From AI Pilots to Real Deployments
From AI Pilots to Real Deployments: Why Most Businesses Get Stuck (and How to Break Through)
Every week I hear it:
"We ran an AI pilot… but we can’t get it to scale.”
The truth? Most AI pilots don’t fail because of the tech. They fail because of everything around the tech.
And I know—because I’ve been living in the trenches.
Over the last 2.5 years, I’ve logged 300+ hours with ChatGPT and tested 100+ AI tools across real estate, education, compliance, and small business workflows. That puts me beyond the dabblers and right in the messy middle—where adoption either happens or dies on the vine.
The Big Problem: Pilot Purgatory
Companies love “proof-of-concepts” because they look innovative.
But most never get off the ground.
Why?
No training for the people using it.
No policies on what’s safe vs risky.
No process that connects AI to decision-making.
So the pilot fizzles. AI ends up as shelfware.
What I’ve Seen in Plain Sight
A real estate team pulled comps in minutes—but never used them in client meetings.
A small business summarized contracts—but no one trusted the results.
An investor shaved hours off research—but still missed deals because the team wasn’t aligned.
Different industries. Same outcome: the model worked… the humans didn’t.
The Cost Nobody Talks About
Every failed pilot doesn’t just waste money.
It wastes the only thing you can’t replace: time.
And in 2025, speed of learning is the moat. Faster learners win.
The Fix: Focus on Adoption, Not Apps
Stop chasing shiny tools.
Start building faster learners.
Ask yourself:
How do we train people to think with AI?
Where are the hidden choke points costing us money and risk?
What guardrails do we need that protect without slowing us down?
Because the real opportunity isn’t a new tool. It’s a new way of making decisions.
Introducing The Third Guarantee
That’s why I created The Third Guarantee—my new weekly newsletter.
Every issue gives you one actionable, no-fluff insight on:
Where AI actually saves time (not just in theory)
How to cut hidden risk you didn’t know you had
How to make confident decisions when the stakes are high
It’s the same thinking I use in my Decision-Intelligence Audits—distilled into one clear takeaway you can use immediately.
Why Call It The Third Guarantee?
Because the first two guarantees in business are simple:
Change is coming.
Most people will be caught unprepared.
The third guarantee?
📍 If you learn to see what’s hidden in plain sight—and adapt faster than your competitors—you win. Every time.
That’s the promise behind this newsletter.
Final Thought
AI won’t replace your business.
But failing to deploy it might.
📍 Subscribe to The Third Guarantee today. Stay out of pilot purgatory and learn how to deploy with confidence.
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