Using stock options to lower income tax in the USA?
You're talking about NQO - non-qualified stock options. Even assuming the whole scheme is going to work, the way NQO are taxed is that the difference between the fair market value and the strike price is considered income to you and is taxed as salary. You'll save nothing, and will add a huge headache and additional costs of IPO and SEC regulations.
But investing into your own company is already a tax deductible event. Expenditures like Research &amp; Development, employee compensation, and acquiring new equipment are all things that reduce taxable income.  https://www.usatoday.com/story/money/markets/2016/05/20/third-cash-owned-5-us-companies/84640704/  &gt; Apple (AAPL), Microsoft (MSFT), Alphabet (GOOGL), Cisco Systems (CSCO) and Oracle (ORCL) are sitting on $504 billion, or 30%, of the $1.7 trillion in cash and cash equivalents held by U.S. non-financial companies in 2015, according to an analysis released Friday by ratings agency Moody's Investors Service.  That's even more cash concentration than in previous years, as these five companies held 27% of cash in 2014 and 25% in 2013. Apple alone is holding more cash and investments than eight of the 10 entire industry sectors.  1/3 of all dollars created by the US Federal Reserve banking system (physically minted or otherwise) is collectively held by 5 companies. Companies exist to accumulate wealth and will seek to avoid unnecessary expenditures, which includes taxes.  The corporate income tax rate is 35%. For individuals, the top income tax bracket (for every dollar of income above $400,000) is 39.6%.  I argue that dropping the top individual income tax bracket down to 34% will not materially affect these companies (paying 35% income tax) from continuing to just sit on a ludicrous sum of wealth. "You have multiple issues buried within this question. First, we don't know your tax bracket. For my answer, I'll assume 25%. This simply means that in 2016, you'll have a taxable $37,650 or higher.  The interesting thing is that losses and gains are treated differently. A 25%er's long term gain is taxed at 15%, yet losses, up to $3000, can offset ordinary income. This sets the stage for strategic tax loss harvesting. In the linked article, I offered a look at how the strategy would have resulted in the awful 2000-2009 decade producing a slight gain (1%, not great, of course) vs the near 10% loss the S&P suffered over that time. This was by taking losses in down years, and capturing long term gains when positive (and not using a carried loss).  Back to you - a 15%er's long term gain tax is zero. So using a gain to offset a loss makes little sense. Just as creating a loss to offset the gain. The bottom line? Enjoy the loss, up to $3000 against your income, and only take gains when there's no loss. This advice is all superseded by my rule ""Don't let the tax tail wag the investing dog."" For individual stocks, I would never suggest a transaction for tax purposes. You keep good stocks, you sell bad ones. Sell a stock to take a short term loss only to have it recover in the 30 day waiting period just once, and you'll learn that lesson. Learn it here for free, don't make that mistake at your own expense." If you make 100K in the U.S., you are most definitely NOT paying 25.7% tax federally. Only money that you made over 37.5K is even charged at 25% AND you didn't even factor in that you get deductions which decrease your effective tax rate. Where are you pulling your numbers? The top long-term capital gains tax rate will rise to 20% effective 1 Jan, 2011, unless Congress decides to do something about it before then. (Will they? Who knows!! There's been talk about it, but, well, it's Congress. They don't even know what they're going to do.)  Anyway. The rules about when you can sell stock are mostly concerned with when you can realize a capital loss: if you sell a stock at a loss and then re-buy it for tax purposes within 30 days, it's a wash sale and not eligible for a deduction. However, I don't believe this applies to any stocks once you realize a gain - once you've realized the gain and paid your tax for it, it's all yours, locked in at whatever rate. Your replacement stock will be subject to short-term capital gains for the next year afterwards, and you might need to be careful with identifying the holding period on different lots of your stock, but I don't believe there will be any particular trouble. Please do not rely entirely on my advice and consult also with your tax preparer or lawyer. :) And the IRS documentation: Special Addendum for Nov/Dec 2012! Spoiler alert! Congress did indeed act:   they extended the rates, but only temporarily, so now we're looking at   tax hikes starting in 2013 instead, only the new top rate++ will be something   like 23.8% on account of an extra 3.8% medicare tax on passive earnings (brought to you via Obamacare   legislation). But the year and the rates' specifics aside, same thing   still applies. And the Republican house and Democratic senate/President are still duking it out. Have fun. ++ 3.8% surtax applies to the lesser of (a) net investment income (b) income over $200,000 ($250k if married). 20% tax rate applies to people in the 15% income tax bracket for ordinary income or higher. Additional tax discounts for property held over 5 years may be available. Consult tax law and your favorite tax professional and prepare to be confused. Oh it definitely makes sense on a state level and from my experience working taxes I would say it is much more prevalent to the extent I would have to bet every Fortune 1000 company does it.  You can completely eliminate State Income Tax in many states (although states are rapidly closing the loopholes) which at corporate tax rates for most states between 6 and 8% this turns into a lot of money. If so, are there ways to reduce the amount of taxes owed? Given that it's currently December, I suppose I could sell half of what I want now, and the other half in January and it would split the tax burden over 2 years instead, but beyond that, are there any strategies for tax reduction in this scenario? One possibility is to also sell stocks that have gone down since you bought them.  Of course, you would only do this if you have changed your mind about the stock's prospects since you bought it -- that is, it has gone down and you no longer think it will go up enough to be worth holding it.  