Hi, I'm Ashley.
South Florida native. Hospitality lifer. Building Whither because the trip planner I wanted didn't exist.
Born and raised in South Florida. As a kid I was sure I'd be a swing on Broadway — dance class most nights, musical theatre obsessions, the whole thing. College arrived and I made the practical choice: hospitality. I'd been immersed in it most of my life and genuinely loved it.
I spent years in luxury hospitality. Took a stint in the title industry when I wanted something more family-friendly. Then came back to hospitality — luxury at Walt Disney World, where I fell in love with the craft all over again.
Nothing about my résumé screams "tech founder." I'm not a CS major. I didn't drop out of Stanford. I'm just a girl with a vision and the passion to fuel it.
The notebook moment
Ten-plus years ago I was traveling to New York constantly. Two of my best friends lived in this incredible Times Square apartment, and I'd crash with them whenever I could.
One night they told me about a class speaker my friend had had in college — a "30 Under 30" type who'd already made a fortune. Someone asked him how. His answer was simple: he carried a notebook everywhere and wrote down every single thing that inconvenienced him during the day. Then at night, he'd sit down and start thinking about how to solve those problems.
So I tried it.
My biggest inconvenience was clear immediately: I wanted to travel — a lot — but I didn't want to do the work of planning it. Researching neighborhoods. Cross-referencing reviews. Comparing flights across five tabs. Asking the right questions to a travel agent who didn't really know what kind of trip I'd actually enjoy. The trip was the reward; the planning was a job.
So I started sketching out — in my head — the travel app I actually wanted to use. Not a search engine. Not another aggregator. An app that knew the kind of traveler I am, sorted every option that way, and let me focus on the part I actually loved — the going.
Ten years of "someday"
I've started this project — in some form — many times over the past decade. A friend who could maybe code. A side gig that ate the savings. A pitch deck I never showed anyone. Every time, life intervened, or I told myself I didn't have the network or funds to make it real.
A few months ago I decided "someday" had become the problem. I picked up the work myself, learned what I needed to learn, hired the help I had to hire, and started shipping the actual product you're using right now.
This is it. Whither — every option, sorted by your vibe.
The vision
Whither is going to be the travel app you keep on your home screen. Girls' weekend, family trip to Italy, honeymoon, buddies' golf trip, retirement bucket-list — whatever the answer to "where to next?" is, it lives here.
I'm building two products under one roof:
- The consumer app — free, vibe-sorted trip planning for everyday travelers
- The B2B SaaS — for travel agents who want modern tools to serve their clients better
Verticals like golf are first. More are coming — honeymoons, multi-gen family trips, group trips, milestone trips. Each one gets the same treatment: built around the kind of trip, not the kind of search.
One stop, every trip. That's the bet.
What's next
Roughly, here's the plan — though plans always change when you put them in front of real people:
- Summer 2026 — 100 active beta testers; product shaped by their feedback
- Fall 2026 — open public beta + App Store launch
- End of 2026 — travel-agent SaaS pilot with a small partner cohort
- 2027 — more verticals (honeymoons, multi-gen, group trips, milestones)
If any of this resonates — and you want to test it, give feedback, or just root from the sidelines — I'd genuinely love to hear from you.
— Ashley