August 15 Options Crunch: When Three Trades Go South (and One Saves the Day)

 Setting the Stage

I went into early August feeling confident.

Selling premium. Collecting credits. Playing the probabilities.

But as we approach August 15, I’m looking at three short calls that are underwater — and one that’s actually holding the line.

It’s a perfect case study in why expiration clustering can be dangerous, how quickly losses can pile up, and why one good trade can soften the blow.

MSTX – The Quick Theta Play That Backfired

I sold this call just two days before the rally. Thought it would be an easy win on a quiet biotech name.

Then MSTX jumped above my breakeven almost immediately. Now I’m nursing a 42% loss in under a week.

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SMCX – The Slow Burn That Exploded

This one’s been creeping up for weeks, but I kept telling myself “it’ll roll over.”

It didn’t.

Now the short call has more than doubled in price. I’m down $505 — a 117% loss on the risked capital — and today alone it cost me $270.

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CHYM – The “Safe” One That’s Not So Safe

From my earlier post, CHYM was meant to be a calm, out-of-the-money play.

But with the stock just $0.05 below breakeven, any small move could flip me negative fast.

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CONL – The Lone Bright Spot 🌟

Finally, some good news.

This short call is working exactly as planned — time decay is doing the heavy lifting, and the stock is staying well away from trouble.

Up $38 (33.63%) so far, and if it keeps this pace, I’ll likely take profits early to avoid any last-minute gamma surprises.

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🧠 What Went Wrong (and Right)

Mistakes:

1. Overconcentration on one expiration date – All four trades end on 8/15. One bad week hits all positions.

2. No hard exit rules – I didn’t set P/L alerts to automatically cut losers.

3. Underestimating volatility – MSTX and SMCX both moved more than expected without major news.

What Worked with CONL:

• Entered early enough for theta to accrue.

• Avoided a volatile name or earnings risk.

• Stayed disciplined and didn’t over-size.

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🔧 Damage Control Plan

• MSTX: Buy back if it breaches $35.50.

• SMCX: Roll or close if it pulls back to $8.00.

• CHYM: Close if I can scratch the trade for break-even.

• CONL: Take profits at 50–60% of max credit.

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💡 Lessons for Future Me (and You)

• Never stack too many trades on the same expiry.

• Set automated exit rules — don’t leave it to willpower.

• Respect sector volatility — biotech and small-caps can run on whispers.

• Size small enough that one loss doesn’t wreck the month.

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Final Thought:

Selling options is like running an insurance business.

Most months, you collect the premiums. Some months, you pay out.

The trick is making sure the payouts never exceed what you can recover from — and remembering that one smart trade can still keep you afloat when the rest are sinking.

This Week's Options Trading P&L Update

 Here's the latest look at my weekly realized profit and loss (P&L) from options trading—with a special update clarifying that CHYM reflects Chime Financial, Inc., not an unknown ticker. The summary, table, and graphics below highlight performance by ticker for full transparency.

Options Trades Breakdown

Weekly P&L Bar Chart

This visual snapshot shows the size of each trade's realized profit or loss.

Bar chart of weekly realized profit and loss from options trades by ticker

Highlights & Commentary

• Best Winner: RDDT's $175 call netted the highest absolute profit for the week at $806.

• Consistent Wins: Single profitable trades on UNH and SMCX, and two combined TSLL puts, all contributed to solid gains.

• Minor Loss: The only losing position was a $35 put on CHIME Financial (CHYM), for a relatively minor $80 loss.

• Balanced Performance: The majority of trades were profitable, with results spread across technology, healthcare, and finance sectors.

Featured Company: Chime Financial (CHYM)

Chime Financial, Inc. made headlines with its 2025 NASDAQ IPO and is now confirmed as the referenced CHYM ticker in this weekly recap.

