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Lot of good advice here but nobody has mentioned the importance of the LLC Operating Agreement! That document should specify your actual status in the company and might clarify if you're supposed to be treated as a member, manager, employee or some combination. Request a copy ASAP if you don't already have one. Also, if they're paying you from a different entity than the one you work for, that could indicate they're using a Professional Employer Organization (PEO) or some kind of employee leasing arrangement, which is actually pretty common and not necessarily shady. But if that's the case, they DEFINITELY should be withholding taxes!
This is good advice. I'd also recommend checking if the LLC is treated as a "disregarded entity" for tax purposes, which is common for single-member LLCs. The tax treatment would flow through to the owner in that case, which complicates things further.
Excellent point about disregarded entities. If it's a single-member LLC being treated as a disregarded entity, then the tax situation gets even more complex. In that case, the company would be taxed as a sole proprietorship, and the owner would generally be unable to be classified as an employee of their own company for tax purposes. But given that the OP mentioned "profit units" that vest, it sounds more like a multi-member LLC with some kind of equity compensation structure. In that case, the LLC operating agreement would be absolutely crucial to understand exactly what those "profit units" represent in terms of actual ownership.
This situation has several red flags that suggest potential tax fraud or worker misclassification. The fact that they're claiming you as an employee for COVID relief purposes while simultaneously refusing to withhold taxes is particularly concerning - that's essentially having it both ways for their financial benefit. Here's what I'd recommend doing immediately: 1. **Document everything** - Save all contracts, pay stubs, emails about your status, and any communications regarding the COVID relief claims. Screenshot or print anything that might disappear. 2. **Request your LLC documentation** - Get copies of the Operating Agreement, any amendments, and confirmation of the LLC's tax election (partnership vs. corporation). You have a right to this information as a purported member. 3. **Calculate your potential tax liability** - Since no taxes have been withheld, you're likely on the hook for both income taxes AND self-employment taxes (15.3%) if you're truly classified as a self-employed LLC member. This could be a substantial amount. 4. **Consider professional help** - This situation is complex enough that you might want to consult with both a tax professional and an employment attorney. Many offer free consultations and can help you understand your rights and obligations. The discrepancy between your "employment contract" language and their current claims about your status, combined with the different payment entity and COVID relief issues, suggests this company may not be handling worker classification properly across the board.
This is really comprehensive advice, thank you! I'm especially concerned about point #3 regarding the tax liability. If I've been getting paid since October 2023 without any tax withholding, am I looking at penalties for not making quarterly estimated payments? I had no idea I might be responsible for self-employment taxes on top of regular income tax - that 15.3% rate is scary when applied to months of back pay. Should I be setting aside money now for what I might owe, or is there a chance this gets resolved in my favor if it turns out I should have been classified as an employee all along?
Great question! I went through an audit two years ago and can share what I learned firsthand. The IRS absolutely accepts digital receipts - in fact, the agent I worked with seemed to prefer them because they were clearer and more organized than my faded paper receipts. What matters most is that your receipts contain the "big four" pieces of information: date, amount, vendor name, and business purpose. Whether it's a PDF emailed receipt, a photo of a paper receipt, or a scanned copy doesn't matter as long as it's legible and complete. Regarding third-party verification - they didn't contact any of my vendors during my audit, but the agent did mention they could if needed. From what I understand, they typically only do this for larger amounts or if something seems inconsistent in your documentation. One tip that saved me: I started writing the business purpose directly on receipts (or in the filename for digital ones) right when I get them. Things like "office supplies for Q3 project" or "client meeting lunch with John Smith." This made the audit process much smoother because I didn't have to remember months later what each expense was for. Your anxiety about being prepared is actually a good thing - being organized ahead of time makes all the difference if you ever do get selected for an audit!
This is really reassuring to hear from someone who actually went through it! I've been paranoid about my record-keeping but sounds like I might be overthinking it. Quick question - when you write the business purpose on receipts, do you do this for literally every single expense? Even something obvious like "office supplies" from Staples? And for digital receipts, do you rename the actual file or just keep notes somewhere else?
