and co‐CEO of tastytrade. Tom is a serial entrepreneur who cofounded thinkorswim in 1999, tastytrade in 2011, tastyworks in 2017, helped to launch the award‐winning Luckbox magazine in 2019, and in 2020 created the first new futures exchange in 20 years, The Small Exchange. Leveraging more than 20 years of experience as a CBOE market maker, Tom is driven by the passion to educate self‐directed investors. After his years on the trading floor, he saw the need to build and design superior software platforms and brokerage firms that specialized in complex financial strategies. His efforts ultimately changed the way options and futures are traded and how digital financial media is produced and consumed. Currently, Tom hosts tastytrade LIVE and continues to drive innovation and know‐how for the do‐it‐yourself investor. Tom has been named to Techweek's Tech 100 list, Crain's Chicago Business's Tech 50, and has spoken at more than 500 events across the globe. Tom received the Ernst & Young Entrepreneur of the Year Award and has been featured by prominent publications such as the The Wall Street Journal, Investor's Business Daily, Chicago Tribune, Crain's Chicago Business, Traders Magazine, and Barron's.
Introduction: Why Trade Options?
The house always wins. This cautionary quote is certainly true, but it does not tell the entire story. From table limits to payout odds, every game in a casino is designed to give the house a statistical edge. The casino may take large, infrequent losses at the slot machines or small, frequent losses at the blackjack table, but as long as patrons play long enough, the house will inevitably turn a profit. Casinos have long relied on this principle as the foundation of their business model: People can either bet against the house and hope that luck lands in their favor or be the house and have probability on their side.
Unlike casinos, where the odds are fixed against the players, liquid financial markets offer a dynamic, level playing field with more room to strategize. However, similar to casinos, a successful trader does not rely on luck. Rather, traders' long‐term success depends on their ability to obtain a consistent, statistical edge from the tools, strategies, and information available to them. Today's markets are becoming increasingly accessible to the average person, as online and commission‐free trading have basically become industry standards. Investors have access to an almost unlimited selection of strategies, and options play an interesting role in this development. An option is a type of financial contract that gives the holder the right to buy or sell an asset on or before some future date, a concept that will be explained more in the following chapter. Options have tunable risk‐reward profiles, allowing traders to reliably select the probability of profit, max loss, and max profit of a position and potentially profit in any type of market (bullish, bearish, or neutral). These highly versatile instruments can be used to hedge risk and diversify a portfolio, or options can be structured to give more risk‐tolerant traders a probabilistic edge.
In addition to being customizable according to specific risk‐reward preferences, options are also tradable with accounts of nearly any size because they are leveraged instruments. In the world of options, leverage refers to the ability to gain or lose more than the initial investment of a trade. An investor may pay $100 for an option and make $200 by the end of the trade, or an investor may make $100 by selling an option and lose $200 by the end of the trade. Leverage may seem unappealing because of its association with risk, but it is not inherently dangerous. When misused, leverage can easily wreak financial havoc. However, when used responsibly, the capital efficiency of leverage is a powerful tool that enables traders to achieve the same risk‐return exposure as a stock position with significantly less capital.
There is no free lunch in the market. A leveraged instrument that has a 70% chance of profiting must come with some trade‐off of risk, risk which may even be undefined in some cases. This is why the core principle of sustainable options trading is risk management. Just as casinos control the size of jackpot payouts by limiting the maximum amount a player can bet, options traders must control their exposure to potential losses from leveraged positions by limiting position size. And just as casinos diversify risk across different games with different odds, strategy diversification is essential to the long‐term success of an options portfolio.
Beyond the potential downside risk of options, other factors can make them unattractive to investors. Unlike equities, which are passive instruments, options require a more active trading approach due to their volatile nature and time sensitivity. Depending on the choice of strategies, options portfolios should be monitored anywhere from daily to once every two weeks. Options trading also has a fairly steep learning curve and requires a larger base of math knowledge compared to equities. Although the mathematics of options can easily become complicated and burdensome, for the type of options trading covered in this book, trading decisions can often be made with a selection of indicators and intuitive, back‐of‐the‐envelope calculations.
The goal of this book is to educate traders to make personalized and informed decisions that best align with their unique profit goals and risk tolerances. Using statistics and historical backtests, this book contextualizes the downside risk of options, explores the strategic capacity of these contracts, and emphasizes the key risk management techniques in building a resilient options portfolio. To introduce these concepts in a straightforward way, this book begins with discussion of the math and finance basics of quantitative options trading (Chapter 1), followed by an intuitive explanation of implied volatility (Chapter 2) and trading short premium (Chapter 3). With these foundational concepts covered, the book then moves onto trading in practice, beginning with buying power reduction and option leverage (Chapter 4), followed by trade construction (Chapter 5) and trade management (Chapter 6). Chapter 7 covers essential topics in portfolio management, and Chapter 8 covers supplementary topics in advanced portfolio management. Chapter 9 provides a brief commentary on atypical trades (Binary Events). The book concludes with a final chapter of key takeaways (Chapter 10) and an appendix of mathematical topics.
Chapter 1
Math and Finance Preliminaries
The purpose of this book is to provide a qualitative framework for options investing based on a quantitative analysis of financial data and theory. Mathematics plays a crucial role when developing this framework, but it is predominantly a means to an end. This chapter therefore includes a brief overview of the prerequisite math and financial concepts required to understand this book. Because this isn't in‐depth coverage of the following topics, we encourage you to explore the supplemental texts listed in the references section for those mathematically inclined. Formulae and their descriptions are included in several sections for reference, but they are not necessary to follow the remainder of the book.
Stocks, Exchange‐Traded Funds, and Options
From swaptions to non‐fungible tokens (NFTs), new instruments and opportunities frequently emerge as markets evolve. By the time this book reaches the shelf, the financial landscape and the instruments occupying it may be very different from when it was written. Rather than focus on a wide range of instruments, this book discusses fundamental trading concepts using a small selection of asset classes (stocks, exchange‐traded funds, and options) to formulate examples.
A share of stock is a security that represents a fraction of ownership of a corporation. Stock shares are normally issued by the corporation as a source of funding, and these instruments are usually publicly traded on stock exchanges, such as the New York Stock Exchange (NYSE) and the Nasdaq. Shareholders are entitled to a fraction of the company's assets and profits based on the proportion of shares they own
