[1] He is the co-founder of WEconnect, a healthcare information technology company with a platform designed to aid addiction recovery, and currently the head coach of the Washington Kastles of World TeamTennis.

After losing in the first round of the 1999 US Open, feeling the pressure of work and family responsibilities (his son, William, was born a few weeks after the tournament), Jensen found himself in the throes of addiction.

In 2016, Jensen, Tudor, and business owner Jen Mallory co-founded WEconnect, a web application platform designed to assist patients with addiction recovery after treatment.

Described as a "social-purpose corporation", WEconnect's business platform is centered around providing "accountability for an individual's recovery activities by closing the gap in communication with their support network."

At least one major player appears at some point in the episode, and there is usually a brief segment about where enthusiasts of the game can play when in town, but the show's content mainly features Jensen attempting to navigate the city's sights, trying exotic food, and interacting with locals in his unique style.

Many episodes also feature a scripted opening sequence, such as Jensen being made to walk the plank by the pirates of Treasure Island in Las Vegas, being psychoanalyzed by Sigmund Freud in Vienna, and impersonating James Bond and Crocodile Dundee in London and Melbourne, respectively.