When you sell stocks, any losses you take can offset any gains, so if you sell one stock for a gain of $10,000 and another for a loss of $5,000, you will only be taxed on your net gain of $5,000. Even if you think your down stock could go back up, you could sell it to realize the loss, and then buy it back later at the lower price (as long as you're not worried it will go up in the meantime).  However, you need to wait at least 30 days before rebuying the stock to avoid wash sale rules.  This practice is known as tax loss harvesting. Welcome to the real world :-)  There really aren't all that many ways for ordinary employees to lower taxes.  You could put more in your 401k, buy a house (for the mortgage interest deduction, which lets you deduct some other things instead of taking standard deduction), or move to a different state to get rid of the state tax. Restricted Stock Units are different from stock options because instead of buying them at a particular strike price, you receive the actual shares of stock. They are taxed as ordinary income at the time that the restriction is lifted (you don't have to sell them to be taxed). Usually, you can choose to have a percentage of the stock withheld to cover tax withholding or pay for the withholding out of pocket (so you can retain all of your shares). No. Black Scholes includes a number of variables to calculate the value of the derivative but taxation isn't one of them. Whether you are trading options or futures, the dividend itelf may be part of the equation, but not the tax on said dividend. "Hence why keeping the capital gains tax rate down is not such a bad idea. Sure, it may benefit ""rich"" people, but it will also allow RESPONSIBLE low and middle class income families to reinvest their capital gains and accumulate more wealth." "Do you have other income that you are not considering?  Interest and dividends would be an example, but there are all sorts of options.   Also with your witholding is it set up such that your employers have any idea of your tax bracket ultimately based on your combined incomes?  Usually what they do is take out money assuming you will be in the tax bracket of any given paycheck spread out over the course of a year.  For example, for federal I had an option to select (in an online form that fills out my W4 for me) ""married: withold at higher single rate"" and did to try and cover this fact.  Eventually I may end up having to calculate my own witholding to fix a too-low problem like yours." You should get a 1099-MISC for the $5000 you got.  And your broker should send you a 1099-B for the $5500 sale of Google stock. These are two totally separate things as far as the US IRS is concerned. 1) You made $5000 in wages. You will pay income tax on this as well as FICA and other state and local taxes. 2) You will report that you paid $5000 for stock, and sold it for $5500 without holding it for one year. Since this was short term, you will pay tax on the $500 in income you made. These numbers will go on different parts of your tax form.  Essentially in your case, you'll have to pay regular income tax rates on the whole $5500, but that's only because short term capital gains are treated as income.  There's always the possibility that could change (unlikely).  It also helps to think of them separately because if you held the stock for a year, you would pay different tax on that $500.  Regardless, you report them in different ways on your taxes. Note that you're asking about withholding, not about taxing.  Withholding doesn't mean this is exactly the tax you'll pay: it means they're withholding a certain amount to make sure you pay taxes on it, but the tax bill at the end of the year is the same regardless of how you choose to do the withholding.  Your tax bill may be higher or lower than the withholding amount. As far as tax rate, that will be the same regardless - you're just moving the money from one place to the other.   The only difference would be that your tax is based on total shares under the plan - meaning that if you buy 1k shares, for example, at $10, so $1,500 discounted income, if you go the payroll route you get (say) $375 withheld.  If you go the share route, you either get $375 worth of stock (so 38 shares) withheld (and then you would lose out on selling that stock, meaning you don't get quite as much out of it at the end) or you would ask them to actually buy rather more shares to make up for it, meaning you'd have a slightly higher total gain.  That would involve a slightly higher tax at the end of it, of course. Option 1:  Buy and then sell $10000 worth, share-based withholding.  Assuming 15% profit, and $10/share at both points, then buy/sell 1000 shares, $1500 in profit to take into account, 38 shares' worth (=$380) withheld.  You put in $8500, you get back $9620, net $1120.   Option 2:  Buy and then sell $13500 worth, share based withholding.  Same assumptions.  You make about $2000 in pre-tax profit, meaning you owe about $500 in tax withholding.  Put in $11475, get back $13000, net $1525.  Owe 35% more tax at the end of the year, but you have the full $1500 to spend on whatever you are doing with it. Option 3:  Buy and then sell $1000 worth, paycheck withholding.  You get the full $10000-$8500 = $1500 up front, but your next paycheck is $375 lighter.  Same taxes as Option 1 at the end of the year. Hundreds of millions of stock options isn't hundreds of millions of income yet though. And once they cash out they do get taxed as income so it's effectively the same. If we taxed the stock options it would be double taxation.  I know it's ridiculous how much money they make still though something has to be done but just pointing that out. That is a weird one.  Typically one never needs to layout cash to exercise an option.  One would only choose to use option 1, if one is seeking to buy the options.  This would occur if an employee was leaving a company, would no longer be eligible for the ISO (and thereby forfeit any option grant), and does not want to exercise the options.   However, what is not weird is the way income tax works, you are taxed on your income in the US.   I assume you are talking about the US here. So if you exercise 10K shares, if under either option, you will be taxed on the profit from those share.   Profit = (actual price - strike price) * shares - fees