Index Active management, 117 , 125 –126, 150 capital allocation, relationship, 79 –81 volatility trading concept, 58 Active traders, 125 Active trading, 2 –3, 123 , 149 Advanced portfolio management, 3 , 133 , 149 advanced diversification, 149 –153 capital (balancing), POP (usage), 153 –156 market/underlying IV, consideration (absence), 156 portfolio construction, 156 –160 positions, POP‐weighting, 156 straddle, price, 181 strategy diversification, 151 American options, exercise, 7 Assets combination, 38 correlation history, 138t illiquid asset, 94 management, Kelly Criterion (application), 185 portfolio, trading, 137 rates, experience, 52t realized moves, IV overstatement, 46t trading, 94 , 173 –174 universe, selection, 94 –95 volatility, 31 weighting, POP (usage), 149 At‐the‐money (ATM) contract description, 9 positions, 33 straddle, 181 strikes, 32 closeness, 99 –100, 146 Autocorrelation, 26 Backtest period, usage, 158 Beta ( β ) beta‐weighted delta, 38 , 144 –145, 148 , 174 index, assumption, 145 metric, 38 Bid‐ask spread, 94 , 95t Binary events, 3 EMH, relationship, 164 examples, 163 option strategies, 166 –167 outcomes, predictability (absence), 164 premium, buying/selling result (evidence), 164 stock‐specific binary events, 156 trades, 166 –167, 175 volatility expansion, impact, 164 Black‐Scholes assumptions, usage, 44 –45 Black‐Scholes equation, 29 European‐style option price evolution, relationship, 23 Black‐Scholes model, 22 –31, 35 , 42 , 179 , 181t assumptions, 23 , 27 , 35 , 44 , 45 Brownian motion (Wiener process), relationship, 23 –26 geometric Brownian motion, relationship, 27 –28 mathematical definition, derivation, 111 mechanics, 30 options fair price, estimate, 30 , 42 price dynamics approximation, 24 Black‐Scholes option pricing formalism, impact, 22 –23 Black‐Scholes options pricing model, 44 –45 Black‐Scholes theoretical price range, 179 Brownian motion Black‐Scholes model, relationship, 23 –26 cumulative horizontal displacements, 24 –25, 25f particle, 2D position, 25f price dynamics, comparison, 25 –26 stock log‐returns, evolution, 179 Bullish directional exposure, 90t Buying power, allocation percentages, 154t Buying Power Reduction (BPR), 3 , 66 , 83 , 153 average BPR comparison, 110t , 113t calculation, 84 capital coverage, 89 requirement, correspondence, 85 –86 definition, variation, 84 historical effectiveness, 84 IV comparison, 66 inverse relationship, 87 loss percentage, 85f margin, contrast, 84 maximum per‐trade BPR, limitation, 134 option price, inverse correlation, 87 options, capital efficiency (relationship), 90 portfolio capital amount, 171 reduction, impact, 89 result, 87t short call/put BPR, 86 short strangle BPR, 86 stock margin, option counterpart, 84 undefined risk strategies, relationship, 84 underlying IV function/underlying price function, 88f understanding, importance, 90 usage, 83 , 89 variables, dependence, 85 –86 Call option, 7 , 9 strike prices, comparison, 114t trading level (determination), Black‐Scholes model (usage), 31 Call skew, 112 Call strikes, comparison, 111 –112 Capital balancing, POP (usage), 153 –156 requirement, BPR (correspondence), 85 –86 Capital allocation amounts, differences, 78f control, 81 efficiency, active management (relationship), 79 –81 estimate, risk‐free rate value (usage), 154 –155 guidelines, 133 , 152 , 155 , 156 maintenance, 149 , 173 market IV, impact, 76t violation, avoidance, 155 position sizing, relationship, 