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Couple things to add from my experience with NSOs: 1) Consider the risk! You're putting real money into a private company that might never go public or get acquired. I exercised options at a startup that later failed - lost $15k and still had to pay taxes on phantom income. 2) If you wait till after IPO, there's usually a 180-day lockup period where you can't sell shares even though they're public. Market could tank during that time. 3) Ask if your company offers early exercise with 83(b) election - lets you exercise unvested options and starts your capital gains clock earlier. 4) Don't forget state taxes! California especially kills you on this stuff. 5) Some companies have programs to help with exercise costs or cashless exercises. Worth asking about.
The 83(b) election thing saved me a ton! My company allowed early exercise and I filed the 83(b) within the 30-day window. Paid very little tax up front since the FMV was close to strike price then. When we got acquired 2 years later, everything was long-term capital gains. Colleagues who didn't do this paid WAY more in ordinary income tax.
This is exactly the kind of situation where having all the right information upfront makes a huge difference. Based on your numbers (7,250 total options with those strike prices vs $5.93 FMV), you're looking at roughly $36k in taxable income if you exercise everything at once - that's a significant tax bill to plan for. A few practical considerations for your timeline: 1) Get clarity on your vesting schedule and any acceleration clauses that might trigger at IPO. Sometimes unvested options accelerate when companies go public. 2) Find out your company's IPO timeline. If it's 6+ months away, you might have time to exercise in stages across tax years to manage the tax hit. 3) Ask your company about any employee programs they offer - stock loan programs, cashless exercise options, or even tax gross-up assistance (some companies help cover the tax burden). 4) Consider your personal financial situation. Can you afford both the exercise cost (~$4,600 total) AND the tax bill on ~$36k of ordinary income? Don't put yourself in financial hardship for equity that's still speculative. The fact that your current tax advisor seems out of their depth is concerning. This really calls for someone with specific equity compensation experience, whether that's a specialized CPA or getting direct guidance from the IRS on proper reporting requirements.
This is such a comprehensive breakdown - thank you! The $36k taxable income calculation really puts things in perspective. I hadn't fully grasped that I'd be paying ordinary income tax rates on that entire amount. Your point about vesting acceleration at IPO is something I need to investigate immediately. I just assumed my unvested options would stay on their current schedule, but if they all vest at IPO, that could completely change my tax planning strategy. The timeline question is crucial too. I've been getting mixed signals from leadership about when we'll actually go public - some say Q3, others hint at early next year. If it's the latter, spreading exercises across tax years could save me a lot. I'm definitely going to ask HR about employee programs tomorrow. I had no idea companies sometimes offered stock loans or tax assistance for these situations. Even a cashless exercise option would help with the upfront cash requirements. You're absolutely right about needing specialized help. My current tax guy keeps saying "we'll figure it out" but that's not giving me the confidence I need for a decision this big. Time to find someone who actually deals with equity comp regularly.
Has anyone had their FSA administrator reject expenses during an audit because the provider didn't have a tax ID? I'm in a similar situation with a small home daycare and worried my company might make me pay back the FSA money if they audit and find out the provider wasn't properly registered.
Your FSA administrator generally only cares that you had eligible expenses for dependent care, not whether the provider was properly registered. As long as you have receipts showing you paid for childcare while you were working, that's typically sufficient for FSA purposes. The tax ID requirement is more about IRS reporting.
I went through almost the exact same situation two years ago with a home daycare that suddenly shut down. What really helped me was keeping a detailed timeline of everything - when I paid, when they closed, when I tried to contact them, etc. One thing I'd add to the great advice already given: check with your state's licensing board for childcare providers. Even if the daycare was operating without proper licensing, they might have records or complaints filed that could help you track down the owner's information. In my case, I found out through the state board that several parents had filed complaints when the daycare closed, and they actually had the owner's SSN on file from a previous licensing attempt. Also, don't stress too much about the FSA side of things. Your FSA administrator approved the reimbursement based on valid receipts for childcare expenses. The fact that the provider may have had licensing issues doesn't retroactively make your childcare expenses ineligible. You legitimately paid for childcare so you could work - that's what matters for FSA purposes. Just make sure to document everything thoroughly and you should be fine on both the FSA and tax filing fronts!
This is really helpful advice about checking with the state licensing board! I hadn't even thought about that angle. It's reassuring to hear from someone who actually went through this and came out okay on both sides. One quick question - when you found the owner's SSN through the state board, were you able to get that information directly or did you have to jump through hoops? I'm wondering if it's worth the effort to pursue that route or if I should just stick with the "PROVIDER REFUSED" approach that others have mentioned. Also, did you end up getting audited or having any follow-up issues with either the IRS or your FSA? Just trying to gauge what the realistic chances are of this becoming a bigger problem down the road.
