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Former AC Reynolds star thrives at Barstool Sports with his flair for the comedic

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    ASHEVILLE, North Carolina (WLOS) — No playbook could have possibly prepared Caleb Pressley for his job with digital company Barstool Sports, even the one he had a decade ago at AC Reynolds High School. What he didn’t fully realize back then, is how his big personality would pay off.

“My own path of how things have worked out for me so far have taught me just follow your gut,” says Pressley, sharing the approach to life that’s served him well.

He creates unpredictable, clickable content for Barstool, which has nearly 10 million Instagram followers. His interviews with athletes like Cowboys legend Michael Irvin are full of ‘LOL’ moments.

“When you were playing in a big game, did you ever have an opportunity to take a minute, look around, and say ‘Wow, I should not be this high right now,'” he asked Irvin, who erupted in laughter.

“I think Barstool has really made me feel empowered to do whatever I want to do,” Pressley told News 13.

He’s got a flair for the comedic and the hilariously dramatic. It’s not just what he asks, but how he asks a question that makes him fun to watch.

“Deion Sanders, ever heard of him?” he once asked NFL Hall of Famer Deion Sanders. “No I would prefer Prime, it’s two different entities,” Sanders explained.

“Do you have ‘the it factor?'” Pressley followed up. “I am it!” Sanders said.

Some spend years envisioning their dream job. But the reality is, he couldn’t have dreamed of all this as a student at AC Reynolds, where he played quarterback on the 2009 state championship team.

“I wouldn’t have believed you, dude,” said Pressley. “Because most of my jobs on social media, most of it wasn’t even around. When I was at Reynolds, we didn’t even have Instagram. So if you would have told me that I was gonna make money off Instagram I would have told you that you were an idiot.”

Coach Shane Laws was a big fan of both Pressley’s play and sense of humor.

“No I’m not surprised by any of it,” Laws said of the QB’s career. “Caleb always had a good personality and was always very creative.”

“I knew he would be in some type of media. I guess initially I thought it would be ESPN or something like that, but I think that’s a little bit too subdued for Caleb,” says Coach Laws.

Guess you could say he has the X-factor.

“Do you have the X-factor?” Pressley asked Sanders during their conversation. “I have two exes,” Sanders replied.

Pressley went on to play for UNC-Chapel Hill. It’s not his play on the field that caught Barstool founder David Portnoy’s attention, but a curious title given to him by the team.

“I don’t know how many people are watching North Carolina football games, but he is the Director of Morale,” Portnoy said, introducing Pressley on Barstool’s “The Rundown.”

That’s the moment the ex-QB threw a Hail Mary and asked for a job.

“I’ll have a communications major, I don’t know what that really gets you in the real world. Maybe one of you guys will throw me a job!” he said.

“You may have a job, believe it or not when you graduate!” Portnoy told him

“Yeah, the way that played out proves it never hurts to ask — never hurts to ask,” Pressley says.

Six years later, he’s still willing to ask almost anything as he sits down with sports figures and celebrities like rapper Waka Flocka Flame.

“Are you a romantic?” Pressley asked him. “Am I a romantic?” Waka Flocka Flame answered. “For the last two years of my life I’ve been romantic, yes I’ve been suaved out.”

Pressley recently moved from New York City to Florida, where he’s chasing another unexpected dream. He’s working towards becoming a professional golfer, a goal he realizes could take a decade to achieve.

He’ll continue to work for Barstool Sports as he shoots for the moon. To this point, let’s just say his fearless approach has been like rocket fuel for the former Reynolds star’s career.

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