Fenton created the online social hospitality network, the Couchsurfing Project which he began working on in 1999. Couchsurfing currently has over 15 million members worldwide. Fenton served as executive director of Couchsurfing until 2012 and the founding chairman of the board. Since exiting his position as CEO of Couchsurfing, he has also been a part of multiple startups including Sovolve (Wonder App) and Upstock.

Fenton was looking for ways to motivate his team at Couchsurfing & discovered major challenges with traditional equity systems.
He shares that while using stock option based equity, he actually saw productivity decline. Believing that every team should have access to tools that unite & build successful companies, he set out on a quest to repair the broken equity model. Thus Upstock was born. A digital, top-shelf legal equity system that combines performance equity with a visual dashboard. Now workers can watch their equity grow in real-time.