Famous names who now make more than their famous former bosses

You’ve heard the spiel — a good education will lead to a good job, and when you get there, work hard, save hard, and make smart financial choices.

It’s touted as a well trodden path to wealth and success.

You’ve probably also heard cynics say that it’s more about who you know, not what you know.

Based on the wealth of some famous folk, who started out working as assistants to other rich and famous people, it turns out that the cynics might have been right, after all.

Topping the list of former assistants who are now worth as much as, or more than, their former bosses is former Microsoft CEO Steve Ballmer.
 

After dropping out of an MBA at Stanford to work as an assistant to Bill Gates in the 1980s, Ballmer was groomed by Gates and replaced him as CEO of Microsoft in 2000.

After moving on from that gig in 2014, Ballmer is now an investor who owns NBA team the LA Clippers, and has a net worth of US$139 billion (A$211 billion) – just shy of the fortune accumulated by his former boss.

Kim Kardashian takes the second spot on the list with a net worth of US$1.7 billion (A$2.6 billion), well ahead of former employers Paris Hilton and Serena Williams, who are both worth around US$300 million (A$456 million).

Kardashian worked as a stylist for her once more-famous friend Hilton in 2006, and also worked as a celebrity closet organiser in the early 2000s, where Williams was one of her clients.
 

Ye, formerly known as Kanye West and Kardashian’s ex-husband, holds the third spot on the list of ex-assistants who have attained wealth and fame similar to a former boss with an estimated net worth of US$1.8 billion (A$2.7 billion).

Prior to becoming one of the world’s best-selling music artists himself, West was a producer and worked in that capacity for Jay-Z – who has a net worth of US$2 billion (A$3 billion) – in 2001, before his own career as a recording artist took off.

Former child star, famous twin and fashion designer Mary-Kate Olsen ranks fourth on the list with a net worth of US$250 million (A$380 million).

Arguably, Olsen was already famous when – in 2005 as part of the requirements for her uni degree – she worked as an intern for celebrity photographer Annie Leibovitz, who herself has a net worth of US$50 million (A$76 million).
 

Actress Jennifer Garner takes the fifth spot on the list.

Before her acting career took off, she babysat for comedian and talk show host Stephen Colbert, looking after his daughter between auditions in the 1990s.

Now, Garner has an estimated net worth of US$80 million (A$122 million) compared to Colbert’s US$82 million (A$125 million).

Like her famous sister, Khloe Kardashian grew up with rich and famous friends and worked as an assistant to one of her besties, Nicole Richie, in the early 2000s.

“She just needed some help and I just needed a job,” Kardashian said on a podcast.

Kardashian’s net worth of US$60 million (A$91 million) today outstrips Richie’s US$40 million (A$61 million).
 

Even the Duchess of Sussex, Meghan Markle, had a job which saw her help celebrities before she came one herself.

Before Suits made her famous and her combined net wealth with Prince Harry clocked in at an estimated US$60 million (A$91 million), Markle made ends meet when she was on the audition circuit for acting roles by leveraging her neat handwriting skills and doing calligraphy work.

Among her clients was singer and The Masked Singer judge Robin Thicke, who’s worth an estimated US$10 million (A$16 million), with Markle writing the invitations to his 2005 wedding.