Trading Without a Net: Why I Don't Use Stops on Options Trades

mod (Andy) note: "Blast from the past - Best of Eddie" - This one is originally from September 2010. If there's an old post from Eddie you'd like to see up again shoot me a message.

I've received a few messages from you guys about my recent DXD and SLV options trades, and I wanted to take a minute to explain part of my trading strategy when it comes to options. As you know, the silver trade is working well so far (up 18% in 8 trading days), the DXD trade not so much (down 66% in 9 trading days).

When you invest in something - anything - the value of it should rise immediately. If you buy a stock, bond, commodity, or derivative and it doesn't go up immediately, you were either early (best case) or wrong (worst case). Anyone who tells you otherwise is trying to sell you something. In order to be a long-term success as a trader, you have to cut your losses short and let your profits run. Stop loss orders are an excellent way to achieve that level of risk management.

I am generally in favor of using stops on a trade. For example, if I go long a stock I will generally set a stop loss 15% below my entry point. In other words, if I buy XYZ for $10 a share I cut my loss short if it drops to $8.50 a share. Mind you, this is on stocks I'm trading. If I'm buying something for the long haul, I generally don't mind so much if it gets a little cheaper and I can buy more.

Likewise, when I'm right about a stock and it goes up immediately, I'll usually place a trailing stop to lock in my profit if the stock turns around and starts dropping. You can't lose what you don't put in the middle. I usually set trailing stops much tighter than stop loss orders because I want to lock in maximum profit. If I have a stock rise 15% from where I bought it, I'll usually place a trailing stop 5% below the market price. That way the stock can continue to go higher and make money for me, but it gets sold the minute it decides to head south.

This is all really basic trading strategy and I don't mean to insult anyone's intelligence by explaining it. I just wanted to provide some context for when I explain why I don't use stops on option trades.

Maybe you have to be a veteran futures trader to fully get this (or at least be dumb enough to agree with it), but options have a built-in stop. When trading options, you can never lose more than 100% of your investment. I can hear some of you snickering right now, but I'm serious. Anyone who has traded straight futures will tell you that if shit goes sideways, you can be on the hook for a lot more than 100% of your investment. You might face a margin call where you have to send in three or four times your initial investment just to get back to zero. And that sucks ass. So knowing your downside is limited to 100% can be oddly comforting.

Options are a leverage play, and volatility goes hand in hand with leverage. The more leverage you have, the more violent the swings are. Think about it: the big news when the crisis struck was that some banks were leveraged at 30:1. That kind of leverage can really amplify gains when you're right about something, but if it's used against you, that kind of leverage will destroy you quickly.

So let's look at the DXD trade. DXD is a leveraged ETF that rises in value as the DOW drops, and vice versa. It is leveraged at 2:1, so if the DOW rises by 2% in a day, DXD drops by 4%. Stock options represent 100 shares of the underlying security. So if you buy options on IBM, you're taking a position in IBM leveraged at 100:1; the percentage gains and losses can be profound depending on how much IBM moves and in which direction. By buying options on DXD, you are essentially leveraging the DOW at 200:1, which is massive leverage (100:1 for the option, and the underlying is already leveraged at 2:1, hence 200:1 implied leverage).

Any time you're leveraged that much, stops can really cause you headaches. Because of the volatility involved, you can get stopped out of the market and then see the market whipsaw back another 50%. Then you're booking a big loss when you should be celebrating.

When I was trading commodities options for customers, my compliance department more or less insisted that I use stops. I would set the initial stop loss at 50% of the investment and still got stopped out more times than I care to remember only to watch the market rebound immediately. The NYMEX open-outcry pits were such a shitshow back in the day that I'm convinced the floor traders would purposely drop the market just to bang out the stops before taking the market higher.

Think about it in mathematical terms. 200:1 leverage is essentially a .5% down payment on the underlying security. So if you bought a house today for $200,000 and only put $1,000 down to do it, and that house rose by 15%, you'd be dancing. You just made a $29,000 profit on $1,000 investment. If it did the opposite, however, would you throw in another $29,000 just to get to even, or would you put the keys in the mailbox and walk away from the $1,000 you put up (moral arguments aside)?

That's the opportunity afforded to you by trading options on a leveraged ETF. If you're wrong, you can put the keys in the mailbox and walk away from the trade without losing a moment's sleep (assuming you didn't bet your rent on the trade). And that's why I don't use stops when I'm trading options. My downside is limited to 100%, but the last time I rang the cash register on DXD calls I pocketed 300% in under two weeks.

Incidentally, I'm not wrong about the trade. I was clearly early, but I'm not wrong. Wait and see.

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