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As someone who runs an Amazon FBA business from Japan with a Wyoming LLC (similar to your setup), here's what I've learned: The 1099-K is reporting the payments processed through Shopify Payments, but that's just your gross revenue. The key is properly documenting ALL your expenses. Since you're shipping directly from China, make sure you have proper documentation for COGS, including manufacturing, shipping, and any duties paid. For Wyoming specifically - yes, no state income tax, but you still need to file an annual report and pay the $60+ annual fee to maintain good standing. One thing to watch for: if your US company is just a "paper entity" and all real work happens in China, the IRS might question if you have "nexus" in the US at all. This could either help or hurt depending on your situation.
Thanks for this info! What do you mean by "paper entity" and the nexus issue? Our company is registered in Wyoming, has a registered agent there, and a US bank account, but all actual operations (including me as the owner/operator) are in China. Could this cause problems?
The "nexus" issue refers to where your business has sufficient presence or connection for tax purposes. If all actual business activities (management, operations, inventory) are in China, the IRS could potentially view the business as a foreign entity despite the US registration. This could work both ways. If determined to be a foreign entity, you might only need to report US-sourced income to the IRS, potentially reducing your tax burden. However, it could also trigger complex reporting requirements like Form 5471 for foreign corporations. To strengthen your US nexus, consider: maintaining a US phone number, having some business activities conducted in the US (even if remotely), using US-based services, and clearly documenting the business purpose of your US entity. Having just a registered agent and bank account might be seen as insufficient to establish true US operations.
Don't forget about FILING THRESHOLDS for the 1099-K! This is important and changed recently. For 2023 taxes (filing in 2024), the threshold is still $20,000 AND 200 transactions. But starting with 2024 taxes (filing in 2025), it drops to just $5,000 with NO transaction minimum. If your 1099-K is reporting less than the threshold amount for the applicable tax year, you technically weren't supposed to receive it. But now that you did, you still need to report that income (but can offset with expenses).
Actually, this information isn't quite right. The $600 threshold was supposed to take effect for 2023 taxes (filing in 2024), but the IRS delayed it. They've announced another delay for the 2024 tax year too. So the $20,000 AND 200 transactions threshold is still in effect for both years. I just want to make sure nobody's confused when filing!
I use Koinly for tracking all my crypto transfers and it automatically tags them as non-taxable events. Been using it for 3 tax seasons now and it generates all the forms I need for filing. Just another option to consider.
The price depends on how many transactions you have annually. I'm on the $99 plan which covers up to 1,000 transactions per tax year. They have cheaper options if you have fewer transactions and more expensive if you're a heavy trader. I've found it worth it because it automatically categorizes everything correctly - transfers, trades, income from staking, etc. You can also manually edit any transactions if needed. At tax time, it generates all the forms needed for filing including Schedule D and Form 8949.
Anyone know if hardware wallets like Ledger complicate this? I transfer from Coinbase to my Ledger for security, then sometimes back to an exchange if I want to sell.
Something no one's mentioned yet - have you looked into setting up an S-Corp election for your LLC? At your income level, it might save you significant self-employment taxes. With an S-Corp, you'd pay yourself a reasonable salary (subject to FICA taxes) and take the rest as distributions (not subject to self-employment tax). Could save you thousands depending on your situation.
I've heard about the S-Corp option but wasn't sure if my income was high enough to make it worth the extra paperwork and accounting costs. What's considered the breakeven point where it starts making sense financially?
The breakeven point varies depending on your specific situation and local costs, but generally around $40,000-60,000 in profit is where many tax professionals suggest considering it. At your $52,500 income level, you're in that range. The main calculation is comparing what you'll save in self-employment taxes versus the additional costs. You'll need to file Form 1120-S annually, likely pay for payroll services (roughly $50-100/month), and possibly higher accountant fees. Most people find it worthwhile when they can save at least $2,000 annually in taxes after covering these extra expenses.
Don't forget to check if you qualify for the Qualified Business Income (QBI) deduction! As a sole proprietor, you might be able to deduct up to 20% of your qualified business income. This is a big tax break that a lot of people miss.
The QBI deduction is amazing but gets complicated fast. I thought I didn't qualify but my tax person found a way to make it work by adjusting some of my expense categories. Ended up saving almost $2k last year!
