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 14 of the world's most successful billionaires.

All dollar amounts in US dollars

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 says 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 hair stylist 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.

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, and she's generous in terms of holiday entitlement – in 2020, for example, she made Juneteenth an official staff holiday.

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. 

Taylor, if you're hiring anytime soon, just let us know...

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.

But while he was jovial at times, Bezos was never lax when he was CEO of the e-commerce and cloud-computing behemoth.

Like many other world-class business leaders, Bezos has a knack for getting the best out of the people working for him. Speaking to Business Insider, Bezos's former executive assistant, Ann Hiatt, described her time at Amazon as "relentless" and "unforgiving". Bezos "doesn't suffer fools", with Kaplan describing him as a "demanding micromanager".

Krueger attributes this to Bezos's lofty standards, revealing: "He expects a lot out of people. Is that being a tyrant? No, not if you want to work hard and grow. If you're lazy, don't get anywhere near Jeff. He focuses on those who deliver."

Peri Hartman noted that working with Bezos was “stressful in a good way. Jeff has a very positive attitude toward employees”. 

A charismatic leader with bags of empathy who nurtures and supports her employees, Oprah inspires fierce loyalty from the people working for her.

Known for being ridiculously generous, the media mogul rewards her staff handsomely for their efforts. During the first season of The Oprah Winfrey Show back in 1986, Oprah gifted each of her team $10,000 – the equivalent of $28,655 (£22.3k) in today's money – hastily wrapped in toilet paper after she discovered the show's management had refused to give them Christmas bonuses.

According to Redditor Moge, who claims to have worked on the show during the 19th and 20th seasons, staff members earned premium LA wages despite the show being shot in Chicago and were handed cash bonuses to help see them through the off season. Oprah was "beyond nice" and an all-round excellent boss.

Oprah's former chief of staff, Libby Moore, told website Women's Agenda in 2017 that she hit the "job jackpot" working for the "Queen of All Media". She called the experience "extraordinary", with too many highlights to mention.

In 2009, for instance, Oprah wowed 1,700 of her Harpo production company staff and their families with a lavish trip to Barcelona, followed by a 10-day European cruise. The following year, her O Magazine employees each snagged a $10,000 ($14.4k/£11.2k today) bonus and iPad to mark the title's 10th anniversary. And in 2016, the generous billionaire treated her OWN TV network "dream team" to a fabulous Hawaiian holiday.

According to US celebrity website RadarOnline, Oprah has also been known to take her housekeepers on monthly designer shopping sprees to show her appreciation for their hard work.

Boss-wise, Mark Zuckerberg is "a perfectly nice guy on a personal level; it's just that professionally, he is focused on getting it done". That's according to a Quora post from Yishan Wong, who worked at Facebook in the noughties as a director of engineering before later becoming the CEO of Reddit. 

"[Zuckerberg is] a demanding CEO with a monomaniacal focus on making Facebook succeed in its mission," says Wong.

Instagram chief Adam Mosseri confirmed Zuck's demanding reputation in a recent episode of the podcast The Colin and Samir Show, emphasising that his "very results-focused" boss had "very high expectations".

Wong writes that he has yet to come across a "great" business leader who didn't have a significant body of ex-employees claiming they were autocratic or mean, summing up his former boss as "tough but fair".

Other testimonials are more glowing. Former Facebook engineering manager Tom Whitnah wrote on Quora that "it's hard to imagine a CEO being easier to work with", adding that Zuckerberg is "always open to people's ideas".

This is reflected in the tech whizz's Glassdoor CEO approval rating, which stands at a decent 69%, though the figure peaked at an outstanding 99% back in 2013. (Zuckerberg is shown here that same year.)

Sara Blakely has been described by her long-time personal assistant, Lisa Magazine, as "the girl next door, and yet one of the most creative geniuses I've ever met". The down-to-earth Spanx founder comes across as a brilliant, fun, and approachable boss who isn't afraid to admit her mistakes, and encourages her staff to do the same.

In 2018, Blakely revealed in a conversation with Stanford Graduate School of Business students that she chaired "oops meetings", where employees could own up to blunders in an accepting and judgement-free environment.

Blakely cut her teeth as a standup comic. As such, new Spanx employees are asked to perform a standup comedy routine as part of their training. Humour and light-heartedness are at the crux of Blakely's leadership style.

Rewarding her valued staff is also crucial to Blakely's approach.

The billionaire entrepreneur was dubbed the "world's best boss" in 2021 after private equity firm Blackstone bought a majority share in Spanx, which she originally started up in 1998 with just $5,000, or close to $10k (£8k) in 2025 money

Blackstone's purchase pushed the shapewear company's market value to a tidy $1.2 billion (£960m). Blakely celebrated the sale with a fabulous staff party and presented each of her very fortunate employees with two first-class plane tickets to a dream destination of their choice, along with $10,000 (£8k) spending money. 

Warren Buffett is a dream come true for execs who loathe overbearing helicopter bosses. According to a 2019 interview with CNBC, the leadership style of the Berkshire Hathaway CEO and his late business partner Charlie Munger can be best summarised as "to identify good managers and then get out the way".

