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I made the switch from LLC to S-corp for my electrical contracting business last year. Here's what I learned: - The tax savings are real. I saved about $7k in self-employment taxes by taking part of my income as distributions instead of all as salary. - BUT the paperwork and compliance requirements increased significantly. You need to run actual payroll, do quarterly filings, have more detailed bookkeeping, etc. - You absolutely need a good accountant for an S-corp. I tried doing it myself at first and made some mistakes that could have been costly. - The sweet spot where S-corp makes sense is when you're consistently making $40-50k+ in profit. For receipt tracking, I've been using Expensify and it's been great for construction work. Their SmartScan feature is really accurate with contractor supply stores like Home Depot and Lowe's receipts.
Thanks for sharing your experience! Do you think it makes sense to form an S-corp right away when switching from single-member LLC to having employees? Or should I stay as an LLC taxed as a partnership first until I hit that $40-50k profit consistently?
I'd recommend staying as an LLC taxed as a partnership first until you're consistently hitting that profit threshold. You can always convert to an S-corp later, and it's much easier than going the other direction. The LLC with employees will still give you the liability protection you need, but with less administrative overhead. One thing I forgot to mention - with an S-corp, you must pay yourself a "reasonable salary" before taking distributions. The IRS watches this closely. For construction contractors, that's typically 60-70% of your profit as salary at minimum. So if your profits are tight or inconsistent, the S-corp advantages diminish since most of your income will need to be salary anyway.
One thing nobody's mentioned yet - PLEASE make sure you're charging enough for your work! I'm a contractor too and had the same problem for years. I'd underbid jobs trying to be competitive, then end up barely breaking even after expenses. Two things that helped me: 1. Track EVERYTHING for a few jobs - your time (including estimating, driving, cleanup), materials, equipment wear, fuel, etc. Most contractors don't realize how much all the little things add up. 2. Add at least 20% to whatever you think a job should cost. I was amazed that customers still hired me after raising prices - turns out quality work is worth paying for. You can't fix your tax situation if your business isn't profitable enough in the first place!
Something else to consider - when you transfer your crypto to Robinhood, that's not a taxable event (it's just moving your property). But the moment you sell on Robinhood, that's when the taxable event occurs. Also, Robinhood's tax forms will show the proceeds from your sale but won't have your cost basis information for crypto transferred in. They'll likely issue a 1099-B with your proceeds, but the cost basis section might be blank or listed as "unknown," which puts the responsibility on you to report the correct cost basis on your tax return. If you significantly underreport your cost basis, that's where audit flags might come up since the IRS will see a mismatch between your reported gain and what they'd calculate based on zero cost basis.
Thanks, this is super helpful. So if I understand correctly - transferring to Robinhood isn't taxable, but I need to make sure I have documentation ready for my cost basis when I do sell, since Robinhood won't have that info? Would it make more sense to sell on my current exchanges where at least some transaction history exists, rather than moving to Robinhood first?
That's exactly right - transferring isn't taxable, but you need to document your cost basis for when you do sell, since Robinhood won't have that information. As for whether to sell on current exchanges versus transferring to Robinhood first, that's a great question. There's a potential advantage to selling on exchanges where you have some transaction history, as you could potentially have more documentation to support your reported cost basis. However, if those are foreign exchanges, they might not issue U.S. tax forms, which could create other complications. If your current exchanges can provide transaction history reports that show your purchases, that documentation could be valuable regardless of where you ultimately sell. The key is having a defensible way to calculate and document your gains.
Don't overlook the fact that if you've been trading crypto while a permanent resident but before becoming a citizen, you still have US tax liability on those gains. The US taxes residents on worldwide income. Also, be aware that transferring between cryptocurrencies (like trading Bitcoin for Ethereum) counts as a taxable event too - each swap is technically a sale of one asset and purchase of another. This catches a lot of people by surprise.
Is that true even for transactions that happened before they became a permanent resident? I thought you only had to worry about US taxes once you actually became a resident.
