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House Rules

The Operator’s Framework for AI Deployment

Ten years running restaurant floors, a few years running my own online retail business, two years shipping AI apps. It has been the same job every time. Keep the system up while people are counting on it.

01The zigzag

This does not look like a normal resume

Here is the order it happened in, and what each job taught me.

  1. Bartender at a pool hall, then the de facto manager with the keys whenever the owner was away.

  2. Helped open a new location for a national grill chain, then supervisor with opening keys.

  3. Manager at a busier location in the same company. Bar first, then service, then marketing, then the kitchen.

  4. Bar manager to service manager to assistant general manager at two higher volume restaurants. I left the industry when COVID hit.

  5. Ran an online retail business for a few years, then moved to building AI products. 12+ live products.

02The incident

The Sunday lunch rush

Sunday lunch is one of the two or three busiest shifts of the week. That Sunday the point of sale went down. No tickets, no card payments, nothing.

I stopped seating people for a minute and made one decision: every guest hears it from me before they sit down, not from a server after they have eaten. We took cash where people had it. We handed out gift cards where they did not. I kept the kitchen cooking off handwritten tickets and I touched every table in the dining room, twice if the food was slow.

Comps ran 20 to 30 percent of the day’s sales. That is an ugly number and I would take it again. Nobody left angry.

The same shift, translated

What a restaurant outage and a stalled AI rollout have in common, and the move in each case.
EntryOn the floorIn an AI rolloutThe move
01The point of sale goes down mid rushA model or an API degrades in productionTell the people it affects before they find out on their own
02The kitchen keeps cooking, the front cannot ring anything inOne subsystem is fine and the handoff between them failsGo find the broken handoff, not the broken team
03Comps reach 30 percent of salesCost or latency spikesDecide what you will eat today to keep the trust
04Every table gets touchedEvery stakeholder gets a statusKeep talking until the system is back
05After the shift: what do we changeAfter the incident: what do we instrumentWrite it down while it still hurts
  • On the floor
    The point of sale goes down mid rush
    In an AI rollout
    A model or an API degrades in production
    The move
    Tell the people it affects before they find out on their own
  • On the floor
    The kitchen keeps cooking, the front cannot ring anything in
    In an AI rollout
    One subsystem is fine and the handoff between them fails
    The move
    Go find the broken handoff, not the broken team
  • On the floor
    Comps reach 30 percent of sales
    In an AI rollout
    Cost or latency spikes
    The move
    Decide what you will eat today to keep the trust
  • On the floor
    Every table gets touched
    In an AI rollout
    Every stakeholder gets a status
    The move
    Keep talking until the system is back
  • On the floor
    After the shift: what do we change
    In an AI rollout
    After the incident: what do we instrument
    The move
    Write it down while it still hurts

03The diagnostic

The Last Mile Diagnostic

For a rollout stuck between “we bought it” and “people use it and it pays off.”

Seven questions. It names the bottleneck that is most likely holding you up and tells you what I would do about it first. It runs in your browser. Nothing is sent anywhere and nothing is stored.

1 of 7

Who owns this rollout day to day?

Keys 1 to 4 select. Enter advances. Backspace goes back.

04Proof of work

Two live products, and what each one cost me

No. 01

Ripple News

Product
A news app that rewrites each story for the reader's profile.
Lessons
Three platform rewrites: web, then React Native, then native Swift. I rebuilt the image pipeline after it shipped distorted and missing images, and I rebuilt the content pipeline on compliant sources. Then I cut that pipeline from every 30 minutes to every 8 hours once it was clear this is not a breaking news product, and the run cost came down with it.
No. 02

Yapper

Product
An AI answering service for small trades businesses. It catches the missed call, collects the caller's details, and texts the owner a summary so the job does not disappear.
Lessons
The build was the fast part. Distribution has taken longer: cold email, search ads, and postcards to plumbing and HVAC shops. Nobody in that trade is shopping for AI. They are counting the jobs they missed last week.

05Fit

Where this lands

Role 01

Technical Deployment Lead

  • “CEO of your engagement” is the Sunday I ran with no point of sale. I decided what we ate, who got told, and in what order, and I owned the number at the end of it.
  • “Create structure where none exists” is Ripple. Three platform rewrites, an image pipeline rebuilt after it shipped broken, and a content schedule cut from 30 minutes to 8 hours once the evidence said so.
  • “Define success metrics and measure ROI” is the diagnostic above. It exists because most stalled rollouts I read about never wrote down what done means.
Role 02

Enterprise Account Executive, Retail

  • “Store operations” is ten years of it. Labor, inventory, vendors, a P&L, and the shift that goes wrong at the worst possible hour.
  • “Consultative” is what the diagnostic does. Seven questions, no pitch, and a specific first move at the end.
  • “Retail pain points” is who I sell to now. Yapper's customers are one or two person businesses who lose money every time the phone rings and nobody picks up.
“We urge you not to exclude yourself prematurely.”
I am not.