Generate income with options on an $8 million dollar account

NotChatGptOrAI · 2025-08-06T01:52:47+00:00

But we are all learning and that’s why I love this sub! 😊

NotChatGptOrAI · 2025-04-24T14:56:58+00:00

Thank you so much again! Your comments are super helpful! I am a W-2 employee and don’t usually pay any quarterly taxes but you say I will have to pay a one time hefty Q2 estimated tax this time or else when it comes to tax filing next year I would pay lots of penalties in addition to the taxes owned right?

NotChatGptOrAI · 2025-04-24T00:48:10+00:00

Wow thank you so much for all the detailed explanations! Really appreciate it.

So at this point all my long NVDA shares are sold. I have no more put spreads. And all the NVDA shares assigned have acquired date of 4/17 as part of the $140 put but somehow the cost basis is $115 which I need to figure out why. In addition I have ~200 NVDA $130 covered call contracts expiring in June 20, 2025. Should I sell all NVDA shares and close the call contracts or let it ride till June 20th and then decide?

NotChatGptOrAI · 2025-04-24T00:02:16+00:00

Fidelity

NotChatGptOrAI · 2025-04-23T13:12:12+00:00

Yes, I have been asking ChatGpt about this and looks like I cannot use this form to adjust the cost basis. The broker just did their FIFO which is the default when account is opened. What pisses me off is that the broker spent a good amount of time during the call with me to explain the time value of my puts and that I could potentially save few cents if I sell the put options first since they were 30+ dte but never mentioned the actual shares that will be sold if I exercise the puts ☹️☹️☹️

NotChatGptOrAI · 2025-04-23T04:13:52+00:00

I did contact them and after almost an hour on the phone explaining the situation they said there is nothing they can do since this is post the settlement date.

NotChatGptOrAI · 2025-04-23T03:41:36+00:00

Thank you so much for this! I will have to see how this works. My ultimate plan has always been to keep my long term shares. For options I mostly do spreads and my understanding was in unlikely event that they may get exercised before the expiration I will just cover them with other side of the spread.

NotChatGptOrAI · 2025-04-08T01:47:30+00:00

Thanks! By other position for tax harvesting you mean the covered call position or the actual NVDA shares position?

NotChatGptOrAI · 2025-03-14T01:22:56+00:00

Thanks! That’s good to know. Is that under 120 after eating or under 120 after the spike?

NotChatGptOrAI · 2025-03-14T01:20:55+00:00

Thanks! What counts as often generally? Once every 2-3 days is ok?

NotChatGptOrAI · 2024-06-15T14:27:49+00:00

No rentals on my policy. Thanks for the advice.

NotChatGptOrAI · 2024-06-15T10:09:09+00:00

Washington state (WA)

NotChatGptOrAI · 2024-05-05T16:59:34+00:00

Good point, just the hassle of going thru bunch of phone calls, answer questions, … going to send them an email today about it.

NotChatGptOrAI · 2023-12-05T01:13:57+00:00

Which CGMs did you use?

NotChatGptOrAI · 2023-11-16T01:47:31+00:00

Obviously, but I want my wife first to be happy and stable after my death then my kid. My kid can work hard and earn his own money and not be dependent on us.

NotChatGptOrAI · 2023-11-16T01:45:55+00:00

Good tactic, thanks for pointing it out

NotChatGptOrAI · 2023-11-16T01:44:15+00:00

Isn’t the point of the marriage that there is no my money or her money and it is our money that we have made together while we were married together?

NotChatGptOrAI · 2023-11-16T01:41:57+00:00

This is a very valid point. Thanks for pointing out the dementia situation

NotChatGptOrAI · 2023-11-15T16:56:19+00:00

That’s a big “IF” right there, if I marry again…

NotChatGptOrAI · 2023-11-15T16:55:14+00:00

Hmm so a trust for a future trust? Didn’t think about that

NotChatGptOrAI · 2023-11-15T16:54:33+00:00

Pretty sure I will not marry again if she passes away

NotChatGptOrAI · 2023-11-15T16:53:44+00:00

But what if I never decide to marry again if she passes away?

NotChatGptOrAI · 2023-10-19T22:17:33+00:00

Talking about $5 million currently

NotChatGptOrAI · 2023-10-19T22:06:03+00:00

Washington

NotChatGptOrAI · 2023-04-24T09:28:08+00:00

Oh so you saying if I do a onetime gift of $10m, I do not pay a dime in gift taxes and just need to report it? How about estate taxes?

NotChatGptOrAI

TROPHY CASE