On the basketball court, Dwyane Wade is a bona fide expert. Off the court, the three-time NBA champion has learned to question everything.
On Monday's episode of the "Armchair Expert" podcast, Wade told hosts Dax Shepard and Monica Padman that he became interested in business early in his basketball career. The move was prompted by a 2007 shoulder injury, which made him concerned about his athletic longevity, Wade told Fortune in 2020.
The problem, Wade said on the podcast: He didn't know much about anything beyond basketball, or even where to start learning about business. So, he found friends and friends-of-friends with industry knowledge — and peppered them with questions.
"I'm always the guy who is willing to raise my hand and say, 'I don't know that. Can you explain that to me?'" Wade said. "I don't know everything, but I am willing to learn."
Over the course of his 16-year NBA career, Wade made roughly $196 million in salary — and $14 million in endorsements in his final NBA season alone, according to Forbes. Today, he co-owns a restaurant, is a minority owner of the NBA's Utah Jazz and has business partnerships with Budweiser, BallerTV and Chinese sportwear company Li-Ning.
He wouldn't have any of those ventures or partnerships, he said, without advice from people whom he trusts.
For business insight, Wade said, he listened to Magic Johnson — the basketball Hall of Famer who is now a start-up investor and part-owner of multiple sports franchises, including baseball's Los Angeles Dodgers.
Wade told Fortune that he flew to Los Angeles multiple times to meet with Johnson, who told the then-young player that he already had "the blueprint" to succeed because he knew how to "grind" and "do more than what everyone else was doing."
"[Magic] told me... 'You have to approach [business] the way you approach the game of basketball,'" Wade said.
For advice on becoming a television personality after he retired in 2019, Wade said on the podcast, he turned to Michael Strahan. Strahan, who retired from the NFL in 2007, made his own transition from star athlete to television personality somewhat seamlessly — appearing or co-hosting regularly on football broadcasts, ABC talkshows and even gameshows over the past decade.
And for nearly everything else, he said he relied on Shaquille O'Neal — dating back to when they were teammates on the Miami Heat.
"When [Shaq] came to Miami, he totally changed my entire life," Wade said, detailing how O'Neal helped him build confidence by making Wade believe he was going to be the next "superstar."
"The work that he put in on me and with me — he never gets enough credit," Wade said.
Crucially, Wade also learned a tough lesson early on: Asking questions only helps when you trust the people you're asking. In 2009, Wade sued a former business partner for libel after their attempt to launch a restaurant failed. The following year, Wade settled another lawsuit for not meeting marketing obligations for a separate never-launched restaurant chain.
"I walked away with experience," Wade told Fortune. "From that point on, I started having everything looked at by the people that I trust, and not just trying to do it on my own, [or] because someone is cool or someone is nice."