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!
“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.
They are only losses if we don’t learn something from the experience.
When traders woke up on Monday, August 5th to the VIX at 65 and the Nasdaq index down 5% overnight, they didn’t need a cup of coffee to snap into high alert.
The easy first question to ask was: “What happened?”
If there’s one thing Anne-Marie Baiynd learned after making the transition from a business owner to a trader, it’s that she’s no longer in charge.
The market, unlike her employees, doesn’t do what she asks it to do.
She needed to learn to give up control. And it wasn’t easy.
In fact, it was so hard that she almost lost all of the hard-earned money she had salted away from years of successfully running her business. To say this would be stressful for a family and a marriage would be an understatement.
It wasn’t until Nik’s father suggested he get involved in High School Wrestling that he began to learn what drives him: Discipline, Regimen, and Humility.
For the first time in his life, wrestling gave Nik recognition. He liked it and knew the only way to maintain it was to go all-in.
From high school and into college at the University of Minnesota, wrestling taught Nik how to become the man who would soon enter the ring of Mixed Martial Arts and the UFC tour circuit.
When Michael Nauss first sat down at a trading desk, his computer had a keyboard and a screen. But no mouse.
And his screen displayed an order book. But no charts.
Thus began his career as a scalper working the order book, who paid no attention at all to trends or technical analysis. He was simply trying to find spots to buy ahead of large buyers and flip the position out for a quick couple of ticks. Do this a couple hundred times per trading session and perhaps he’d have a successful day.
