The Founding Story of Cracked Racquets from Courtside Conversations to a Media Powerhouse

When sharp minds unite with a shared vision and an itch to shake up the status quo, they can carve out a space where there previously was none. That's what unfolded when three driven individuals, Dalton Thieneman (CEO), Daniel Westhoff (CTO), and Alex Gruskin (CCO), combined their talents to establish Cracked Racquets. The visionaries believed that something vital was missing in how tennis stories, especially those outside of the mainstream spotlight, were told.

Cracked Racquets was born out of the founders' realization that there was no serious media coverage for emerging athletes, especially in the junior and collegiate tennis spaces. Traditional outlets focused on already-established legends. Meanwhile, rising stars competing at prominent events remained in the shadows.

Thieneman, a lifelong sports fan from a tennis-focused family, spotted the gap while still in law school. "Knowing this struck a nerve," he shares. "Next generation tennis talents were doing remarkable things. Instead of simply competing for Junior Grand Slam titles, they were winning them! Yet, their stories went untold."

Cracked Racquets stepped in to bridge that gap, combining journalistic creativity with a tech-forward approach to distribution. The company delivers comprehensive multimedia coverage of college and professional tennis, focusing on the nuance, context, and human stories that others miss. The venture leans on four key pillars of live broadcasts, podcasts, events, and merchandise to deliver a full-circle media experience that elevates the voices of athletes from often-neglected communities.

Thieneman brings legal and business acumen to the table. Before founding Cracked Racquets, he was in public affairs and legal consulting, advocating before state governments and regulatory bodies while completing his law degree. He began the company at just 25 years old, balancing coursework with his early forays into entrepreneurship.

Still, it's worth noting that Thieneman's upbringing is what fueled his motivation. "If I need to describe my childhood in one word, I'd say sports. Our house lived and breathed tennis," he says. That foundation gave Thieneman the knowledge and the emotional investment to recognize just how underserved young players were in the broader media landscape.

Thieneman wears multiple hats: chief executive, legal strategist, marketing lead, and business operator. However, he hasn't done it alone. His longtime friend and high school tennis partner, Daniel Westhoff, has been an integral part of the journey from day one. Westhoff, an aerospace engineer by training, was designing private jets before Thieneman convinced him to go all in on the venture. He now leads all technological and production aspects of the company. Whether podcast editing, video production, or designing internal systems, Westhoff's fingerprints are on every piece of Cracked Racquets's technical infrastructure.

Alex Gruskin is the final member of this three-headed machine. His path to the company was unconventional but fittingly on-brand for a venture built on passion. A former political staffer with a photographic memory and a gift for communication, Gruskin cold-DM'd Dalton on social media just two months into the company's existence.

"He praised our vision but pointed out all the wrong ways we're doing our podcasting. We weren't offended. We were actually intrigued. One phone call later, which ran so long I had to skip my law school class, I handed over the full podcasting and content operations to Alex," Thieneman recalls. "I truly believe Alex was born to cover tennis. He will be calling Grand Slams one day soon!"

Gruskin has since become the face of the company's content. He hosts multiple flagship podcasts and commands a massive following among fans. His ability to fuse humor with deep analysis makes him a magnetic presence and a vital part of Cracked's storytelling voice. As the CCO, he crafts the editorial identity of the brand, curating narratives that are intelligent, irreverent, and always resonant.

The path to growing Cracked Racquets wasn't without turbulence, however. The company nearly collapsed during the pandemic, as the global sports calendar came to a screeching halt. With college and pro tours suspended, revenue dried up. Desperate to survive, the team packed into a car and drove more than 20 hours from Indianapolis to Miami to cover a single tennis event that would help keep the company afloat. During that stretch, they pivoted to hosting junior tennis tournaments.

"Those months of managing events, driving relentlessly, and stretching our resources weren't glamorous," Thieneman admits. "But we kept the dream alive. It was bootstrapping in its rawest form. And it worked." Today, Cracked Racquets is respected in the sport and beloved by its community. It elevates rising talent while giving fans an immersive, multidimensional view into the world of tennis and beyond.

The Cracked team is far from done. They're expanding Cracked Media Ventures's reach into new sports, applying the same lens of underserved excellence to other athletic communities. Their goal is to scale both their content and technology platforms in ways that keep grassroots athletes and emerging stars at the center.