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Has anyone here actually tried implementing a smaller version of this strategy? I have about $200k in company stock that's appreciated a lot, and I'm considering taking out a loan against it to renovate my house instead of selling the shares and triggering capital gains. Not exactly Elon Musk level, but I'm wondering if the "buy, borrow" part of the strategy makes sense for regular-ish people too? What interest rates are banks offering on these securities-backed loans for non-billionaires?
@Dylan Baskin I d'also suggest looking into whether your company stock qualifies for any special tax treatment before deciding. If these are incentive stock options ISOs (or) employee stock purchase plan shares, there might be better tax strategies than borrowing against them. For example, ISO shares can qualify for long-term capital gains treatment lower (tax rates if) you hold them long enough after exercise. ESPP shares might have some portion treated as ordinary income anyway. The tax savings from avoiding sale might not be as significant as you think depending on your specific situation. Also consider the psychological factor - when you sell stock for a renovation, the project is paid "for. With" a loan, you ll'have ongoing monthly payments plus the stress of watching your collateral value fluctuate. Sometimes the peace of mind is worth paying the capital gains tax upfront.
@Dylan Baskin I ve'been exploring this same question and found that many regional banks and credit unions offer securities-backed lines of credit starting around $50k-100k in collateral. Rates typically range from prime + 0.5% to prime + 2% depending on your relationship and loan-to-value ratio. One thing I learned is that these loans are usually structured as lines of credit rather than term loans, which gives you more flexibility. You only pay interest on what you actually borrow, and you can pay it down whenever you want without penalties. That said, I d'echo what others have mentioned about concentration risk. If all $200k is in one company s'stock, you re'essentially doubling down on that single investment. Maybe consider selling some shares to diversify first, then using the securities-backed loan strategy on the remainder? That way you re'not putting all your eggs in one basket while still getting some benefit from the tax deferral strategy.
One aspect that hasn't been mentioned yet is the estate planning angle of this strategy. The "die" part of "buy, borrow, die" is actually crucial for making the whole thing work long-term. When someone dies, their heirs inherit assets with a "stepped-up basis" - meaning the cost basis resets to the fair market value at death. So if Musk bought Tesla stock at $10/share and it's worth $200/share when he dies, his heirs inherit it as if they bought it at $200/share. All those unrealized gains from $10 to $200 are never taxed. This is why the ultra-wealthy can keep rolling over loans indefinitely. They don't necessarily need to pay them back during their lifetime - the estate can sell inherited shares (with no capital gains tax due to stepped-up basis) to pay off any outstanding loans after death. It's a pretty remarkable feature of our tax code that essentially allows generational wealth to avoid capital gains taxes entirely. The heirs start fresh with a new basis, and the cycle can continue for generations.
This is exactly what I was missing from my understanding! The stepped-up basis at death is what makes this whole strategy actually work long-term. Without that piece, I couldn't figure out how the loans would ever get fully paid off without eventually triggering massive capital gains taxes. So essentially, the ultra-wealthy are using the tax code's treatment of inheritance to permanently avoid capital gains taxes on their lifetime appreciation. That's pretty incredible - and explains why this strategy becomes more powerful the longer you can keep the cycle going. It also makes me understand why there's been political discussion about eliminating or modifying the stepped-up basis rule. Without it, this whole "buy, borrow, die" approach would fall apart because eventually someone would have to pay capital gains on all that deferred appreciation. Thanks for explaining that missing piece - now the full picture makes so much more sense!
This is a complex situation that requires careful attention to both timing and documentation. Since you're physically present in the US while working, a few additional considerations: 1. **Work authorization**: Even though you're a US citizen, your EU employer may need to understand the legal implications of having an employee working from the US. Some companies have policies against this due to corporate tax nexus issues. 2. **Estimated tax payments**: Since your EU employer isn't withholding US taxes, you'll likely need to make quarterly estimated payments to avoid underpayment penalties. Use Form 1040ES to calculate what you owe. 3. **Record keeping**: Document everything - dates of travel, where you performed work, foreign taxes paid, and currency conversion rates. The IRS may question the source and timing of your income. 4. **Professional help**: Given the complexity with dual citizenship, foreign employment, temporary US presence, and potential state tax issues, I'd strongly recommend consulting with an Enrolled Agent or CPA who specializes in international tax. The cost is usually worth avoiding costly mistakes. The foreign tax credit route mentioned by others is likely your best approach, but the devil is in the details with your specific circumstances.
