How do taxes work with donations made to an individual, e.g. for free software I wrote?
Do I report it as income? Is it subject to just the same amount of   taxes (~30%) as regular income? Are there any restrictions on how it   can be used? It is income. You can deduct the costs of maintaining the web page and producing the software from it (have an accountant do that for you, there are strict rules on how to do that, and you can only deduct up to the income if its a hobby and not a for-profit business), but otherwise it's earned income like any other self employment income. It is reported on your schedule C or on line 21 of your 1040 (miscellaneous income), and you're also liable for self-employment taxes on this income. There are no restrictions, it's your money. Technically, who is the donation even being made to? Me, just because   I own the webpage? Yes. This is for the United States, but is there any difference if the   donations come from overseas? No, unless you paid foreign taxes on the money (in which case you should fill form 1116 and ask for credit). If you create an official 501(c) organization to which the donations are given, instead of you getting it directly, the tax treatment will be different. But of course, you have to have a real charitable organization for that. To avoid confusion - I'm not a licensed tax professional and this is not a tax advice. If in doubt - talk to a EA/CPA licensed in your State.
This is tax fraud, plain and simple. I recently wrote an article The Step Transaction Doctrine, in which I explain that a series of events may each be legal, but aggregate to one transaction and the individual steps are ignored.  In this case, it goes beyond that, by accepting $5/mo you are already outside the tax code. As littleadv noted, you can't work for a legitimate business for free and not expect to have some kind of issue. The $14K/yr gift isn't a bona fide gift, but ties to that work. Whether you're self-employed or not, knowing exactly how much tax you will pay is not always an easy task.  Various actions you can take (e.g., charitable donations, IRA contributions, selling stocks) may increase or reduce your tax liability. One tool I've found useful for estimating federal taxes is the Excel 1040 spreadsheet.  This is a spreadsheet version of the income tax return form.  It is not official and is not created by the IRS, but is maintained as a labor of love by a private individual.  In practice, however, it is pretty much an accurate implementation of the tax calculation algorithms encoded in the tax forms and instructions. The nice thing about it is that it's a spreadsheet.  You can plug numbers into various slots in the spreadsheet and see how they affect your federal tax liability.  (You may also owe state taxes depending on what state you live in.)  Of course, the estimates you get by doing this are only (at most) as accurate as your estimates of the various numbers you plug in.  Still, I think it's a free and useful way to get a ballpark estimate of your tax liability based on numbers that you can more easily estimate (e.g., how much money you expect to earn). Yes, if you can split your income up over multiple years it will be to your advantage over earning it all in one year.  The reasons are as you mentioned, you get to apply multiple deductions/credits/exemptions to the same income. Rather than just 1 standard deduction, you get to deduct 2 standard deductions, you can double the max saved in an IRA, you benefit more from any non-refundable credits etc. This is partly due to the fact that when you are filing your taxes in Year 1, you can't include anything from Year 2 since it hasn't happened yet. It doesn't make sense for the Government to take into account actions that may or may not happen when calculating your tax bill. There are factors where other year profit/loss can affect your tax liability, however as far as I know these are limited to businesses. Look into Loss Carry Forwarded/Back if you want to know more. Regarding the '30% simple rate', I think you are confusing something that is simple to say with something that is simple to implement.  Are we going to go change the rules on people who expected their mortgage deduction to continue? There are few ways I can think of that are more sure to cause home prices to plummet than to eliminate the Mortgage Interest Deduction. What about removing Student Loan Interest? Under a 30% 'simple' rate, what tools would the government use to encourage trade in specific areas? Will state income tax deduction also be removed? This is going to punish those in a state with a high income tax more than those in states without income tax. Those are all just 'common' deductions that affect a lot of people, you could easily say 'no' to all of them and just piss off a bunch of people, but what about selling stock though? I paid $100 for the stock and I sold it for $120, do I need to pay $36 tax on that because it is a 'simple' 30% tax rate or are we allowing the cost of goods sold deduction (it's called something else I believe when talking about stocks but it's the same idea?) What about if I travel for work to tutor individuals, can I deduct my mileage expenses? Do I need to pay 30% income tax on my earnings and principal from a Roth IRA? A lot of people have contributed to a Roth with the understanding that withdrawals will be tax free, changing those rules are punishing people for using vehicles intentionally created by the government. Are we going to go around and dismantle all non-profits that subsist entirely on tax-deductible donations? Do I need to pay taxes on the employer's cost of my health insurance? What about 401k's and IRA's? Being true to a 'simple' 30% tax will eliminate all 'benefits' from every job as you would need to pay taxes on the value of the benefits. I should mention that this isn't exactly too crazy, there was a relatively recent IRS publication about businesses needing to withhold taxes from their employees for the cost of company supplied food but I don't know if it was ultimately accepted. At the end of the day, the concept of simplifying the tax law isn't without merit, but realize that the complexities of tax law are there due to the complexities of life. The vast majority of tax laws were written for a reason other than to benefit special interests, and for that reason they cannot easily be ignored. Bank of America is the worst. Once I had a joint account with another individual that I had funded out of my account to make payroll.   