Future Focused

Casey Fenton

At 41, Casey Fenton is often referred to as “the grandfather of the sharing economy” for his role in establishing the pioneering global hospitality community two decades ago. CouchSurfing boasts more than 14 million members, hosts, and travelers alike, who live like locals and hail from all over the world. The phrase “couch surfing” tapped into our cultural zeitgeist to such an extent that it was even added to the Oxford English Dictionary in 2008.

This serial entrepreneur has subsequently enjoyed several successful second acts. He is currently the CEO and founder of San Francisco-based Upstock, which aims to innovate how performance-based equity and stock option arrangements are handled. Upstock’s innovative approach allows team members to earn Fortune 1000 equity as an alternative to wages, reducing both payroll expenses and legal costs.

Fenton explains to Gentry that the company endeavors to take the traditional stock option system, “. . . beyond the handshake-and-napkin agreements that often characterize the startup scene. This new method provides an effective way to better build trust, align business interests, and encourage cooperation.”

The Northeast native is a regular on the speaking circuit everywhere from New York to Norway. Silicon Valley, however, occupies a special place in his heart. He points out that, “Although upwards of half my time is spent travelling for business, the Peninsula keeps calling me back. At various times since 1999, I’ve called both Sunnyvale and Menlo Park home.” For entrepreneurs, he adds, “The Bay Area has the ideal combination of incredibly creative people and an unmatched investor ecosystem.”

Among Fenton’s other projects, he’s writing a book on the subject of “Ego Hacking.” It harnesses the power of neuroscience to address fundamental issues of what constitutes our identity and authentic self. The aim is to afford all of us the opportunity to better tap our full potential and live more meaningful lives.

Looking ahead, Fenton believes that the sharing economy will continue to evolve in myriad ways. “We’ll see the utilization of Artificial Intelligence filtering and increasingly fine-tuned techniques,” he predicts. “This will alert us to niche opportunities that we didn’t know existed.”    

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