Does anyone know if there's a way to access your W-2 online if you haven't received it in the mail yet? My employer mentioned something about an online portal but didn't give details and now they're not responding to emails. Getting worried since the filing deadline is coming up.

Don't stress too much about this - it's actually pretty straightforward once you understand what each copy is for! As others have mentioned, you don't need to fill anything out on the W-2 forms themselves. Your employer has already done that. Here's a quick summary to help clarify: - If you're filing electronically (which I'd recommend for your first time), you'll just enter the information from your W-2 into the tax software - Keep Copy C for your personal records - store it somewhere safe with your other important documents - The other copies are mainly needed if you're filing paper returns, which most people don't do anymore Since this is your first time, I'd suggest using reputable tax software like TurboTax, H&R Block, or FreeTaxUSA. They'll walk you through everything step by step and ask you simple questions rather than expecting you to know tax terminology. Most of them are free for simple returns with just W-2 income. The most important thing is to make sure you enter all the numbers from your W-2 correctly into whatever software you choose. Double-check everything before submitting!

Has anyone used any of those equity financing companies like SecFi or ESO? I'm considering one to cover my exercise costs but worried about what I'm giving up in the long run.

I went through something similar with my startup equity in 2022. One thing to consider that hasn't been mentioned yet is the potential wash sale rules if you're also trading in your company's stock through secondary markets or employee stock purchase plans. Also, given your company's current situation (70% drop in valuation), you might want to look at Section 1202 qualified small business stock (QSBS) benefits. If your company qualifies, you could potentially exclude up to $10 million in gains from federal taxes when you eventually sell. This is another reason why exercising now at the lower FMV could be beneficial - it starts your 5-year holding period clock for QSBS. The key is making sure you have enough liquidity to cover both the exercise costs ($36,400 for 28,000 shares) and the tax bill (roughly $1.36M in ordinary income assuming you're in a high tax bracket). Don't forget about state taxes too - they can add significantly to your bill depending on where you live. Have you considered doing a partial exercise strategy? Maybe exercise 25% of your vested shares now to start the capital gains clock, then reassess in 6-12 months based on how the company is performing?

Just want to add another perspective here - I'm a tax preparer and see this situation fairly often. The IRS is pretty strict about the "who paid" rule, but there are a few nuances worth mentioning: 1) If your parents paid the medical provider directly but you had already given them the money (even if it was earlier), YOU are considered to have paid and can deduct it. The key is having documentation showing the money flow. 2) For future reference, if family wants to help with medical bills, it's better tax-wise for them to give you the money first, then have YOU pay the provider. That way you maintain the deduction eligibility. 3) Don't forget that medical expenses include more than just the surgery - prescription drugs, medical equipment, travel costs to medical appointments, etc. Sometimes people miss these smaller items that can add up. Given that this happened last year and your parents paid directly, your best bet might be to see if they would benefit from itemizing their deductions instead of taking the standard. Even if they normally don't itemize, a large medical expense might push their total itemized deductions above the standard deduction threshold.

I'm dealing with a similar situation right now where my spouse paid for my dental work last year. Reading through all these responses has been super helpful! It sounds like the key takeaway is that the IRS really does focus on who physically made the payment, not who received the medical care. For anyone in this situation, it seems like the main options are: 1) having the person who paid consider itemizing their deductions if it makes sense for their tax situation, 2) properly documenting any legitimate loan arrangements going forward, or 3) in future cases, having the family member give you the money first so you can pay the provider directly. The reimbursement option that Yara mentioned is something I hadn't considered either. It's probably too late for most of us with 2024 expenses, but definitely good to keep in mind for this year's medical costs. Thanks to everyone who shared their experiences and especially to the tax preparer for the professional insights. Sometimes these family financial help situations create more complexity than we realize!

This is a really common issue that catches people off guard! The good news is you'll definitely get that withheld tax back when you file your return. Just make sure to include the amount from Box 4 of your 1099-INT on line 25 of your Form 1040. For such a small interest amount, the withholding was almost certainly triggered by either a missing/incorrect SSN on file with your bank, or a name mismatch between your bank account and IRS records. I'd suggest calling your bank to verify they have your correct information on file - you might need to submit a new W-9 form to fix it for next year. The withholding rate for backup withholding is 24%, so if you earned $135 in interest, they probably withheld around $32. You should see this exact amount in Box 4 of your 1099-INT form.

Just wanted to add that if you're still having trouble getting through to the IRS or your bank to resolve this, don't get discouraged! Backup withholding issues are actually pretty straightforward to fix once you know what caused them. A few additional tips from my experience: - Keep a copy of any corrected W-9 you submit to your bank for your records - If this happened with one bank, check any other accounts you have - sometimes the same name/SSN issue affects multiple institutions - The corrected information usually takes 1-2 statement cycles to take effect, so don't panic if you see withholding on your next month's interest And definitely don't forget to claim that $32 on your tax return! It's essentially a prepayment of your taxes, so you'll either get it back as a refund or it'll reduce what you owe. For such a small amount of interest income, you'll almost certainly get the full amount back.

Curious - does anyone know if there's an easy way to estimate how much I should set aside from my tips for taxes? I'm in a similar situation (bartender, no tip reporting by employer) and I'm trying to avoid a huge bill at tax time.

I'm dealing with something similar at my restaurant job. What really helped me was creating a simple daily tip log - I just write down my total tips each shift (cash + credit card) in a small notebook I keep in my car. Takes 30 seconds but gives me solid records. One thing I learned is that even though your employer isn't handling this correctly, the IRS still expects you to pay quarterly estimated taxes if you're going to owe more than $1,000 at the end of the year. Since tips aren't being withheld from, you might want to look into making quarterly payments to avoid penalties. You can use Form 1040ES to calculate and pay these. Also, keep track of any work-related expenses you can deduct - things like non-slip shoes, uniforms, or even a portion of your phone bill if you use it for work. Every little bit helps offset the extra tax burden from having to pay both sides of the FICA taxes on your unreported tips.