134 –136 positional capital allocation, quantitative approach, 153 preferences, 129 , 131 , 172 proportions, estimation, 155 risk management techniques, incorporation (impact), 158 scaling, 79 , 134 short premium capital allocation, scaling up, 76 undefined risk capital allocation, sharing, 110 undefined risk strategy, usage, 110 volatility trading concept, 58 Capital at risk (comparison), BPR (usage), 89 Casinos long‐run statistical advantage, 58 , 72 –73 options trading, 1 –2 CBOE volatility index. See Volatility index Central limit theorem, 20 , 72 , 166 , 170 , 178 Company exposure, 98 Company‐specific risk, 96 Company‐specific uncertainty, 43 Conditional probability, 183 –184 calculation, 184 usage, 142 Conditional value at risk (CVaR), 63 inclusion, 40f metric, 38 usage, 39 –40, 65 –66, 123 VaR, contrast, 40 Contract delta, 33 –35, 79 , 111 , 114 implied volatility (IV), equivalence, 87 risk, 172 Contract duration middle ground contract duration, 101 selection, 94 , 99 –102 trading, importance, 151 Contracts average daily P/L and average duration, 121t extrinsic value, decrease, 34 prices, differences, 42t Core positions, 134 P/L standard deviations, presence, 156 –157 Covariance correlation, relationship, 35 –38 measures, 37 negative covariance, 36 positive covariance, 35 Cumulative horizontal displacement, 25f Cumulative horizontal displacements, 24 Daily P/Ls, standard deviation, 150f Daily returns, distribution, 39f , 40f Days to expiration (DTE), management usage, 118 –120 Defined risk, selection, 102 –104 Defined risk strategies, 152 maximum loss, 102 BPR, usage, 84 limitation, 59 P/L targets, attainment, 153 POP, usage, 110 portfolio allocation, 103t risk, comparison, 89 selection, 94 short premium allocation, 173 stop losses, unsuitability, 173 undefined risk strategies, comparison, 102t , 109 avoidance, 110 Delta (Δ), 31 –32, 106t basis, 112 beta‐weighted delta, 38 , 144 –145, 148 , 174 contract delta, 33 –35, 79 , 111 , 114 implied volatility (IV), equivalence, 87 contract risk, 172 contract usage, 32 directional exposure measurement, 111 drift, 145 level, 114 magnitude, 32 , 114 negative delta/positive delta, 33 neutral position, 33 , 61 , 146 , 156 neutral positions profit, 111 normalization, 145 perceived risk measure, 112 –113 raw delta, comparisons (impossibility), 146 –147 re‐centering, 114 scaling up, 114 selection, 94 , 111 –115 optimum, factors, 114 sensitivity, 146 sign, 32 value, range, 32 Derivatives, gamma comparison (impossibility), 146 –147 Deterministic price trends, 28 –29 Dice rolls, histogram, 13 , 14f , 17f , 19f , 21f Directional assumption, selection, 94 , 104 –110 Directional exposure (measurement), delta (usage), 111 Directional risk, degree (measure), 32 Distributions asymmetry (measure), skew (usage), 65 mean (histogram), 17e normal distribution, 22f , 44 –45, 180f skew, 16 –18, 20 , 39 statistics, understanding, 21 –22 Diversification, 136 –144, 158 effectiveness, understanding, 137 –138 time diversification, 151 tools, 173 Dividends payment, avoidance, 23 Downside risk amount, preference, 104 limitation, absence, 102 Downside skew, 112 Early‐managed contracts, 126 , 129 occurrences allowance, 80 Early‐managed portfolio, losses, 129 Early‐management strategies, 80 Earnings dates, marking, 54f Earnings report, 115 dates, 53 , 96 , 102 impact, 43 inclusion, 163 quarterly earnings report (single‐company factors), 52 , 166 , 175 Efficient market