How 4 people turn ordinary skills into side hustles—and make up to $2,000 a day from rich clients

On Gloria Richards’ first day of work, she was dropped off at an airport, introduced to children she’d never met and flown on a private jet to a rented-out resort in Barbados.

The 34-year-old is primarily an actress, but on the side, she’s a travel nanny for billionaires in New York. Often, she works around the clock while abroad, meaning the side gig sometimes supersedes her acting career.

But she’s compensated more than other caretakers: A 12- to 15-hour per day can net her up to $2,000, she says, which translates to between $133 and $167 per hour.

Plenty of people do gig work to pick up extra cash. A lucky few perform those jobs for some of the country’s richest individuals, making significantly more money by virtue of their employers — often doing jobs as simple as running errands or completing random tasks at their bosses’ whims.

It may seem like anyone could watch wealthy people’s dogs, children or houses while enjoying perks like free celebrity-branded products, cars, international travel and lavish work backdrops. But working with billionaires requires “extraordinary personalities,” says Jackie Mann, the director of operations at New York-based household staffing firm Madison Agency.

“The competency one has to care for a child isn’t uncommon,” Mann says. “The qualities it takes to work for the ultra-wealthy is patience and a nuanced perception of anticipating a person’s needs.”

It also involves access and, often, luck. CNBC Make It spoke with multiple individuals who have elevated their gig jobs by working for the ultra-wealthy. Here’s what they said about their lucrative side hustles:

Nanny-matching site Care.com advises New York families to pay full-time nannies $21.25 per hour, the company’s website says. The city’s “high-end” nannies average $30.45 per hour, according to ZipRecruiter data.

Richards’ rate far outstrips those figures. Nannying is responsible for 80% to 90% of her income, she says: “I could nanny for, like, two months at the top of the year, and I’d be fine for the rest of the year.”

When Richards moved to New York more than a decade ago, she worked in the childcare department of a Reebok Sports Club, which was later acquired by Equinox. There, she met affluent families who eventually asked her to babysit. Eventually, she needed an agent to help her manage all her contracts, leading her to Madison Agency.

But her responsibilities rarely resemble traditional child care, she says. Rather, she’s essentially a “personal assistant” for the kids — coordinating their social calendars with piano, fencing and language lessons, she explains.

Margaret Myers, a 32-year-old writer, turned to nannying for one-percent families to support herself while writing a book — and says she had similar experiences. In her case, personal assistance requests sometimes extended beyond the kids.

“[Some parents] would always be like, ‘Oh, can you put together a cheese plate tonight for my work friends?'” Myers says. “And I would be like, ‘Well, that’s not child care.’ But it’s so hard, because you’re there to help.”

Myers’ rates were much closer to the New York average, she says — $30 per hour as a full-time nanny, and roughly $20 per hour for part-time babysitting gigs on apps like Hello Sitter and Bambino Sitters. Those apps cater to last-minute requests, which skew toward families that can afford steeper prices, she says.

Alongside a bookstore job, they still helped pay the bills. “As a writer, I know that nannying is the thing that will always make me the most money in my life,” says Myers.

A typical Uber driver in New York makes just over $45,000 per year, according to Glassdoor data. Frank Dorfman’s job is similar — carting passengers around the city on-demand — but his pay starts at $1,000 per day, he says, because his lone client is particularly wealthy.

Dorfman, a 53-year-old retired New York police detective, started chauffeuring through Madison Agency in 2019. His client is a well-known financier and their family, and his schedule is unpredictable, he says: He works anywhere from one to five days per week, and sometimes goes a week or two without driving at all.

He makes about as much money chauffeuring as he does from his police pension, helping him put his three children through small, expensive liberal arts colleges, he says. His black Chevrolet Suburban ferries the family on errands, or from their Park Avenue home to school.

Occasionally, if the family is running late to the airport, Dorfman can push the limits of traffic rules — counting on his background to bail him out. “If I was to get pulled over or something like that, I show my ID and get professional courtesy most of the time,” he says.

Frank Dorfman (right), alongside one of his daughters, started chauffeuring four years after he retired as a New York police detective.

Frank Dorfman

That’s not something Denny Rodriguez has to reckon with — at least, not yet. Rodriguez, 30, is a New York-based driver for Fortis, a Greenville, South Carolina, company that’s essentially Uber for ultra-wealthy customers.

“The core client would be someone with a net worth of over $600 million, usually owning one or more private jets,” says Fortis CEO Nathan Foy.

Rodriguez began driving for a New York neighborhood service roughly a decade ago, while enrolled in the city’s police academy. He dropped out of the academy after realizing he could make more money by driving full-time.

In those days, he got mugged on the job. His car got broken into. He ran out of gas multiple times, due to a malfunctioning gas gauge.

At one point, he struck up a contract with a Ritz-Carlton hotel, learning the ropes of chauffeuring for wealthier clients. And after Fortis approached the hotel’s concierge asking for its best chauffeur, Rodriguez was recruited to the company, he says.

Now, he has to pay for his own overhead, from his Cadillac Escalade and BMW 740i to the suits he wears while driving them — but the income is worth it. Fortis clients typically pay around $550 per S-Class trip in a major city, which gets split between the company and chauffeur, Foy says.

Foy declined to disclose the split’s percentages, but Rodriguez says the tips are additionally generous: Once, a passenger tipped him $5,000.

It’s like “day and night,” he says.

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