Shaquille O’Neal has said it many times before: He got the blueprint of success from some of the greatest players on the court, and that’s why he wants to pay it forward. As a rookie, Magic Johnson mentored him to think about life beyond basketball. Shaq simultaneously modeled his business strategies after Michael Jordan. Moves like this are how he beat His Airness to one monumental investment in sports.

O’Neal once regretted not seeing Magic’s vision of Starbucks. But he’s now swooping in faster than the Black Cat.

Shaq beats Michael Jordan off the court

After Cincoro, 23XI, and the sale of the Hornets, Michael Jordan’s new foray has drawn attention. He’s reportedly invested an undisclosed amount in the venture capital firm Courtside Ventures. This firm, founded by Deepen Parikh and Vasu Kulkarni in 2016, has set itself apart for its unicorn portfolio, which includes sports, gaming, and media. Courtside Ventures’ portfolio is estimated at $200 million as of this fourth round.

Interesting, though, is that Courtside Ventures drew the billionaire Air Jordan in the fourth round after it already attracted an NBA business stalwart. They also did a third seed round in 2023 at $100 million. It drew some major players in its online gaming fund, like NFL receiver Larry Fitzgerald, hockey pro-Jacob Trouba, and, of course, Shaquille O’Neal.

While Courtside Ventures’ unique sports portfolio is a huge factor in athlete-entrepreneurs investing in it, it’s no surprise that Shaq and MJ had the same idea.

Shaquille O’Neal got the baton from NBA Legends

The big man recently told Baron Davis on The Big Podcast, “The way we set up the business, Magic left it to Mike, Mike left it to me, I left it to Kobe, D-Wade, LeBron.”

When Shaq was a young basketball upstart, spending his NBA paychecks as quickly as he earned them, his mentor, Magic Johnson, schooled him. “It’s okay to be famous, but you better start owning things,” Magic advised Shaq.

At that time, the Orlando salary and RoTY bonus weren’t the only money Shaq earned. Growing up admiring Michael Jordan, it was a sore point that Air Jordans didn’t sell in his size. It didn’t stop him from aspiring to Jumpman greatness. During his business class at LSU, though, Shaq realized he didn’t want to imitate the man himself.

So, in 1992, he ignored Nike and signed with Reebok. He got his logo, the Dunkman, after breaking backboards and releasing Shaq Attaq, Nike’s first signature athlete shoe. So, while he’s making money off Reebok and getting more endorsements, Magic had to keep his mentee straight.

Shaq adapted to Magic Johnson’s path

Magic, the newest billionaire athlete after Jordan, Tiger Woods, and LeBron James, advised Shaq to grow his money instead of getting by on his fame. So before Magic Johnson and Michael Jordan owned the Lakers and Hornets, respectively, O’Neal had invested in the early incarnation of Google in the late ’90s. He claims to have made at least six figures off that.

He infamously passed on Starbucks because he didn’t think coffee would be such a big deal. Magic didn’t, and today, the 6x champions generate more people through his Starbucks franchises, and Shaq moans about missing that opportunity. He, however, got into the franchise game with 24 Hour Fitness, Krispy Kreme, Papa John’s, and even turned Big Chicken Shaq into a fast-casual dining franchise company.

O’Neal withdrew from the Sacramento Kings ownership group but still aspires to be an NBA team owner like the NBA legends before him. Yet he also does things that MJ² doesn’t—endorsements and entertainment deals. Jordan is camera shy, and Magic appears on TV as himself and not as an entertainer. Shaq teamed up with The General in a series of commercials, giving financial advice to young people the way Magic gave him.

As Mike remained with Nike and grew the Jordan Brand, Shaq returned to Reebok to restore it as Swoosh’s biggest competitor. He also followed the Nike method of retro-releasing Air Jordans to bring back the greatest designs in Reebok’s vault.

If it weren’t for Magic’s advice and Jordan’s blueprint, Shaq wouldn’t boast a $500 million net worth today (it jumped by $100 million in 2023 in less than a year). He claims he doesn’t check how much money he has in the bank but hopes to join his inspirations in the Forbes list soon.