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An approachable guide to sustainable options trading, minimal luck needed.
Traders who are successful long-term do not rely on luck, but rather their ability to adapt, strategize, and utilize available tools and information. Modern markets are becoming increasingly accessible to the average consumer, and the emergence of retail options trading is opening a world of opportunities for the individual investor. Options are highly versatile and complex financial instruments that were exclusive to industry professionals until recently. So where should beginners start? The Unlucky Investor's Guide to Options Trading breaks down the science of options trading to suit interested traders from any background. Using statistics and historical options data, readers will develop an intuitive understanding of the potential risks and rewards of options contracts. From the basics of options trading to strategy construction and portfolio management, The Unlucky Investor's Guide to Options Trading guides readers through the world of options and teaches the crucial risk management techniques for sustainable investing.
JULIA SPINA is a member of the research team and podcast co-host at tastytrade where she works as a financial educator and options strategist. Drawing from her background in physics and experience with signal processing and data analysis, Julia introduces viewers to topics in quantitative finance and their applications in options strategy development. At the University of Illinois, she earned bachelor's degrees in engineering physics (2017) and applied mathematics (2017) and a master's in physics (2018).
TOM SOSNOFF is an online brokerage innovator, financial educator, and the founder and co-CEO of tastytrade. Tom is a serial entrepreneur who cofounded thinkorswim in 1999, tastytrade in 2011, tastyworks in 2017, helped to launch Luckbox magazine in 2019, and in 2020 created the first new futures exchange in 20 years, The Small Exchange. Currently, Tom hosts tastytrade LIVE and continues to drive 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.
Foreword ix
Preface xiii
Acknowledgments xv
About the Authors xvii
Introduction: Why Trade Options? 1
Chapter 1: Math and Finance Preliminaries 5
Chapter 2: The Nature of Volatility Trading and Implied Volatility 41
Chapter 3: Trading Short Premium 57
Chapter 4: Buying Power Reduction 83
Chapter 5: Constructing a Trade 93
Chapter 6: Managing Trades 117
Chapter 7: Basic Portfolio Management 133
Chapter 8: Advanced Portfolio Management 149
Chapter 9: Binary Events 163
Chapter 10: Conclusion and Key Takeaways 169
Appendix 177
Glossary 187
References 193
Index 195
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.
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 relative to the number of outstanding shares.
An exchange-traded fund (ETF) is a basket of securities, such as stocks, bonds, or commodities. Like stocks, shares of ETFs are traded publicly on stock exchanges. Similar to mutual funds, these instruments represent a fraction of ownership of a diversified portfolio that is usually managed professionally. These assets track aspects of the market such as an index, sector, industry, or commodity. For example, SPDR S&P 500 (SPY) is a market index ETF tracking the S&P 500, Energy Select Sector SPDR Fund (XLE) is a sector ETF tracking the energy sector, and SPDR Gold Trust (GLD) is a commodity ETF tracking gold. ETFs are typically much cheaper to trade than the individual assets in an ETF portfolio and are inherently diversified. For instance, a share of stock for an energy company is subject to company-specific risk factors, while a share of an energy ETF is diversified over several energy companies.
When assessing the price dynamics of a stock or ETF and comparing the dynamics of different assets, it is common to convert price information into returns. The return of a stock is the amount the stock price increased or decreased as a proportion of its value rather than a dollar amount. Returns can be scaled over any time frame (daily, monthly, annual), with calculations typically calling for daily returns. The two most common types of returns are simple returns, represented as a percentage and calculated using Equation (1.1), and log returns, calculated using Equation (1.2). The logarithm's mathematical definition and properties are covered in the appendix for those interested, but that information is not necessary to know to follow the remainder of the book.
where is the price of the asset on day and is the price of the asset the prior day. For example, an asset priced at $100 on day 1 and $101 on day 2 has a simple daily return of 0.01 (1%) and a log return of 0.00995. Simple and log returns have different mathematical characteristics (e.g., log returns are time-additive), which impact more advanced quantitative analysis. However, these factors are not relevant for the purposes of this book because the difference between log returns and simple returns is fairly negligible when working on daily timescales. Simple daily returns are used for all returns calculations shown.
An option is a type of financial derivative, meaning its price is based on the value of an underlying asset. Options contracts are either traded on public exchanges (exchange-traded options) or traded privately with little regulatory oversight (over-the-counter [OTC] options). As OTC options are nonstandardized and usually inaccessible for retail investors, only exchange-traded options will be discussed in this book.
An option gives the holder the right (but not the obligation) to buy or sell some amount of an underlying asset, such as a stock or ETF, at a predetermined price on or before a future date. The two most common styles of options are American and European options. American options can be exercised at any point prior to expiration, and European options can only be exercised on the expiration date.1 Because American options are generally more popular than European options and offer more flexibility, this book focuses on American options.
The most basic types of options are calls and puts. American calls give the holder the right to buy the underlying asset at a certain price within a given time frame, and American puts give the holder the right to sell the underlying asset. The contract parameters must be specified prior to opening the trade and are listed below:
Note that the price of the option is commonly denoted as C for calls, P for puts, and V if the type of contract is not specified. Options traders may buy or sell these contracts, and the conditions for profitability differ depending on the choice of position. The purchaser of the contract pays the option premium (current market price of the option) to adopt the long side of the position. This is also known as a long premium trade. The seller of the contract receives the option premium to adopt the short side of the position, thus placing a short premium trade. The choice of strategy corresponds to the directional assumption of the trader. For calls and puts, the directional assumption is either bullish, assuming the underlying price will increase, or bearish, assuming the underlying price will decrease. The directional assumptions and scenarios for profitability for these contracts are summarized in the following table.
Table 1.1 The definitions, conditions for profitability, and directional assumptions for long/short calls/puts.
Profits increase as the price of the underlying increases above the strike price .
Directional assumption: Bullish
Profits increase as the price of the underlying decreases below the strike price .
Directional assumption: Bearish
The relationship between the strike price and the current price of the underlying determines the moneyness of the position. This is equivalently the intrinsic value of a position, or the value of the contract if it were exercised immediately. Contracts can be described as one of the following, noting that options cannot have negative intrinsic value:
The intrinsic value of a position is based entirely on the type of position and the choice of strike price relative to the price of the underlying:
For example, consider a 45 DTE put contract with a strike price of $100:
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