When I found out that he had screwed two other people by stealing the payroll money I decided to disburse it myself and transferred it back to my corporate account on which I was the only signer.  He went back to the bank and effected a withdrawal from my account to the tune of tens of thousands of dollars, put the money in the joint account and removed me as a signer.   The bank wouldn't give me my money back and I never collected from him.  Another time I tried to close my sons' accounts which were in inactive status.  Every day for a week they told me they could not close the account until it was active, but they were working on making it active.  Chase could do this in a minute.  I finally went to a branch and loudly informed the manager that maybe the bank was insolvent and that I should call the FDIC to see why they won't release my money.  He wanted to take me into his office.  I told him loudly, I know all about DDAs, Savings and CDs, I have run deposit operations for a major bank and wrote software to process them.  Just put a hold on the account, write me two cashiers check and offset them with a suspense voucher.  You do know how to write a suspense voucher don't you? It's just a general ledger entry to a suspense account.  Well he was so embarassed he would do anything to get me out of the branch and gave me the cashier's checks.  Fuck B of A. "Yes, you as the giver will owe US gift taxes if you give her that sum directly. You can reduce it by taking advantage of the threshold being by person. So, for example, if you and your wife each gave your daughter $17k, you'd individually be under the threshold and wouldn't owe gift tax, even if the money comes from and goes to the same account. Given the time of year, you could give her that now and another $34k in January (next tax year) and avoid the gift tax. If she doesn't need all the money immediately, that's the simplest solution. If she does need it all now, and you don't want to try arranging to  ""launder"" the money through relatives' gift allowances (which I think would be legal and legitimate, actually), the other solution is to set this up as an intra-family loan. Web searching that phrase will find details, but it essentially lets you spread the gift over multiple accounting years and pay income tax on a minimal amount of interest (can be under 0.3%, which you'd also gift her with) rather than paying gift tax. It does require some paperwork to document and track it properly, but it isn't bad. (I did this when making a large ""bridge loan"" to help a relative buy their new house before the old one had sold. In that case it really was a loan, though; I'm being paid back out of the proceeds from the sale.)" I took littleadv's advice and talked to an accountant today. Regardless of method of payment, my US LLC does not have to withhold taxes or report the payment as payments to contractors (1099/1042(S)) to the IRS; it is simply a business expense.  He said this gets more complicated if the recipient is working in the US (regardless of nationality), but that is not my case I don't understand the logic in the other answer, and I think it doesn't make sense, so here is my take: You pay taxes on income, not on sales price. So if you put X $ of your own money in the account and it becomes X + Y $ in the future, at the moment of liquidation, you will own taxes on the Y $. Never on the X $, as it was your own (already taxed) money to begin with. The difference between long-term and short-term gains just influences the tax rate on Y. If you donate the gain alone (the Y $) to charity, you can deduct Y from your tax base. So adding Y to your tax base and then deducting Y again obviously leaves your tax base at the old value, so you pay no extra taxes. Which seems logical, as you didn't make any money in the process. Aside from extreme cases where the deductible gain is too large a percentage from your income or negative, I don't see why this would ever be different. So you can take your original 100 $ back out and donate all gains, and be fine. Note that potential losses are seen different, as the IRA regulations are not symmetric. I used TurboTax last year. It had a section for donations where it figured out the amounts of the IRS approved values for a donation.  You would need to know the size of the television and the current condition it is in.  He's a screenshot - though it's not from the TV section.  https://turbotax.intuit.com/tax-tools/tax-tips/Taxes-101/Video--How-to-Estimate-the-Value-of-Clothing-for-IRS-Deductions/INF13870.html+&cd=8&hl=en&ct=clnk&gl=us TurboTax offers a free online tool called ItsDeductible that does the same thing (though I haven't tried it). Unfortunately, I don't have the current one with TV's to give you the range of amounts that apply to yours. --I am not affiliated with TurboTax and did not receive it for free for a review.