hypothesis (EMH), 11 –13, 177 –178, 183 binary events, relationship, 164 forms, 11 –12, 104 –105 interpretation, 104 , 116 Equities implied volatility indexes, 54f pricing/bid‐ask spread/volume data, 95t trading, 137 , 140 European call options, 29 European options, expiration (payoff), 29 European‐style option (price evolution), Black‐Scholes equation (relationship), 23 Events outcomes, 44 –45 sampling, probability distribution (usage), 72 Exchange‐traded funds (ETFs), 5 –7, 36 , 157 BPR, historical effectiveness, 84 correlations, 157t diversification, 53 –54, 134 historical risk, approximation, 63 IV overstatement rates, 46 market ETFs, 139 –142, 145 , 157 volatility assets, correlation, 139 skewed returns distribution, 22 stability, 98 underlyings, 95 , 135 , 137 , 172 advantages/disadvantages, 96t losses, 84 , 171 strangles, usage, 156 usage, 97 volatility profiles, differences, 96 Expected move cones, 44 , 45f , 60f Expected move range, 179 Expected price range, 45f Expected range, 58 , 179 –183 adjustment, 68 –69 calculation, 43 –45, 47 , 179 , 181 estimates, 44 increase, 115 short strike prices, relationship, 111 tightness, 51 underlying price expected range, 60 –61 External events, outlier underlying moves/IV expansions (relationship), 58 Financial derivative, options (comparison), 7 Financial insurance, risk‐reward trade‐off, 47 Gamma ( Γ ), 31 , 33 comparison, impossibility, 146 –147 increase, 79 magnitude, 33 risk, 146 –147 Gaussian distribution (bell curve), 20 Geometric Brownian motion, Black‐Scholes model (relationship), 27 –28 GLD returns, SPY returns (contrast), 36f Greeks, 31 –35. See also Delta ; Gamma ; Sigma ; Theta assumptions, 35 balance, 148 option Greeks, 38 portfolio Greeks, 160 maintenance, 133 , 144 –147 risk measures, 174 Heteroscedasticity, 26 High implied volatility (high IV) short premium trading, 75 trading, 66 –72, 75 Histogram daily returns/prices, 27f dice rolls, 14f , 17f , 19f , 21f Historical distribution, 73f Historical P/L distribution, 62f , 64f , 71f Historical returns, standard deviation, 28 , 30 Historical tail risk, estimation, 65 Historical volatility, 21 –22, 38 increase, 42 market historical volatility, 69 representation, 43 stock historical volatility, 30 underlying historical volatility, 31 usage, 30 , 63 Historic risk, estimation, 21 –22 Horizontal displacements, distribution, 26f Hurricane insurance price, proportion, 47 sellers, strategic room, 47 –48 Idiosyncratic risk, 137 Illiquid asset, example, 94 Illiquidity risk, minimization, 171 Implied volatility (IV), 3 , 38 , 41 , 83 , 169 –170, 181 basis, 48 BPR comparison, 66 inverse volatility, 87 contract delta, equivalence, 87 contraction, 50 conversion, 66 correlation, 42 –43 decrease/increase, 42 –43, 87 , 89 derivation, 44 –45 differences, 42t environments, short option strategies (trading), 76 expansion, 58 , 122 –123, 163 indexes, 53f , 54f , 165f indication, 30 IV‐derived price range, 44 –45 long‐term baseline reversion, 52 metric, importance, 30 –31 overstatement, 46 , 46t , 164 profits, 58 rates, 47 peak, increase, 49 price range forecast, 47 ranges, 76t realized risk measurement, 46 reversion, 51 –54 signals, capacity, 51 source, 23 SPY annualized implied volatility (tracking), 48 SPY implied volatility, 69f standard deviation range, 43 tracking, 48 trading (volatility trading concept), 58 underlying IV, 60 , 86 , 88f usage, 41 , 134 Implied volatility percentile (IVP), 66 –68 