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9 Ways to Destroy Your Account with Options

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Options trading is fun. Options trading is sexy. And options trading can destroy your account if you don’t know what you’re doing. Profitable options traders understand the principles of options pricing, order entry, and market mechanics. If you fail to understand these 3 critical elements of options trading, you are not actually investing. You are gambling! So before you hit the buy button on your first options trade, carefully read through this list to make sure you are avoiding these deadly mistakes. There’s a reason I know they’re deadly. I’ve made them all myself. Multiple times. So please, be smarter than I was! Mistake 1: Thinking the Guy on the Other Side of the Trade Is a Guy There is no such thing as easy money in options trading. Let me repeat: there is no such thing as easy money in options trading. As you start exploring options, you’re going to be be tempted by options that are low in price. Well, if the options are so cheap… why is somebody willing to sell them? Remember, the guy on the other side of an options trade isn’t even a guy. Or a woman. It’s a computerized algorithm developed by math and physics PhD’s that are way smarter than you or me. Those algorithms generate millions of dollars a day by selling overpriced options to overeager traders. If you think you see easy money, it’s usually a trap. Mistake 2: Trading Far Out of the Money Options An option is far out of the money when its strike prices is far away from the current stock price. Beginning options traders are often attracted to these options because they look cheap. We’ll Tesla Motors (TSLA) as an example. Let’s assume the stock is trading at $250. An at-the-money call option expiring in 3 months is priced at $19 (or $1900). But the $300 call is trading at just $4. Many beginning traders will be more attracted to the $300 call simply because it has a lower nominal price. However, far out of the money options require huge moves in short time frames to pay off. So you’re paying less money out of pocket, but your trade is much less likely to make money. Mistake 3: Trading Illiquid Options Options on major stocks like Amazon.com (AMZN) and Apple (AAPL) tend to trade with fairly tight bid-ask spreads, and it’s fairly easy to trade in and out of them at reasonable prices. However, you should be very careful with options on small and mid-cap stocks. They tend to have very wide spreads and do not have much trading volume. So odds are you’re going to have to overpay just to get into the trade, and get underpaid on the way out. And in some rare cases — particularly with very far out-of-the-money options, you may have an awful lot of trouble getting trades completed at all. Last year, I bought way, way out of the money put options on Ambarella (AMBA) puts and doubled my money. However, there was no market for the options, and I couldn’t get out at any price. I went from making over 100% on the trade to losing 100%! Mistake 4: Blindly Buying at the Bid and Selling at the Offer As I said earlier, algorithms generate millions of dollars a day by selling overpriced options to overeager beginners. How do they do this? They buy low and sell high. For example, right now I’m looking at April $17.50 calls on UnderArmour (UA). The bid is $1.30 and the offer is $1.65. That means the market maker will buy the option at $1.30 and sell it at $1.65. That gives them a tremendous profit margin. However, you don’t have to accept those prices. Try bidding and offering in the middle. For example, you could bid $1.48 (basically the midpoint) and still get filled. That would save you 17 cents, or $17 a contract. On a 10-contract trade, that’s $170! Mistake 5: Not Double-Checking Your Orders Before you hit send on your options order, double-check it. When dealing with options, you’re often looking at dozens or even hundreds of small numbers on a single computer screen, and it’s easy to make mistakes. Make sure you selected the right the expirations and strike prices. This is especially important if you’re entering an order with multiple legs. You may fool yourself into thinking you’ve found an especially attractive calendar or butterfly spread when in fact, you just got ripped off. Mistake 6: Selling Options While Naked Get your mind out the gutter! Selling naked options entails shorting calls or puts without any kind of hedge. This is what we call “picking up pennies in front of a steamroller.” Let’s talk about naked shorting of call options. This is a bearish trade because you will make money if the stock falls. But if the stock rises substantially, you’ll get destroyed. Let’s say we want to sell nVidia (NVDA) June $100 calls for $6.30. If NVDA is below $100 at expiration in June, I’ll have made a pure profit of $6.30, or $630, per lot sold. But if the stock was at $120 at expiration, the options would be worth $20 each, and I’d be out $13.70, or $1370, per lot. These are the types of trades where 1 bad trade can wipe out your last 10 good trades, so just don’t do them. Mistake 7: Ignoring the Calendar Events like earnings reports, FDA decisions, product announcements, dividend payments, conference appearances, and economic data releases can have a tremendous impact on options prices So before you place a trade, be aware of what’s on the calendar for the stock or ETF in question. For example, if Alphabet (GOOGL) is about to report earnings, its options will tend to be very expensive in the days before the report. Mistake 8: Not Understanding Options Pricing Basics Most options beginners think a $0.01 option is cheap and a $10.00 one is expensive. The reality is not that simple. An option’s

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Vintage Wall Street: The Paul Tudor Jones Documentary ‘Trader’

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Paul Tudor Jones, founder of Tudor Investment Corporation, is one of the greatest traders of all time. Jones has amassed billions of dollars in assets under management and personal net worth trading everything from futures to currencies to commodities. In the 1987 documentary Trader, PBS takes us inside Jones’ world of high-stakes, practically 24/7 trading. In it, you’ll learn: Why like our own Scott Redler, Paul Tudor Jones wakes up so early in the morning Just how quickly Jones can change his mind in the heat of the moment The awesome-at-the-time-but-horrible-now fashion choices of 80’s Wall Street giants. If you’re interested in learning about Jones’ trading style, we suggest you watch the embedded YouTube video — complete with Russian subtitles — above now. When it does surface online, it tends to disappear due to copyright claims. Interestingly, in the 1990’s, Jones requested it be removed from circulation, possible because it revealed too much about his trading style.

