Fred VanVleet needs shoes.

The Raptors’ backup point guard still wears Adidas, but that contract expired after last season, so he’s a footwear free agent searching for the right long-term deal.

But VanVleet also wants his own shoes. He doesn’t mean a big-brand signature model like the Adidas sneakers bearing James Harden’s signature he sometimes wears. The third-year Raptor hopes to expand his off-court clothing brand to include on-court footwear, and play in shoes he’ll design, develop and bring to market under his own banner. It’s a massive undertaking, and ideally VanVleet would achieve it while still relying on the network of relatives and close friends he currently employs.

But similar strategies have backfired. Los Angeles Lakers guard Lonzo Ball has distanced himself from his own apparel brand amid slow sales and missing money, allegedly siphoned from the company by the family friend who co-founded it.

Ball and VanVleet are two of a cohort of NBA players grappling with a stubborn reality of off-the-court entrepreneurship. Nurturing non-basketball businesses means balancing the competing interests of family, friends, sponsors and advisers.

While VanVleet plans to grow his clothing brand, he says he’ll still lean on the tight circle of relatives and friends who helped him start it.

“I’d rather pay people that I like, and that I can talk to every day,” VanVleet said. “It takes me a lot to trust people … It’s about empowering the circle around me. Empowering my family and friends.”

NBA players employing their close associates have seen a broad range of outcomes.

At one end of the success spectrum stands LeBron James, who made friend Maverick Carter his business manager and helped Carter grow into a sports and entertainment mogul. James also helped Cleveland native Rich Paul blossom from a hard-working peddler of throwback jerseys to the head of the powerhouse agency Klutch Sports.

And at the other end is Ball, now so disillusioned with the Big Baller Brand that he covered over a BBB tattoo with a crude etching of a pair of dice.

Earlier this week, Ball fired family friend Alan Foster, who Ball alleged couldn’t account for $1.5 million U.S. that had vanished from the player’s bank accounts. According to ESPN, Ball’s financial adviser alerted him to the missing money last fall, and Lonzo held a long-standing distrust of Foster, a family friend who owned 16.3 per cent of BBB.

“Regretfully, I put my complete trust in Alan to manage my son’s business affairs,” Lonzo Ball’s father, LaVar Ball, said in a statement to ESPN. “At the end of the day, family comes first, and I support Zo wholeheartedly.”

There are important distinctions between the apparel lines promoted by Raptors such as VanVleet and Norman Powell, and the megabrand the Ball family attempted to jump-start. Where the BBB launched in 2017 with an expensive, if clunky, signature model basketball shoe for incoming rookie Lonzo, VanVleet and Powell have scaled their marketing efforts to their profiles. A local favourite such as Powell can’t market himself the way a superstar like James would, and he knows it.

“It’s all about the message you’re trying to portray to the people you’re trying to connect with,” said Powell, who founded a clothing line called Understand the Grind. “My message is trying to motivate people to go after their dreams.”

Powell and VanVleet can also target specific markets in ways Lonzo Ball can’t.

While playing in Los Angeles can make a big star even bigger — witness James’ free-agent move to the Lakers — a middle-of-the road NBA player such as Ball could struggle to stand out in a city full of celebrities.

In contrast, Rockford, Ill. native VanVleet and the San Diego-raised Powell can cultivate fans and customers in their hometowns, as well as Toronto.

“The story that connects each player to the fan base is quite different,” said Toronto-based sports marketing agent Sunny Pathak, head of NewPath Sports and Entertainment. “VanVleet (in particular) has the ability to connect with the mindset of the Toronto fan: Put on your boots, lace ’em up and go to work. Fred’s the everyday guy.”

VanVleet says his company recently opened a fulfilment centre in town to accommodate growth in online purchases from Toronto, where he has developed from a Raptors 905 call-up to a valued complement to all-star Kyle Lowry. He also ran a pop-up shop in Wichita, Kan., where he played college ball and still operates a summer basketball camp. And he operates a bricks-and-mortar retail space in Rockford, where he hopes to become a beacon for Black-owned, family-run businesses.

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“It means a lot to my community to be one of the first Black-owned businesses to have a store downtown,” he said. “To have e-commerce. To have guys get out of that environment. These are guys that I love, and instead of just feeding them money I’m going to give them a job and see where it takes them.”

Beyond that, he’s still seeking a good pair of shoes.

And he’s willing to make them himself.