Alma Matters: Three Windermere Preparatory School alumni found sporting agency

Attending Windermere Preparatory School allowed Class of 2016 members Parker Davis and Sully Zagerman the freedom to explore their athletic passions outside of academics.

But being a Laker gave them more than just freedom to explore their interests. The small community allowed them to connect with teachers, faculty and their classmates on a deeper level than they would have at a larger school. 

Davis and Zagerman met in sixth grade. Their friendship grew through their shared love of sports, and they met Noah Pollock, a Class of 2015 WPS alumnus, three years later.

Pollock and Zagerman went on to attend Florida Atlantic University together, then went to law school together at Nova Southeastern University Shepard Broad College of Law. During those years, Davis went on to study sports industry management at Georgetown University in Washington, D.C. 

Although the three weren’t in the same state, they remained in touch.

And if it weren’t for their early years together as Lakers, the three alumni never would have co-founded Dotted Line Sports, an agency specializing in representing athletes at the high school and college levels and the NFL by providing them support throughout all pathways of their careers. 

The idea was launched as the trio’s individual career paths began to converge. 

ATHLETES SHAPING ATHLETES 

Pollock and Zagerman were discussing launching their own law firm, while Davis was studying for the NFL Players Association certification exam. 

When Davis passed his certification exam, which was 60 questions in three hours and encompassed all of the rules and regulations, he understood exactly how contracts work, what happens if a player gets injured and all the regulations that make up the NFL. 

The three reconnected and decided to begin Dotted Line Sports in 2023 with a focus of representing NFL players. But together, they saw an opening in the growing world of Name, Image and Likeness opportunities and athlete representation greater than simply the NFL and decided to expand their idea.

“About 98% of NFL players have agents,” Davis said. “Now that there’s money involved in high school and college sports, we view it as these student athletes need representation as well, and we come into it from the perspective of trying to bring that professional representation that NFL players get to the college side.” 

The founders believe their backgrounds as former college athletes helps give them an advantage in understanding what challenges the athletes face on a daily basis. Davis played as a point guard for Rollins College, while Zagerman was a team captain for FAU’s golf team. 

“College athletics is a completely different world,” Zagerman said. “It’s a business within the school, and the athletes (who) go through that … like to be able to talk to somebody (who) has been able to balance and understand what they’re about to go through and anticipate that and help them.”

Windermere Prep also helped the partners adjust to college life. Unlike Zagerman’s college teammates, he didn’t experience culture shock when he stepped onto FAU’s team as a freshman. Windermere Prep allowed both Zagerman and Davis to leave early to practice, balance their travel schedules for athletics and even helped set up college visits. Zagerman described it as a “full-package service.” 

The experiences encompass exactly what they are trying to give to current high school and college athletes. 

Davis said their main function as agents is to negotiate the athletes’ contracts — whether that be through revenue-share deals or marketing endorsements. But beyond that, it is to make sure their clients and their families have a full picture of the business implications of the sport. 

“A goal would be that we can have these clients and families come back to us and say that we took the stress away,” Zagerman said. “We truthfully helped their kid grow from the summer camps or varsity football all the way up to the league and that they never had a worry; they never had a doubt. We were able to help them through every process and every instance, and it’s just nothing but smiles as they’re watching their kid on Sundays.” 

Through the past three years, Davis remembered being nervous to first call athletes and begin to build the relationship with them. But now, he’ll even make a call after having a tough day at practice. He has become not only an agent but also a therapist. He’s found it rewarding to build the emotional relationship with rising athletes. 

Davis works on the recruiting side of Dotted Line Sports and the day-to-day operations. He focuses on maintaining client relations, such as last year negotiating revenue-share contracts and helping athletes go through the transfer portal process. 

Zagerman mostly helps with the finances and the operational side of Dotted Line Sports, while Pollock is big on the high school side of recruiting. They both also are lawyers, which helps to build the reputability of the agency. 

“One of the most valuable things that you can have at an agency is the in-house lawyer representation, so we know we’re confident that if anything arises legally, we’re going to be covered in that sense,” Davis said. “Combining my passion for recruiting and the NIL side and NFL side of things with them doing recruiting as well and having their legal expertise, it works out perfectly for us.” 

The athletes’ parents have been especially excited about the two in-house lawyers to help their children. 

Appealing to both the athletes and parents can be one of the trickiest parts of the job. Zagerman said the parents’ ears are different than the kids’ ears. The successful 16-year-old athletes want all of the flashy items and money value, but the parents’ top concern is their safety. 

By putting their heads together, they’ve been able to find success in their growing agency since they’re unified in their goal to be a professional representative to student-athletes. 

“We’ve gained friends through this more than clients,” Zagerman said. “That’s the biggest thing. We’ve gained some lifelong friends and we’ve been able to see them succeed and continue to see them succeed.” 

ALWAYS A LAKER

Throughout all of the business’ growth, the founders said their strongest asset remains the friendships that started years ago at Windermere Prep. 

Davis admitted he initially was nervous working with them. The first internal calls and meetings felt unnatural to talk about with his close friends, but over time, they became accustomed to it. 

Zagerman had a different take. If someone told him in sixth grade that he’d be working with his friends from then, he wouldn’t have blinked an eye. 

“My dad ingrained this in me that it’s about who you know,” Zagerman said. “That’s just how you get by in life. It’s about who you know, and so I knew at some point, I’d be using these connections to further a business world and to further my own life and everyone else’s life around me.” 

But the three Windermere Prep alumni are grateful for the school for more than just allowing them to connect with one another. They still are in connection with faculty and other classmates, as well. 

Davis said coaches will reach out to them if they know an athlete looking to prepare for college or faculty members if they know someone. He said the connections through Windermere Prep always will be valuable. 

“That’s why you go to a school like Windermere Prep,” he said.