Just a heads up about Washington state - while they don't have income tax, if you're doing any kind of consulting or business work while there (not just regular employment), you might be subject to their Business & Occupation tax. Caught me by surprise when I was working remotely from Seattle for a few months.
This! I got hit with an unexpected B&O tax bill because I didn't realize my freelance work counted even though I was only temporarily in Washington. Make sure you're tracking what type of work you're doing in each location.
This is such a complex situation, but you're definitely not alone in dealing with multi-state tax issues! Based on what you've described, Colorado sounds like it remains your domicile since that's where your official documents and permanent ties are. One thing I'd recommend is keeping detailed records of your travel dates and work locations going forward - this will be crucial for calculating income allocation between states. You can use a simple spreadsheet or even a phone app to track which days you're working where. Also, don't panic about the withholding situation. Even if Colorado was the only state withholding taxes, you can often claim credits on your Colorado return for any taxes you end up owing to Arizona as a non-resident. This prevents double taxation on the same income. Since you mentioned you can't afford a tax professional right now, consider looking into VITA (Volunteer Income Tax Assistance) programs in your area. They provide free tax help and many volunteers are trained to handle multi-state situations. The IRS website has a locator tool to find VITA sites near you.
The VITA program suggestion is excellent! I used VITA last year when I had a similar multi-state mess and they were incredibly helpful. The volunteer I worked with had experience with complex residency situations and walked me through everything step by step. One tip - when you call to make an appointment, specifically mention that you have multi-state tax issues. Some VITA sites have volunteers who specialize in more complex returns, and they can make sure you're matched with someone who has the right expertise. Also, start gathering all your documentation now - pay stubs, any state tax documents, records of where you were living/working throughout the year. Having everything organized will make the process much smoother whether you go with VITA or end up using one of the online tools others have mentioned.
Here's a systematic approach to determine if you need to amend: 1. Check if you received Premium Tax Credits (Form 8962) 2. If yes, verify if the 1095-C shows you were eligible for employer coverage 3. If you were eligible for employer coverage AND received tax credits, you need to amend 4. If you didn't claim tax credits, no amendment needed 5. Keep the 1095-C with your tax records for at least 3 years Alternatively, you could file Form 8275 (Disclosure Statement) with your next year's return explaining the situation, though this is usually unnecessary for 1095-C issues.
I went through this exact scenario two years ago and can share what I learned. The key thing to understand is that the 1095-C serves as documentation for the IRS to verify that you had minimum essential coverage, but it's not something you typically need to include with your return unless you're claiming Premium Tax Credits. What I'd recommend doing is comparing the information on your 1095-C with how you answered the health insurance questions on your tax return. If you indicated you had employer coverage for the months shown on the form, and you didn't claim any Premium Tax Credits, then you're likely fine. The IRS already receives this information directly from your employer anyway. However, if there's a discrepancy - like the form shows you were offered coverage during months you claimed you didn't have access to employer insurance - then you might need to consider an amendment. But based on what you've described, it sounds like you're probably in the clear. Just keep the form with your tax records in case the IRS ever has questions later.
This is really reassuring to hear from someone who's actually been through this! I'm in almost the exact same boat - got my 1095-C yesterday and have been worrying about it all day. Quick question: when you say to compare the form with how you answered the health insurance questions, are you referring to the questions about having coverage each month? I think I answered those correctly, but now I'm second-guessing myself about whether I properly indicated it was employer coverage versus marketplace coverage.
Andre Dupont
Just to add to what others have shared - you might want to file Form 4506-T to request wage and income transcripts from the IRS. This won't give you the K1 directly, but it will show what's been reported under your SSN, which might help you identify if the partnership has actually filed and just not distributed your copy.
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Zoe Papanikolaou
ā¢This is good advice. I use this form all the time with clients. Just note that it might take a few weeks to get the information back from the IRS, so it's not an immediate solution for this filing season. But it could help you determine if the partnership is filing on time and just not giving you your copy, or if they're actually filing late with the IRS too.
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Oliver Schulz
I've been following this thread and wanted to share another angle that might help. If you're dealing with a consistently unresponsive managing partner, you might also consider reaching out to your state's Secretary of State office or equivalent business registration authority. Many partnerships are required to maintain current contact information and registered agents with the state. If your managing partner is deliberately withholding financial information that you're entitled to as a partner, this could potentially violate state partnership laws or the terms under which the business is registered. Additionally, if this is a limited partnership, there may be specific fiduciary duties that the general partner owes to limited partners regarding timely financial reporting. Some states have penalties for partnerships that fail to provide required financial information to partners. I'd also suggest keeping detailed records of all your attempts to get the K1 - dates, methods of contact, any responses (or lack thereof). This documentation could be crucial if you need to pursue legal remedies or if the IRS asks about your good faith efforts to obtain the information.
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