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.

This is not the case with Tom Basso.

In fact, if Tom didn’t tell you that he makes his money from trading and managing other people’s money, you’d probably assume he’s simply a retiree who enjoys spending his time tending to his garden and landscaping, hosting dinner parties, golfing, singing in choir, and traveling.

One thing you wouldn’t guess is that he has perhaps hundreds of thousands of dollars at risk in the market at any one point in time!

It would be easy to surmise that achieving the level of success Tom has makes it simple for him to adopt a detached, chill mindset about his trading. But he will correct you and tell you that the mindset came first. And his trading, in fact his whole life, thrives on his unique ability to “enjoy the ride.”

Steve and I are both smitten with Mr. Basso and we left this conversation invigorated and motivated to do more of working for ourselves and less of what isn’t.

In short, we both want to be Tom Basso.

You will no doubt enjoy this delightful conversation.

“I don’t need to kill it right now, I just need to make sure I’m around for the next cycle that is favorable to my style of trading.”

According to Anthony Crudele, most traders who struggle do so because they are too short-sighted. He believes most successful traders think longer term—not about time frames but about how each individual trade, day, or week fits into the bigger picture of what the trader is looking to accomplish.

Meanwhile, outside distractions can be too much to overcome if we don’t have our “houses” in order. “A lot of my success comes when I don’t have a lot of outside distractions.” And it makes sense. Anthony talks about how what’s happening in your life affects our patience and our discipline.

And he knows. At too young of an age, he suffered a stress-induced heart attack that almost took him out of the game for good.

It was a wake-up call. “Just let shit go. So many people get consumed by this business and can’t get past the screens.” Anthony got to a level of frustration with trading and his health that he said to himself: “I don’t want to live this way anymore.”

He withstood the storm and came out the other side a better trader and more importantly — a better human.

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.

Born in England to an American mother, David’s journey took a pivotal turn when his family moved back to Texas during his teenage years. It was there that he cut his teeth in high-velocity day trading at a proprietary trading firm in Austin, Texas.

But David had bigger ambitions. Determined to join the elite ranks of hedge funds or bank trading desks, he made the bold move to London. Yet, what he hoped would be a leap forward turned into a series of challenges that tested his resolve.

These setbacks not only humbled David but also sharpened his focus, discipline, and ability to exploit unique market edges — what he calls “glitches.”

For traders who feel like the odds are stacked against them, David’s story offers both illumination and inspiration. Get ready to dive into a tale of resilience, reinvention, and relentless pursuit of success.

Enjoy the episode.

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.

Before this, she traded in Chicago and ran a proprietary trading desk in New York City. All of which became fodder to help her publish a book on her expertise — for which she went to school. Later, her book caught the attention of Hollywood in the crafting of stories for the Showtime TV series Billions.

In this episode of Off The Charts, we chat with Denise about emotions and why we can’t make decisions without them.

She also reveals the most powerful human emotion of all — regret, and our natural drive to avoid it at all costs. In trading, and in life.

If traders can get their risk perceptions right and foster an awareness of other’s positioning and their perceptions, a trader can get a step ahead of the game.

This is a heavy episode with a lot to unpack. Settle in.

Steven Place has been around the block. He’s been through the ringer. And he has the scars to prove it.

A former Rocket Scientist, Steven is a self-taught options trader who’s been plying his craft for nearly two decades.

He has spent a lot of time studying options analytics and “hacking” execution strategies to create better outcomes for himself. And one big thing he’s learned over the years is: “If you’re going to be stressed anyway, doing the same amount of work, why not shoot for the fences once in a while? You’ve got to find some convexity, somehow.”

Having been through it all, Steven finds himself in a better mental space these days, and he riffs on how becoming a parent has put things into a clearer perspective.

Steven absolutely believes options trading is the most fascinating thing one can do right now. Listen to him and you might come away believing that he’s right.

Enjoy.

“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.

But as he dug into it, his research and experience led him down numerous paths — some fruitful, some not so much — and he, like many of us, reached a point near analysis paralysis. Upon reaching this apex of his learning curve, it was then that he began stripping away the extraneous and superfluous to reach the core of what mattered most to his style and skill set.

