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High-risk business gambles taken by ten notable entrepreneurs

Kenny Rogers once sang about the advice he gleaned from a poker player: "You've got to know when to hold 'em, know when to fold 'em and when to walk away." Those words ring true of entrepreneurs making business gambles as well.
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The title of entrepreneur is often linked with that of risk-taker. In fact, an article from the Frugal Entrepreneur goes so far as to question whether the ability to make business gambles could be compared with the skills used by hardened poker and roulette players.

Much like gamblers, entrepreneurs place bets on “attractive opportunities”. But as black jack movie 21 highlights, there’s more to striking gold than just luck. There’s a strategy.

“Despite popular belief,” the article explained, “entrepreneurs are never as daring or as impulsive as they’ve come to be seen. Truthfully, the data backing up an entrepreneur’s quest and reason to pursue his or her mission is usually left unnoticed by the vast majority of analysts who claim them to be gamblers.

“Working on impulse can be possible without being labelled a gambler at large. Impulse creates momentum, but entrepreneurs take this impulsivity with a grain of salt and choose to act on what simply makes sense. Furthermore, entrepreneurs are all made and very few, if any, are born this way. What really makes an entrepreneur is their ability to make mistakes, learn from these mistakes and build better strategies moving forward.

“This trial and error mentality is often lacking in a gambler’s state of mind. Entrepreneurs always know when to play the game, so that they might win, due to their past actions and decisions.”

That doesn’t mean calculated business gambles always ends in success though – it can lead to excruciating losses.

Facebook founder Mark Zuckerberg, for example, turned down a $10m offer by Friendster to buy the platform mere months after its launch. Today, Zuckerberg has made a personal gain of $68.325bn. On the other hand, John Antioco, previously the CEO of Blockbuster, rejected the chance to buy Netflix for $50m. Blockbuster went bankrupt and Netflix is now worth $61.6bn.

RouletteOnline.net, intrigued by the concept, took a look at ten of the biggest business gambles – and whether they led to success. Zuckerberg and Antioco, of course, make that list, joined by former Starbucks CEO Howard Schultz, Apple co-founder Roy Wayne and Yahoo! co-founder Jerry Yang.

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About Author

Shané Schutte

Shané Schutte is the deputy editor of Real Business, with a particular specialism in employment and business law, human resources, information technology and sales/marketing.

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