The Company
WanderWorth is building the travel industry's community
WanderWorth is a travel-industry events and community business. It brings together founders, operators, creators, investors, media, hospitality leaders, technical builders, and ecosystem partners through public events, curated dinners, and relationship-led programming.
Checkout
A public, one-day Travel & Hospitality Hackathon in New York City. It brings together founders, engineers, AI builders, designers, students, operators, and product builders to create working travel and hospitality products, and it serves as a broad entry point into the WanderWorth ecosystem.
Sunday, August 9, 2026, with 330+ registered attendees across four industry tracks.
Curated travel-industry dinners
Small, invite-only dinners designed to bring together people who rarely sit at the same table. This programming is upcoming.
- venture-backed travel founders
- startup operators
- creators
- journalists and media
- investors
- hotel and hospitality operators
- travel advisors
- tour operators
- service providers
- emerging builders
Ecosystem partnerships
WanderWorth works with travel and technology companies that want:
- developer awareness
- API or SDK adoption
- product feedback
- builder engagement
- technical talent access
- founder relationships
- community distribution
- event sponsorship
- industry visibility
Stay22 joined Checkout as a Gold Sponsor to introduce its SDK to builders, support product discovery, and review eligible project submissions after judging.
How WanderWorth evolved
The current business is not a B2B SaaS platform, a travel planning app, a traditional travel advisory, a consumer marketplace, or an AI itinerary tool. Those were earlier versions of the company.
WanderWorth 1.0
AI-powered B2B SaaS travel platform. Customer discovery generated interest and conversations, but not enough buyer urgency or willingness to pay. I wrote a 35-point GTM post-mortem covering positioning, buyer selection, pricing assumptions, outreach, demo structure, and distribution channels.
Lesson: Interest is not willingness to pay.
WanderWorth 2.0
Travel advisory built around commission infrastructure. The business model had real customer demand, but the founder-market fit was weak. The customers most likely to pay were not the audience I wanted to spend the next five to ten years serving.
Lesson: A viable market is not enough if the founder does not want to build around that customer.
WanderWorth 3.0
Travel-industry events, community, partnerships, and relationship infrastructure. The customer is no longer primarily the traveler. The audience is travel founders, operators, investors, creators, media, hospitality leaders, travel-tech companies, and ecosystem partners.
Lesson: The strongest founder-market fit came from the travel startup ecosystem itself.
Artifact: the original WanderWorth B2B SaaS demo, presented to 500+ people at the Travel Trends AI Summit.
Where WanderWorth is focused
WanderWorth prioritizes dense travel hubs where founders, operators, creators, and industry leaders can reach the room without needing a car. Transit and walkability reduce attendee friction, traffic uncertainty, parking costs, rental-car costs, organizer travel expenses, and the difficulty of stacking meetings. Car-dependent markets currently create more operating friction for this event model.
New York City
Primary market and home of Checkout and the planned recurring dinner series.
Toronto
Strong relationship market through Travel Trends, Dan Christian, travel founders, and existing in-person history.
Chicago
Exploratory market with local founder relationships and potential collaboration.
Montreal
High-context travel-tech market strengthened by Stay22 and the wider travel infrastructure ecosystem.
How WanderWorth expands
WanderWorth brings the travel industry. Local partners bring the city.
WanderWorth brings:
- travel-industry relationships
- brand
- programming format
- sponsor strategy
- cross-city network
- guest curation
- industry context
Local collaborators may bring:
- venue relationships
- local distribution
- city-specific context
- attendee sourcing
- production experience
- local credibility
This is a strategic operating model, not a formal agreement with every named person or city.
Supporting artifact
Airport Friction / Real Founder Metrics, a public post on what an airport disruption revealed about the difference between vanity metrics and the metrics that actually describe a business.
