In a move that would seem unthinkable in the 1990s, billionaire Mark Cuban purchased a Gulfstream G5 jet worth $40 million entirely online. Fresh off the sale of his pioneering streaming company, Broadcast.com, to Yahoo! for $5.7 billion in stock, Cuban cemented his place in e-commerce history. He made what is considered the “largest single e-commerce transaction” at that time. In a recent conversation on the Club Shay Shay podcast, Cuban shared with Shannon Sharpe that after the sale, he simply “bought a jet…online” to save time and gain mobility for his burgeoning business ventures.
According to Cuban, as a frequent traveller, a private jet was a practical investment, saving him what he deemed his most valuable asset—time. “Time is the one thing you can’t own more of,” he told Sharpe. Having a jet, he explained, made it easier for him to take quick flights without enduring the hassle of commercial travel. Describing his purchase process, Cuban explained that he’d contacted Gulfstream via email, specifying his requirements and requesting a test flight. “I was always the internet guy,” he said. After the test flight sealed his interest, Cuban requested the price and paperwork, then wired the full amount online. “I did the whole thing online,” he said, reflecting on how unconventional the transaction was for the time.
Rewarding Employees After the Yahoo! Takeover
The Broadcast.com sale was transformative not only for Cuban but also for his employees. After the Yahoo! acquisition, Cuban ensured his team was handsomely compensated, with 300 out of the 330 employees becoming millionaires according to The Independent. Reflecting on the decision, he described the company’s success as a group effort, saying, “I’m not there without them. They were there for me the whole time.”
Cuban also made headlines with his foresight in managing the wealth he amassed from the Yahoo! deal. Ahead of the 2000 dot-com bubble burst, Cuban hedged his investment by selling calls on Yahoo! stock and using the proceeds to buy protective puts. When the market crashed, the value of his puts skyrocketed, turning a potentially devastating loss into a gain. “Those puts became worth even more money than I would’ve gotten from the stock,” he explained, adding that the strategic move was once named one of “the top 10 trades in Wall Street history.” This principle of sharing the wealth and managing risk had guided Cuban even in his early days, as he followed a similar profit-sharing approach when he sold his first company, MicroSolutions, in 1990.
The Impulsive Lifetime American Airlines Pass Purchase
Cuban’s penchant for spontaneity also led him to an unusual investment: a lifetime American Airlines Airpass. After selling MicroSolutions, Cuban was just shy of 30 and ready to celebrate his newfound millionaire status. In the 1990s, he recalled, he wasn’t interested in flashy cars or luxury homes but wanted freedom to travel wherever he pleased. One evening, celebrating with friends, Cuban wondered aloud if he could buy a lifetime air-travel pass. Spurred on by the idea and a few drinks, he picked up the phone, dialled American Airlines, and asked if such a thing existed.
As it turned out, the Airpass department offered exactly what he was looking for. According to The Independent, Cuban initially paid $125,000 for his lifetime pass, later upgrading it to cover first-class travel for himself and a companion indefinitely. For years, Cuban relished the ability to call American Airlines and book spontaneous first-class trips. “I’d be out in LA or Dallas, and I’d say, ‘Let’s go to Vegas tonight,'” he recalled, adding that he once even extended the perk to friends and family.
Though American Airlines stopped offering new lifetime passes in late 2022 and fully discontinued the programme in early 2023, Cuban’s pass remains valid. He’s since passed it on to his father, who enjoyed the privilege until his passing, and later to a friend.
A Shift to Conservative Investing
In recent years, Cuban has shifted his investment approach, leaning toward low-risk strategies to navigate the prolonged post-pandemic market volatility. Describing himself as a conservative investor now, he prefers secure income streams like US Treasury bonds, which have provided stability amid fluctuating economic conditions. “With interest rates at 5%, it’s easier to do that,” Cuban noted.
Yet, despite this conservative turn, Cuban remains committed to his passion for supporting entrepreneurs through his role on Shark Tank. While he finds security in Treasury bonds, he still invests in startups, especially those with innovative solutions and strong growth potential. Cuban’s goal, he explained, is to “help entrepreneurs achieve their dreams” while exercising greater caution with his wealth elsewhere.
