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Anyone have experience with how this all gets reported on your tax forms? Like which specific forms and schedules do you need to fill out when you exercise options and then later sell at a loss?
For the initial exercise, if they're NSOs, the income goes on your W-2 if done through your employer. If they're ISOs and trigger AMT, you'll need to fill out Form 6251. When you sell at a loss later, you'd report that on Schedule D and Form 8949. If you're dealing with AMT credits from previous years, you'd use Form 8801 to claim those credits.
This is a really helpful thread - I'm dealing with a similar situation but with one additional wrinkle. I exercised ISOs in early 2023 at a $200k valuation, but the company actually ended up shutting down completely in late 2023 before going public. So my shares are essentially worthless now. From what I'm reading here, I still owe AMT on the original $200k spread, but when I "sell" the worthless shares (or they're deemed worthless), I should be able to claim the full amount as a capital loss. The tricky part is figuring out exactly when and how to claim that loss - do I need to wait for some official declaration that the company is dissolved, or can I claim it as soon as it's clear the shares have no value? Also wondering if anyone knows whether worthless stock gets treated differently than stock sold at a loss for AMT credit purposes. This whole situation has been a tax nightmare!
I'm in the same boat with a 1099K from eBay. Does anyone know if I need to keep track of EACH item I sold separately? I sold like 200+ things throughout the year and didn't keep perfect records of the cost of every single thing. Some were just stuff from around my house. Is the IRS going to come after me??
For items you're selling from around your house (personal items), those are generally considered personal capital assets rather than inventory. If you sell them for less than you paid, you don't report the loss. If you sell for more than you paid, technically it's a capital gain. However, for a reselling business where you buy items specifically to resell, you should track cost of goods sold. If you don't have exact records for every item, you can use a reasonable method to estimate your costs. For example, you might use an average cost percentage based on the items where you do have records.
Don't panic - you're actually in a pretty manageable situation! I went through this exact same thing two years ago when I started selling pottery online and got my first 1099K. A few quick tips to ease your stress: 1. Your expenses are solid - materials, packaging, and tools are all legitimate business deductions. Keep those receipts organized! 2. For the home office, since you mentioned using your dining room table, that probably won't qualify for the deduction since it's not exclusively used for business. But don't worry - your other deductions will still help significantly. 3. The self-employment tax might seem scary, but remember it's calculated on your NET profit after expenses. So with $14,600 in sales minus your $6,860 in expenses, you're looking at roughly $7,740 in profit subject to SE tax. 4. For quarterly payments - if this is your first year with business income and you had sufficient withholding from your W-2 job to cover most of your total tax liability, you'll likely avoid penalties. Start with getting your Schedule C filled out with all your income and expenses. Most tax software will walk you through this step by step. You've got this! The first year is always the most overwhelming, but you're actually well-prepared with your expense tracking.
Has anyone actually gotten money back from SBTPG after all this? I've been fighting with them for 10 MONTHS over a $4,200 refund they claim they sent back to the IRS. IRS says they don't have it. I've filed all the forms, done the trace, called hundreds of times... still nothing. I'm about ready to file a lawsuit but don't know if it's even worth the money.
Yes, I actually did get my money back but it took hiring a tax attorney to send a formal demand letter. Cost me $300 but I got my $3,800 refund within 3 weeks after that. Before the attorney I spent 4 months getting nowhere. Sometimes these companies only respond when they realize you're serious about legal action.
Thanks for letting me know! I was worried a lawyer would cost more than my refund. Did you use a local attorney or is there a specific type that handles these SBTPG issues? I'm definitely at the point where I'll try anything.
I'm going through almost the exact same situation right now! Filed in February through TurboTax, bank account issues led to SBTPG getting my refund, and they've been giving me the runaround for months. They've told me my check was "in the mail" at least 6 times now with different dates each time. Reading through all these responses is really helpful. I had no idea about requesting the EFT refund notification letter - that sounds like crucial evidence to have. I'm definitely going to call and ask for that today using the exact phrase Oscar mentioned. @Hannah - have you had any luck getting through to the IRS recently? I've been trying for weeks but the hold times are insane. Might have to try that Claimyr service everyone's talking about since I can't afford to spend entire days on hold. The most frustrating part is that SBTPG acts like they're doing you a favor by eventually maybe sending your own money back. It's ridiculous that tax prep companies can partner with these banks that basically hold your refund hostage. There should be better regulations around this whole process.
I'm so sorry you're going through this too! It's honestly a relief to know I'm not the only one dealing with SBTPG's endless "check is in the mail" promises. I've actually been documenting every single call - dates, times, representative names, and what they promised each time. It's become quite the spreadsheet! I haven't been able to get through to the IRS yet either. After reading everyone's experiences here, I think I'm going to bite the bullet and try Claimyr. Spending another week on hold just to get disconnected again sounds like torture. That EFT notification letter Oscar mentioned sounds like exactly the ammunition we need against SBTPG. The whole system is broken when legitimate taxpayers have to jump through this many hoops just to get their own money back. I've started warning everyone I know to avoid TurboTax specifically because of their SBTPG partnership. At this point I'd rather pay H&R Block's higher fees than deal with this nightmare again. Keep fighting and document everything! Hopefully we'll both have our money soon.
Quick tip from someone who's been through this: wherever you are in the calendar, CALL ON TUESDAY OR WEDNESDAY MORNINGS! Monday = catching up on weekend emails Thursday/Friday = racing to finish weekly deadlines Afternoons = meetings and current client work When I called tax pros on Tuesday mornings around 10am, I got responses from 5 out of 6. When I tried Friday afternoons, 0 out of 4 called back.
Great question about timing! I just went through this process myself last year and learned some hard lessons. I'd actually add one more consideration to the great advice already shared: many tax professionals are also doing year-end tax planning consultations from November through December. So while September-October might be ideal for initial conversations, don't be surprised if they're busy again in November/December with existing clients. One thing that really helped me was being super prepared when I reached out. I had my previous year's tax return, a list of any changes in my situation, and specific questions ready. This showed I was serious and made it easier for them to quickly assess if they could help me. Also, don't overlook smaller, local firms. I initially only looked at big-name places and got nowhere. Found an amazing EA through a local business referral who had immediate availability and has been fantastic to work with. For investment income like you mentioned, definitely look for someone with specific experience in that area - ask them directly about similar clients they've worked with. It makes a huge difference in catching deductions and planning opportunities you might miss otherwise.
Melina Haruko
I went through this exact situation on February 28th of this year. Called and verified my identity after never receiving the letter. The representative told me everything was good to go, but my transcript and WMR didn't update until March 15th - that's 16 days later. Then my refund was deposited on March 22nd. The most frustrating part was calling back on March 7th when nothing had changed, and being told by a different rep that my verification hadn't been properly processed. Had to go through the whole verification process again! I recommend calling back on April 27th if you don't see any changes, just to confirm the verification was properly recorded in their system.
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QuantumQuest
I'm going through this EXACT same nightmare right now! Verified my identity over the phone 8 days ago and my transcript is still completely blank - it's like my tax return fell into a black hole. The rep assured me everything was good on their end, but clearly their system didn't get the memo. What's really frustrating is that I've been checking my transcript obsessively every morning like it's some kind of lottery ticket. The waiting is killing me because I need this refund to pay off my student loans before the grace period ends. Has anyone tried calling back to double-check that the verification was actually processed correctly? I'm wondering if I should wait the full 2-3 weeks or call sooner to make sure there wasn't a glitch. This whole system feels like it's held together with digital duct tape!
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