In essence, Buffett hires the best and then lets them do their thing. Amiable and easy-going, the so-called "Oracle of Omaha" has only ever chosen to work with people he likes.

Incredibly, he and Munger never had an argument in all the years they worked together – and it's hard to imagine the mild-mannered Buffett ever losing it with his employees.

Robert Miles, author of The Warren Buffett CEO, hails the legendary investor as the world's greatest manager thanks to his laissez-faire approach.

As Fortune has noted, Buffett eschews the sort of frenetic, high-octane environment so beloved of other billionaire business icons and likes to keep his people happy.

And the proof is in the pudding: the Berkshire Hathaway boss has a Glassdoor CEO approval rating of 85%, which is considerably higher than Zuckerberg's 69% and Elon Musk's 59%.

Dubbed the other Iron Lady, Gina Rinehart certainly isn't to be messed with.

Highly litigious and controversial due to her many outspoken comments on climate change (among other issues), Australia's richest person is a formidable figure and you'd be forgiven for thinking it would be tough to work for her.

As it turns out, the Hancock Prospecting chief appears to be a good boss, though underlings have to toe the line. A former staff member who spoke to The Sydney Morning Herald in 2012 had this to say about the mining magnate: "She treats her employees well but you don't cross her".

Gina Rinehart is renowned for her philanthropy and this generosity extends to her thousands of staff.

In 2022, the UK newspaper MailOnline revealed she'd randomly selected 10 employees of Hancock subsidiary Roy Hill to each receive a $67,000 (£54k) bonus. One of the winners had started working for the firm only three months earlier.

To celebrate her 70th birthday last year, Rinehart reportedly donated 70 tax-free prizes of $67,000 (£54k) to staff raffles. "It really gets to the spirit of the way that she treats her employees," a company insider told MailOnline. "[She's] really trying to look after everyone, not just the very senior guys who are in the head office in Perth".

Richard Branson has been dubbed the "coolest boss ever" and it isn't hard to see why.

For starters, Virgin staff enjoy some phenomenal perks, including unlimited holiday and a free canteen at the firm's swish offices in London. Unlike many other business leaders, Branson positively encourages remote working to give his employees the flexibility they need to achieve a stellar work-life balance.

By all accounts, Branson is empathetic, approachable, and fun. According to former employee Suzanne Dribble, the laid-back billionaire would joke about in the games' room, party with staff, and "really knew how to let his hair down", "often [inviting] the team round to his lavish mansion in Holland Park".

As several other people who have worked with Branson have attested, the Virgin chief is a hands-off boss in a similar style to Warren Buffett.

The mega-entrepreneur trusts his staff implicitly and "the creative autonomy is incredible", says Alexis Dormandy, who sat on the Virgin board and set up both Virgin Mobile and Virgin Active.

To cap it all off, Branson is never negative with his team. "I think praise, not criticism is the most important thing for a good leader," he revealed in an interview with Entrepreneur in 2014. Needless to say, the tycoon's staff happily go the extra mile for their amenable boss and employee turnover is low.

In 2023, entertainment website The A.V. Club identified Beyoncé and Taylor Swift as two megastars who "actually treat the people beneath them really well".

The online newspaper shared a heart-warming anecdote from production designer Hannah Beachler, who worked on Queen Bey's 2016 visual album Lemonade and 2020 film Black Is King.

Beachler posted on X that when she started on Black Is King, she arrived at Bey's LA offices to find "a bunch of little plastic Emmy Awards", each with a hand-written name. She later found out that because Beyoncé's team didn't win for the 2019 Homecoming doc, the star stayed up after the ceremony and made everyone their own special award instead.

Perfectionist Beyoncé is even super nice when she's critiquing dancers that fail to live up to her high standards.

Glee and Crazy Rich Asians star Harry Shum Jr., who was a dancer on her first solo tour in 2004, said the megastar is "so sweet in the way she tells you you’re doing something wrong". Talking to CNBC in 2019, Shum Jr. also applauded the entertainer for the way she lifts up her staff and makes each person feel like a valued part of the performance.

Beyoncé is big on rewarding her employees. According to website The Richest, the record-breaking Grammy winner – who is said to pay her staff top dollar – hosts magnificent dinner parties for her team, also opting to shower them with massive bonuses and fancy gifts. In 2013, for example, Bey and her husband Jay-Z reportedly gave their employees $4.6 million in bonuses and gifts, the equivalent of $6.2 million (£5m) in today's money.

The 2023 firing and swift rehiring of OpenAI co-founder and CEO Sam Altman thrust the tech innovator's leadership style into the spotlight.

Former OpenAI board member Helen Toner later explained on The TED AI Show podcast that the decision to let Altman go was partly based on allegations from two execs, who claimed the AI supremo subjected them to "psychological abuse", creating a "toxic atmosphere". 

Yet the ousting of Altman prompted an astonishing "outpouring of love" from hundreds of OpenAI staff members.

