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Use AI as confidently as you use Google.
No more guessing what to type or worrying you’ll look silly. You’ll know exactly how to talk to it.
1-on-1 AI coaching · Orlando
Two hours from confused to confident.
You’ll walk away with ChatGPT, Claude, or Gemini installed and configured — plus the confidence to use them every day. No tech background required.
Who I work with
- Executives
- Business owners
- Parents
- Curious beginners
ExecutivesBusiness ownersParentsCurious beginners
After two hours
Two hours from now, you’ll be able to:
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Have ChatGPT, Claude, or Gemini set up the way you actually work.
Installed, configured, and tuned to your role, your industry, your life — not a generic demo.
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Walk out with use cases tailored to you.
Three to five real examples we build together, using your actual work, your family, your interests.
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Know who to ask when you’re stuck.
You’ll have me. One email and I’ll help you unstick. You won’t be on your own.
Book a Free Call
15 minutes. I’ll call you. No commitment.
Sound familiar?
Quietly feeling behind on AI is more common than you think.
And it’s entirely fixable. You don’t need another course or another YouTube rabbit hole. You need someone to sit down with you and make this simple.
“Everyone’s using ChatGPT and I still don’t really know what it does.”
“I’d rather not ask my junior colleagues for help.”
Who it’s for
Personal coaching for real people.
Whatever your starting point, we meet you exactly where you are.
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The Executive
Busy leaders who want to understand AI without sitting through junior-level trainings — or admitting they don’t know in front of their team.
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The Business Owner
Entrepreneurs ready to use AI to save time and grow, but unsure where to start or which tools actually matter for their work.
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The Parent
Moms and dads who know AI will shape their kids’ future — and their own — and want to stay a step ahead, not a step behind.
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The Curious Beginner
Anyone who senses AI matters but feels intimidated. You don’t need to be a techie — you just need a patient guide.
What we’ll build together
From simple wins to real builds.
Where you start depends on you. Here’s the spectrum we’ll work along together.
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Quick wins
In the first 20 minutes of your session.
- Summarize a 60-page document into 10 bullets
- Translate a confusing medical bill into plain English
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Real workflows
Things you’ll use every week after we wrap.
- A weekly status report drafted from your meeting notes
- Practice a hard conversation before you have it
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Real builds & routines
Connected tools and automations that work for you — Coaching Pack territory.
- A morning briefing pulled from your calendar, inbox, and priorities — waiting for you with coffee
- Inbox triage that learns what actually matters to you
- An assistant that drafts replies to your most common emails in your voice
- A weekly industry digest, automatically curated
- Auto-summaries of every meeting, with action items emailed to you
- A daily routine that pulls research on the things you care about
How it works
Three simple steps.
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Book a free 15-min call
Pick a time that works for you. I’ll call you, we’ll talk briefly, and you decide if it’s a fit.
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Spend two hours together
In person around Orlando or virtually. We’ll get your AI tools set up and walk through real examples from your life or work.
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Start using AI that same day
You’ll leave with hands-on skills and someone to email when you get stuck.
Book a Free Call
15 minutes. I’ll call you. No commitment.
Pricing
Two ways to start.
Begin with one Starter Session. Add the Coaching Pack later if you want to keep going.
Best for first-timers
Start here
Starter Session
2 hours · 1-on-1
$299
A deep, hands-on session to get you set up and confident with AI. We walk through real examples from your work or life, and answer every question.
- ChatGPT, Claude, or Gemini — your pick (or all three) installed and configured
- A guided walkthrough oriented to your real work, life, and goals
- A take-home guide with prompts, tips, and tricks for daily use
- In person around Orlando or virtual — your call
Keep going
Coaching Pack
3 × 60-min follow-ups
$499
For clients who’ve done a Starter Session and want to keep going. Three follow-ups over a month to deepen skills and turn AI into a habit.
- Three scheduled 1-on-1 follow-ups
- Email support between sessions
- New use cases tailored to your progress
- Designed for committed learners
Not sure which is right for you? Start with a free 15-min call.
Your guide
Hi, I’m Kyle.
This started with friends and family. People I knew who were curious about AI but didn’t know where to begin. Every time I sat down with one of them and walked through Claude or ChatGPT, the same thing happened — the lightbulb went on.
A few days later they’d text me about how they were using AI to write a tough email, plan a vacation, or think through a hard conversation. That’s the moment that hooked me. I realized a lot more people would benefit from someone simply sitting down with them for a couple of hours.
Kyle Gilmore
FOUNDER · ORLANDO, FL
“The smartest people don’t need to know all the answers. They just need to know how to ask the best questions. AI handles the rest.”
I’ve spent 16 years teaching, building, deploying, and supporting technology across the country, in just about every kind of role. After all those years, I’ve figured out the real secret to teaching tech: it isn’t the demos or the slides. It’s listening.
When I understand what you actually care about, I can steer the session toward the use cases that’ll change your week. We build your first wins around your hobbies, your work, or your family. Curiosity is the only prerequisite.
Off the clock
I’ve called Orlando home since 2015. I’m a husband and a dad of three, plugged into my church, on a sports sideline most weekends. When I’m not with my family, I’m reading up on and geeking out about the latest AI developments.
— Kyle
FOUNDER · THE ORLANDO AI GUYS
Listening over lecturing
Most tech training is one-sided. The secret to actually learning AI is being heard first — then taught.
No code required
You don’t need to be a developer. If you can describe what you want, you can use AI.
Yours, not mine
Every session is built around your real work, hobbies, or family — not a generic demo.
Get started
Two hours could change how you work forever.
Pick a time that works for you and leave me your phone number. I’ll give you a quick call — 15 minutes, no commitment, no sales pitch.
Book Your Free 15-Min Call
Opens my Google Calendar. Pick a slot, leave your number, I’ll call you.
Length
15 minutes
Cost
Free, always
Format
A phone call from me