It might mean calling a crush and professing your undying love, or maybe calling your boss and leaving a rambling 20-minute message about how much you hate your job. In 1990, when entrepreneur and investor Mark Cuban was 32, he drunk dialled American Airlines after selling his first startup, MicroSolutions, for $6 million. Jeff Bezos backs a platform that lets anyone invest in rental homes for as little as $100 — 6 ways to build wealth like a landlord without actually being one Dave Ramsey warns nearly 50% of Americans are making 1 big Social Security mistake.
Here's what it is and 3 simple steps to fix it ASAP The tax breaks in Trump's 'big beautiful bill' expire after 2028. Here are 4 moves to make before the window closes "My buddies and I went out and just got destroyed," he told the Club Shay Shay podcast back in 2024. "They're like, 'What do you think you're going to do with all this money?' And I'm like, 'I don't care about cars or houses, but boy, you know, I fly a lot for work.'" He ended up spending $125,000 on an AAirpass, a lifetime pass that guaranteed him a first-class seat on any American Airlines flight for the rest of his life.
Worth noting, the airline halted memberships in 2022 and sunsetted the program in 2024. That didn't affect Cuban, though. Back in 1999 he splurged on a $40 million private jet after selling his Broadcast.com streaming platform to Yahoo for $5.7 billion in stock.
While your odds of winning the lottery are slim, there are other ways you might find yourself on the receiving end of a large sum of cash: a work bonus, an inheritance, a life insurance payout or the sale of a business. If you receive a financial windfall, especially one that's unexpected, it can be tempting to go out and splurge on a big-ticket item like a sports car or luxury vacation. And that's okay, if the math adds up.
One common rule of thumb that can help you manage a windfall is to set aside 5% for guilt-free spending. That means if your windfall is $10,000, you'd have $500 for splurging, while a $100,000 windfall would leave you with $5,000 in fun money. For example, Cuban's $125,000 splurge was less than 5% of the total sale of MicroSolutions (which would be $300,000).
But, after taxes, he actually only took home about $2 million, so he would have had about $100K for splurge money, if he were following the 5% rule of thumb. Even though he was drunk dialling, Cuban did a few things right. His splurge wasn't on a depreciating asset, like a sports car (a new car depreciates as soon as you drive it off the lot, losing about 30% of its value over the first two years).
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