Implied volatility rank (IVR), 68 Increments, distribution, 26f Insider trading, 12 , 105 In‐the‐money (ITM), 99 contract description, 9 ITM put, price, 10 long calls ITM, 33 movement, 34 –35 options, directional risk, 114 positions, 34 relationship, 32 Iron condors, 105 , 110t , 151 cap, long wings, 106 , 108 drawdowns, experience, 151 narrow wings, POP (presence), 109 neutral SPY strategies, 151 profit potential, 109 representation, 107f risk, 110 short iron condor BPR, 108 short iron condors, range, 134 , 173 statistical comparison, 109t underlying strangle, contrast, 171 wide iron condors, 116 , 172 wide wings, inclusion (trading), 109 wings, inclusion, 106 Kelly Criterion application, 185 buying power percentage, 153 derivation, 184 –186 formula, 186 heuristic derivation, 160 uncorrelated bets, 154 Law of large numbers, 72 , 170 , 185 Liquidity importance, understanding, 94 net liquidity, 89t options liquidity, 94 –95 portfolio net liquidity, 104 , 145 theta ratio/net portfolio liquidity, 145 Log‐normal distribution, 177 comparison, 180f skew, 179 stock prices, relationship, 179 Log returns equation, 7 standard deviation, 23 Long call, 32 , 34 addition, 106 directional assumption, 8t option, price, 32 , 111 P/L, 10 –11 position, 33 profit potential, 90 Long premium contracts, impact, 84 positions, profit yield (comparison), 12 strategies, 58 , 170 trade, 8 Long put, 32 , 34 addition, 106 directional assumption, 8t option, price, 111 P/L, 10 –11 position, 33 Long stock, 32 Long strikes, 207f Loss incurring, probability, 113t targets, 122t , 123 Low‐loss targets, attainment, 122 Management P/L target, usage, 120 –124 techniques, 123 –126, 152 timeline, usage, 118 –119 Management strategies, 121t , 122t , 158 average daily P/L and average duration, 121t impact/comparison, 79 –80, 80t , 102 long‐term risks, 126 , 129 performance, scenarios (impact), 126 qualitative comparison, 125t selection, 172 usage, 117 –118 Management time, selection, 119 , 129 Margin, BPR (contrast), 84 Market conditions, risk/return expectations, 35 exposure, 98 frictionlessness, 23 historical volatility, 69 implied volatility (IV), 76t , 152 perceived uncertainty, 46 trader beliefs, 171 –172 uncertainty sentiment, IV tracking, 48 volatility amounts, differences, 89t Market ETFs, 139 –142, 145 , 157 historic correlations, 141t , 143t percentage, 138t volatility assets, correlation, 139 Market risk sentiment, IV proxy, 42 sentiment, IV proxy (usage), 169 –170 Maximum per‐trade BPR, limitation, 134 Mean (moment), 14 –15 Middle ground contract duration, 101 Mid‐range stop loss, 123 , 130 , 173 Moments, 14 –22 Near‐the‐money options, gamma (increase), 79 Negative covariance, 36 Non‐dividend‐paying stock, trading, 30 –31 Non‐fungible tokens (NFTs), 5 Normal distribution comparison, 180f mean/standard deviation, 180f plot, 22f standard deviation range, 44 –45 Occurrences, 62f , 71f , 101 compound occurrences, loss potential, 142 concentration, 20 consistency, 117 density, 64 early‐managed contract allowance, 80 final P/L, correspondence, 61 goal, 125 –126, 151 increase, 117 P/L distribution, 39 reduction/increase, 72 , 89 , 124 standard deviation range, 64 VIX level, contrast, 67 Occurrences, number, 58 , 72 –76, 99 attainment, 99 compromise, absence, 151 increase, 81 , 101 –102, 118 presence, 15 , 126 , 129 trade‐off, 119 volatility trading concept, 58 Off‐diagonal entries, 141t Options, 5 –6 buying, profit, 57 –58 capital