The prediction
Operator websites become meaningless.
Today, I’m trying a different sort of receipt. The sort that involves making wild predictions. (Y’all know I love me a hot take.)
At AI speed, an annual prediction is pretty much historical fiction. A year is a long time to leave a hot take unsupervised. Each month, I’ll add one prediction and revisit earlier bets when there’s something to report.
After a year, we’ll have 12 bets and a paper trail. Predictions now. Public receipts later. We’ll find out whether I saw the future or just need more sleep.
My prediction: Guests will prompt your experience inside an agent. As more of their lives happen inside a prompt, the website becomes less valuable as the place they discover and choose you.
The opportunity
Anticipation becomes the new discovery.
The agent will own the conversation around discovery. But you can own anticipation. Use the time between booking and arrival to turn “the stay my agent found” into “the destination I can’t wait to go.” Your category gives that relationship somewhere to start.
What needs to happen
Bring the experience into the conversation.
Technology companies are already creating interactive interfaces inside agent conversations. The tooling exists to bring your data, your workflows and an interface into the chat. Guests can prompt your experience instead of clicking through to your website.
What needs to happen? Your prospective guests shouldn’t have to suggest installing a plugin for an experience they don’t yet know exists. Once their agent reliably suggests your plugin when it improves the answer, and connecting it is seamless, game over.
A guest should be able to ask for what they want, have the agent suggest the relevant connection and get started without a technical setup project.
The clock and the receipts
Six months. A bet with a paper trail.
How quickly? Tech companies building tools for developers are already doing this. Within six months, I expect guests to be prompting your experience in their agent of choice. Stay options, itineraries and the things that make your category yours, all inside the conversation.
What will I be watching? How many travelers choose their stay inside an agent before ever visiting the property’s website.
Designers, investors and operators
Build the relationship before arrival.
What this means for designers: Extend category design beyond the physical assets into the digital assets. Help operators build anticipation after the booking and before arrival, using the moats that make their category defensible. Design how the guest starts experiencing that transformation before they ever set foot on the property.
What this means for investors: Evaluate an operator’s anticipation strategy after the booking is captured. How robust are those assets? Does the operator have the data infrastructure to tailor the anticipation sequence to each guest? Treat anticipation as an asset and ask for its receipts: does it sell relevant add-ons, reduce preventable cancellations or bring guests back? A booking starts the relationship. Find out what the operator earns from building it.
What this means for operators: The guest guide can no longer be a static asset. It needs to evolve as guests prepare for their stay, bringing your promised guest transformation to life at every step. You do your category a disservice if it’s limited to a PDF of restaurant recommendations and a Wi-Fi password.
Menizei is the lab
The guest guide gets a new job.
My experiment: I’ve reimagined what the guest guide looks like for Menizei guests. I’ll share the receipts in an upcoming article.
Agree or disagree with this prediction? I’d love your take. I respond to every email.
An announcement
Designing Your Hospitality Unicorn.
I asked what would help you design and build your stay. You came back with notes. My kind of people.
My next workshop will be Designing Your Hospitality Unicorn, and your feedback prompted me to try a different format: a two-hour virtual session each week for four weeks.
All Wednesdays, 10:00 AM–12 noon PT.
- 28 October 2026
- 4 November 2026
- 11 November 2026
- 18 November 2026
Your message was clear. You want to enter the new year with a well-formed concept. Not another mood board.
We’ll define your category, design your guest transformation and build a design system for your project. Expect weekly assignments, live feedback and collaborative jam sessions. Come ready to work.
The workshop will be capped at eight seats, ideally four operators and four designers. If you’d like first dibs when applications open, email me for first dibs.
And if you don’t yet have a well-defined category that you uniquely own, keep an eye out for the workshop. That’s the work that makes your property defensible as AI changes the game. Ask for first dibs.