Get Bold in Your Inbox

Jay Walker, the founder of, has another bold idea, a way to easily package travel and accommodation plans to reduce costs.

Upside targets small and medium-sized businesses to offer flight and hotel package deals to reduce travel costs; Walker’s new venture also rewards the individual business traveler with gift cards when he or she is willing to be more flexible with travel times and/or hotel locations.

Currently, Upside is open for business in Beta test mode. A mobile app is on its way.

According to Walker, the timing is perfect to to launch this new venture. Technology—mobile apps, cloud services, large volume data analysis, and an environment where business travelers are willing to make small sacrifices to save money have converged. Referring to this convergence, Walker says, “It was really only in the last year to 18 months that it was clear that all the pieces came together and we could actually finish what we couldn’t before.”

The business traveler goes online to enter all of the travel requirements.  The Upside Flexible Engine piggybacks on the databases of travel clearinghouses like Expedia, adding an analytical layer that looks for every possible way to arrange the trip. Upside presents the best options to the traveler, including how many gift cards each option is worth.  Once the the traveler purchases the package, he or she chooses the earned gift cards from a list of top retailers and restaurants. The gift cards are available to use within 72 hours. Depending upon the package cost, travelers can earn from $50 to $1,000 in gift cards.

Beyond Upside, Walker expects the platform created for the travel market to have a bold impact on other industries as well. Industries such as healthcare and consumer products with a complex, ever-changing data set, where “elasticity trade-offs” can be identified, can use gift cards as incentives for clients/customers willing to wait a little longer for an appointment or a package to arrive.

black and white logo of Bold Wire for Bold Business
The Bold Wire delivers our latest global news, exclusive top stories, industry leading infographics, powerful interviews and bold opinions. It is a free weekly newsletter.

Pin It on Pinterest