Confused about employee stock options: How do I afford these?
ISOs (incentive stock options) can be closed out in a cashless transaction. Say the first round vests, 25,000 shares. The stock is worth $7 but your option is to buy at $5 as you say. The broker executes and sells, you get $50,000, with no up front money.  Edit based on comment below - you know they vest over 4 years, but how long before they expire? It stands to reason the longer you are able to hold them, the better a chance the company succeeds, and the price rises.  The article Understanding employer-granted stock options (PDF) offers a nice discussion of different scenarios supporting my answer. I've been offered a package that includes 100k stock options at 5 dollars a share. They vest over 4 years at 25% a year. Does this mean that at the end of the first year, I'm supposed to pay for 25,000 shares? Wouldn't this cost me 125,000 dollars? I don't have this kind of money. At the end of the first year, you will generally have the option to pay for the shares. Yes, this means you have to use your own money. You generally dont have to buy ANY until the whole option vests, after 4 years in your case, at which point you either buy, or you are considered 'vested' (you have equity in the company without buying) or the option expires worthless, with you losing your window to buy into the company. This gives you plenty of opportunity to evaluate the company's growth prospects and viability over this time. Regarding options expiration the contract can have an arbitrarily long expiration date, like 17 years. You not having the money or not isn't a consideration in this matter. Negotiate a higher salary instead. I've told several companies that I don't want their equity despite my interest in their business model and product. YMMV.   Also, options can come with tax consequences, or none at all. its not a raw deal but you need to be able to look at it objectively. Stock options represent an option to buy a share at a given price.  What you have been offered is the option to buy the company share at a given price ($5) starting a given date (your golden handcuffs aka vesting schedule). If the company's value doubles in 1 year and the shares are liquid (i.e. you can sell them) then you've just made $125k of profit.  If the company's value has gone to zero in 1 year then you've lost nothing other than your hopes of getting rich. As others have mentioned, the mechanics of exercising the option and selling the shares can typically be accomplished without any cash involved.  The broker will do both in a single transaction and use the proceeds of the sale to pay the cost of buying the shares.  You should always at least cover the taxable portion of the transaction and typically the broker will withhold that tax anyways.  Otherwise you could find yourself in a position where you have actually lost money due to tax being owed while the shares decline in value below that tax.  You don't have to worry about that right now. Again as people have mentioned options will typically expire 10 years from vesting or 90 days from leaving your employment with the company.  I'm sure there are some variations on the theme.  Make sure you ask and all this should be part of some written contract.  I'm sure you can ask to see it if you wish.  Also typical is that stock option grants have to be approved by the board which is normally a technicality. Some general advice: the short answer is: No. you do not HAVE to pay $125,000.00 at the end of your first year. that is only the amount IF you decide to exercise.  *fine print: But if you leave or get let go (which happens quite frequently at top tier Silicon Valley firms), you lose anything that you don't exercise. you're basically chained by a pair of golden handcuffs. in other words, you're stuck with the company until a liquidation event such as IPO or secondary market selling (you can expect to spend a few years before getting anything out of your stocks) Now, it's hard to say whether or not to exercise at that time, especially given we don't know the details of the company. you only should exercise if you foresee your quitting, anticipate getting fired, AND you strongly feel that stock price will keep going up. if you're in SF bay, i believe you have 10 years until your options expire (at which point they are gone forever, but that's 10 years and usually companies IPO well within 7 years). i would recommend you get a very good tax advisor (someone that understands AMT and stock options tax loopholes/rules like the back of their hand).  I'm going to take a long shot and assume that you got an amazing offer and that you got a massive amount of ISOs from them. so i'll give this as an advice - first, congrats on owning a lot on paper today if you're still there. you chose to be an early employee at a good tech company. However, you should be more worried about AMT (alternative min tax). you will get enslaved by the IRS if you exercise your shares and can't pay the AMT. suppose, in your fictional scenario, your stock options increase 2x, on paper. you now own $1 Mil in options. but you would be paying $280000 in taxes if you chose to exercise them right now. Now, unless you can sell that IMMEDIATELY on the secondary market, i would highly advise you not to exercise right now. only exercise your ISOs when you can turn around and sell them (either waiting for IPO, or if company offers secondary market approved trading).