This is excellent comprehensive advice! I just want to emphasize the estimated tax payments point - I made this mistake in a similar situation and got hit with penalties even though I paid everything when I filed my return. The quarterly payment deadlines are strict (Jan 15, April 15, June 15, Sept 15) and since your EU employer isn't withholding US taxes, you're essentially treated as self-employed for payment purposes. I ended up owing about $800 in underpayment penalties on top of my regular tax bill. Also regarding the work authorization point - some EU companies actually have specific policies about remote work from certain countries due to tax implications. My former employer in Germany had to set up a whole process when employees wanted to work temporarily from the US because it potentially created US tax obligations for the company itself.
Just to add another perspective on this - I went through a very similar situation working for a Dutch company while caring for family in the US for about 8 months. A few things I learned the hard way: **Banking complications**: Your EU bank might freeze or question your account if they detect you're consistently accessing it from the US for an extended period. I had to provide documentation to my Dutch bank explaining my temporary situation to avoid account restrictions. **Social security treaties**: Don't forget about the US-EU social security agreements! If you're paying into the EU social system while physically in the US, you might be able to avoid double social security taxation. This is separate from income tax treaties but equally important. **Professional liability**: If your work involves any professional licenses or certifications, check if working from the US temporarily affects their validity. Some EU professional bodies have specific requirements about where licensed work can be performed. **Currency fluctuation tracking**: Since you're paid in Euros but will file in USD, keep detailed records of exchange rates on payment dates. The IRS requires you to use the rate on the day you received the income, not year-end rates. I used the Treasury's published rates to stay consistent. The Foreign Tax Credit approach others mentioned is definitely correct, but these operational details can trip you up if you're not prepared. Good luck with your family situation - hope everything works out well!
This is incredibly helpful advice, especially the banking point! I hadn't even thought about potential account restrictions. Quick question about the social security treaties - if I'm already paying PAYE taxes in my EU country which includes social contributions, would I still need to pay US social security taxes on the same income while working here temporarily? Or does the treaty typically prevent that double taxation too? Also, for the currency exchange tracking, did you find any good tools or apps to automatically track the Treasury rates, or did you just manually record them each payday?
Don't forget you can also use Section 179 to just expense the whole printer in year 1 instead of depreciating it over 5 years with MACRS! Since $8,200 is well under the Section 179 limit of $1,190,000 for 2025, you could just deduct the entire amount this year if that's better for your tax situation.
That's really helpful to know! If I choose the Section 179 route instead of MACRS, are there any downsides I should be aware of? And if I do this, do I still need to fill out the depreciation forms or is there a different form for Section 179?
The main downside is that if your business income is less than the Section 179 amount, you can only deduct up to the amount of your business income. So if you're just starting out or having a low-income year, MACRS might be better to spread the deductions across years when you might be making more money. For forms, you'll need to complete Form 4562 for either Section 179 or MACRS depreciation. The form has specific sections for each method, so you'll just fill out the Section 179 part (Part I) instead of the MACRS section if you go that route.
Quick tip from someone who's been burned before: KEEP DETAILED RECORDS of all your depreciated assets! I learned this the hard way when I got audited last year and couldn't find the original invoice for equipment I was depreciating using MACRS. Create a folder (physical or digital) for each asset with: - Original purchase invoice - Documentation showing when it was placed in service - The MACRS class you assigned and why - Your depreciation calculations each year Trust me, if you get audited 3-4 years from now, you won't remember the details without good records.
Would a spreadsheet tracking all assets work, or do you really need separate folders for each item? I've got about 20 different assets I'm depreciating and separate folders seems excessive.