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4 Real-World Investing Lessons You Need to Know

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After 13+ years of looking at the market on a daily basis, and flushing a whole bunch of cash down the drain on idiotic trades, I’ve grasped a few realities about how money moves in the real world — far away from the textbooks and theory pushed at your average business school. Here are 4 of them 1. What You Know, Everyone Else Probably Knows, Too. Investors have a tendency to overestimate the uniqueness of their ideas, even though we’re all drinking from the same information cup. Furthermore, the presence of social media outlets like Twitter (TWTR and Facebook (FB) have drastically accelerated the speed at which investable information is distributed. That means that with few exceptions, everything gets priced into the market pronto. So if you’re thinking of buying bank stocks because The Fed’s about to raise rates, or shorting  Apple (AAPL) because of slowing revenue growth, slow down and take a deep breath. It’s important to understand the past and present. But to be a successful investor, you’ll have to predict the future — a far bigger challenge than skimming through 10-Ks and listening to earnings calls. In other words, focus on examining not where the fundamentals and newsflow are, but where they may be going. Remember, when a guy on TV tells you a stock is good because it’s trading at X times earnings and has Y in cash on its balance sheet, he’s simply repeating the bare minimum of what the market knows. As men wiser than me have said, “What the market knows is not worth knowing.” 2. Timing Is Everything. When looking at the market,it’s important to understand not only “the what,” but “the why.” But the more I think about it, the more I’d argue that “the when” trumps both those considerations. Let me tell you a story. I once interviewed at a hedge fund that was making a major bet on its prediction that the then-growing housing bubble would implode. Smart money, right? However, that interview took place in early 2003, right before the Housing Index (^HGX) doubled. Likewise, a lot of folks were short FitBit (FIT) year as it crashed and burned from that $51.90 high hit last August. But a lot of bears got smashed on the 73% rally that precded the drop. So when you have an investment thesis in your mind, ask yourself, “What makes now the right time to bet on this?” Furthermore, if the S&P 500 is skyrocketing, it is entirely likely that junky companies rally big-time. Likewise, if the market’s in meltdown mode, even the best of the best can get smashed. Apple (AAPL) closed out 2007 at $198.08. But in 2008, even in the face of enormous earnings beats and the halo of the iPhone’s unprecedented success, Apple finished the year at $85.35 — a drop of 57%! You may be smart, but remember: Sometimes Mr. Market just does not care about what you think. 3. You Are Probably Suffering From Confirmation Bias. The Oxford Dictionaries defines confirmation bias as “the tendency to interpret new evidence as confirmation of one’s existing beliefs or theories.” Translated into financial terms, it means that if you’re bullish on gold (GLD), you interpret everything you see as bullish for gold. I know the power of confirmation bias from a horrible experience with a former tech highflier called Rackable Systems, which changed its name to SGI (SGI) after it acquired Silicon Graphics in 2009. In 2006, Rackable Systems was a momentum King — kind of like newer names like Acacia (ACIA). It was pulling in boatloads of money selling energy-efficient servers to major data-center operators like Microsoft (MSFT), Amazon, and Yahoo (YHOO). And then — let me point out that I had complete knowledge of this — competitors like Hewlett-Packard (HPQ) decided they wanted some of those data-center dollars. Maybe I should have imagined what would happen if Rackable lost Microsoft (34% of revenues) or Yahoo (26% of revenues) as a customer, or at the very least, the margin pressures that could be introduced in a more competitive server environment. However, I viewed the new competition as nothing less but confirmation that Rackable was on the right track. And then Rackable crashed from $56 to under $10 as earnings collapsed. It is impossible to stay perfectly objective when performing research. But you can stay one step ahead of your own bias by regularly asking the question, “Am I just telling myself what I want to hear?” 4. In Isolation, Valuation Ratios Are Useless. Investors often take a simplistic view of valuation ratios, automatically assuming that if something is “cheap,” it’s good, and if it’s “expensive,” it’s bad. But you’ll often see cheap stocks get cheaper and expensive stocks get more expensive. How many times has someone told you that Salesforce.com (CRM) is overpriced? Next, look at the stocks’ chart since it went public:   A P/E ratio, like every other valuation ratio, is 100% meaningless in isolation. It is far more important to examine how the “E” part of the equation is changing. (Or sales for EV/S ratios or EBITDA for EV/EBITDA ratios, etc.) A company trading at five times earnings can look awfully expensive following a bad quarter that destroys future earnings expectations. That’s how a stock like GoPro (GPRO) can go from $98 to $50 to $9 in the blink of an eye. It also works the other way around — a high-priced momentum stock can suddenly look cheap if earnings come in ahead of expectations and forward estimates rise.  

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