Billionaire founder Bill Gates is known today for his philanthropic efforts with The Bill & Melinda Gates Foundation, but when he started making money off Microsoft, his first purchase was a bit more frivolous: a Porsche.
Gates isn't alone in spending his first major paycheck on something fun. From cars to video games to household upgrades, here's what six successful business leaders, athletes and actors bought when they started earning real money.
"I bought one thing that was a tiny bit of a splurge," Gates told David Rubenstein during a 2016 Bloomberg interview. "It was used, but it was an incredible car."
The car didn't gather dust in Gates's garage, either: He loved to put its speed to the test with aimless drives around the New Mexico dessert. After one particularly raucous night, he even had to call business partner Paul Allen to bail him out of jail, according to a Time profile from 1997.
"Sometimes when I would want to think at night, I would just go out and drive around at high speed," Gates told Rubenstein. "Fortunately, I didn't kill myself doing that."
Tennis superstar Serena Williams is one of the highest-paid athletes in the world and has raked in more than $84 million over the course of her career, according to Forbes. But she's been careful about how she spends her money.
In fact, after earning her first million, Williams didn't touch any of it — she deposited it directly into the bank and walked away.
"I remember, I went through the drive-through to deposit my check and they were like, 'I think you need to come in for this,'" she recalls in an interview with Uninterrupted, a media company owned by LeBron James and Maverick Carter.
Williams says that, for her, tennis has never been about getting paid. She's always played for the love of the game. In fact, she used to forget to collect her paychecks at all.
"When I first turned pro, you had to go pick up your check," she says. "I never, never picked it up, so at the end of the year, the tournament directors would literally hand me the check because I would never go get it."
Today, billionaire Mark Cuban splurges on conveniences like his own private plane. But back when he was young, money was tight, and his splurges were far less extravagant. At 24, he was living with five friends in Dallas in a three-bedroom apartment. The rent was $600, which they split six ways.
The place wasn't very nice, and neither Cuban nor his roommates had the funds to upgrade it. Case in point: "I had these old ratty towels that had holes in them and could stand on their own in the corner, they were so nasty, I needed a shower from drying off after a shower," Cuban writes on his blog.
But once Cuban landed a job selling software at a store called Your Business Software, he started making good money — and he only had eyes for one luxury.
"I went out and bought six of the fluffiest, plushest towels I could find," he says. "I was moving on up in the world. I had the towels. Life was good."
In 1992, a 20-year-old Shaquille O'Neal signed his first professional contract, officially becoming a millionaire. But within an hour, the budding basketball star had already gone on an expensive shopping spree and was down over $1 million.
O'Neal's first purchase: a $150,000 Mercedes Benz for himself. He immediately followed that up with a matching one for his father and a smaller $100,000 one for his mother. O'Neal also paid off his mother's house and began doing "what all the homeboys do — gotta buy rings and diamonds and earrings and this and that," he told Business Insider.
A few days later, O'Neal's bank manager explained that he was already $60,000 underwater. That served as the wake-up call O'Neal needed to become more careful and get his spending on track.
However, he doesn't regret helping out his parents. "I [spent] a million dollars in about 45 minutes," he told CNN. At least in part, though, "it was well worth it."
Before Jordan Peele starred on Comedy Central's "Key & Peele" and directed the critically acclaimed "Get Out," he lived paycheck to paycheck. Then, in 2004, Peele auditioned for MadTV alongside longtime friend Keegan-Michael Key. Although they were competing for the same role, their palpable chemistry earned them both spots on the sketch comedy show.
That role became Peele's big break — he garnered an Emmy nomination for his "Sad Fitty Cent" music video — and first it scored him a steady paycheck. "When I was on MadTV, I was still living month to month. My obnoxious buy would've been an Xbox," he told Bloomberg when asked what he did when he first got paid.
As Peele's career continued to take off, he realized earning bigger and bigger paychecks wasn't about buying as much as he could. "You realize the value is in not having a side job," he told Bloomberg. "Even today I don't splurge — I'm the anti-Scarface. All these things you imagined you'd buy — none of those would bring me much joy or peace."
The dream purchases he abandoned? "Props from movies or memorabilia — a nerd collection. At some point, I could let go of the fantasy of owning one of the Gremlins."
It's been over a decade since tennis superstar Maria Sharapova clinched her first Grand Slam championship. At age 17, she defeated Serena Williams in the 2004 Wimbledon final. It was her first of what would be five Grand Slam titles, and it came with a sizable paycheck: £560,500, or about $724,000.
That's a lot of money for any teenager, particularly for one who grew up poor: At age seven, the Russian-born athlete and her dad arrived in the U.S. with just $700. While training at Nick Bollettieri's Tennis Academy, she slept on a pullout couch next to her dad in a $250-a-month apartment.
And, when 17-year-old Sharapova secured her six-figure check, she headed straight to TJ Maxx. Her splurge? "One of those bright-colored Louis Vuitton bags that I wore for one day," she told Time Money.
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Video by Luqman Adeniyi