I'm dealing with a similar situation right now and wanted to share what I've learned from my research. One thing that hasn't been mentioned yet is the potential impact on your quarterly estimated tax payments. If you hold the equity personally and file an 83b election, you'll need to pay taxes on the fair market value immediately (even if it's minimal for an early-stage startup). But if your LLC holds it, the tax treatment flows through your S-Corp election, which could affect your reasonable salary requirements and payroll taxes. Also, consider this: if the startup ever issues additional equity rounds or has anti-dilution provisions, having the equity in your LLC might complicate those calculations. I've seen cases where LLCs holding equity had to provide additional documentation or legal opinions that individual shareholders didn't need. Given your 48-hour deadline, I'd lean toward personal ownership for simplicity unless your accountant specifically structured your LLC to hold investments. The QSBS exclusion potential alone (up to $10M tax-free if you hold for 5+ years) makes personal ownership attractive for startup equity.

Great question and timing is definitely tough! I've been through this exact scenario with two different startups as a consultant. From my experience, I'd strongly recommend taking the equity personally rather than through your LLC. Here's why: **Tax advantages**: The QSBS (Section 1202) exclusion that others mentioned is huge - potentially $10M+ in tax-free gains if you hold the shares for 5+ years. Your LLC can't take advantage of this. **Simplicity at exit**: When the startup eventually has a liquidity event, you'll thank yourself for not having to unwind LLC ownership structures or deal with potential phantom income issues. **83(b) election**: Much cleaner to file personally. The IRS forms are straightforward and you avoid any complications around your S-Corp election. **Future flexibility**: If you ever want to dissolve your LLC, transfer the equity, or include it in estate planning, personal ownership gives you way more options. The only real advantage of LLC ownership would be liability protection, but for equity compensation from a consulting client, that protection isn't typically necessary. Given your 48-hour deadline, personal ownership is the safer, simpler choice. You can always restructure later if needed, but it's much harder to go the other direction. Good luck with the decision!

I ignored a CP24 notice once thinking it was no big deal. BIG mistake. The penalties and interest kept growing, and eventually they sent a CP504 threatening to levy my bank accounts. Had to set up a payment plan and ended up paying way more than the original amount. Whatever you do, don't just throw the letter in a drawer and forget about it!

I went through this exact same situation about 6 months ago with a CP24 notice for around $750. The anxiety was real! Here's what I learned that might help: First, take a deep breath - these notices are super common and usually straightforward to resolve. The key is acting quickly rather than letting it sit. What worked for me was gathering ALL my tax documents (W-2s, 1099s, bank statements, etc.) and doing a line-by-line comparison with what the IRS claimed I didn't report. In my case, they were right - I had completely forgotten about a small 1099-MISC from some freelance work I did early in the year. If you determine the IRS is correct (like I did), paying online through IRS Direct Pay is the fastest way to stop interest from accumulating. The process was actually pretty simple once I stopped panicking about it. But if you think there's an error, definitely dispute it. The notice should have instructions on how to respond. Just make sure you do it within the timeframe they specify (usually 30 days from the notice date). Either way, don't let this snowball like some people do. Address it now while it's still manageable. You've got this!

Has anyone here dealt with the QBI (Qualified Business Income) deduction for delivery driving? I think OP was right to put zero since they're not doing deliveries anymore, but last year I qualified for a 20% QBI deduction on my net profit from deliveries which was sweet. It's one of the few perks of being a 1099 contractor instead of an employee.

For what it's worth, I think you handled everything correctly! Putting zero for QBI makes perfect sense since you're no longer in the delivery business - that deduction only applies to active business income. And removing the vehicle as an asset is the right move since you sold it. The key thing that might give you peace of mind is making sure your business use percentage was accurate when you claimed the loss last year. If you estimated something like 70-80% business use, try to back that up with your delivery app data if you still have it. The apps usually track your active delivery miles, but don't forget you can also count miles driving to busy delivery areas, between restaurants, etc. Since you got a nice refund bump from the vehicle loss, just keep any documentation you have (purchase/sale receipts, delivery app summaries, mileage logs if you kept them) in case the IRS has questions down the road. But honestly, vehicle losses from delivery work are pretty common and straightforward as long as the business use percentage is reasonable and supported.

