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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?
Anyone else notice that FreeTaxUSA sometimes doesn't import all transactions correctly? I had to manually check every single stock sale against my 1099-B because it missed about 10% of my trades when I tried the import function.
Great question! You're right to be cautious about doing things correctly. As others have mentioned, you definitely don't need to mail your 1099-B to the IRS - Fidelity already sent them a copy electronically. Just make sure when you're entering the data into FreeTaxUSA that you double-check all the numbers match exactly what's on your form. Pay special attention to the cost basis - if it shows "basis not reported to IRS" for any transactions, you'll need to make sure you have your own records of what you paid for those shares. With $3,200 in gains, you're well above the threshold where this needs to be reported, but it's not a huge amount that would typically trigger extra scrutiny. The key is just being accurate and consistent with what your broker reported. Good luck with the rest of your filing!
This is really helpful advice! I'm also a first-time stock trader and was worried about the same thing. Quick follow-up question - when you mention "basis not reported to IRS," does that typically happen with older stocks or is it more common with certain types of transactions? I want to make sure I'm not missing anything when I review my own 1099-B.
I just went through this exact same frustration with FreeTaxUSA last week! The promo code field is definitely easy to miss - it's on the summary page right before you proceed to payment, but it's in a pretty small font near the bottom of the fee breakdown section. One thing that helped me was clearing my browser cache and starting the checkout process over. Sometimes the promo code field doesn't load properly if you've been going back and forth between pages. Also make sure your promo code is still valid - I learned the hard way that some of them have pretty short expiration windows. If you're still within a few days of filing, definitely try contacting their customer support. I've heard mixed results but some people have gotten retroactive discounts applied. Worth a shot especially if it was a decent sized promo code!
Thanks for the tip about clearing browser cache! I hadn't thought of that but it makes sense that the page elements might not load properly after navigating back and forth. I'll definitely keep that in mind for next year's filing. Did you end up having success with customer support when you contacted them? I'm curious if they were able to apply your promo code retroactively or if you had to just accept the full price.
I ran into this exact same issue with FreeTaxUSA this year! After reading through all these responses, I want to add that the promo code field location can actually vary slightly depending on whether you're filing just federal or federal + state. When I was doing just federal (which is free anyway), I didn't see any promo code field at all. But when I added state filing, suddenly there was a small "Enter promotional code" link that appeared in the state filing fee section. It was really subtle - just looked like regular text, not even a proper button. The key thing I learned is to look for it specifically in the fee breakdown area where it itemizes your charges. Don't look for a big obvious promo code box like you'd see on retail sites. FreeTaxUSA's interface is pretty minimal and the promo field blends in with the rest of the text. Also make sure you hit "Apply" after entering the code - I almost forgot that step!
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.
Keith Davidson
dont forget to look into taking some tax specific continuing ed before interviewing! i made the audit to tax switch 2 years ago and the CCH courses helped me alot. also try the IRS VITA program if u can volunteer during tax season - its basic returns but gives u hands on experience u can talk about in interviews. also tax isnt all sunshine compared to audit lol. busy season is BRUTAL especially at smaller firms. but at least its concentrated in 1 part of the year instead of constant deadlines. clients r way more appreciative in tax vs audit where nobody wants u there!
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Victoria Stark
ā¢Thanks for the reality check about busy season! Is it really that much worse than audit busy seasons? I'm used to 60+ hour weeks during quarter and year-end closes, but it sounds like tax season might be even more intense. Do you find the work more satisfying despite the hours?
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Keith Davidson
ā¢Tax busy season is different - think 70+ hour weeks from February thru April 15, but then much more reasonable the rest of the year. Public audit feels like constant rolling deadlines that never end. Tax has a more defined "hell period" but then actual slow seasons where u can take vacation. The work is way more satisfying imo. In audit clients see you as the enemy, but in tax you're actually helping them save money and they appreciate it. Plus the work is more varied - every client has different issues instead of auditing the same accounts over and over. I'm much happier despite the crazy feb-april period.
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Monique Byrd
Your audit background actually puts you ahead of many people trying to break into tax! I made a similar transition 18 months ago from internal audit to tax preparation, and here's what worked for me: First, don't undersell yourself - you already understand financial statements, have analytical skills, and client experience. That's huge. I'd recommend getting the IRS Enrolled Agent certification if you have time - it shows commitment to tax and gives you credibility with employers. For the job search, focus on small to mid-sized CPA firms rather than big chains. They value the CPA credential more and are often willing to train someone with your background. I found success by networking through my state CPA society chapter - many tax professionals are happy to chat about their path and sometimes know of openings. Also consider reaching out to firms in October/November when they're staffing up for busy season. Many are willing to bring on experienced CPAs as "seasonal" staff with the potential for full-time offers after April 15th. The pay might be lower initially, but it's a foot in the door with real experience to put on your resume. The transition has been worth it for me - tax work feels more collaborative with clients rather than adversarial like audit. Good luck with the switch!
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Zoe Stavros
ā¢This is really helpful advice! I'm curious about the networking aspect - did you reach out to tax professionals cold through the CPA society or did you have existing connections? I'm a bit nervous about networking since I don't know anyone in tax currently, but it sounds like it was key to your success. Also, how long did it take you to get comfortable with tax concepts once you started? Coming from audit, I'm worried about the learning curve even though everyone says the fundamentals transfer over.
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