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I'm curious if anyone has actually done this successfully? My CPA keeps giving me wishy-washy answers about my S-corp investing in stocks saying "it depends" and "it's a gray area"...
I did this for about 2 years with my marketing S-corp. We had excess cash and invested about 15% of our revenue in a mix of stocks and bonds. Ended up unwinding it because: 1) The compliance headache wasn't worth it 2) When we had a big capital gain it messed up our qualified business income deduction calculations 3) Our tax savings were minimal compared to just taking distributions and investing personally
Thanks for sharing your real experience! That's helpful to know it wasn't worth the hassle. I've been driving myself crazy trying to figure out if there's some magic tax advantage I'm missing, but sounds like there really isn't for most small S-corps. Going to stick with reasonable salary + distributions and keep my investments personal.
I've been wrestling with this exact question for my own S-corp (consulting business), and after lots of research and conversations with tax professionals, I've concluded that the potential tax benefits rarely justify the risks and complications. The key issue that hasn't been fully addressed here is timing differences. While unrealized gains aren't taxed immediately, when your S-corp does sell investments, those gains flow through to your personal return in the year of sale - which could push you into higher tax brackets unexpectedly. This makes tax planning much more difficult compared to controlling when you realize gains on personal investments. Also consider the opportunity cost of having investment capital tied up in your business entity. If you ever want to wind down the S-corp or change business structures, extracting those investment assets could trigger significant tax events. My recommendation: stick with the traditional approach of reasonable salary + distributions for personal investments. The tax efficiency difference is minimal, but the simplicity and flexibility advantages are substantial. Your future self will thank you for keeping things clean and straightforward.
Just FYI - the per diem method is great, but you should still keep a detailed travel log showing: - Dates of departure and return for each trip - Each place you traveled to (city, state) - The business purpose for your travel - Who you met with (if applicable) IRS Publication 463 covers all this. You don't need meal receipts when using per diem, but you absolutely need documentation proving you were actually traveling for business on those dates.
Does a calendar with my client meetings and locations work as sufficient documentation? I keep everything in Google Calendar with the client name, meeting purpose, and location.
A detailed calendar with client meetings and locations is a good start, but I would recommend enhancing it slightly. The IRS wants to see a clear connection between your travel and business purpose. Make sure your calendar entries include the business purpose of each meeting (like "Client consultation for XYZ project" rather than just "Meeting with ABC Company"). Also, keep some form of evidence that the meeting actually occurred - this could be email correspondence, meeting notes, or even receipts for associated business expenses in that location. Having multiple forms of documentation creates a stronger case if you're ever questioned about the business nature of your travel.
Been self-employed for 10+ years and use per diem for meals exclusively. Quick tip: don't forget the first and last day of travel are calculated at 75% of the standard rate. A lot of people miss that and claim 100% for all days.
Wait really?! I've been claiming 100% for all days including first and last day. Should I file an amended return??
@Dylan Campbell - Yes, the 75% rule for first and last day of travel is correct according to IRS regulations. Whether you need to amend depends on how much extra you claimed and how many travel days you had. If it s'a significant amount, you might want to file an amended return Form (1040X to) avoid potential issues later. For future reference, the IRS considers that you re'only away for a partial day on departure and return days, hence the 75% rate. Most tax software should handle this automatically if you enter your travel dates correctly.
Anybody know if this question on the 1040 about digital assets is new? I swear I don't remember seeing this on my tax forms before last year. Is the IRS just trying to crack down on crypto now?
It's been around for a few years but they keep changing the wording. It used to be called "virtual currency" instead of "digital assets" and was on Schedule 1. Now they've moved it to the main 1040 form and broadened the language to include more types of digital assets, not just cryptocurrency. Definitely part of the IRS trying to increase compliance with crypto reporting.
