Anticipating being offered stock options in a privately held company upon employment. What questions should I ask?
The company doesn't necessarily have to go public. They can also be worth money if the company is acquired. Also keep in mind that even if the company does eventually go public, your shares can essentially be wiped out by a round of pre-IPO funding that gives the company a low valuation. You could ask: I've had stock options at two different jobs.   If you are not getting a significant ownership stake, but rather just a portion of options as incentive to come work there, I would value them at $0.    If you get the same salary and benefits, but no stock options at another company and you like the other company better, I'd go to the other company. I say this because there are so many legal changes that seem to take value from you that you might as well not consider the options in your debate. That being said, the most important question I'd want to know is what incentive does the company have to going public or getting bought?    If the company is majority owned by investors, the stock options are likely to be worth something if you wait long enough.   You are essentially following someone else's bet.    If the company is owned by 2 or 3 individuals who want to make lots of money, they may or may not decide to sell or go public. Good questions. I can only add that it may be valuable if the company is bought, they may buy the options. Happened to me in previous company.
I've been through two instances where I worked for a public company that was merged (for stock) into another company.  In both cases the options I had were replaced with equivalent options in the merged company with the number of shares and strike price adjusted at the same rate as the actual stock was converted, and the vesting terms remained essentially the same.  In other words, the options before and after were in essence equivalent. The general rule with stock options is that it's best to wait until expiration to exercise them.  The rationale depends on a few factors and there are exceptions. Reasons to wait: There would be cases to exercise early: Tax implications should be checked with a professional advisor specific to your situation. In the employee stock option plans that I have personally seen, you get regular income tax assessed between exercise price and current price at the time you exercise.  Your tax basis is then set to the current price.  You also pay capital gains tax when you eventually sell, which will be long or short term based on the time that you held the stock. (The time that you held the options does not count.)  I believe that other plans may be set up differently. I agree with the other comments that you should not buy/hold your company stock even if given at a discount. If equity is provided as part of the compensation package (Options/Restrictive Stock Units RSU)then this rule does not apply. As a matter of diversification, you should not have majority equity stake of other companies in the same sector (e.g. technology) as your employer. Asset allocation and diversification if done in the right way, takes care of the returns. Buying and selling on the same day is generally not allowed for ESPP. Taxation headaches. This is from personal experience (Cisco Systems). I had options issued in Sept 2008 at 18$ which vested regularly. I exited at various points - 19$,20$,21$,23$ My friend held on to all of it hoping for 30$ is stuck. Options expire if you leave your employment. ESPP shares though remain. In the case you mentioned, where a private company owners will take debt with the purpose of  buying out other owners, is this done through a share repurchases program (I understand private companies issue them, even though it's rare)? Thank you for the insights. "Many thanks for thedetailed  response, appreciate it. But I am still not clear on the distinction between a public company and the equity holders. Isn't a public company = shareholders + equity holders? Or do you mean ""company"" = shareholders+equity holders + debt holders?" This situation sounds better than most, the company it seems likely to be profitable in the future.  As such it is a good candidate to have a successful IPO.   With that your stock options are likely to be worth something.  How much of that is your share is likely to be very small.  The workers that have been their since the beginning, the venture capitalist, and the founders will make the majority of profits from an IPO or sale.  Since you and others hired at a similar time as you are assuming almost no risk it is fair that your share of the take is small.   Despite being 1/130 employees expect your share of the profits to be much smaller than .77%.  How about we go with .01%?   Lets also assume that they go public in 2.5 years and that revenues during that time continue to increase by about 25M/year.  Profit margins remains the same.  So revenues to 112M, profits to 22.5M. Typically the goal for business is to pay no more than 5 times profits, that could be supplanted by other factors, but let's assume that figure.  So about 112M from the IPO.  So .01% of that is about 11K.  That feels about right. Keep in mind there would be underwriting fees, and also I would discount that figure for things that could go wrong.  I'd be at about 5K. That would be my expected value figure, 5K.  I'd also understand that there is a very small likelihood that I receive that amount.  The value received is more likely to be zero, or enough to buy a Ferarri. There might also be some value in getting to know these people.  If this fails will their next venture be a success. In my own life, I went to work for a company that looked great on paper that just turned out to be a bust.  Great concept, horrible management, and within a couple of years of being hired, the company went bust.  I worked like a dog for nothing. It depends.  If you accept the offer, then your stock will cease existing.  If you reject the offer, then you will become a minority shareholder.  