🏆How Two Brothers Turned a YouTube Idea into an ESPN Deal

Together with

From Law and Music to Media Disruption

Cody and Cole grew up outside Toronto, hockey fans and hoopers. “We played basketball at a very competitive level when we were younger,” Cody said. “It’s carried through everything we do today.” Cody went on to attend USC. “Originally I was pre-med, I was going to be a doctor… that didn’t last very long.” He eventually pivoted toward law school at USC and thought, “I’m in LA, I’m in Hollywood, I’m going to work in the entertainment business.”

Cole, meanwhile, was all in on music. “Went to Syracuse for college… specifically in the music business program… I was working with artists, songwriters, and producers.” When Cody pitched him the idea of managing content creators and YouTubers, Cole said, “I initially said no… I didn’t really see the vision.” But that changed quickly. “After taking a week or two of seeing the YouTube landscape at the time… I really liked that idea to apply that to sort of a totally different industry – adjacent, but different.”

Turning a Creator Into a Company

In 2020, they cold-emailed Kenny Beecham, whose basketball commentary on YouTube was quickly gaining steam. They didn’t just want to help him land brand deals. They wanted to build something bigger.

“When Kenny was under a non-compete, we launched an email newsletter,” says Cody. “It was the only content he could be part of, and we scaled it to 50,000 subscribers.” That set the stage for what came next: Enjoy Basketball, a full-blown media and lifestyle company launched around Kenny’s brand. It started as a newsletter but exploded into podcasts, YouTube shows, sold-out live events, and strategic collaborations with ESPN, Omaha, and more.

Peyton Manning, ESPN, & Adam Silver

One of their most validating moments came during a promo shoot with Peyton Manning to launch Numbers On The Board, a podcast they built with Kenny. It was filmed in Manning’s office – and to their surprise, he wore an Enjoy hat on camera. “He didn’t have to, but he did,” Cody says. “That moment legitimized everything we’d been working on.”

The partnership with Omaha Productions and ESPN led to something rare: a digital property moving to linear television. Numbers On The Board now airs weekly on ESPN2. “Usually it’s the other way around,” Cody says. “To go from YouTube to linear cable? That’s rare. It’s a testament to the community, the content, and the brand we’re building.”

A few weeks later, NBA Commissioner Adam Silver appeared on the show. It was a validation of their purpose. “He echoed our mission – uplifting basketball, telling positive stories, and building a media brand that celebrates the culture,” Cody says. “It’s one thing to believe in what you’re doing; it’s another when someone like that affirms it.”

From Hoodies to Culture Drops

While Cody drives the content engine, Cole leads the brand’s lifestyle and apparel business. They’ve sold out over 12 product drops and collaborated with Jimmy Butler’s Bigface Coffee. “That took over a year to get done,” Cole says. “But seeing Jimmy in our gear in the tunnel? That was a vision board moment.”

Each launch builds the cultural footprint of Enjoy Basketball, blending fandom, fashion, and identity in a way that resonates with the next generation.

What It Takes to Build Something

When it comes to building a brand like Enjoy, Cody and Cole have learned it’s not just about working hard – it’s about working smart, being relentless, and staying deeply connected to the mission. “The people we’ve seen succeed, especially in this space, they’re obsessed with the craft,” Cody says. “It’s not just passion, it’s passion paired with discipline, paired with vision.”

That’s something they’ve seen firsthand in Kenny. “He’s maniacal about being great,” Cody adds. “He puts in the hours, he knows his voice, and he never mails it in.” That level of intentionality is what turns a creator into a company. They’ve taken the same approach themselves. When a deal seemed dead, they didn’t walk away. “If the front door’s locked, we’ll find the window,” Cody says. Whether it was cold emailing, reworking the pitch, or making another phone call, they kept going until things clicked. It’s that mix of creativity, persistence, and clarity of purpose that’s helped Enjoy Basketball break through.

Advice to the Next Wave

Working in sports doesn’t require following the traditional playbook anymore. Cody and Cole are proof of that. “It’s the best time to be building,” Cole says. With social platforms, AI tools, and digital access leveling the field, they believe anyone with vision and drive can carve out a lane. Whether it’s launching your own content, selling for creators, or just experimenting with ideas, there’s room to make something real. “You don’t need permission anymore,” Cody adds. “You can start anywhere. It may not be exactly what you want at first, but it can lead you there.”

Learn AI in 5 minutes a day

This is the easiest way for a busy person wanting to learn AI in as little time as possible:

1. Sign up for The Rundown AI newsletter

2. They send you 5-minute email updates on the latest AI news and how to use it

3. You learn how to become 2x more productive by leveraging AI

Sign up to start learning.

Subscribe to Premium to read the rest.