Guess Where Trips: Crafting Self-Guided Surprise Road Trips (w/ Jessica Off)

Mitch Bach speaks with Jessica Off, founder of Guess Where Trips, an e-commerce company creating physical and digital surprise road trips for customers across Canada and the U.S.

Jessica is a serial travel entrepreneur, including work at G Adventures. In this episode, she talks about what led her to start an e-commerce product-based travel business, after looking into tour operating and multi-day trips.

This episode will give tour operators the inspiration to think about ancillary product revenue streams that can complement their in-person business, utilizing the same destination knowledge and supplier connections to offer experiences to a new customer base!

• Visit Guess Where Trips home page
• Episode show notes

We talk about:

• the design thinking behind crafting self-guided tours
• why the element of surprise is so crucial to the experience
• her experience working with content creators
• how B2C trade shows have worked out for her trying to sell her product
• why she decided to ditch multi-day surprise trips
• the importance of collecting email addresses at trade shows
• finding the right market for the trips, and why big cities don’t work
• working with local vendors to support them