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Important point that nobody has mentioned yet - if you're regularly dealing with large cash transactions like this, you should consider setting up a more formal business structure and possibly getting a tax professional. Form 8300 requirements are just one aspect of cash business compliance - there are also state reporting requirements in some locations that kick in at different thresholds.
I've been operating as a sole proprietor so far, but you're right that things are getting more complicated as the business grows. Would an LLC provide better protection for this kind of business? And at what point would you say it's necessary to hire a tax pro rather than DIY?
An LLC would definitely provide better protection, especially since you're dealing with valuable merchandise and cash transactions. It helps separate your personal assets from business liabilities, which becomes increasingly important as your operation grows. For phone flipping specifically, an LLC can also provide some protection if issues arise with the phones after sale. I'd say the tipping point for hiring a tax professional is when you start dealing with reporting requirements like Form 8300 or when your annual revenue exceeds $25-30k. At that level, the potential tax savings and compliance protection a professional can provide typically outweigh their cost. They can also help structure your business optimally for tax purposes and ensure you're taking all legitimate deductions related to your inventory, shipping, and other business expenses.
One thing I haven't seen mentioned yet is that you should also be aware of the timing requirements for Form 8300. You have to file it within 15 days of receiving the cash payment (or the final payment if it's a series of related transactions). This is crucial because there are penalties for late filing, even if it's just a few days late. Also, don't forget that you're required to provide a written statement to the customer by January 31st of the year following the year you filed the form. Many small business owners miss this requirement, but it's just as important as filing the form itself. For your phone flipping business, I'd recommend setting up calendar reminders for both the 15-day filing deadline and the January 31st customer notification deadline. Missing these deadlines can result in penalties that really add up, especially if you're filing multiple forms throughout the year.
This is really helpful timing information! I had no idea about the 15-day deadline or the customer notification requirement. That January 31st deadline especially seems like something that would be easy to forget about. Do you happen to know what the penalties are if you miss these deadlines? And for the customer notification - is there a specific format or can it just be a simple letter explaining that you filed the form?
Maya, you're definitely not alone in this situation! The good news is that you're being proactive about fixing it. Based on what others have shared here, you should still be able to amend your 2019 return, though time may be getting tight depending on when you originally filed. For your $8,400 in freelance income, you'll need Form 1040-X to amend, plus Schedule C for the business income and Schedule SE for self-employment tax (which will be around 15.3% of your net earnings). Don't forget that you can also deduct legitimate business expenses from that freelance work - things like software subscriptions, equipment, even a portion of your home if you had a dedicated workspace. The key is to file as soon as possible. Since you're voluntarily coming forward, you have a much better chance of getting penalties reduced or waived, especially if you have a clean tax history. The IRS tends to be more lenient with people who self-report mistakes rather than those they catch through audits or matching programs. Keep all your payment records and any receipts for business expenses. The fact that you found these records while cleaning shows you weren't trying to hide anything - just document that timeline in case they ask. You've got this!
This is such great comprehensive advice, Freya! I just wanted to add that Maya should also check if any of her freelance clients issued 1099s for that work. If they did, the IRS probably already has those records in their system and might eventually match them to her return anyway. Getting ahead of it now is definitely the smart move. Also, Maya - when you calculate your Schedule SE tax, remember it's on your net earnings after business deductions, not the full $8,400. So definitely gather up those business expense records that Hunter mentioned. Every legitimate deduction helps reduce what you'll owe!
Maya, I went through almost the exact same situation last year with my 2020 return! I had forgotten about some consulting income and was terrified about the consequences. Here's what I learned from the experience: First, breathe - you're doing the right thing by coming forward voluntarily. The IRS really does treat self-disclosure much more favorably than when they catch unreported income through their matching systems. For your situation, you'll definitely need Form 1040-X, Schedule C for the freelance income, and Schedule SE for self-employment tax. But here's something important that others touched on - make sure you're calculating your NET earnings for the SE tax, not the gross $8,400. Any legitimate business expenses you had (software, equipment, even mileage to client meetings) can reduce that amount. I ended up owing about $1,800 in additional tax plus interest, but I successfully got the penalties waived through first-time abatement. The key was explaining in my cover letter that it was an honest oversight, not intentional tax avoidance. One practical tip: gather your documentation now while you're motivated. I procrastinated for months out of anxiety, which just made the interest accrue longer. The sooner you file the amendment, the sooner the interest stops growing. You've got this! The hardest part is realizing the mistake - fixing it is actually pretty straightforward.
Daniel, thank you so much for sharing your experience - it's incredibly reassuring to hear from someone who went through the same thing! Your point about calculating NET earnings for SE tax is really important. I'm definitely going to dig through my records to find every legitimate business expense I can. I'm curious about the cover letter you mentioned - did you send that along with your Form 1040-X? What kind of details did you include to explain it was an honest mistake? I want to make sure I present my situation in the right way when I file the amendment. Also, when you requested the first-time abatement, did you do that immediately with your amendment or wait to see if they assessed penalties first? I'm trying to figure out the best timing for everything.
