Why is RSU tax basis based on remaining shares after shares are witheld?
You only got 75 shares, so your basis is the fair market value of the stock as of the grant date times the number of shares you got: $20*75.  Functionally, it's the same thing as if your employer did this: As such, the basis in that stock is $1,500 ($20*75). The other 25 shares aren't yours and weren't ever yours, so they aren't part of your basis (for net issuance; if they were sell to cover, then the end result would be pretty similar, but there'd be another transaction involved, but we won't go there).  To put it another way, suppose your employer paid you a $2000 bonus, leaving you with a $1500 check after tax withholding. Being a prudent person and not wishing to blow your bonus on luxury goods, you invest that $1500 in a well-researched investment. You wouldn't doubt that your cost basis in that investment at $1500. Here is how it should look: 100 shares of restricted stock (RSU) vest. 25 shares sold to pay for taxes. W2 (and probably paycheck) shows your income going up by 100 shares worth and your taxes withheld going up by 25 shares worth. Now you own 75 shares with after-tax money. If you stop here, there would be no stock sale and no tax issues.  You'd have just earned W2 income and withheld taxes through your W2 job. Now, when you sell those 75 shares whether it is the same day or years later, the basis for those 75 shares is adjusted by the amount that went in to your W2.   So if they were bought for $20, your adjusted basis would be 75*$20.
from what i understand, which is not much, some companies use some of their own company shares as securitisation for loans. If the share price decreases, the security in the loan decreases, which means the company would need to find new capital. It can create a vicious cycle if the fall in share price is the result of operational concerns. No Tax would have been deducted at the time of purchase/sale of shares. You would yourself be required to compute your tax liability and then pay taxes to the govt. In case the shares sold were held for less than 1 year - 15% tax on capital gains would be levied. In case the shares sold were held for more than 1 year - No Tax would be levied and the income earned would be tax free. PS: No Tax is levied at the time of purchase of shares and Tax is only applicable at the time of sale of shares. There can be a good reason if you own shares issued in a different country: For example, if you are in the UK and own US shares and take the dividend payments, you get some check in US dollars that you will have to exchange to UK£, which means you pay fees - mostly these fees are fixed, so you lose a significant percentage of your dividends. By reinvesting and selling shares accumlated over some years, you got one much bigger check and pay only one fee. I believe that article provides some good reasons, though it may be a bit light on technical details and there are likely other reasons a company would do it. So, if they can finance for less then they would lose to taxes by bringing the money home and they do not take on too much debt, this will likely work just fine and increase share holder value. Hopefully, someone else can provide some other reasonable scenarios. The bottom line is that it does not matter how they finance the share buybacks and/or dividend payments as long as they do not shoot themselves in the foot while doing it. Your question is missing information. The most probable reason is that the company made a split or a dividend paid in stock and that you might be confusing your historical price (which is relevant for tax purposes) with your actual market price. It is VERY important to understand this concepts before trading stocks. The key point is from the penultimate sentence in your second paragraph: for which you have already paid taxes When you receive a dividend or realise a capital gain, you get taxed on that then, and you shouldn't have to pay taxes on it again in future. So the cost basis gets adjusted to reflect that. Of course, this calculation does not take into consideration the fact that once the rights are issues, the price of the shares will drop. Usually this drop corresponds to the discount. Therefore, if a rights issue is done correctly share price before issuance-discount=share price after issuance. In this result, noone's wealth changes because shareholders can then sell their stock and get back anything they had to put in. "The main thing is the percentage of the company represented by the shares. Number of shares is meaningless without total shares. If you compute percentage and total company value you can estimate the value of the grant. Or perhaps more useful for a startup is to multiple the percentage by some plausible ""exit"" value, such as how much the company might sell for or IPO for. Many grants expire when or soon after you leave the company if you don't ""cash out"" vested shares when you leave, this is standard, but do remember it when you leave.  The other major thing is vesting. In the tech industry, vesting 1/4 after a year and then the rest quarterly over 3 more years is most common." Nominal. What you say is true, but I'm guessing it would be too complicated to modelate. Plus, a shareholder of a very large company would not necessarily experience said loss if he/she sells the stock in small chunks at a time. No, you're not missing anything. RSUs are pretty simple when it comes to taxes. They are taxed as compensation at fair market value when they vest, basically equivalent to the company giving you a cash bonus and then using it to buy company stock. The fair market value at vesting then becomes your cost basis. Assuming the value has increased since vesting, selling the shares that vested at least a year ago (to qualify for lower long-term capital gains tax rates) with the highest cost basis with result in the minimum taxes. "Stocks (among other property) currently is allowed a ""stepped-up basis"" when valuing for estate tax purpose.  From the US IRS web page: To determine if the sale of inherited property is taxable, you must first determine your basis in the property. The basis of property inherited from a decedent is generally one of the following: The fair market value (FMV) of the property on the date of the decedent's death. The FMV of the property on the alternate valuation date if the executor of the estate chooses to use alternate valuation. See the Instructions for Form 706, United States Estate (and Generation-Skipping Transfer) Tax Return. If you or your spouse gave the property to the decedent within one year before the decedent's death, see Publication 551, Basis of Assets. Your question continues ""the person that died still has to pay taxes on their profits in the year they died, right?"" Yes. The estate would be subject to tax on realized gains/losses prior to death." Any time there is a share adjustment from spin-off, merger, stock split, or reverse slit; there is zero chance for the stockholders to hang on to fractional shares. They are turned into cash.   