In a recent revelation, Whitney Tilson, a former hedge fund executive and recent candidate for mayor of New York City, discussed the origins of Bill Ackman’s now-famous icebreaker, “May I meet you?” The line, which has garnered significant attention on social media, was reportedly one of Ackman’s go-to phrases for meeting women during their college days at Harvard.
Tilson, who has known Ackman since their time at Harvard, recounted that Ackman often shared anecdotes of using his bold pickup line, particularly on the subway. “That’s Bill. He’s just very forward. If you know his history as an investor, he is the most stubborn, persistent person I know. And he will stick his neck out,” Tilson explained. This trait has certainly served Ackman well in his finance career, where risks and bold moves can lead to significant rewards.
While Tilson noted that he never witnessed Ackman use the icebreaker in person, he conveyed admiration for his friend’s confidence, suggesting that Ackman’s physical presence as a tall and attractive man likely played a role in the line’s effectiveness. Ackman, who is now a billionaire with a net worth estimated at $9.3 billion according to Forbes, is recognized not just for his investment strategies, but also for his persistent nature.
In a recent social media interaction, Ackman acknowledged the challenges many young men face today in meeting women in public settings, attributing this difficulty to the prevalence of online dating culture. His post encouraged individuals to embrace spontaneity and expressed nostalgia for a time when meeting new people felt more organic.
Tilson remarked that although Ackman didn’t intend for his tweet to gain widespread attention, it struck a chord with many. He described the line as “benign,” suggesting that it reflects a simpler approach to social interactions.
Having spent nearly two decades running Kase Capital Management before closing the firm in 2017, Tilson is known for his advocacy of value investing and has authored a book on the subject. His observations about Ackman’s dating strategies added a personal touch to their longstanding friendship, highlighting how behavioral traits in both finance and personal life can intertwine.
Throughout the years, Ackman had several college relationships and took pride in acting as a matchmaker among his peers. While Tilson himself never tested the pickup line, he shared that he doesn’t view it as a poor approach, indicating an openness to its potential effectiveness. As discussions about dating and social interaction continue to evolve, Ackman’s straightforward approach resonates with those seeking connection in an ever-changing landscape.
