Christmas came early this year for Fred VanVleet — way back on Nov. 15th — the first pay day of the NBA season.

In the off-season, VanVleet struck it big – at least by the standards of an undrafted free agent always judged to be too short and not enough this and not enough that. After an outstanding second season with the Toronto Raptors earned him a podium finish for the NBA’s Sixth Man award, VanVleet cashed in as a free agent when a contingent from the team’s front office met him in Chicago on the morning of July 1st and the two parties agreed to a two-year contract worth $18-million.

Some things need to be seen to be believed.

“It’s never real until you see it hit your account, you know what I mean?” VanVleet said of the anticipation he felt waiting for the first of his 24 installments (it works out to about $750,000 every two weeks during the regular season) to hit his bank account. “I was checking my phone every other five minutes. The first one for sure.”

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VanVleet didn’t grow up poor – both his parents worked as he came up in Rockford, Illinois, a mid-size city west of Chicago where not being poor made you an exception. But the moments he felt ‘rich’ were when income tax refunds arrived or when the relatives were able to stuff some cash in his jeans at a birthday or Christmas and the hole would start burning in his pocket.

“Money? We didn’t have it. We had a big family with four boys so that’s a lot of mouths and clothes and basketball tournaments to pay for,” he says. “Our parents busted their butts to make us feel like we weren’t broke and in our neighbourhood we were probably more well off than everyone we knew, but we lived cheque-to-cheque. There was no money to save or invest. It was only when I made the NBA that I saw the difference.”

VanVleet has already made a difference in his family, using some of his good fortune to spread the wealth in his immediate circle.

“My nephew and my baby sister both go to private school now, which is a huge accomplishment for our family,” he says. “And I bought my mom and step-dad a house and I was able to get [Mom] a car this summer. Those things and small things that don’t get a lot of notice – I’m not trying to go Instagram famous – I don’t post a lot of my stuff.”

And he’s had some fun too – “I’m not as serious as everyone thinks.” After the deal was official, there was a boys’ weekend in Las Vegas.

“My Dad and my brother were all able to go and my best friends flew down and we had a great time at Summer League,” he says. “That was the big thing for us and we’ll do a vacation this [coming] summer when there’s more time to plan it.”

But with his first Christmas as a multi-millionaire coming into view, VanVleet, 24, has been planning something a little different and a little bit more meaningful for his family as well as his long-time girlfriend Shontai Neal and those in their close-knit inner circle. Like almost everything he does, it’s with the long view in mind.

“I’ve been working the last two years to get everybody in my circle out of debt and it’s not cheap,” says VanVleet. “That’s more important to me [than material gifts]: to give them the financial freedom and a clean slate and help them get educated. Life happens: People are trying to make it happen with kids and they take loans and credit cards and you have to pay for school and doctor’s bills and divorces happen, so for me it’s trying to get everybody a clean slate and help them get debt free.”

It’s not a simple undertaking and it’s required VanVleet getting educated himself. The savvy point guard arrived in the NBA with a veteran’s feel for the game and a professional approach to his craft from Day 1, but figuring out how to manage money for the first time – even when he was earning the NBA rookie minimum of $543,471 – has been an on-going process.

Soon after turning professional, VanVleet began working with Derek Folk, president of Los Angeles-based Williams Tax and Financial Group. While it’s common for a lot of athletes to work with an investment advisor, that VanVleet chose to work with an accountant and tax specialist first suggests a subtle but critical shift in priorities.

“If you say you need an investment advisor, you’re skipping a step,” says Folk, who counts a number of entertainers and athletes as clients – individuals for whom wealth can come suddenly and whose earning years can be brief. “… We start with: do you understand credit? Do you understand budgeting? Do you understand the basic principles of money? With Fred, that’s what we started, and that doesn’t happen over the phone and that doesn’t happen in one meeting. It takes several meetings and a lot of discussions, because we’re trying to educate him.”

VanVleet was an eager student. At Folk’s suggestion, he began keeping a journal to track his financial goals and progress in the same way he’d kept one for his basketball goals for years. VanVleet dreams big in both areas but understands that steps must be taken. His off-court NBA role models are the likes of LeBron James, who has reinvested in his home town of Akron to help lift an entire community and has become one of league’s most successful businessmen in addition to an all-time great on wood.