One thing that hasn't been mentioned is that there's a crucial difference between RSUs (Restricted Stock Units) and ESPPs. With RSUs, there's typically withholding at vesting because that's a taxable event (ordinary income). With ESPPs, taxation gets more complicated. If your ESPP has a "lookback provision" where you get to purchase at a discount from either the beginning or end of the offering period (whichever is lower), there can be additional tax implications. The discount is always taxable as ordinary income, but depending on whether you do a qualifying or disqualifying disposition, the timing and treatment of taxes varies. From what you've described, it sounds like your company might be withholding for the discount portion, but calling it capital gains tax, which is confusing you. I'd ask for documentation that specifically explains what portion of your purchase is being taxed and under what section of the tax code.
Can you explain what a "qualifying or disqualifying disposition" means? The tax document they sent me does mention something about a "disqualifying disposition" but doesn't explain what that means.
A qualifying disposition means you held the ESPP shares for both: 1) at least 1 year after the purchase date, and 2) at least 2 years after the offering date (when the purchase period began). If you meet both holding periods, you get more favorable tax treatment. A disqualifying disposition means you sold before meeting either of those holding periods. In that case, the entire discount gets taxed as ordinary income. It's strange they're mentioning "disqualifying disposition" if you haven't sold yet. That term typically only applies when you actually sell the shares. This reinforces my suspicion that there's a communication problem or misunderstanding with your benefits department. I'd specifically ask them why they're referencing a disqualifying disposition when you still hold the shares.
Has anyone considered that this might actually be a prepayment of taxes that the company is facilitating, rather than requiring? Some companies offer this as a service to help employees avoid a big tax bill later. If the ESPP discount is substantial, or if there was a big jump in stock price during the offering period, there could be a significant taxable event even before selling. The company might be offering to withhold taxes now to help spread out the impact rather than having employees face a surprise tax bill next April. I'd ask if this withholding is mandatory or optional. If it's optional, it might actually be a beneficial service they're providing.
This is an excellent point. My company does something similar - they provide an optional tax withholding program for equity compensation. They calculate the projected tax impact and let us choose whether to have extra withholding throughout the year. It's actually really helpful for cash flow management.
Caleb Bell
One thing nobody mentioned yet - you need to make sure you actually pay the amount you agreed to on the CP2000. Even if you responded agreeing to the assessment, if you didn't send the payment, they'll continue with collections. The CP3219A is basically saying "last chance before we really escalate this." Call the IRS (use one of the methods suggested above since getting through is a nightmare) and make sure: 1) your response was received, and 2) verify if your payment was received. If not, pay it ASAP. For future reference - stock sales are one of the biggest triggers for CP2000 notices because the basis reporting is so complicated. Always double check your 1099-B against the actual transactions.
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Donna Cline
ā¢Thanks for bringing this up - it's possible I didn't actually pay after responding. I sent back the response form agreeing to the amount, but now that I think about it, I don't remember if I included a check or if I was supposed to wait for a payment instruction. That could definitely be the issue. Has anyone here paid after responding to a CP2000? Did you include payment with your response or wait for them to send payment instructions?
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Caleb Bell
ā¢You generally have two options: you can include payment with your CP2000 response, or you can wait for the IRS to send you a bill after processing your response. If you chose the second option and they haven't processed your response yet, that's likely why you received the CP3219A. I'd recommend calling the IRS (using one of the methods others suggested to get through) and ask about the status of your case. Tell them you agreed to the CP2000 and want to pay the amount due immediately. They should be able to take your payment over the phone or give you instructions for paying online. Make sure to get a confirmation number for any payment you make.
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Danielle Campbell
Make sure you're calculating the correct cost basis for your stock sales. This is the #1 reason people get these notices for stock transactions. The IRS gets the sale price reported from brokerages but often doesn't get the correct purchase price, especially for employee stock options or RSUs. For the future, keep detailed records of all stock purchases, grants, and vesting schedules. The default basis reporting is frequently wrong for company stock plans and can trigger these kinds of notices.
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Rhett Bowman
ā¢This happened to me too. My company's stock admin platform reported the sales to my brokerage but the cost basis information didn't transfer correctly. The IRS only saw the proceeds and thought I made way more profit than I actually did. What a mess.
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