Opinions expressed by Entrepreneur contributors are their own.
Imagine coming home from work, turning on the TV, and watching analysts dissect everything you did wrong that day. That’s life for professional athletes.
“People always have opinions about what we can do better,” says beloved Knicks star (yes, star) Josh Hart. “They even have narratives about you and your play.”
But in the podcast era, where anyone can pick up a mic and athletes have direct access to their fanbase, many are taking control of their own narratives. That’s where guys like Matt Hillman come in.
Like a great basketball team, a great sports podcast thrives when everyone plays their role. You need the superstar talent who draws the crowd, the comedic vibes guy who keeps the energy high, and, of course, the obligatory random white guy.
As co-host of The Roommates Podcast alongside Knicks stars Jalen Brunson and Josh Hart, Hillman embraces that role. But in reality, he’s so much more.
“We wanted someone we could see as a long-term partner, be ourselves around, and who wouldn’t make it about them,” Hart says. “We both trust Matt, and to be honest, if we didn’t have a 3rd person, the dialogue might go off the rails pretty quickly,” added Brunson. “You never know with Josh.”
Hillman and Hart’s partnership began in high school, where they played on the same team and lived together. While Hillman pursued Division III basketball, he knew his future wasn’t on the court but stayed connected to the game, often visiting Hart at Villanova — where he also met their future co-host, Jalen Brunson.
After college, Hillman moved to L.A., coincidentally reuniting with Hart after he was drafted by the Lakers. As Hillman built his career — eventually founding and selling his marketing firm, Cut and Sew, to GameSquare Esports — they continued collaborating, including on LightHarted, one of the first podcasts hosted by an active NBA player.
Related: ‘Authenticity is Key’: How Two-Time NBA Champion Jrue Holiday is Prioritizing Mental Fitness and Fashion With Rhone
H(e)art over hype
“Early in his career, it was clear Josh had a standout personality and the potential to be known beyond basketball,” Hillman says. “He had that kind of star quality.”
Recognizing the opportunity, they launched LightHarted, positioning themselves as pioneers in the now-booming athlete media space. “What draws people in is the value of a player’s perspective,” Hillman explains. “Traditional media plays a vital role, but journalists bring their own opinions. Hearing directly from players offers a different level of insight.”
Think about it — who would you rather hear break down a game-winning shot: a TV analyst or someone who was actually on the court?
Back in the LightHarted days, an active player hosting a podcast was a rarity. Now, brands have plenty of options when it comes to athlete-led shows, making it less about landing a big name and more about building a distinct identity.
Hillman believes Roommates stands out because of the organic “brotherhood” he — and especially his co-hosts — share.
“It’s their banter, those unexpected tangents, like when we’re mid-interview and they suddenly start arguing about Josh’s lisp,” Hillman says. “That’s what people love because it’s authentically us. We don’t cut or edit those moments — we embrace them.”
Beyond his on-air role, Hillman serves as a bridge between Hart, Brunson, and potential brand partners. Much of his job involves filtering opportunities, whether selecting the right guests or aligning with brands that make sense for the Knicks duo.
“I’m really big on creating partnerships that feel organic and align with what the guys already do,” he shares.
A prime example came earlier this season when Hart and Brunson showed up in Teenage Mutant Ninja Turtles-themed pregame outfits to promote the franchise’s collaboration with Fortnite.
“It’s about understanding what works for them, especially with their hectic schedules, and making sure partnerships feel natural rather than like a chore,” Hillman says.
Related: “Nothing Is Obvious the First Time”: How This Serial Entrepreneur Is Redefining Sports Media with On3
Pave your own path
He brings that same mentality to Path, the fitness influencer agency he founded last year. While relying on social media for fitness, diet and recovery advice, Hillman noticed that many top creators — despite having millions of followers — lacked management.
Recognizing that fitness influencing had emerged as a post-COVID phenomenon, with trainers shifting to digital content after losing in-person clients, he saw an opportunity. He launched Path to help these creators navigate the business side of their platforms, leveraging his experience with professional athletes to support the rapidly growing health and fitness space.
Though Roommates and Path may seem like separate ventures, Hillman sees them as deeply connected.
“When we bring a brand onto Roommates, I build relationships that can extend to Path and its influencers, and vice versa,” he says. “Ultimately, the more Roommates grows, the better it is for the show, the guys, myself, and everything in our orbit — including Path.”
Image Credit: The Roommates Podcast
What began as a way for Hart and Brunson to showcase their personalities has evolved into a lucrative venture for everyone involved — from the players themselves to the brands they collaborate with.
“The most eye-opening experience for me was our live event in Central Park,” Brunson says. “We had 5,000 people come out to support the show, and they didn’t even leave when it rained.”
Although they’ve joked about podcasting being their “real job,” both Hart and Brunson recognize that the podcast is only possible because of what they do on the court. Despite its success, they make a conscious effort not to take it too seriously.
“First and foremost, we want to keep enjoying it,” Brunson says. “That said, our eyes have really been opened to Roommates’ potential as a business, and we’re excited for what’s ahead.”