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The scale may be different, but VanVleet has an eye on having an economic and charitable impact in Rockford. By starting his own line of apparel – ‘Bet on Yourself’ – VanVleet has not only signalled his ambitions but also created a vehicle where he can learn the ins-and-outs of entrepreneurship while the stakes are relatively low and he can stub his toe and learn.

“The numbers are pretty small in the grand scheme of things but the business lessons – no matter what the revenue – are translatable,” he says. “I’ve bumped my head a bunch and taken losses and learned about tax breaks and all those things that come along the way … the more you learn about it and the more you’re informed and know what to expect and how you can help yourself of hurt yourself, the better off you are.”

His accountant’s pride is almost palpable, even over the phone from Los Angeles:

“What makes Fred’s case unique is he’s the responsible adult in the room. Who Fred is makes my job easier,” says Folk. “He’s patient. I deal with some athletes and artists and they’re – I don’t want to say spontaneous – but they’re ready to go. Fred is more mature. He’s not anxious, he’s going to think about things. He’s not going to make a rushed decision.”

Still, getting rich quick and young can create challenges – particularly if you come from a family and a community where wealth is a foreign concept. There have been some awkward moments.

“Once you get a substantial amount of money, I don’t feel like it changes you,” VanVleet says. “It gives you a sense of comfort that you don’t need to be anyone besides yourself — or you can be who you want to be — [but] you do see people change around you because of expectations and false stereotypes.

“People don’t really understand money – especially in our community, where I’m from. They don’t understand the government gets half up front and we don’t get it all in one lump sum or that this contract is paid out over 24 months and there’s fees and escrow and bills, you know what I mean? People just see the $18-million and to them – people who aren’t familiar with it all – [they] equate it to winning the lotto.

“I try to educate my people, tell them exactly what I’m going through and how the money works and it helps a little bit, [but] I say ‘no’ all the time.

“In my first year when I didn’t have a lot of money, I gave everyone a mulligan early, for the most part,” he says. “They had their one ask and that point it was low, they weren’t expecting a lot, so I would give everyone a bone early and after that, if it’s something that’s outrageous or something I don’t want to do I say no and see how it goes.

“But for the most part – I’d say 95 per cent of my family and friends – the experience has been really, really good and that’s why I’ve been able to get here today, I’ve been blessed with a good support system.”

With that in mind – and with Christmas coming – VanVleet felt the need to do something significant to recognize those who helped him get to where he is now. With Folk’s help, he devised a plan to not simply share his wealth, but to help give those close to him a platform where they can work towards their own financial independence. Published estimates suggest that, in U.S. households that hold any kind of debt, the average is nearly $35,000 in car and credit card debt alone. A few more unexpected events and a missed payment or two and credit scores crumble and the cost of borrowing increases, creating a cycle that’s difficult to break and VanVleet’s family is no different.

The plan this year is to help clean up those balance sheets: pay off the most pressing loans, shore up individual credit scores and provide the resources to help those near to him. Between him and Shontai, VanVleet figures they are aiming to help about 10 families in their circle – be in a position where they can invest in a home or make a down payment on a car or take an education loan independent of him. Rather than have to co-sign on a loan or use his cash to buy something outright, if he can help pay outstanding debts and improve someone’s credit and set them up with a down payment, they can move forward on their own.

“One of the things we try to say is: ‘let’s teach your family how to fish,’” says Folk. “What does that mean? The average person, athlete, whatever you are, you get wealthy and your family is not and all of a sudden you find yourself supporting them and the more you have the more you support them. That’s not healthy … you want to help, but you’re better off saying ‘I’m going to give you a pole and worm and a book that tells you what to do with the pole and the worm’ instead of just giving them a fish you caught.”

Rest assured VanVleet is going to make sure when the family gathers at the home he helped buy in Rockford the bottom of the tree will be well-stocked with all the toys and gadgets and clothes and the rest that help make the season memorable and fun.

But for his first holiday season where money is no object, VanVleet is most excited about helping his family enjoy things that money can’t buy but which a lack of it can make difficult to achieve: relief from the gnawing anxiety not having enough so commonly brings and the hope that your circumstances can change.

“That’s the biggest thing I’ve gotten out of this whole thing – how financial freedom can relieve the emotional stress people are under,” VanVleet says. “I know money can’t buy happiness, but financial freedom is a start to an easier way and that’s something I’m trying to give … that’s the biggest thing for me.”

For VanVleet and his family, some Christmas gifts are meant to last.