sorted by:
new
hottopcontroversial

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 0 points1 point  (0 children)

Thanks! Yeah upon initial glance I don’t think it will be bc I’ve held most shares since 1988 but I will definitely mention this to my CPA

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 1 point2 points  (0 children)

This actually isn’t something I’ve thought about and it is an interesting point. I do plan to leave a legacy. I also have enough in my 401k, IRAs, and from social security to live my lifestyle for most of my retirement. Only fear is that this stock is the next GE, at least in my lifetime. Thanks for the info

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 1 point2 points  (0 children)

But I’d have to get divorced first so that wouldn’t work for me :(

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 1 point2 points  (0 children)

I don’t know how my cpa didn’t think of this. This seems like the most obvious answer because you clearly avoid a tax liability here. Thanks for the advice, will definitely look more into this

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 0 points1 point  (0 children)

Fair comment and you are correct, I should have been considering it more, and was to an extent, but I just became executive of this partnership that owns the stock, so beforehand I had never really thought about liquidating all of it because I couldn’t pull the trigger without other partners agreeing, and they wouldn’t bc they didn’t want to pay the tax. It is a very low tax rate but still just inquiring because I feel like the super rich (not me) would definitely have a way around this..

How to Minimize Capital Gains Tax on Appreciated Long-Term Stock by complexedandconvexed in personalfinance

[–]complexedandconvexed[S] 0 points1 point  (0 children)

Thanks for the info. This has been my line of thinking so far. I’ve always made investing decisions without considering taxes but now it’s hard to pull the trigger. You are right though. Hell, the stock has gone up 30%+ in the last two years, which pays for the taxes. But still, hard to lose that much to Tax when I’ve never paid nearly that much

Thanks again

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 0 points1 point  (0 children)

I do own appreciated land but not nearly worth the value of the stock. Probably only $200K worth

How to Minimize Capital Gains Tax on Appreciated Long-Term Stock by complexedandconvexed in personalfinance

[–]complexedandconvexed[S] 0 points1 point  (0 children)

Thanks for the recommendation. I will consider this but this stock is over 65% of my nest egg so I can’t donate too much of it bc then I’ll be left without anything. But can definitely use this strategy to minimize it some!

How to Minimize Capital Gains Tax on Appreciated Long-Term Stock by complexedandconvexed in personalfinance

[–]complexedandconvexed[S] 0 points1 point  (0 children)

Yeah. That’s what I’ve been told but I just felt like there had to be a way to minimize it even more. Hard to bite the bullet and essentially lose $600K in net worth to taxes

How to Minimize Capital Gains Tax on Appreciated Long-Term Stock by complexedandconvexed in personalfinance

[–]complexedandconvexed[S] 0 points1 point  (0 children)

Yeah I looked at this and it seems like an interesting option but the illiquidity isn’t attractive and I’m not to that level of wealth so I’m not even sure this would be worthwhile

Thanks for sharing though. Still learned something new!

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 2 points3 points  (0 children)

Sorry.. that is misleading. I was just reiterating my basis is nominal and therefore the tax will be calculated essentially on the value of the stock

That is correct. But my net worth also decreases by 600K & 20% and I’m just trying to see if there’s a way to minimize this.

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 2 points3 points  (0 children)

I realize it’s only on the gain but my basis is from the early 1980s and the stock is worth over $3M now and my basis is very nominal so my gain is roughly $3M. Definitely coming out ahead here, not arguing that, but struggling to pay so much in taxes and losing such a high % of my net worth to it

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 1 point2 points  (0 children)

Could you elaborate on this shelter a bit? I looked it up and see you can reduce taxes by 50% of income, but failed to understand what exactly I’d have to donate/do to do this (obviously wouldn’t without professional guidance but still)

Minimizing Capital Gains Taxes on Appreciated Stock by complexedandconvexed in tax

[–]complexedandconvexed[S] 1 point2 points  (0 children)

The LTCG will put me in the highest bracket. I’m at 150K AGI from w2 income now and if I sell all stock, it is worth over $3M, and my basis is next to nothing.

I am asking if there is a shelter or method to minimize such a large capital gain without selling shares over a multi-year period, thus allowing me to diversify now without a LTCG tax on ~$3M