"&gt; A trucking company making millions of dollars a year on US highways derives more value from the roads than I do.   Trucking companies run on very slim margins (typical for a commoditized business) and the vast majority of benefit is captured by other players, employees, and the government (in the form of taxes).   Moreover, you appear to be confusing revenue and profits.  &gt; Honestly anyone who says that they don't need to pay for roads because of their level of benefit from them is limited and I will call you a liar. Unless you are living in a box in the woods 100s of miles away from civilization you absolutely rely on the road system even if you never set foot on it.   Nobody ever said this. You are inventing an argument in order to counter it. Silly.  &gt; Though at the same time a national highway system was something no business would ever make as it derives too little value for an individual business for the scale required to reach enough of the market. This is a perfect example of a project that is good for society but won't see the tab picked up by business voluntarily.   Sure. Again, you are way off on a tangent though. Nobody here has argued against infrastructure nor taxes required to fund them.   &gt; It is foolish to assume your market value increases do not rely on infrastructure to happen. As much as paper-trading inflates value, for the most part, it is still tied to some kind of real work (or rather the expectation of) being done somewhere. That assumption of ability for a corporation to serve it's shareholders is based on the fact that companies have infrastructure needs handled and that expanding delivery to three new markets won't be hampered because the company must first complete the highway to serve these markets.  Again, you seem confused about the argument. We are not arguing about the basis of stock valuations and appreciation (which you happen to be wrong on, btw). We are talking about the relative value of infrastructure gained by the wealthy vs. non-wealthy. Replace ""stock market"" with ""30 year US Treaury Bonds"". Actually, don't... the next thing I'll see from you is some kind of comment about how infrastructure forms the basis for interest rates.  &gt;The existence of infrastructure not only supports the market but allows you to exploit it. The internet here makes a great example. Prior to funding and a push by the government to standardize military and academic networks and technology as well as make microprocessors more powerful in order to stay ahead in tech race we had a mish mash of proprietary networks with very poor abilities to use them. Today we have the internet. A largely private system today however it would not exist without the involvement and funding from the government for the multiple programs that led to it's existence.  Great. Nobody ever said otherwise.  &gt; If the taxes really outweighed utility businesses would not operate in the area at all. The thing is, they don't and taxes are not preventing businesses from growing.   I said personal utility. I personally employ 40 families. I pay considerable taxes for them. They pay income and sales taxes on top of that. It's a huge amount of money the government receives that they wouldn't have had I not chosen to go into business.  Incidentally, this brings up another point. Doesn't the government owe me something for generating that many jobs? Why am I not getting a tax break?  &gt; Yes but that is because unless you are doing it ALL yourself then you did not generate that $10. As a business owner you are in charge of managing resources to help generate that $10, you yourself however did not generate that $10. You had employees, and contractors, and people managing your building, payroll and yes even taxes. Every person involved in getting the product or service from idea to the door are all part of that $10. If your efforts in that co-ordination are netting you 15% of the total then you are beating the market already and I am not sure what your problem is. If you are looking to double or triple your investments you are looking for Las Vegas not Wall St or Main St.  I see you don't understand how business works.  &gt; I think the issue I see among people with your opinion is a failure to understand 2nd and 3rd order effects. Your bubble extends to what you do in your daily life and the parts of it you visibly see and touch. The world you see and touch every day is supported and made comfortable by a whole system and people whom you will never see or know.   The issue I see among people with your opinion is that it is naive and obviously not based in any real world experience. If you had ever actually run a business, you would realize how many people get paid before you do (including the government). You have maybe a 5% chance of making an above average wage and you fight like hell every day to stay afloat.   I encourage you to open your eyes and try to see the perspective of people who are actually making a difference in this world, and not the political lowlifes and lowlife leeches who have a vested interest in seeing to it that you believe something that simply isn't true." Companies do not support their stock. Once the security is out on the wild (market), its price fluctuates according to what investors think they are worth. Support is a whole different concept, financially speaking: Support or support level refers to the price level below which, historically, a stock has had difficulty falling. It is the level at which buyers tend to enter the stock. So it is the lowest assumed price for that stock. Once it reaches its price, buyers will rush to the stock, raising its price. The company wants to keep the stock price at acceptable levels, as it can be seen as the general view of the company's health. Also several employees/executives in the company have stock or stock options, so it is in their interest to keep their stock price up. A bond that goes down in value may indicate a believe the bond issuer (government in this case) won't honor the bond when it matures. As for bonds, there is a wealth of reading in this site: Can someone explain how government bonds work? Who sets the prices on government bonds?  