June 24, 2025

Ep20 - Square, Level and All Effed Up

37 minutes

Description:

You wouldn’t build a garden without a plan (or at least you shouldn’t). And you sure as heck shouldn’t place a covered call or cash-secured put without knowing exactly why you’re doing it.

In this episode, Dan shares a hilariously frustrating story about building a backyard garden with his daughter — and how forgetting one small measurement led to a big headache. Then he breaks down how that same mistake shows up in options trading when traders skip the fundamentals and just “wing it.”

Covered calls and cash-secured puts might seem simple — but if you’re not following this checklist, you’re likely doing it wrong. This episode gives you the must-follow framework to avoid costly errors and start trading with clarity and confidence.

You’ll Learn:

The only two valid reasons to place a covered call or CSP — and why anything else is a red flag

Why stocks under $30 are usually a waste of time for income strategies

What the “10% Rule” is — and how it instantly tells you if your option is tradable

How to use theta and “aggregate theta” to maximize your returns over time

The rookie mistake traders make by ignoring volatility events like earnings (and how to avoid it)

Key Insight:

“You don’t get to think outside the box until you know what’s inside it.”

Don’t Miss:

Dan’s “Nail the Trade” checklist — the same system he’s been refining for 8+ years

Why implied volatility isn’t always make-or-break — and when it is

How to line up your trade with your actual investing plan, not just what “looks good”

Disclosure:

Options involve risk and are not suitable for all investors. Prior to buying or selling an option, investors must read Characteristics and Risks of Standardized Options (ODD) which can be found at https://www.theocc.com/company-information/documents-and-archives/options-disclosure-document

Don’t trade with money you are not prepared to lose. Anything discussed on this show is intended to be generalized information and not intended to be a recommendation to buy or sell any security. The host and guests are not familiar with listeners’ specific situations. For trading information relevant to your specific needs, speak with a licensed broker or advisor.

Trumpet

Trumpet Fanfare by bevibeldesign -- https://freesound.org/s/350428/ -- License: Creative Commons 0

Wah Wah Wah

Wah wah trumpet failed joke punch line.wav by Doctor_Jekyll -- https://freesound.org/s/240195/ -- License: Attribution 4.0

...more