regardedtrading.art

What you’ll learn

16 short chapters. How listed equity options work: the contract, premium, the Greeks, IV crush and spreads; what happens at expiration and the morning after; then the short side: covered calls, the wheel, the expected move and sizing. Three acts. The first chapter of each is free.

Act I

Read the Chain

01Call and put optionsFREEWhat a call and a put are: strike, expiration and premium, why one US equity contract is 100 shares, and why a long option can only lose what you paid.02Intrinsic and extrinsic option valueHow an option’s premium splits into intrinsic value and extrinsic value, and why an out-of-the-money call can still change price before it expires.03Option delta and thetaDelta, the option’s sensitivity to the stock, and theta, the daily cost of time. Why a small premium can behave like a large share position.04Implied volatility and IV crushImplied volatility is the move already priced into an option. After earnings that uncertainty collapses, and a call can lose money even when the stock rises.05Option spreads and defined riskBull call spreads and credit put spreads cap both the gain and the loss. A naked short option does not, which is how an account gets taken.★Reading a 0DTE options chainCase: a same-day chain at 3pm. Price a nickel call against a defined-risk spread, and see what the stock must do before the close.
Act II

Expiration Day

06Option exercise and assignmentFREEExercise versus selling to close, how assignment is handed out, why an option one cent in the money at the close becomes 100 shares, and the dividend that triggers early assignment.07Option bid-ask spreadBid, ask and mid, what a round trip really costs, market versus limit orders, volume versus open interest, and why far strikes and same-day quotes are so wide.08Option gammaGamma, the speed at which delta changes, why it peaks at the money on expiration day, how a 0DTE option can double or vanish in an hour, and pin risk for a short strike.09Cash-settled index optionsCash vs. physical settlement, why SPX options pay cash and SPY options deliver shares, AM-settled monthly SPX vs. PM-settled SPXW, and the Section 1256 60/40 tax rule.★Options expiration and assignment riskA bull call spread held through expiration: the long leg exercises, the short one expires, and Monday brings 200 shares, a Reg T margin call and a loss past the spread’s max.
Act III

Theta Gang

10Covered call optionsFREEA covered call sells a call against 100 shares you own: premium now, upside capped at the strike, the stock’s downside kept. Max profit, breakeven and when shares get called away.11Cash-secured puts and the wheel strategySelling a put with the cash to buy the shares: the premium, the cost basis if assigned, how it differs from a naked put, and the wheel that turns assignments into covered calls.12Options expected move and vegaThe at-the-money straddle prices the move the market expects by expiration. Straddle breakevens, vega, who is long or short volatility, and why selling the move wins often and loses big.13Options position sizing and expected valueBreak-even win rates, expected value, what paying the ask costs, why a streak of losses ruins a large position and not a small one, and the gain it takes to climb out of a drawdown.★Selling options into earningsCase: sell a put into earnings. Read the expected move, size a cash-secured put against a credit spread, take a gap past the priced-in move, and pick the covered call that turns the wheel.

Glossary of every term in the course →

More courses

Read a business on balancesheet.art → Balance sheets, earnings reports and how to tell a good investment from a bad one.

Read the curve on basispoints.art → Coupons, yields, duration, credit spreads and the yield curve, how a bank full of safe bonds can still fail, and how the next one hedges.

Read the deal on cookedbooks.art → Price a company, fund the buyout, then open the data room and find out what the seller’s numbers were hiding.