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Some Of The Riskiest Entrepreneurial Gambles Of All Time

roulette-infogrphic-top Some Of The Riskiest Entrepreneurial Gambles Of All TimeInfographic Looks At Some of The Riskiest Gambles In Business Of All Time


When you decide to launch a startup or dive into entrepreneurship there is a lot of risk, and hopefully a lot of reward. For many, it’s gambling. There are so many stories of entrepreneurs taking tremendous risks to further their  companies, their ideas and technologies.

The risks and rewards, the gambles, of starting a business often reach well beyond the founders of the company. Early stage investors make bets every day on different companies. Seed stage investing is often seen as the riskiest of all, that’s why in many cases, seed stage investors give up the least amount of money for the most amount of equity. Many of Uber’s earliest investors stand to make a huge profit on believing in the ride sharing startup before they had their first customer.

The folks at have created an infographic chronicling the 10 riskiest business gambles of all time. The infographic takes a look at the five biggest losses and the five biggest wins both for investors and founders.

There are so many times when starting up a business has been compared to gambling. One of the most notable tales is a true story about Las Vegas gambling. Fred Smith, the founder of FedEx once went to Las Vegas to gamble his last $5,000 at Blackjack to cover the fledging companies expenses and make payroll. Luckily for the company, and Smith’s employees, that gamble paid off.

The gambles in the infographic below are the biggest of all time. These things don’t happen everyday. Many of these stories we all know already, like the story of Roy Wayne the early investor in Apple who sold his equity stake back to Steve Jobs and Steve Wozniak for $800. That stake today would have been worth $833.82 billion dollars (with a B).

On the win side are Larry Page and Sergey Brin the founders of Google who almost sold the company for $1 million dollars. Today it has a market value of nearly $650 billion dollars.

Check out the entire infographic below and here at 


risky-gamble-business-infographic Some Of The Riskiest Entrepreneurial Gambles Of All Time


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