5 miilionaires-SG

Striking it rich isn’t what it used to be. Before there was technology capable of providing us with instant access to the world’s information, entrepreneurs lived a much riskier existence, relying solely on luck and gut instinct. Modern self-made millionaires are mostly made by design rather than relying on fate to intervene. Today, career moves are meticulously calculated, with safety nets never out of sight.

For those averse to taking risk, ‘living dangerously’ may come in the form of a wild night out or playing online slots, but for those who are still willing to take big risks, the potential for big rewards still exist. In this article we’ll delve into the lives of 5 entrepreneurs who risked it all and became massively rich because of it.


Do entrepreneurship and risk go hand in hand?

Not knowing what might lurk around the next corner can be terrifying, especially when there are millions or even billions at stake. The very nature of starting a new business venture requires a certain level of risk. It doesn’t matter how meticulous a business plan is, there is always the potential for catastrophic failure. But with great risk, comes great potential. These five wealthy risk-takers prove that to be true.


5 Millionaires Who Risked It All

Sylvester Stallone

When you think of famous risk-takers, Sly Stallone probably isn’t the first name that comes to mind, but that’s only because many people don’t know the story of his early career. In the mid-70s, Stallone was a struggling actor who had no choice but to accept any role he could get. In 1975, he walked into the offices of United Artists and pitched them the idea for a little film about a down-and-out boxer named “Rocky.”

United Artists offered Stallone $4 million for the script, but with one stipulation – Stallone would not be able to star in the film. Instead of accepting the easy cash, Stallone forego the upfront money all together, instead opting to star in the lead role. The following year, Rocky won the Academy Award for Best Picture, forever cementing Stallone as one of the most successful risk-takers in Hollywood history.

J.K. Rowling

J.K. Rowling is the richest author in the world. Her Harry Potter series has evolved into a media empire, spawning movies, a play, tons of merchandise and even a theme park, but she wasn’t born a success story. Rowling comes from a very modest background. Neither of her parents received a college education.

From a very young age, Rowling knew she wanted to be a novelist, but she was always told that writing would never pay the bills. Shortly after becoming a single parent at the age of 22, the author found herself out of work and relying on government assistance to support her daughter. While receiving benefits, Rowling hunkered down in coffee shops, typing away at her first Harry Potter novel. After receiving a dozen rejection letters, a small publisher offered her a contract. The rest is history.

Bill Gates

Bill Gates is the most successful college dropout in history. In 1975, Gates enrolled in the prestigious Harvard University. While attending the Ivy League school, the future richest man in the world spent most of his time tinkering around with the school’s computers. Two years into his schooling, Bill Gates decided to take a huge risk; a risk which would become one of the most consequential decisions of the 20th century.

In 1977, Gates decided to drop out of Harvard to start a small software company with his childhood friend, Paul Allen. In 1981, Microsoft went public, leaving the 26-year-old Gates an instant millionaire. At the age of 31, Bill’s shares in the company surpassed $1 billion. In 1995, less than two decades after dropping out of Harvard, Gates was crowned the richest man in the world.

Elon Musk

As a co-founder of PayPal, Elon Musk was already a multi-millionaire when he decided in 2002 that he wanted to start a company that would make space travel more affordable and would enable people to eventually colonize Mars.

Before launching SpaceX, Musk had no previous experience with design or aerospace, but he was focused on making his vision become a reality. In 2006, he invested over $100 million in SpaceX, a huge risk for a man who had never ventured beyond his entrepreneurial comfort zone. The risk turned out to be a massive success. In 2008, SpaceX secured a $1.8 billion contract with NASA to resupply the International Space Station.

Mark Pincus

In the early-2010s, Zynga was the hottest name in gaming. As creators of massively successful social games, such as Farmville and Mafia Wars, Zynga ruled the casual gaming roost. Though massive success did not come without great risk.

In 1996, Zynga Founder and CEO Mark Pincus’s first company, Freeloader, was on the brink of bankruptcy. With only a month of cash left, an investor offered funding, under the condition that Pincus would hire the CEO of his choice. Mark declined the offer, instead opting to remain independent. A few months later, Pincus obtained funding on his terms, and later sold the company for a hefty return.


To Sum Up

What do all five of these wealthy people have in common? They all made high risk decisions that resulted in massive rewards. Whether it was walking away from millions of dollars, or deciding that the easy path wasn’t the path for them, each and every one of these millionaires and billionaires understood that making a gamble would be the key to their success.

As real estate developer Trammell Crow once said: “Everything in life is a risk. If it’s without risk, it’s probably without profit.” These entrepreneurs prove that to win big, you’ve got to play big. Are you ready to take the risk?

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