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Another option that hasn't been mentioned - if you have good credit, you might consider a personal loan to pay the IRS in full, then pay back the loan over time. Sometimes the interest rate on a personal loan can be lower than the combined interest and penalties from the IRS (which can run about 8-10% annually when combined). Credit unions often have the best rates. I did this a few years back when I owed about $9k, got a loan at 6.5% which saved me money versus the IRS plan.
Thanks for suggesting this. Do you know if taking out a loan would impact my credit score significantly? Mine's currently around 720 and I'm trying to save up for a house in the next year or two.
There would be a small initial dip when the lender does a hard credit pull, maybe 5-10 points. Then your score might drop a little more when the new account appears, reducing your average account age. However, if you make all payments on time, your score should recover within a few months and potentially go even higher as you demonstrate responsible payment history. The biggest risk to your score would be from missing payments on the loan, which would be much worse than the temporary dips from opening the account.
Just a heads up - don't ignore this or miss the filing deadline even if you can't pay! File on time and pay whatever you can, even if it's just a small amount. The failure-to-file penalty is much worse than the failure-to-pay penalty. Failure-to-file is 5% of your unpaid taxes for each month your return is late, up to 25%. Failure-to-pay is only 0.5% per month, up to 25%. Also, make sure you request the payment plan before the tax deadline if possible. I learned this the hard way!
This is super important advice. I put off filing one year because I couldn't pay, and those failure-to-file penalties were brutal. Ended up owing way more than I would have if I'd just filed and set up a payment plan right away.
Something to keep in mind - even with the 20% they withheld, you might still owe more depending on your tax bracket. I took a distribution last year and had 20% withheld but still ended up owing more at tax time because that withholding wasn't enough to cover both the regular income tax AND the 10% early withdrawal penalty.
That's a good point I hadn't considered! Do you know if there's a way to figure out ahead of time how much I might owe? My tax bracket is probably around 22% this year.
You can use the IRS withholding calculator on their website to get a rough estimate of what you might owe based on your overall situation. With a 22% tax bracket plus the potential 10% penalty if no exceptions apply, you'd be looking at approximately 32% total tax on the withdrawal. A lot of people get surprised by this because the mandatory 20% withholding seems like it should be enough, but it often isn't. If you want to avoid a surprise tax bill, you might consider making an estimated tax payment to cover the difference.
One more thing - make sure you keep the 1099-R form you'll get in January or February. Your 401k administrator is required to send this to you and it shows the total distribution and taxes withheld. You'll need this document when filing your taxes.
Something that gets overlooked in these discussions - consider the exit strategy before picking a location. I set up in Delaware thinking it was always the best, but when I sold some equity positions last year, I faced unexpected tax complications because of California's aggressive approach to taxing residents with out-of-state entities. Make sure you understand the interaction between federal capital gains taxes and state tax obligations for equity sales. Your holding company location affects more than just annual taxes - it has major implications when you eventually sell those investments.
Would you mind explaining a bit more about those unexpected complications with California? I'm in a similar situation with a Delaware entity but live in California.
Sure thing. California takes the position that if you're a CA resident managing the holding company, they can tax the income and capital gains regardless of where the entity is formed. What happened in my case was that I had created a Delaware holding company owning several startup equity positions, but since I was making all investment decisions from California, the state considered it a California business. When I sold two of my positions for a significant gain, California required me to pay state tax on the entire gain, effectively ignoring the Delaware structure. I also had to deal with California's "doing business" fee since they deemed my holding company to be operating in California. The real surprise was that I still had to pay Delaware franchise tax while also being fully taxed by California - basically getting the downsides of both states without the expected benefits of Delaware.
Has anyone considered using an IRA to hold startup equity instead of a holding company? I've heard this can provide tax advantages for certain types of investments, especially if you expect significant appreciation.
That's actually a complicated area. You can use a Self-Directed IRA for certain equity investments, but there are prohibited transaction rules that can easily be violated with startup equity. If you're actively involved with any of the companies, it's especially problematic. Plus many equity compensation types like ISOs and NSOs can't be held in IRAs directly.
An important factor nobody's mentioned yet - check if there's a tax treaty between the UK and New Zealand! This can make a huge difference in avoiding double taxation. Usually these treaties have specific provisions for determining where a company is considered resident for tax purposes when there's ambiguity like in your situation.
Theres also something called a "tie-breaker" rule in most tax treaties that helps determine which country gets primary taxing rights when both claim you. Usually comes down to where you have stronger personal connections, permanent home, etc.
You're absolutely right about the tie-breaker rules. They're crucial in these situations. Most treaties follow a hierarchy of tests: permanent home first, then center of vital interests (personal/economic connections), then habitual abode, and finally nationality. For a company, the tie-breaker often comes down to where the effective management is located - which in the original poster's case would likely be New Zealand since that's where the actual decision-makers are physically located, regardless of where the company is registered.
Get ready for a paperwork nightmare! I have a similar US/UK situation and end up filing in both countries. The key is finding a good accountant who specializes in international taxation - don't try to DIY this!!
How much does an international tax accountant usually cost? I'm in a similar boat with income from three different countries and I'm terrified of getting it wrong, but also worried about the cost.
Anastasia Kuznetsov
Has anyone used any tax software that makes amending 1099s easier? I'm using QuickBooks and it's not very intuitive for handling corrections.
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Sean Fitzgerald
ā¢I've had good experiences with Track1099 for corrections. Their interface is really straightforward for amendments - there's literally a "create correction" button that walks you through the process step by step.
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Anastasia Kuznetsov
ā¢Thanks for the recommendation! I'll check out Track1099. QuickBooks has been a nightmare for this - it keeps wanting me to create new 1099s from scratch without any way to mark them as corrections properly.
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Zara Khan
Just a heads up - if your original 1099 had an incorrect TIN (tax ID number) for the contractor, the correction process is slightly different. You'll need to: 1. Create a new 1099 with all zeros in the amount boxes 2. Mark it as "CORRECTED" 3. Submit this to void the original 4. Then create another NEW 1099 with the correct TIN and amounts 5. Don't mark this one as "CORRECTED" Made this mistake last year and had to redo everything a third time.
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