Can I donate short-stock to charity?
No. There is no asset associated with your short position, so there's nothing to gift. The short position in the stock is purely a liability. When you note that you have a profit in the position, what you mean is that the cash you made when you shorted the stock is more than enough to cover the short position. The only asset in this picture, then, is the cash you made when you entered the short position. With a short position you make your money (profit) when you buy the stocks back to close the position at a lower price than what you bought them at. As short selling is classed as speculation and not investing and you at no time own any actual assets, you cannot donate any short possition to charity. If you did want to avoid paying tax on the profits you could donate the proceeds of the profits after closing the position and thus get a tax deduction equal to the profits you made. But that raises a new and more important question, why are you trading in the first place if you are afraid to make profits in case you have to pay tax on those profits?
"Let me start with something you might dismiss as trite - Correlation does not mean Causation.  A money manager charging say, 1%, isn't likely to take on clients below a minimum level.  On the other hand, there's a long debate regarding how, on average, managed funds don't beat the averages.  I think that you should look at it this way. People that have money tend to be focused on other things. A brain surgeon making $500K/yr may not have the time, nor the inclination to want to manage her own money.  I was always a numbers person. I marveled at the difference between raising 1.1 to the 40th power, getting 45.3 (i.e. Getting 45.3 times your investment after 40 years at 10%) vs 31.4 at 9%. That 1% difference feels like nothing, but after a lifetime, 1/3 of your money has been skimmed off the top. the data show that one can do better by simply putting their money into a mix of S&P index and cash, and beat the average money manager over time, regardless of convoluted 12 asset class allocations.  Similarly - There are people who use a 'tax guy.' In quotes because I mean this as an individual whom they go to, year after year, not a storefront. My inlaws used to go to one, and I was curious what they got for their money. Each year he sent them a form. 3 pages they needed to fill in. Every cell made its way into the guy's tax program. The last year, I went with them to pick up the tax return. I asked him if he noticed that they might benefit from small Roth conversions each year, or by making some of their IRA RMD directly to charity. He kindly told me ""That's not what we do here"" and whisked us away. I planned both questions in advance. The Roth conversion was a strategy that one could agree made sense or dismiss as convoluted for some clients. But. The RMD issue was very different. They didn't have enough Schedule A deductions to itemize. Therefore the $3000 they donated each year wasn't impacting their return. By donating directly from their IRAs, this money would avoid tax. It would have saved them more than the cost of the tax guy, who charged a hefty fee, in my opinion. It seemed to me, this particular strategy should be obvious to one whose business is preparing returns." "For simplicity, let's start by just considering cash back. In general, cash back from credit cards for personal use is not taxable, but for business use it is taxable (sort of, I'll explain later). The reason is most personal purchases are made with after tax dollars; you typically aren't deducting the cost of what you purchased from your personal income, so if you purchase something that costs $100 and you receive $2 back from the CC company, effectively you have paid $98 for that item but that wouldn't affect your tax bill. However, since businesses typically deduct most expenses, that same $100 deduction would have only been a $98 deduction for business tax purposes, so in this case the $2 should be accounted for. Note, you should not consider that $2 as income though; that would artificially inflate your revenue. It should be treated as a negative expense, similar to how you would handle returning an item you purchased and receiving a CC refund. Now for your specific questions: Part 1: As a small business owner, I wish to attend an annual seminar to improve my business. I have enough credit card reward points to cover the airfare, hotel, and rental car. Will those expenses still be deductible at the value displayed on the receipt? Effectively no, these expenses are not deductible. If you deduct them they will be completely counter-acted by the ""refund"" you receive for the payments. Part 2: Does it matter if those points are accrued on my personal credit card, rather than a business credit card? This is where it gets hairy. Suppose your company policy is that employees make purchases with their own personal credit cards and submit receipts for reimbursement. In this case the employer can simply reimburse and would not know or care if the employee is racking up rewards/points/cashback. The trick is, as the employee, you must always purchase business related items normally so you have receipts to show, and if you receive cashback on the side there seems to be a ""don't ask, don't tell"" rule that the IRS is OK with. It works the same way with heavy business travelers and airline miles- the free vacations those users get as perks are not treated as taxable income. However, I would not go out of my way to abuse this ""loophole"". Typically, things like travel (airfare, hotel, car rental, meals) are expected. But I wouldn't go purchase 100 company laptops on your personal card and ask the company to reimburse you. The company should purchase those 100 laptops on a company card and effectively reduce the sale price by the cashback received. (Or more realistically, negotiate a better discount with your account rep and just cut them a check.) Part 3: Would there be any difference between credit card points and brand-loyalty points? If the rental car were paid for with points earned directly on the rental car company's loyalty system (not a CC), would that yield a different result? There is no difference. Perhaps the simplest way to think about this is you can only deduct an expense that you actually incur. In other words, the expense should show up on a bank or CC statement. This is why when you volunteer and work 10 hours for a charity, you can't call that a ""donation"" of any amount of money because there is no actual payment made that would show up on a bank statement. Instead you could have billed the charity for your 10 hours of work, and then turned around and donated that same amount back to them, but it ends up being a wash." "I know your ""pain"".  But don't worry about investing the money right now -- leave it uninvested in the short term.  You have other stuff you need to school up on.  Investment will come, and it's not that hard.  In the short term, focus on taxes.  Do some ""mock"" run-throughs of your expected end-of-year taxes (use last year's forms if this year's aren't available yet).  Must you pay estimated tax periodically throughout the year?  The tax authorities charge hefty penalties for ""forgetting"" to do it or ""not knowing you have to"".  Keep an eye out for any other government gotchas.   Do not overlook this!  This is the best investment you could possibly make.  Max out your government sanctioned retirement funds - in the US we have employer plans like 401K or Keogh, and personal plans like the IRA.  This is fairly straightforward.  Avoid any ""products"" the financial advisors want to sell you, like annuities.  Also if you have the Roth type IRA, learn the difference between that and a normal one.  There are some tricks you can do if you expect to have an ""off"" year in the future.  Charitable giving is worth considering at high income levels.  Do not donate directly to charities.  Instead, use a Donor Advised Fund.  It is a charity of its own, which accepts your tax deductible donation, and holds it.  You take the tax deduction that year.  Then later, when the spirit moves, tell your DAF to donate to the charity of your choice.   This eliminates most of the headaches associated with giving.  You don't get on the soft-hearted sucker lists, because you tell the DAF not to disclose your address, phone or email.  You don't need the charity's acknowledgement letter for your taxes, since your donation was actually to the DAF. It shuts down scams and non-charities, since the DAF confirms their nonprofit status and sends the check to their official address only. (This also bypasses those evil for-profit ""fundraising companies"".) It's a lot simpler than they want you to know.  So-called ""financial advisors"" are actually salesmen working on commission.  They urge you to invest, because that's what they sell.  They sell financial products you can't understand because they are intentionally unduly complex, specifically to confuse you.  They are trying to psych you into believing all investments are too complex to understand, so you'll give up and ""just trust them"".  Simple investments exist.  They actually perform better since they aren't burdened down with overhead and internal complexity.  Follow this rule: If you don't understand a financial product, don't buy it.   But seriously, do commit and take the time to learn investment.  You are the best friend your money will have - or its worst enemy.  The only way to protect your money from inflation or financial salesmen is to understand investment yourself. You can have a successful understanding of how to invest from 1 or 2 books. (Certainly not everything; those ingenious salesmen keep making the financial world more complicated, but you don't need any of that junk.)   For instance how do you allocate domestic stocks, foreign stocks, bonds, etc. in an IRA if you're under 40?  Well... how do smaller universities invest their endowments? They all want the same thing you do.  If you look into it, you'll find they all invest about the same.  And that's quite similar to the asset mix Suze Orman recommends for young people's IRAs.  See? Not that complicated.  Then take the time to learn why. It isn't stupid easy, but it is learnable.   For someone in your tier of income, I recommend Suze Orman's books.  I know that some people don't like her, but that segues into a big problem you'll run into:  People have very strong feelings about money.  Intense, irrational emotions.  People get it from their parents or they get sucked into the ""trust trap"" I mentioned with so-called financial advisors.  They bet their whole savings on whatever they're doing, and their ego is very involved.  When they push you toward their salesman or his variable annuity, they want you to agree they invested well.  So you kinda have to keep your head low, not listen too much to friends/family, and do your research for yourself.  John Bogle's book on mutual funds is a must-read for picking mutual funds and allocating assets.  Certain financial advisors are OK.  They are ""fee only"" advisors.  