efficiency, BPR (relationship), 90 demand, 42 –43 fair price (estimation), Black‐Scholes model (usage), 30 , 42 financial derivative, comparison, 7 Greeks, 38 illiquidity, risk, 94 leverage, effects (clarity), 90 liquidity, 94 –95 market, liquidity, 98 P/L standard deviation, usage, 73 P/L statistics, 97t price, BPR (inverse correlation), 87 profitability, 10 risk, visualization, 59 –63 traders, assumptions, 11 types, 7 underlyings, sample, 98t Options trading, 84 , 97 , 102 , 169 , 175 casinos, usage, 1 –2 diversification, importance, 136 ETF underlyings, usage, 97 gamma, awareness (importance), 33 implied volatility metric, 30 –31 reversion, 51 learning curve/math knowledge, 3 option theory, transition, 90 profitability, option pricing (impact), 11 quantitative options trading, 3 retail options trading, assets (suitability), 94 risk management, relationship, 2 usage, market performance, 12 Outlier losses, 142 capital exposure, limitation, 134 probability, 141t Outlier risk carrying, avoidance, 103 reduction, 76 Out‐of‐the‐money (OTM) contract description, 9 positions, 34 volatility curve, 182f Over‐the‐counter (OTC) options, 7 Passive investment, daily performance statistics, 146t Passive traders, 125 Perceived risk (measurement), delta (usage), 112 –113 Personal profit goals, 171 –172 Per‐trade allocation percentage, 158t Per‐trade standard deviation, 158 , 166 Per‐trade statistics, differences, 166 Per‐trade variance, 167 P/L targets, attainment, 153 Portfolio averages, variance, 74f backtest performance statistics, 159t concentration excess, avoidance, 77 construction, 12 , 156 –160 cumulative P/L, 152f delta skew, 145 expected loss, CVaR estimate, 40 Greeks, 149 , 160 maintenance, 133 , 144 –147 net liquidity, 89t , 104 , 146 passive investment, daily performance statistics, 146t performance, 159f comparison, 139f P/L averages, 74f POP‐weighted portfolio, 157 –158 risk management, diversification tools, 173 statistical analysis, 153t Portfolio allocation, 109 defined/undefined risk strategies, 103t guidelines, usage, 89 , 104 , 134 percentages, 137 –138, 138t , 154 , 154t position sizing, relationship, 75 –79 scaling, 77 , 156 strategies, comparison, 77 usage, 103 volatility trading concept, 58 Portfolio buying power, 83 , 89 , 134 allotment/allocation, 134 –135, 154 –155, 157 defined risk position occupation, 118 expected profit, 146 undefined risk strategy occupation, 110 usage, 99 , 109 , 117 Portfolio capital allocation control, 81 guidelines, market IV (impact), 76t amount, BPR (relationship), 171 diversification, 152 investment, 127f , 128f Portfolio management, 3 , 93 , 149 back‐of‐the‐envelope tactics, 133 beta ( β ) metric, importance, 38 capital allocation, 134 –136 capital balancing, POP (usage), 153 –156 concepts, 133 construction, 156 –160 diversification, usage, 136 –144, 149 –153 portfolio Greeks, maintenance, 144 –147 position sizing, 134 –136 simplification, 101 Positional capital allocation, quantitative approach, 153 Positions core position statistics, 158t delta drift, 145 delta level, 114 expected loss, CVaR estimate, 40 intrinsic value, 9 ITM, relationship, 32 long side/short side, adoption, 8 management, 118 P/L correlation, reduction, 150 POP‐weighting, 156 profiting, likelihood, 104 sizing capital allocation, relationship, 134 –136 portfolio allocation, relationship, 75 –79 volatility trading concept, 58 Positive covariance, 35 Premium sellers, profit, 50 