Ep. 255 — 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!

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