For the employees in the 401K program or investors via a mutual fund or ETF this isn't a problem. Because the fraction of a share left over is compared to the thousands or millions of shares owned by the fund as a collective. For the individual investor in the company this can be a problem that they aren't happy about.  In some cases the fractional share is a byproduct that will result from any of these events. In the case of a corporate merger or spin-off most investors will not have an integer number of shares, so that fraction leftover that gets converted to cash isn't a big deal. When they want to boost the price to a specific range to meet a regulatory requirement, they are getting desperate and don't care that some will be forced out. In other cases it is by design to force many shareholders out. They want to go private. They to 1-for-1000 split. If you had less than 1000 shares pre-split then you will end up with zero shares plus cash. They know exactly what number to use. The result after the split is that the number of investors is small enough they they can now fall under a different set of regulations. They have gone dark, they don't have to file as many reports, and they can keep control of the company.  Once the Board of Directors or the majority stockholders votes on this, the small investors have no choice. From the instructions: If you do not need to make any adjustments to the basis or type of   gain or loss (short-term or long-term) reported to you on Form 1099-B   (or substitute statement) or to your gain or loss for any transactions   for which basis has been reported to the IRS (normally reported on   Form 8949 with box A checked), you do not have to include those   transactions on Form 8949. Instead, you can report summary information   for those transactions directly on Schedule D. For more information,   see Exception 1, later. However, in case of ESPP and RSU, it is likely that you actually do need to make adjustments. Since 2014, brokers are no longer required to track basis for these, so you better check that the calculations are correct. If the numbers are right and you just summarized instead of reporting each on a separate line, its probably not an issue. As long as the gains reported are correct, no-one will waste their time on you. If you missed several thousand dollars because of incorrect calculations, some might think you were intentionally trying to hide something by aggregating and may come after you. It's important to remember what a share is.  It's a tiny portion of ownership of a company. Let's pretend we're talking about shares in a manufacturing company.  The company has one million shares on its register.  You own one thousand of them.  That means that you own 1/1000th of the company. These shares are valued by the market at $10 per share.  The company has machinery and land worth $1M.  That means that for every dollar of the company you own, 10c of that value is backed by the physical assets of the company.  If the company closed shop tomorrow, you could, in theory at least, get $1 back per share.  The other $9 of the share value is value based on speculation about the future and current ability of the company to grow and earn income. The company is using its $1M in assets and land to produce goods which cost the company $1M in ongoing costs (wages, marketing, raw cost of goods etc...) to produce and make $2M per year in sales.  That means the company is making a profit of $1M per annum (let's assume for the sake of simplicity that this profit is after tax). Now what can the company do with its $1M profit?  It can hand it out to the owners of the company (which means you would get a $1 dividend each year for each share that you own) or it can re-invest that money into additional equipment, product lines or something which will grow the business.  The dividend would be nice, but if the owners bought $500k worth of new machinery and land and spent another $500k on ongoing costs and next year we would end up with a profit of $1.5M. So in ten years time, if the company paid out everything in dividends, you would have doubled your money, but they would have machines which are ten years older and would not have grown in value for that entire time.  However, if they reinvested their profits, the compounding growth will have resulted in a company many times larger than it started. Eventually in practice there is a limit to the growth of most companies and it is at this limit where dividends should be being paid out.  But in most cases you don't want a company to pay a dividend.  Remember that dividends are taxed, meaning that the government eats into your profits today instead of in the distant future where your money will have grown much higher. Dividends are bad for long term growth, despite the rather nice feeling they give when they hit your bank account (this is a simplification but is generally true). TL;DR - A company that holds and reinvests its profits can become larger and grow faster making more profit in the future to eventually pay out.  Do you want a $1 dividend every year for the next 10 years or do you want a $10 dividend in 5 years time instead? "You are correct that a share of stock in a company has zero intrinsic value.  Even if the company typically pays dividends, there's no guarantee that it will continue to do so.  A share's only worth comes from: So that's one step better than a Ponzi scheme, because in a Ponzi scheme there's not actually any value present behind the scenes, making option (2) literally impossible. In this way company stock is similar to paper money.  It's only worth something because people believe it's worth something. Slightly better than company stock is company bonds.  Since a bond is a contract between you and the company, if the company should go out of business then bondholders at least get to stand near the front of the line when the company's assets are liquidated. I work in finance, and the vast majority of my colleagues agree that the secondary stock market (what the average citizen simply calls ""the stock market"") is a giant confidence game.  And yet it's so profitable to believe in the value of equities the way everyone else does, that we all happily pretend these ones and zeroes we move around have actual value."