Mobile payment service Cash App is looking to educate Gen Z athletes about NIL deals with a new video series that pits current and future college athletes against each other. 

Cash App today released the first episode of “The Road to NILion$,” a four-part video series that juxtaposes game-show-style challenges with educational conversations. Over the course of the series, its four contestants—Will Levis, former quarterback for the Kentucky Wildcats and an upcoming NFL prospect; Olympian and UCLA gymnast Jordan Chiles; and high school basketball stars Jared McCain and Juju Watkins, who are signed to Duke University and the University of Southern California, respectively—will compete to win the highest amount of “money” through the show’s NIL-themed challenges.

Rather than winning a cash prize, the two athletes who receive the highest scores on the show will each have the opportunity to select a student-athlete for Cash App to endorse with a NIL (name, image and likeness) deal. 

Cash App is no stranger to the NIL space, having previously inked deals with college athletes such as Alabama Crimson Tide quarterback Bryce Young and UConn Huskies basketball star Paige Bueckers. 

In the nearly two years since the NCAA reworked its NIL rules to allow collegiate athletes to profit from their name, image and likeness, brands have increasingly thrown their hats into the NIL ring to strike deals with these athletes. But, because of the relative newness of this marketing area and the surrounding legal gray area, NIL deals can be difficult for both brands and young athletes to navigate.

“NIL has taken the sports industry by storm, and many student athletes are seeking financial guidance within this new and ever-evolving landscape,” said Catherine Ferdon, head of marketing and brand at Cash App, in an email. “Student athletes' ability to market their NIL involvement was effectively turned on overnight, and many athletes have found themselves seeking education around the intricacies of how to monetize themselves and collaborate with brands for the first time.

“As the NIL landscape continues to evolve, this series provides the next wave of athletes with actionable insights from players across a range of sports who have first-hand NIL experiences," she continued. 

Other brands trying to educate collegiate athletes with NIL-related marketing include Nissan. Last year, the automaker's “New Frontiers” effort included a video series featuring football stars sharing tips on how to build personal brands. 

To produce its series, Cash App worked with Uninterrupted, a media company co-founded by LeBron James and Maverick Carter that works to transform athletes into content creators. Uninterrupted has worked on several other video series with brands, including Geico and PepsiCo’s Rockstar Energy Drink.

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The four weekly episodes of the video series will be available on both Cash App's and Uninterrupted's YouTube channels. Cash App will promote “The Road to NILion$” across its other social channels, as well as YouTube TV and in a video spot on Paramount+, Ferdon said. Each episode of the series will also be streamed live on Cash App's Twitch channel, she said. 

With “The Road to NILion$,” Cash App and Uninterrupted sought to “push the boundaries of what financial literacy content could look like,” leveraging athletes with first-hand experience navigating NIL deals to do so, Ferdon said. In the first episode, host Richard Jefferson—an ESPN sports analyst and former NBA basketball player—asks Levis and Chiles about various elements of their experiences with NIL deals between chaotic game show challenges. 

For example, following a game in which the two contestants race to literally balance their budget using a scale and weights that correspond to various sources of income and expenses, Jefferson asks Chiles to discuss how her NIL sponsorships impact how she curates her social media presence.

Cash App deliberately chose athletes to represent various career stages in “the vast world of NIL,” Ferdon said, with Levis recently having wrapped up his career in college athletics; Chiles having competed in the Olympics prior to her collegiate career; and high school seniors McCain and Watkins just beginning to enter the NIL space. 

“The Road to NILion$” is the latest initiative in Cash App’s “That’s Money” campaign, which has leaned into sports and entertainment, featuring the likes of Serena Williams and rappers Kendrick Lamar and Megan Thee Stallion. Cash App, working with agency R/GA, has sought to transform the often-intimidating realm of personal finance into an “easier, more enjoyable” experience for people, Ferdon said. “The Road to NILion$” aims to achieve a similar feat among Gen Z college athletes, she added.

Hear more about how brands and creators are leveraging NIL deals at the Ad Age Creator Summit on April 4 in New York.