Capital Gains + Losses & Taxes

[Guest]

So I have some losses on a stock that has sunk ($25K investment now worth $3K). BUT I do get some company stock at my company that has done very good ($15K investment and $30K worth). For tax reasons, is it better to sell my stake in Investment 1 where my Capital gains in Investment 2 would be not be hit so hard with taxes.

 

Any thoughts?

[Thirst]

If neither have been realized, then you can just keep both. If you've already sold your company stock, it may make sense to sell the loss to net against your gains. Have you already sold your gains in stake 1?

[Guest]

No, but I will probably do it in the next month or so maybe in the Fall at the latest for Investment 2. I'm still going to feel it out. It would be a short term capital gain. So the difference is paying a possible 15% to 30% in taxes. I'm wondering if my losses in Investment 1 are great enough to cover the net against my gains in Investment 1 (loss of $22K versus a gain of $15K)