Heather Di Rocco
- Jan 31
- 2 min read
My Full Name
Heather Di Rocco
My Skool Community Name
AI in Wonderland
Brief Personal Background
I’m a Kailua, Hawaii–based, beach-walking, book-devouring, Coco-the-dog–snuggling human who accidentally built a life at the intersection of spycraft and spreadsheets. Outside of work you’ll find me chasing sunsets, planning purposeful travel, and nerding out on systems the way some people nerd out on reality TV. I bring a mix of curiosity, dry humour, and “you’ve got this” energy into pretty much every room I walk into.
Brief Professional Background
I started my career in finance at Oppenheimer Funds in the World Trade Center, then spent 20 years in military intelligence before realizing I was far more obsessed with the tech than the money or when WW3 was going to happen over Taiwan. Now I’m an AI strategist and business coach who helps non‑tech entrepreneurs turn AI from “I’m so behind” into “why didn’t I do this sooner?”. I build communities, custom bots, and practical systems that actually save time and make businesses more profitable.
How did you discover Skool?
I first used Skool simply as a container for programs I’d bought, like a quiet back room I never decorated. Last year a friend told me, “You should be here instead of in a Facebook group,” and it turns out that was the best decision—I finally had a home for my own world.
What inspired you to start your Skool community?
I didn’t want yet another class; I wanted a rabbit hole—somewhere people could explore AI, systems, and automation together without feeling dumb or behind. AI in Wonderland is my space to pour out the strategies, workflows, and experiments I usually reserve for clients, but in a playful, curious, tea‑party kind of way. I’m here to prove you can be both whimsical and wildly efficient. But there are higher tiers if you want to do some more personal exploring than just in the Community Chat!
What transformation do your members experience?
Members go from “I’m late to AI and kind of terrified” to using it daily with ease, clarity, and a lot fewer open tabs. They save hours each week, make smarter decisions, and finally feel like the tech is working for them, not the other way around.
Who is your ideal community member?
ADHD entrepreneurs, tech‑hesitant business owners, and wonderfully curious humans who feel behind in AI but secretly know they’re meant to lead, not chase. If you talk to your computer, overthink your next move, and collect courses like potions, you’ll fit right in.
What's one unexpected lesson you've learned from running your community?
I’ve realized I’m less a moderator and more a curator—like the slightly mischievous guide pointing out the best doors, levers, and mushrooms to try next. The friendships and collaborations that have popped up between members have been the real magic.
If someone is considering joining, what would you tell them?
Take a chance on me and on yourself—wander in, touch the tools, ask the “dumb” questions, and see how quickly things shift. You won’t be sorry, but you might need a bigger calendar to hold all the ideas that start showing up.
Link to my Skool community's About page
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