Basic understanding of bonds, values, rates and yields This should all be covered in your stock grant documentation, or the employee stock program of which your grant is a part.   Find those docs and it should specify how or when you can sale your shares, and how the money is paid to you.  Generally, vested shares are yours until you take action.  If instead you have options, then be aware these need to be exercised before they become shares.  There is generally a limited time period on how long you can wait to exercise.  In the US, 10 years is common. Unvested shares will almost certainly expire upon your departure of the company.  Whether your Merrill Lynch account will show this, or show them as never existing, I can't say.  But either way, there is nothing you can or should do. "First lets understand what convexity means: Convexity -  convexity refers to non-linearities in a financial model. In other   words, if the price of an underlying variable changes, the price of an   output does not change linearly, but depends on the second derivative   (or, loosely speaking, higher-order terms) of the modeling function.   Geometrically, the model is no longer flat but curved, and the degree   of curvature is called the convexity. Okay so for us idiots this means: if the price of ABC (we will call P) is determined by X and Y. Then if X decreases by 5 then the value of P might not necessarily decrease by 5 but instead is also dependent on Y (wtf$%#! is Y?, who cares, its not important for us to know, we can understand what convexity is without knowing the math behind it). So if we chart this the line would look like a curve. (clearly this is an over simplification of the math involved but it gives us an idea) So now in terms of options, convexity is also known as gamma, it will probably be easier to talk about gamma instead of using a confusing word like convexity(gamma is the convexity of options). So lets define Gamma: Gamma - The rate of change for delta with respect to the underlying asset's price. So the gamma of an option indicates how the delta of an option will change relative to a 1 point move in the underlying asset. In other words, the Gamma shows the option delta's sensitivity to market price changes. or Gamma shows how volatile an option is relative to movements in the underlying asset. So the answer is: If we are long gamma (convexity of an option) it simply means we are betting on higher volatility in the underlying asset(in your case the VIX). Really that simple? Well kinda, to fully understand how this works you really need to understand the math behind it. But yes being long gamma means being long volatility. An example of being ""long gamma"" is a ""long straddle"" Side Note: I personally do trade the VIX and it can be very volatile, you can make or lose lots of money very quickly trading VIX options. Some resources: What does it mean to be ""long gamma"" in options trading? Convexity(finance) Long Gamma – How to Make a Long Gamma Position Work for You Delta - Investopedia Straddles & Strangles - further reading if your interested. Carry(investment) - even more reading." Does this technically mean that she has to pay AMT on $400,000? Yes. Well, not exactly 400,000. She paid $1 per share, so 390,000. And if so, is %28 the AMT for this sum? (0.28 * $400,000 = $112,000)?   Or does she have to include her salary on top of that before   calculating AMT? (Suppose in the fake example that her salary is   $100,000 after 401k). All her income is included in calculating the AMT, minus the AMT exemption amount. The difference between the regular calculated tax and the calculated AMT is then added to the regular tax. Note that some deductions allowed for the regular calculation are not allowed for the AMT calculation. How does California state tax come into play for this? California has its own AMT rules, and in California any stock option exercise is subject to AMT, unless you sell the stock in the same year. Here's a nice and easy to understand write up on the issue from the FTB. When would she have to pay the taxes for this huge AMT? Tax is due when income is received (i.e.: when you exercise the options). However, most people don't actually pay the tax then, but rather discover the huge tax liability when they prepare to submit their tax return on April 15th. To avoid that, I'd suggest trying to estimate the tax and adjust your withholding using form W4 so that by the end of the year you have enough withheld. Suppose in the worst case, the company goes completely under. Does she   get her massive amounts of tax back? Or if it's tax credit, where can   I find more info on this? That would be capital loss, and only up to $3K a year of capital loss can be deducted from the general income. So it will continue offsetting other capital gains or being deducted $3K a year until it all clears out. Is there any way to avoid this tax? (Can she file an 83b election?) You asked and answered. Yes, filing 83(b) election is the way to go to avoid this situation. This should be done within 30 days of the grant, and submitted to the IRS, and a copy attached to the tax return of the grant year. However, if you're considering exercise - that ship has likely sailed a long time ago. Any advice for Little Susie on how she