybe it's creating next week's schedule. Maybe it's figuring out what to post on Instagram.

That freelancer saving 20 hours a week? She started with one prompt. The contractor who cut documentation time by 80%? One role-based conversation. BBVA Bank saved their legal department 40,000 hours annually. They started with a single custom GPT.

But truth is, it's not about the hours saved. It's about what you do with them.

It's about being at your kid's recital instead of your laptop. It's about having energy left for the strategic thinking that actually grows your business. It's about remembering why you started this business in the first place.

Was it to spend Tuesday nights doing admin work? Or was it for freedom?

This week's challenge: Pick ONE prompt from above. Use it three times. Time how long the task used to take versus now.

Then do the math on what your Tuesday nights are worth.

Next week, I'll show you how to turn ChatGPT into your personal business analyst using a feature 94% of users have never touched. (Hint: It involves uploading that spreadsheet you've been staring at for months.)

Stop working harder. Start working smarter. Your family's waiting.

— Chicago AI Guy (Dex)

P.S. I hope you are having a wonderful and I’d love it if you could share this with someone who can use it.

Remember last Tuesday when you stayed late to answer emails? Or that Wednesday morning you spent 30 minutes trying to find a meeting time that worked for everyone? What about Friday afternoon when you stared at a blank document, knowing you had to write that proposal but your brain was fried?

Yeah. We've all been there.

But here's what's wild: while you were wrestling with your inbox, Sarah from accounting was leaving at 5 PM sharp. She figured out something that's saving her 5 hours every week. And it's not working harder or some magical productivity hack.

It's automation. Specifically, three AI automations that are quietly transforming how smart people work.

AI Concept of the Week: Automation

(But I Make It Simple)

Let's talk about automation for a second. Not the scary, robots-taking-over kind. The "Sarah gets to have dinner with her kids" kind.

Automation just means teaching a computer to do the boring stuff you hate doing. Email sorting? Computer can do that. Finding meeting times? Computer's got it. Writing first drafts? Yep, computer again.

Think of it like having a really efficient assistant who never gets tired, never takes breaks, and costs less than your daily coffee budget.

Here's the thing everyone gets wrong: automation isn't about replacing you. It's about giving you back the time to do the work that actually matters. The creative stuff. The strategic thinking. The conversations that move things forward.

Real Business Win: How One Developer Reclaimed 12 Hours a Week

Meet Johnny, a software engineer at a fast-growing startup. Six months ago, he was drowning. Twelve-hour days were normal. Weekends meant catching up on emails and scheduling meetings for Monday.

Then he discovered three simple automations.

First, he set up SaneBox for his email. This AI tool automatically sorts emails by importance. The result? His inbox went from 150 daily emails to 20 that actually needed his attention. Time saved: 2 hours daily.

Next, he started using Motion for his calendar. Instead of playing calendar Tetris, he tells Motion his priorities and deadlines. The AI builds his entire schedule. Time saved: 3 hours weekly just from not thinking about when to do things.

Finally, he began using Claude for first drafts. Project proposals, documentation, status updates - anything that starts with a blank page now starts with an AI draft he can edit. Time saved: 7 hours weekly.

The math is simple: Johnny went from 60-hour weeks to 48-hour weeks. Same output, better quality, way less stress.

But here's the real win - Johnny now coaches his daughter's soccer team on Thursdays. That's what this is really about.

Try This Today: Set Up Your First Email Automation (15 Minutes)

Ready to start getting your life back? Let's begin with email, because that's where most people feel the biggest immediate relief.

If you use Gmail:

1. Go to gmail.com and look for the "Help me write" button when composing emails

2. Click it and type: "Professional response declining this meeting request"

3. Watch Gmail draft a polite response in 3 seconds

4. Edit it to match your voice, then send

If you use anything else:

1. Go to saneBox.com

2. Sign up for the 14-day free trial

3. Connect your email account (takes 2 minutes)

4. Let it run for 24 hours

5. Check your @SaneLater folder tomorrow - you'll be amazed what it filtered out

That's it. Seriously.

Don't overthink this. Don't research for hours. Just pick one and try it. You can always change later.

The hardest part isn't the technology. It's giving yourself permission to stop doing things the hard way.

Golden Nugget: The "5-Hour Freedom Formula"

Here's the shareable insight that'll make your friends say "wait, you can do THAT?"

Email AI + Calendar AI + Writing AI = 5+ hours back every week

But here's the secret sauce: don't implement all three at once. Do email first (biggest immediate relief). Add calendar automation after two weeks (once email feels normal). Add writing AI last (once the first two are habits).

Why? Because your brain can only handle so much change at once. People who try to automate everything immediately usually quit after a week because it feels overwhelming.

People who take it slow? They're the ones sending screenshots of their empty inboxes to their friends.

The math is beautiful:

• Week 1-2: Email automation saves 2 hours

• Week 3-4: Add calendar automation, now saving 4 hours

• Week 5-6: Add writing automation, now saving 6+ hours

By month two, you've reclaimed an entire workday every week. Use it wisely.

The Three Automations Everyone's Talking About

1. Email That Manages Itself

The tools: Gmail's built-in AI (free), SaneBox ($7/month), or Superhuman ($30/month)

The reality: A product manager I know went from spending 3 hours daily on email to 45 minutes. Same quality responses, zero stress.

The secret: These tools don't just sort your email - they learn what actually matters to you. After two weeks, they're basically reading your mind.

2. Calendars That Think Ahead

The tools: Motion ($34/month), Reclaim.ai (free tier), or Calendly with AI ($12/month)

The reality: An operations manager at Vodafone told me she stopped playing "calendar Tetris" entirely. The AI just handles it. She saves 4 hours weekly and never double-books herself.

