Perform exercise-and-hold AND exercise-and-sell-to-cover?
"The simplest thing to do here is to speak to your employer about what is allowed.  This should be spelt out in your company's ""Stock Options Plan"" documentation.  In particular, this document will include details of the vesting schedule.  For example, the schedule may only allow you to exercise 25% in the first year, 25% in the second year, and the remainder in the third year. Technically I can see no reason to prevent you from the mix-and-match approach you are suggesting. However, this may not be the case according to the schedule specification." Ask the folks administering your plan. They're the ones who define and implement the available choices for that specific plan.
"Yes, if it's an American style option. American style options may be exercised at any time prior to expiration (even if they're not in-the-money). Generally, you are required to deliver or accept delivery of the underlying by the beginning of the next trading day. If you are short, you may be chosen by the clearinghouse to fulfill the exercise (a process called ""assignment""). Because the clearinghouse is the counter-party to every options trade, you can be assigned even if the specific person who purchased the option you wrote didn't exercise, but someone else who holds a long position did. Similarly, you might not be assigned if that person did exercise. The clearinghouse randomly chooses a brokerage to fulfill an assignment, and the brokerage will randomly choose an individual account. If you're going to be writing options, especially using spreads, you need to have a plan ahead of time on what to do if one of your legs gets assigned. This is more likely to happen just before a dividend payment, if the payment is more than the remaining time value." Vesting As you may know a stock option is the right to acquire a given amount of stock at a given price.  Actually acquiring the stock is referred to as exercising the option.  Your company is offering you options over 200,000 shares but not all of those options can be exercised immediately. Initially you will only be able to acquire 25,000 shares; the other 175,000 have conditions attached, the condition in this case presumably being that you are still employed by the company at the specified time in the future.  When the conditions attached to a stock option are satisfied that option is said to have vested - this simply means that the holder of the option can now exercise that option at any time they choose and thereby acquire the relevant shares. Dividends Arguably the primary purpose of most private companies is to make money for their owners (i.e. the shareholders) by selling goods and/or services at a profit.  How does that money actually get to the shareholders?  There are a few possible ways of which paying a dividend is one.  Periodically (potentially annually but possibly more or less frequently or irregularly) the management of a company may look at how it is doing and decide that it can afford to pay so many cents per share as a dividend.  Every shareholder would then receive that number of cents multiplied by the number of shares held. So for example in 4 years or so, after all your stock options have vested and assuming you have exercised them you will own 200,000 shares in your company.  If the board declares a dividend of 10 cents per share you would receive $20,000.  Depending on where you are and your exact circumstances you may or may not have to pay tax on this. Those are the basic concepts - as you might expect there are all kinds of variations and complications that can occur, but that's hopefully enough to get you started. "Exercising an option early if you can't sell the underlying stock being purchased is generally not advisable. You're basically locking in the worst price you can possibly pay, plus you're losing the time value on your money (which is, admittedly fairly low right now, but still). Let's say you have a strike price of $50.  I get that you believe the stock to be worth more than $50.  Let's assume that that's probably, but not certainly right. Whether it's worth $51, $151, or $5,100 when your options are going to expire, you still get the profit of $1, $101, or $5,050 if you wait until expiration and exercise then.  By exercising now, you're giving up two things: The interest on the money you pay to exercise from now until expiration. The guarantee that you can't lose anything.    If you buy it now, you get all the upside above your strike, but have all the downside below it. If you buy it later (at expiration), you still have all the upside above your strike, but no downside - in the (assumed to be unlikely) event that it's worth less than the strike you can simply do nothing, instead of having something you bought at the strike that's worth less now and taking that loss.  By exercising early, you take on that loss risk, and give up the interest (or ""carry"" on the money you spend to exercise) for no additional updside. It's possible that there are tax benefits, as other posters mention, but the odds that ""starting the clock"" for LTCG is worth as much as the ""optionality"", or loss protection, plus the ""carry"", or interest that you're giving up is fairly unlikely." "Yes, you would pay no taxes at the time of purchase. In fact, this is not uncommon. Many early employees of startup companies are offered stock options that can be ""early-exercised"" (exercised before they vest). In such a case, an employee who exercises immediately upon grant (and assuming the exercise price of the option is the FMV at the time of grant) purchases the stock at FMV, and there no no tax paid when filing 83(b) election." "When there is a trade the shares were both bought and sold. In any trade on the secondary market there has to be both a buyer and a seller for the trade to take place. So in ""lasttradesize"" a buyer has bought the shares from a seller." "Usually, the amswer to ""why sell it"" is ""to maintain the specific distribution balance, or to track the index, that this fund was designed to offer."" A ""buy and hold"" fund could only buy when users are actively putting money into it. That limits their ability to follow those approaches.  And I think there would be problems msking withdrawls/redeptions ""fair"", in terms of what shares are sold and how the costs for selling them are distributed, that don't arise for a single buy-and-hold investor. If you're willing to accept the limitations of the former, and can overcome the latter, it's an interesting idea...  But note that one of the places index funds save money is that, since the composition of indexes changes rately, they are already operating mostly in buy-and-hold mode.It's unclear how much your variant would save. Worth exploring in greater depth, though. I think." "Many companies (particularly tech companies like Atlassian) grant their employees ""share options"" as part of their compensation. A share option is the right to buy a share in the company at a ""strike price"" specified when the option is granted. Typically these ""vest"" after 1-4 years so long as the employee stays with the company. Once they do vest, the employee can exercise them by paying the strike price - typically they'd do that if the shares are now more valuable. The amount they pay to exercise the option goes to the company and will show up in the $2.3 million quoted in the question." "You've described the process fairly well.  It's tough to answer a question that ultimately is 'how is this fair?' It's fair in that it's part of the known risk. And for the fact that it applies to all, pretty equally. In general, this is not very common. (No, I don't have percents handy, I'm just suggesting from decades of trading it's probably occurring less than 10% of the time). Why? Because there's usually more value to the buyer in simply selling the option and using the proceeds to buy the stock. The option will have 2 components,  its intrinsic value (""in the money"") and the time premium. It takes the odd combination of low-to-no time premium, but desire of the buyer to own the stock that makes the exercise desirable."