Insider to the wealthy: Even my billionaire clients are worried their kids won’t keep jobs in this market
The job market anxiety sweeping America has reached an unexpected demographic: the ultra-wealthy. According to Patrick Dwyer, managing director at Miami-based Aligned by NewEdge Wealth, even billionaires are losing sleep over their children's career prospects.
A Changing Landscape for the Next Generation
Dwyer works with clients whose net worth ranges from $100 million to over $1 billion, and he's noticed a troubling pattern. These ultra-high-net-worth individuals are increasingly worried that their children—typically aged 22 to 35—won't be able to build sustainable careers in traditionally stable fields like technology, law, and medicine.
This concern isn't unfounded. The broader job market tells a sobering story. Recent college graduate unemployment has climbed steadily for three consecutive years, hitting 9.7% in September 2025, according to Federal Reserve data. Meanwhile, 2024 marked the weakest hiring year in the U.S. since 2009, excluding the pandemic-disrupted 2020.
It's Not About the Money—It's About Agency
To be clear, we're not talking about financial ruin. As Michael Hans, chief investment officer at Citizens Wealth, points out, people with this level of wealth aren't at risk of losing their homes or canceling luxury vacations. Most could comfortably support their children's living expenses indefinitely.
But for the ultra-wealthy, the stakes are different. "They're realizing that if they don't pass on more meaningful wealth to their children, or their children are not able to accumulate wealth... their kids could have less agency over their lives than they did," Dwyer explains.
It's about autonomy, purpose, and the ability to make choices without compromise—things money can buy, but a career provides more meaningfully.
Why Traditional Paths Are Losing Appeal
What's causing this hiring freeze? Experts point to several culprits:
Artificial intelligence is reshaping entire industries, though nobody knows exactly how many jobs it will ultimately replace or when.
Economic uncertainty is making established workers hold onto their positions longer. Rising costs of living and home ownership mean people are staying put rather than creating openings for younger workers.
"Folks are kind of just sitting still," says Nich Tremper, senior economist at payroll platform Gusto. "They're not looking for new roles, they're not leaving their current roles. Without those new jobs available, it's hard for an entry-level employee to get their foot in the door and start their career."
For billionaire parents who climbed the ladder through competitive schools, prestigious internships, and well-leveraged connections, the playbook that worked for them increasingly looks obsolete.
The Entrepreneurial Pivot
Faced with this uncertainty, Dwyer's clients are making a surprising pivot: instead of pushing their kids toward traditional career paths, they're actively encouraging—and funding—entrepreneurship.
This represents a significant shift in thinking. Entrepreneurship typically means low initial pay, grueling hours, and high failure rates. Small-business advisors usually caution against starting a company out of career desperation or the need for stable income.
But ultra-wealthy families have a unique advantage: a safety net thick enough to absorb multiple failures. Their children can launch startups, learn from mistakes, iterate, and try again without risking their financial security.
The goal isn't just to create successful businesses, though. These parents want their kids to develop resilience, adaptability, and a robust work ethic—traits that may matter more than credentials in an unpredictable future economy.
Building Skills That Matter
Dwyer sees real value in this approach. "These young entrepreneurs, if you sit and talk to these 25- or 26-year-olds, they understand marketing. They understand finance. They understand how to build a business," he observes. "It's really something that is worthwhile... and I think they will be increasingly sought after in the marketplace."
The irony is rich: in trying to protect their children from an uncertain job market, billionaires may be preparing them better than traditional education ever could.
What This Means for the Rest of Us
While most families don't have the luxury of bankrolling multiple startup attempts, there's a broader lesson here. The ultra-wealthy are responding to genuine market signals that affect everyone. When people with every advantage still worry about their kids' career prospects, it suggests we're all navigating a fundamentally transformed economic landscape.
The skills these wealthy parents want their children to develop—entrepreneurial thinking, adaptability, cross-functional business knowledge—are valuable regardless of whether you're launching a startup or climbing a corporate ladder. The difference is that most of us need to develop them while maintaining financial stability, not with a billion-dollar cushion beneath us.
As the job market continues to evolve, perhaps the real question isn't whether to pursue entrepreneurship, but how to cultivate an entrepreneurial mindset wherever we are.