Billionaires tend to be famous for their measured moves in boardrooms and markets. Recently, though, some of them have been playing risks outside their well-documented turf—pitting their wits against new territories that have nothing to do with money.
Bill Ackman, one of the greatest hedge fund operators, surprised enthusiasts and critics alike when he ventured into the professional tennis arena. While his performance was mocked, the greater story is about how incredibly successful individuals are taking personal risks that undermine their sense of self outside the borders of wealth.
So why are billionaires courting failure in public? And what can we learn from them?
Walking into the Arena—Literally
Bill Ackman’s foray into tennis was not pretty. Videos showed the billionaire getting thrashed by experienced competitors in quick succession. The internet had labeled it “cringe,” but to others, it was courageous. For a man who was used to measured business moves, diving into a completely new, results-oriented realm was a radical shift.
But it was never about winning. The pleasure was in being doing something new, open, and unknown out there in public. For someone whose choices have shifted trillions on the market, voluntarily taking a leap into new terrain is a different type of confidence.
Risk Isn’t Always Financial
Part of the reason that Ackman’s action rings true is that it reflects a reality too rarely experienced in public life: the courage to fail. Most billionaires are risk-takers by trade, but they make their bets with precision. On Wall Street, they call the shots. In sports, there is nowhere to hide.
Bill Ackman is not alone. Elon Musk attempts to colonize Mars. Jeff Bezos explores space. They are larger-than-life initiatives, by all means, but with emotional, physical, and reputational costs. The kind that cannot be insulated from money.
The general public likes to feel that billionaires just throw in the towel on effort once they “make it.” But experiences like Ackman’s demonstrate that growth personally does not end with money—it transitions.
Beyond Ego: Why It Matters
Skeptics will accuse these stunts of ego or media whoring. That is partly true. There is more to it, a more profound level. To step outside your comfort zone—even if you are rich—takes humility. And it says something: growth never ceases.
Ackman might have practiced tennis in private. But by practicing it publicly, he made room to discuss it. It says to people that it’s alright to learn something new—even poorly—at any age or salary level.
The legislation wasn’t one of control. It was one of humanizing. We would rather place billionaires in the unreachable universe. We are reminded that they are also people when they fall on a tennis court.
The Personal Becomes Professional
There is a business aspect too. These unorthodox activities influence what the public perceives about leadership. Ackman’s response to the question of how emotionally intelligent, socially sensitive, and human CEOs can be shows that he is prepared to own up to his mistakes, which is a difficult quality to find in high-stakes finance.
Authenticity matters more than ever before. Employees, investors, and customers want more than spreadsheet managers. Witnessing someone as powerful as Ackman struggle and keep coming back again might redefine success and resilience in high-performing cultures.
From Boardrooms to Ball Courts: A Growing Trend
Bill Ackman is only one of a growing tide of billionaires seeking meaning and identity outside their portfolios. Some opt for social causes, such as MacKenzie Scott’s quiet philanthropy. Others push their bodies to the limit, such as Richard Branson with his stunt flying.
These activities are typically hobbies that have been back-burnered across the decades of accumulating wealth. Now they’re surfacing. And more notably, they’re being revealed.
It’s not inspiration. It’s a legacy. Impact is not just about cash—it’s about how cash is used, shared, and even bypassed.
Last Thoughts: Risk, Relevance, and Reinvention
Bill Ackman’s clumsy tennis venture might have made headlines for the wrong reasons, but it stands for something right. It reminds us that any measure of success cannot insulate anyone against the humility of learning, the pain of failure, or the need to reinvent.
In a culture that’s consumed with becoming better, it’s liberating to watch someone openly fail. Because failure is how we learn, in front of others. And learning is the one thing that every human—rich or poor—is entitled to equally.
And now, whether you’re a weekend enthusiast or a hedge fund titan, the message is obvious: the actual winners are those who continuously show up, not where they’re most capable, but where they’re weakest.
