To The Moon

The Brutal Truth Up Front 💀

The Damage: -$13.2K across two weeks

The Silver Lining: Still maintained 75% win rate with 53 positions

The Reality Check: Stock picks got massacred (-$21.4K) but options trading kept me breathing (+$8.2K)

Sometimes the market serves you a $36K reality sandwich with a side of humble pie. Here's what happened when I thought I could outsmart cruise ship momentum.

🏖️ Trading While Sipping Latte (Spoiler: Bad Idea)

Last week I was supposedly "on vacation" - you know, that thing normal people do where they actually disconnect? Yeah, that's not me. I kept trading and posting Trade Feeds because, let's be honest, market addiction is real.

The result? Proof that you can't half-ass trading. Either you're in or you're out. Trying to do both leads to expensive mistakes.

Withdrawing trade profits for living expenses and fund other investments

There are many reasons why we all trade. Among mine are securing income to fund living expenses, achieve financial freedom earlier and build generational wealth. What are yours?

Regardless of your motivations, remember to take profit.

WW 34 and WW 35 2025 Top 10 Profitable Trades

Profitable Trades

Top 10 most profitable trades ranged from $2205 to $332.

WW 34 and WW 35 2025 Top 10 Unprofitable Trades

Unprofitable Trades

Top 10 most unprofitable trades ranged from $15.5k to $48. Five positions exceeded $1k in losses, though the losing tail continue to remain manageable.

Now let's dive into the three trades that taught me the most expensive lessons of August.

The Hall of Shame: My Top 3 Disaster Stories 🚨

1. $Royal Caribbean Cruises(RCL)$: The $36k Titanic Moment 🚢

RCL Daily Chart

Taking in $36k loss closing the largest unprofitable positions in the portfolio

What I thought: "This cruise stock is ridiculously overvalued at almost 30x earnings!, consumers got to pare down expenses due to reduced spending power and global uncertainties"

What the market said: "Party and vacations are more attractive past times than growing retirement account"

I went short 325 shares thinking I was a contrarian trader spotting an obvious bubble. The stock just kept climbing like it was powered by rocket fuel instead of diesel engines.

The painful lesson: Fighting momentum without a clear catalyst is like bringing a knife to a gunfight. I finally surrendered at $363, eating a massive $36K loss.

Why you should care: We've all been there - convinced we're right while our account balance says otherwise. Sometimes the best trade is admitting you're wrong.

Open Positions:

• short 325 shares at average cost of $253.13

• 1 remaining short puts $290 strikes expiring on 5th Sept.

Trade decisions this week:

• Priority: Let the last remaining short put to expire worthless by 5th Sept.

• Take loss if RCL breached $350 (done)

What I'd Do Differently: Set a stop-loss at 15% instead of hoping for a reversal. Also, shorting a stock in a strong uptrend without a clear catalyst = recipe for pain.

2. $SUPER MICRO COMPUTER INC(SMCI)$: When “AI Everything” Meet Reality 🤖💥

SMCI Daily Chart

The setup: Bought into the AI hype at $66.98, thinking every AI-adjacent stock was going to the moon.

The reality check: Down 30% after earnings because, surprise, not all AI plays are created equal.

Currently sitting on 1,470 shares of what I now call "expensive MBA from the University of Hard Knocks, AI Trading Department". The 200-day MA at $39.76 is my final line in the sand.

Key insight for you: There's a difference between AI leaders (NVDA, MSFT) and AI wannabes. Choose wisely.

Open Positions:

• Long 1470 shares at $66.98

• 15 short calls all expiring within the month of Sept between strikes of $45 and $50.

Trade decisions this week:

• Priority: Let these covered calls expire in the money and reduce positions at $45. Take loss of about 35% if sold shares at $45.

• Sell new calls to replace expired ones if price trades within $40 to $45 range

• Cut loss on all positions if price close below 200 days SMA currently at $39.76 for about 45% capital loss.

What I'd Do Differently: Position size smaller on "story stocks" and have a clearer exit plan. When AI hype meets reality, reality usually wins.

3. $iQiyi Inc.(IQ)$: The “Chinese Netflix” That Forgot to Netflix 📺

IQ Daily Chart

Held this for over a year after getting assigned on short puts. It finally moved up 47% recently, and I'm ready to break even and run.

The brutal truth: Sometimes "cheap" stocks are cheap for a reason. Not every streaming service is going to be the next Netflix.

Open Positions:

• Long 4500 shares at $3

• 45 covered calls at $2.5 expiring 19th Sept

Trade decisions this week:

• Priority: Let these covered calls expire in the money and sold all positions at $2.5. Take loss of $0.5/share. Overall trade was near breakeven after the past 1 year of selling covered calls for premiums.

• If price on 19th Sept fell below $2.5, sell new calls to replace those expired ones.

The Redemption Arc: What Actually Worked ✨

• SoFI continues to be my steady Eddie - consistent gains that keep the lights on while my "genius" picks imploded.

• META short positions delivered when I positioned correctly for the pullback.

• Options trading strategy salvaged what could have been a complete disaster, proving that diversified approaches matter.

September: The Market's Favorite Month to Crush Dreams 📉

Historically, September is when portfolios go to die. With VIX at historical lows of 15.35 but volatility potentially lurking, I'm preparing for:

• More position trimming (cleaning house)

• Reduced leverage (currently at ZERO - sleeping better already)

• Increased liquidity (35% vs. previous 20%)

The game plan: Survive September to thrive in Q4.

The Numbers That Matter 📊

Portfolio Performance:

• August 2025: -5.2% (-$23.6K)

• S&P 500: -0.1% (basically flat)

• My ego: Currently trading at penny stock levels

Lesson: Sometimes matching the index is actually winning.

Why I Share These Painful Details 🎯

Because successful trading isn't about being right all the time - it's about:

1. Risk management when you're wrong

2. Position sizing that lets you survive mistakes

3. Emotional discipline to cut losses before they become disasters

4. Learning from pain so you don't repeat my expensive lessons

Your Turn: The Community Question 💭

What's your biggest trading lesson learned the hard way?

Confess your trading sins in the comments - this is a judgment-free zone where we all learn from expensive mistakes!

Best story gets 50 Tiger Coins, and we all get to learn from each other's expensive mistakes.

• Anyone else getting crushed by momentum trades? Drop your war stories below!

• Who's with me on the September survival challenge? Tag a trading buddy!

• What's your 'I can't believe I did that' trade? Let's laugh together!

The Weekly Challenge 🏆

For next week, I'm challenging myself (and you) to:

• Make fewer trades with higher conviction

• Actually take profit when positions work (revolutionary concept!)

• Stop trying to catch falling knives without proper catalysts

Follow along: Only sharing my live trades with subscribers - hit that bell!🔔

Remember: We trade to fund our dreams, not to fund our nightmares. Sometimes the market reminds us which one we're actually doing.

Until next week's confession session: Will I finally learn my lesson about momentum trades? Will SMCI break my stop-loss? Will I actually take profits when I'm winning? Stay tuned for another episode of 'How Not to Trade Like a Pro'.

About This Chaos

This journal documents one trader's journey towards making $1 million in trading profits - complete with ego-bruising losses, lucky victories, and everything in between.

Join the ride, learn from my mistakes, and maybe we'll all get rich together (or at least you’ve read some horror trading stories to laugh at me).

Positions mentioned are for educational entertainment. Please do your own research before following a guy who just lost $36K on a cruise stock.