Has anyone noticed if certain tax software seems to have more or fewer of these "system issues"? I used TurboTax and I'm stuck in limbo too. Wondering if I should use something else next year.
I'm dealing with the exact same issue! Filed on February 2nd, accepted February 5th, and it's been radio silence since then. Called the IRS last week and got the same "system issue" explanation with the 10-week timeline. What's really frustrating is that when I check my tax transcript online, it shows my return was received but there are no processing codes or updates at all - just blank. It's like my return disappeared into a black hole somewhere in their system. I've been reading through all these comments and it seems like there are multiple different issues causing delays this year - some are identity verification, some are document mismatches, some are random reviews. The problem is the IRS phone reps either don't know or won't tell you which specific issue is affecting your return. Really considering trying one of those transcript analysis tools mentioned here since I need this refund for some urgent home repairs. At this point I just want to know WHAT is actually wrong instead of getting the generic "system issue" runaround.
Based on my experience working with several clients in similar situations, the TAS has become much more responsive to hardship cases in 2024 compared to previous years. I've seen them accept cases as early as 2-3 weeks after amendment filing when proper documentation was provided. The key is submitting Form 911 with comprehensive documentation of your hardship AND proof that you've attempted to resolve through normal channels. I recommend calling the TAS intake line directly at 877-777-4778 rather than the general IRS line, as they can better assess your situation.
One little trick I learned from my tax saga last year - when you call that TAS number, make sure to have your transcript access verification code ready to go! Saves about 20 minutes of back-and-forth. Also, if you're dealing with a home repair emergency, some localities have emergency repair assistance programs that might bridge the gap while waiting for your tax situation to resolve. Might be worth checking with your county services office... sometimes the help comes from places you wouldn't expect! š
I went through almost the exact same situation two years ago with a burst pipe that flooded my basement right after filing an amended return. Here's what worked for me: I called the TAS line (877-777-4778) and explained that I had immediate housing safety concerns due to water damage. The key was having documentation ready - photos of the damage, repair estimates, and a letter from my insurance company showing the coverage gap. They accepted my case within 5 days of filing Form 911 because I could demonstrate that the water damage posed health risks and I couldn't afford repairs without my refund. Don't let anyone tell you that you have to wait months - if you have genuine hardship with proper documentation, TAS can act quickly. The whole process took about 6 weeks from when they accepted my case to getting my refund. Stay persistent and document everything!
This is exactly the kind of real-world advice I was hoping to find! Connor, thank you so much for sharing your experience. I'm dealing with similar water damage issues and the documentation angle makes total sense. Quick question - when you say "health risks," did you need any kind of official assessment or was your own documentation with photos sufficient? My plumber mentioned potential mold concerns with the water intrusion, and I'm wondering if that kind of statement would help strengthen my case. Also, did TAS actually expedite your amendment processing or did they just prioritize your case within their system?
Sean Doyle
I'd really recommend taking a basic small business tax course. I did one at my community college for like $75 and it was soooo worth it. LLC taxation isn't actually that complicated once someone explains it to you in plain English. Also, get a separate business bank account ASAP if you haven't already! Makes tracking business income and expenses 1000% easier come tax time. I learned that lesson the hard way my first year lol.
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Zara Rashid
ā¢Second this! Mixing personal and business finances is a nightmare at tax time. Plus it can potentially jeopardize your liability protection, which is a big reason for having an LLC in the first place. It's called "piercing the corporate veil" when you treat business assets like personal ones.
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Haley Bennett
As someone who went through this exact same confusion when I started my LLC two years ago, I totally feel your pain! Here are the key things I wish someone had told me upfront: 1. **Get that EIN immediately** - Even though Isabella mentioned you don't technically need one as a single-member LLC, get it anyway. It's free, takes 5 minutes online, and you'll need it for your business bank account (which you absolutely should open ASAP). 2. **Start making quarterly payments NOW** - With $42k in revenue, you're definitely going to owe taxes. The IRS wants 25% of last year's tax liability or 90% of this year's. Since this is your first year, estimate around 25-30% of your profit for federal taxes plus self-employment tax. 3. **Track EVERYTHING** - That laptop and hosting are definitely deductible. So are your phone bill (business portion), internet, office supplies, software subscriptions, even mileage to meet clients. I use a simple spreadsheet or app like QuickBooks Self-Employed. 4. **Home office deduction** - If you use part of your home exclusively for business, you can deduct it. Either use the simplified method ($5/sq ft up to 300 sq ft) or calculate actual expenses. The Schedule C really isn't that scary once you see it - it's just business income minus business expenses equals profit, then that profit goes on your 1040. You've got this!
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