Early Exercise and 83(b) Election
"You mention ""early exercise"" in your title, but you seem to misunderstand what early exercise really means. Some companies offer stock options that vest over a number of years, but which can be exercised before they are vested. That is early exercise. You have vested stock options, so early exercise is not relevant. (It may or may not be the case that your stock options could have been early exercised before they vested, but regardless, you didn't exercise them, so the point is moot.) As littleadv said, 83(b) election is for restricted stocks, often from exercising unvested stock options. Your options are already vested, so they won't be restricted stock. So 83(b) election is not relevant for you. A taxable event happen when you exercise. The point of the 83(b) election is that exercising unvested stock options is not a taxable event, so 83(b) election allows you to force it to be a taxable event. But for you, with vested stock options, there is no need to do this. You mention that you want it not to be taxable upon exercise. But that's what Incentive Stock Options (ISOs) are for. ISOs were designed for the purpose of not being taxable for regular income tax purposes when you exercise (although it is still taxable upon exercise for AMT purposes), and it is only taxed when you sell. However, you have Non-qualified Stock Options. Were you given the option to get ISOs at the beginning? Why did your company give you NQSOs? I don't know the specifics of your situation, but since you mentioned ""early exercise"" and 83(b) elections, I have a hypothesis as to what might have happened. For people who early-exercise (for plans that allow early-exercise), there is a slight advantage to having NQSOs compared to ISOs. This is because if you early exercise immediately upon grant and do 83(b) election, you pay no taxes upon exercise (because the difference between strike price and FMV is 0), and there are no taxes upon vesting (for regular or AMT), and if you hold it for at least 1 year, upon sale it will be long-term capital gains. On the other hand, for ISOs, it's the same except that for long-term capital gains, you have to hold it 2 years after grant and 1 year after exercise, so the period for long-term capital gains is longer. So companies that allow early exercise will often offer employees either NQSOs or ISOs, where you would choose NQSO if you intend to early-exercise, or ISO otherwise. If (hypothetically) that's what happened, then you chose wrong because you got NQSOs and didn't early exercise." I assume I can/will need to file an 83(b) election, in order to avoid   tax repercussions? What exactly will this save me from? 83(b) election is for restricted stock grants, not for stock purchases. For restricted stocks, you generally pay income tax when they vest. For startups the price difference between the time of the grant and the time of the vesting can be astronomical and by choosing 83(b) you effectively pay income tax on the value of the grant instead of the value of the vest. Then, you only pay capital gains tax on the difference between the sale price and the grant value when you sell. In your case you're exercising an option, i.e.: you're buying a stock, so 83(b) is irrelevant. What you will pay though is the tax on the difference between the strike price and the stock FMV (unless the stocks you end up buying are restricted - which would have been the case if you exercised your options early, but I don't think is going to be the case now). What steps should I take to (in the eyes of the law) guarantee that   the board has received my execution notice? The secretary of the board   is a notorious procrastinator and can be very unorganized. You should read what the grant contract/company policy says on that. Ask the HR/manager. Usually, a certified letter with return receipt should be enough, but you should verify the format, the address, and the timeframe.
You have a lot of different questions in your post - I am only responding to the request for how to value the ESPP. When valuing an ESPP, don't think about what you might sell the shares for in the future, think about what the market would charge you for that option today. In general, an option is worth much less than the underlying share itself. For the simplest example, assume you work at a public company, and your exercise price for your options is $.30, and you can only exercise those options until the end of today, and the cost of the shares on the public stock exchange is also $.30. You have the same 'strike price' as everyone else in the market, making your option worth nothing. In truth, holding that right to a specific strike price into the future does give you value, because it means you can realize the upside in share price gains, without risking any money on share losses. So, how do you value the options? If it's a public company with an active options market, you can easily compare your $.30 strike price with the value of call options in the market that have a $.30 strike price. That becomes the value to you of the option (caveat: it is unlikely you can find an exact match for the terms of your vesting period, but you should be able to find a good starting point). If it's a public company without an active options market, you will have to do a bit of estimation. If a current share is worth $.25 (so, close to your strike price), then your option is worth a little bit, but not much. Compare other shares in your industry / company size to get examples of the relative value between an option and a share. If the current share price is worth $.35, then your option is worth about $.05 [the $.05 profit you could get by immediately exercising and selling, plus a bit more for an option on a share that you can't buy in the open market]. If it's a private company, then you need to be very clear on how shares are to be valued, and what methods you have available to sell back to the company / other individuals. You can then consider as per above, how to value the option for a share, vs the share itself. Without a clear way to sell your shares of a private company [ideally through a sale directly back to the company that you are able to force them to agree on; ie: the company will buyback shares at 5x Net income for the previous year, or something like that], then the value of a small number of shares is very nebulous. There is an extremely limited market for shares of private companies, if you don't own