Building a second brain for your tour company.

Ask ChatGPT to write an OTA description for your walking tour and you'll get something that sounds like every other walking tour on the internet. Not because the model is bad, but because it doesn't know anything about you. It doesn't know your margins, your best-selling tour, the way you talk to guests, or the fact that you'd never call them "clients."

The fix isn't a cleverer prompt. It's a second brain.

What a second brain actually is

A second brain is a single, structured store of everything about how your tour company runs, written down in one place that any AI can read. Not in your head, not scattered across ten spreadsheets and a WhatsApp group. One source of truth.

Think of it as the briefing document you'd hand a brilliant new hire on day one — if that new hire could read it in three seconds and never forget a word. Because that's effectively what you're doing: onboarding the AI to your business once, so you never have to re-explain it again.

Why this matters more for tour operators than most

AI is only ever as good as the context you give it. A chat window starts every conversation knowing nothing. So each time you ask it to write a listing, answer a review or draft the Monday report, you're either re-explaining your business from scratch or getting generic output that could belong to anyone.

With a second brain, that flips. The same request now produces a listing with your actual hook, your real price and your tone of voice. The guest email sounds like you. The report uses your numbers. The model stops guessing and starts working from fact.

What goes in it

Here's the part people get stuck on, so let me be specific. A tour company's second brain should hold the things that actually shape a decision or a piece of writing:

• The numbers. Guide day rates and costs, the shape of your P&L, occupancy and load factors by tour and season, historical booking data, margins, and how you price. This is what lets an AI reason about a real decision — "should we run the sunset tour on Tuesdays in November?" — instead of guessing.
• The brand. Your tone of voice, brand guidelines, the words you use and the ones you'd never touch, your story and what you stand for. This is what makes AI-written copy sound like you and not like a press release.
• The product. Every tour: what it is, the itinerary, group size, duration, price, what makes it special, the logistics, and a proper FAQ for each. The more concrete this is, the better every listing and answer becomes.
• The operations. Your suppliers, your booking system (Bokun, Rezdy, FareHarbor), and your policies on weather, cancellations, groups and accessibility.
• The guests. Who actually books you, where they come from, and the themes that come up again and again in your reviews and feedback.

You don't need all of it on day one. But over time, everything that pertains to running the company should live here.

Why a markdown file (and then Obsidian)

Here's the bit that surprises people: at its simplest, the second brain is a plain text file. A markdown file — a .md — is just text with light formatting: headings and bullet points. Nothing fancy, nothing to buy.

I recommend markdown for one reason above all others: it's portable. Plain text is the native language of every large language model. A markdown file drops straight into ChatGPT, Claude or your own agent and gets understood perfectly, with no conversion and no lock-in. Your business knowledge never gets trapped inside one company's product.

Start with a single file. When it outgrows one file — and it will — move it into something like Obsidian. Obsidian is a free app built on top of plain markdown files, so you keep all that portability but gain folders, links between notes and a proper structure. Because it's still just markdown underneath, you can hand the whole thing to any AI whenever you like. Build it once, use it everywhere.

How you actually use it

Once it exists, the workflow is simple. Want an OTA description? Give the AI the relevant slice of your second brain and ask. Want a guest email, a Monday report, an ad, a new tour page? Same move. The model writes with full context, in your voice, using your facts. You go from "write me a tour description" and getting mush, to getting something you'd publish with a light edit.

And if you're running an agent (I wrote about that here), the second brain becomes its long-term memory — the thing it consults before it does anything on your behalf.

The honest bits

Two warnings, because I don't like frictionless articles.

First, it's only as good as you keep it. A second brain that's six months out of date will confidently tell your AI the wrong price. Treat it as a living document — five minutes whenever something changes beats a rewrite once a year.

Second, mind what you put in it. If you're pasting your second brain into a public chatbot, don't load it with guest personal data, card details, or anything you wouldn't want leaving the building. Keep the sensitive material in your own tools and let the second brain hold the knowledge, not the secrets.

Where to start

Open a blank markdown file. Give it five headings: the business, the brand, the product, operations, guests. Spend one hour filling in what you already know off the top of your head. That single hour will do more for the quality of your AI output than any prompt trick you'll ever learn.

Then, next time you ask AI to write something for your tour company, hand it the file first.

This is one piece of a bigger picture. For the wider view, read my guide to AI for tour operators, or the practical starting points in 5 ways to start optimising your tour company with AI.