Restaurants
AI read the lease but could not divide a pie
ChatGPT read a 45-page lease in three minutes for Dr. Nikki Siso, then failed at recipe arithmetic. The failures sort by information, not difficulty.
For business owners and execs
What's not working
Bought, deployed, and quietly abandoned. What it cost to find out, and what the operator does instead.
Construction
Get your house in order before you buy any AI
Annija Eizenarma on the records legacy operators need in order before onboarding, and why missing them turns an AI rollout into months of assembly.
Public relations
Can AI write comms copy that anyone remembers?
Not from scratch, says Sam Polstein: models have no emotion and a recognisable tone. Three mitigations he uses, and the fifty percent draft to never send.
Construction
How to judge an AI vendor when you cannot judge the software
A $20 million business run on sticky notes cannot tell a real AI product from a wrapper. Annija Eizenarma on what to evaluate instead of the technology.
M&A advisory
The $5 million valuation on $125,000 of net profit
An AI report valued a business at $5 million on $125,000 of net profit by counting expenses as assets. The broker's guidance was a 3-4x multiple.
Hospitality
Why AI personalization fails for luxury hotel guests
The privacy paradox, in Sofiane Ghorbel's words: the better the personalization, the more data AI needs from the clients least willing to give it.
Yacht charter
The client who circled ChatGPT's answer in pen
A charter client asked ChatGPT if he could anchor in 25 knots of wind, was told yes, and overruled the captain. What it costs the operator.
Construction
The AI pilot that dies in month three of data collection
Integration costs of $500,000, contracts running five to ten years, and onboarding that takes months: why AI deals in legacy industries die before output.
Health & wellness
Forty-five minutes of disclosure, and then no report at all
A client finished a forty-five-minute AI health assessment and got silence. What broke, what it cost, and five checks before you ship one.
Restaurants
The $30,000 mistake AI could not warn her about
Dr. Nikki Siso asked AI how to open a restaurant. It found the forms but not the order, and the sequencing error cost a month and $30,000.
Retail & events
When AI writes the flyer, the letters come out wrong
Luisa Ramirez uploads an image, asks for a flyer, and gets words that don't match what she typed. Her fix is to move everything to Canva.
Retail & events
The friendly draft that keeps reverting to generic
Sara Rojas gets the register she wants, then loses it. She has to re-prompt, the version she liked is gone, and nobody told her settings existed.
The Operator Brief
What actually worked, from people running the business
One operator interview a week: the tools they kept, the ones they dropped, and the numbers behind both.
You are joining the operator brief. Building AI products instead? Compare both briefs.