M Club Spotlight: Brian McMahon

Brian McMahon only played football for three seasons at the University of Maryland before giving up the game he loved. It was three years McMahon would never forget, but he was confident he was making the right decision. 

Nearly a decade later, McMahon became the CEO of Pickle, a New York City based company that morphed into a platform that allows users to rent and lend fashion. It’s also a company with a $30 million evaluation, according to Forbes. McMahon believes his time at Maryland set him up for life after college through the life experiences and opportunities he was afforded as a Terp.

McMahon attended Atholton High School in Columbia, MD where he grew up a huge fan of Maryland sports, particularly football. He was also a star dual-threat quarterback for the Raiders’ varsity football team. 

He was coached by a former Terps offensive lineman and current head coach at Archbishop Spalding High School Kyle Schmitt. McMahon was named Baltimore Sun All-Metro and All-Howard County after  throwing for 1,289 yards and 14 touchdowns during his senior season in 2011. He even added 100 carries for 772 yards and eight touchdowns rushing.

But even before his breakout senior campaign, he set a goal for himself to play football at the next level. McMahon was recruited by several schools, two of which were Ivy League. But the hometown kid always knew what college he wanted to attend.

He recalls what made attending Maryland so appealing to him as a young kid.

“The atmosphere and the team was really good a lot of those years which was always exciting to go watch,” McMahon said. “Just being in College Park was always so much fun. We would do a little tailgating, go into the stadium. It was always fun to watch some of the great players like Torrey Smith, Darrius Heyward-Bey, some of those guys, Shawne Merriman. I really loved the atmosphere and kind of the concept of going and playing for the hometown school.” 

McMahon attended Maryland and played football as a preferred walk-on in 2012. He switched to tight end during the preseason of his freshman season where he would be in the same meeting rooms as fellow freshman P.J. Gallo.

Gallo and McMahon both played under former head coach Randy Edsall and offensive coordinator Michael Locksley, who currently serves as the head coach of the program. The two freshmen were always together and quickly became good friends. 

Gallo says he was able to see McMahon’s passion for business and entrepreneurship early on in their time together at Maryland. They explored this passion together through an admiration of billionaire University of Maryland graduate and CEO of Under Armour Kevin Plank. 

“We would always talk about how Kevin Plank was an idol to us,” Gallo said as both were hanging out in each other’s dorms and apartments. “We wrote some business plans, sketched out different business plans and stuff. We did all kinds of tinkering and dreaming in terms of thinking about different ways to live out that entrepreneurship dream.”

Their 2012 season together would prove to be a rough one. The Terps went 4-8 and dealt with a myriad of injuries to the quarterback position. Maryland was also very young at the signal caller position to begin with. 

McMahon was forced to revert to his high school days and learn quarterback again. He served as the backup quarterback for the final four games of the season.

“He changed the concept of Pickle over time,” Gallo said while comparing McMahon’s versatility in the business world and on the football field. “Similar to how he changed his role from tight end to quarterback.”

McMahon played three seasons with Gallo and the Terps from 2012-14 and decided to give up football and focus on his life after college. He was a business information systems major with a minor in business analytics. During this time, he was able to focus on his other dream of starting his own business.

“For me, it was always about how football could set me up for life after college,” McMahon said. “I was always kind of more interested in starting a company at one point so obviously I loved playing football and loved some of the opportunities that it was able to provide me, and I think there's just nothing better to have on your resume than that.”

McMahon began working with Booz Allen Hamilton, a management consulting services company, as an intern and later held a position as a data science strategy consultant. After two and a half years, he moved to New York and began working for Blackstone, a private investment banking company.

At Blackstone McMahon explained his job was to help the firm become more data driven. He was an asset at both companies, but McMahon was still thinking about potential business ideas alongside a friend or colleague. 

McMahon met Julia O’Mara at Blackstone and the two young and ambitious workers had a lot in common. Both were former college athletes who retired early. They overlapped on projects and noticed how well they worked together.

“Brian was always great at Blackstone, and he was awesome to work with,” O’Mara said. “He was somebody that I kind of at that time almost would have considered a mentor within the company. He's a few years older than me and he had started before me and he was working on really, really interesting projects.”

Their business relationship would only grow and when the two weren’t working on projects for Blackstone they were surveying new ideas. The pandemic also allowed them to focus more closely on those side projects.

McMahon pitched the idea of Pickle to O’Mara in the fall of 2020. However, it was much different than the final version. When Pickle broke out in the Spring of 2021 it was an anonymous survey app designed to help people make better purchase decisions. McMahon and O’Mara left a stable job at Blackstone to focus on their company full-time.

The app created communities of users with similar style preferences and when one was in the market for something new, they could post a few options in the form of a poll for people to vote on what they thought they should buy. 

Pickle operated in this way for a year and a half, but McMahon and O’Mara started to notice a lot of users were recommending things that they already owned in the comments of the polls. This stimulated their creative minds, and they came up with the idea to create a platform that allowed people to rent, lend and borrow to and from each other.

This version of Pickle went live in May of 2022. McMahon often compares it to “Airbnb but for things you own.” The two business partners took about 4,000 subway rides delivering clothes and accessories across New York City to kickstart the marketplace without raising capital for the first seven months. 

O’Mara believes her and McMahon’s athletic background made them great business partners for tackling such challenges.

“I think we both have the athlete mentality of we're both very competitive and have a mentality of you got to do whatever it takes to get it done,” O’Mara said. “And you have really, really high expectations and standards of the type of work that we would be producing.”

Pickle now uses third party courier providers such as Uber and DoorDash to deliver the goods. It’s currently only for women's clothing and accessories but McMahon says Pickle will eventually launch men's clothing and accessories. After that, he plans to expand into other asset classes. He sees the possibilities as endless saying, “probably [everything] except for houses and cars.”

Pickle has grown into a multi-million dollar company in less than two years since its expansion. It’s also quickly growing in other parts of the country. In October they received an $8 million investment from Craft Adventures, FirstMark Capital and Burst Capital. 

McMahon and his company even made an appearance on Forbes’ 30 under 30 list for 2024. The annual list highlights 30 notable people under 30 years old in various industries.

Even with all the success McMahon and Pickle have had in New York, he still has a strong sense of Maryland pride. He tries to make it to at least one Terps football game a year and he was most recently at the Maryland vs. Penn State game with Gallo.

“I have never known more about Maryland football or Maryland basketball than I do currently because of how often he is speaking about those teams and how often he is following those games and everything,” O’Mara said. 

McMahon credits his education and playing football at Maryland as experiences that helped him achieve success in his life after college. His appreciation of those experiences is evident in his desire to give back. 

McMahon got involved as a Terrapin Club Donor through Kirby Mills, who worked in various roles with the football program while McMahon was a student-athlete. Mills now holds a position as senior associate athletic director/chief development officer.

McMahon explained why he believes it’s important to give back.

“I think it's so important for just providing the school, the players, the teams with the resources necessary to both compete athletically and academically as well,” said McMahon, who recently became a Lifetime M Club member. “I think obviously with the new wave of college sports and all the NIL going on, it's really important for the schools to be competing in that process and making sure that Maryland stays a strong program, which is obviously great for the school from marketing, PR and just overall ability to attract top talent and top students.”