Premium, trading, 172 Price dynamics Black‐Scholes model approximation, 24 Brownian motion, comparison, 25 –26 Price predictability (limitation), EMH implications, 105 Probabilistic system, probability distribution, 14 Probability distribution, 13 –22 asymmetry, 16 events sampling, 72 Gaussian distribution (bell curve), 20 mean (moment), 14 –15 normal distribution, 20 skew (moment), 16 –22 variance (moment), 15 –16 Probability of profit (POP), 89 , 164 , 185 asset weighting, 149 buying power, allocation percentages, 154t capital, balancing, 153 –156 decrease, 114 dependence, 77 heuristic, 160 IV ranges, 76t level, elevation, 61 , 90 , 105 , 108 –109, 120 , 123 –124, 151 percentage, 62 , 73 , 109 POP‐weighted allocation, 158 POP‐weighted portfolio, 157 –158, 159t POP‐weight scaling method, 156 positions, POP‐weighting, 156 profit potential, differences, 103 selection, 2 statistics, 80t , 97t , 153t trade‐off, 63 trades, level (elevation), 134 usage, 110 , 149 , 153 , 185 –186 weights, usage, 155 yield, 121 Product indifference, 97 –98 Profitability, considerations, 8t Profit and loss (P/L) average daily P/L, 121t average P/L, 76t , 164 averages, 74f cumulative P/L, 152f daily P/Ls, standard deviation, 150f distribution skew, 62 –63 expectations, 135 frequency, 124 historical distribution, 73f historical P/L distribution, 62f , 64f , 71f IV ranges, 76t per‐day standard deviation, 150 standard deviation, 134 , 153t , 157 carrying, 120 –121 core position usage, 156 –157 reduction, 118 –119, 122 , 126 trade‐offs, 124 usage, 63 –65, 74 –75, 80t , 99 , 100t , 123 swings, 79 , 97 magnitude, 98 tolerance, 97 –98 Profit potential, POP differences, 103 level, elevation, 151 Profit targets, 104 , 120t , 123 Put options, 9 Put prices, differences, 98t Put skew, 112 Puts (option type), 7 QQQ returns, SPY returns (contrast), 36f , 37 strangles, outlier losses, 142 Quantitative options trading, 3 Quarterly earnings report (single‐company factors), 52 , 166 , 175 Random variable, probability distribution, 13 Realized moves, IV overstatement, 46t Realized risk (measurement), IV (usage), 46 Realized volatility, IV overstatement, 46 Reference index, usage, 144 Relative volatility, metrics, 66 –68 Retail options trading, assets (suitability), 94 Returns distributions skews, 22 past volatility/future volatility, 43 standard deviation, 21 –22 usage, 63 Risk approximation, 30 categories, 137 measures, 38 –40 minimization, liquidity (impact), 95 reduction, trade‐by‐trade basis, 117 sentiment, measure, 30 –31 tolerances, 171 –172 trade‐off, 12 Risk‐free rate, 29 approximation, 154 value, usage, 154 –155 Risk management, 2 –3, 37 , 140 , 156 importance, 51 strategy/technique, 136 , 151 , 158 , 174 Risk‐reward trade‐off, 59 Sector exposure, 98 Sector‐specific risk, 96 Sell‐offs 2020 sell‐off, performances (2017‐2021), 78f volatility conditions, 164 Semi‐strong EMH, 12 , 104 –105 Short call, 32 , 34 addition, 147 , 175 BPR, 86 directional assumption, 8t P/L, 10 –11 position, 33 removal, 175 short put, pairing, 33 strike, 60 undefined risk, 59 Short‐call/put BPR, 86 Short iron condors, range, 134 , 173 Short options P/L distribution skew, 63 trading, capital requirements, 90 Short option strategies, 106t profitability, factors, 170 trading, 76 , 170 Short premium allocation, 173 capital allocation, scaling up, 76 positions, losses (unlikelihood), 170 risk (evaluation), BPR (usage), 83 strategies, POP trade‐off, 63 