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Alex Rodriguez : Baseball Shortstop Turned Entrepreneur

Experience is a great teacher, but she charges a high tuition rate. Just ask Alex Rodriguez. The baseball star turned entrepreneur told his audience at the 2019 Inc. 5000 Conference & Gala in Phoenix that his 2013 suspension from the sport had cost him more than $45 million, but he said, “It was worth every penny.”

While most entrepreneurs haven’t lost — or made — anywhere close to $45 million, small business owners everywhere can identify with going through tough experiences that taught costly, painful lessons but that set them on the right track. Alex Rodriguez just did everything in a bigger way than most people do.

Rodriguez, known as A-Rod, created an impressive athletic record as a 14-time All Star and a World Series champion, but in addition, he’s a true entrepreneur with his hands in many businesses along with taking on a role as a media personality. Through setbacks and shortcomings, A-Rod has marshalled his dedication and impressive work ethic to move from his humble beginnings as the child of Dominican immigrants to great success.

Early Start

Getting an Early Start

It all started in 1975 when Dominican immigrants Victor and Lourdes Rodriguez had a baby boy they named Alex. The Rodriguez family lived in the Washington Heights section of New York City, and young Alex grew up with two siblings from his mom’s first marriage. Baseball formed the family’s passion. Alex’s dad, Victor, who was a die-hard Mets fan, had been a pro catcher back home in the Dominican Republic. “I saw how passionate he was about the game,” Alex later said. “How closely he paid attention to it. That rubbed off on me.

When Alex was four years old, his family moved, first to the Dominican Republic and then to Miami where Alex attended school from 5th grade on. Soon after the move to Miami, Victor and Lourdes separated. Alex remained in Miami with his mom, and in his sophomore year, he transferred from public high school to the private Westminster Christian School.

A gifted athlete, Alex quarterbacked Westminster’s football team and played shortstop on their baseball team. During his 100 games in high school, he batted .419 and stole 90 bases, leading his team to victory at the high school national championship in his junior year. As a senior, he batted .505 with nine home runs, 36 RBIs, and 35/35 stolen bases. Gatorade named him national baseball student-athlete of the year, and in 1993, Alex made history as the first high schooler ever to try out for the United States national baseball team.

Although Alex was slated to attend the University of Miami, his selection by the Seattle Mariners as the No. 1 overall in Major League Baseball’s 1993 amateur draft changed his plans. At 18 years old, Alex signed a three-year, $1.3 million contract to play baseball and received a $1 million signing bonus.


Playing with the Seattle Mariners

From 1994 to 1995, Alex played with the Appleton Foxes of the Class A League in Wisconsin. Soon, his obvious talent got him bumped up to the Jacksonville Suns of the Class AA Southern League, and after playing 17 games with Jacksonville, Alex got promoted to the major leagues as a starting shortstop.

He made history again as just the third 18-year-old to play shortstop in the major leagues since 1900, the first 18-year-old major league player in 10 years, and the youngest position player in Seattle history. After 17 games for the Mariners, in which Alex racked up an impressive .204 batting average, two RBIs, and three stolen bases, the Mariners optioned him to the Calgary Cannons of the Class AAA Pacific Coast League.

In 1995, Alex became the Mariners’ regular shortstop, earning a .358 batting average, the highest for an American League right-handed batter since Joe DiMaggio set the record in 1939. At just over 21 years old, Alex had earned his place as the third youngest batting leader ever. His name was mentioned alongside baseball greats such as Ty Cobb and Cal Ripken, and he was breaking decades-old records for his youth. Alex was also leading the league in runs, bases, and doubles; and he was ranking for base hits and slugging. The next year, fans began calling him by a nickname that has stuck for nearly 25 years — A-Rod.

Both the Sporting News and the Associated Press named A-Rod their Major League Player of the Year, and he nearly won the American League’s Most Valuable Player Award. By 1997, he was an All-Star starter. In 1998, he set the league’s record for homers by a shortstop and won a slew of baseball awards. After an injury in 1999 caused him to miss 30-plus games, A-Rod still managed to land another record, this one as the youngest-ever player to record 100 home runs and 100 stolen bases. In 2000, Baseball America selected him Major League Player of the year.


Time with the Texas Rangers

In 2000, A-Rod, now a free agent, inked a deal with the Texas Rangers, a team that had slipped to the bottom slot on their division. At the time, the contract between A-Rod and the Rangers was the most lucrative ever, promising the baseball player $252 million over 10 years. From the Rangers’ perspective, A-Rod was surely worth the hefty investment.

In his first season, A-Rod scored 52 homers, 133 runs, and 393 bases, becoming the first player since 1932 to accrue 200 hits and 50 homers in a single season, the third shortstop to lead the league in home runs, and the second American League player in 34 seasons to lead the league in homers, runs, and total bases. The next year, A-Rod outdid himself to become the first major league player to lead the league in home runs, RBIs, and total bases in 18 years. He also won the Babe Ruth Home Run Award and his first Golden Glove Award.

Despite A-Rod’s success, his arrangement with the Texas Rangers didn’t prove to be a match made in heaven. He later told reporters that he wished he’d signed with the Mets instead, and by 2003, the Rangers were wishing he had, too. They tried to trade him to the Red Sox for Manny Ramirez, Jon Lester, and a pile of cash, but the deal fell through.

