The new Covered Call Roll Selector has changed my appreciation of Covered Calls as a investment vehicle, as an investing strategy.
Without proper tools it is very difficult to pick the best trades from option chains with hundreds or thousands of choices. This uncertainly (ignorance?) invites caution like, “Don’t sell calls on LTBH stocks because you might lose them.” In my case TSLA is my biggest LTBH position but it also happens to be an excellent covered call candidate. With the help of the Covered Call Roll Selector you can have the best of both worlds!
Factoid: Calls on stocks that don’t pay dividends are hardly ever called. This allows the call seller to roll the call up and out at leisure. When a call is ITM you can roll it up and out to capture the capital gain. The difficulty is finding the best trade. Before the Covered Call Roll Selector I often paid much too much to protect a stock. Now I can fine tune the trade to get at least a small premium while capturing capital. If the Roll Selector can’t find an acceptable trade, you let the call expire or try again at a later date.
What the above means is that covered calls can not only produce premium income but can also help in capturing capital gains. With this tool the strike price can track the stock’s volatility.
Roll up and out covered call option TSLA expiration 2025-09-19 strike $350
It replied:
Rolling up and out a covered call on TSLA with a 2025-09-19 expiration and $350 strike involves buying back the existing short call and selling a new call with a later expiration date and typically a higher strike price. Here’s a breakdown of what you’re doing and how to approach it:
To which I say, “NSDT!”
It did give one example:
Example (Hypothetical Pricing – For Illustration Only)
Action Option Price (Est.) Debit/Credit
Buy to Close 2025-09-19 $350 Call $25.00 –$2,500
Sell to Open 2026-01-16 $380 Call $28.00 +$2,800
Net – +$300 Credit You earn $300 to roll
(Note: Actual pricing will vary. We can look up live quotes if needed.)
Anyone can do that. The point of my software is to find the best trade from thousands of possibilities. First find a reasonably large number and then whittle it down until you find the best one for your portfolio. It’s a spreadsheet on steroids.
My pick was
$365 - 2025-10-17, just one month out instead of four.
Comparison
$100 premium instead of $300
$1,500 capital gain instead of $3,000
Per day $33.33 vs. $27.50
o o o o o o o o o o o o o o o o o o
Then I tricked it by asking about a non existent call. it didn’t blink an eye. Roll Selector said
The problem with the current level of AI LLMs is that it amalgamates the knowledge of multitudes which is good for learning but, by necessity, the output is just average. The idea behind software like the Roll Selector is to be a few steps ahead of the crowd. One day AI will do that, most likely.
Last I saw, the AI providers (at least chatGPT and probably all of them) have put a block in their code to prevent it from “picking” investments for people. It’ll do calculations, it’ll show techniques, track complex trades, etc, but it won’t “pick” specific investments. To be fair, this information is at least a year old, so maybe things have changed since then. Or maybe people have figured out a way to trick the AI into doing it.
I did a quick search and there are plenty of articles about people “using AI to invest”, and I looked at three or four of the articles. None of them showed the AI actually choosing a specific investment, just providing general information or regurgitating (in a well formatted manner) what analysts say about the market (one said “Market analysts expect the S&P500 to reach 6500 by mid-2026 …”) One article about teens using AI to invest hardly even mentioned AI and didn’t even show a single example of how a teen used AI to help them invest!
If you’r not a licensed or certified financial advisor you are not supposed (allowed?) to give financial advice. You get in trouble with the SEC. Most blogs/videos have disclaimers to protect them. Same rules should apply to AI and it’s their owners who would get into trouble.
I don’t know, I don’t have access to any paid AI service at the moment.
That’s an interesting issue … I’m quite sure that you can’t give advice and take a fee for that advice without a license of some sort. But can you give advice for free?
Example (Hypothetical Pricing – For Illustration Only)
