How One Trade Changed My Perspective on Winning Big in Options Trading

One trade, one structured setup — and a 500% profit that completely changed how I approach options. Here’s how I learned to win big without guessing

8 Months In — Still Figuring It Out

By July 2023, I was about eight months into my trading journey.

Still adjusting. Still experimenting. Still working to apply the ITPM process — not just in theory, but in real-time markets, with real stakes.

That’s when we had a trading competition inside the ITPM Society.

The challenge? Present a live trade — something structured, executed with conviction, and defined by risk. This wasn’t about flashy calls or perfect hindsight. It was about whether we could apply the frameworks we’d been studying.

And the timing? Couldn’t have been more interesting.

Just a few months earlier, in March 2023, Silicon Valley Bank had collapsed, kicking off a wave of panic selling across the regional banking sector. By July, some of the initial chaos had passed — but sentiment was still shaky.

That’s when I found a trade that changed how I see the whole game.

The March 2023 regional banking crisis triggered by the collapse of Silicon Valley Bank (SVB) sparked a sharp, sector-wide selloff. This chart of KRE highlights the speed and severity of the drawdown — driven more by fear and contagion risk than individual fundamentals.

The Setup: Buying Fear in NYCB (Now FLG)

I wasn’t looking for a “hero” trade.

I was looking for a disconnect — between what the market believed and what the fundamentals were actually showing.

One name stood out: New York Community Bank (NYCB) — now known as Flagstar Bank (FLG).

This wasn’t a blind bet. I ran it through the same template I’d shared with my ITPM cohort. And the deeper I looked, the more it fit what I was learning to hunt for.

🔢 The Quant Setup Looked Asymmetric

• Earnings revisions had quietly started ticking upward

• Return metrics looked solid vs. regional bank peers

• High implied volatility made options attractive

• Short interest was still elevated — good for a potential squeeze

  
  

📉 The Narrative Was Outdated

NYCB had just absorbed assets from Signature Bank. Most investors lumped them in with the chaos, but management was painting a different picture:

• Deposits were stabilizing

• Liquidity was stronger than expected

• Margins had room to expand

• Guidance was conservative — leaving room for upside surprise

So what I saw was a fundamentally improving bank, still being punished by old fear.

That was the trade. That was the moment.

The Trade That Snapped It All into Place

This wasn’t a “throw something at the wall” setup. It was structured, sized, and executed based on a process I was learning to trust. For the ITPM Society competition, I needed a live, conviction-backed trade — and this was it.

Here’s how it all played out:

📊 NYCB Trade Breakdown — From Entry to Final Exit

🎯 Initial Position: Long Calls on NYCB

Component	Details
Stock	NYCB (New York Community Bank)
Trade Entry Date	June 20, 2023
Option Type	Long Call
Strike Price	$13.00
Expiry	October 20, 2023
Contracts Bought	700
Cost per Contract	$0.19
Total Initial Risk	$13,300

Chart of Flagstar Bank (NYCB) showing the aftermath of the SVB collapse, my June entry point, and the post-earnings breakout where I scaled out. This was the trade that taught me the power of process-driven conviction.

💰 Partial Exit After Earnings

On August 1, 2023, just after earnings:

• Sold 525 contracts at $1.05

• Collected $55,125

• Realized Profit (after fees/slippage): ~$40,200

• Contracts Remaining: 175

That partial exit returned almost 4x my initial capital, locking in the bulk of the gain while keeping skin in the game.

🔄 Adjustment: Managing the Remaining 175 Contracts

With the remaining 175 contracts, I took a more risk-conscious approach:

• Sold 175 of the $14 calls at $0.46 on August 4

• Bought them back at $0.09 on September 8

• Profit from vertical spread leg: ~$6,400

At the same time, I sold the remaining 175 of the $13 calls at $0.06, taking a loss of ~$2,900 on that piece.

✅ Net Result from Final Position Management:

• Net profit from spread leg: +$6,400

• Loss on final $13 calls: –$2,900

• Net profit from this leg: +$3,500

🧮 Final Trade Outcome

Total Capital Risked	$13,300
Total Capital Returned	~$79,900 (all exits)
Net Profit (Realized)	~$66,600
Return on Risk	~501%

This wasn’t a hedge. This wasn’t a gamble. It was a structured, high-conviction trade that evolved with the market — and it showed me what it means to manage a position like a pro.

Winning Big in Options Trading — But That Wasn’t Even the Best Part

The trade hit big.

But weirdly, the most important part wasn’t the profit.

It was that I’d finally executed something front to back:

• Sourced a thesis

• Structured the trade

• Sized it intentionally

• Tied it to a specific event (earnings)

• Knew my risk

• Didn’t interfere

This wasn’t a lottery win. It was a process win.

This was the first time I truly saw what winning big in options trading looked like — not because of a lucky bet, but because I trusted my process, managed risk, and followed the structure through.

4 Things This Trade Taught Me

1. Markets overshoot in panic. The narrative always lags the reality.

2. Earnings season resets sentiment faster than anything else.

3. Options work best with a catalyst. Don’t just buy time — buy timing.

4. A winning trade feels different when it’s earned. Not guessed.

Why I’m Sharing This

I’m not showing this to flex. I’m sharing it because this was the moment where I felt like I actually started trading professionally — not just throwing darts.

For the first time, I wasn’t reacting. I was planning.

And the crazy thing? This was still just the beginning of my trading journey.

It showed me that if I put the pieces together — structure, conviction, timing, risk — I could actually trade in a way that made sense… and reap the rewards.

Looking back now, I can see that this was a fair-sized position using an out-of-the-money (OTM) option — which, in many ways, is more of a tail-risk trade.

But the conviction I had in the setup was strong. I understood the risk, I liked the asymmetry, and I wanted to see it through. That’s what made this trade so formative.

And if you’re somewhere in that early stage — working through ITPM or building your own process — I hope this gives you a glimpse of what’s possible when structure replaces speculation.

Want to See More Trades Like This?

If you’re interested in following the journey as I continue building consistency using ITPM-style frameworks, you can join my members page — where I share:

• Exclusive trade breakdowns

• Videos and resources I actually use

• Extra content I don’t post anywhere else

  
  

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Want to Learn About ITPM?

Curious about the ITPM programs I mention throughout this post?You can explore them here — or get an exclusive discount on their online courses using the link below:

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Disclaimer:

The information contained in this article is provided for general informational and educational purposes only and does not constitute financial, investment, or other professional advice. The content reflects the personal opinions of the author based on publicly available information at the time of writing and should not be relied upon as the basis for any investment decisions. Earnings reviews may contain forward-looking statements that are inherently uncertain and subject to change.

Readers are strongly encouraged to conduct their own research and due diligence, and to consult with a qualified financial advisor or licensed professional before making any investment or trading decisions. The author and publisher make no representations or warranties, express or implied, as to the accuracy, completeness, or reliability of the information provided and accept no liability for any loss or damage arising directly or indirectly from the use of or reliance on the information herein.