Does anyone know if you need a SEIN (State Employer Identification Number) in California just to issue 1099s? I'm in the same boat - freelancer in California occasionally hiring other freelancers, but I don't have any employees. Getting conflicting info about whether I need to register with EDD just to issue a few 1099s.

As someone who went through this exact situation last year as a California-based event planner hiring contractors across multiple states, I can share what I learned! The key thing to understand is that as an individual freelancer (not a business entity), your reporting obligations are much simpler than what corporations deal with. You're only required to report to California since that's where you're based and file your taxes. For boxes 5-7 on the 1099-NEC: - Box 5: Enter "CA" (your state) - Box 6: Leave blank if you don't have a California state employer ID (which you don't need as a freelancer with only independent contractors) - Box 7: Enter the full payment amount The contractors you hired are responsible for reporting their income to their respective home states (AZ, NY, CO). You don't need to file 1099s in those states unless you have a business registration or physical presence there, which it sounds like you don't. One important tip: Make sure you have W-9 forms from all your contractors before filing. This ensures you have the correct tax ID numbers and addresses, which prevents TIN mismatch penalties from the IRS. Track1099 should handle the electronic filing process smoothly once you have the boxes filled out correctly. You're doing great by getting this sorted out - many freelancers miss this requirement entirely!

Just a practical tip from someone who had to deal with this exact situation - if you end up having to fill out the W-8BEN-E as an individual (which is not ideal but sometimes unavoidable with PayPal), here's what worked for me: Part I: Fill out your personal information, using your name as the "organization" name Line 3: Check box for "Individual" Part III: Only complete if your country has a tax treaty with the US Parts IV-XXVIII: Leave completely blank Part XXX: Sign and date as an individual PayPal accepted this even though it's technically the wrong form. Their system is notoriously inflexible about these things.

I went through this exact same PayPal nightmare about 6 months ago! What finally worked for me was a combination of the approaches mentioned here. First, I tried the Claimyr service to get through to an actual PayPal representative - it took about 40 minutes but I finally reached someone who understood the issue. The rep explained that their system automatically flags certain accounts for W-8BEN-E based on transaction patterns, even for individuals. She walked me through two options: either convert my account type (which would take 5-7 business days and require re-verification) or complete the W-8BEN-E using the individual approach that Amelia outlined. I chose the second option since I needed my account restored quickly. Following her guidance, I filled out the form exactly as suggested - used my personal name as the organization, checked "Individual" on line 3, and left most sections blank. The key thing she emphasized was being consistent with how I originally set up my account. Form was accepted within 24 hours and my account was fully restored. Sometimes you just have to work within PayPal's flawed system rather than fight it!

This has been such an informative discussion! I'm a tax preparer and wanted to add a few practical tips for anyone making the QJV switch. First, timing-wise, if you're switching mid-year, pick a clear date (like the first of a month) and document it well. This makes the math much cleaner when you're splitting income and expenses between your individual Schedule Cs. Second, regarding the employee children - this is actually one of the nice benefits of a QJV. Both parents can claim the wages paid to your sons as business deductions on their respective Schedule Cs, and the kids still get all the same employment protections and benefits they had before. One thing to watch out for: make sure you're both genuinely involved in business decisions and operations. The IRS wants to see that this isn't just a paper arrangement to split income. Keep records of meetings you have together, emails about business decisions, and document how you divide responsibilities. Also, don't forget that both spouses will now need to make quarterly estimated tax payments if you're not having enough withheld elsewhere. The self-employment tax piece that someone mentioned earlier is real - both of you will pay SE tax on your respective shares, but you'll also both be earning Social Security credits.

As someone who recently made the switch to a QJV with my spouse, I wanted to share a few things I wish I'd known beforehand that might help others considering this change. One practical tip: when you're dividing up business responsibilities to show genuine material participation, consider having each spouse "own" specific aspects of the business operations. For example, I handle all client communications and sales while my husband manages inventory and vendor relationships. We both participate in major business decisions, but having clearly defined roles makes it much easier to document our respective contributions. Another thing that caught us off guard initially - you'll want to update your business insurance policies to reflect both spouses as business owners. Our liability insurance needed to be amended to cover both of us, and we had to provide documentation of the ownership change. Regarding the 50/50 split question that came up earlier - it doesn't have to be exactly equal, but whatever split you choose needs to reasonably reflect each person's contribution to the business. We started with 50/50 since we both put in similar hours, but I know other couples who do 60/40 or even 70/30 based on their actual involvement levels. The transition has been really positive for us overall. Having both spouses build Social Security credits and being able to each contribute to our own SEP-IRAs has been a nice bonus we hadn't initially considered.

Just wanted to add one more thing that might be helpful - when you do get your 1099-R form next year, make sure to keep all the documentation from your surrender (the policy statements, surrender paperwork, etc.) with your tax records. The IRS occasionally questions life insurance surrenders, especially larger amounts like yours, and having all the supporting documentation readily available can save you a lot of headaches if they ever ask for verification of the cost basis or how you calculated the taxable portion. Also, since this involves a policy that was set up by a family member decades ago, consider keeping copies of any documentation you find about premium payments or ownership transfers. This kind of paperwork can be really hard to reconstruct years later if the insurance company's records are incomplete or if there are ever questions about the transaction. Given all the great advice in this thread about verifying the cost basis, it sounds like you're on the right track to make sure everything is calculated correctly!

I went through something very similar last year when I surrendered a whole life policy my parents had set up for me. One thing that really helped was creating a simple spreadsheet to track all the different components and tax calculations. Here's what I'd suggest based on your situation: 1. **Get a detailed cost basis breakdown** - Don't just accept that $9,000 figure. Request a year-by-year summary from the insurance company showing premiums paid vs. policy charges. I found mine was actually $1,800 higher than initially stated. 2. **Calculate conservatively** - If your taxable gain is around $18,600 at 24% federal + 5.75% state, you're looking at roughly $5,530 total tax liability. With only $2,888 withheld ($2,088 federal + $800 state), you might want to make an estimated payment for the difference. 3. **Consider quarterly timing** - Since we're in Q4, you could make the estimated payment by January 15th to cover Q4 2025, which might be easier than trying to adjust W-4 withholdings now. The key is getting that cost basis verified first - it could significantly change your tax liability. I'd also recommend keeping detailed records of everything since insurance surrenders sometimes get IRS attention, especially with larger amounts like yours. Happy to share more specifics about my experience if it would help!

Has anyone used any specific tax software that handles C corp asset sales well? I'm trying to model different scenarios and my usual tax program isn't cutting it for something this complex.

Just went through a similar C corp asset sale situation last year and can confirm what others have said - QSBS treatment under Section 1202 doesn't apply to asset sales, only stock sales. The key distinction is that in an asset sale, the corporation is the one recognizing the gain, not the shareholders selling stock. One thing I wish I had known earlier is that there are some timing strategies you can still use to minimize the double tax hit. For example, you might be able to accelerate certain deductions in the year of sale, or if you have NOLs or other tax attributes, make sure you're maximizing their use before the sale closes. Also, depending on your purchase agreement terms, there might be some flexibility in how the purchase price is allocated among different assets - some might qualify for more favorable tax treatment than others. Worth having a detailed conversation with a tax professional who specializes in M&A transactions, not just general corporate tax work. The $17.5 million sale price suggests this is substantial enough that even small percentage improvements in tax efficiency could save significant dollars. Don't give up on optimization just because QSBS is off the table!