They deal with all their customers on a fee-only basis, and are not connected to a company which sells financial products.  They will be happy for you to keep your money in your account at your discount brokerage, and do your own trading on asset types (not brands) they recommend.  They don't need your password.  Here's what not to do: A good friend strongly recommended his financial advisor.  In the interview, I said I wanted a fee-only advisor, and he agreed to charge me $2000 flat rate.  Later, I figured out he normally works on commissions, because he was selling me the exact same products he'd sell to a commission (free advice) customer, and they were terrible products of course.  I fired him fast." 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. Depending on the size of the donation, you may be able to reduce taxes further by donating appreciated assets, such as stock or fund shares that have gone up a lot. That lets you dodge the capital gains tax on redeeming the shares, and if you're donating to a tax-exempt organization they don't have to pay that tax either.  And as @JoeTaxpayer has confirmed, you still get to deduct the current value of the donation, not just the basis value of those shares. So if you're donating anyway, this comes close to being Free Money in exchange for some slightly annoying paperwork. (Yet another benefit of long-term investing!) Of course folks in the top brackets sometimes set up their own tax-exempt foundations so they can decouple taking the tax break from deciding what to do with the donation. When you buy a stock, the worst case scenario is that it drops to 0.  Therefore, the most you can lose when buying a stock is 100% of your investment. When you short a stock, however, there's no limit on how high the stock can go.  If you short a stock at 10, and it goes up to 30, then you've lost 200% on your investment.  Therefore shorting stocks is riskier than buying stocks, since you can lose more than 100% of your investment when shorting. because the price might go up, but it will never be as big of a change as a regular price drop i suppose... That is not true.  Stocks can sometimes go up significantly (50-100% or more) in a very short amount of time on a positive news release (such as an earnings or a buyout announcement).  A famous example occurred in 2008, when Volkswagen stock quintupled (went up 400%) in less than 2 days on some corporate news: Porsche, for some reason, wants to control Volkswagen, and by building up its stake has driven up the price. Hedge funds, figuring the share price would fall as soon as Porsche got control and stopped buying, sold a lot of VW shares short. Then last weekend, Porsche disclosed that it owned 42.6 percent of the stock and had acquired options for another 31.5 percent. It said it wanted to go to 75 percent. The result: instant short-squeeze. The German state of Lower Saxony owns a 20 percent stake in VW, which it said it would not sell. That left precious few shares available for anyone else. The shorts scrambled to cover, and the price leaped from about €200, or about $265, to above €1,000. Yes, depending on what you're trying to achieve. If its just a symbolic gift - you can use a service like this. There are several companies providing this service, look them up, but the prices are fairly the same. You'll end up getting a real stock certificate, but it will cost a lot of overhead (around $40 to get the certificate, and then another $40 to deposit it into a brokerage account if you want to sell it on a stock exchange). So although the certificate is real and the person whose name on it is a full-blown shareholder, it doesn't actually have much value (unless you buy a Google or Apple stock, where the price is much much higher than the fees). Take into account that it takes around 2 months for the certificate to be issued and mailed to you, so time accordingly. Otherwise, you can open a custodial brokerage account, and use it to buy stocks for the minor. Both ways are secure and legal, each for its own purpose and with its own fees. "As the other answer said, the person who owns the lent stock does not benefit directly.  They may benefit indirectly in that brokers can use the short lending profits to reduce their fees or in that they have the option to short other stocks at the same terms.   Follow-up question: what prevents the broker lending the shares for a very short time (less than a day), pocketing the interest and returning the lenders their shares without much change in share price (because borrowing period was very short). What prevents them from doing that many times a day ? Lack of market.   Short selling for short periods of time isn't so common as to allow for ""many"" times a day.  Some day traders may do it occasionally, but I don't know that it would be a reliable business model to supply them.  If there are enough people interested in shorting the stock, they will probably want to hold onto it long enough for the anticipated movement to happen.   There are transaction costs here.  Both fees for trading at all and the extra charges for short sale borrowing and interest.  Most stocks do not move down by large enough amounts ""many"" times a day.  Their fluctuations are smaller.  If the stock doesn't move enough to cover the transaction fees, then that seller lost money overall.  Over time, sellers like that will stop trading, as they will lose all their money.   All that said, there are no legal blocks to loaning the stock out many times, just practical ones.  If a stock was varying wildly for some bizarre reason, it could happen."