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’ll 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 f-s 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).
The audio version of this podcast can also be found on Apple Podcasts, or wherever else you stream your favorite podcasts!
We talk to a lot of traders. Not just on this podcast, but across everything we do. And one thing that is common to most of them is some level of stress which must be routinely navigated. And it’s often a real struggle. Many of them are emotionally damaged and scarred by it.
In fact, many of our conversations get into discussions about how to best navigate ourselves out of these negative spirals.
“I don’t need to kill it right now. I need to make sure I’m around for the next cycle that is favorable to my trading style.”
According to Anthony Crudele, most traders struggle because they are too short-sighted. He believes most successful traders think longer term—not about time frames but about how each trade, day, or week fits into the bigger picture of what the trader is looking to accomplish.
From an early age, David Hale had hustle in his DNA. At just 10 years old, he was sneaking into casinos to play slot machines. By 11, he was betting on horse races. And before long, he was hunting for arbitrage opportunities in baseball card values. Inspired by his bargain-hunting mother, David developed a “value-player” mindset that would eventually spark a deep fascination with trading the markets.
It’s hard to believe Denise Shull is a product of parents and grandparents who believed in “buy and hold” and wouldn’t even know how to sell a share of stock if asked to.
Today, Denise is well known as a Performance Coach to big Wall Street traders, specializing in modern psychoanalysis.
“I would not give a fig for the simplicity on this side of complexity, but I would give my life for the simplicity on the other side of complexity.” ~ Oliver Wendell Holmes
There’s a profound simplicity that can only be reached by working through complexity. It means that deep understanding is often simple, but achieving it requires grappling with and overcoming complexity.
Jason Leavitt believes this wholeheartedly. And this was his path.
When he first got involved in trading, everything seemed simple: buy low, sell high, make money.
Reinventing your career after 20 years is no small feat. Now, imagine trying to do that by becoming an active trader. That’s exactly what Andrew Moss is doing—but he isn’t going in blind.
Andrew’s fascination with the markets began as a teenager when his father introduced him to point-and-figure charts. From there, he pursued a career in brokerage and wealth management at a major Wall Street firm, gaining deep insight into the industry.
“We all have to follow our own path,” Andrew reflects.
Matt Kenah is Building Positive Momentum Every Day.
If we only learn one thing from Matt Kenah, I hope it would be this: “The only goal we should have every day is to live to fight another one.”
Matt has lived this ethos and he has been repeatedly put to the test. And passed.
Starting out on the Chicago Mercantile Exchange trading floor as a runner just out of high school, Matt quickly rose the ranks to Arb Clerk and was earning great money as a young man in his early twenties.
To say Andrew Menaker took an unusual path to Wall Street would be a severe understatement.
While negotiating with an armed bank robber to de-escalate the situation and ensure the safety of customers and bank employees, he had to let Wells Fargo know he wouldn’t be making it to his first interview that day and, therefore, would have to pass on an opportunity to work with the firm.
Among the many things that stood out during our conversation with David Lundgren, it was this quote: “I want to find a way to listen, and learn, and get a little bit better every day.”
This is a mindset that every trader, every human, can benefit from.
In his early days, David described himself as a “systematic researcher.” This process of discovery held sway for him, and when striking out on his own, he employed the same systematic philosophy to portfolio management and trend-following trading.
For Wall Street veteran Jared Dillian, getting away from Wall Street might have been the best thing he ever did for himself.
Now living in South Carolina, he can’t be further removed from the lifestyle of your typical Wall Streeter. And he’d have it no other way, as he’s convinced Wall Street took at least 10 years off of his life expectancy.
As Jared says, his stress levels are now “basically zero.”
Milton Marmanides does the hard work that traders don’t have the time to do. He sifts through the firehose of headlines, news releases, data points, and social media to cut through the noise and deliver only the market-moving information active traders need to make smarter decisions.
And in his nearly 25 years in the business, first as a trader, and now as a market data provider, he’s seen a lot.
