Buying shares in employer's company during IPO
I think of these things in terms of risk.  Investing in individual stocks is risky, and investing in brand new individual stocks is riskier still. However, the payoff can be quite high.  The fact that you work at the company increases your exposure. If the company goes under, then not only have you lost your investment, but you've lost your job and income as well.  It really depends on how much of your total portfolio this investment represents. Consider the following: If you can say yes to all or most of these, then a small investment in your company is fine. If you end up losing your investment, you'll still be okay.  I think it can help a company when the employees have a little skin in the game. I hope it pays out big for you. Rather than take anyone's word for it (including and especially mine) you need to do think very carefully about your company; you know it far better than almost anyone else. Do you feel that the company values its employees? If it values you and your immediate colleagues then its likely that it not only values its other employees but also its customers which is a sign that it will do well. Does the company have a good relationship with its customers? Since you are a software engineer using a web stack I assume that it is either a web consultancy or has an e-commerce side to it so you will have some exposure to what the customers complain about, either in terms of bugs or UX difficulties. You probably even get bug reports that tell you what customer pain points are. Are customers' concerns valid, serious and damaging? If they are then you should think twice about taking up the offer, if not then you may well be fine. Also bear in mind how much profit is made on each item of product and how many you can possibly sell - you need to be able to sell items that have been produced. Those factors indicate how the future of the company looks currently, next you need to think about why the IPO is needed. IPOs and other share offerings are generally done to raise capital for the firm so is your company raising money to invest for the future or to cover losses and cashflow shortfalls? Are you being paid on time and without issues? Do you get all of the equipment and hiring positions that you want or is money always a limiting factor? As an insider you have a better chance to analyse these things than outsiders as they effect your day-to-day work. Remember that anything in the prospectus is just marketing spiel; expecting a 4.5 - 5.3% div yield is not the same as actually paying it or guaranteeing it. Do you think that they could afford to pay it? The company is trying to sell these shares for the maximum price they can get, don't fall for the hyped up sales pitch. If you feel that all of these factors are positive then you should buy as much as you can, hopefully far more than the minimum, as it seems like the company is a strong, growing concern. If you have any concerns from thinking about these factors then you probably shouldn't buy any (unless you are getting a discount but that's a different set of considerations) as your money would be better utilized elsewhere. So the key factor here, IMHO, is the amount we are talking about.  $2K is just not a lot of money.  If you lose every penny, you can recover.  On the other hand it is unlikely to make you wealthy.  So if I was you I would buy in, more for the fun of it all. Now if it was a large amount of money that we were talking about it would be about a percentage of my net worth.  For example, lets say the minimum was 20K, and you really believed in the company.  If I had a net worth of less than 200K, I would not do it.  If I had a larger net worth, I would consider it unless I was near retirement. So if I was 30, hand a net worth of 300K, I would probably invest as even if I did lose it all, I could recover.    Having said all that it does not sound like you completely agree that the company will be profitable.  So in that case, don't buy. Also, I have the opportunity to buy my own company's stock at a discount.  However, I do not for two reasons.  The first is I don't like investing in the company I work for.  Secondly, they require you to hold the stock for a year. its the best investment you can have specially with the company you work for and IPO, if i was you i would invest in more then just the minimum since its IPO. ask you your manager or supervisor how much are they buying the stocks for if they are doing it the go for it you'll be okay just keep track of it regular sometime you can invest more as time go by. You can get the idea by how much production your company is doing, if your company's profit going up chances are you need to buy more.
