“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.

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.

For Nik Lentz, being scared is Not an Option.

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.

When you are chasing a wave, you can’t be anywhere else. You have to be present.

Similarly, you can’t be anywhere else when you are chasing trends. You have to be present.

Ian has worked hard to create the right mental and physical environments to increase his odds of presence. The places he’s lived would surely inspire envy in anyone who cherishes beautiful natural surroundings and ocean breezes: San Francisco, Hawaii, and the underrated Gulf Coast of Florida.

Ian said it best when we said: “Find what brings you joy, then do it!”

Born with an entrepreneurial spirit and temperament, Michael grew up in a working-class community full of blue-collar, salt-of-the-earth people who worked honest days for an honest wage. And it rubbed off on him. How could it not? 

In order not to be a financial burden on his family, he knew he needed to get out there and hustle. He shoveled snow, mowed lawns, caddied, and worked as a server and waiter. He worked 15 hours a week while in college so that he could earn a degree from Columbia University.

Flying down a mountainside on two skis while negotiating tight turns and ever-changing microclimates would be a terrible time to lose focus.

Todd Gordon knows this. If he hadn’t quickly learned this skill in his journey to competitive ski racing, he would’ve likely landed himself onto a stretcher and an air-lift back to base.

There was no other choice. 

But for Todd, he’d have it no other way. From a young age, when he found an interest in something – whether skiing or finance – he’d go all in. Nothing else mattered.

Heading into the COVID-19 pandemic, Caleb Franzen was working a corporate banking job that felt like a dead end. “It felt like I was just being moved around from one boiling pot of water to the next.” 

Additionally, he had traded during college and what worked in the market didn’t jive with what he had learned in college. “Never once did I use anything in my banking job that I learned in college.”

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?

This episode of Off The Charts may become one of the most important episodes we ever publish. Please give it a watch (or a listen).

Jason Perz has grown comfortable with risk. 

We've all been there. Think about the time you first got interested in trading. It was exciting thinking about all the potential money we could make. But then we were quickly overwhelmed with the reality of all the things we didn't know. Former aspiring traders never made it past this moment. The mountain they had to climb just looked too daunting. When Jason Krutzky left the road after spending years touring with a rock band through North America and Europe, he decided he wanted to try his hand at full-time trading. 

If there’s one thing Brian Lund learned about himself over the past 30 years in the markets, he must write. Without a doubt, without even thinking about it, he knows that to express himself and to complete his thoughts into productive trading, he needs to sit down and start writing. And this makes sense. We hear this a lot from our smart friends. Barry Ritholtz once wrote: “I write to find out what I’m thinking.” 

If there is one thing that stands out from any conversation with Brian Shannon about the trading process, it is this: For discretionary traders, there are no rules. Instead, there are “guidelines.” And because Brian is human, he occasionally breaks his guidelines and suffers the same consequences as anyone else. Everyone gets what they deserve. Even a trader of 30+ years like Brian Shannon. If a trader buys the dip or sells the rip without a plan to control her risk then she, too, will get what she deserves. Eventually. The market is always on the hunt for our weaknesses. 

Nobody is having more fun than Kenny Glick. He’s found the perfect outlet for combining his myriad passions of risk-taking, education, and entertainment to the benefit of anyone who gets caught in his orbit. 

In the first episode of our new podcast interview series, Off the Charts, my co-host Steve Strazza and I interviewed one of our favorite people on Wall Street, Jay Woods. But he’s not just our favorites, he is a favorite of many. I would argue he’s the most popular man on Wall Street!