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For QSBS tracking specifically, make sure whoever prepares your taxes understands the documentation requirements. We had an SPV investment in a QSBS-eligible company, but when it came time to exit, we discovered our accountant hadn't maintained the proper documentation from day one to support the exclusion. Cost us a fortune in taxes that could have been avoided. Make sure your operating agreement specifically addresses QSBS tracking and that you keep meticulous records of the holding period for each investor.
This is so important! We had a similar issue where half our investors couldn't take full advantage of QSBS because the documentation wasn't right. Did you find any specific software or system that works well for tracking this?
One thing I'd add to this conversation is that you should also budget for potential audit defense costs. While SPVs with simple structures are less likely to be audited, the IRS has been focusing more on partnership returns lately, especially those involving investment activities. Even a simple audit can cost $2,000-5,000 in professional fees to handle properly. Consider getting audit protection insurance or setting aside a small contingency fund from your SPV for this possibility. It's not common, but when it happens, you don't want to be caught off guard with unexpected costs that have to be split among all the investors. Also, make sure your operating agreement clearly spells out how these ongoing compliance costs will be handled - whether they come out of the SPV's cash or are billed back to investors pro-rata. This prevents awkward conversations later when the annual tax bills come due.
I was wondering what kinda tax law lets Illinois hold onto your money for 3 months without paying interest. That's literally money you overpaid them that they're using interest-free. But whatever, glad you got it!
Same thing happened to me! Filed my IL return in February and the status page said "processing" for months. Then boom - refund showed up in my account last week with zero warning. The status STILL says processing even now. It's like their left hand doesn't know what their right hand is doing. At least we got our money but man, their system is completely broken. Would be nice to get some kind of notification when they actually send the refund instead of having to randomly discover it in your bank account!
Right?! It's so frustrating that there's literally no communication from their end. Like, would it kill them to send a simple email saying "hey, your refund is on the way"? Instead we're all just randomly checking our bank accounts hoping money magically appears. At least now I know for next year to just file and forget about it instead of obsessively checking that useless status page!
The whole "donation" thing is actually a pretty common misunderstanding. I've been making and selling jellies at farmers markets for years. Here's my practical advice: 1) Track EVERYTHING. Every egg, cup of flour, jar, label, even a portion of your electricity bill for running the oven. 2) Take lots of photos of your workspace and ingredients for documentation. 3) Open a separate bank account for your business income/expenses to make tracking easier. 4) Set aside 25-30% of what you make for taxes from day one. The good news is once you're properly set up, you'll likely owe less in taxes than you think because of all the legitimate deductions available to small food businesses.
Do you really need a separate bank account? I'm just starting out selling cookies at the farmers market and was planning to just keep a spreadsheet of sales and expenses. Is that not enough?
A separate bank account isn't legally required, but it makes your life SO much easier, especially if you ever get audited. When all your business transactions are mixed in with personal spending, it becomes a nightmare to sort through everything. Plus banks often have free business checking accounts for small operations. A spreadsheet is a good start for tracking, but having that clean separation between personal and business finances just makes everything more professional and organized. Even something simple like a basic checking account at a credit union can work - you don't need anything fancy when you're just starting out.
Adding to what everyone's said about the "donation" approach - I learned this lesson with my homemade pasta business last year. The IRS specifically looks at whether there's a "quid pro quo" relationship (you give bread, they give money), regardless of what you call it. Even if you put up a sign saying "free bread, donations appreciated," if people consistently pay you for specific loaves, that's income. One thing that helped me was starting small and keeping meticulous records from day one. I use a simple app to photograph every receipt and track mileage to farmers markets. Also, don't forget you can deduct things like recipe testing ingredients and even a portion of your phone bill if you're using it for business communications. The cottage food laws vary wildly by state too - some allow online sales, others don't. Some have income caps (like $50K/year max), others don't. Definitely worth checking your state's agriculture department website before you scale up. Good luck with the sourdough venture!
This is maybe a dumb question but what if i start a small side business just to be able to deduct my phone? like selling stuff on ebay once a month or something? would that work?
That's not a dumb question, but it could create some issues. If you start a business solely for tax deductions, the IRS might classify it as a hobby rather than a legitimate business. For a business to be recognized for tax purposes, you generally need to show that you're pursuing it to make a profit, not just for tax benefits. The IRS has a "hobby loss rule" where if you don't show a profit in at least 3 out of 5 consecutive years, they may disallow your business deductions.
Great question! I dealt with this exact situation last year when I was trying to figure out phone deductions. As others have mentioned, the Tax Cuts and Jobs Act really changed the game for W-2 employees - those miscellaneous itemized deductions are off the table until at least 2025. Since you mentioned you're a regular W-2 employee, your best bet is definitely to approach your employer about reimbursement first. Many companies are willing to provide a monthly stipend once they understand the business need - especially if you can document how much you're using your phone for work calls, emails, and navigation. If that doesn't work out, you might want to consider if you have any side income that could qualify as self-employment. Even small amounts of freelance work, consulting, or selling items online could potentially allow you to deduct the business portion of your phone expenses on Schedule C. Just make sure any side business is legitimate and profit-motivated, not just set up for tax purposes. The separate phone plan idea is smart for keeping things organized, but unfortunately won't change the deduction rules for your W-2 employment. Hope this helps clarify things!
Felix Grigori
Be advised that correspondence audits typically have a response deadline of 30 calendar days from the date printed on the notice, not from when you receive it. In a situation I encountered last tax season, the CP75 notice arrived 18 days after the issue date due to USPS routing delays, leaving only 12 days to compile documentation. The IRS Taxpayer Advocate Service has acknowledged these timing issues but has not implemented procedural changes to address them. Consider requesting an extension immediately upon receipt of the notice if you require additional time.
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QuantumQuasar
As someone who's dealt with IRS correspondence delays before, I'd recommend calling the IRS practitioner priority line if you have representation, or the general taxpayer line at (800) 829-1040 to confirm they have your correct mailing address on file. Sometimes audit notices get delayed or lost due to address discrepancies in their system. Also, since you mentioned not being a US citizen by birth, make sure you have documentation ready for any foreign accounts, income, or tax treaty benefits you may have claimed - these are common audit triggers. The 30-day response window starts from the notice date, not when you receive it, so time could be ticking even if the letter hasn't arrived yet.
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Connor Murphy
ā¢This is really helpful advice about calling to verify your address! I had a similar issue where the IRS had an old address from a previous return, and my audit notice went to the wrong place initially. The address verification tip is especially important for non-citizens who might have moved recently or have complex address histories. One thing to add - when you call, have your Social Security Number and a copy of your most recent return handy, as they'll need to verify your identity before discussing your account. The wait times can be long, but it's worth it for peace of mind about timing and next steps.
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