It’s rare that you can truly say you work at your dream job. Long Island native and former Division-I baseball player, Kyle Gelling, has the distinction of being able to say that as he has established himself working at Barstool Sports since 2018.
While luck certainly plays a part in finding the perfect job, Kyle put himself into that position through relentlessly pursuing his passion of working in sports and has reaped the rewards of that work.
But to understand how he got there, you need to know where he started.
The Early Days
Kyle was born and raised in West Islip, the second of two children, his sister being 10 years older. He always had a love for sports – specifically baseball and football.
His father split season tickets with a group of friends and he was able to attend roughly 15 games per season for the New York Mets. Growing up in the late 1990s, he developed an affinity for the Mets and he cited his favorite players as Mike Piazza, Robin Ventura, Al Leiter and one quirky player, reliever Turk Wendell, who was known for his various superstitions such as wearing a necklace of shark teeth, jumping over the foul line, slamming the rosin bag, brushing his teeth in between innings and his obsession with the number 9.
His fondest memory was attending playoff games during the 2000 season in which the Mets played against the crosstown rival New York Yankees in the Subway Series. Kyle attended Game 3 of the World Series, which happened to be the only game the Mets won in that series.
As far as his own playing career, Kyle was fortunate to grow up in a sports-crazed town like West Islip, which eventually turned into a powerhouse in both of his favorite sports.
During his youth, travel baseball was not what it is today. He said, “it was Little League or nothing back then,” and his team was talented enough to win their district. They also went to Cooperstown during the “Week of Champions” although they struggled against the elite competition.
One of the strengths of a town like West Islip is that the top players generally play together all year and also play multiple sports which creates teams that are exceptionally athletic, well-coached and have strong chemistry.
West Islip
2008 was the year that West Islip put it all together. They had arguably the two best players on Long Island in RHP Nick Tropeano and catcher Patrick Cantwell. They also had electric outfielder Steve Smith as well as Gelling.
“We had the best team on Long Island,” said Gelling. After defeating Commack in the County Championship, they moved on to the Long Island Championship against Massapequa. The game was played in Valley Stream and Gelling noted that the field was very small and a couple home runs went out that their outfielders were camped under. Regardless, it was a great season for West Islip and they sent 5 players to play Division-I baseball and that isn’t counting those who opted to play football.
Gelling is one of the players that had a chance to play collegiate football as well.
He noted that he was looking at all of the Ivy League schools as well as some Division-IAA schools. He was awarded the top defensive back on Long Island and was named All-Long Island.
Despite arguably being a better football player, he noted that his heart was in baseball and the Ivy League schools did not offer athletic scholarships and were only offering him a chance to walk-on for the baseball teams.
Following his junior year, he played for the Long Island Titans. That was an incredibly grueling summer as he stated he was basically on the road for 2 months playing at different tournaments and showcases.
For the first several weeks, no offers came in. He had been to Georgia twice and he said “I was so fried, I was ready to give it up,”
During a showcase in Virginia, things changed. Gelling was there for two days.
“The first day went about as bad as it could go – I went 0-for-6 with 6 strikeouts,” he said laughingly. Fortunately, the next day, his team was being coached by the Georgia Washington coach and he had a say to remember as he had an awesome day at the plate and it was the completely opposite. The George Washington coach expressed interest and Gelling ultimately decided to commit there, signing his NLI in November.
It was back to work for his senior season. Gelling had another good year for the Lions going All-League as they were co-League Champs with Centereach. During a crucial series in late April, Gelling ripped a walk-off two-run triple to left center after a two-out error prolonged the game and brought him to bat. Gelling noted that the team used a picture of that to give him on Senior Day. Ultimately, they had their season end and he headed off to college.
George Washington
Gelling was an outstanding multi-spot athlete but chose to focus on playing baseball in college to maximize his chance of playing professional baseball. Unfortunately, injuries are a part of the game and they can happen in freaky ways. His injury occurred during batting practice when he stepped in a hole in the outfield and missed virtually the entire season (played 7 games).
He was able to bounce back during his sophomore season and play respectably as he appeared in 41 games and batted .252 with 11 RBIs and 5 steals in 6 tries. He ended the season on a strong note, finishing on a 5-game hitting streak.
Gelling went onto play in the Hamptons Collegiate Baseball League. He performed exceptionally well, crushing 8 HRs for the Collegians.
The following season, Gelling took a step forward for GW as he appeared in 44 games and batted .264 including .275 in Atlantic-10 games. He led the team with three pinch hits.
He was hoping to finish his career strong and with an outside shot to get drafted if he had a big senior season.
Unfortunately, the injury bug bit again and this one was more severe.
Gelling noted that he had been experiencing pain in his shoulder in the fall. He was diagnosed with a torn labrum, and his doctor told him that he could play through it if he could handle the pain as he wouldn’t do any more damage.
During the Christmas break, he woke up in serious stabbing pain and had it checked out again. Upon getting an MRI, it was revealed that the rotator cuff had frayed off the bone and it would require surgery. The surgery took 4 hours to complete. It marked the end of his baseball career.
He went back to the school, opting to focus on completing his degree in marketing. He noted that he was also worked in the sports marketing department for the school, working for the non-ticketed sports and events during the spring semester.
The Next Chapter
Upon graduating, Kyle moved back home and landed a great job working as an Inside Sales Representative for his beloved New York Mets. What made this even better timing was that it was 2015 – when the Mets rode a magical second half and postseason run into the Fall Classic against the Kansas City Royals. Gelling was able to attend all of the home playoff games with his dad. He even was given a National League Championship ring as a member of the organization.
He wanted to pursue a new path, though, in the social media department. While he was able to get an interview, he was not hired for the position. He ultimately left his role and went back to college to get his masters at Hofstra University.
This was 2016 and he was able to land an internship with Newsday and he covered the Presidential debate at Hofstra, which he noted was a great experience.
Gelling was able to land a role working with MLB.com as a social media specialist. The irony is that he was in charge of covering the Mets, despite not landing the position while he worked with the Mets organization.
The workload is heavy, as he was often watching three games as once. It included working nights, weekends and holidays as well. Gelling worked in this role for 3 seasons before he got his real dream job – at Barstool Sports as a producer for the Starting 9 podcast with Jared Carrabis and Dallas Braden.
This was in 2018, after the company exploded in popularity with the acquisition by the Chernin Group but before the Penn deal took Barstool ‘to the moon’. During his time at Barstool, he has been a few different roles, as he is now a co-host on the ‘We Gotta Believe’ podcast with Clem and KFC. Additionally, he runs several of the social media accounts, he’s a social program editor and deals with the sponsorship posts.
He has thoroughly enjoyed his time at Barstool.
“They’ll have to drag me out of here – I’ll never leave. It’s such a good work culture despite what you may read in some articles. They are so supportive but let you do your own thing. I get to set my schedule and they encourage you to try different things.”
Gelling has truly been the blueprint for how to rise through the ranks in new media and forge your own path and it is quite impressive.