traders, profit, 51 Short premium trading, 48 , 114 benefits, 68 implied volatility elevation, impact, 71 importance, 59 mechanics, 57 risk‐reward trade‐off, 59 Short put, 34 addition, 147 , 174 –175 BPR, 86 bullish strategy, 32 directional assumption, 8t position, 33 removal, 175 strike, 60 Short strangles, POP level (elevation), 61 Short strike prices, expected range (relationship), 111 Short volatility trading, 83 Sigma ( σ ), 15 Single‐company factors, 52 –53 Single company risk factors, impact, 46 Skew, 68 amount, consideration, 71 contextualization, 65 distribution skew, 16 –18, 20 , 39 log‐normal distribution skew, 179 magnitude, decrease, 72 moment, 16 –22 P/L distribution skew, 62 –63 portfolio delta skew, 145 pure number, 17 reduction, 71 –72 returns distribution skews, 22 strike skew, 111 –112, 179 –183 tail skew, usage, 39 usage, 65 –66 volatility skew (volatility smirk), 181 SPDR S&P 500 (SPY) annualized implied volatility, tracking, 48 daily returns distribution, 39f , 40f expected move cone, 45f expected price ranges, 44 histogram, daily returns/prices, 27f implied volatility (IV), 69f , 70f iron condors, wings (inclusion), 107t –110t neutral SPY strategies, 151 price, 112f change, 60f , 78f trends, 24 returns, QQQ/TLT/GLD returns (contrast), 36f , 37 trading level, 183 SPDR S&P 500 (SPY) strangles, 64f , 73f BPR loss, 85f data (2005‐2021), 88f , 89t deltas (differences), statistical comparison, 113t durations, differences, 183t example, 107t initial credits, 108t management statistics, 119t , 120t , 122t , 124t , 125t strategies, comparison, 80t outlier losses, 142 P/L per‐day standard deviation, 150 stability, 63 VIX level labeling, 69f Standard deviation, 20 –21 daily P/Ls, standard deviation, 150 estimates, 16 expected move range, 179 expected range, 60 strikes, correspondence, 183 histogram, 17f historical returns, standard deviation, 28 , 30 indication, 16 interpretation, 18 –19, 64 –65 log returns, standard deviation, 23 normal distribution usage, 180f per‐trade standard deviation, 158 , 166 P/L per‐day standard deviation, 150 P/L standard deviation, 63 –65, 74 –75, 80t , 99 , 100t , 134 , 153t , 157 carrying, 120 –121 reduction, 118 –119, 122 , 126 trade‐offs, 124 usage, 123 probabilities, 22f range, sigma ( σ ), 37 , 43 –45, 64 –65 representation, 15 returns, standard deviation, 21 –22 sigma ( σ ), 15 usage, 63 –65 Steady‐state value, 48 Stocks, 5 –6 historical risk, approximation, 63 historical volatility, 30 IV overstatement rates, 46 liquidity, 94 –95 log returns, 23 options, trading, 96 –97 prices differences, 98t log‐normal distribution, relationship, 179 skewed returns distributions, 22 stock‐specific binary events, 156 trading, 90 , 179 margin, usage, 84 underlyings advantages/disadvantages, 96t trading, 135 volatility profiles, differences, 96 Stop loss, 122 application, 129 implementation, 122 , 130 , 173 mid‐range stop loss, 123 , 130 , 173 threshold, usage, 122 –123 usage, 123 –125 Straddles ATM straddle, price, 181 trades, BPR result, 87t Strangles, 105 buyer assumption, 61 drawdowns, experience, 151 durations, differences, 101t magnitude, 65 management strategies, 123 neutral SPY strategies, 151 P/L distributions, skew/tail losses, 71 –72 sale, BPR requirement, 86 seller, profit, 61 short strangle BPR, 86 statistics, 167t management, 122t , 136t trades, examples, 87t trading, effects, 142 usage, 156 Strategy‐specific factors, 152 –153 Strike skew, 111 –112, 