The first sketch Dwyane Wade, the perennial NBA all-star, made of a sock was a bit shocking.

A large wave swept across the calf with a small man surfing inside, a checkerboard wrapped around the ankle, and foot and toe were covered in cheetah print.

“No,” Clarke Miyasaki, a vice president at Stance Socks, says he told Wade. “This is awful.”

“Trust me,” Wade replied.

Wade wanted to launch his own line of socks. Athletic, casual, dress socks — you name it. He had wanted to for some time but couldn’t find a company to partner with. So his agent reached out to Miyasaki, a vice president at Stance Socks, a funky sock manufacturer and online sock marketplace. After a while Miyasaki and Wade were exchanging text messages about potential designs.

Wade insisted his three-part sock monstrosity make the first collection.

At $14 a pair, it became Wade’s top seller.

The Stance partnership marked the beginning of a larger transformation for Wade, 33, who is drifting further into the business world as his basketball career begins to wind down. Since 2011, he has focused on establishing an off-the court niche catering to high-end consumers looking for products that fit into a luxury lifestyle brand.

His line of Napa Valley red wines with Pahlmeyer sells for $250 a bottle. There are Dwyane Wade neckties and pocket squares with Tie Bar. He’s made two watches with Swiss brand Hublot, the most recent, released in 2014, costs $19,400 a pop.

“This game of basketball doesn’t last forever,” Wade said in an interview. “If you don’t plan for your future, I don’t think that’s a smart thing to do.”

Wade’s efforts are part of a broader trend among professional athletes to develop business interests beyond the playing arena, branding experts say.

Shaquille O’Neal in retirement has a series of app-based games and a jewelry collection at Zales. Cleveland Cavaliers superstar LeBron James announced a partnership in July with Warner Bros. to start an entertainment production company.

“The revenue model changed for a lot of athletes,” said Felicia Miller, a marketing professor at Marquette University, the school Wade led to the NCAA tournament’s Final Four in 2003. “They realized during their career and long after this, they could make a lot of money.”

Wade already makes a lot of money. He’s set to rake in $20 million next year playing for the Miami Heat.

But his business ventures could make him even wealthier. “He’s building equity well beyond the basketball game so when he hangs up his sneaks he’ll have a large company to be CEO of,” said Allen Adamson, chairman of brand consulting firm Landor.

One of his riskiest bets so far has been related to a staple of any professional athlete’s brand— his shoe. An American shoe deal would have netted Wade around $2 million annually, according to industry estimates.

Instead Wade decided to partner with Chinese shoe maker Li-Ning to create his own shoe. The shoe, which sells under the brand name Way of Wade, sells for $150 and $200.

But it is currently primarily sold in China, which has been suffering from a slowing economy lately.

“I made a decision three years ago, going on four, to leave the Nike umbrella and the Jordan brand to go off to China and try a company, Li-Ning, that was not known in the states,” Wade said. “I wanted to take control of my brand and my business.”

Wade, who has 5.5 million fans on Weibo, China’s version of Twitter, says China is a natural market for him — his wine is only sold there too.

“I have a great following in Asia. I understand the Asian market. I know that Napa Valley wine is now starting to pique the interest of the Asian market, and it’s somewhere that we wanted to start right now while I’m playing,” he said.

Building an audience in China now, while he is still near the prime of his career, leaves a better chance his brands will endure past his retirement as the marks of a cultural and fashion icon rather than a hoops star, marketing experts say.

“On the whole Western brands [such as Wade] are held in high regard and considered to be of high quality,” said Sarah Boumphrey, Euromonitor’s head of strategic and consumer insight. “However local brands are increasingly competitive here.”

Or, at least, that’s what Wade is betting on. If it doesn’t work out, he said, he’ll have a lot of glasses of red wine to share with his family, something he’s not exactly upset about.

“It’s a passion,” he said about building his business empire. “I’m a very competitive person, so once I say I want to do something, or once something appeals to me, now I want to be the best in that.”

When the Heat missed the playoffs this year, Wade enrolled in a Harvard Business School class to up his business acumen.

“As I started to become an older man,” Wade said, “I started to understand I have other interests. I have other passions than just basketball.”

And though fashion might be a primary interest, he said, building a successful brand is what drives him. After he posed for an Esquire Magazine photo shoot earlier this month — pictured in a black suit, no undershirt and a dark blue cape draped over his shoulder — he took to Twitter and Instagram to argue that fashion is a form of wearable art.

“People look at me just as a basketball player,” he said. “So they see me doing something else, doing a spread for Esquire Magazine, and they don’t understand it, because they’re like, ‘You’re just a basketball player. You should be focused on basketball. You shouldn’t be posing in a fashion magazine,’ because they don’t understand that you have other things that you love.”

And as his playing days wind down, his time to focus more intensely on his brand is fast approaching, he said.

Luckily for Miyasaki from Stance, Wade’s style has become refined. Look for a pair of D-Wade socks on the Stance Web site today, and those wave-checkered-cheetah atrocities are nowhere to be found.

“That’s what my brand is,” Wade said. “It’s evolving.”