The Position Desk

Options Overlay · ships with the paid letter

The same trade, expressed in options.

Position trades run for weeks to months — exactly the horizon where long-dated options become a serious alternative to stock. Each pick in the letter will carry an optional second line: a defined-risk option expression of the same thesis, sized to the same dollar risk.

Why options fit this system

  • The horizon matches. Multi-week holds make 4–6+ month expiries practical — enough runway that the trade, not the clock, decides the outcome.
  • Risk is defined by construction. A long call can never lose more than its premium — no gap through a stop, no overnight surprise beyond what you paid.
  • Capital works harder. A deep in-the-money call controls the same upside with a fraction of the capital, freeing the rest — or keeping total exposure honest in a small account.

How the overlay is built

  • Deep in the money, far out in time. The default expression is a high-delta call (≈0.7–0.8) four to six-plus months out — it moves nearly one-for-one with the stock and keeps the time-decay bill small relative to intrinsic value.
  • Same risk budget as the stock line. The position is sized so the realistic loss — premium at risk down to the stop scenario — matches the dollar risk of the share version. Never “cheap lottery tickets, lots of them.”
  • Spreads when volatility is rich. Recovery names often carry elevated implied volatility — the very surge that qualifies a pick makes its options expensive. When IV is rich, a debit spread caps what you overpay; when chains are too thin or spreads too wide, the overlay says so and skips.

What options do not do

Options do not reduce risk by magic — they trade one risk for another. The premium can expire worthless even when the thesis was merely early; time decay and volatility crush are real costs; illiquid chains penalize entry and exit. The overlay treats every one of these as a published, per-pick judgment — including the judgment “take the shares, skip the options” — not as fine print.

The Overlay Handbook

Every member also gets the Long-Dated Options Overlay Handbook — the full methodology in one document: how contracts are chosen, how sizing maps to the stock line, when the overlay says “take the shares instead,” and worked examples from published picks. Free for everyone on the list, because a method you can't inspect is a method you shouldn't trade.

The overlay ships with the paid letter at launch. Founding waitlist members get it included.

See the stock version in the sample letter →