179 –183 Strikes long strikes, 107f prices, comparison, 114t range, 104 standard deviation, expected range (correspondence), 183 Strong EMH, 12 , 104 –105 Supplemental positions, 134 Swaptions, 5 Systemic risk, 137 Tail exposure limitation, capital allocation guidelines (maintenance), 173 magnitude, 98 Tail losses CVaR sensitivity, 40 reduction, 71 –72 Tail risk, 83 , 103 , 121 , 145 acceptance, 57 carrying, 58 , 62 , 120 elimination, 122 –123 exposure, 102 , 135 historical tail risk, estimation, 65 increase, 97 , 108 –109, 119 inherent tail risk, justification, 121 mitigation, 135 –136 negative tail risk, 65 , 72 , 80 Tail skew, usage, 39 Theta ( Θ ), 31 , 34 , 144 , 174 additivity, 145 –147 ratio, size (reaction), 147 theta ratio/net liquidity, 174 theta ratio/net portfolio liquidity, 145 Time diversification, 151 TLT returns, SPY returns (contrast), 36f Trade‐by‐trade basis, 79 –80, 117 , 125 –126 Trade‐by‐trade performance, comparison, 118 Trade‐by‐trade risk tolerances, 119 –120 Trades BPR, 98 bullish directional exposure, 90t management, 3 , 80 –81, 117 –118 strategies, usage, 101 maximum loss, reduction, 108 Trades, construction, 93 asset universe, selection, 94 –95 contract duration, selection, 99 –102 defined risk, selection, 102 –104 delta, selection, 111 –115 directional assumption, selection, 104 –110 procedure, 94 undefined risk, selection, 102 –104 underlying, selection, 96 –98 Trading engagement, preferences, 124 mechanics, 48 platforms, usage, 179 , 181 strategies, 129 , 166 Uncertainty sentiment, IV tracking, 48 Undefined risk capital allocation, sharing, 110 selection, 102 –104 Undefined risk strategies, 59 , 152 BPR, relationship, 84 , 103 defined risk strategies, comparison, 102t , 109 avoidance, 110 downside risk, limitation (absence), 102 gain, limitation, 84 loss, limitation (absence), 59 , 84 management, focus, 118 P/L targets, attainment, 153 portfolio allocation, 103t risk, comparison, 89 selection, 94 short premium allocation, 173 trader compensation, 103 Underlying historical volatility, 31 increase, 42 implied volatility (IV), 98 option underlyings, sample, 98t selection, 94 , 96 –98 strangle, iron condor (contrast), 171 Underlying price BPR function, 88f expected range, 60 –61, 181t Upside skew, 112 Value at risk (VaR). See Conditional value at risk CVaR, contrast, 40 distribution statistic, 39 inclusion, 39f , 40f Variance moment, 15 –16 per‐trade variance, 166 –167 Volatility curve, 182 expansions, 50 –51 forecast, 43 realized volatility, IV overstatement, 46 reversion, 105 smile, 179 –183 smirk (volatility skew), 181 trading, 41 , 44 –48, 58 Volatility assets, market ETFs (correlation), 139 Volatility index (VIX) (CBOE volatility index), 51 , 60 , 78f 2008 sell‐off, 50 , 63 2020 sell‐off, 50 , 63 , 77 , 78f comparison, 89 contraction, 50 contracts, acceleration, 49 correlations, 141t expansion, 48 increase, 54 IVP labeling, 67f levels, 127f , 128f differences, 103t SPY strangles, labeling, 69f long‐term average, 67 , 69 long‐term behavior, 66 lull/expansion/contraction, 49 occurrences, relationship, 71f phases, 49f range, 48 , 66 , 72 , 171 reduction/increase, 69 , 134 frequency, 75t spikes, causes, 50 states, 48 –51 valuation, 135 VXAZN IVP values labeling, 67f level, 66 Weak EMH, 11 , 29 , 31 , 104 –105 Wide iron condors, 116 , 172 Wide wings, usage, 109 Wiener process, 29 Black‐Scholes model, relationship, 23 –26 increments, distribution, 26f Wings, 105