Cracked.com has become a favorite website here at the office. Their standout feature is obscure, snarky and absolutely fascinating lists: “The 6 Most Aggressively Ridiculous Benders in Modern History” and “7 Mind-Blowing Easter Eggs Hidden in Famous Works of Art” are two recent examples, along with “6 Global Corporations Started by Their Founder’s Shitty Luck.” Nintendo’s story proved particularly interesting – to gamers and non-gamers alike.

Nintendo started as a small playing card manufacturer in 1889. They eventually branched off into, among other things, “love hotels,” but continued to profit mainly from the cards. As time hurtled recklessly forward, playing cards became a plebian pastime in Japan. Déclassé, if you will. The company was on the verge of collapse.

Through the ingenuity/laziness of a production employee tinkering around with various parts lying about, he made a robotic arm gadget that the president went crazy for. Maybe he was too short to reach high shelves. Soon Nintendo was producing the arms, and other weird electronic toys and gizmos followed, including a love/lie detector, which looks like a technological version of a Cosmo quiz.

In vague homage to the Love Tester and the hotels, Nintendo has come full circle with Wii remote vibrators. Though not made by Nintendo, they could enhance one’s Wii-playing experience exponentially. At least they had to give up the rights to modify their products, right? Despite their major contribution to the degeneration of contemporary society (for the overweight, sunlight-starved children hiding in their basements and having gaming-related seizures), Nintendo’s genius, innovation and history cannot be denied.

So did Nintendo take a risk? Arguably they did; switching from playing cards to electronics couldn’t have been particularly easy, cheap or predictable. They kept the business rooted in the entertainment market, but hopped on the “wave of the future,” which could have bombed if not done right. Other companies addressed in the cracked.com article include LEGO and Sharp, who essentially share Nintendo’s story: something catastrophic happened to make their original products impossible to sell, so they jumped into a new market. LEGO went from real houses to plastic blocks; Sharp began with pencils (hence the name “sharp”) before making the switch to radios.

Recently Malcolm Gladwell published an article in the New Yorker called “The Sure Thing” (unfortunately, the full text version is not available online without a subscription). He examines Ted Turner’s strong-armed rise to entrepreneurial stardom and hedge fund manager John Paulson’s predatory manipulation of the housing bubble. Gladwell debunks the myth of pioneering entrepreneurs as extreme risk takers. He states that Turner’s acquisitions were mostly purchased with stock options; therefore he spent virtually none of his own money founding CNN and resurrecting the Atlanta Braves, among other lucrative ventures. Paulson, who made billions by purchasing mortgage-backed securities before the housing crisis erupted, was deemed crazy for buying these apparently worthless mortgage bundles, essentially betting against homeowners that they would default on their mortgages. He wasn’t taking a risk – he spent a lot of money on research and learned that not only were we in the midst of an enormous housing bubble, its burst was imminent. He had knowledge that no one else had before he did anything that could be perceived as “risky.”

How much risk are you, the entrepreneur, willing to take? Gladwell cites a study where, given three profit models (high-risk with high profits, moderate with moderate profits and low-risk with low profits), successful entrepreneurs overwhelmingly selected the low-risk option. We see from Nintendo, LEGO and Sharp’s examples that putting your financial neck on the line can produce highly profitable outcomes. However, these were all established companies going through tough times that were forced to embrace change or fold. How many other companies in the same situation did fold, never to have their story broadcast on the internet?

Turner and Paulson came from a place of success – Turner’s inherited billboard business made his subsequent acquisitions possible, and Paulson certainly wasn’t hurting as a Wall Street trader. All of this, really, boils down to something we all know: the more money you have, the easier it is to make more, provided you have the business intuition to do so. When it all goes downhill, you have to take major financial risks in order to salvage your business. When you have all the money in the world, you throw stock options around to earn more capital gains. So although Gladwell accurately pins Turner and Paulson as cautious investors, Nintendo’s story (ironically) follows the uniquely American notion that big risk takers, with the right insight into the right market, score big rewards.