can even afford to pay that   much tax on something she can't even sell anytime soon? Don't exercise the options? Should she   take out a loan? (e.g. I've heard that in the extreme case, you can   find angel investors who are willing to pay all your taxes/strike   price, but want 50% of your equity? I've also heard that you can sell   your illiquid shares on SecondMarket?) Is she likely to get audited by IRS for pulling something like this? You can take a loan secured by shares you own, there's nothing illegal in it. If you transfer your shares - the IRS only cares about the taxes being paid, however that may be illegal depending on the terms and the conditions of the grant. You'll need to talk to a lawyer about your situation. I suggest talking to a licensed tax adviser (EA/CPA licensed in your State) about the specifics concerning your situation. "Great. 10% of the pre-tax 450 you'd make in a week of 40 hours' work means you could buy about 2 shares a month. I assume they pay bi-weekly, so you can qualify to buy a share.   25% 401k contribution off less than 30k annual salary is peanuts to the company, and peanuts to the employee by retirement. Competitively speaking, thats actually a rather bare-bones retirement package, isn't it?  I hope that health care waves covers deductables 100% - otherwise a yearly checkup will be 10% of your takehome that week in addition to the hours you take off work and get ""points"" under their draconian ""no days off ever"" policy." I would not hold any company stock for the company that provides your income.   This is a too many eggs in one basket kind of problem. With a discounted stock purchase plan, I would buy the shares at a 10% discount and immediately resell for a profit.   If the company prevents you from immediately reselling, I  don't know if I would invest. The risk is too great that you'll see your job lost and your 401k/investments emptied due to a single cause. What is a good resource to learn about options trading strategies? Options are a quite advanced investment form, and you'd do well to learn a lot about them before attempting to dive into this fairly illiquid market. Yale's online course in financial markets covers the Options Market and is a good starting point to make sure you've got all the basics. You may be familiar with most of it, but it's a decent refresher on lingo and Black-Scholes. How can I use options to establish some cash flow from long standing investments while minimizing capital gains expenses? This question seems designed to get people to talk about covered calls. Essentially, you sell call contracts: you let people buy things you already have at a price in the future, at their whim. They pay you for this option, though usually not much if the options aren't in the money. You can think of this as trading any return above the call option for a bit of extra cash.  I don't invest with taxable accounts, but there are significant tax consequences for options. Because they expire, there will be turnover in your portfolio, and up front income when you take the sell side. So if you trade in options with close expiration dates, you'll probably end up with a lot of short-term capital gains, which are treated as normal income. One strategy is to trade in broad-based stock index options, which have favorable tax treatments. Some people have abused this though to disguise normal income as capital gains, so it could go away. Obviously the easy approach is to just use a tax advantaged account for options trading. An ETF might also be able to handle the turnover on your behalf, for example VIX is a series of options on S&P500 options. A second strategy I've heard of is buying calls and puts at a given strike price. For example, if you bought Dec '13 calls and puts on SPX @ 115 today, it would cost you about $35 dollars. If the price moves more than 35 dollars away from 115 by DEC '13 (in either direction), you've made a profit. If you reflect on that for a bit, you'll see why VIX is considered a volatility index. I guess I should mention that shorting a stock and buying a put option at the market price are very similar, with the exception that your loss is limited to the price of the option.  Is there ever an instance where options investing is not speculative? The term 'speculative' is not well defined. For many people, the answer is no. It's very easy to just buy put options and wait for prices to fall, or call options and wait for prices to rise. Moreover, the second strategy above essentially gives you similar performance to a stock without paying full price. These all fall under the headline of increasing a risk portfolio rather than decreasing it, which I figure is a decent definition of speculation. On the other hand, there are ways to use options minimize risk rather than increase it. You can buy underwater options as portfolio insurance, if your portfolio drops below a certain amount, you still have the right to sell it at a higher one. And the Case-Schiller index is run in part, on the hopes that one day there might be a thriving market for real estate options (or futures). When you buy a home or lend money to someone to buy one, you could buy regional Case-Schiller options to protect you if the regional market tanks. But in all of these cases, it's required for someone else to take the opposite trade. Risk isn't reduced, it's traded around. So technically, there is a speculative element to these as well. I think the proper question here is whether speculation is present, but whether speculation can be put to good ends. Without speculators, the already very thin market for options would shrivel faster.