Athletes and entertainers face unique wealth management opportunities, considerations and challenges. The athletes and entertainers we interviewed shared their personal stories and perspectives to highlight the need for more financial education in the sports and entertainment world. We thank them for being strong advocates of financial literacy.
Robert’s advice
Robert’s advice
“Work with financial advisors who are focused on financial education and helping you and your family gain insights on how to plan for your long-term goals. You should be able to explain how an investment builds or preserves wealth—before you invest your money.”
Family values
Robert was nine years old when his family moved from Barbados to Miami in search of a better life. Although his mother and father worked long hours, they made time for talks around the family dinner table. “My parents stressed the principles of hard work and accomplishment. We were chasing success.” For Robert, the importance of academics was so firmly established that the eventual two-time Super Bowl champion never even considered the NFL until his final year with the University of Miami Hurricanes. “I only thought about going to medical school.”
A wake-up call
With the Hurricanes, Robert earned two national championship rings. The Los Angeles Rams selected him in the 1991 NFL Draft. He soon discovered that managing his NFL earnings was a challenge. “I had no budget in place. By the end of my first year, I had to borrow $10,000 against my second year. I needed the money to make it through the months before training camp.” It was a wake-up call. “I started saving every penny.”
By the end of my first year, I had to borrow $10,000 against my second year. I needed the money to make it through the months before training camp.
In the history books
In 1994, in a game between the Rams and the New Orleans Saints, Robert made history. He scored a touchdown by returning a punt for 103 yards, the longest punt return in NFL history. He was signed by the Dallas Cowboys in 1995. The team won Super Bowl XXX the following year. While enjoying a higher income and more success on the field, Robert also became more interested in investing. “I started asking, ‘Who is making money in this country?’ I learned about stocks and bonds and how to evaluate companies.”
He vowed never to repeat the financial mistakes he made in his first year with the NFL. “I refused to buy jewelry, expensive cars or anything that doesn’t bring value. I look at everything as an investment. If I spend $5,000 on going out each month, that’s $60,000 in a year. I could invest that money instead and receive a healthy return. I started seeing everything in a different perspective.”
While I was playing football, I was always looking for what was next. Nothing lasts forever.
A new calling
Stints with the Miami Dolphins and the Detroit Lions followed. In 2000, Robert was signed by the Baltimore Ravens, leading to his second Super Bowl ring. He rejoined the Lions in 2001. A broken neck suffered in a game against the Green Bay Packers ended his football career.
Robert was mentally prepared for this inevitability. “While I was playing football, I was always looking for what was next. I didn’t put all my eggs in one basket. Nothing lasts forever.”
Super agent
Robert’s understanding of player relationships and interest in people made him a natural fit to be a sports agent. “I was friends with everyone on the team. It didn’t matter to me if you’re offense or defense, big or tall, or Black or white. I really enjoyed talking to my teammates and getting to know them.” He was interested in everything from their upbringing and early football experiences to their current off-season hobbies. “Being an agent is about the ability to communicate well with complete strangers. You’re trying to get them to take a meeting. I realized I had that skill set.”
Less than a week after retiring from professional football, Robert joined his agent Drew Rosenhaus’s firm, Rosenhaus Sports Representation. He rose to become president of the firm, which now manages over $1 billion in active NFL contracts. Robert’s personal interactions with top professional athletes shape his views on why he believes financial education for players is needed early on.
When you get your first NFL contract, you’re 21 years old. You have no idea what to do with the money, other than what comes naturally to a 21-year-old. You don’t think about investing it.
21-year-old mindsets
Like their contemporaries, young professional athletes tend to be inexperienced with money—but their generous starting salaries give them a lot more to lose. “When you get your first NFL contract, you’re 21 years old. You have no idea what to do with the money, other than what comes naturally to a 21-year-old. You don’t think about investing it. You think about spending it on something fun, like clothes or cars. Whether the amount is $1,000 or $1 million, the mindset doesn’t change.”
Robert speaks from his own personal experience. Although he was able to course-correct quickly, he’s concerned for athletes who might not be as nimble. NFL players have a small window of earning opportunity. A second or third contract cannot be taken for granted, and even the brightest of careers can be ended suddenly by injury.
“A football player’s journey is school and then professional football. It’s not like a corporation where you start out in the mail room. Players enter the NFL at the top. There’s no opportunity to learn as you make your way up from the bottom.” The combination of youthful exuberance and millions of dollars doesn’t always end well.
The right financial advisors
Filled with industry jargon and unfamiliar concepts, the investment world can be confusing to the uninitiated. “It’s like speaking French to the players.” Lacking the financial knowledge necessary to make informed decisions, athletes may select financial advisors based on personality and may be enticed into investments that they don’t fully understand.
“The role of the financial advisor should be more focused on education and helping players and their families gain insights on how to plan for their long-term goals. It should be more than simply telling players what they’re going to do with the money and saying, ‘It will be great.’” Advisors should encourage questions and outline the risks and rewards of investment recommendations. Athletes should be able to explain how an investment builds or preserves wealth—before they invest their money.
Smart players will hear the alarm bells go off in their heads. They’ll understand why it’s important to learn about managing their wealth.
Robert acknowledges that making the right financial decisions takes maturity and a willingness to be financially engaged. “Smart players will hear the alarm bells go off in their heads. They’ll understand why it’s important to learn about managing their wealth.”
Giving back
Becoming financially savvy at the start of his career has afforded Robert the financial freedom to be a devoted father and give time and resources to important causes. He has volunteered as an inner-city youth basketball coach with the Stay in School program and served as a celebrity spokesman for the You Can Achieve Your Dreams if You Work Hard Enough campaign. He also hosted the annual Robert Bailey Celebrity Golf Tournament, which supported Community Health Clinics of South Florida for families with insufficient insurance coverage.
He wants other athletes to have the same freedom to contribute to their families and communities long after their playing days are over.
Start here
Start here
Together, we can build your legacy.
Start here
Start here
Together, we can help establish the legacy you want to leave.