@a5ec92485497 I do this for pretty much every business expense, even the "obvious" ones! You'd be surprised how many times I've looked at a receipt months later and couldn't remember if those office supplies were for my home office or my kid's school project. For digital receipts, I rename the files to include the business purpose - something like "2024-03-15_Staples_OfficeSupplies_ClientProjectMaterials.pdf". It takes an extra 30 seconds but makes finding things so much easier later. For receipts I photograph, I either write on them before taking the photo or add the info in my phone's photo description right away. The IRS agent actually complimented my organization system during the audit and said it made their job much easier, which I think worked in my favor. Better to over-document than under-document!
I've been through a couple of audits over the years and wanted to add one important point that hasn't been mentioned yet - make sure your digital receipts are stored in a format that won't become obsolete. I had some receipts saved in an old proprietary format that became difficult to open years later. Also, for anyone using smartphones to photograph receipts, make sure the images are high quality and well-lit. I've seen people get tripped up because their phone photos were too blurry to read clearly. The IRS needs to be able to see all the details - amount, date, vendor, what was purchased. One more tip: if you pay cash for business expenses (which I try to avoid), always ask for a receipt and make sure it shows the business name and tax ID if possible. Hand-written receipts from small vendors are fine as long as they contain the required information, but they need to look legitimate and professional.
This is such great advice about file formats! I never thought about receipts becoming unreadable due to outdated formats. What file types do you recommend for long-term storage? I've been saving everything as PDFs, but wondering if there's something better. Also, your point about cash receipts is really helpful. I occasionally pay cash at small local businesses and some of their handwritten receipts are pretty informal. Should I be asking them to include specific information, or is it okay to write additional details on the receipt myself after the transaction?
Just wanted to add one more practical tip from my experience - make sure to keep copies of everything! When my parents gifted me money for my house, I created a folder with copies of the gift letter, bank transfer records, their Form 709s, and even screenshots of the IRS annual exclusion amounts for that year. This documentation became super helpful not just for the mortgage process, but also when I was doing my own taxes the following year. My tax software kept asking about large deposits, and having everything organized made it easy to show it was a documented gift. Plus, if you ever get audited down the road (unlikely, but still), you'll have a complete paper trail showing everything was done properly. The house buying process is stressful enough without worrying about tax compliance - sounds like you're being smart by researching this ahead of time!
This is such excellent advice about documentation! I'm definitely going to create a dedicated folder for all of this. Quick question - when you mention screenshots of the IRS annual exclusion amounts, where exactly did you find the official numbers? I want to make sure I'm referencing the right source since I've seen slightly different numbers on different websites. Also, did your tax software actually flag the large deposit as suspicious, or was it just a routine question? I'm wondering if I should give my tax preparer a heads up about the gift when I file next year, or if it's something that would come up naturally in the process. Thanks for sharing your experience - it's really helpful to hear from someone who's been through this whole process!
For the official IRS annual exclusion amounts, I always go directly to IRS.gov and search for "annual gift tax exclusion" - they publish the current year amounts in their gift tax guidance. You can also find it in IRS Publication 559. I screenshot the relevant page with the date visible so there's no question about what the limits were for that specific tax year. The tax software didn't flag it as suspicious, it was just a routine question when I entered my bank statements. Most tax software asks about large deposits to make sure you're not missing any taxable income. It's definitely worth giving your tax preparer a heads up though - they'll appreciate having the context and it'll make the process smoother. @b4a6d22b863d One more tip - if you use banking apps that categorize transactions, go ahead and label the deposit as "gift from family" or something similar. It's just another small piece of documentation that shows everything was handled properly!
