- December 9, 2025
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It’s hard to chat with JB Greer and not think of Jerry Maguire.
The 1996 hit movie starred Tom Cruise as hotshot sports agent Jerry Maguire. The flick introduced audiences to a fictional yet-felt-real world, where cutthroat agents tried to outdo each other in a race to get clients lucrative contracts. The movie, in addition to a scene where Maguire quits his top-shelf firm to go on his own — with no clients — also dropped some classic lines still uttered today, 30 years later. “Help me help you,” is one. “You had me at hello” is another. And, of course, “Show me the money.”
The co-founder of Tampa-based Hustle Sports, Greer sees the obvious Maguire comparisons — though he was four-years-old when the movie came out. Greer was a certified agent for Major League Baseball players for seven years at industry giant Octagon, based in Chicago. He left Octagon in July 2024 to start his own firm. He had zero clients.
“There are some similarities to what happened in that movie,” says Greer. Enough similarities that Greer, 33, had his wife watch the movie, “so she can understand” why people often make the comparison. (Emily Greer fell asleep before it was over, he quips.) “But I don’t want to be flashy (like Jerry Maguire.) I want to be much more low-key than that movie.”
Low-key doesn’t mean unsuccessful.
In his first 16 months running Hustle, Greer has grown the business into a David-like agency in a world of Goliaths, such as Octagon, Creative Arts Agency and Roc Nation Sports. One key to Hustle’s niche: it only does athlete marketing representation; it doesn’t negotiate contracts between players and teams. Instead, Hustle finds deals for its clients to represent brands of all sizes, something Greer says is rarely a focus at the big firms.
“We are blazing a trail in that no agency has started out like we did only for baseball players,” Greer says. “I don’t think there’s anybody doing anything like us.”
Hustle has signed 12 clients so far, starting with eight MLB players. The first client was Bobby Witt Jr., a star shortstop for the Kansas City Royals who was the American League MVP runner-up in 2024. Hustle has since signed Witt to marketing deals with brands including Whataburger, Wilson and Under Armour. Others who have followed Witt include Julio Rodriguez with the Seattle Mariners and Brent Rooker with the A’s. Both are All-Stars, and like Witt, are considered some of the sport’s new generation of stars.
In recent months the model of focusing solely on marketing deals has worked so well that by word of mouth the firm added its first non-baseball clients. That list includes NFL wide receiver Wan’Dale Robinson with the New York Giants and three sports-related social media content creators. “If we keep grinding and keep doing a good job,” Greer says, “we know doors will open and then we can take this business to new heights.”
While Hustle’s model is unique, Greer’s entrepreneurial challenges are, in general, less so: it includes managing rapid growth; meeting and exceeding expectations of an exacting client base in a competitive industry; maintaining high-touch customer service; and navigating a long sales cycle.
Greer is the just-right person to handle all those challenges, believes Hustle co-founder Bruce Kalmick, an Austin-based music industry manager and entrepreneur who has run a record label and managed acts such as Whiskey Myers and the Eli Young Band. Kalmick has had business interests in sports and even has an ownership stake in KK Sportscards, a grading service in Clearwater, he says in an interview.
Kalmick met Greer through their mutual friendship with Witt at a baseball card event. They chatted about sports agent philosophies and decided to go into business together. Kalmick, who runs Why & How Ventures in Austin, says he invested $1 million in Hustle to start the business. “I wanted to give JB a long runway,” he says.
Kalmick says he was impressed with, well, Greer’s hustle. He has since been impressed by Greer’s ability to learn and evolve in running the business. “You can’t really manufacture an entrepreneur,” Kalmick says. “Either people can or they can’t.”
That can-do spirit at Hustle, which recently added its first employee after Greer, will help sustain the company, Kalmick says. That’s especially so in baseball, where he says brands tend to undervalue MLB’s stars in comparison to the NFL or NBA. “The business has a lot of momentum,” Kalmick says. “I’m excited about it.”
Greer, meanwhile, is used to hustling.
He grew up in a small town in Western Kentucky, knowing from a young age he wanted to work in sports. A lifelong Boston Red Sox fan — one of the only times he was truly starstruck, he says, in this field was when he met former Red Sox General Manager and World Series architect Theo Epstein — he went to Xavier University and had an internship with the Cincinnati Bengals in college. His first job in the field was with a sports hiring platform in Cleveland, where he says he learned a lot “working from somebody’s living room for crappy pay. It was a grind of a job.”
Next up was Octagon, where the hustle continued. “They literally gave me a phone and a computer and said ‘go find deals,’” he says. “I learned quickly how to find my voice.”
That’s how Greer found his way to Witt and Rodriqeuz, scouting them in the minor leagues and bringing them to Octagon. Greer, while also working for Octagon, found his way to Tampa during Covid, where he and his wife had some family. Now with Hustle, the company is based out of the Hyde House Public Studio co-work space in Tampa. “I felt like we had a lot of success with baseball players” at Octagon, Greer says, “but I had also reached a ceiling.”
When starting Hustle, Greer and Kalmick set some parameters: They seek players who have been first round draft picks, been in All-Star games, have at least 100,000 social media followers and seven-figure marketing potential. Then Greer plays a bit of matchmaker, finding brands — local, regional and national — to pair up with clients. The process to find a match can be grueling, he says. “You can call 100 brands, narrow it down to 25, get five meetings and then get one deal,” he says.
Greer says he’s learned setting guidelines properly with clients, and not over-promising on what he can get done or deals he can finesse, is a key lesson. “It’s not rocket science,” he says, “but the hardest part of the job is managing expectations.”
Much like an athlete who pushes himself to stay ahead of the competition, Greer also says he’s keenly aware his success can breed others who want to take market share from him. “That’s why,” he says, “the first thing I do when I start the day is I look at our client list, go over it in my head and ask, ‘am I doing everything I can to help this client today?’ This way I know I have that covered.”
