Hi everybody,
I spent the past weeks talking to dozens of small businesses. (I’ll tell you why below.)
I wanted to know their real experience of AI. What’s actually working? What are they trying next? What’s just a pipe dream.
Here’s what I heard - and where I think it’s going.
My next live lecture is Thurs, Nov 13th — I’m talking to franchise consultant Connor Groce about buying vs building vs franchises. If you’re interested in owning a business, this is a great place to start!
RSVP here (and if you can’t make it, I’ll send you the recording)
Based on what I'm seeing now, the use cases for AI in regular Main St businesses fall into four different stages. Each one looks further into the future.
Stage 1: Single-Player Mode
Most businesses are here already.
A typical white-collar worker on a computer spends 95% of their time in just a few different applications:
Email
Excel
PowerPoint
Their calendar
Slack / Teams / whatever
In the past year, though, AI has joined this shortlist. It’s ChatGPT, Microsoft Copilot, or something similar. It’s become a reliable and consistent part of a knowledge worker’s workflow.
Personally, this bucket is 95% of my use case for AI. It helps with my research for studying companies, pulling in sources and finding data points so I can be faster and more effective than if I had a team. It's totally worth the $200/month that I spend on it.
One interesting thing I heard: the people using these types of AI tools are the employees who were outperforming before.
They were already better at Excel, PowerPoint, or email. Now that an even more powerful tool has shown up, it's made them even stronger compared to typical employees.
For 95% of businesses, this is the extent of their AI use.
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Stage 2: Customer-Facing AI
This is where I'm seeing the biggest growth right now. Stuff like customer service, email responses, automated processing of a shared inbox.
Tons of people are building (or want to build) agents for this stuff based on automation tools.
The most interesting stuff is around voice and text communication with clients. Stuff that once required a whole call center can now be done with a much smaller team of humans augmented by strong voice or text agents.
One person had a single individual and a set of cloud AI tools handling the workload of six accounts receivable personnel. Instead of a human sending texts, running through scripts, doing follow-ups, and answering questions, it took one person to supervise the bots.
Another wants his property management business voice AI to handle and triage calls after hours. Next he’s looking at having it send out automatic repair requests with no human intervention.
The key here is ensuring that these bots are sufficiently reliable to be actually helpful, rather than just frustrating potential customers.
The other use cases here are addressing “internal customers” — so stuff like an HR chatbot, or an interactive internal knowledge base.
It makes sense: scaling up customer support or selling with less staff has a big upside, and if the bots have a brain fart, the damage is relatively low risk.
Only a tiny percentage of businesses are doing this at scale today. But it’s the next frontier.
AI usage will grow here for the foreseeable future.
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Stage 3: Internal Process and Workflow Automation
At this stage (which I think is still a ways in the future), AI systems will be baked into internal processes for a company.
Stuff like bank reconciliations, invoicing, verifying that a given vendor meets qualifications.
Today, this isn’t working very well.
Sure, there are tons of internal processes that are perfect for automation… in theory. But when it’s mission-critical stuff, you can’t take a risk on AI hallucinating and screwing it up.
So for now, a ton of paper-shuffling jobs are safe. These are key people, running processes with old-school software and elbow grease.
You might have seen MIT’s sobering report that 95% of organizations are getting zero return from AI.
Two thoughts:
The “zero return” is likely from them trying to dive into complicated Stage 3-level deployments. The reality is, the tech isn’t there yet (most AI systems still don’t learn over time), and the people aren’t ready. Most workers can’t even spell ChatGPT yet.
These enterprises are likely getting a ton out of stage 1 AI use (single-player mode), but they have no idea it's going on because it's bottom-up and organic.
My sincere advice is, don't try to add this stage 3 stuff to your company at this point. It's just doomed to fail.
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Stage 4: Digital Employees
This is where we’re headed eventually. Lots of people will hate this, but at this stage every employee is basically a manager for AI agents.
You'll talk to them just like a remote employee: lots of Slack and occasional live conversations. They’ll have long-term memory and learn their job over time.
Enterprises are ready for this. Managers have been learning how to hire, train, motivate, and compensate employees for centuries. Then in 2020, we all learned to do it remotely.
But you, me, and everybody else making a salary these days says that the technology is nowhere near ready for this.
And like most things that come out of Silicon Valley, expect that people are pretty good at predicting the eventual future, but wildly wrong about the timeline.
I bet we’re cool for decades.
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There’s an opportunity here.
My thesis is that a business can develop a real, sustainable competitive advantage by adopting some of these Stage 2 technologies.
Can you automate and enhance your customer communications via voice and text?
The tools are out there, and the world is pretty much ready. The challenge is that they’re still a bit of a mess for the average person to deploy… especially if you don’t want them to suck.
So, AN ASK: I’m mentoring a team who help people deploy AI voice and text agents for customer service, support and sales functions.
If you’re a business owner, and you’d be interested in talking with us (and potentially getting some help setting this stuff up), reply to this email and we’d love to talk to you.
That’s where I’m at these days on AI.
What do I have wrong? Know someone we should talk to? Hit reply and let me know. I read all your messages!
TOGETHER WITH HOLDCO CONFERENCE

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Holdco Conference 2026 is where serious multi-business owners go to learn and connect. Feb 9-12 in Sundance, Utah.
“Hands down the most actionable conference I’ve ever been to.”
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“THE place to learn about running and successfully operating a HoldCo. [...] I also made a ton of friendships I hope to cultivate for a long, long time.”
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Tickets are all-inclusive: conference, skiing, spa, room, meals.
3 things from this week
Appetizer: Earlier this week, the Acquisitions Anonymous crew looked at a security franchise. As our guest Connor Groce (next week’s lecture guest!) said: “You’ll never be rewarded for doing a good job here.”
Main: If you’re interested in the boom (bubble?) of AI solutions for business, Beehiiv founder Tyler Denk wrote about his experience of board members recommending a million and one AI tools. Read the whole piece here (You have to sign up for his newsletter.)

Dessert: I love this hat.

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Thanks for reading!
Michael
P.S. Quick reminder: if you’re interested in deploying AI voice and text agents in your business for CS, support, and sales — we’d love to talk to you. Reply to this email!
How can I help?
🌎 STAFFING → Hire with Near. Fortune 500-level talent, at prices any business can afford.
⛷️OWNERS → HoldCo Conference 2026. Where business owners meet, learn, scale and grow at a stunning Utah resort. Feb 9-12.
💡Q&A → I host regular free lectures on all things business. Coming up:
Nov 13 — Buy vs Build vs Franchise w/ Connor Groce
Dec 11 — Year-End Tax Savings for HoldCos w/ Mark Edler
Jan 9 — How to Build Winning Remote Teams w/ Franco Pereyra
💸BUYING A BUSINESS → Acquisitions Anonymous. Podcast where we break down businesses for sale… 440+ episodes in!