This is such a comprehensive thread - thank you everyone for sharing your experiences! I'm actually in a very similar situation where my parents want to help with my down payment, but I had no idea about the Form 709 requirement or the gift splitting option. One thing I'm curious about that I haven't seen mentioned yet - are there any state tax implications to consider? I know gift taxes are federal, but I'm wondering if some states have their own gift tax rules that might affect this kind of family transfer. My parents live in a different state than where I'm buying the house, so I want to make sure I'm not missing anything on the state level. Also, for those who have been through this process, how far in advance did you start the paperwork? I'm hoping to buy in about 6 months and want to make sure we have enough time to get everything properly documented before I start the mortgage application process.
Great question about state taxes! The good news is that most states don't have their own gift taxes - only Connecticut and Minnesota currently impose state-level gift taxes, and even then they have pretty high exemption thresholds. Since you mentioned your parents live in a different state, you'll want to check the specific rules for their state of residence, but chances are you won't have any additional state tax obligations. As for timing, I'd recommend starting the paperwork process at least 2-3 months before you plan to apply for your mortgage. This gives you time to get the gift letter templates from your lender, coordinate the timing of the actual money transfer, and handle any Form 709 filings if needed. Plus, some lenders do want to see the funds "seasoned" in your account for 30-60 days before closing. One thing I learned is that it's actually easier to have these conversations with lenders early in the process rather than springing it on them later. Most loan officers deal with family gift situations regularly and can walk you through their specific documentation requirements upfront. This way you can make sure your parents structure everything exactly how the lender needs it documented. @63ea3716295c You're being really smart to plan this out 6 months in advance - that's plenty of time to get everything organized properly!
I've been doing my own business taxes for my small craft shop for 3 years now. My advice: if you have a simple situation with clear income/expenses, absolutely do it yourself. Just make sure you: 1) Keep ALL receipts (paper or digital) 2) Track mileage if you use your car for business 3) Separate business/personal expenses completely 4) Set aside at least half a day to do your taxes carefully I learned the hard way that rushing through leads to mistakes. For your first year with minimal revenue, a CPA probably isn't worth the $300-500 they'll charge.
What about quarterly estimated taxes? Do you have to file those for a small business even in your first year?
For your first year in business, you generally get a pass on penalties for not making quarterly estimated tax payments. The IRS has a "safe harbor" provision where if you had no tax liability last year, you won't be penalized for not making estimated payments this year. However, starting your second year, you'll likely need to make quarterly payments if you expect to owe $1,000 or more in taxes. The tax software will help calculate what you should pay each quarter. I set calendar reminders for all four quarterly due dates so I don't forget - they're not on the normal tax deadline schedule!
I tried using TurboTax for my first year in business and ended up missing so many deductions. When I finally used a CPA the next year, she found over $2,000 in deductions I'd missed! Just saying sometimes paying a pro is worth it.
What kinds of deductions did you miss? Now I'm worried I've been leaving money on the table with my side hustle...
Aisha Abdullah
One thing to consider is that the situation might get more complicated if your royalty income continues to grow. Once you start getting into larger amounts ($10k+), some US companies get more strict about tax compliance. I'm a composer in Brazil and my initial small royalty payments were handled exactly like yours - no withholding, no forms. But when I had a track used in a popular show and my payments jumped to $12k, suddenly the distribution company got very concerned about proper documentation! They retroactively requested W8-BENs and threatened to withhold 30% from future payments until I complied.
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Ethan Davis
β’Same thing happened to me! My game music suddenly took off and the US company panicked about tax forms they should have been collecting all along. Did you end up having to file US returns for those previous years?
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Javier Torres
This is actually a really important point about being proactive before your income grows. I'm a songwriter in the UK dealing with something similar - started small with streaming royalties but now getting sync placements that are pushing my US income much higher. What I learned is that even though the treaty protects you from owing tax, you still want to establish proper documentation early. I sent W8-BEN forms to all my US distributors even when they hadn't asked, and kept certified mail receipts as proof. When my income jumped last year and they suddenly got worried about compliance, I already had everything in place. The key is not waiting for them to figure out their obligations - take control of your own documentation. It's much easier to send the forms now when the amounts are smaller and there's no pressure, rather than scrambling when they panic over larger payments and threaten to start withholding at 30%.
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