Learn to trade options
from first principles.

Calendar Spreads Part 1: What They Are and Why They Work

A deep dive into calendar spreads — the options structure that sells near-term theta decay while buying longer-dated time value, benefits from rising implied volatility via vega asymmetry, and exploits the shape of the volatility term structure. Includes Greeks profile, tent-shaped P&L mechanics, key terminology, and the reason this was the #1 Sharpe strategy across all four market regimes in a 20-year, 1-million-trade S&P 500 backtest.

Calendar Spreads Part 2: Selecting Strikes, Expirations, and Building the Position

How to construct a calendar spread from scratch — covering ATM vs OTM strike selection, front-month and back-month DTE targets, calls vs puts, cost basis calculation, and position sizing with numeric examples throughout.

Calendar Spreads Part 3: Three Example Trades — Setup, Management, and Result

Three concrete calendar spread trade walkthroughs — a clean theta-harvest on SPY, an earnings-adjacent trade gone wrong, and a CRISIS-regime trade during the 2020 selloff — with full entry/exit and P&L

Calendar Spreads Part 4: Managing the Position — Rolling, Adjusting, and Responding to Moves

How to actively manage a calendar spread through delta drift, IV changes, and adverse moves — covering the roll mechanics, when to defend vs accept the loss, and the Greeks-based decision framework.

Calendar Spreads Part 5: When and How to Exit — Profit Targets, Stop Losses, and Converting to a Diagonal

The complete exit framework for calendar spreads — profit targets by regime, the 50% loss stop rule, how to close both legs efficiently, and when converting to a diagonal makes sense

Options Trading Part 1: Fundamentals — Contracts, Terminology, and the Four Basic Positions

A practical introduction to options contracts covering calls and puts, key terminology like strike, premium, and moneyness, the four basic trading positions, and how premium is priced — highlighting the importance of implied volatility and theta decay in options trading with a discussion of statistical considerations and limitations.

Options Trading Part 2: The Greeks — Delta, Gamma, Theta, Vega, and How They Drive P&L

A deep dive into the four primary options Greeks — delta, gamma, theta, and vega — covering what each measures, how they interact, the gamma/theta tradeoff at the core of every options position, and the most common Greek-related mistakes traders make around earnings and expiration.

Options Trading Part 3: Implied Volatility — What It Is, How It's Priced, and Where Edge Lives

IV vs historical volatility, the volatility risk premium, IV rank and percentile, skew, term structure, VIX levels, IV crush mechanics, and a practical checklist for reading volatility before every trade.

Options Trading Part 4: Core Strategies — Covered Calls, Spreads, Straddles, and More

The complete guide to income strategies (covered calls, cash-secured puts, the wheel), spread strategies (bull/bear debit and credit spreads, iron condor), and volatility strategies (straddles, strangles) — with full P&L tables, breakevens, and a decision matrix.

Options Trading Part 5: Trade Selection — Building a Position Around a Thesis, Not a Structure

How to select the right strike, expiration, and options structure by starting from a precisely defined thesis — covering delta targets for buyers and sellers, the 30–45 DTE sweet spot, IV rank as a structure filter, and a pre-trade checklist for every position.

Options Trading Part 6: Risk Management — Position Sizing, Exits, and Surviving as a Portfolio

The final installment of the options trading series covers what happens after entry: sizing by notional exposure, the 50% profit target and 2× loss limit rules for credit sellers, when and how to roll positions, portfolio-level delta and vega management, and the complete series summary.