I had the exact same confusion with my Robinhood crypto trades! After going through this myself, I can confirm that yes, you absolutely need to answer "Yes" to that digital asset question. The IRS doesn't care which platform you used - crypto is crypto. One tip that really helped me: make sure you download your full transaction history from Robinhood, not just rely on the 1099-B. I found some small transactions that weren't clearly reflected on the form but still needed to be reported. Also, if you did any transfers between different cryptocurrencies (like Bitcoin to Ethereum), those count as taxable events too, even if you didn't convert back to cash. The "basis not reported to IRS" thing is annoying but manageable if you keep good records. I just went through my transaction history month by month and matched up my purchases with sales. Takes some time but beats getting a letter from the IRS later!
Similar situation happened to me! If you use tax software, there's usually a "withholding calculator" feature that can help you figure out what to change on your W-4. I realized that when I got my promotion mid-year, the payroll system calculated my withholding as if I had been making that amount all year, which resulted in under-withholding. I had to manually increase my withholding to account for the actual annual income.
Which tax software has the best withholding calculator? I use TurboTax but never noticed this feature.
I've found H&R Block's withholding calculator to be the most user-friendly, but TurboTax does have one too! In TurboTax, after you file, look for the "Tax Tools" section and you should see a "W-4 Withholding Calculator" option. It uses your actual tax return data to make recommendations for the current year. The IRS also has a free withholding estimator on their website that's pretty comprehensive, though not quite as user-friendly. The advantage of the IRS one is that it's always up to date with the latest tax law changes.
This is a really common situation when you get a significant raise or promotion mid-year! Your payroll system basically treats each paycheck as if you'll earn that same amount for the entire year, which works fine when your income is steady but creates problems when it changes. Here's what likely happened: When you were making $70K, your withholding was calculated correctly for that income level. But when you got promoted and started earning more, the system didn't "catch up" to account for the fact that your total annual income would now put you in a higher tax bracket. The $1,350 in interest income definitely contributes too - that's roughly $324 in taxes at the 24% bracket with no withholding. For next year, I'd recommend using the IRS Tax Withholding Estimator (it's free on their website) or updating your W-4 to withhold an additional amount each paycheck. You can calculate roughly how much extra by dividing what you owed ($1,300) by the number of remaining pay periods in the year. The good news is this is totally fixable going forward - you just need to be proactive about adjusting your withholding when your income changes significantly!
Sean Fitzgerald
Hey, are you using TurboTax by any chance? I ran into that EXACT SAME ISSUE last week. The solution was to go to Forms Mode (you can search for it in the search bar at the top), then find Form 2210, and there's a checkbox that says "I didn't file this form last year" - check that and the software will stop asking for the missing info! Also, just a heads up that when you switch from MFJ to MFS, some of your deductions will be different. Make sure both of you don't claim the same credits for the kids. And double check your student loan interest deduction - when filing MFS, you usually can't claim that deduction (though the payment benefits might still make MFS worth it).
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Zara Khan
ā¢Quick correction - the student loan interest deduction is completely unavailable to anyone filing MFS regardless of income. It's one of the tax benefits you automatically give up when choosing MFS status. Just wanted to clarify in case people are counting on that deduction!
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Khalid Howes
I had this exact same issue when I switched from MFJ to MFS three years ago! The tax software kept insisting I needed Form 2210 data from the previous year even though we'd never filed one. Here's what worked for me: First, double-check your 2022 return by searching the PDF for "2210" like others mentioned. If it's not there, you're good. Then in your tax software, look for an "interview mode" or "easy step" option and switch it OFF - go to the more detailed/advanced mode instead. This usually gives you more control over these yes/no questions. In the advanced mode, when it asks about Form 2210, there should be a clear "No, I did not file this form" option rather than just trying to skip past it. If you're still stuck, try starting a completely fresh return in the software and being very deliberate about answering "No" to the Form 2210 question the first time it appears. One more tip - make sure you're entering your 2022 AGI correctly from your actual tax return (not from memory). Sometimes the software gets confused if there's a mismatch and starts asking for forms you didn't file. Good luck finishing up before your extension deadline!
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