Key facts about Chime Financial as of July 2025:

• Ticker Symbol: CHYM

• Industry: Financial Technology

• IPO Date: June 2025

• Recent Price: ~$31.63

• Market Cap: ~$11.5 Billion

• 2024 Revenue: $1.8 Billion

• 2024 Net Income: -$25.34 Million

• Notes: Fintech leader in digital banking targeting consumer markets

Reflections

This week’s options trading underscored the importance of conviction in trade setups and the value of position sizing. With CHYM’s identity clarified as Chime Financial, the diverse sector results are clearer than ever, helping guide next week’s approach. Consistent review and thoughtful adaptation are key as market conditions evolve.

My Options Recap – Cashflow, Covered Calls & Expiry Plans (June 20)

With June 20 expiry just around the corner, I wanted to take a moment to walk through some of my open options positions — a mix of cash-secured puts and covered calls — that have been generating income and managing risk across market swings.

Some are deep in profit territory. Others are hovering near assignment. But overall, this strategy is doing exactly what it was designed to do: produce consistent cash flow while staying within my risk tolerance.

Let’s break them down one by one.

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🔻 SMCI $46 Put – High Premium, Still In Control

📅 Sold: Feb 26
💰 Credit Received: $7.40
📉 Current Stock Price: $44.44
📉 Current Option Price: $1.75
✅ Break-even: $38.60
📈 Today’s Return: +42.05%
📈 Total Profit So Far: $565
🎯 Total Return: +76.35%

This put is currently in-the-money , but still showing strong returns thanks to that juicy premium collected earlier in the year.

I’m totally fine taking assignment here — owning SMCI at an effective cost of $38.60 would be a great entry point. If it rallies before expiry, even better.

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✅ SMCX $40 Put – Nearly Max Profit

📅 Sold: [Date not specified]
💰 Credit Received: ~$4.00
📉 Current Option Price: $0.01
📉 Current SMCX Price: $42.09
🎯 Total Return: +99.44%

This one’s basically a done deal. The option is trading at just a penny, so I’ll likely see the entire premium as profit when it expires worthless.

A simple, clean win.

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🟠 SMCX $30 Covered Call – Deep ITM, Stock Ran Fast

📅 Sold: May 8
💰 Average Credit: $3.70
📉 Current Option Price: $12.00
📉 Current SMCX Price: $42.09
📉 Today’s Loss: -$210.00
📉 Total Return on Option Leg: -224.32%
🎯 Breakeven: $33.70

This is where things get interesting.

I sold a covered call on SMCX at the $30 strike back in early May. Since then, the stock has absolutely taken off — now trading at $42.09. That means my short call is deep in-the-money , and the option leg is showing a large paper loss.

But here's the key:

• I locked in $3.70/share in premium.
• My effective sale price is $33.70/share.
• Even though the call is losing money, the stock appreciation more than makes up for it .

💡 Bottom line: This position is still profitable overall — just not from the option side anymore.

📌 Plan: Let it get called away unless I want to roll to a higher strike or extend into next week/month.

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🔥 TSLL $9.70 Covered Calls (5 Contracts) – Huge Premium + Stock Surge

📅 Sold: May 16
💰 Credit Received per Contract: $5.92
📉 Current Stock Price: $12.40
📉 Current Option Price: $2.67
📉 Strike: $9.70
📈 Total Return: +54.90%
💸 Total Profit: $1,625
🎯 Effective Breakeven: $15.60

Now this is how you love to see a covered call play out.

Sold five contracts on TSLL at $9.70, collected a massive $5.92 in premium. Then the stock took off — now sitting at $12.40. While these calls are deep ITM, the upfront premium combined with the stock move made this a very profitable trade.

Even if assigned, this is a total win.

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💡 Key Takeaways

• Premium capture works , especially when selling during volatility spikes or ahead of earnings.
• Covered calls cap upside , but that tradeoff is worth it when you're happy owning the underlying.
• Don’t panic when trades go ITM — they’re only losses if you mismanage them.
• Always consider rolling if you want to stay long the stock and keep collecting income.

This is shaping up to be a textbook expiry week — some assignments incoming, but that’s part of the plan. Either way, I'm ready to adjust or collect and move forward.