How Lee Martin (HBS ‘26) painted his unorthodox path to HBS
At his core, Lee Martin is an artist. It was his first love as a boy raised in one of Chicago’s project housing neighborhoods. With nothing more than a sketchbook and a pencil, his life changed the day he braved the Orange Line train alone to visit the city’s esteemed Art Institute. Though he’d never been exposed to painting prior to that, he was immediately captivated by this new medium. He quickly gained such an appreciation for classic paintings from Western movements like impressionism, fauvism, and the Harlem Renaissance that he decided to teach himself their techniques with no professional help whatsoever. A natural perfectionist who “hates to cut corners,” he applied his drawing skills to build sketch blueprints that turned into paintings so good that he began to receive attention, both locally and nationally.
At the same time, he was also an up-and-coming talent on the basketball court. Hoops was more than a game in his southwest Chicago neighborhood of LeClaire Courts, just a few blocks north of Midway Airport. It wasn’t uncommon for Chicago legends like Kevin Garnett, Shawn Marion, and Quentin Richardson to stop by during the offseason to play pick-up. Court time was at a premium, but Lee’s siblings were well-established in the local community, providing him opportunities to play at a young age. Though he faced obvious disadvantages while competing against stronger, more skillful older players, he excelled as a pass-first point guard despite a more subtle on-court demeanor than many of his counterparts. It was natural for him to eschew the brash, in-your-face bravado synonymous with the game in favor of a deliberate, collaborative style that involved other players and required cohesion in order to achieve success. The commitment to process that he showed as an artist also translated to success on the basketball court. A persistent focus on repetition and development of the fundamentals turned into an invitation to play AAU as a middle schooler, which allowed him to elevate his game to yet another level. He aspired to follow in the footsteps of famous Chicagoans like Derrick Rose and Dwyane Wade as he entered adolescence and approached high school.
However, he learned that it wasn’t always easy to pursue lofty goals in two very different arenas. With his twin passions seemingly in conflict, he found himself at a personal crossroads. His middle school lacked the accelerated art programs he knew he’d need to continue to develop his skills, but the thought of leaving the world he knew seemed like a daunting ask for a 14-year-old born and raised in the Windy City. However, word had started to spread about his work on the canvas, and the acclaim he’d received led to a fellowship at The Putney School. Attracted by the progressive curriculum, commitment to the arts, and autonomy that the academic experience offered, he made the difficult decision to trade the concrete of Chicago for the trees and hills of southern Vermont.
There, his horizons expanded. Required as part of his coursework to explore other styles of art, he tried his hand in ceramics, sculpting, printmaking, and weaving, among many others. He equates his experience to that of a cross-genre musician and instrumentalist. Pharrell was the example he used, who leverages his training in other disciplines to improve his work in his medium of choice. Putney’s Work Program expanded his horizons in other areas, including a firsthand experience of what it’s like to work in a horse barn, but he quickly realized that his passion for the hardwood remained. And while sports weren’t emphasized in rural southern Vermont like they had been back in Chicago, Putney had a basketball team that just so happened to need a point guard.
Over the next four years, Lee and his teammates, who he notes came from all over the nation and world, elevated the team’s fortunes, achieving formidability at a school not known for athletic success. Still, few college scouts made the trip to Vermont to see what the “art kids” had to offer as basketball players. As such, he’d come to terms with the reality that his competitive basketball career was likely done and began to assess his post-secondary options accordingly. NYU’s robust art program provided obvious appeal, but a full ride at Swarthmore College ultimately won the day. Known for their liberal arts education, it seemed like a logical transition from his experience at Putney. Decision made, he headed south after graduation with an eye on a career in the arts.
However, the game once again pulled him back. Shooting hoops alone in Tarble Pavilion, the on-campus arena, during his first days on campus, he was noticed by a few members of Swarthmore’s varsity squad, who encouraged him to try out. He made the team as a walk-on and earned respect as a steady contributor throughout his time on campus. His methodical play style was a natural fit in Coach Landry Kosmalski’s “Secondary” system, and he worked his way up the depth chart, ultimately appearing in 15 games during his senior season. That season just so happened to be the best in Swarthmore’s history, as the “core infrastructure” that he and his teammates had built over the years culminated in a trip to the Division III National Championship game, where the Garnet fell to Wisconsin-Oshkosh.
Though he never reached the on-court heights of many of his boyhood heroes, his competitive basketball career developed into far more than he’d expected as a high school student. And though he’d come to Swarthmore with the initial goal of pursuing a career in the arts, he used his time there to learn more about the worlds of economics and sociology. It didn’t hurt that, since he’d been away for a while, these career paths could likely facilitate a return home to the Windy City. Originally thinking that consulting would be a great fit for his team-oriented, collaborative working style, he instead decided to take a chance on something different — passing up full-time job opportunities to accept an internship in the municipal bond space at C.W. Henderson, which led to a full-time opportunity at Loop Capital, a minority-owned investment bank based in downtown Chicago. There, he quickly proved himself and established a network of mentors, including Loop’s founder and CEO Jim Reynolds, a titan of Chicago’s business community, further validating what his experiences had already taught him: that he didn’t have to follow conventional pathways in order to achieve success. He flourished in this role and began to build a life in his hometown beyond anything he’d imagined as a boy.
And yet, despite all he’d achieved in his years at Loop, the same urge that drove Lee to Putney, Swarthmore, and the once-unintelligible world of high finance began to pull him in another direction. His professional success had placed him in management roles that he initially felt unprepared for, and he began to look externally for opportunities to develop as a leader. Business school seemed like an obvious fit, and he applied all over the country but was immediately taken by the opportunities and challenges that HBS provides. The quiet demeanor he displayed on the court had persisted into adulthood, and he realized that developing his skills as an articulate public speaker through the case method would pay dividends in his professional life. Secondarily, his experience in the corporate world had reinforced the value of the HBS network, so his decision to attend upon receiving admission was not a difficult one.
Here at HBS, as everywhere else, he has flourished, finding community in Section I and realizing that his unorthodox background has more applications to the world of business than he could have ever imagined.
With all he’s accomplished so far, it seems impossible to predict what comes next for Lee. Chicago is and always will be home for him and his girlfriend, Candace. Despite a busy academic and personal schedule here in Boston, he finds time to continue supporting Loop’s work with the Chicago Bears’ ongoing stadium project. With that being said, he remains characteristically mission-oriented and plans to make his life wherever he can achieve the most impact in his chosen field of infrastructure investing. The foundational elements of his character — creativity, persistence, and an unwillingness to compromise — are the only non-negotiables.
As he puts it, wherever the world takes him, in times of uncertainty, he’ll draw on the inspiration provided to him by a mentor after his entire art collection was lost in an apartment fire: “Now you can paint the world in a new medium.”
John Mahoney (MBA ’26) is a native of West Des Moines, Iowa. He graduated from the University of Notre Dame in 2021 with a degree in Finance. While in college, he was a walk-on defensive back for the Fighting Irish and wrote a book about his experience, titled “History Through The Headsets.” Prior to coming to HBS, John worked in consulting and strategy in Minneapolis and Chicago.
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