The top 10 most iconic business gambles

In business, it’s sometimes necessary to take a gamble. For some entrepreneurs these gambles can be the key to success, but for others one decision can cost them billions.

Sometimes in business you have to take a gamble in the hope that the venture will prove to be worth it in the reward, but what if it isn’t? has researched five of the riskiest business gambles that won big and five that lost billions.

For entrepreneurs seeking success, big decisions are all part of the game. However, it’s hard to know when one of these choices will be their ticket to triumph or when it will be the mistake that costs them billions. For some of the entrepreneurs in our list, knowing when to persevere and when to jump ship has been the difference between failure and success.

From Zuckerberg to Page, these entrepreneurs have faced many crossroads in business within their career.’s research delves into the entrepreneurs that chose the path to success and those that made an expensive wrong turn.

The winners

Mark Zuckerberg, Facebook Following the initial success of his social media platform, Facebook, Zuckerberg was offered $10 million for the site by social gaming site Friendster just 5 months after beginning operations. However, Zuckerberg saw the potential in his site and turned down the offer. Today, he has made a personal gain of $68.325 billion.

Howard Schultz, Starbucks – Howard Shultz was an employee of the original Starbucks, before the chain became what it is today. After visiting Milan he was inspired by the idea of having coffee shops on every corner and decided to make a move on his own. After raising $400,000 for his first shop, he eventually made the move to buy the name rights from his previous employer and also the retail unit. Today, Starbucks is worth $85.6 billion.

Larry Page & Sergey Brin, Google – It’s hard to believe that the founders of one of the world’s largest technology companies would ever have lost faith in their business, however in 1999 Larry Page and Sergey Brin did just that. The entrepreneurs attempted to sell their company for $1 million, however Excite CEO George Bell refused the offer. This rejection was a blessing in disguise for the duo, with the company now being worth over $397 billion.

The losers

Roy Wayne, Apple – A co-founder of Apple, Ron Wayne felt out of his depth alongside Steve Jobs and Steve Wozniak and left the company after just 12 days selling his shares for just $800. Despite being invited back multiple times he pursued his passion for slot machines instead, losing out on over $34 billion.

John Antioco, Blockbuster – Popular movie rental service blockbuster was offered the opportunity to purchase small DVD-by-mail service Netflix for $50 Million, however CEO John Antioco turned down the opportunity calling it a “small, niche business”. In 2010, Blockbuster filed for bankruptcy however today Netflix is worth $61.6 billion.

Jerry Yang, Yahoo – Believing in his business, Jerry Yang refused to sell Yahoo to Microsoft for $44.6 billion believing the offer was too low. However, eight years later he was forced to sell his failing company for a fraction of the price at $4.6 billion, losing out on $39.8 billion from the initial offer.


As the infographic below illustrates, in business, risks are inevitable. Making the right decision at the right time can be the difference between massive success and catastrophic failure. For some of those detailed in the graphic these gambles more than paid off, while for others their decisions were not only a learning curve but also the most expensive decision they ever made.

Owen Gough

Owen Gough

Owen Gough is a reporter for He has a background in small business marketing strategies and is responsible for writing content on subjects ranging from small business finance to technology...

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