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Hey there,
Before Jessica joined The AI Executive System, she was tracking her team’s hours with a pencil and a piece of paper.
Not even a spreadsheet. Paper.
She is a clinical neuropsychologist with a private practice in Boston. She also runs a nonprofit for low-resourced mothers in Mexico, and is building a company in Portugal to hold neuropsychological data from around the world, so clinicians anywhere can compare their patients fairly.
Three organizations. Three countries. One very non-techie starting point.
Six months later, she has AI agents running on a server in her own house, handling clinical data that legally cannot touch the internet.
You can hear it from Jessica herself. Her full interview is on the program page:
[▶ Watch: Jessica’s 6 months in The AI Executive System]
…or read on for the January conversation, the wall that nearly stopped her, and the experience that got her past it.
“I’m kind of a Luddite”
Her word, from her first interview with us.
“I don’t really even know how to use a spreadsheet. Which my kids can’t even believe.” She wasn’t being modest.
“My relationship to tech in general, and the whole AI revolution, was fear and trepidation, basically. I had no technical knowledge before, really, at all.” What she did have was a clear view of the problem.
“As a sole practitioner, I spend a lot of time on tasks that don’t need my brains to do.” The data-privacy and compliance wall
Jessica wanted to speed up the grinding part of writing patient reports. Not the clinical thinking, which is hers. The part where information from a dozen places gets pulled into one document.
The problem:
“It can’t touch the internet, like, really in any way.” (For medical data, this is called HIPAA compliance, and has variations for legal, financial and lots of other types of data you may handle in your career.) For her data, “just use ChatGPT” is literally illegal. Which disqualifies a lot of the AI advice on the internet.
So she took our self-hosted track for the maximum level of data privacy. Here’s where she landed:
“What AIEX taught me is that [my private] server can be a Mac Mini. And I can actually create the stuff that needs to be on it without becoming a programmer.” A neuropsychologist who couldn’t use a spreadsheet now has a private, compliant AI environment in her house. And she’s building a knowledge base of every report she has ever written, producing new ones in her own voice, on data that never leaves the building.
The Coaching & Fast Pass experience
Jessica joined our Coaching tier because she knew she wanted more hands-on time with me and my team.
“The one-on-one coaching has been critical just because I am so non-technical that often I need help just finding the button. Or where the thing is that you’re supposed to put the text into.” Nobody asks that on a group call with thirty people on it. But it’s the difference between finishing and quitting.
Getting her team onto her self-hosted platform:
“That was a more complex process than anybody anticipated. And it wouldn’t have happened without [Nyasha, a coach at IWAI]. I mean, it just wouldn’t have. I would’ve given up.” Then working out how her orchestrator talks to the rest of the system:
“I finally understood that about three weeks ago, and now I understand it and I can implement it in whatever else I build.” Notice what’s happening there: she has permanently learned a new concept (dozens, actually) and is able to apply those to all her future work — all because of her 1:1 experience in AIEX coaching.
That’s why AIEX Coaching Fast Passes exist.
“I don’t have that kind of time”
She said something else I’ve thought about a lot since, describing what would have happened without coaching:
“The amount of time it would take me to fuddle through it, and get frustrated, and get stuck, and not even know the right vocabulary to use? Not worth it. Plus I wouldn’t do it. I don’t have that kind of time. But I do have an hour to spend with Nyasha and fix the problem that I have.” Notice what she isn’t saying. Not I can’t learn this. She’s saying I don’t have room to learn it the slower way.
If that’s you, there are now two answers.
Coaching answers it an hour at a time. You build, and when you hit a wall you book a Fast Pass and someone on our team works your exact problem with you That’s the route Jessica took.
Executive Concierge answers it differently, and it’s brand new this enrollment. Our team builds 10 assistants with you: we help you pick the 10 that will matter most, build them, launch them in your environment, then hand them over and teach you to run and extend the system yourself.
It’s built for exactly the situation Jessica was in: hard constraints, a clear picture of what you want, no spare time to find the route. It didn’t exist in January. It’s also the smallest group we take.
Now, instead of tracking data with a paper and pencil, she’s building AI agents.
“It will expand both your technological knowledge and your technological competence probably, like, 300%. And it won’t be daunting. I mean, you’ll feel accompanied.” And I love this last part, because I insist we go into our work together with reasonable expectations:
“You don’t have to become a programmer, but you do have to learn some stuff.” Tomorrow
Her teams now work in one shared space with the AI inside it. Jessica estimates the funding list her colleague needed would have taken two weeks to build by hand. Her colleague did it in about thirty seconds.
But this is the line I’d want you to leave with:
“My six-month-ago self would be shocked that I actually get it. And seriously shocked that I could make an agent. I didn’t even really know what an agent was when I started.” If you’ve been reading this week thinking I’m not technical enough for this, Jessica is your answer. She started from pretty much zero tech skill, with hard constraints, and she got there in 6 months, with someone to call when she got stuck.
Enrollment for The AI Executive System closes tomorrow, Friday, at 11:59pm Pacific.
The program page lays out all three levels.
[Take a look and pick the level that fits →]
To your tech transformation,
- Rob Howard
Founder, Innovating with AI
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P.S. January, asked what she expected from the program: “I’ll believe it when I see it.”
July: a compliant AI ecosystem running on a Mac Mini in her house.
Her full interview is on the program page.
(Enrollment closes tomorrow, Friday, at 11:59pm PT.)
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