I just sat down with Adam O’Leary on Simple Wins and we went deep on the one thing every entrepreneur is feeling right now — the ground is shifting under our feet because of AI.
If you’re a small business owner, a creator, or someone building anything meaningful, this episode is for you. We didn’t talk theory. We talked real moves I’ve made, the mistakes I learned from, and the tool I built because I saw the future coming fast.
Here’s the full breakdown.
I’ve been an entrepreneur my whole life. Turned down eight football scholarships senior year of high school, started mowing grass while my parents thought I’d lost my mind. Built and sold multiple companies. Syndicated real estate. Ran Carol Media, helping big insurance agents crush it online.
Then November 2022 happened.
ChatGPT dropped. First thing I did? Asked it to draw a family standing in front of a house. What came back? Melting faces and nightmare fingers. Straight horror show.
Most people laughed and moved on. I didn’t.
I live by one rule: Technology is undefeated.
So I dove in headfirst. April 2023, my wife and I are home with our newborn daughter, and the idea for Alli hit me hard. Companies aren’t going to have AI tools — they’re going to have AI team members. We launched her in April 2024, and she’s been on a tear ever since.
Alli isn’t another chatbot you have to babysit.
She’s your front-office AI team member built specifically for small business owners — the Paul the Plumbers, Mike the Mechanics, and Isaac the Insurance Agents of the world.
She handles the three highest-touch, lowest-budget pain points every owner deals with:
No more Front Desk Debbie going off-script. No more missed calls turning into lost revenue. No more outdated 2007 websites scaring customers away.
Alli is consistent. Professional. Trained on your business. And she speaks seven languages, so she scales.
Answering the phones sucks when you’re trying to grow. Answering services are inconsistent. Employees don’t follow the script. Customers are about to expect you to use AI to make their experience better — not worse.
I’d rather have a sharp two-minute conversation with an AI that knows exactly what to say than a painful five-minute one with someone who’s checked out.
That’s the shift. From “I don’t want to talk to AI” to “Why aren’t you using AI to make this easier for me?”
I built Alli for real business owners, not tech bros. You sign up, fill out a quick questionnaire, and our team does the white-glove onboarding. We build her for you. You forward your phones. Done.
Leads hit your app instantly — full transcripts, recordings, summaries. You get the data without the headache.
We talked about something even deeper on the show — the Hunter Head Game.
Once you see the game, you can’t unsee it. You go from being the hunted (reactive, waiting for things to happen) to the hunter (proactive, opportunistic, building no matter what the economy does).
Right now we’re heading into a massive K-Split — just like when the internet dropped. My own dad ignored email and websites and never made more than $20 an hour his whole life. That same split is happening again with AI, only faster.
Over the next 36 months, a lot of jobs (coding, customer service, junior roles) are going to get wiped out. Entrepreneurship is going from “nice to have” to “survival strategy.”
I told my team straight up: Learn this on your own time. The ones who do will move up. The ones who don’t… won’t.
The economy is splitting in two. You want to be on the upward path.
I’m not here to panic you — I’m here to prepare you.
AI isn’t coming. It’s here. And the entrepreneurs who learn to cohabitate with it, use it as leverage, and keep the Hunter Head Game strong are going to own the next decade.
You don’t need permission to build something meaningful. You need clarity, systems, leverage, and the right mindset.
That’s what I’m here for.
Watch the full episode, grab your copy of The Hunter Head Game and check out Alli in action for yourself.
We do this for life, not for likes.
Now go hunt.
— Coach Carroll
Alli is a front-office AI team member that answers your phones, manages your website, and handles social media engagement. She gives small business owners consistent, professional customer touchpoints without the high cost of extra staff. Perfect for plumbers, mechanics, insurance agents, and any local business tired of missed calls and outdated systems.
The K-Split is when a major technology (like the internet in the early 2000s or AI right now) divides the economy into two paths: one going sharply upward and one staying flat or going down. Those who adapt (learn AI, build systems, adopt new tools) ride the upward path. Those who ignore it get their earnings permanently capped — just like my dad who never made more than $20/hour after skipping the internet revolution.
The Hunter Head Game is the mindset I teach in my book and live by every day. It’s about shifting from being reactive (the hunted) to being proactive, opportunistic, and resilient (the hunter). Once you flip this switch, you start seeing opportunities, taking calculated risks, and building no matter what the economy throws at you.
Instantly. After our white-glove onboarding, you forward your existing phone number and Alli starts handling calls right away. You’ll get full transcripts, recordings, and lead summaries in our mobile + web app immediately.
Not at all. Alli was built for real small business owners, not tech bros. You fill out a simple questionnaire and our team builds and trains her for you. Super low lift — just forward your phones and you’re done.
AI is creating a massive split in the economy. Over the next 36 months, many traditional jobs will shrink while entrepreneurs who learn to use AI as leverage will pull ahead. The winners will use tools like Alli to deliver better customer experiences, cut costs, and free up time to hunt bigger opportunities.