TailorTrip
Bring a mood, get a decision. A travel planner that does the cognitive heavy lifting.
A shipped product, not a concept: mood discovery through to a saved or shared itinerary, monetized on an affiliate cut of outbound bookings.
What it is
Shrink the decision, don't expand the catalog.
Most travel tools optimize for coverage: more filters, more results, more tabs. TailorTrip turns how you want to feel into a shortlist, a comparison, and a full day-by-day itinerary — then hands off to booking partners instead of trying to own booking.
Built with Sandeep Upadhyay and Shagun Jain. I own product direction, the persona work, and the AI itinerary layer.
The flow
Mood in, decision out
- 1Mood discovery
A short, light capture of how you want to feel. Not a preference quiz.
- 2Smart destination cards
A small set shaped by that mood, not a generic top-ten list.
- 3Cost & decision dashboard
Budget and tradeoffs laid out plainly, so choosing feels safe.
- 4Shortlist & compare
A few real contenders, side by side.
- 5AI itinerary
A full day-by-day plan for the chosen destination.
- 6Booking handoff
Outbound affiliate links. Where TailorTrip stops, on purpose.
Product
What it looks like
“Riya has real income and zero patience for fifteen browser tabs. She wants to hand over the decision fatigue, not curate it.”
Tradeoffs
The deliberate cut
Stop at the decision, hand off via affiliate links
Owning payments and booking is a different, much heavier business. The mood-to-itinerary loop is the differentiated part. Booking infrastructure is a commodity I don't need to own to monetize the decision.
Own the full mood to cost to timing to itinerary loop in one flow
The mood filter alone is copyable in a weekend. What's harder to copy is the whole chain from mood to a booked-feeling itinerary in one connected flow. That's the defensible surface, not any single step in it.
Honest gaps
What isn't built yet
Prompt review is still manual. Quality checks are me reading outputs, not an automated loop.
No graceful degradation yet when itinerary generation runs slow.
“The North Star is a saved or shared itinerary. Monetization is an affiliate cut on the bookings that follow.”