Depending on the circumstances, you could be in the case where it becomes illegal to trade your shares.  That can happen if the firm ceases to be a public company.  In that case, you would discount the cash flows of future dividends to determine worth because there would be no market for it. If the firm remained public and also was listed for trading, then you could sell your shares although the terms and conditions in the market would depend on how the controlling firm managed the original firm. Its important that you carefully read the agreement, if you accept the job. The options agreement will usually specify the vesting schedule, the strike price, and the number of options you will have.  When you start vesting options, you can choose to buy stock at the strike price. When you do exercise the options, your employer will likely withhold state and federal income tax. The strike price will hopefully be well below the market price.  Unlike stock, when your employment ends, you usually are not able to hold on to your options. There's typically a small window of time in which you can exercise your options. You should read this part of the agreement carefully and plan accordingly. Assuming this is a public company, i'd recommend reading the analyst calls from the last several quarters. This will give you an idea of what investors, and therefor likely the board and senior leadership, are focused on at a very high level. Youre an intern, so dont feel like you need to blow the doors off, but showing that you are aware of the company's major objectives and asking some thoughtful questions about them is probably a good start. "This is several questions wrapped together: How can I diplomatically see the company's financial information? How strong a claim does a stockholder or warrantholder have to see the company's financials? What information do I need to know about the company financials before deciding to buy in? I'll start with the easier second question (which is quasi implicit).  Stockholders typically have inspection rights.  For example, Delaware General Corporate Law § 220 gives stockholders the right to inspect and copy company financial information, subject to certain restrictions. Check the laws and corporate code of your company's state of incorporation to find the specific inspection right.  If it is an LLC or partnership, then the operating agreement usually controls and there may be no inspection rights.  If you have no corporate stock, then of course you have no statutory inspection rights.  My (admittedly incomplete) understanding is that warrantholders generally have no inspection rights unless somehow contracted for.  So if you vest as a corporate stockholder, it'll be your right to see the financials—which may make even a small purchase valuable to you as a continuing employee with the right to see the financials.  Until then, this is probably a courtesy and not their obligation. The first question is not easy to answer, except to say that it's variable and highly personal for small companies.  Some people interpret it as prying or accusatory, the implication being that the founders are either hiding something or that you need to examine really closely the mouth of their beautiful gift horse.  Other people may be much cooler about the question, understanding that small companies are risky and you're being methodical.  And in some smaller companies, they may believe giving you the expenses could make office life awkward. If you approach it professionally, directly, and briefly (do not over-explain yourself) with the responsible accountant or HR person (if any), then I imagine it should not be a problem for them to give some information.  Conversely, you may feel comfortable enough to review a high-level summary sheet with a founder, or to find some other way of tactfully reviewing the right information. In any case, I would keep the request vague, simple, and direct, and see what information they show you.  If your request is too specific, then you risk pushing them to show information A, which they refuse to do, but a vague request would've prompted them to show you information B.  A too-specific request might get you information X when a vague request could have garnered XYZ.  Vague requests are also less aggressive and may raise fewer objections. The third question is difficult to say.  My personal understanding is some perspective of how venture capitalists look at the investment opportunity (you didn't say how new this startup is or what series/stage they are on, so I'll try to stay vague). The actual financials are less relevant for startups than they are for other investments because the situation will definitely change.  Most venture capital firms like to look at the burn rate or amount of cash spent, usually at a monthly rate.  A high burn rate relative to infusions of cash suggests the company is growing rapidly but may have a risk of toppling (i.e. failing before exit).  Burn rate can change drastically during the early life of the startup.  Of course burn rate needs the context of revenues and reserves (and latest valuation is helpful as a benchmark, but you may be able to calculate that from the restricted share offer made to you).  High burn rate might not be bad, if the company is booming along towards a successful exit. You might also want to look at some sort of business plan or info sheet, rather than financials alone.  You want to gauge the size of the market (most startups like to claim 9- or 10-figure markets, so even a few percentage points of market share will hit revenue into the 8-figures).  You'll also have to have a sense for the business plan and model and whether it's a good investment or a ridiculous rehash (""it's Twitter for dogs meets Match.com for Russian Orthodox singles!"").  In other words, appraise it like an investor or VC and figure out whether it's a prospect for decent return.  