Clio Health Champions 2025

Whalar Group's Sixteenth Sports Division Trains Athletes as Creators and Entrepreneurs

Helping clients succeed long after their playing days are through

Sixteenth Sports is out to make athletes the CEOs of their own brands.

The division of talent management company Sixteenth—itself a unit of Whalar Group—launched this month. It aims to function like a boutique agency, developing deep relationships with a select roster of clients.

The goal isn’t “chasing the check or the hot person, but building partnerships and IP,” says co-president Ray Brown. “Let’s partner in something that we own together, where we both have skin in the game. That’s where we’re going.”

Sixteenth Sports is working with athletes in the NFL, NBA, MLB, NCAA and WNBA. Talent includes Tiffany Hayes, who recently signed with the Golden State Valkyeries and is currently playing in the Unrivaled Basketball league. Maxx Crosby, defensive end for the Las Vegas Raiders, is another client.

Both athletes have established strong social media followings—and they’re dabbling in entrepreneurial ventures, too. Hayes serves as CEO of fashion and design company Seyah Renara as well as and Mindzet, which sells headphones and apparel. Crosby is a partner in SAXX underwear.

Sixteenth Sports is also recruiting up-and-comers. “We have our eyes on the high school market and college—catching the new kids that are coming up that can be the next LeBrons,” Brown says.

Sixteenth Sports is investing heavily in educating its clients, giving them the tools that they need to become storytellers, entrepreneurs and creators.

Many athletes who came of age in the era of social media are going into their college careers ahead of the game. “They’ve already set up their IP to be able to monetize off of it based on their lifestyle, based on their training, based on what they’re doing,” Brown says.

But many of today’s pros need more training to get up to speed on how to create content. Sixteenth Sports co-president Alexis Ramos notes that some NFL athletes, for example, are very scripted. “The majority of them are media trained, and if you look at their media responses, everything is by the book, which is great when it comes to professionalism,” she says.

However, being a creator and making videos for TikTok and other social media platforms requires a more personal approach. “For us, it’s really just putting a team around them that makes them feel more comfortable in front of the camera” as themselves, Ramos says, because that’s who people want to see.

There’s no shortage of creators vying for attention, but athletes sport a distinct advantage. “They’re on multiple screens, not just on your social media,” Ramos says. “You turn on the TV, and they’re there. They’re not competing with the traditional creator because of the influence that they have in a household and on a social platform. And that’s where we’re coming in and filling in that white space.”

Sixteenth Sports plans to be in business with its athletes for the long haul, well beyond their days on the football field or the basketball court. “The right people give you longevity,” Brown says. “That’s key for us. That’s beyond your ’15 minutes of fame.'”

Clio Health Champions 2025