For executive assistants in this world, job descriptions go far beyond diary management and travel bookings. We’re talking about learning to drive a Zamboni, managing a $50 million art collection, or arranging the sale of a million-dollar wine cellar — all in a day’s work.
According to dailymail.co.uk, the number of billionaires is climbing, and so are the demands placed on the people who keep their empires running. For EAs at this level, the salaries are astronomical – $250,000 to $500,000 is not unheard of – but so is the pressure. You’re often on call 24/7, ready to jet off for weeks at a moment’s notice, and expected to deliver on requests that range from the complicated to the bizarre. Interestingly, Australia is home to 161 billionaires, an increase from 150 in 2024.
Turning “impossible” into “done”
Jamie Gagliano, who served nine years as Chief of Staff for hedge-fund billionaire Larry Robbins, once oversaw the construction of a full-sized ice hockey rink inside one of his mansions — in a town with tough zoning rules. It took a team of specialists and a lot of creative problem-solving to get the project across the line. Once finished, she even hopped on the Zamboni herself.
The Great Downsizing… billionaire style
For Sarah Korpela, a property manager in Aspen, “moving house” once meant selling seven luxury cars, five ATVs, seven motorcycles, several horses, and a $1 million wine collection. The wine went for $400,000 to a local restaurant — but when her client asked her to ship his gun collection overseas, she drew the line. (“There’s something called trafficking,” she reminded him.)
Always on call — even while sleeping
Kelly Fore Dixon, who managed the Beverly Hills estate of late Microsoft co-founder Paul Allen, slept with her phone by her ear. She was responsible for everything from a private cinema to $50 million worth of art — including a Monet that survived an accidental soda spray… from Allen himself.
The small things matter most
Then there are the tiny, exacting details. Perfectly ironed sheets. Pillows fluffed to just the right angle — or karate-chopped in the middle. Chefs paid six-figure salaries to know not only their employer’s favourite dishes, but their least favourite.
Former Kim Kardashian assistant Stephanie Shepherd once revealed that part of her morning routine was handing Kim her Starbucks coffee, but only after removing the cardboard sleeve.
The most outrageous request of all
Of course, eccentricity is part of the package. Staffing agency founder Brian Daniel recalls one client whose basement doubled as a private “dungeon.” Another billionaire insisted his assistant be comfortable with his nudist lifestyle — meaning, some mornings, you’d arrive to work and be greeted with… well, nothing left to the imagination.
And that, perhaps, is the most outrageous request of all: that no matter how unusual, inconvenient, or eyebrow-raising the task, you’re expected to deliver it with composure, efficiency, and absolute discretion.
Because in the billionaire world, “out of the box” isn’t the exception – it’s the job description.
