10 Tech Entrepreneurs Who Risked It All and Made It

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The Pandora founder once said if there was any piece of advice he’d offer his younger self, it’s to realize how hard life would be living in the regret of not following personal instincts. You would swear Westergren traveled back in time to send the message, especially when considering the tough financial road he crossed to make Pandora a $2.5 billion company. Out of money in the winter of 2001, only two decisions remained to keep the business alive: cut all loses or continue striving. Westergren not only went on to max out 11 credit cards, but also came up with the concept of deferring salaries, which led to over 50 employees doing so to the tune of almost id="mce_marker".5 million through the course of two years. Did you know such practices are illegal in California? One can only respect a boss for making such a critical attempt nonetheless. It wasn’t until 2004 when radio-streaming service was rescued via investment.

Believe it or not, there was actually a time when the richest man and most valued philanthropist in the world struggled to earn an honest buck. Despite his first business venture, Traf-O-Data—a device that read traffic tapes and processed the data—failing miserably due to its unreliable performance, that didn’t stop the software kingpin from moving ahead with his grand vision. Already taking a huge chance by dropping out of college to pursue his dream, Gates set off his personal computer initiative by applying some of his experiences from Traf-O-Data, while borrowing concepts from other tech companies and innovators to create one of Microsoft’s earlier products. Knowing the legal circumstances that stood to come from these moves, Gates felt the payoff would take care of the legalities and history was written from then on.

Times must have been hard if McDonald’s was rejecting him for a job interview. Still, Chahal didn’t let the fast-food chain stop his grind to greatness. Noticing how huge the online advertising market was becoming after DoubleClick went public, the then-16-year-old made a huge sacrifice by dropping out of high school and running his first-ever company, Click Agents, fulltime from his bedroom. Two years later, he sold it for $40 million, and then created a second company, BlueLithium, that sold to Yahoo for $300 million by the age of 25. Those ventures led to the creation of the advertisement platform known as RadiumOne.

Growing up as a child who performed terribly at school and on standardized tests, the English business magnate utilized his powerful personality as a driving force to establish the Virgin Group dynasty. Going on to establish a number of technological companies under the Virgin umbrella, it was Virgin Airlines that was in the midst of a financial disaster in the early ’90s, forcing the owner to use the id="mce_marker" billion previously earned from selling Virgin Music Group to Thorn-EMI to keep his airline up and running. Placing all chips on the table once again, he entered the railway business with Virgin Trains even after analysts viewed it as his riskiest business exploit yet. The return of investment obviously turned out to be huge and did little to effect his regime. Hey, for a man that’s been able to beat 125 lawsuits for every imaginable thing possible, it’s easy to see why he’s viewed as the biggest venture capitalist daredevil of our time.

Looking to change the online shopping landscape in the early ’90s—Bezos sacrificed his financial security and left a job as the VP of hedge fund D.E. Shaw, moving out to Seattle with his wife and building Amazon.com out of a garage. Continuing to push all financial risks to the limit, he nearly brought the company and himself to the brink of bankruptcy, though the compromise served beneficial and helped the website generate a few million from investors. But after gaining monetary backing, the company struggled to turn a profit for nearly seven years, causing the CEO to execute some other risky moves, finally earning a surplus in 2001 that’s set to reach an estimated id="mce_marker"00 billion sometime this year.

A home cleaning entrepreneur who went on to become filthy rich: Does anyone not see the irony there? The billionaire vacuum engineer apparently spent six years trying to create the perfect cleaning system. In fact, his obsession to achieve this led to over 5,000 built prototypes and a $4 million debt that required him to take out close to three mortgages on his house. It was when selling his first product that Dyson was able to repay the bank in a matter of months. Learning the patent game from scratch, he started using the licensing fees from the invention to expand his commercial empire.

Always one to outdo his previous milestones, the founder of PayPal and Tesla Motors set his sights on space exploration and created SpaceX—a company with the goal of reducing space transportation costs and facilitating the colonization of Mars. With no experience in the aerospace industry, he spent most of the capital earned from the sale of PayPal to get the project off the ground. Between that and funding his profit-less auto company, Musk was gambling his entire fortune between two unsuccessful businesses. Yet it was through these imperils where SpaceX was able to win a id="mce_marker".6 billion contract from NASA and extend its push into outer space.

Tech’s billionaire playboy was once labeled a “seemingly aimless young man” who would never amount to much after dropping out of high school when his mother passed. Ouch. Persevering through the emotional torment, Ellison stepped up his aptitude in math and science to become a skilled programmer and technician. Intent on creating the world’s first commercially viable relational database, he formed Oracle and promised customers unavailable features, only to come back and demand his developers to create such products. Granted he understood the benefits of first-mover advantages, the decision pushed the company into a serious cash-flow crisis. But in maintaining his narcissistic ways, speeding through four marriages, and risking everything else to own a large amount of Oracle’s stock rather than sell it to venture capitalists, Ellison somehow turned it all around to become one of the wealthiest figures in the world.

Whether it was being expelled from a university or dealing with his father’s suicide, which forced him to take over the family business at the age of 24, Ted Turner was plagued with bad luck early in life. As you can see, Karma rewarded him for those sacrifices and transformed him into a multimedia goliath. Upon taking over his dad’s outdoor advertising firm, Turner turned over a profit and went on to purchase a near-bankrupt Atlanta TV station. From there he caught wind of RCA’s satellite broadcasting technology and invested in it, leading to the country’s first “superstation” in WTBS. Later on, he saw the potential in creating a 24/7 news station and took the biggest gamble of his life, putting his entire fortune up to create CNN, another move that certainly paid off.

No family inheritance, trust fund, or VC to tap into—Steve Jobs looked beyond all financial roadblocks to seek out his ultimate vision of having a computer “in the hands of everyday people.” His teen years were spent sleeping in friends’ dorm rooms, recycling Coke bottles for cash, and snatching free meals wherever he could get them. Jobs then went on to build what would become one of the biggest tech companies ever, Apple Inc., right in his parents’ garage. From the company’s beginnings to saving it from bankruptcy after being fired, the serial technology entrepreneur committed every second of his life, feeding off adrenaline and stress to design groundbreaking products that would forever shift the consumer market. Sadly, it was these high-pressured tensions that contributed to his illness and untimely death, which leaves us forever indebted to him. Pay homage!