AI coaching
30 years of turning technology anxiety into fluency
One-to-one AI coaching for people running small businesses — especially, but not only, women — from someone who has guided people through every technology transition of the last three decades.
Who this is for
You run the business. You also run everything else.
The invoicing, the marketing, the customer service, and the thing you actually started the business to do. You’ve heard AI will change everything. You may have opened ChatGPT once, typed something in, got back a paragraph that sounded like a press release, and closed the tab.
That isn’t a knowledge gap, and it certainly isn’t a you problem. Nobody has ever explained this in plain language using your business, with your actual work in front of them. That’s the entire job here.
Handling public money, resident data, or anything regulated? Read the safe-practice rules first — they come before the clever part.
The background
Three decades of technology transitions
Ellen Escarcega has run Meserow Design in Seattle for thirty years. The firm builds the systems that track King County’s capital construction portfolio — software that has to keep working for twenty years, used every day by engineers and project managers who never asked to be given new software.
The job under the job title has always been the same one: stand next to a competent, irritated adult and make a piece of technology make sense to them.
The first three were changes of address. Software moved from paper to screens, from desktops to servers, from server rooms to the cloud — but the work itself stayed the work, and a business that migrated late still arrived roughly where the early movers were.
This one does not work that way. AI changes how much a single person can produce in a day. That makes the gap between a business with the fluency and one without it a multiplier rather than a head start — and multipliers compound every month they go unclosed. The firms that build it now will not end up a step ahead of the ones that wait. They will be operating at a different scale.
What has not changed is who comes out ahead. It is never the people who understand the technology best. It is the ones who got a straight explanation early, from somebody who was not trying to impress them.
Your coach
Meet Ellen Escarcega
Ellen founded Meserow Design in Seattle in 1997 and has led it ever since — a woman-owned software firm whose first client, King County, is still a client today. The systems her team builds run a multi-billion-dollar public capital program, which means her working life is spent making serious software make sense to engineers, accountants, and project managers who never asked to be handed new technology.
She has walked people through every transition on this page — paper to digital, desktop to server, on premises to cloud — and AI is the fourth. The coaching exists because the same explanation that holds up in a county briefing room works at a kitchen table: plain language, no jargon, and nobody trying to impress you.
Working safely
Nothing goes into an AI that shouldn’t.
Every engagement starts the same way, whether you are a two-person shop or a public agency: we decide what your AI is allowed to see, before it sees anything. It takes about twenty minutes, it is the whole difference between a tool and a liability, and you leave with it written down on one page.
01 / CLASSIFY FIRST
Sort the data before you touch a tool
Public, internal, confidential, regulated. Most people have never done this once, and it decides everything that follows.
02 / YOUR ACCOUNT
Your tenant, your admin, your logs
Business tiers you own, where your work is excluded from model training. Never a personal login, never a tool I administer for you.
03 / RETENTION
Assume it is disclosable
For a public agency an AI conversation can be a public record. We decide what is retained and where, so a records request is a search, not an emergency.
04 / A HUMAN DECIDES
AI drafts. A named person signs.
Nothing reaches a customer, a council, or a regulator without a person putting their name on it. The review step lives in the workflow, not in good intentions.
For public agencies. Meserow has built and operated systems for King County since 1997, including the software of record for a multi-billion-dollar capital program. We will map these rules to the AI guidance your oversight body already uses, and Ellen will join a call with your IT, security, or public-records staff before you sign anything. Set that up.
The long version — the full checklist and the exact settings to change — is free in ELI5 with Ellen.
Three ways to work together
Start free. Go as far as you want.
If you had to look up what “ELI5” means — that’s exactly the feeling this fixes. It’s internet shorthand for “explain like I’m 5.” Nobody ever explains this stuff to you. I will.
Everything useful is in ELI5 with Ellen, the free newsletter. The paid tiers exist for the part reading can’t do — getting you unstuck, and building the thing with you.
ELI5 with Ellen
Free
One post a week
A real business, the exact thing we set up, and what changed — written so you can do the same thing before lunch.
- No AI news, no think pieces
- Copy every workflow yourself
- Free, permanently
Office hours
$10/mo
or $96 a year
You’ll get stuck — that’s the part nobody plans for. Once a month we get on Zoom and I unstick you, live.
- Monthly live group session
- Send your question ahead if you can’t attend
- Replays of everything
The Setup Intensive
$750/yr
Ten seats a year
The fast lane. I study your business ahead of time, then we spend 90 minutes building your workflows — and you leave with them running.
- Async intake, so no live minute is spent on discovery
- 90 minutes, one to one, on your real work
- A 30-minute follow-up when you’ve lived with it
- Everything in the tiers above
10 of 10 seats open
The Setup Intensive
You hang up with it running.
One deep session with momentum beats three shallow ones. Anything left to “finish later” doesn’t get finished — not for lack of ability, but because you run a business and Thursday happens.
01 / BEFORE
You talk, I study
Five questions, or just five minutes into your phone’s voice recorder. Plus three real customer emails, your price list, and a screenshot of the spreadsheet you hate. I read all of it beforehand, so we never spend a live minute on “tell me about your business.”
02 / THE SESSION
90 minutes, building
Ten minutes on what I’m seeing and what we’re building. Then eighty minutes with your hands on your own keyboard, in your own accounts, on your own real work. Not a demo. Not a plan for later.
03 / AFTER
A follow-up, on your schedule
Thirty minutes a month or two later, once you’ve actually lived with it. Fix what got annoying, extend what’s working, and tell me what happened.
One afternoon, and the thing you keep meaning to automate is running.
Start with the free newsletter. Take a seat when you want it built with you.
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