So you have $2.25M with $825k in gains. If you sell you will owe a lot of tax. I’m in a similar situation. I bought SPY put options and sold out of the money call options. I’ve held my losses to about 5%. The puts can provide 1:1 gains for each dollar lost in VTSAX for a lot less than the taxes on your gains. Depending on how far out of the money you go with the put and calls you can still have some up side benefit and/or downside exposure.
Google Is there an option to avoid the tax witholding when GSUs vest? I would rather pay the taxes myself in cash than shed a quarter of the vested GSUs. Seems like a lot of potential gains lost, no?
Rising Star
Why? So you can you buy them back when they're more expensive?
Chief
I missed the part where this sale they’re discussing would be a gain, sorry for the confusion.
Chief
So you have $2.25M with $825k in gains. If you sell you will owe a lot of tax. I’m in a similar situation. I bought SPY put options and sold out of the money call options. I’ve held my losses to about 5%. The puts can provide 1:1 gains for each dollar lost in VTSAX for a lot less than the taxes on your gains. Depending on how far out of the money you go with the put and calls you can still have some up side benefit and/or downside exposure.
Awesome
Conversation Starter
Why would you sell? Just hold. That’s 1.4m
Chief
Just buy more when it dips.
Time in market > timing the market