Jason Shapiro Should've Been a Lawyer

As a Trader with zero to negative correlation to traditional assets, managing money on behalf of institutional investors is exactly where Jason Shapiro is supposed to be.

But if you were to ask him, he’d tell you he probably should’ve been a lawyer. And anyone else who comes to him asking about how to break into the world of full-time trading will likely get admonished with: “Go to Law School instead. Become a lawyer, then trade on the side with the money you make.”

Why would a highly successful trader say this?

Because Jason agrees with us that trading is easy, but BEING a trader is damn hard.

Jason is a contrarian trader. In its most basic form, this means Jason is seeking out opportunities where the crowd may have overextended itself in one direction. If everyone is on the same side of the trade, the reversal can be nasty when they all head for the exits at the same time. Being the trader on the right side of this reversal can be immensely profitable when Jason gets it right. But it’s very, very difficult.

Among the many things that make trading hard is that you are often doubting yourself. Especially if you aim to make money when almost everyone else is wrong. 

“If the market made sense, it would be simple,” he says. “I could hand you a system that consistently makes money, and you’d STILL mess it up.” It’s all psychology.

Jason gets charged up when people think they can easily learn to become successful traders. “Most amateur speculators are delusional.” He recoils when he hears people talking about the “freedom” that trading can provide. “Trading isn’t what people think it is. This isn’t the freedom you think it is.”

And very few can handle the reality of lumpy return streams, even if the “average” annual gain is a very impressive number. “It fucks with your head!”

In reality, Jason believes most retail people who engage in the markets are hobbyists. And there’s nothing wrong with that, “just know that’s what you’re doing!”

In this episode of Off The Charts, Jason shares some tactics he’s devised to keep him in the game for as long as he has been (hint: frugal living), why he’s no longer invited to dinner parties (hint: people cry), and he breaks down precisely why it never works out if one attempts to copy another trader (hint: math).