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Jul 16, 2021

The Seduction of Risk

By:Dylan Ratigan

Quintin Dailey. Ever heard of him? Most people outside of Chicago never have. He was the starting shooting guard for the Chicago Bulls before Michael Jordan was drafted (and the only reason anyone in Chicago remembers him is because during one game he had someone go buy him a couple hot dogs which he then ate while sitting on the bench). For every Michael Jordan there are thousands of Quintin Dailey’s, guys who tried but didn’t quite break through.

There are a few names we all know. Bezos, Musk, Zuckerberg, Brady. They’re the breakout stars, the outliers. Outliers are just that, outliers. By definition there are only a few of them; however, their influence over the rest of us is disproportionate. They provide inspiration. They offer hope. They embody the American dream that if you just work hard enough and take some risk, success can be yours, too. It’s a seductive idea and arguably a necessary one in order for capitalism to thrive. But not everyone will succeed. In fact, more will fail than flourish.

There are countless books and movies written about breakout stars. We put them on a podium as examples of triumphant risk-takers. We parade them in the media as proof that success can be had if you’re willing to take a chance. There are songs written about these stars like, I Wanna Be Like Mike, a tribute to Michael Jordan. However, no one writes songs about the men and women who devoted their lives to becoming professional basketball players, putting their sport above all else, only to not make it. There are no books about the Elon Busts or Jeff Bankrupts of the world.

When Richard Branson launched into space a week ago, the world cheered. Forget about the fact we’ve been doing this for sixty years. The message was clear, if you want it bad enough, even the sky isn’t the limit. 

I have nothing but admiration for guys like Bezos who embraced risk to start a business from literally nothing. Steve Jobs and Steve Wozniak started Apple from scratch. There truly are some amazing success stories in this country and tremendous amounts of wealth have been generated in the United States because of capitalism-induced risk and our entrepreneurial spirit. 

However, not everyone was born to be an outlier. Not everyone is a good risk taker. While we celebrate the success of Branson’s flight, let’s not forget it was just a year and a half ago that Mike Hughes took a similar risk and died in the process. 

Most venture capitalists will tell you having one out of every fifty investments make money is very good. 90% of new businesses fail within the first three years. That’s just the nature of the beast. The idea of, “if it worked for them, i can do it, too” has led more people to bankruptcy than billions. 

It’s not that I oppose risk. I encourage it. But I encourage smart, methodical risk. Go for the game winning shot. Invest in a startup. Just make sure your parachute will deploy before launching yourself.

Be sure to catch Dylan Ratigan & Tom Sosnoff every Wednesday at 1pm CT for a new episode of Truth or Skepticism live on

Listen to previous episodes on Spotify, Apple Podcasts or on

Options involve risk and are not suitable for all investors. Please read Characteristics and Risks of Standardized Options before deciding to invest in options.

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