Not every billionaire started their career in a corner office or landed a coveted analyst position on Wall Street. Mark Cuban certainly didn’t. Before becoming a billionaire entrepreneur, he was selling trash bags, slicing deli meat and working as a bartender. He even taught dance lessons.
None of those jobs screamed future billionaire. But for Cuban, they offered something more valuable than an impressive job title: the chance to show up, work hard and learn a thing or two along the way.
And he believes young Americans could benefit from taking a similar approach.
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“Don’t get the perfect job because those are hard to find. Just get a job,” Cuban said on an episode of The Diary of a CEO. “Even though your life mission isn’t to be the manager of a McDonald’s or a Dairy Queen or whatever, the fact that you can show a future employer that you moved up the line…that’s what you need.”
When ‘just get a job’ isn’t so simple
Showing up, working hard and learning on the job is advice that has stood the test of time, even if the position isn’t exactly what you had in mind for your future. But for young Americans today, getting that first opportunity is becoming more difficult.
Entry-level jobs haven’t disappeared, but the opportunities available to younger workers are shrinking, particularly in industries most vulnerable to artificial intelligence.
According to an August 2026 update of Stanford Digital Economy Lab’s Canaries in the Coal Mine study, employment among workers ages 22 to 25 in occupations most exposed to AI was roughly 19% below where it would have been had it followed the same trajectory as jobs less exposed to the technology. Just a year earlier, that gap stood at 15%.
But for some job seekers, even landing a position at McDonald’s is proving easier said than done.
“My applications for grocery stores, Walmart, Target and even McDonalds came back with automatic rejection letters,”one frustrated Reddit user wrote in a post about their struggles to find work. “Those jobs are what a high school teenager used to be able to land with ease. As a grown adult with years of experience, I’m seriously being turned away from Walgreens?”
They recalled applying to 20 jobs at age 16 and hearing back from five employers. Today, those same applications go unanswered.
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The catch-22
Finding that first job can feel like a frustrating contradiction. Employers expect applicants to have experience, yet getting that experience often depends on someone being willing to hire them in the first place.
Frances Li, founder and director of Biscuit Recruitment, says it’s a challenge that’s becoming increasingly difficult for younger applicants to overcome.
“There’s also a catch-22. Young applicants are told they need experience to get a job, but they need a job to get experience,” Li told Moneywise.
With online applications making it easier to apply for jobs, even basic positions can attract a flood of candidates. Li says employers have become more selective, leaving applicants with little experience struggling to stand out.
“That’s demoralising, and I don’t think it reflects their ability or attitude,” Li added.
Even a college degree isn’t necessarily enough to secure a position that requires one. According to the Federal Reserve Bank of New York, unemployment among recent graduates stood at 5.6% in the second quarter of 2026, while underemployment reached 42%. That means more than four in 10 employed recent graduates were working in jobs that typically don’t require a college degree.
Your first job doesn’t have to be your dream job
Despite the challenges facing young workers, Li believes there’s some wisdom in Cuban’s advice. Waiting for the perfect opportunity can mean missing out on valuable experience, even if the job isn’t exactly what someone had in mind.
In comments to Fortune, Cuban encouraged young workers to learn how to work for a boss, get along with colleagues and understand how their employer makes money. He also stressed the importance of finding ways to become more productive and move up the ladder.
While working at McDonald’s or Dairy Queen might not be everyone’s dream career, Li says it doesn’t have to be a permanent detour.
“Your first job rarely defines where you end up,” Li said. “It’s a stepping stone, and you can keep applying for roles in your chosen field while you build experience. It’s usually easier to move from one job to the next than from nothing to something.”
After all, Cuban went from selling trash bags to building a billion-dollar fortune. Not everyone who takes a job at McDonald’s or Dairy Queen will become the next Cuban, but that’s not really the point. A first job can open doors to opportunities that might not have seemed possible at the start.
Of course, in today’s job market, the challenge isn’t always convincing young Americans to start somewhere. It’s finding an employer willing to give them that first chance.
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Victoria Vesovski is a Toronto-based staff reporter at Moneywise covering personal finance, lifestyle and trending news. She holds degrees from the University of Toronto and New York University, and her work has appeared on platforms including Yahoo Finance, MSN Money and Apple News.
