micha8st t1_ja5u2js wrote on February 27, 2023 at 1:38 AM

I've been collecting RSUs for awhile, and I sold some in late 2019, in 2020, and in 2021.

The brokerage account my employer gave me for this purpose allows me to chose lots to sell. I'm making up dates...but I could sell two lots simultaneously... one lot that was granted in 2016 and vested in 2019, and another lot that was granted in 2020 and vested in 2021.

Lets say at the price I sell, the 2016/9 lot is up 545.32, and the 2020/1 lot is down 543.16.545.32 - 543.16 means a net gain of 2.16 -- I'd have to pay taxes on $2.16.

So... I could figure out a price where I can sell those two lots simulataneously and have no net gain or net loss. I didn't bother.

Or... maybe I have a third lot...and at the price where I sell, the 2016/9 lot is up 752.38, the 2020/1 lot is down 238.38, and the third 2017/20 lot is down 520.00.752.38 + (-238.38) + (-520) = 752 - 748.38 = a gain of 3.62.

Me, I chose to just sell without worrying about tax loss harvesting (as what I described is called)

If you have a big net capital loss, that loss can be carried forward. You can only "use" $3000 of the carried-forward loss in any given calendar (tax) year.

riku2o OP t1_ja5vzqb wrote on February 27, 2023 at 1:53 AM

Thanks for the perspective! Yeah I think your perspective and the other ones I'm seeing commented so far align with my thoughts of just get out and diversify. For what its worth, the entire market has been down so Im havent lost all that much relative to what it wouldve been if I were already diversified, but nobody likes leaving money on the table. It also probably ends up saving me a trip to CPA to figure out the most optimal way to sell my RSUs

micha8st t1_ja60t06 wrote on February 27, 2023 at 2:31 AM

in my case, the stock has been a ride.

I like having mathematical triggers -- I make up a formula, and it tells me when to sell.

Through Dec 2019 - Jan 2020, I sold... I think it was 9 lots, at an ever increasing price. The formula would give me a next price to sell at relative to the previous price.

My employer's stock went up December 2019 - March 2020...then when the bottom fell out of the market in later March 2020, it dropped to about half where I sold my first lot of vested RSUs. By October 2020, the stock was to price where I'd stopped selling in january. It kept, generally, going up, and peaked early december '21 at double where I sold my first lot. Then it's dropped. My formula tells me I should sell my next lot at 100.37, but it ended the day Friday at 78.05.

Now... why did I stop? Both times because the total value reached my goal -- the sales brought the total value of employer stock below my target.

In your case, I suggest setting a target -- say 10% of your net worth -- and slowly pare back your vested-RSU holdings down to that level. Further, I'd see if I can't come up with some pairings that make sense to roughly where stock is selling...say +/- 10%.