Anonymous wrote:Use it as collateral for a loan.

How does this offset the taxes that will be due when the buy out occurs? I’m very familiar with the “Buy-Borrow-Die” strategy but the stock will be sold for cash when the deal closes regardless of whether I’m using it for collateral.

OP here — jeez I’m sorry I ever posted on the DCUM “Money and Finance” forum looking for some simple investment and tax advice based on some of the snotty answers on here. DCUM is toxic.

Set up a charitable remainder trust. Put the stock in there before the deal closes. You won’t pay taxes on the capital gains and can withdraw income from the trust while you are alive or for a certain term depending on how it’s set up. Whatever is left when you die goes to the charity you designated. Win-win.

Anonymous wrote:Purchase a property to use for short term rentals like airbnb. If the property is worth, say $1,000,000 and you put $200K down, you can get a cost segregation study and get about a $300K deduction to offset your taxes with the Big Beautiful Bill's accelerated bonus depreciation. The money from the rental will pay for the monthly mortgages provided you choose the property wisely.
You do need to be involved in managing the property, but you cam also hire a management company and help them out as well.

OP here…I have no desire to be a landlord again. Been there done that.

Use it as collateral for a loan.

Anonymous wrote:If you're making sooo much money off of this, you can afford professional tax advice and don't need to get it from this silly forum.

OP here…sure I could but thought I get some serious thoughts on this forum as well as Bogleheads before doing that.

Purchase a property to use for short term rentals like airbnb. If the property is worth, say $1,000,000 and you put $200K down, you can get a cost segregation study and get about a $300K deduction to offset your taxes with the Big Beautiful Bill's accelerated bonus depreciation. The money from the rental will pay for the monthly mortgages provided you choose the property wisely.
You do need to be involved in managing the property, but you cam also hire a management company and help them out as well.

Well, time to dump losers in your portfolio if you have any.

You could do a DAF. Let's say you fund with 100k, and that gives you a major deduction this year, then you can give that away over the next couple years. At least I think that's how it works. I myself have not been in the position of having too much money

Buy a bare-bone tie house renovate it into a 4+ units rental. Do all renovations in same year as capital gain and write it off as loss instead of amortizing. Win-win

Anonymous wrote:Make charitable donations with the stock - as in donate the stock. That saves you cap gains on the stock plus you get a charitable deduction.

That is the best answer. To repeat: You don't pay any gains on the stock you donate, AND you can take the charitable deduction for the NEW higher value of the stock. So for example if you invested $100,000 and it increased to $200,000, and you donate the $200,000, you avoid about $25,000 in taxes on the gains that you don't pay, plus you can take a $200,000 itemized charitable deduction, reducing the amount of taxes you pay on your other income. Of course, you don't have to donate it all; that's just a simple example. (There are complications; for example, you can generally only deduct 50% of your AGI as charitable deductions.)

If you don't want to donate it all at once, you can move it to a Donor Advised Fund. You get all the tax benefits up front but can direct the donations over time.

And this is only tangentially related, but I'll recommend considering donating through GiveWell (https://www.vox.com/future-perfect/23976937/charity-giving-tuesday-givewell-ten-percent)

Anonymous wrote:Ask at Bogleheads.org

The children posting here don’t fit in there.

You’ll get the same answers there as here— sell something at a loss, charitable donation, or die— just less commentary.

Ask at Bogleheads.org

The children posting here don’t fit in there.

Anonymous wrote:See a tax planner, you cheapo.

He's so poor he can't pay his taxes. How do you expect him to afford a tax planner?

Nothing much to do. I would have taken a year or two off from work. I barely work, because I have plenty of money coming from LTCG paying nearly nothing.
Concentrate on investing the money well. You will make 30% + up in no time.

Anonymous wrote:If you're making sooo much money off of this, you can afford professional tax advice and don't need to get it from this silly forum.

Yeah, this is just a humble brag.