I had a conversation recently that stayed with me.

Earlier this month, I made a decision. I wanted to know my members better.

Every day I show up, talk to you, and answer questions in our Masters in Trading Discord community. I watch familiar usernames scroll by.

These are people I’ve come to know. I see how they think. I see how they approach risk. I watch how they’re progressing with the trades, the tools, and the materials.

And I’ll tell you — there’s nothing better than watching the lightbulbs turn on in real time.

But the truth is, most of our interaction still happens through screens.

Digital communities are powerful. They allow us to learn together, move together, improve together.

But they also create distance. You don’t always get the chance to sit across from someone, slow the conversation down, and hear how the journey actually felt from their side.

So, I decided it was time to start shining some well-deserved light on the people who make this community what it is.

So I reached out to a member of the Masters in Trading community some of you might recognize – Jon.

If you’re inside the Discord, you know exactly who I’m talking about. He’s one of the steady voices in the room. Helpful. Thoughtful. Always working to understand the why behind what we’re doing.

We’ve worked together for about eight months, but this was the first time we’d actually spoken face to face.

And as he started describing how things have changed for him over the last year, something became very clear to me.

I already knew Jon was doing well.

What I didn’t fully appreciate — until I heard him say it out loud — was how profound the transformation had been.

In fact, his story explains what makes Masters in Trading different much better than I ever could.

Building a Framework

Jon is a physician. Highly educated. Comfortable making critical decisions with incomplete information. He’s spent decades operating in environments where precision matters.

If intelligence and discipline were enough to win in markets, he would have been miles ahead of everyone right out of the gate.

But he told me that despite years of reading, studying, and subscribing to quality research, he mostly felt like he was treading water.

He described long reports that never quite translated into meaningful returns. Recommendations that seemed to arrive after stocks had already moved. Ideas that sounded great, but fell short on defined risk management. An unsteady thesis underpinning each trade he made.

What stuck with me most was how he described the emotional weight.

The uncertainty.

Putting trades on and then lying awake wondering if he had missed something.

I’ve heard that feeling from engineers, executives, attorneys, business owners — incredibly capable people who somehow still felt like they were guessing.

Not because they lacked effort or capability. But because they lacked structure.

The Moment Things Started to Click

Jon didn’t start by diving headfirst into paid programs.

He watched video after video of the hundreds available on my YouTube channel.

He joined as many of our daily livestreams as he could. He paid attention to how we talked about markets.

He noticed how often we waited. He saw that when we acted, it wasn’t because I had a grand prediction — it was because something observable had changed.

So, he tested a small idea.

It worked.

Then he tried another. A few hundred dollars risked turned into a result that made him pause and say, “Okay, there’s a process here I need to understand.”

That’s when curiosity turned into commitment.

He joined the Masters in Trading Challenge. Then he stepped further into the ecosystem. And as he put it to me, slowly but surely the fog began to lift.

From Prediction to Positioning

At one point during the interview, Jon said something that made me smile because it’s a phrase I repeat constantly: We’re not trying to predict. We’re trying to position.

That shift changes everything.

You stop asking, “What do I think will happen?” And you start asking, “What is the market telling me right now?”

When you operate from evidence instead of opinion, confidence grows naturally.

Risk becomes measurable and manageable.

Patience becomes logical. Even losses make sense because they exist inside a system.

Jon told me he sleeps better now. He told me he doesn’t obsess after entries, and that he knows what he owns and why.

If you’ve ever spent days second-guessing trades, refreshing quotes, wondering whether you were early, late, or simply wrong – then you understand how great peace of mind really is.

Yes, There Were Wins

Of course, we talked numbers.

He mentioned a defined-risk trade where roughly $4,000 turned into about $30,000. He talked about other situations where a similar amount of exposure multiplied quickly once the thesis began to play out.

Closing out a profitable trade is always great. But seeing these ideas make meaningful impacts across multiple trades is truly the goal of Masters in Trading.

Even better was that he could explain the mechanics behind each trade. He understood why the opportunity existed. Why the structure worked. Why it was repeatable.

Without that understanding, wins feel random.

And random success is impossible to build on.

The Desk VS. The Island

Another theme Jon kept coming back to was something I’ve believed in from day one.

Community.

He told me this was the first time in his investing life that he didn’t feel alone. He could test ideas. Compare interpretations. Watch how other people processed the same information. Learn alongside traders at different stages of the journey.

It stopped being him versus the market. It became a group of serious people working to get better together.

In many ways, Jon’s journey resembles what happens on a professional trading desk — multiple sets of eyes, different experiences, people talking through risk and opportunity in real time.

And, in my experience, a community of like-minded traders is the key to making better trading decisions.

For those interested in hearing more about Jon’s journey, I’ve made our entire chat available over at my YouTube channel. You can watch the entire interview at the top of the page.
 
And, if like Jon, you’re interested in joining our tight-knit Masters in Trading community…

The best way to dive in is through The Masters in Trading Options Challenge. 

The Challenge is where we take everything you learn in my daily LIVEs — fixed risk, thesis-driven exits, laddered entries, defined-duration trades, and emotional discipline — and put it into practice in a structured, step-by-step environment.

Just click here to check out what the Masters in Trading Options Challenge has in store for you.

Remember, the creative trader wins,