Don't forget about state taxes too! Depending on which state you live in, you might need to report that Belgian rental income on your state return as well. Some states have different rules for foreign income than federal. I learned this the hard way with my rental property in Mexico. I reported everything correctly on my federal return but didn't realize California wanted their cut too. Got a nasty surprise assessment letter the following year.
Oh no, I hadn't even thought about state taxes! We're in New York - do you know if they follow the federal rules for foreign income or have their own system? This is getting more complicated by the minute.
New York generally follows federal rules for income inclusion, so if you're reporting the rental income on your federal Schedule E, you'll need to include it on your NY return too. The one benefit is that NY does allow credits for foreign taxes paid, similar to the federal system. Some states like Nevada or Florida might be more advantageous for people with significant foreign income since they don't have state income tax. But for now, plan on reporting that Belgian rental income on both federal and NY returns.
Has anyone mentioned Form 8833? If you're planning to take a position based on the US-Belgium tax treaty, you might need to file this form to disclose your treaty-based position. I had to do this with my rental properties in France.
Don't forget that as a self-employed person, you should also be making quarterly estimated tax payments throughout the year! This is something I learned the hard way my first year of freelancing. The IRS expects you to pay as you earn, and if you wait until tax filing time, you might get hit with underpayment penalties on top of what you owe. For 2025, the quarterly payment due dates are April 15, June 15, September 15, and January 15 (2026). Set calendar reminders! Even if you're abroad, these deadlines still apply to US citizens.
Wait really? I had no idea about quarterly payments! So even though I'm filing for 2024 now, I'm supposed to already be making payments for 2025? How do I even calculate how much to send if I don't know exactly what I'll make this year?
That's right! For 2025 income, you need to make four payments throughout the year. You have a couple of options for calculating how much to pay. The simplest is to take your total expected tax for the year and divide by 4. You can base this on what you expect to earn this year. Alternatively, you can use the "safe harbor" provision - if you pay either 90% of this year's tax or 100% of last year's tax (whichever is smaller) through withholding and estimated payments, you won't face penalties. So once you file your 2024 taxes, you could use that amount as your guide for 2025 payments. The IRS Form 1040-ES has worksheets to help calculate this. It seems complicated at first, but it gets easier after your first year!
I'm also a content creator and I found that using a tax software specifically designed for freelancers/self-employed people was super helpful. I tried FreeTaxUSA last year and it walked me through all the self-employment stuff pretty clearly. TurboTax Self-Employed is good too but more expensive. Don't try to do this by hand your first time - the software asks you questions in plain English and fills in the right forms.
Seconding FreeTaxUSA! The self-employment section is really straightforward. Plus it's way cheaper than TurboTax. They have good explanations about what counts as a business expense too. I was able to deduct part of my phone bill, internet, computer, camera equipment, editing software, and even some travel costs related to content I was making.
Zainab Ismail
Just a heads up - even if your S-Corp return was filed, you need to keep a copy of that return for your records. Try sending a certified letter to your accountant requesting a complete copy of the filed return. This creates a paper trail showing you've made a reasonable effort to obtain your records. If that doesn't work, you can request a copy of the filed return directly from the IRS using Form 4506. It costs about $43 but might be worth it for your records and peace of mind.
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NebulaNinja
ā¢That's really good advice, thank you! Do you know how long Form 4506 typically takes to process? I'm concerned about having proper documentation before next year's filing.
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Zainab Ismail
ā¢Form 4506 usually takes about 75 days to process, so it's definitely not a quick solution. That's why I'd recommend trying the certified letter to your accountant first since that would be much faster. For next year's filing, you should be fine even without a full copy of this year's return as long as you have your K-1. However, if you plan to switch accountants, having the complete return will help the new preparer understand your business situation better.
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Connor O'Neill
Something nobody mentioned yet - make sure you check if your state requires a separate S-Corp filing! Some states require a separate state S-Corp return in addition to the federal one. If your accountant didn't file that too, you might have a state filing issue to deal with.
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Yara Nassar
ā¢This is super important! My accountant filed my federal S-Corp return but completely forgot about my state filing. Ended up with a $400 penalty that took months to sort out.
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