In February 2004, however, the Rangers got their chance when a New York Yankee third baseman named Aaron Boone suffered a knee injury. They sent A-Rod to fill his spot so the Yankees’ legendary shortstop, Derek Jeter, could hold onto his post.


Going to Bat for the New York Yankees

A-Rod tried to bring his special brand of baseball magic to his hometown of New York, but it all seemed to fall a little flat. Despite sustaining his monster numbers and winning another MVP award in 2005, A-Rod found New Yorkers a tough crowd to win over. Not even becoming the youngest player in history to hit 500 career home runs could warm up the chill between A-Rod and the Yankees’ fans.

And then his personal life tanked. A-Rod admitted to using performance-enhancement drugs earlier in his career, and talk swirled around him. How honest were his numbers? Was A-Rod really the baseball prodigy the media had heralded him as? Or was he a phony? Soon, a messy public divorce from his wife Cynthia, coming hard on the heels of allegations of infidelity with Madonna, further eroded the public’s view of their wonder boy.

Leading the Yankees to a World Series championship in 2009 helped revive his flagging public figure some, but the golden image Alex had enjoyed had been tarnished by his fast-and-loose decisions. In his private life, A-Rod was already imploding, and things were about to get worse, much worse.



In 2013, the New Miami Times reported that A-Rod had been receiving illegal performance-enhancing drugs from Dr. Anthony “Tony” Bosch, who ran a clinic in Florida. Called Biogenesis, Bosch’s clinic supplied several athletes with these drugs as it turned out. This allegation was the third such one Alex Rodriguez had faced. Already perceived as arrogant, overly flashy, and too loose with the rules, A-Rod was headed for a fall.

I fell from the top of the mountain, all the way to the ground,” he later told CNN. “I call it ground zero and below.”

While the first two charges had been swept under the rug, the Biogenesis scandal was too big to overlook. It soon became clear that A-Rod had used performance-enhancing drugs multiple times throughout his career and had tried to impede the Office of the Commissioner’s investigations. There was no getting out of it this time.

When punishment fell, it was swift and severe. On August 5, 2013, Bud Selig, the league’s commissioner, announced that Alex Rodriguez would be suspended for 211 games without pay. It was a historic penalty and the one record A-Rod had surely not sought. In response to his suspension, A-Rod filed lawsuit after lawsuit, but by the time settlements could be reached, his suspension was over.

Although Rodriguez’s return to the Yankees dominated sports media in 2015, the once-astounding baseball star never quite got his game back. A handful of records still came his way, but the Yankees clearly no longer wanted Rodriguez. Despite Rodriguez now falling just behind Babe Ruth in the ranks of all-time home run hitters, his former fans didn’t show the same enthusiasm for their hero that they once did. It was time for A-Rod to launch a new career.


Striking Out Into Marketing & Broadcasting

Whether tales of the legendary greats or just basic memories of commerce on Main Street America, business stories always involve a twist. Alex Rodriguez’s move from baseball superstar to entrepreneur was one of those twists.

Although he once owned a Mercedes-Benz dealership in Texas, A-Rod’s first real foray into the world of business came when he took a job as a sports commentator for Fox Sports and ESPN. His experiences as a player gave him deep insight into the games, and he quickly grew to be a popular figure on sports shows. He also recorded an ad for Pepsi in which he played a truck driver in a fleet of delivery trucks simulating players in a baseball game, and another one for Guitar Hero World Tour.

A-Rod’s personal relationship with superstar Jennifer Lopez also helped him make headway in the entertainment world. But Alex Rodriguez didn’t stop with some TV spots and a popular girlfriend; as it turned out, A-Rod also had the heart of an entrepreneur.


Becoming a World-Class Investor

As early as 2000, when he signed his contract with the Texas Rangers, A-Rod had met with Warren Buffet, the Oracle of Omaha, about investing his wealth. Having grown up poor, Rodriguez knew the power of money; and he wanted to mange his finances well. Despite his connection to Buffet, though, A-Rod struggled at first to build his financial team. While his baseball career staff were the best in the business, the folks managing his investments didn’t quite make the starting lineup. So A-Rod pushed himself harder than ever to find the right advisors and supporters for his fast-growing real estate and investment empire. Eventually, one-at-a-time, he found them.

Recently, Rodriguez launched A-Rod Corp, which owns and develops residential real estate, and invests in businesses such as auto dealerships, health clubs, and even an esports startup. Alex is also a primary investor in the U.S. fitness chain TruFusion, one of the fastest-growing companies in the country, as well as appearing as a guest judge on Shark Tank.

What’s A-Rod’s advice for new entrepreneurs? He answered that question recently at an event where he shared a baseball analogy. “You have to give our young players 2,500 at-bats, which is about five years, before we jump in and over-evaluate these young kids. The same is true in business: You need to put in a significant amount of time and effort before you can truly evaluate success or failure. You need to acquire your 10,000 hours. You need to make mistakes. It’s okay to make mistakes.

And he knows he’s right about the mistakes because he’s living proof that a comeback is always possible.

Every tough experience is just another great teacher.



Stephanie is the Marketing Director at Talkroute and has been featured in Forbes, Inc, and Entrepreneur as a leading authority on business and telecommunications.

Stephanie is also the chief editor and contributing author for the Talkroute blog helping more than 100k entrepreneurs to start, run, and grow their businesses.

StephanieAlex Rodriguez : Baseball Shortstop Turned Entrepreneur