Summarized article: The NASDAQ announced it will offer $40 million to compensate clients who were disadvantaged by technical problems during Facebook's IPO on May 18.   NASDAQ's technical glitch caused a delay in the opening of first day trading of Facebook shares and traders experienced slow order confirmations.   NASDAQ said $13.7 million will be paid to its affected investment firms and the balance will be given to the firms as credit to reduce trading fees. The benefits would last as long as 6 months.   Investors who are eligible for compensation are those who placed orders to buy Facebook shares at $42 or less but were executed at an inferior price or those whose orders went through but were not immediately confirmed.  The New York Stock Exchange (NYSE) opposed the compensation offer saying the move would allow NASDAQ to undercut them on prices and would take market share from competing exchanges.   NASDAQ's compensation plan is subject to regulator approval.    Facebook shares are currently down 30% from the IPO price of $38.  *For more summarized news, subscribe to the [/r/SkimThat](http://www.reddit.com/r/SkimThat) subreddit* I agree with the other comments that you should not buy/hold your company stock even if given at a discount. If equity is provided as part of the compensation package (Options/Restrictive Stock Units RSU)then this rule does not apply. As a matter of diversification, you should not have majority equity stake of other companies in the same sector (e.g. technology) as your employer. Asset allocation and diversification if done in the right way, takes care of the returns. Buying and selling on the same day is generally not allowed for ESPP. Taxation headaches. This is from personal experience (Cisco Systems). I had options issued in Sept 2008 at 18$ 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. I see a false assumption that you are making.  (Almost always) When you buy stock the cash you spend does not go to the company. Instead it goes to someone else who is selling their shares.  The exception to this is when you buy shares in an IPO.  Those of us who have saved all our lives for retirement want income producing investments once we retire. (Hopefully) We have saved up quite a bit of money. To have us purchase their stock companies have to offer us dividends. "There are quite a few regulations on ""Insider Trading"". Blackouts are one of the means companies adopt to comply with ""Insider Trading"" regulations, mandating employees to refrain from selling/buying during the notified period. Once you leave the employment: So unless there is an urgent need for you to sell/buy the options, wait for some time and then indulge in trade." "I'm not the OP, but I'm happy to give a brief overview.  Basically, pre-JOBS act there were a lot of limits on who could make an equity investment in a non-public company (i.e. a startup or even a hedge fund). There were some loopholes, but basically you had to be an 'accredited investor'. An accredited investor was someone who either has made $200,000+ ($300,000+ for married people) for the past two years and expects to make that much again in the current year. Alternately, they could have a net worth of $1 million, excluding the value of their primary residence. There was also a limit of 500 investors for a non-public company before the company had to become public (they didn't really have to IPO, but they did have to file their financials with the SEC, so the effect was basically the same). Finally, non-public companies were prohibited from seeking investment through advertising basically. They couldn't take out an ad in a paper or event send a mass email and say, ""Hey, we're looking to raise a $1 million funding round, contact us if you're interested!""  Okay, now after the JOBS Act.  The JOBS Act changed a) the number and type of investors who could make equity investments in a non-public company b) the regulation of advertising for investments.  Post-JOBS private companies could have 2,000 shareholders and 500 of those could be unaccredited (e.g. regular people like you and I). The change in the number of shareholders isn't really that important because it's just shareholders of record, but that's another post for another day. There are still some requirements for unaccredited shareholder, which I don't remember off the top of my head. I think you have to have income of at least $40k. They also changed the solicitation ban, so it's possible that you might see an ad in the WSJ someday for a startup company, venture capital fund, hedge fund, etc.  There are some other things it changed, but IMO those are the two most important." "To expand on the above, go to the ""Investor Relations"" part of the website if they're public, and take a look at how they explain themselves to their shareholders. You'll learn a lot very quickly about everything you'd need for the interview." You also need to remember that stock options usually become valueless if not exercised while an employee of the company.  So if there is any chance that you will leave the company before an IPO, the effective value of the stock options is zero.  That is the safest and least risky valuation of the stock options.   With a Google or Facebook, stock options can be exercised and immediately sold, as they are publicly traded.  In fact, they may give stock grants where you sell part of the grant to pay tax withholding.  You can then sell the remainder of the grant for money at any time, even after you leave the company.  You only need the option/grant to vest to take advantage of it.  Valuing these at face value (current stock price) makes sense.  That's at least a reasonable guess of future value.   If you are absolutely sure that you will stay with the company until the IPO, then valuing the stock based on earnings can make sense.  A ten million dollar profit can justify a hundred million dollar IPO market capitalization easily.  Divide that by the number of shares outstanding and multiply by how many you get.  If anything, that gives you a conservative estimate.   I would still favor the big company offers though.  As I said, they are immediately tradeable while this offer is effectively contingent on the IPO.  If you leave before then, you get nothing.  If they delay the IPO, you're stuck.  You can't leave the company until then without sacrificing that portion of your compensation.  That seems a big commitment to make. 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.