Pro tip: if you want less tax withheld from your bonus, increase your 401k contribution just for that paycheck if your company allows it. I put 50% of my bonus straight into 401k last year and it lowered my taxable income. Double win!

This is actually a really important point! My bonus pushed me into a higher tax bracket last year because it came in December. If it had come in January, my tax situation would have been completely different. Timing matters!

Is Publication 901 updated for 2024 yet? I checked a few weeks ago and they still had the 2023 version online. Also, do you know if non-residents can claim education credits like the American Opportunity Credit? I took some classes last year.

You're right that the official IRS website still has the 2023 version, but they don't typically update Publication 901 every year - only when treaty provisions change significantly. The 2023 version should still be applicable for most countries for your 2024 taxes. For education credits, non-resident aliens generally cannot claim the American Opportunity Credit. However, if you're from certain countries with specific education provisions in their tax treaties (like China, India, or several European countries), you might qualify for different education-related benefits. You'll need to check the specific article in your country's treaty that addresses students or education expenses.

Yes, you can e-file a 1040NR but not with every software. I used OLT.com (OnLine Taxes) last year and was able to e-file my non-resident return. Sprintax also supports e-filing for 1040NR. Most free options don't support it though.

What exactly is the carried interest loophole? I hear about it but don't really understand how it works or why it's such a big deal.

Carried interest is basically the share of profits that hedge fund and private equity managers get as compensation for managing investments. Instead of being taxed as ordinary income (which can be up to 37%), it's taxed at the capital gains rate (usually 20%). So imagine a fund manager who makes $10 million from managing other people's money. Instead of paying $3.7 million in taxes like other high-earning professionals would, they might only pay $2 million. That's a $1.7 million tax break just because of how their compensation is classified! Meanwhile teachers, doctors, and engineers all pay the higher ordinary income rates on their earnings.

That would totally screw over people in high cost of living areas though. $500k won't even buy you a 1 bedroom condo in San Francisco or NYC. Not everyone with a mortgage over $500k is wealthy - many are middle class families in expensive metro areas.

Do they really count retirement accounts? I thought those were protected. I have about $45k in my 401k but didn't think that would count against me for an OIC calculation.

Yes, they absolutely consider retirement accounts in your OIC calculation. While you're right that they can't directly seize most retirement accounts, they still view them as assets that could be used to pay your tax debt. The IRS typically includes a percentage of retirement account values in your "reasonable collection potential" calculation. They don't necessarily expect you to cash them out (especially given the penalties), but they do factor them into what they think you could potentially pay. This is one of the most common misunderstandings that leads to OIC rejections.

They apply any payments you've made toward your tax debt, they don't just keep the money. So if your offer gets rejected, that 20% payment (or whatever payments you've made) will reduce your overall tax debt. It's not lost money.

Thanks for suggesting FreshBooks! How does it handle retroactive data? I'd need to import all my transactions from January 2024 onward. Also, does it generate proper tax forms or just the basic reports?

Retroactive data import works great in FreshBooks. You can import past transactions either directly from Stripe (going back as far as you need) or via CSV if you have the data exported already. I've done this multiple times when switching between systems. For tax forms, it doesn't generate the actual forms like 1099-K, but it creates all the reports you need to fill those forms accurately. There's a specific "Tax Summary" report that breaks everything down by category for tax filing purposes. It also integrates with most tax filing software, so you can export your data directly if needed. Most small business owners still need an accountant or tax software for the final filing, but FreshBooks gives you all the organized data you need.

That price is way out of range for many small startups though. $249/month is $3000/year which is hard to justify when you're just starting out. Do they have any lower tiers for businesses with fewer transactions?