The Strange First Jobs Of Super Successful People

The Strange First Jobs Of Super Successful People

Currently more than 44 million Americans have a secondary source of income, colloquially known as a “side hustle.” The rising cost of living and the ease of entering the sharing economy, via platforms such as Lyft and AirBnB, have all contributed to the enormous rate of people seeking secondary employment.

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The motivation of starting a side hustle isn’t limited to just covering the bills — more and more millennials have their focus set on starting their own businesses. Over 62% of millennials have considered starting their own business, and a further 72% have stated that they believe startups and entrepreneurs are a “necessary force” to spike economic growth and job creation.

In the past decade, entrepreneurs have become their own kind of celebrity. Elon Musk and Mark Zuckerberg are practically household names, and the rise of mega corporations that started in a garage (see Google) have only fuelled a collective desire in millennials and Gen-Z to be their own boss, and start their own businesses.

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While technology has enabled more entrepreneurial spirits to enter the secondary workforce, holding down a second, not-so-glamorous job isn’t new among successful business pioneers.

While some of today’s business magnates began their careers with a trust fund and an Ivy League education, others still had to climb the dirty first rungs of the career ladder the old fashioned way. With grit and perseverance.

Mark Cuban, Elon Musk, Jeff Bezos, Richard Branson, and Reed Hastings have a few things in common. They’re all successful, they’re all CEO’s, and they’ve all had to work less-than-glamorous jobs to get where they are today.

The following infographic, courtesy of Fundera, highlights some of today’s most successful people — and the strange and unusual jobs they had before they became titans of industry.

weird first jobs of successful people

The Strange First Jobs Of Super Successful People Infographic (Text Version)

Elon Musk

"You have to put on this hazmat suit and then shimmy through this little tunnel that you can barely fit in. If you stay in there for more than thirty minutes, you get too hot and die."

Founder of Tesla and SpaceX

Net Worth: $21 Billion

Former Job: Janitor of a boiler room at a lumber mill


I was sacked from Dunkin' Donuts for squirting the donut jelly all over the customers.”

Pop star

Net Worth: $800 Million

Former Job: Cashier at Dunkin’ Donuts

Tom Brady

Being out on the practice field never feels like work to me, but that definitely felt like work when you’re cleaning up industrial parks and scrubbing the tops of roofs.”

NFL Quarterback

Net Worth: $180 Million

Former Job: Construction worker

Reed Hastings

I loved it, strange as that might sound. You get to meet a lot of different people.”

CEO of Netflix

Net Worth: $2.3 Billion

Former Job: Vacuum cleaner salesman

Marissa Mayer

I learned that speed mattered -- the only way to be eligible to work an Express Lane was to do 40 items per minute consistently over an 8-hour shift.”

CEO of Yahoo

Net Worth: $540 million

Former Job: Checkout Clerk

Mark Cuban

I would go door-to-door: "Hi, does your family use garbage bags?" And who could say no? So that's where I learned to sell."


Net Worth: $3.3 billion

Former Job: Door-to-door garbage bag salesman

Richard Branson

With my best friend as my partner, we set about breeding budgerigars. We saw a gap in the market to sell budgies as they were very popular with kids in school at the time.”

Founder of Virgin

Net Worth: $4.8 billion

Former Job: Budgie breeder

Jeff Bezos

You learn a lot as a teenager working at McDonald's. It's different from what you learn in school. Don't underestimate the value of that!”

Founder of

Net Worth: $34.7 billion

Former Job: McDonald’s cashier

Michael Dell

"The best part was the wisdom of the restaurant owner. He took great pride in his work and cared about every customer who came through his door."

Founder of Dell

Net Worth: $18.2 billion

Former Job: Dishwasher at a Chinese restaurant

Taylor Swift

I forgot to check one time and they hatched all over these people’s house. There were thousands of them. The people had little kids, and they couldn’t kill them because that’d be a bad Christmas.”

Pop star

Net Worth: $280 million

Former Job: Knocking praying mantises out of Christmas trees at a farm. With a broom.

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