The Myth of the Self-Made Entrepreneur

Photo by Joe on Unsplash

Everyone loves an entrepreneur success story. It’s especially compelling if it has a rags to riches narrative, like starting a company out of your parents’ garage, or investing your last $300 on inventory and surviving off of ramen for a year.

After working for a number of entrepreneurs, I’ve realized that more often than not there is a hint of embellishment involved in crafting the most persuasive success stories. Especially if they claim to be self made.

There’s nothing wrong with a little white lie, but it can make budding entrepreneurs feel bad if they’re comparing their behind-the-scenes with someone’s highlight reel. The reality is, no matter how talented or hard working an entrepreneurs is, everyone needs help eventually. But admitting that you had wealthy parents or industry connections doesn’t make for a very glamorous story, so some entrepreneurs (and media outlets) prefer to downplay the advantages they’ve had on their path to success.

Below are six stories of famous entrepreneurs that will make you question how self made they really are.

1. Elon Musk

Photo courtesy of CEO Magazine

Elon Musk is, without a doubt, an incredibly talented businessman and visionary thinker.

His childhood and upbringing, however, is somewhat of a mystery. Several sources point to the fact that Musk’s family had significant money, however the exact numbers and origins are unclear. There is a rumor, for instance, that Musk’s father Errol owned part of a South African emerald mine that allowed the family to profit during the Apartheid.

In an interview with the Daily Mail, Errol spoke about the upbringing of his children:

I drove them to school in a convertible Rolls-Royce Corniche, they had thoroughbred horses to ride and motorbikes at the age of 14. They were spoilt, I suppose.

A wealthy engineer and property developer, Errol was a millionaire before the age of 30. According to Inside Hook, the Musks were well off financially, owning “one of the biggest houses in Pretoria thanks to the success of Errol’s engineering business.”

Aside from his family wealth, several of Musk’s companies have benefited from billions of dollars in government assistance. The Los Angeles Times found that Tesla and SpaceX received nearly $5 billion in government aid over the years.

2. Warren Buffet

Photo courtesy of Stock Basket

The man, the myth, the legend — Warren Buffett — will undoubtedly go down in history as one of the greatest investors of all time.

Yet from his earliest days of investing, Buffett wasn’t on a level playing field to the rest of the world. As the son of an investor-turned-congressman, Buffett’s father was able to give him a great head start in his career.

In fact, some of Buffett’s first investors were people he met through his father’s government and business connections. In the 1950s, a few prominent families gave Buffet $10,000 towards his first investment fund, which at the time was very generous money.

As a result of his father’s ties with the government, it is also speculated that Buffett had access to insider information. Prior to 2012, the only people who were allowed to trade on insider information without having criminal charges brought against them were congressmen.

These days, Buffett is a household name and investment legend, with access to the kind of information average investors read about weeks later in the newspapers.

3. Jeff Bezos

Photo courtesy of Forbes

Compared to the e-commerce behemoth it is today, Amazon started out as a humble online bookshop in the 90s. However, what’s not so humble is the $300k investment Jeff Bezos received from his parents to get his business off the ground.

The initial investments didn’t stop there. Bezos raised even more capital from friends and family by offering them one percent of Amazon in exchange for a $50,000 investment.

To give credit where credit is due, it’s incredible that Bezos was able to turn hundreds of thousands of dollars into billions.

However, this didn’t happen without a little help in the form of government subsidies. A recent Good Jobs First report uncovered that Amazon has received over $3.7 billion in taxpayer subsidies. All this despite the fact that Bezos’s net worth has been boosted by almost 80% (or $90 billion) over the course of the pandemic.

4. Kylie Jenner

Photo courtesy of Forbes

The Kardashian-Jenner family is no stranger to controversy, so when Forbes published a story in 2019 claiming that Kylie Jenner was on track to become the world’s youngest self-made billionaire (a claim that has since been retracted), the internet broke out in disarray.

How did the youngest member of the Kardashian clan end up on a Forbes list in the first place?

According to Jenner, she used $250,000 of her own savings from modeling and Keeping Up With The Kardashians appearances to fund a sell-out makeup line. With her power as a social media influencer, she expanded the Kylie Cosmetics brand to a multi-million dollar company.

However, it would be remiss to believe that 18-year-old Jenner got there all on her own. In fact, it was through her family’s connections that she was able to earn the initial £250,000 investment in the first place. Additionally, her family’s influence and marketing genius is what guaranteed the brand would become an instant success.

5. Bill Gates

Photo courtesy of Times

Money certainly wasn’t an issue for the Gates family while Bill was growing up. His parents both had successful careers and were extremely socially connected in Seattle.

Gates’s mother, Mary Gates, was instrumental to her son’s success. A prominent businesswoman, she served on the boards of various major corporations. It was through her connections with other board directors that she helped Microsoft land a lucrative contract with IBM while the company was still in its infancy.

By taking advantage of his parents’ connections and wealth, Gates went on to build one of the most influential companies in the world.

6. Donald Trump

Photo by Alex Brandon on AP

Finally, we have Donald Trump, who once famously claimed that his father gave him “a small loan of a million dollars” to start his property development business.

Despite how much Trump would like everyone to believe he is completely self-made, just like the other entrepreneurs on this list, his upbringing tells a different story.

Growing up in a wealthy suburb, Trump was groomed from a young age to follow in his father’s footsteps as a real estate developer. In 2018, The New York Times reported that Trump borrowed at least $60 million from his father, largely failed to reimburse him, and had received $413 million (adjusted for inflation) from his father’s business empire over his lifetime.

It goes without saying that these entrepreneurs all worked hard to get to where they are. But it’s anyones guess whether they would be household names they are today without a little help from family connections, savvy PR teams or the media.

Dame Magazine summarized it perfectly when describing this myth of the self made entrepreneur:

When [entrepreneurs] downplay their advantages — and the media follows suit — it prevents us from dealing with the truth about income inequality, opportunity access, and classism.

It’s always easier to make money when you already have a lot of money. So the next time you catch yourself comparing your career to a famous entrepreneur’s, remember that they likely had a lot of help along the way.



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Daniela Singlel

Daniela Singlel

Confused millennial. Unwilling participant in the attention economy. Equal parts classy & sassy. Sometimes I write about the new media & pop culture.