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I hope someone can clarify a side question about taxes - if my single-member LLC has a brokerage account and earns dividends or capital gains, do I need to make quarterly estimated tax payments? Or can I just settle up at tax time?
Yes, you should generally make quarterly estimated tax payments if you expect to owe $1,000 or more in taxes from your LLC income (including investment income from the brokerage account). Since a single-member LLC is a pass-through entity, all that investment income flows to your personal tax return. If those dividends and capital gains are substantial, you'll want to make quarterly payments to avoid an underpayment penalty. The safe harbor is generally paying either 90% of current year tax or 100% of prior year tax (110% if your AGI was over $150,000).
Just want to add my experience here - I had the exact same confusion when setting up my LLC brokerage account last year. The key thing that helped me understand was realizing that "owner EIN" vs "LLC EIN" is really about tax filing context, not about which number to use for account setup. For your brokerage account, you definitely want to use the LLC's EIN that you already obtained from the IRS. That's the correct identifier for your business entity. The confusion about "owner's EIN" typically comes up in tax discussions where the IRS is explaining that single-member LLCs report income on the owner's personal return rather than filing a separate business return. One tip: when you're filling out the brokerage application, make sure to select "LLC" as your entity type rather than "Individual" - this will help ensure they process everything correctly with your LLC EIN. I initially started filling it out as an individual account and ran into issues until I switched to the business account option. Also keep your EIN confirmation letter handy - most brokerages will ask for it during the verification process along with your Operating Agreement.
This is really helpful advice! I'm just getting started with my single-member LLC and haven't opened a brokerage account yet, but this thread has been incredibly informative. The distinction between entity selection and tax treatment makes so much more sense now. Quick question - when you mention selecting "LLC" as the entity type, did you have to provide any additional documentation beyond the EIN letter and Operating Agreement? I'm wondering if there are any other forms or certificates I should prepare in advance. Also, did your brokerage require you to have a separate business bank account before opening the investment account, or could you set up the brokerage account first?
Don't forget that if you absolutely can't get your W2, you can file Form 4852 (Substitute for W-2) with your tax return. You'll need to estimate your wages and tax withholding as accurately as possible using your last pay stub. Not ideal, but it's there as a last resort if you truly can't get your W2s any other way.
Just be careful with this approach. If your estimates are significantly off, you might have to file an amended return later when the correct information becomes available. The IRS might also delay processing your return if they see discrepancies.
Another option that worked for me was checking if your former employers used a payroll service like ADP or Paychex. Even after leaving on bad terms, you might still be able to access your employee portal if you remember your login credentials. Many people don't realize these accounts often stay active for a while after termination. I was able to download my W2 directly from ADP's website without having to contact my awful former boss at all. Just go to the payroll company's website and try logging in with your old credentials - worst case scenario it doesn't work, but if it does, you can get your W2 immediately.
My tax person said not to worry about blank wages its normal during processing just gotta wait it out
This happened to me last year! My wages were blank for almost a month while everything else updated. Turns out my employer had filed my W-2 late and the IRS was waiting for that info to populate. Once it finally showed up, my refund was approved within a few days. Don't panic - as long as your other info is updating it means they're actively processing your return!
Has anyone actually dealt with form 8965 recently? I thought this was phased out years ago when the individual mandate penalty went to zero. My tax software didn't even include this form when I filed my 2022 taxes.
Form 8965 was used for tax years 2014 through 2018 to claim exemptions from the individual health insurance mandate. After the Tax Cuts and Jobs Act reduced the federal penalty to $0 starting in 2019, the form became obsolete for federal taxes. However, as others have mentioned, states like California, Massachusetts, New Jersey, Rhode Island, and DC have their own individual mandates with penalties. If OP lives in one of these states, they might need to deal with state-specific health insurance reporting requirements, though the specific forms would be different from the federal Form 8965.
Thanks for explaining! That makes sense why my software didn't include it. Sounds like the IRS computer systems might be triggering an outdated notice or possibly this is for a state requirement. Either way, proving coverage should resolve it.
I had this exact same issue with my 2022 return! The IRS system automatically flagged my return because there was a mismatch between what they expected to see for health coverage reporting and what was actually filed. Here's what worked for me: First, gather all your health insurance documentation - insurance cards, EOB statements, premium payment records, anything that shows continuous coverage through 2022. Then write a clear letter explaining that you maintained qualifying health coverage through your employer for the entire tax year. The key is to be very specific in your response. Include your SSN, the notice number, and tax year at the top of your letter. State clearly: "I maintained qualifying health insurance coverage through my employer [Company Name] for the entire 2022 tax year and respectfully request removal of the individual shared responsibility penalty." Make copies of everything before you send it, and use certified mail to the address on the notice. I got my penalty reversed within about 6 weeks. The IRS computers sometimes miss the electronic reporting from employers or insurance companies, but once a human reviews your documentation, it gets sorted out pretty quickly. Don't stress too much - this is more common than you'd think, especially when employer reporting systems have glitches!
Nathan Kim
Quick tip that saved me last year: If you're setting up a SEP for the first time, remember that some brokerages take several days to process new account applications. Don't wait until April 14th to start the process! I use Vanguard and it took about 7 business days from application to being able to fund my account. Also, keep in mind that the 25% limit is really closer to 20% of your net profit due to the way the calculation works. There's a specific formula the IRS uses that reduces your maximum contribution.
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Ezra Collins
ā¢Thanks for the tip about account setup timing! I was thinking of using Fidelity - has anyone had experience with how long their SEP setup process takes? I definitely don't want to miss the deadline because of administrative delays.
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Nathan Kim
ā¢I haven't used Fidelity specifically for a SEP, but my buddy set one up with them last year and I believe it took about 3-4 business days to complete. Still, I'd recommend giving yourself at least two weeks before the deadline just to be safe. The other thing to consider is that even after the account is set up, transfers from your bank can take a few additional days to clear. Electronic transfers are typically faster than mailing a check, but even those can take 1-3 business days depending on your bank and the brokerage.
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Eleanor Foster
One thing nobody's mentioned - make sure you're calculating your contribution correctly if you have an LLC or S-Corp! The rules are different depending on how your business is structured. With my S-Corp, I pay myself a salary and the SEP contribution limit is based on my W-2 wages, not my total business profit.
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Lucas Turner
ā¢This is an important point. Are you saying if I'm an LLC taxed as an S-Corp and I pay myself $60,000 in salary but the business makes $120,000 in profit, my SEP contribution would be limited to 25% of the $60,000 salary, not the full $120,000?
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Kingston Bellamy
ā¢Exactly right! With an S-Corp election, your SEP contribution is limited to 25% of your W-2 wages, not the business profits. So in your example with $60,000 salary, your max SEP contribution would be around $15,000 (25% of $60k), even though the business made $120,000 total. This is why many S-Corp owners also consider Solo 401(k)s instead of SEPs - with a Solo 401(k), you can contribute as both employee and employer, potentially allowing for higher total contributions. The employee portion can be up to $22,500 (for 2023) plus 25% of your W-2 wages as the employer contribution. Make sure to discuss this with your accountant since the optimal salary vs. distribution split for S-Corps involves balancing self-employment tax savings against retirement contribution opportunities.
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