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.

Andre Iguodala is the swingman (and 2015 Finals MVP) for the Golden State Warriors. Rudy Cline-Thomas has been his business partner for more than a decade. Together, they have invested early in scores of businesses, including companies like Casper and the Players' Tribune. And with their annual Players Technology Summit, they're also bringing athletes to the world of finance and Silicon Valley.

Andre: I grew up on a tight budget: buying in bulk, shopping non name brands, trying to make a dollar stretch. I worked at a car wash. I worked at a Godfather's Pizza. I worked at a library — I had to consolidate like 20 years of magazines by using this machine to glue them together. I used the money from those jobs for whatever fifteen- or sixteen-year-olds would use it for: gas money, trying to go to the movies. More than anything, I was trying to buy some shoes and clothes.

Rudy: We didn’t have much, so I couldn’t wait to work. My first job, in 7th or 8th grade, was a junior counselor at a summer camp. I made $10 or $11 an hour. My parents let me spend half my check, and made me save the other half. Then they gave me that money when I went to college.

Andre: I had no idea I might make it to the NBA. It was really late for me — the year before I got drafted — when I realised, oh, this basketball thing is a thing I could make a career out of. I'm from a small town in Illinois. I wasn’t a McDonald’s All-American. I went to Arizona to play college ball, but there were guys that were better than me. I think going into my freshman year, was the first time somebody mentioned NBA to me. A coach said, "You'll probably go to school for three years." I was like, "Then do what?" He was like, "You might go pro."

I thought he was joking. I didn't take it that seriously.

Rudy: I actually always wanted to play basketball — I think we all wanted to play basketball. But my school had a stock-picking challenge in 7th grade, and that’s when I got turned onto the market. But it was still probably second to basketball. My dad went to business school and my mom worked for Royal Bank, so I’ve always been surrounded by business. I started out in finance as soon as I got to college, and then I picked up accounting. My first job out of school was working for Lon Babby, a sports agent at the time.

Andre: I only stayed two years at Arizona. Once you know you might go in the top ten in the NBA Draft, why risk it? Once they told me I was good enough, I was like, "Yeah, I'm out.” Obviously, money played a part in it. But I just enjoyed playing basketball, so it was more the allure of going to the NBA.

I wasn't thinking about all the money, the cars, jewellery. I'd never seen that before, so I wasn't looking for it. My first contract was for four years, $9 million. I think the fourth year was a team option, so if you don't improve over the first three years, then they can cut you — so, really, three years, $7 million. You get an advance over the summer, and just before the draft, you get an advance for trading cards and an advance for a shoe contract. I remember a loan agency floating me until I got the advances. They sent me a check for $25,000. I think I just went to Niketown and bought a whole bunch of pairs of Jordans. I spent like two or three grand and it felt like I spent a million dollars. I didn't know how to spend money. And it was so early that there wasn't enough money to go buy a car, you know? I was happy where I was at.

Steph was having a conversation about net neutrality one day, and I wasn’t as caught up on it. He got started on it, and I was locked in, because he did his homework!

I read a few books, like the Dummy's Guide to Investing, a Standard & Poor's book about investing. But I also learned quickly to position myself around the right teammates. I had a few veterans who were really smart with their money. I mean, they had nice contracts, but in the scheme of the NBA, they were on the lower end.

I asked a lot of questions, and they got me into good habits early. I think it's always important for young athletes to position themselves with the veterans who are professionally and financially savvy.

One of my favorite conversations was with Elton Brand, who had two or three max contracts. He talked about black wealth. He talked about Oprah's situation, Will Smith — African Americans who created a lot of wealth. There aren't too many of us. There are only 23 billionaires that are African American. It wasn’t like he was trying to teach me a lesson: Make sure you do this, make sure you do that. It was more like: You know how hard it is to have wealth. Period. And then how hard it is to be African American with wealth?

