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Gen Z Is Swapping Cubicles For Six-Figure Gigs Working For Billionaires

MarketDash Editorial Team
21 days ago
A growing number of young workers are ditching traditional careers to become nannies, chefs, and estate managers for the ultra-wealthy, earning up to $250,000 annually plus luxury perks. As wealth concentrates at the top, Gen Z is finding better pay and benefits working directly for billionaires than climbing corporate ladders.

Here's a career pivot you probably didn't see coming: Gen Z workers are increasingly choosing to work directly for billionaires rather than slog through traditional corporate jobs. And the economics actually make sense.

As wealth continues pooling at the very top, a parallel economy has emerged where young professionals trade cubicles for megayachts, corporate ladders for estate management, and standard benefits packages for something far more lucrative.

The New Math Of Wealth Management

Take Cassidy O'Hagan, 28, who started her career in orthopedic medical sales pulling in $65,000 a year while logging brutal hours in hospitals. Now she works as a nanny for ultra-wealthy families, earning between $150,000 and $250,000 annually. The job comes with full benefits plus perks that sound lifted from a lifestyle magazine: private chefs, custom wardrobes, and Uber rides to work.

"My orthopedic medical sales job could never compete," she told Business Insider.

Then there's Julia Dudley, 26, who invested in multiple degrees and culinary school before leaving restaurant work to become a private chef in the Hamptons. She discovered that preparing just two or three meals a day over a single summer can generate a six-figure income.

"I was like, okay, I can make my own hours, I can make more money, I'm my own boss," she said. A few months of seasonal work now eclipses what she earned in traditional food service roles over an entire year.

Small Armies Managing Big Fortunes

This isn't a niche trend. Brian Daniel, who runs the Celebrity Personal Assistant Network, says the explosion of ultra-wealthy individuals has created massive demand for elite household staff. "Each one of these billionaires employs small armies of people to cater to their every whim," he told Business Insider. He estimates there are now 1,000 staffing agencies operating worldwide, with half based in the U.S.

The compensation reflects that demand. Job listings routinely advertise salaries well into six figures. A recent posting for a "head of personal assistants" offered up to $280,000. Another for a nanny topped out at $150,000. A "director of residences" position, requiring the employee to fly between properties in Colorado, California and New York, pays between $200,000 and $250,000 annually.

The Hidden Costs Of Serving The Rich

But these roles aren't exactly cushy despite the perks. Staff members are often expected to be perpetually on call and handle whatever needs arise, including less glamorous tasks like cleaning up after a billionaire's dog. "The stress can be more than even on Wall Street," Daniel said.

Privacy is paramount. Most positions require extensive nondisclosure agreements and immaculate social media profiles. O'Hagan, who now works for an unnamed high-profile New York family as part of an eight-nanny rotation, explained the reality: "You're not just working for a family, you're living alongside them, immersed in their rhythms, dynamics, and private moments."

The work can also be isolating. O'Hagan has spent holidays away from her own family. Still, she says the trade-offs are worth it. "This career has offered stability and meaning and a level of personal connection that I hadn't really found anywhere else yet," she told Business Insider.

Building A Career On Billionaire Infrastructure

O'Hagan isn't planning to nanny forever. She's now launching her own agency and coaching service to help others break into the field. The opportunity has even cascaded through her family—her younger brother followed her lead and now works as an assistant to a celebrity esthetician in Beverly Hills, California.

The broader pattern here is pretty straightforward: as economic resources concentrate among fewer people, working directly for those people becomes an increasingly rational career choice. Gen Z seems to have figured out that if stability and high compensation are flowing through the wallets of the ultra-wealthy, you might as well position yourself close to the source.

It's not exactly the American Dream their parents imagined, but it might be the most pragmatic response to the economy they've inherited.

Back to News

Gen Z Is Swapping Cubicles For Six-Figure Gigs Working For Billionaires

MarketDash Editorial Team
21 days ago
A growing number of young workers are ditching traditional careers to become nannies, chefs, and estate managers for the ultra-wealthy, earning up to $250,000 annually plus luxury perks. As wealth concentrates at the top, Gen Z is finding better pay and benefits working directly for billionaires than climbing corporate ladders.

Here's a career pivot you probably didn't see coming: Gen Z workers are increasingly choosing to work directly for billionaires rather than slog through traditional corporate jobs. And the economics actually make sense.

As wealth continues pooling at the very top, a parallel economy has emerged where young professionals trade cubicles for megayachts, corporate ladders for estate management, and standard benefits packages for something far more lucrative.

The New Math Of Wealth Management

Take Cassidy O'Hagan, 28, who started her career in orthopedic medical sales pulling in $65,000 a year while logging brutal hours in hospitals. Now she works as a nanny for ultra-wealthy families, earning between $150,000 and $250,000 annually. The job comes with full benefits plus perks that sound lifted from a lifestyle magazine: private chefs, custom wardrobes, and Uber rides to work.

"My orthopedic medical sales job could never compete," she told Business Insider.

Then there's Julia Dudley, 26, who invested in multiple degrees and culinary school before leaving restaurant work to become a private chef in the Hamptons. She discovered that preparing just two or three meals a day over a single summer can generate a six-figure income.

"I was like, okay, I can make my own hours, I can make more money, I'm my own boss," she said. A few months of seasonal work now eclipses what she earned in traditional food service roles over an entire year.

Small Armies Managing Big Fortunes

This isn't a niche trend. Brian Daniel, who runs the Celebrity Personal Assistant Network, says the explosion of ultra-wealthy individuals has created massive demand for elite household staff. "Each one of these billionaires employs small armies of people to cater to their every whim," he told Business Insider. He estimates there are now 1,000 staffing agencies operating worldwide, with half based in the U.S.

The compensation reflects that demand. Job listings routinely advertise salaries well into six figures. A recent posting for a "head of personal assistants" offered up to $280,000. Another for a nanny topped out at $150,000. A "director of residences" position, requiring the employee to fly between properties in Colorado, California and New York, pays between $200,000 and $250,000 annually.

The Hidden Costs Of Serving The Rich

But these roles aren't exactly cushy despite the perks. Staff members are often expected to be perpetually on call and handle whatever needs arise, including less glamorous tasks like cleaning up after a billionaire's dog. "The stress can be more than even on Wall Street," Daniel said.

Privacy is paramount. Most positions require extensive nondisclosure agreements and immaculate social media profiles. O'Hagan, who now works for an unnamed high-profile New York family as part of an eight-nanny rotation, explained the reality: "You're not just working for a family, you're living alongside them, immersed in their rhythms, dynamics, and private moments."

The work can also be isolating. O'Hagan has spent holidays away from her own family. Still, she says the trade-offs are worth it. "This career has offered stability and meaning and a level of personal connection that I hadn't really found anywhere else yet," she told Business Insider.

Building A Career On Billionaire Infrastructure

O'Hagan isn't planning to nanny forever. She's now launching her own agency and coaching service to help others break into the field. The opportunity has even cascaded through her family—her younger brother followed her lead and now works as an assistant to a celebrity esthetician in Beverly Hills, California.

The broader pattern here is pretty straightforward: as economic resources concentrate among fewer people, working directly for those people becomes an increasingly rational career choice. Gen Z seems to have figured out that if stability and high compensation are flowing through the wallets of the ultra-wealthy, you might as well position yourself close to the source.

It's not exactly the American Dream their parents imagined, but it might be the most pragmatic response to the economy they've inherited.

    Gen Z Is Swapping Cubicles For Six-Figure Gigs Working For Billionaires - MarketDash News