Artificial intelligence is everywhere right now. Tools, platforms, predictions, and promises are flooding the entrepreneurial landscape, all claiming to save time, increase efficiency, or unlock growth.

But amid the noise, one question keeps surfacing for business owners:

Can AI actually help us build better businesses—without making them feel less human?

We all want the same thing from AI: Solve customer needs and clean up the back office at the same time. That’s the dream, right?

Instead of assuming it would work, I tested it.

I ran two AI experiments in parallel. One was public-facing and designed to serve customers directly. The other lived in the back office and focused on operational efficiency.

Both were intentional. Both were small. And both were built on the same philosophy behind Profit First, The Pumpkin Plan, and Clockwork.

Not a headline-grabbing stunt.
Not a rush to adopt the latest technology.
But a deliberate test rooted in the same philosophy that shaped Profit First, The Pumpkin Plan, and Clockwork: real progress comes from experimentation, not assumption.

What started as a test of AI capabilities became something much bigger—a lesson in clarity, momentum, and where humanity truly belongs in modern business.

The Customer-Facing Experiment: AI + The Guy 

Why did I choose this experiment in the first place? Because, entrepreneurs don’t struggle because they lack information. They struggle because uncertainty compounds faster than support.

A small question—Am I allocating cash correctly? Is this the right next step? Am I missing something obvious?—can quietly snowball into hesitation, delay, and eventually inaction. Momentum does not come from failure, but from friction.

,I’ve watched this happen for decades.

So the question wasn’t, “How can AI do more?”

It was:

What if technology could shorten the gap between confusion and clarity—without replacing human judgment?

That question became the foundation for what eventually evolved into AI + The Guy.

The Fear Most People Don’t Admit About AI

Resistance to AI isn’t always about the technology itself.

It’s about identity.

The worry is that automation will flatten nuance, dilute voice, or turn meaningful work into something transactional. I shared those concerns. My work has always been rooted in empathy, lived experience, and real-world testing. I didn’t want speed to come at the expense of connection.

So I set clear boundaries for this experiment:

• AI would not replace conversation.

• AI would not replace discernment.

• AI would not replace coaching or accountability.

Instead, it would support them.

That distinction mattered.

What Actually Happened When the Experiment Went Live

The first signs of success weren’t metrics.

They were messages.

People began saying things like:

• “I finally moved forward instead of overthinking.”

• “I didn’t spiral when I hit a question.”

• “I felt supported in the moment.”

Those responses revealed something critical.

The true value of AI in business isn’t productivity—it’s emotional relief.

Entrepreneurs don’t need more information. They need timely clarity. When the time between question and answer shrinks, confidence grows. Action follows.

That’s when the real insight surfaced.

The Aha Moment: AI Doesn’t Replace Humanity—It Protects It

Here’s the realization that changed everything for me:

AI doesn’t remove human connection. It reveals where human connection matters most.

When AI handled what it does best—retrieval, repetition, and immediacy—it freed me to focus on what only a human can do:

• nuanced judgment

• real-time coaching

• empathy

• truth-telling

Instead of being everywhere, I could be present where it mattered most.

This shifted how I define accessibility in business. Being supportive doesn’t mean being constantly available. It means designing systems that deliver the right kind of support at the right moment.

Why Alignment Matters More Than Intelligence

Another lesson from this experiment is that AI effectiveness has very little to do with raw intelligence—and everything to do with alignment.

Throughout this process, my friend and masterful AI consultant, Sandy Waggett, played a critical role in this grounding work.

consistently pulled the experiment out of theory and back into reality and back to the lived experience of entrepreneurs making decisions under real pressure, with real consequences.

The recurring question was simple but powerful:

Is this actually useful to a real entrepreneur, right now, when the stakes feel high and the margin for error feels small?

That lens shaped every decision. We didn’t chase complexity. We didn’t chase novelty. We chased clarity.

The result wasn’t a tool that felt robotic or generic. It felt familiar, practical, and grounded because it was aligned with real frameworks, real language, and real experience.

The Back-office AI Experiment: Kick Accounting Software

There’s another experiment happening quietly behind the scenes in my own business and it’s just as important.

We’ve started running our books in parallel: one set in our existing accounting system, and another in a new AI-driven accounting tool called Kick.

Why do this? Because I don’t just want to read about AI tools or assume they’ll make life easier, I want proof.

We’re watching closely to see:

• Does it actually save us time?
• Does it surface things our old system misses?
• Is the output clearer, more actionable, and more human-friendly?

At the end of the day, I won’t fully commit unless it’s a clear improvement that reduces friction, restores confidence, and supports better decisions. But that’s exactly what experiments are for: they let us push boundaries safely, gather evidence instead of opinions, and adopt new tools intentionally, not reactively.

This Was Never Just About AI

The deeper truth is this: the experiment was about intentional system design.

Designing businesses that:

• reduce friction instead of creating it
• restore momentum instead of draining energy
• support decision-making instead of overwhelming it

AI simply forced those questions to the surface. I’ve seen the same pattern play out across multiple experiments; on our speaking page, in how we’re pressure-testing Kick, and in how entrepreneurs respond when clarity replaces chaos.

The pattern is always the same:

Remove friction. Restore momentum. Respect humanity.

Practical Takeaways: How to Apply This in Your Business

You don’t need to adopt AI wholesale to benefit from this lesson. You do need to experiment intentionally. Here are four practical actions you can take right now:

1. Identify where momentum breaks
   Ask yourself: Where do I hesitate most in my business? Pricing? Cash flow? Hiring? Decision-making? That hesitation point is your highest-leverage opportunity for improvement.
2. Shrink the gap between question and clarity
   Look for ways, AI-driven or not, to reduce the delay between uncertainty and insight. Better systems, clearer documentation, decision frameworks, or tools that provide immediate guidance can make a dramatic difference.
3. Protect human energy
   Audit where your time is being spent on tasks that don’t require your judgment, empathy, or creativity. Delegate, automate, or redesign those tasks so you can focus on work that actually moves the needle.
4. Run small, reversible experiments
   Don’t overhaul everything at once. Test low-risk, time-bound, reversible changes. Experiments don’t demand certainty, but they do create it.

Why This Matters More Than Ever

Entrepreneurship is becoming more complex, not less. Information is abundant, but clarity is scarce. Tools are multiplying, but confidence is fragile.

The future doesn’t belong to those who adopt technology the fastest. It belongs to those who design intentionally, ask better questions, test before committing, and use systems to protect, not replace, their humanity.

A Final Invitation

Here’s the action I want you to take after reading this:

Find one friction point in your business. Just one. Then ask yourself:

What’s a small experiment I could run to make this easier?

Not perfect. Not permanent. Just intentional.

That’s how real breakthroughs happen. And if you’re curious about testing AI in your business, exploring Kick accounting, or running your own experiments, now is the perfect time to start.

You’ve got this!

-Mike