From humble beginnings to brag-worthy billions, Shark Tank investor Mark Cuban flies in style everywhere he goes. Like other wealthy celebrities, the billionaire entrepreneur has ultra-deep pockets to buy nearly anything he desires. And some of those desirable things are private jets.

How many aircraft does Cuban own, and what are they worth? Here’s everything we know.

How Mark Cuban made the money to afford private jets

After graduating from Indiana University with a business degree, Cuban moved to Dallas, where he came up with the idea of creating a computer consulting company he called MicroSolutions. In 1990, Cuban sold MicroSolutions to CompuServe for some $6 million, Wealthy Gorilla reported.

Cuban invested part of the proceeds of the MicroSolutions sale to found one of the first internet streaming services, Broadcast.com, in 1995. Four years later, Cuban and business partner Todd Wagner traded the company to Yahoo in exchange for several billions of dollars in stock. According to Mark Cuban Companies, the Yahoo barter was one of the biggest internet trades of all time.

Today, Cuban is one of the top 25 wealthiest people alive, with a net worth of almost $4 billion.

Mark Cuban’s impressive private jet collection

Unlike billionaires Elon Musk and Jeff Bezos, who each own one private jet, Mark Cuban owns three luxury jets. He purchased the first, a Gulfstream G550, for $40 million after the Broadcast.com deal with Yahoo.

What makes the deal even more amazing is the fact that Cuban arranged the purchase via email and never saw the aircraft in person before he bought it, Simple Flying reported.

According to Cuban, the Gulfstream jet was one of the smartest investments he ever made. He called the purchase “brutally expensive” while noting to Men’s Journal that in the long run, the pricey jet saved him hours upon hours of time, which is the one asset nobody can own. The $40 million purchase also put Cuban’s name in the Guinness World Records for the largest single e-commerce transaction. The jaw-dropping record stands to this day.

A year after buying the Gulfstream, Cuban spent $36 million on a Boeing 757 so he could transport his basketball team, the Dallas Mavericks, anywhere they needed to go. Outfitted to accommodate players over seven feet tall, the spacious aircraft boasts a medical treatment room, a weight room, and excellent connectivity.

It is unclear how much Cuban paid for the third aircraft in his collection, but Simple Flying described it as a Boeing 767 wide-body that he bought to hire out to high-end charter companies. Never used for that purpose, the enormous aircraft spent several months grounded at Tampa International Airport. Currently, the plane is in storage at Marana Pinal Airpark in Arizona. By the time you read this, it may have been sold for parts.

How he became the successful entrepreneur he is today

Born on July 31, 1958, in Pittsburgh, Mark Cuban was the eldest of three brothers who grew up in the mostly Jewish middle-class suburb of Mount Lebanon, Pennsylvania. His father, Norton, worked as an automobile upholsterer, and his mother, Shirley, was a stay-at-home mom.

At age 12, Cuban wanted a new pair of shoes. Noting that his current footwear was holding up well, Cuban’s dad told him he needed to earn his own cash for such an extravagance. So he invented his first job.

Cuban’s superb sense of salesmanship served him well. Instead of applying for a job flipping burgers, he started selling something he knew every family on his block needed. According to Capitalism.com, the young, shoe-hungry entrepreneur purchased packages of trash bags and resold them door-to-door for twice the price.

Cuban bought the sneakers he wanted. Then he went on to buy airplanes and plenty of other luxuries, too.