enough to exert control. In your case, because the valuation appears to be $2/share [be sure that these are the same share classes you have the option to buy], your option would be worth a little more than $1.70, if you didn't have to wait 4 years to exercise it. This would be total compensation of about $10k, if you were able to exercise today. Many people don't end up working for an early job in their career for 4 years, so you need to consider whether how much that will reduce the value of the ESPP for you personally. Compared with salary of 90k, 10k worth of stock in 4 years may not be a heavy motivating compensation consideration. Note also that because the company is not public, the valuation of $2/share should be taken with a grain of salt. An option is freely tradable, and all options (of the same kind) are equal. If your position is 0 and you sell 1 option, your new position in that option is -1. If the counterparty to your trade buys or sells more options to close, open, or even reopen their position afterwards, that doesn't matter to your position at all. Of course there's also the issue with American and European Options. European Options expire at their due date, but American Options expire at their due date or at any time before their due date if the holder decides they expire. With American Options, if a holder of an American Option decides to exercise the option, someone who is short the same option will be assigned as the counterparty (this is usually random). Expiry is after market close, so if one of your short American Options expires early, you will need to reopen the position the next day. Keep in mind dividends for slightly increased complexity. American and European Options do not in any way refer to the continents they are traded on, or to the location of the companies. These terms simply describe the expiry rules. Investopedia states: While early exercise is generally not advisable, because the time   value inherent in the option premium is lost upon doing so, there are   certain circumstances under which early exercise may be advantageous.   For example, an investor may choose to exercise a call option that is   deeply in-the-money (such an option will have negligible time value)   just before the ex-dividend date of the underlying stock. This will   enable the investor to capture the dividend paid by the underlying   stock, which should more than offset the marginal time value lost due   to early exercise. So the question is how well do you see the time value factor here? I've talked to several very experienced accountants that deal with startup shares, stock 83(b)'s, etc. weekly (based in SF, CA) as this issue would have had a massive impact on me.  The most important part of filing an 83(b) is notifying the IRS within 30 days. The law requires the written notification within the 30 day window. Adding it to that years tax return is an IRS procedure. Forgetting to include a copy of that years tax return is apparently a common occurrence when no tax was owed (0 spread, you actually paid the FMV). And the accepted method to resolve this is to simply file a blank amendment for that years return and include the copy of the 83(b) election. "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." I have held an in the money long position on an option into expiration, on etrade, and nothing happened.   (Scalping expiring options - high risk) The option expired a penny or two ITM, and was not worth exercising, nor did I have the purchasing power to exercise it. (AAPL) From etrade's website: Here are a few things to keep in mind about exercises and assignments: Equity options $0.01 or more in the money will be automatically   exercised for you unless you instruct us not to exercise them. For   example, a September $25 call will be automatically exercised if the   underlying security's closing price is $25.01 or higher at expiration.   If the closing price is below $25.01, you would need to call an   E*TRADE Securities broker at 1-800-ETRADE-1 with specific instructions   for exercising the option. You would also need to call an E*TRADE   Securities broker if the closing price is higher than $25.01 at   expiration and you do not wish to exercise the call option. Index   options $0.01 or more in the money will be automatically exercised for   you unless you instruct us not to exercise them. Options that are out   of the money will expire worthless. You may request to exercise   American style options anytime prior to expiration. A request not to   exercise options may be made only on the last trading day prior to   expiration. If you'd like to exercise options or submit   do-not-exercise instructions, call an E*TRADE Securities broker at   1-800-ETRADE-1. You won't be charged our normal fee for   broker-assisted trades, but the regular options commission will apply.   Requests are processed on a best-efforts basis.  When equity options are exercised or assigned, you'll receive a Smart   Alert message letting you know. You can also check View Orders to see   which stock you bought or sold, the number of shares, and the strike   price.  Notes: If you do not have sufficient purchasing power in your account   to accept the assignment or exercise, your expiring options positions   may be closed, without notification, on the last trading day for the   specific options series. Additionally, if your expiring position is   not closed and you do not have sufficient purchasing power, E*TRADE   Securities may submit do-not-exercise instructions without   notification. Find out more about options expiration dates. Almost certainly not on these councils, which are for little more than show. I believe one of the members of this council said this week that they've never actually even had a meeting.  So he's having trouble holding on to people who are only symbolically part of the administration and don't even have to do anything. sure sounded like it.  I'm going to guess Hillary is tight with Janet and October's debt ceiling juncture is going herald the start ball buster season (I'm thinking the repubs rubber stamp an increase while the Fed puts all 2+ trillion of roll overs on hold until midterms).  The resulting bond auction failures should be fun to watch.  Remind me how much of the treasury's debt auctions are dedicated to paying just the interest?  First the interest payments stop (technical default), then the principal disappears (actual default).  Could be a bad time to be in bonds, period.