It’s happening again.

You know you’re at frothy market highs when you start seeing videos about totally can’t fail easy shortcuts to early retirement by (fill in the blank with whatever financial trading scheme you want).

We saw this with crypto back in 2021. I remember arguing with a guy on X (then Twitter) who was out there telling people to retire early by staking their money on high interest earning liquidity pools. I got into another Twitter fight with some fresh MBA grad finance bro who was out there recommending random dividend shit stocks that were paying out 10%+ to his followers.

“Bro, you don’t understand. Every five grand you put in equals $500 a year for life. For life, bro!”

Mind you, I wasn’t being nasty or anything. I was simply asking what happens if stocks go down or those liquidity pools dry up? I was asking standard good faith due diligence type questions. But like the guy who pointed out that maybe the Titanic needed more life boats, I was ignored and ridiculed.

Then the Federal Reserve hiked interest rates and stocks fell into an 18 month bear market. Crypto plummeted back to Death Valley. Mysteriously, I didn’t see too many finance bros on Twitter soon after. Same with crypto bros.

But now markets are back at all time highs. The Fed just cut rates by half a point. Stocks are roaring. Bitcoin is back, baby! It’s all good. “Biggest bull market ever, yo!”

Which of course means gurus and finance experts and self-appointed wealth wizards are out there peddling their know-how for clicks.

The latest big idea I’ve seen involves buying LEAPS and then selling calls against those leaps.

What the hell am I talking about, you might be wondering? What’s a LEAP?

LEAPS

LEAPS are an option on a stock. It stands for Long-Term Anticipation Equity Securities — LEAPS. LEAPS are at least one year out from expiration, and sometimes they can go out as long as three years. An option, as you may know, is the right but not the obligation, to buy a stock within a certain time period. If I buy one option on Apple with a strike price of $200 that expires in one year, that means I have a year to exercise my right to buy 100 shares of that stock at $200. Option contracts are worth 100 shares each.

The appeal of options is they give you the ability to potentially control 100 shares without having to actually buy the 100 shares. The downside is that option contracts expire and they are more volatile than stocks.

Option contracts are also way cheaper than buying the shares. A $200 call option on Apple for December 19th 2025 as of this writing costs about $5,300 while 100 shares of Apple would cost roughly $23,000. If Apple goes up to $250 this time next year, the value of the option you hold on those shares would also go up. Let’s say our $200 option we paid $5,300 for becomes worth $7,000. That would mean you’ve made a profit of $1,700. That’s nearly a 25% return in one year. Had you bought 100 shares at $233 instead, you’d have also made $1,700, but you would have risked about $23,000 to do so. You would have also only made about a 7% return. You can see how options can give you enormous leverage on a stock.

The Strategy

---

However, there is a way to maximize your returns on that LEAP call. You could also sell calls against the stock. The key here is you want to sell calls that are high above the stock price (“out of the money”) and therefore unlikely to be exercised by the buyers.

And you want to sell calls with close expiration dates. Say, a week, or a month out. Right now, a November 1st, 2024 (one week from this writing) $240 call on Apple is going for about $200. Hypothetically, if you were to sell a $200 call like that every week, you could potentially make $10,400 a year. That’s with only one LEAP option that cost you a mere $5,300.

Now, imagine if you could buy 20 LEAPS. That would mean you could sell 20 calls against them, and make $208,000 a year, or over $17,000 a month. That’s a nice income stream. On top of that, you’ll also make $34,000 if Apple goes up to $250 and your LEAPS become worth $7,000 as mentioned earlier. That’s a grand total of $242,000 of profit in one year.

Sounds too good to be true? Well, that’s because it is, duh. What you see above is where the gurus all stop talking. They don’t mention the possibility that your calls might get assigned, forcing you to liquidate your LEAPS holdings.

They also don’t mention what happens if stocks slide into a bear market, which is the biggest threat. Even a strong bull market will see big dips and corrections. But what happens during a prolonged downturn, like what we saw in 2022 through late 2023? Or what happened after the Dot Com meltdown? Or after the 2008 financial crash? It took stocks years to get back to all time highs again after 2000. It took about five years for stocks to return to highs after 2008.

You can see the problem here if you have a bunch of financial assets that EXPIRE in a relatively short amount of time. Even if you have a three year LEAP option, it might take that long before stocks get back to even. Meaning you would likely lose your investment. Option values go down way harder than stocks during pullbacks.

Yes, you could buy put options to hedge your positions. But those may only limit your downside risk. You can still lose money. Lots of money.

I’m not saying this LEAPS strategy doesn’t work or can’t work. I’ve bought LEAPS myself and profited. I’ve also sold coverered calls and put options. I’m just saying that you need to get a fuller picture of what you’re getting into. You need to understand the substantial RISK you are taking on by doing this. Using a small part of your portfolio to trade might be okay depending on your networth and risk tolerance. This strategy could potentially offer some relativey steady returns if done prudently.

But is this LEAPS stategy something you could actually RETIRE on? I certainly wouldn’t bank my retirement on this. It would only “work” assuming you have significant assets to fall back on should the market crap out for 18 months. Thinking you’re going to make $10,000 or whatever a month every month no problem is foolish.

---

I really get tired of these so-called experts out there chasing clicks and ad revenue by misrepresenting trading strategies or whatever other financial schemes are in vogue. Actually, no. It pisses me off. Because the fact is trading is high risk and few people make regular money from it. At worst they offer half-baked schemes that only work in optimal markets. At best they’re not giving you all the facts.

Be on the lookout for these gurus and bull market snake oil salesmen. Do your own thorough research. Do not get sucked in by the hype. Do not just blindly follow some strategy because you think it’ll give you easy returns. Be careful out there.