Inspiration

Booking a place to stay takes a few taps on Airbnb, but booking a jet ski, a skydive or an escape room still usually means a phone call, a contact form, or waiting on an email reply. We kept losing weekend plans to "we'll get back to you." We wanted booking an activity to feel as easy as booking a stay: pick a time, pay, done.

What it does

Outset is Airbnb for activities. Guests browse local experiences like jet skis, skydiving, karting, escape rooms and fishing charters, see real photos, prices and open times, and book instantly. Every listing has an AI assistant that answers questions about that activity and says it will check with the host when it doesn't know, instead of guessing. Hosts get a dashboard to accept bookings, block off days, edit their services and prices, and track payouts.

How we built it

The guest app and host dashboard are built with Vite, React and TypeScript, with a Node and Hono API on Render and Neon Postgres for bookings and host profiles. The desktop site follows Airbnb's browsing patterns, and on a phone the same app runs full screen like a native app. Bookings lock each time slot as they are made, so two guests can never take the last spot. The listing assistant uses Claude and is limited to the facts on that listing.

Challenges we ran into

The hardest part was trust: if the price or open time a guest sees is wrong even once, instant booking stops meaning anything. Getting the AI assistant to say "I'll have the host confirm" instead of making up an answer took a lot of iteration. We also had to make host sign-in links secure, replacing links that never expired with signed ones that do. Fitting a full host dashboard into both a desktop layout and a phone screen was a design challenge of its own.

Accomplishments that we're proud of

Guests can browse about 59,000 activities across the US and Canada. Booking takes a couple of taps, from picking a time to confirmation. Hosts get a complete dashboard covering bookings, calendar, services, availability, listing and payouts. The assistant never invents a price, a policy or an open slot.

What we learned

People want to book, not inquire: every extra step between "that looks fun" and "booked" loses them. An AI that admits what it doesn't know earns more trust than one that always has an answer. Copying patterns people already know, like Airbnb's listing cards, made the app feel familiar from the first screen.

What's next for Outset

Next we bring on our first hosts and switch on instant booking for their activities. After that come payments, text message confirmations and calendar sync with the tools hosts already use. Then we grow city by city, starting with Tampa Bay.

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