Wealthsimple is an investing service that uses technology to put your money to work like the world’s smartest investors. In “Money Diaries,” we feature interesting people telling their financial life stories in their own words.

My advice to younger players would be to just save your money. Live off your interest, if you can. Of course there will be people who come into your life looking to get some of that money. You have to prioritize. Meet with your financial advisors quarterly. Finalize a list of family and friends you want to take care of. But when that list is finalized, that's when it stops. It's not too hard for me to say no. Because you know you have a good heart and you want to take care of other people, but there are times and places for things.

When I was young, I grew up with my grandparents on farmland in Florida. We had peach trees, orange trees, a flower orchard, grape vines. My grandfather made wine, my grandmother was a seamstress. And they had a couple of jobs on the side. So I was a familiar with a stable lifestyle as far as money was concerned.

But my immediate family? They didn't have much money.

I moved to New York with my mom and her family in third grade. My first income was shoveling snow. I was 11 years old, I’d wake my little brother up in the morning and we’d knock on the neighbor's front door, and ask if they needed their driveway or walkway shoveled. We might do three or four homes, depending on the size of the snowstorm. They would give us a couple of bucks, or they would invite us in for hot chocolate and marshmallows, and then we'd just go to the next house. I was with my mother for the school year, but I was with my father during the summertime and he had a lawn service company that he and his brothers owned. He would wake me up in the morning to go work with him. I wasn't getting paid for it, but in some ways that was my first job.

I'd spend most of the money I earned when I was kid, but I'd save a little. I was able to get a Mongoose bike — my mom helped me out, but I chipped in. I put pegs on the front and the back. I put the dice in the spokes. My bike was everything.

I was the ninth pick in the 2002 NBA Draft when I was 18 years old, straight out of high school. Sports was my thing growing up. I played baseball, football, and basketball. But basketball was my number one sport. From the very beginning, I was better than anyone my age. Even in elementary school, I was the best kid in the neighborhood. I knew I could probably get to the NBA if I just kept getting better. And it happened. I would say money was a significant factor in the decision to go pro instead of going to college. I wanted to make sure I was able to take care of my family. Going to college would have been fun, a great experience, but there are no guarantees in college. You can get hurt in college and then your NBA career is over. You don't have any money. I knew that I was ready for the NBA. My body was ready. My game was ready. But it wasn’t until I first stepped onto the court in an NBA game that I really realized what had happened. I was like, "Man, my life has changed forever."

In the NBA, when you have yearly team dinners, there are so many different ways you can split the bill. You can put names in the hat. Or if the veteran guys are there, they’ll take out the rookies. But if you happen to go to the same restaurant as the coaches, they know they’ve got to cover the bill — if they'd see us, they'd try to hide.

My rookie contract with the Phoenix Suns was a two-year deal, for like $3.5 million — something like that. When I got the first paycheck and I saw all those zeros — it was for like $300,000 — I thought, "Man, this is like the Richie Rich movie." You wake up and now you're rich. I was overwhelmed. I splurged on a new car. I bought a truck. I actually got a very nice little apartment. I got my mom a home. I bought some jewelry. I bought some clothing. I took my brother shopping. When you see tears in your mother's eyes and the joy in your brother's face? Those moments only come once in a lifetime.

Later on, I got a financial advisor, but initially, that first year, I was managing my own money. I went and opened up a bank account at Bank of America. Other than those purchases, I was mostly conservative with the money. I think what helped me a lot was the rookie transition camp that the NBA puts on, where they go over finances. I really tuned in. My teammates helped, too. Stephon Marbury, Tom Gugliotta, Shawn Marion, and especially Penny Hardaway. He had a major Nike campaign: the “Little Penny” commercials. When I got to Phoenix, he had his own office, his own company. I started taking notes and learning from him how he was taking care of his business.

In the NBA, when you have yearly team dinners, there are so many different ways you can split the bill. You can put names in the hat. Or if the veteran guys are there, they’ll take out the rookies. But if you happen to go to the same restaurant as the coaches, they know they’ve got to cover the bill — if they'd see us, they'd try to hide. It happens every year. I think my second or third year in the NBA, I got stuck with a bill. We were out drinking, and I'm thinking everything's cool, not knowing how much these glasses of wine cost. Next thing I know, the bill comes out and it was $3000-3500, and I'm like, "Hold on, wait a second. I'm paying for this bill?" I was 21 or 22. I'm like, "Man, I haven't signed my major contract yet fellas."

I was 22, 23 when I signed my major contract for around $89 million. That was the exact same week I signed with Nike. At that time, I was the highest paid forward-slash-center to sign with Nike. So it was a big summer for me. And obviously, playing in the NBA you want to make money. But honestly that wasn't my main motivation. I wanted to be a great basketball player. I knew if I were to continue to play at a high level, then the money would come.

A lot of the businesses I have now are passion projects. For instance, I always had love for fashion. I wanted to stay fly. So when I got to New York, I was able to create a platform — we built this line called Spiritual Gangster, and it's taken off. I also got into wine pretty early in the NBA. After about five years or so, I spent a lot of time going on trips to go wine tasting, learning. I actually just launched my own line of wines, the Stoudemire Private Collection.

Art came on later in life for me. It was more of a learning curve, so I surrounded myself with artists and friends who were in the art space. The first step was when I got a painting from a friend of mine for my birthday. It was a painting of me with the lyrics from Tupac’s “Bury Me a G” in the background. That's when it all began. I may overspend on art, man, it may be my weakness. My most expensive piece is probably my Jean-Michel Basquiat. It hangs in my home in Miami. It's a painting of Basquiat in Hollywood — it’s got an L.A. type of vibe.

My biggest thing just goes back to: save your money. If you save properly, you can live off your interest. Now, that's not feasible for some people. For me, it keeps me on the right track. It keeps you out of your pockets — you spend the money from the interest before you're spending your actual money. I never knew exactly what my life was gonna be at this stage, after the NBA — I hoped it would be a fun and successful lifestyle. But being able to plan gave me a lot more options.

As told to Dre Miller exclusively for Wealthsimple; transcript edited and condensed for clarity. Illustration by Jenny Mörtsell.