What it's really like to work for the world's richest people

The truth about working with billionaires, as revealed by insiders

<p>John Lamparski/Getty Images</p>

John Lamparski/Getty Images

Working with a billionaire business icon at the top of their game can have its challenges, but the rewards are often breathtaking: think enormous bonuses, freebie holidays, and even designer shopping sprees.

How do we know? Because close colleagues in the inner circles of the world's highest-flyers have revealed their leadership styles, professional habits, and more.

Read on to get the inside scoop on what it's really like to work for some of the world's most successful billionaires.

All dollar amounts in US dollars

Taylor Swift

<p>Amy Sussman/Getty Images</p>

Amy Sussman/Getty Images

As superstar billionaire bosses go, Taylor Swift is among the kindest and most generous, with staff past and present singing her praises.

Swift's former personal assistant Heather Wirth said it was a pleasure working for the "very genuine, very real" A-lister. Dancer Charity Baroni, who scored her big break accompanying Swift on the hitmaker's early tours, has also taken to TikTok to gush about her as "an incredible boss and friend".

Swift's hairstylist Jemma Muradian has referred to her as a "beautiful soul", while famous colleagues like Rebel Wilson, who appeared with Swift in the 2019 Cats movie, say she's just plain awesome to work with.

Taylor Swift

<p>Gareth Cattermole/TAS24/Getty Images</p>

Gareth Cattermole/TAS24/Getty Images

On top of being friendly, caring, and approachable, Swift is also incredibly generous towards her staff.

Unlike a lot of other musicians, she provides insurance for her dancers. She even treated 125 of her team to an all-expenses-paid luxury trip to Australia.

Most impressive of all, the chart-topper doled out a staggering $197 million (£158m) in bonuses by the time The Eras Tour wrapped, including a "life-changing" $100,000 (£80k) for each of the truck drivers, as well as similar payouts for the dancers, riggers, sound technicians, and catering team.

She also regularly donates to charity. Most recently, she gave $1 million to the non-profit Feeding America in December 2025 and followed this up with another $1 million donation in the same month to the American Heart Association.

Jeff Bezos

<p>Michael M. Santiago/Getty Images</p>

Michael M. Santiago/Getty Images

According to Jeff Bezos's unofficial biographer, Richard M. Brandt, the Amazon founder is generally regarded as something of a visionary by former execs who have worked closely with him.

Shel Kaplan, the e-commerce platform's first employee, paints Bezos as "a brilliant businessman with a strong vision". Ex-programmer Peri Hartman has highlighted his former boss's goofy side, while Amazon's former head of hiring, Brian Krueger, has said that Bezos's trademark "honking" laugh was infectious, often echoing through the corridors of the company's HQ and lightening the atmosphere.