The Intersection of Centre Court and Business Grit: Where Dalton Thieneman Channels Tennis Spirit into Media Innovation Playing tennis and building a business seem like pursuits worlds apart. One is played out on manicured grass courts, the other in spreadsheets, strategy decks, and late-night calls. However, both share a reliance on grit, adaptability, and nerve. Much like stepping up to serve on match point at Wimbledon, launching and scaling a venture demands preparation and belief.

Playing tennis and building a business seem like pursuits worlds apart. One is played out on manicured grass courts, the other in spreadsheets, strategy decks, and late-night calls. However, both share a reliance on grit, adaptability, and nerve. Much like stepping up to serve on match point at Wimbledon, launching and scaling a venture demands preparation and belief.

Dalton Thieneman understands this deeply. As a lifelong sports enthusiast and the CEO of Cracked Media Ventures, he knows why instinct must be trusted when there's no time for guarantees. Now, as Wimbledon captures the world's attention once again, Thieneman isn't just watching the tournament. He's living its essence through every decision he makes in business.

Thieneman's roots in sports run deep. He and his co-founder, Daniel Westhoff, were part of a high school team that clinched multiple state team championships. Similarly, co-founder Alex Gruskin won a Tennis On Campus National Championship. These feats required fierce competitiveness and a refusal to fold under pressure.

Interestingly, Thieneman didn't grow up as a prodigy on the court. He picked up tennis later than most, coming from a multi-sport background. He was known for staying on court for hours if that's what it took to win a single point. Looking back, it was an early sign of the tenacity that he exemplifies today.

Before stepping into the media and tech space, Thieneman was an attorney and lobbyist. With a legal degree and years of experience representing clients across industries, from education and tech, tourism and public safety, he's been familiar with high-stakes environments. Unexpectedly, his passion project in sports media, a podcast and blog for college and junior tennis fans, turned into a full-fledged broadcasting company. It now provides coverage across an expanding roster of emerging sports, including pickleball, paddle, and volleyball.

Thieneman's multidimensional perspective has helped him realise that the essence of BIZ Experiencesship closely mirrors the competitive soul of tennis. "In both arenas, success depends on more than just talent," Thieneman says. "It demands the kind of grit that makes you play four hours to win a single match, or stay up all night building a product no one's certain will work."

At Cracked Media Ventures, Thieneman and his team didn't have broadcasting degrees or polished media training. However, they had fire. When the pandemic shut down every traditional revenue stream, they didn't wait. They drove 22 hours to Miami to cover an event, betting everything on keeping the lights on. That risk set the stage for what would become a calendar of several junior events annually. "We didn't land where we are right now gracefully, but whatever we did was effective," Thieneman states.

Indeed, Thieneman doesn't shy away from complexities. He admits that he plays to win. In both sports and business, the reality is often murkier than the textbooks suggest. Winning sometimes demands navigating the grey, adapting mid-match, sticking to the game plan, or throwing it out entirely when conditions shift.

Doubles players know this well. "Success depends on trusting your partner, adjusting in real-time, and never letting ego get in the way," Thieneman says. The same principles apply in a business, where collaboration and trust are everything. For Cracked Media Ventures, that trust has been pivotal as Thieneman, Westhoff, and Gruskin navigated pivots and setbacks.

Adaptability has always been the bedrock of Cracked Media Ventures' growth. The company began under the name Cracked Racquets, an effort to fill a gap in tennis coverage. It has then evolved into a broader sports tech company under the Cracked Media Ventures umbrella, which now delivers live-streaming broadcasts across multiple sports markets.

Thieneman emphasises that malleability is not optional in media. It's survival. As platforms and technologies evolve, so too must content creators. "Even now that we're garnering so many followers, I always tell the team to keep improving. Celebrate the milestone tonight, then wake up tomorrow thinking about the next match," he remarks.

That forward-thinking mindset is what's driving Thieneman's view of the future. He argues that sports media is no longer something one passively watches. It's becoming something one experiences. "We're entering an era defined by AI-enhanced storytelling, multi-screen interactivity, and immersive engagement. For example, fans don't just tune into Wimbledon on one screen. They're pulling up stats on another, scrolling commentary on a third, maybe rewatching a crucial point in slow motion somewhere else entirely," Thieneman states.

This fragmented but rich ecosystem is where the future lies, and Cracked Media Ventures is positioning itself at the centre of that shift. The company's recent collaboration with ATP Tour signifies alignment with the forces reshaping how sports are consumed and monetised. It's a glimpse of what's possible when media and technology meet strategy and hustle.

Ultimately, Thieneman believes the convergence of sport, media, business, and law will only intensify. From regulatory decisions around AI to new models for athlete revenue, the future will be shaped by those who can navigate across these disciplines. It requires building ecosystems that respect both the craft and the context. And that, Thieneman suggests, is where Cracked Media Ventures will thrive.