While in his 20s, shortly after moving to Dallas with only $60 in his pocket, Cuban tried every money-saving hack he could think of to stretch what little cash he had, he told Bill Maher on a recent episode of the “Club Random Podcast.” Some markets still offer discounts for late-night shoppers, according to a 2021 Instacart report. In the evenings, they might mark down perishable items that won’t last until the next day, like fresh produce, meat and baked goods.

One of Cuban’s strategies: Going to supermarkets in the middle of the night to score deals on food. “I used to go to the grocery store at midnight because they lowered the price of chicken and these big [bags of] French fries to $1.29,” he said on the podcast. “And I would buy a bunch of them.”

More commonly, major grocers offer deals on specific days of the week. Several grocery stores begin weekly specials on Wednesdays, according to the Instacart report. That’s likely because the bulk of their customers shop on the weekend, analyst and founder of Supermarket Guru Phil Lempert told TODAY in 2018.

Cuban, who lived in a three-bedroom apartment with six roommates at the time, didn’t just look for deals on food, though. He told Maher that while he needed to get to and from his bartending gig and make it to job interviews, he couldn’t afford a car.

Cuban had “credit cards cut up” and “bill collectors” on his trail, he told Maher. But one day, he was with his friends when he saw an abandoned vehicle on the side of the road. They pulled over, and the car seemed to be in good shape. Better yet, it was unlocked and had a thick envelope full of loan papers on the front seat.

“It wasn’t fed up,” Cuban explained. “I knew from my own personal experience someone abandoned it because they couldn’t make the payments.”He took the papers and called the bank the next day. Cuban asked if he could take over the payments, and the bank agreed.

Other 20-somethings wouldn’t likely be able to copy his roadside strategy, he told Maher. After all, not everyone can rely on finding a working car left untouched on the side of the road. Plus, Cuban pointed out that it’s nearly impossible these days to avoid an automated assistant when you call the bank.

Still, Cuban has said in the past that his days of scraping by helped motivate him. “I had nothing. So I had nothing to lose, right? It was all about going for it,” Cuban told The Dallas Morning News in a 2011 interview. That attitude led Cuban to take a shot at selling software, despite having been fired from multiple jobs. He then launched his own computer consulting business, MicroSolutions, which he sold for $6 million in 1990 at the age of 32.


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