Evaluating worth of ESPP (Startup)
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.
Other than the guaranteed 5% bonus (assuming you sell it right away), no benefits. Keep in mind that the price from which the discount is calculated is not necessarily the market price at the date of the ESPP purchase, so the actual discount may be more than 5% (depending on the volatility of the stock - much more). "Unless you have a good handle on what niches the startups of yesteryear were entering I think it is hard to get a handle on why there is a decline.  Is this a decline in the number of restaurants being started or is this a decline in the number of internet startups.  The reasons will depend on the character of the startups.  One trend I think is pretty common is the decline of the local market.  The internet and free shipping makes the internet the growth area for specialized commerce.  So many commerce niches are threatened it would take a real optimist to consider a start-up in a niche that is essentially being the local distributor for something people can get more cheaply on-line.    Then there is the idea that,  ""local"" doesn't mean the same thing as it did  even 30 years ago as people drive further to get the essentials at big box stores.  A declining main street of a small town, or a declining mall in the suburbs isn't an attractive place to be an entrepreneur.  On the other hand competing in the big box strip on the edge of town has its own challenge:  people are shopping at 80km/hr and you need a huge storefront  and/or a huge advertising budget even to get noticed.    If the decline is in the number of restaurant startups,  it might be that this is related to a decline in middleclass disposable income.   If it is a decline in internet startups,  perhaps it is just showing a maturing of the industry from a fast growth phase where all sorts of unfilled niches were open for the quick entrepreneur to a more mature market where the internet is consolidating with a few behemoths taking up all the oxygen." Investing only in one industry may be problematic as it is highly correlated. There are factor outside your (or anyones) knowledge which may affect all the industry: If you are familiar with the industry it may happen that you work in that (ignore rest of paragraph if this is not the case). In such case you are likely to have problems at work (frozen salary, no bonus, position terminated) and you need to liquidate the investments at that point (see many advice regarding ESPP). Depending on your field you may have some inside knowledge so even if you would took a position without it you may need to somehow prove it. On the other hand diversifying the investment might reduce the volatility of investment. Rise in oil will cause problems for air industry but will be a boom for oil industry etc. In this way you smooth the grow of the investments. Investing part of portfolio into specific industry may make more sense. It still possibly worth to avoid it at the beginning investor may have trouble to beat the market (for example according to behavioural economics you are exposed to various biases, or if markets are efficient then prices most likely already take into account any information you may have). (I'm still new to all this so it's mostly based on what I read rather then any personal experience. Also a standard disclaimer that this is not an investment, or any other, advice and I'm not licensed financial advisor in any jurisdiction) Hopefully, before you invested in this stock, you evaluated the company.  You looked at the financial information about the company and where the company was headed, and evaluated whether the stock was undervalued or overvalued.  Hopefully, you determined that the stock was undervalued at the time you bought it. The thing to do now is to reevaluate the stock.  Do you think the stock is overvalued or undervalued right now?  If you didn't own it, would you buy it today?  Instead of looking at the past performance of the stock, you want to try to determine which direction the stock will go from today.  If you wouldn't buy it today at it's current price, then you should sell. If you have no idea how to do this evaluation, neither do I.  For me, with the investing knowledge I have right now, investing in an individual stock would be way too risky.  If you don't know how to evaluate a stock and determine if it is a good buy or not, then you should stay away from individual stocks and instead invest in stock mutual funds, which lower the risk by diversifying over lots of stocks. Aswath Damodaran's [Investment Valuation 3rd edition](http://www.amazon.com/Investment-Valuation-Techniques-Determining-University/dp/1118130731/ref=sr_1_12?ie=UTF8&amp;qid=1339995852&amp;sr=8-12&amp;keywords=aswath+damodaran) (or save money and go with a used copy of the [2nd edition](http://www.amazon.com/gp/offer-listing/0471414905/ref=dp_olp_used?ie=UTF8&amp;condition=used))  He's a professor at Stern School of Business. His [website](http://pages.stern.nyu.edu/~adamodar/) and [blog](http://aswathdamodaran.blogspot.com/) are good resources as well. [Here is his support page](http://pages.stern.nyu.edu/~adamodar/New_Home_Page/Inv3ed.htm) for his Investment Valuation text. It includes chapter summaries, slides, ect. If you're interested in buying the text you can get an idea of what's in it by checking that site out. To determine the value of one's life, instead of rating happiness from 1 to 10 every day in pink ink in a secret diary, use the concept of mercantile exchange to determine the value of your existence. First, offer your time for some initial price ($10) to some investors (Bob). Then, create an order book where anyone can make a bid or ask for your time. For example, Bob creates a sell order for 10 min of your time for $20. Mary creates a buy order for 10 min of your time for $20--Bob sells 10 min of your time to Mary for $20. Based on the supply and demand for your time, you could determine the value of your existence. Obviously, your time would no longer be yours, but it's interesting to consider nontheless and precisely equivalent to the process that determines stock price. (Ignoring the minutiae of order books and IPOs.) It's been awhile since my last finance course, so school me here:  What is the market cap of a company actually supposed to represent? I get that it's the stock price X the # of shares, but what is that actually representing? Revenues? PV of all future revenues? PV of future cash flows?  In any case, good write up. Valuation of tech stocks is quite the gambit, and you've done a good job of dissecting it for a layman. Yep, a lot of startup funding these days is called equity, which makes for nice valuation, but there are often so many extra stipulations (I've even read of caps on upside; wish I could find the Matt Levine column on it now) that it really is effectively debt.