This rush of support rapidly morphed into an all-out employee revolt. To protest Altman's firing, more than 700 of OpenAI's 770 employees threatened to quit and take up jobs with Microsoft instead.

It was their unwavering loyalty that resulted in the replacement of the board and Altman's reinstatement as CEO.

So what's Sam Altman really like to work with? Business Insider spoke to several former colleagues to find out. While he could appear "terse, impatient and superior" at times, Altman was described as an "extraordinarily approachable" boss who makes staff feel valued and listened to.

Bill Gates has no problem with admitting that he was an overbearing, demanding boss at Microsoft.

During a commencement speech at Northern Arizona University in 2023, the PC pioneer confessed that he was a hard taskmasker who was overly focused on results. "I didn’t believe in vacations. I didn’t believe in weekends. I didn’t believe the people I worked with should either", he told the graduating students.

Gates mellowed after fatherhood made him realise "there is more to life than work", he revealed to the graduates. These days, the Microsoft co-founder turned philanthropist advocates a healthy work-life balance.

Business Insider contributor Judy Bort has written about an "uplifting day" spent at the Bill and Melinda Gates Foundation in 2019.

According to Bort, employees always love having access to the Microsoft co-founder, who is heavily involved with the philanthropic organisation. Gates comes off as engaged and encouraging, with a good sense of humour.

Best of all, the Giving Pledge co-founder is great to have around if a tech problem occurs. He's not afraid to get his hands dirty and can fix any issue "without blinking an eye", according to Bort. "There's nothing like having one of the fathers of the PC industry in the room when tech support is needed".

Melinda French Gates was a manager at Microsoft when she married the big boss back in 1994. As per an article that appeared in The Seattle Times the following year, French Gates was "well-regarded" by her Microsoft colleagues.

The MBA grad started at Microsoft in 1987 and went on to work on a slew of lucrative multimedia products including Microsoft Cinemania, Publisher, Word, and Encarta.

A humble leader who prioritised her staff's needs, French Gates always insisted she didn't need special treatment and would stand in line at the Microsoft cafeteria, just like everyone else. She left the firm in 1996 to focus on her young family with Bill.

French Gates has since gone on to establish herself as one of the world's foremost philanthropists.

Judy Bort wrote that she was just as involved as her husband in the Bill and Melinda Gates Foundation, and it sounds as if she's equally encouraging and good-natured towards staff.

The couple continued to work together at the Foundation after their divorce in 2021. French Gates announced last year that she was resigning to focus her charitable efforts on women's rights and gender equality through her Pivotal Ventures organisation. 

When Nvidia boss Jensen Huang appeared on CBS's 60 Minutes last year, he was told how some of his staff had described him: "Demanding. Perfectionist. Not easy to work for."

Refreshingly, the AI chip king agreed, telling the interviewer that the words matched his approach perfectly.

Nonetheless, Huang is absolutely adored by the vast majority of his employees, in spite of his foibles. In 2023, he was rated America's most popular CEO (according to staff) in the inaugural Blind CEO approval rating index, while his Glassdoor CEO approval rating currently stands at an impressive 97%.

Staff enthuse over Nvidia's strong pro-employee culture and enviable perks. The company allows full-time remote work, offers unlimited holiday entitlement, and a wealth of other benefits. Moreover, employees with stock options have become fantastically rich as the company share price has skyrocketed.

Intriguingly, Business Insider reported that some of these more senior staff had stopped pulling their weight and were perceived by junior employees as being in "semi-retirement".

Nividia is famously resistant to letting go of staff, and it appears a minority may be taking advantage of Huang's benevolence. In fact, one employee even told Business Insider that "it's easier to get hired than fired" at the firm. 

Clearly not for the faint-hearted, working for the head of SpaceX, Tesla, and X Corp has been summarised as "ultra hardcore". Hours are long and remote working is strictly off-limits, with reports suggesting that Elon Musk is a tremendously demanding boss who pushes his staff to the limit.

Former SpaceX employee Jim Cantrell told Business Insider last year that while Musk can be difficult, he's also "very funny and charming... and full of big ideas". 

Carl Medlock, a former Tesla territory manager, has similarly described Musk as "fun" and "a really good guy". However, he's also highlighted the billionaire's hard-nosed approach, revealing that Musk has fired people on the spot for doubting his vision. And he isn't the only person who's claimed the CEO is a man of contrasts...

Ex-X exec Esther Crawford has called her experience of working for Musk "both amazing and terrible". Similarly, SpaceX president and COO Gwynne Shotwell revealed in a TED talk that working for the tech titan is both tough and inspiring, with Musk driving his employees to give their best performances. 

Exacting characters with sky-high standards aren't the easiest to work with, though they often get incredible results. "Diamonds are created under pressure and Elon Musk is a master diamond maker", says Dolly Singh, the former head of talent acquisition at SpaceX. "He knows you will exceed your own expectations if he keeps the heat on. It’s purposeful, and it’s brilliant."

Now discover the richest person in the world in every decade since the 1820s