A spreadsheet absolutely works! That's actually what I use now. I have columns for asset description, purchase date, cost, MACRS class, depreciation method, and then separate columns for each year's depreciation amount. The key is just making sure you can easily find the supporting documentation. I keep all my invoices in one folder (or cloud folder) and just reference the file name in my spreadsheet. As long as you can quickly locate the paperwork when needed, you're good. The IRS cares more about having the documentation than how you organize it. For 20 assets, a well-organized spreadsheet is definitely more practical than 20 separate folders!
Anyone here actually used a CRT for crypto specifically? I'm looking at doing this with some Ethereum that's way up from my cost basis, but my attorney seems hesitant about using crypto in a trust like this. Said something about valuation issues.
I set up a CRUT (not a CRAT) with Bitcoin last year. The key challenge was getting proper valuation documentation for the IRS. We used the average of three exchanges at exactly the same time to establish FMV. Also, the trustee immediately converted to a diversified portfolio to avoid exactly the scenario OP is worried about. No regrets so far - saved a ton on capital gains and the income stream is stable now that we're not at the mercy of crypto volatility.
This is exactly why I always recommend consulting with both a tax attorney AND a financial advisor who specializes in charitable trusts before setting up any CRT with volatile assets. The interplay between the 10% remainder rule, payment obligations, and asset volatility can create serious cash flow issues even when you're technically compliant with IRS requirements. One strategy I've seen work well is setting up what's called a "flip CRUT" - it starts as a net income makeup trust (NIMCRUT) that only pays out actual income earned, then "flips" to a standard unitrust once a triggering event occurs (like diversification of the original volatile assets). This provides protection during periods when the trust assets might not generate enough income to support full payments. The key takeaway from your crypto example is that while the 10% rule won't be violated by market crashes after establishment, you could end up with a trust that gets completely depleted paying the fixed annuity amounts, leaving nothing for the charitable remainder. That defeats the whole purpose of the structure.
This is incredibly helpful information! I hadn't heard of a "flip CRUT" before but it sounds like exactly what I need for my situation. The idea of starting with income-only payments until the assets can be diversified makes so much sense for volatile investments like crypto. Could you explain a bit more about what typically serves as the "triggering event" for the flip? Is it usually just the sale and diversification of the original assets, or are there other common triggers people use? And does setting up this type of structure significantly complicate the trust documents or make it more expensive to establish? I'm wondering if this approach would work for my crypto situation where I want to avoid immediate capital gains but also don't want to risk depleting the trust if the market crashes again.
Sophia Russo
Don't forget that this needs to be the FINAL 1041 with the "Final Return" box checked. Many executors miss this and end up getting notices from the IRS asking for returns for subsequent years. Also make sure Form 56 (Notice Concerning Fiduciary Relationship) is filed showing the termination of the fiduciary relationship.
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Evelyn Xu
ā¢Is Form 56 always required? I settled my grandmother's estate last year and our attorney never mentioned this form.
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Ella Lewis
Just to add another perspective - make sure you have clear documentation showing your mom was acting in her capacity as Personal Representative when she paid these fees. A simple letter or memo to the file stating something like "Paid attorney fees of $7,600 on behalf of [Estate Name] from personal funds due to bank restrictions" can be helpful documentation. Also, when you enter these on the 1041, you might want to attach a brief statement explaining the circumstances (that the estate's bank wouldn't allow the payment but the PR paid personally). This isn't required, but it can prevent questions later if the IRS reviews the return. The good news is that since your mom was the sole beneficiary, this is really just a timing difference - the money was always going to come out of "her" funds eventually anyway, whether directly from the estate account or indirectly through her inheritance.
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Aisha Mahmood
ā¢This is really helpful documentation advice! I'm new to dealing with estate taxes and hadn't thought about creating a paper trail for expenses paid personally. Would you recommend keeping copies of the canceled checks or bank statements showing the payments as well? I want to make sure we have everything properly documented in case there are any questions down the road.
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