He also helped me understand how much money you should have saved up for retirement — what's real money, what's not real money. You can save up a couple million, but that's really nothing in the grand scheme. He used to always say, "How much paper can you stack up by the time you're done? Then parlay that into doing bigger things.” He had a certain number in mind. I think it was $10 million. He was like, "You get 10 million in the bank and you get interest off that every month. And then you don't have to have any other income. That is your income."

That was the first or second year of my big contract with the Philadelphia 76ers — six years, $80.5 million — so that’s when my checks started looking a whole lot different. They added some digits to my yearly salary.

Around the same time — about ten years ago — Rudy and I started talking. We started to get to know each other, and build a relationship. He came to me with this great idea: he wanted to open an E-Trade account, he would pick some stocks, I would pick some stocks, we’d go over why we’d picked them. He took all the risk on the fee structure, which was crazy. Basically, I couldn’t lose. If I lost, he would have to pay me the money. You never get approached from somebody with a fee structure like that! We invested in a lot of tech companies. And we made a lot money that year.

Rudy: I remember when he played for the Denver Nuggets in 2012-13, they got upset in the playoffs by the Golden State Warriors. I remember the Nuggets were playing in Oakland, and after the game, Andre was like, “Wow this could be a cool place to come and play.” That was the first time I heard him even mention the possibility of playing for the Warriors. Then I remember when he called and he said, “You won’t believe what just happened.” The Warriors had cleared enough cap space to sign him in 2013. And we were both beyond excited.

Andre: We kind of struck gold with the timing. A number of my Warriors teammates — Steph Curry, Draymond Green, Javale McGee — are into investing and tech. But we never look at it as a competition. We inform each other of what’s going on. We have a lot of conversations. I learn something from all of those guys. Steph was having a conversation about net neutrality one day, and I wasn’t as caught up on it. He got started on it, and I was locked in, because he did his homework! That's our locker room talk. We have free agents come to our team, and the first day the guy is walking in like, "What do you know about this business?"

Rudy: Andre and I meet every two weeks. We visit new companies. We're literally partners — he sent me a business plan this morning, a company that he likes. He'll send articles every day, interesting information, tidbits on the marketplace.

90% of the time when I'm in meetings or conferences, I'm the only African American in the room. You always think, "Why?" If only other people have the opportunity to see what I was seeing, have access to what I had access to. We realised that most athletes are not going to have the access to what we were learning, you know? So what medium could we create to spread this knowledge, this love, this wealth?

Andre: Rudy and I have done a tech summit for the players — the Players Technology Summit — for two years now, and we get a lot of interest. Players will email me, text me, or talk to me about it during games.

The best part of the ride is going out there and getting access to people who can help us, and then bringing it back to our athletes and giving them the same knowledge and hoping they do the same thing.

Rudy: I'd say we’re invested in at least 25 startups right now. We don't do clichéd investments. We're not going to do an investment because it's sports, or where Andre's going to be a pitchman. I think initially everyone thought, "Oh, we're invested in something that should be a little basketball-ish.” But those are investments that usually don't scale. We invest in financial businesses, tech businesses, enterprise businesses. Initially people don't think that you understand that or that you care about that stuff. We've had to break that mold.

Now we have a massive network of venture capitalists that help us vet deals or pass along something they're investing in and want us to invest with them.

Andre: We didn't really worry about the perception of, “Oh, he’s just an athlete.” Our thing was: if they don't let us in, we'll find a way in. They’re disruptors, we’re disruptors. For us it was just a drive to get the right knowledge and the people who want to be with us.

Rudy: He has more than enough money than he'll ever be able to spend from playing basketball. I just want to help him have as many options as possible — I don't think any other player will have as many options as Andre will have once he's done playing basketball.

LeBron James, Alex Rodriguez, Magic Johnson — those guys are all stars. Those guys are possibly the best players in the game at their positions and obviously have more opportunities than the average player. Andre’s gone to an All-Star game, and he’s been a great player, but he's not esteemed as one of the very best. Yet he's created more opportunities for himself than just about anybody. The reason why he'll have more influence is because he’s more accessible: people can see their lives and careers as parallel to his versus LeBron. People can identify with Andre more than the stars.

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