The excessive withholding you're experiencing is unfortunately very common with multiple jobs, and you're right to question it! When you check Step 2 Option C, both employers calculate withholding as if that job alone puts you in a higher tax bracket, which creates significant overwithholding. Here's a practical approach that has worked well for many people: Keep Option C checked on your higher-paying job ($60k), but on your lower-paying job ($25k), switch to leaving Step 2 blank or use the Multiple Jobs Worksheet instead. This prevents the "stacking" effect where both jobs assume the worst-case scenario for your tax bracket. Also, don't forget that you can adjust your withholding mid-year! If you're consistently seeing $400+ in federal withholding on a $2,350 paycheck, you're likely on track for a massive refund. While that might feel good in April, you're essentially giving the government an interest-free loan of your money all year long. I'd recommend running your numbers through the IRS Tax Withholding Estimator with both paystubs handy - it'll give you a much more accurate picture of what you should actually be withholding based on your combined income and help you avoid that rent-sized chunk disappearing from every paycheck.

Based on everyone's advice here, I just wanted to share what ended up working for me in a similar situation. I was also getting hit with massive withholding across two jobs ($65k and $20k), and after reading through all these suggestions, I tried the approach of keeping the multiple jobs box checked only on my higher-paying job and leaving it blank on the lower-paying one. The difference was immediate and significant! My next paycheck had about $160 less in federal withholding, which feels much more reasonable. I also ran the IRS Tax Withholding Estimator like several people suggested, and it confirmed I was on track for about a $2,200 overpayment with my original setup. One thing I learned that might help others: the estimator actually walks you through different scenarios, so you can see how various W-4 adjustments will affect your withholding throughout the year. It's way less intimidating than I thought it would be, and having that concrete feedback gave me confidence to make the changes. For anyone still struggling with this, definitely don't just accept excessive withholding as "normal" for multiple jobs. There are absolutely ways to get it more balanced while still ensuring you don't owe at tax time.

This is such a fascinating topic! As someone who's always wondered about the "what if" scenario, I appreciate everyone breaking down the tax implications so clearly. One thing I'm curious about that hasn't been mentioned yet - what happens if you win but live in one state and buy the ticket in another state? Like if I'm a Florida resident (no state income tax) but buy a winning Powerball ticket while visiting New York - which state's tax rules apply? Also, I've heard that some lottery winners actually choose the annuity payments over the lump sum specifically for tax reasons. Does spreading the payments out over 20-30 years help keep you in lower tax brackets each year, or do you still end up paying roughly the same percentage overall? The professional advice recommendation makes total sense for billion-dollar wins, but I'm wondering at what dollar amount it becomes worth hiring specialized help versus just using a good CPA?

This is such a great discussion! One aspect that hasn't been covered much is the quarterly estimated tax payments you'll need to make after a big lottery win. Since the initial 24% withholding usually isn't enough to cover your full tax liability on a massive jackpot, you'll likely need to make estimated payments throughout the year to avoid underpayment penalties. The IRS expects you to pay as you go, so even though you got the money in one lump sum, you might need to send them additional payments every quarter until you file your return. With a billion-dollar win, those quarterly payments could be tens of millions each! Also, something to keep in mind - if you're married, this could actually bump your spouse into gift tax territory if you're not careful about how you handle joint accounts and spending. The IRS considers lottery winnings as belonging to whoever signed the ticket, so transfers to your spouse might trigger gift tax rules if not structured properly. It's wild to think about, but these are the kinds of "good problems" that come with hitting it big!