YouBet said:

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FTAC2011 said:

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This is only long term gains, correct?

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Yes. The 0% rate applies to net long-term capital gains and most dividends.

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Only qualified dividends.

Any fans of direct indexing tax loss harvesting? Intriguing concept to offset some future profit realization.

YouBet said:

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For all you lolpoors trying to get rich on stocks, here is one I was not aware of...

If you are single filer with taxable income up to $49,450 or a joint-filer with income up to $98,900 you pay 0% capital gains tax.

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I've seen this applied quite a bit - usually on elderly selling land. It saves the day!

08N.Ftw.Ag said:

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Any fans of direct indexing tax loss harvesting? Intriguing concept to offset some future profit realization.

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Absolutely, I was reading this thread and thinking the same thing. I have a professionally managed Fidelity account that mirrors the S&P with tax loss harvesting that I really like.

It could also be pretty big deal for inherited stocks or any other long term holds that you may want to sell as well.

Holistic Planning said:

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Donor Advised Fund
Gifting highly appreciated stocks or other assets in one year. Then you can potentially use it to offset the taxes from a Roth conversion if applicable.

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Tell me more. I am in a high tax bracket and this seems like a good way to achieve dual Goals. Say I have 100K in appreciated Tesla stock in my IRA and cost basis is10K. If I donate the 100K stocks, would there be any tax/withdrawl implications? Would this 100K donation be 100K off my income?

bagger05 said:

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Real estate professional plus cost segregation studies and accelerated depreciation.

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I thought about this and seems like a lot of work for up front depreciation but then lose out on ongoing depreciation. Plus when you sell, then cost basis is low and thus higher taxes on gain.

If the stock is in your IRA you can't use that for a donor advised fund unfortunately. Only if it's after tax stock.

When you turn 70.5 then you can do QCDs.

If your Tesla was in a joint account and has a 10k basis and value of 100k then yes you can donate that stock to a DAF and get a 100k deduction. You'd need an AGI of 300k to make it work though because you can only deduct 30% of your AGI when you gift stock.

knoxtom said:

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Not really.

You just forfeit the stock that you are using as collateral. Since you know the bankers and this is an ongoing relationship and repeated every year they are fine with it.

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Tell me more. If I have a good relationship with a banker, can I do this with my IRAs? If so, what kind of rate do they give?

Here is what I am doing because I am in the top tax bracket given the green light by my CPA.

1. Turned my pass through LLC into an S corp to save some SS taxes
2. Employ myself and my wife with income to max out a CBP
3. Put 500K+/year in CBP for both of us saving about 170K taxes/yr
4. All my kids employed with minimal wages to max out their Roth. No tax benefits but they will thank me in 20 years when they are in the mid 30's.
5. Any trips we take as a family are always business trips that we discuss business, thus able to write off as business
6. I have 5+M in Real estate equity. Once I hang everything up and have no income, I will be refinancing all my properties and living off the loans. I will never touch my IRAs/stocks/cash and just let them all appreciated. When I die, kids/family can have it with step up basis vs Trust
7. Invest in O&G with about 90% tax write off. Did 100K this year which reduces my income by 90K.

Question I have is what left can I do? I have looked and decided not to be a RE professional.

If I have a really high yearly income mainly K1 and it all comes from my privately held company, can I do something where I convert it to stock options then get a banker to loan me $$$ against the options? Just thinking about this, I think it will be a no go.

The real estate professional works really well in some circumstances but it is probably not a good idea unless you actually want to be a real estate investor. You kinda need to keep buying real estate for it to work well. Plus you have to be doing more in real estate than you are in anything else, so anything resembling another job makes it a non-starter for almost everyone.

In my opinion, the answer to "what else can I do?" is to get an accountant that's actually a tax advisor. Based on what you're saying and the amount of money that's at stake, you'll get a huge ROI from working with a pro.

There are tax ADVISORS and there are tax PREPARERS. Almost everything about these two providers is different (including how much they cost). The tricky part is that every CPA out there describes themselves as a tax ADVISOR.

For the kind of money you're talking about, your CPA should be the person who is BRINGING you these ideas and putting together a tax strategy based on your goals - not "giving you the green light" on ideas you're researching and taking to them.

When it comes to financial planning and wealth management, at some point tax strategy becomes basically THE most important thing. Obviously I don't know your situation, but based on the numbers you're talking about I think you might be in that spot.

I agree with the poster above -- if you've been given the "green light" to write off every family vacation as a business expense because you "talked business", then you've been given "yeah you'll probably be fine" advice.

Which is just that -- you'll probably be fine.

And unless you and your wife are both up there in age, you won't be able to contribute that much to your CBP every year.

And not tax saving related but if you don't have an umbrella policy I'd make that priority number 1.

YouBet said:

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For all you lolpoors trying to get rich on stocks, here is one I was not aware of...

If you are single filer with taxable income up to $49,450 or a joint-filer with income up to $98,900 you pay 0% capital gains tax.

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You haven't had any qualified dividends or long-term capital gains in the past 20 plus years?

one safe place said:

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YouBet said:

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For all you lolpoors trying to get rich on stocks, here is one I was not aware of...

If you are single filer with taxable income up to $49,450 or a joint-filer with income up to $98,900 you pay 0% capital gains tax.

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You haven't had any qualified dividends or long-term capital gains in the past 20 plus years?

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I have. I doubt I will qualify for this in 2026 even with me retiring. I was just pointing it out as a strategy for others because it's not widely known about.

bagger05 said:

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The real estate professional works really well in some circumstances but it is probably not a good idea unless you actually want to be a real estate investor. You kinda need to keep buying real estate for it to work well. Plus you have to be doing more in real estate than you are in anything else, so anything resembling another job makes it a non-starter for almost everyone.

In my opinion, the answer to "what else can I do?" is to get an accountant that's actually a tax advisor. Based on what you're saying and the amount of money that's at stake, you'll get a huge ROI from working with a pro.

There are tax ADVISORS and there are tax PREPARERS. Almost everything about these two providers is different (including how much they cost). The tricky part is that every CPA out there describes themselves as a tax ADVISOR.

For the kind of money you're talking about, your CPA should be the person who is BRINGING you these ideas and putting together a tax strategy based on your goals - not "giving you the green light" on ideas you're researching and taking to them.

When it comes to financial planning and wealth management, at some point tax strategy becomes basically THE most important thing. Obviously I don't know your situation, but based on the numbers you're talking about I think you might be in that spot.

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I have talked to a tax advisor that was well rated and they didn't give me much more than what I do now or some things I found pushing the envelop. My current CPA are brining me ideas and some are "exotic" that I have not pulled the trigger. Maybe next year, I may delve into these exotics but they always come with increased chance of Audit.

Agree with umbrella as poster noted above, I have had one for 10 years.

My CBP/IRA for me/wife allows 500K+ contributions a year which at least puts a dent in my taxes.

Pick up all the discarded losing tickets at the horse track and claim gambling losses every year while also doing your part to reduce trash!

There's a really interesting strategy from the hedge fund AQR that provides serious tax benefits as well. Business trader tax status feels like a cheat code!