“We need to be able to comfortably execute within our comfort zone,” Jason says. And the work of getting his process down to the most simple of data points and execution triggers was, and continues to be, an essential ingredient for him to find success.

And one of the key methods he gets to the core of what works is to use his own trading results and experiences as direct feedback. If or when he stubbornly ignores his own data, this is when trading becomes hard. The lesson is to listen to what your trading stats are telling you.

One of those lessons he learned early on was that to go from bad to good and good to elite he needed to push himself to take bigger positions when the markets aligned best with his skillset. He needed to focus on developing the sense of when conditions are right for him to push.

Please enjoy this conversation with Jason Leavitt.

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.

Blazing his own trail, however, hasn’t been without its challenges. Transitioning from nearly two decades of a steady salary to making a living solely through trading has been a major shift. He notes the adjustment from a long-term wealth management mindset to a day-by-day focus on profits and losses. Balancing the need to be aware of the PnL while not obsessing over it is a delicate act that takes practice.

Andrew is also navigating new habits, fresh perspectives, and the biggest realization of all—the real battle in trading is between you and yourself.

If you’ve ever had to reinvent yourself, or are thinking about doing so, this episode of Off The Charts will both educate and inspire you.

Enjoy!

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.

But there was a growing discomfort within him that questioned what value he was bringing to the world. He thought there was more he could do.

So after three years in the Chicago trading pits, he left to pursue a higher calling in the Catholic Seminary. He studied to become a priest.

But on the eve of deciding whether to embark on a voyage to Rome to further his education that would keep him abroad for at least two years, his mother was diagnosed with a serious bought of cancer.

There was no way Matt could leave the country with his mother about to face the biggest challenge of her life.

As Matt tells it: “God had other plans.”

And so at that point, he decided to pivot back to the Chicago trading pits and make a go at it in the markets.

It would be great if the story ended there with Matt finding tremendous success, but it wasn’t easy. Matt would suffer numerous financial losses along his path. One of which put him firmly back at square one, trading 1 and 2 lots, just to find and rediscover his rhythm and train himself in new habits and languages to succeed in a screen-based trading environment.

If you commonly find yourself in a trading rut (or worse), the wisdom Matt shares in this podcast will go a long way toward getting you back on the right track.

This is an episode you’ll likely bookmark and return to, as needed when times get tough.

Enjoy!

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.

Nevertheless, the circumstances of his armed conflict made the local news and caught favorable attention of the necessary people at Wells Fargo and he was quickly hired anyway to work with people who were also planning heists of their own — riches from Wall Street.

This set Andrew on a path to eventually set out on his own to work with heavy hitters at big banks, hedge funds, proprietary trading firms, and large retail traders, helping them get out of their own way.

And things he learned may come as a shock to some of you. The biggest players on Wall Street share many of the same hangups as you: Doubt, uncertainty, fear, anger, envy, elation, disappointment, dissolution, greed, and vice.

But the true masters have learned some tricks to operate at peak performance.

In this chat, Andrew shares some things he’s learned about these masters and some common pitfalls that bedevil the rest of us.

And you may be surprised to learn that your emotions can be an aide, rather than a hindrance to profitable trading!

If you want to be better at trading, or any other endeavor you’re pursuing, this nearly hour-long chat is a worthwhile investment in your future.

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.

David firmly believes that “the best teacher I have ever had is the Market itself,” and “the only way to learn is to do it.”

Trend followers or those interested in trend trading will find a lot of nuggets for further meditation from our conversation including:

* “Trendfollowing is contrarian.” – doing what nobody wants to do: buy high, sell low.

* “There is no such thing as trendfollowing on the short side.” You need targets when holding a short position, which is the opposite of what trend followers do.

* Expect to lose.

* Misplaced Expectations - “If you are anxious about the market, it’s because you aren’t getting what you expected. Which means you aren’t listening to the market.” Traders lose due to misplaced expectations.

* “When all you want to do is avoid losses, you manifest losses simply by obsessing over them.”

* “In trendfollowing, there is no target. You go until the wind changes.”

* In horse racing terms, “the benefit of a trendfollowing portfolio is you can change your horse in the middle of a race.”

These are just a handful of an overabundance of trader pearls of wisdom that were shared in this conversation with David Lundgren, please enjoy.