Subject: Re: BRK covered Calls: Lesson (learned?)
I wrote shorter term ones, closer to the money, for much higher premiums. Each time they got old, I rolled them up and out for approximately zero net cash change.
How did you manage to do that? I could understand that in the first half of the year, with BRK constantly up and down. But since July most of the time BRK did rise only. There were very few longer stretches down you could use to buy back old calls without a loss.

I cheated.
I rolled them to later dates, and higher strikes, but the strikes I used were sometimes only *a little* higher. So at the time I wrote many of them, they were already well in the money. This means I didn't get nearly as much time value, but the cash value was about right so that each roll was very roughly cash neutral.

A made up example, as I'm too lazy to dig into the trade records:
e.g., say I wrote four-month $420s when the stock was at around $415-$420. I tend to go for strikes very close to the current price since I like the boatloads of time value and don't fear exercise.
2-3 months go by and the stock has gone to $450. The positions is in a hefty mark-to-market loss and it will take a lot of cash to close it. ("this too shall pass", I tell myself)
I might close the $420s and write $430 or $435 expiring three months later for about the same cash value. The breakeven price rises each time I do this, though not as much as the stock price has risen. The difference is that my breakeven always goes up, but the same is not true of share prices : )

Aiming for the same cash value isn't because I'm obsessed with the cash in and out of the Berkshire section of my portfolio--it isn't a substitute proxy for profit and loss. Rather, it's because the amount of cash raised is equal to the maximum profit on the position. If you roll to a new call with about the same cash value, it also has about the same maximum upside. If Berkshire really did go down into the basement, those calls that I wrote with "little" time value would make a mint as the in-the-money value also goes away.

After having rolled up and out a few times, the weighted average "net exit" price (strike plus premium) of my currently open short call positions is about $493. I also have a mark-to-market loss at the moment on all the open and closed positions combined since mid 2023, less than $5 per share. The MTM loss is gradually shrinking as the time value erodes, and if the stock price stays flat here it will turn into a profit. If the stock price settles lower for a while, it will be quite a big profit.

Jim