Typical things like competition, customer acquisition costs, manufacturing costs are relevant depending on the type of business activity. Of course, I wouldn't ignore psychology (note that economists and finance people don't generally condone the following sort of emotional thinking).  If you don't invest in the company and it goes big, you'll kick yourself.  If it goes really big, other people will either assume you are rich or feel sad for you if you say you didn't get rich.  If you invest but lose money, it may not be so painful as not investing and losing out the opportunity.  So if you consider the emotional aspect of personal finance, it may be wise to invest at least a little, and hedge against ""woulda-shoulda"" syndrome.  That's more like emotional advice than hard-nosed financial advice. So much of the answer really depends on your particular circumstances.  Obviously you have other considerations like whether you can afford the investment, which will be on you to decide.  And of course, the § 83(b) election is almost always recommended in these situations (which seems to be what you are saying) to convert ordinary income into capital gain.  You may also need cash to pay any up-front taxes on the § 83(b) equity, depending on your circumstances." The main things to ask about are going to revolve around the best way to structure your business. Know what your plans are for partnership. Know whether or not you'll need a lot of up front capital, and if you'll be subjected to an abnormal amount of risk in the course of day to day operations. If you'll be working with one or more partners, ask for help with an operating agreement. You'll find out whether or not you need an accountant throughout these discussions.   Edit: Going through those points will enable your lawyer to help you file under the appropriate structure. Ask for help with anything you're unsure about. Stuff I wish I had known, based on having done the following: Obtained employment at a startup that grants Incentive Stock Options (ISOs);  Early-exercised a portion of my options when fair market value was very close to my strike price to minimize AMT; made a section 83b) election and paid my AMT up front for that tax year. All this (the exercise and the AMT) was done out of pocket. I've never see EquityZen or Equidate mention anything about loans for your exercise. My understanding is they help you sell your shares once you actually own them. Stayed at said startup long enough to have my exercised portion of these ISOs vest and count as long term capital gains;  Tried to sell them on both EquityZen and Equidate with no success, due to not meeting their transaction minimums.  Initial contact with EquityZen was very friendly and helpful, and I even got a notice about a potential sale, but then they hired an intern to answer emails and I remember his responses being particularly dismissive, as if I was wasting their time by trying to sell such a small amount of stock. So that didn't go anywhere. Equidate was a little more friendly and was open to the option of pooling shares with other employees to make a sale in order to meet their minimum, but that never happened either.  My advice, if you're thinking about exercising and you're worried about liquidity on the secondary markets, would be to find out what the minimums would be for your specific company on these platforms before you plunk any cash down. Eventually brought my request for liquidity back to the company who helped connect me with an interested external buyer, and we completed the transaction that way. As for employer approval - there's really no reason or basis that your company wouldn't allow it (if you paid to exercise then the shares are yours to sell, though the company may have a right of first refusal). It's not really in the company's best interest to have their shares be illiquid on the secondary markets, since that sends a bad signal to potential investors and future employees. It basically only affects the company's dealings with its own stock, not with operational concerns.  If the company were to offer more stock for sale, it would get less cash.  If it had a stock buy-back program, it could buy more shares for the same money.  If it was to offer to acquire another company in exchange for its own stock, the terms would be less attractive to the other company's owners.  Employee stock remuneration, stock options, and so forth would be affected, so there might be considerations and tax consequences for the company. 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. There were several areas where the mortgage and car loan have affected your credit.  The mortgage had the following impacts, The car loan (purchased shortly after the house) had the following impacts, You did not mention your payment history, but since you had an 800 prior to the house purchase, we can assume that your payment history is current (nothing late). You did not mention your credit utilization, but you want to keep your utilization low (various experts suggest 10%, 20% and 30% as thresholds).  The down payment on the house likely drained your available funds, and replacing the car may have also put stress on your funds.  And when you buy a house, often there are additional expenses that further strain budgets. My guess is that your utilization percentage has increased.  My suggestion would be to reduce your utilization ratio on your revolving accounts.  And since you have plenty of credit lines, you might want to payoff the car. Your Chase card has a good age, which helps with age of credit, and though you will find experts that say you should only have 2-4 revolving accounts (credit cards), other experience shows that having accounts with age on them is a good thing.  And having a larger number of accounts does not cause problems (unless you have higher utilization or you miss payments). You did not mention whether the Chase card has any fees or expenses, as that would be a reason to either negotiate with Chase to reduce or eliminate the fees, or to cancel the card. Have you checked your credit report for errors?  You can get a free report from each of the three bureaus once per year.