As the number of billionaires continues to grow, so does the list of their out-the-box demands and the number of people tasked with catering to them.
Roles within the entourage of the super elite include everything from housekeepers and chauffeurs, to personal travel experts and tech support.
Between 2020 and 2024, the combined wealth of the top 10 billionaires in the United States increased by about 88 percent, per the Institute for Policy Studies.
And with that extra cash, rich people are increasingly buying second, third and fourth homes, with ever-increasing amenities that need constant upkeep.
One recent job listing with the Celebrity Personal Assistant Network advertised a $250,000 position working as an executive assistant to a New York City billionaire, although staff of wealthy individuals can make as much as $500,000 per year.
Applicants to that specific post required an Ivy League degree, must be on-call 24/7 and be prepared to leave town for ‘weeks at a time with a moments notice’.
High standards like these are just the tip of the iceberg when it comes to billionaire’s demands.
Here several industry insiders revealed the extent of their employers’ requests, which range from outrageous to illegal.
As the number of billionaires continues to grow, so does the list of their out-the-box demands, according to those in their entourage
Roles within the entourage of the super elite include everything from housekeepers and chauffeurs, to personal travel experts and tech support. Pictured: Kim Kardashian’s sprawling $70 million mansion in Malibu, California
Sarah Korpela (left) and Jamie Gagliano have over twenty years of experience managing the lives of ultra-wealthy clients between them. Gagliano worked for nine years as the chief of staff for hedge-fund executive Larry Robbins, a billionaire by net worth
Jamie Gagliano, is a real-estate agent at Douglas Elliman who used to be the chief of staff for hedge-fund executive Larry Robbins.
She oversaw the billionaire’s homes and vehicles, including his personal helicopter.
In her role, Gagliano led a staff of 25 people for Robbins. A job like hers pays anywhere from $300,000 to $500,000 annually.
Robbins, a lifelong hockey fan, retrofitted one of his mansions in Alpine, New Jersey, so it would have a full sized ice hockey rink. And Gagliano was tasked with getting this done.
She described it as one of the most complicated things she’s ever had to do in her career.
‘This isn’t just building a house, right? It’s building a house in an area that had very strict zoning rules,’ Gagliano told Daily Mail. ‘Building the team to get that done took experts across several key areas, and it literally took a village to figure it out.’
‘It’s about how do you figure out how to give him the results he’s looking for, where it’s essentially there’s a hockey rink on the inside, and make it look beautiful on the outside.’
Once everything was done, Gagliano soon found herself learning how to drive a Zamboni. It was just one of the odd yet fun perks of working for a high-net-worth individual, she said.
‘When again am I going to have the opportunity to sit on a Zamboni. Probably never. So I was like, I’m going to hop on that while I have the chance,’ she said.
She said driving it was a mix between driving an automatic car and a stick shift. She also compared it to driving a tractor.
Sarah Korpela has spent 15 years working as property manager for wealthy clients and in that time, she has seen no shortage of outlandish requests.
Once, Korpela helped one of her clients move out of his roughly 10,000-square-foot home and sell seven of his cars, five ATVs, seven motorcycles and a few horses, she told The Wall Street Journal.
Korpela, president of Luxury Estate Managers of Aspen, also helped him sell his $1 million wine collection to a local restaurant for about $400,000.
But she drew the a line when a client asked her to ship him his gun collection internationally.
‘There’s something called trafficking,’ she recalled telling him. She said she sold the guns instead.
‘If it’s legal, I have done it in this business,’ she added.
Jamie Gagliano, a real-estate agent at Douglas Elliman who used to be the chief of staff for hedge-fund executive Larry Robbins, oversaw the billionaire’s homes and vehicles. This included his personal helicopter.
‘We’re talking about assets that are sometimes north of $10 million – each of them,’ she told The Journal.
In her role, Gagliano led a staff of 25 people for Robbins. A job like hers pays anywhere from $300,000 to $500,000 annually.
While Gagliano was working for Larry Robbins (pictured), she was heavily involved in bringing his dream of an ice hockey rink on his property to fruition
Robbins’ home in Alpine, New Jersey, is pictured on the right. The indoor hockey rink is off to the left on the property and is surrounded by large trees
Robbins, a lifelong hockey fan, retrofitted one of his mansions in Alpine, New Jersey, so it would have a full sized ice hockey rink while Gagliano was working for him.