The secret: You give these tools your priorities, and they build your entire schedule around what actually matters. No more "I don't have time for deep work."

3. Writing That Doesn't Suck

The tools: ChatGPT Plus ($20/month), Claude Pro ($20/month), or Notion AI ($8/month)

The reality: A freelance consultant I know uses AI for first drafts of everything. Proposals that used to take 6 hours now take 90 minutes. And honestly? The AI's first draft is often better than what she would have written from scratch.

The secret: AI isn't writing FOR you, it's writing WITH you. You still bring the ideas, strategy, and personality. The AI just handles the blank page problem.

What This Really Means

Look, I'm not going to pretend AI is magic. It's not going to solve all your problems or make you instantly successful.

But it will give you something precious: time.

Time to think strategically instead of reactively. Time to have conversations that matter instead of shuffling emails. Time to work ON your business instead of IN it.

Time for Tuesday dinners with your family instead of Tuesday nights at your laptop.

And isn't that the whole point?

The people figuring this out now aren't just saving time - they're completely changing how they work. While everyone else is still fighting their inbox, they're building the future.

The question isn't whether AI automation works. The question is: how much longer are you going to do things the hard way?

What's one task you do every day that you wish would just handle itself? Hit reply and tell me. I read every response, and I'm always looking for the next automation to test.

Remember: AI isn't about the technology. It's about getting your life back, one hour at a time.

Talk soon, Dex

P.S. - If you try any of these automations this week, I want to hear about it. Send me a screenshot of your empty inbox or tell me about the extra hour you got back. These wins deserve to be celebrated. I’ll feature you in next weeks Newsletter!

Hi Friends,

You probably saw it. Your cousin posted it. Somebody at the office shared it in slack. Maybe you laughed at a video of a cat doing Olympic gymnastics and wondered, "how the heck did they make that?"

Well, that viral "Cat Olympics" trend that crashed the internet? It was made with a free AI tool called Hailuo. And while everyone was laughing at dancing cats, smart business owners quietly figured out something bigger.

This same tool is saving them 15+ hours a week on video content.

No kidding.

And if you are one of the lucky ones who haven’t seen it yet…here you go!

AI Concept of the Week: Hailuo AI (It's Like Having a Hollywood Studio in Your Pocket)

Hailuo AI is a video generator that turns your words into actual videos. Not slideshows. Not animations. Real-looking videos.

You type: "A coffee cup steaming on a wooden table, morning sunlight streaming through window."

Hailuo creates: A 6-second professional video that looks like you hired a cinematographer.

The magic? It understands physics. Water splashes correctly. Gravity works. Fur moves naturally. That's why those cat videos looked so real they fooled millions of people.

And here's the kicker, it's FREE 99. 500 credits when you sign up, plus 100 more every single day.

Real Business Win: Sarah's Massage Studio Goes from Zero to Viral

Sarah owns a small massage studio in Denver. She used to spend $800 a month hiring someone to make social media videos. The results? Meh.

Last month, she discovered Hailuo.

Now she creates her own content in 5 minutes flat. She types prompts like "Relaxing spa scene with candles and soft towels" and boom - professional video content.

Her Instagram engagement shot up 340%. New client bookings doubled. And she's saving those $800 monthly payments.

But the real win? She now closes her laptop at 6 PM instead of staying late to edit videos. More time for dinner with her family.

"I felt like I had superpowers," Sarah told said. "My 12-year-old daughter was amazed that mom could make movie-quality videos just by typing."

Try This Today: Create Your First Hailuo Video (10 Minutes Max)

1. Go to hailuo.ai and sign up (it's free)

2. Click "Create Video"

3. Type this exact prompt: "[Your business type] with warm, welcoming atmosphere, professional lighting"

4. Hit generate and wait 2 minutes

5. Download your video

That's it. You just created content that would have cost you $200+ to hire out.

Want to get fancy? Try these prompts:

• "Customer enjoying [your service], genuine smile, natural lighting"

• "Behind the scenes at [your business name], busy but organized"

• "Before and after transformation, dramatic improvement"

Pro tip: The more specific you are, the better it works. Instead of "restaurant," try "cozy Italian restaurant with checkered tablecloths and steam rising from pasta."

Golden Nugget: The 2-Minute Rule That Changed Everything

Here's what Poppy's Pizza discovered: If you can create professional video content in 2 minutes instead of 2 hours, you'll actually do it.

They went from posting once a week to posting daily. Their online orders jumped to $76,000 in three months.

The secret wasn't better content. It was removing the friction.

When making videos stops being a project and becomes as easy as sending a text, everything changes. You post more. You engage more. You grow more.

And you get your evenings back.

The Bottom Line

While everyone was sharing cat videos, the smart money was paying attention to the tool behind them.

Hailuo isn't just about going viral. It's about getting your time back. It's about competing with bigger businesses without their budgets. It's about being home for dinner instead of stuck editing videos until midnight.

The Cat Olympics made us laugh. But for business owners who recognize opportunity, it might just change everything.

Question for you: What's one video you've been putting off creating because it felt too complicated or expensive?

Remember - AI isn't here to replace you. It's here to give you your life back.

Talk soon, The Chicago AI Guy,

P.S. The best part about AI tools like Hailuo? Your competitors probably think they're just for cat videos. While they're still hiring expensive video crews, you'll be creating content faster than they can blink. That's not just a business advantage, that's Tuesday dinners with your family instead of Tuesday nights doing admin work.

Did someone forward this to you? Subscribe to get weekly AI tips that actually save you time.

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:

1. Go to ChatGPT (it's free)

2. Type: "Write a professional but friendly appointment confirmation text for my [business type]"

3. Watch it create what usually takes you 5 minutes to write

4. 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.

Leave a comment

✨ 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.