Running three brands from a hilltop town in Tuscany — with AI as my team
Cortona sits at 600 meters above the Valdichiana. On a clear day you can see for 60 kilometers. The town has been here for 2,500 years. My businesses have been here for two.
I run MyTuscanDays — a private experience platform for tourists and expats. I run Arpi Woodworking — olive wood craftsmanship with a physical shop and international sales. And now I run Arpi Digital — an AI operations consultancy.
Three brands. One person. No employees. No office. Just tools, judgment, and a very clear sense of priorities.
The actual stack
Claude is my primary AI — for writing, strategy, analysis, communication, and operations management. I use it every day, for every brand, in three languages.
Squarespace hosts MyTuscanDays and Arpi Woodworking. Netlify runs my pricing tools. SumUp handles payments. Revolut manages cash flow with pocket allocation rules I set once and never touch.
That’s most of it. The rest is judgment.
What AI actually replaced
Not creativity. Not relationships. Not local knowledge — the kind you only get from living somewhere, from knowing which road floods in November, which partner delivers and which doesn’t.
What AI replaced: the volume work. The drafts, the translations, the scheduling logic, the pricing calculations, the first version of every document. The things that used to take hours now take minutes. The time I saved went into strategy, into clients, into the work that actually matters.
I’m not a tech company. I’m a person with businesses in a town in Tuscany. AI is how I compete with people who have teams.
Why Cortona matters
Location is not an accident. Cortona is the context for everything I do. And the AI consultancy exists because local businesses here have exactly the same operational problems as businesses everywhere — and almost no one is helping them solve it.
That gap is the opportunity. And it starts here, on this hill, in this town.
Editor’s note (added 2026-06): Since this piece was published, CortonaInsider.com has launched as a fourth brand under this same operating model — Cortona’s English-language digital gateway.
If you’re American and already running something here — a property, a business, a life split across two continents — or thinking about it, this is exactly the operating model I’d point you to. It’s not theoretical. It’s what pays my bills.