Former Yankee great Alex Rodriguez had two dreams as a kid. He wanted to be a professional baseball player and a CEO.
"Ever since I was 10 years old, I sat on my father's lap [and said] I have two dreams: [One was] to be a Major League Baseball player, but that usually never happens, and two was to be a CEO," A-Rod told CNBC's "Squawk Box" on Monday.
Coming up on one year since his final game in August of 2016, Rodriguez is now working on that second goal as chief executive of A-Rod Corporation, a holding company for his various investments, which include real estate, property construction, and fitness.
Rodriguez made about $448 million during a standout career as a third baseman and shortstop. He was a three-time Most Valuable Player with a career batting average of .295 and 696 home runs.
But in his career, Rodriguez was also caught up in a performance-enhancing-drug scandal that resulted in an MLB suspension for the entire 2014 season for violations of the league's drug agreement and labor contract.
"I was always thinking about life after baseball even before my rookie year," said Rodriguez, who signed two of the biggest contracts in baseball with the Texas Rangers and then the New York Yankees. "I played for almost 23 years. I [also] loved business for a long time."
But when he started as an investor, A-Rod said he was not seasoned, and he learned the ropes the hard way. "I didn't have an A-plus team around me."
"What you find is you overpay for stuff. You get the wrong debt structure. You pay a little bit too much. You don't give yourself a safety net," he said.
Looking to baseball for inspiration, Rodriguez recalled how he sought out the best players in the financial world to learn about business. "You get a better team," he said, highlighting the importance in business of using the strengths of others to succeed, just like on a baseball diamond.
For business advice, Rodriguez often goes to Barry Sternlicht, the founder and CEO of Starwood Capital Group, which specializes in real estate with $52 billion in assets under investment.
Sternlicht, who appeared on Monday's "Squawk Box" with Rodriguez, said A-Rod's interest and success in real estate brought them together. "He was a great baseball player. Everybody knows that. But he's a very thoughtful businessman."
Rodriguez said bouncing ideas off Sternlicht gives him a "chance to be around the best." A-Rod has also met with billionaire Warren Buffett, among other leading investment minds.
Now Rodriguez is looking to share his business and investment savvy with professional baseball players in the hopes they can learn to hold on to their money. He's working with CNBC and executive producer Michael Strahan on a new show tentatively titled "Back in the Game."
"Michael and I, something we're really passionate about is taking athletes who have run into some bad luck ... [and] lend a helping hand and hopefully they can get back on their feet," Rodriguez said. Strahan is a former NFL star turned daytime television host.
"If you look at the data," Rodriguez continued, "they suggest that a lot of our players are going bankrupt way too soon. … You make 90 percent of your money between age 20 to 30. Less than 5 percent of our guys in the major leagues have a college degree.
"What happens from age 30 to 80?"