This meant that Gagliano soon found herself on a crash course for how to drive a Zamboni.
She was heavily involved in working through the complex approval process.
She also acted as Robbins’ representative when discussing the project with a team of architects and engineers, an experience she credits with nurturing her interest in real estate.
Another home that was in Robbins’ portfolio during Gagliano’s nine-year tenure was an absolute behemoth of a home sitting on 43 acres of pristine land in Mahwah, New Jersey.
The home was bought in 2009 by Robbins’ then-wife Amy Towers, who was once the COO for his company Glenview Capital Management.
Complete with a 20 stall horse barn, an indoor riding area, a wine cellar and a football field, it clearly wasn’t the average house.
The 10-bed, 14-bath home is now on the market for $22.5 million. The property taxes alone are estimated to be $120,000 a year.
Kelly Fore Dixon served as the estate manager for the late Microsoft co-founder Paul Allen and recalled sleeping with her phone by her ear
The type of work Gagliano and people like her do isn’t for the faint-hearted, as it often requires you to be on call all the time for any sort of emergency.
That was certainly how it was for Kelly Fore Dixon, who served as the estate manager for the late Microsoft co-founder Paul Allen.
Allen died in October 2018 after a decades-long battle with cancer. He had a large portfolio of properties all over the world.
She managed his home in Beverly Hills, California, and recalled sleeping with her phone by her ear.
The 12,000-square-foot estate had a recording studio, a home theater, a pool and 30 HVAC units, Dixon told The Journal.
All of that was in the purview of Dixon, a maintenance worker, two housekeepers and a gardener – plus private security and about 80 subcontractors.
The staff were ‘silent and unseen’ when Allen was around the property, said Dixon, who now runs the consulting firm Estate Management Systems.
The house had $50 million worth of artwork, including a Monet that was accidentally sprayed with soda.
‘The art contractor came in for an annual inspection and said, “What the hell have you done to the painting?”‘ Dixon recalled. It turned out that Allen himself was the culprit.
Allen died in October 2018 after a decades-long battle with cancer. He had a large portfolio of properties all over the world.
Shepherd helped out with various aspects of Allen’s empire. Pictured: Allen’s 414-foot yacht docked in Aydin, Turkey, on April 27, 2015
However, there are also the mundane requests that staff, particularly housekeepers, must keep on top of as well.
‘People are passionate about how their pillows look,’ Korpela said. ‘Do they like sheets ironed? Pillow straight or karate chopped? What’s on the bedside table?’
Attention to detail is just as important for chefs who work for one percenters. They can make anywhere from $100,000 to $300,000 per year.
‘Before we know what food they do like, we really want to know what food they don’t like,’ said chef Mike Shand, co-founder of Elite Private Chefs, a placement agency that has cooked for Beyoncé and Adele.
However, it’s not just the fact that these staffers have to be at the top of their game. They have to be on it just about 24/7.
That’s according to Stephanie Shepherd, who worked as Kim Kardashian’s personal assistant from 2013 to 2017.
‘Obviously Kim and I text all day every day,’ Shepherd told Refinery29 in November 2017. ‘From the second we wake up until we go to bed, so we just bounce off ideas.’
Kim herself has previously disclosed that she has her assistant carry out even the most minute of tasks – including removing the cardboard sleeve from her Starbuck’s cup before presenting it in the morning.
Servants for the rich and powerful also have to deal with some eccentric personalities.
Brian Daniel, who worked as a personal assistant for years before founding his own staffing firm, said he’s run into some truly strange things.
‘There was this one billionaire who had, it could only be described as a dungeon in his basement, for fetishes and stuff like that,’ he told The Cut last year.
‘I had one client who was a financial genius, and it turns out he was a nudist. He walks around in his birthday suit.
‘They said the assistant would have to be okay with that because it’s random — you come to work, he opens the door, and voilà,’ he added.
Still many, staffers form close relationships with their bosses. In 2019, Jeff Bezos gave a public shout out to his longtime assistant John Connors.
‘You’re a big reason I’m able to be so busy and not go nuts — in fact, you somehow even make it calm,’ Bezos gushed.
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