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Has anyone considered the alternative minimum tax (AMT) implications here? When I exercised my ISOs a few years ago, I got absolutely destroyed by AMT because the paper gains pushed me over the threshold. I know NSOs are different since you pay ordinary income tax upfront rather than AMT, but the large income spike from a single exercise could still trigger other tax issues like phase-outs of deductions or credits.
AMT usually hits harder with ISOs than NSOs. With NSOs, you're paying ordinary income tax on the spread at exercise, which actually counts toward your regular tax and AMT equally. But you're right about the income spike - it can push you into higher brackets and phase out other benefits. One strategy I've seen is exercising across December/January to split the income between two tax years. Just be super careful about properly documenting the FMV at each exercise date since you're dealing with a private company valuation.
Another consideration worth mentioning - check if your option agreement has any restrictions on early exercise or transfer. Some private companies include provisions that let them repurchase your shares at cost if you leave the company within a certain period after exercise, which could wipe out the tax benefit you're trying to capture. Also, with a 409a valuation at $8 and projected IPO at $120, there's significant appreciation still expected. You might want to model out different scenarios - what if the IPO gets delayed or the valuation comes in lower than expected? The tax optimization has to be balanced against execution risk. One middle-ground approach: exercise enough options now to establish some cost basis at the current $8 valuation, then use cashless exercise for the remainder at IPO. This gives you some tax efficiency while limiting your cash outlay and risk exposure.
I got mine at 5:15 Eastern! DDD 3/12 with SunTrust. Maybe check again?
Just checked again and still nothing in my Chase account. Hopefully it comes through tonight!
I'm in the exact same boat - 3/12 DDD with Chase and nothing yet! I've been refreshing my account all day like it's going to magically appear. From what I'm reading here it sounds like Chase usually posts same day or next morning, so I'm trying to stay optimistic. The waiting is the worst part though, especially when you need the money for bills. Fingers crossed we both see it by tomorrow morning!
next year im def paying the fees upfront. This refund transfer stuff is for the birds ๐คฎ
Been there! When TurboTax shows "Payment Completed" for the refund transfer, it just means they successfully grabbed their $133 from your refund - not that your money is coming tomorrow. The IRS still has to finish processing everything on their end. Since you filed Jan 18th, you're actually right on track timing-wise. Most people are seeing about 3-4 weeks total processing time this year. Check WMR (Where's My Refund) on the IRS site - that'll give you the real status of when your remaining refund hits your account. The waiting sucks but you should see movement soon! ๐ค
One thing to watch out for when recording business miles - you can ONLY deduct miles driven while actively working (with an active delivery or driving to pick up an order). You can't deduct miles driving from your home to your first pickup or returning home after your last delivery. Those are considered "commuting" miles. Also, make sure you're tracking ALL your business expenses, not just mileage. Phone bills (% used for work), hot bags, car phone mounts, etc. can all be deducted on Schedule C along with your mileage.
This is such great information! I wish I had known about this years ago. I've been doing Instacart and DoorDash for about 18 months and have been religiously taking the standard deduction but completely ignoring my business expenses. One question though - what's the best way to track mileage going forward? I know some people use apps like MileIQ, but I'm wondering if there are simpler methods that are still IRS-compliant. Also, do you need to track every single trip or can you do periodic sampling and extrapolate? I'm definitely going to look into filing amended returns for last year. Even if I only drove 10,000 business miles, that's still potentially $6,000+ in deductions I missed out on. Thanks everyone for sharing your experiences!
For tracking mileage going forward, you definitely need to be consistent and detailed to stay IRS-compliant. The good news is you don't need anything fancy - even a simple notebook or phone app where you record date, starting/ending odometer readings, and business purpose will work. MileIQ is popular but there are free alternatives like Everlance or even just using Google Sheets. The key is tracking EVERY business trip - the IRS doesn't accept sampling or extrapolation for mileage deductions. Each trip needs to be logged separately. Make sure to record the date, starting location, ending location, odometer readings, and business purpose (like "DoorDash delivery to 123 Main St"). If you use the apps that automatically track based on GPS, just double-check they're only counting actual business miles and not personal driving. With 10,000 business miles at the current rate, you're looking at a significant deduction! Definitely worth getting those amended returns filed. Just make sure you have some way to reconstruct or estimate your past mileage reasonably - delivery app earnings statements can sometimes help with this.
Michael Green
Ok maybe I'm crazy but try checking your transcript REALLY early in the morning like 3-4am EST. For some reason I could never see updates during regular hours but middle of the night I could see everything. IRS systems are weird.
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Mateo Silva
โขcan confirm this actually works! system updates overnight on thursdays/fridays
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Misterclamation Skyblue
I'm going through the exact same thing! Filed March 8th, verified identity March 14th, and it's been radio silence ever since. My transcript is completely blank and WMR just says "still being processed" with no progress bars. Called twice and both reps told me the same thing - verification shows complete but to just wait longer. It's so frustrating not knowing if something is actually wrong or if this is just normal now. Really hoping we see some movement soon because I'm starting to stress that my return got lost somewhere in their system.
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