This month, I’m adding American Airlines to my portfolio – but not as one of my regular monthly $1,500 investments. No, AAL falls into my “intriguing but uncertain” category, warranting just a $100 stake. Let me explain why and how this fits into my dual-strategy approach.

Two Investment Strategies, One Goal: Free Shares

Before diving into AAL, let me clarify my two distinct approaches:

The up 40% $1,500 Investments

• Monthly investments of $1,500 in stocks I’m confident about
• Wait for a 40% gain
• Sell enough to recover the $1,500
• Keep the rest as “free shares”

The double $100 Investments

• Small $100 bets on stocks that intrigue me but seem risky
• Wait for a 100% gain (yes, double or nothing!)
• Place a 10% trailing stop order to sell half when it doubles
• Keep the remaining shares as “free shares”

Why AAL Gets the $100 Treatment

Here’s why AAL landed in my “interesting but scary” $100 category:

• Forward P/E of 7.56 – looks cheap, but maybe for good reasons?
• Revenue growth of 1.20% year over year – technically positive, like being the tallest short person
• They’re raising their profit outlook to $0.55-$0.75 per share, which sounds better than losing money
• The stock was worth triple in the past (but so was my high school varsity jacket, and you don’t see me investing in that)

The Double Up Strategy in Action

For AAL, here’s the master plan:

1. Invest $100 (already done – no turning back now!)
2. Wait for it to double (from whatever price I got it at – I’m not showing you that number yet)
3. Set that 10% trailing stop order for half the shares
4. Keep the rest and pretend they were free all along

Why Two Different Strategies?

Simple math (my favorite kind):

• $1,500 investments: 40% gain needed = seems reasonable for solid companies
• $100 investments: 100% gain needed = higher risk, but who cares, it’s just $100!

Think of it like dating: The $1,500 investments are for companies you’re ready to commit to, while the $100 plays are more like casual coffee dates – low commitment, but who knows?

Final Thoughts

For now, I’ll just enjoy my new status as a proud owner of… checks calculator… enough AAL shares to not even get a free bag check. But if it doubles, I’ll get my money back and keep some shares for the long haul. If not? Well, I’ve spent more on airport coffee.

Here’s to small bets, big dreams, and having just enough skin in the game to make checking stock prices entertaining!

Disclaimer: This is not financial advice. If you’re taking investment tips from someone who uses dating analogies to explain investment strategies, we need to have a serious conversation about your life choices.