How can I get the most value from my employer's ESPP?
A 15% discount is a 17.6% return. (100/85 = 1.176). For a holding period that's an average 15.5 days, a half month. It would be silly to compound this over a year as the numbers are limited.  The safest way to do this is to sell the day you are permitted. In effect, you are betting, 12 times a year, that the stock won't drop 15% in 3 days. You can pull data going back decades, or as long as your company has been public, and run a spreadsheet to see how many times, if at all, the stock has seen this kind of volatility over 3 day periods. Even for volatile stocks, a 15% move is pretty large, you're likely to find your stock doing this less than once per year. It's also safest to not accumulate too many shares of your company for multiple reasons, having to do with risk spreading, diversification, etc.  2 additional points -  the Brexit just caused the S&P to drop 4% over the last 3 days trading. This was a major world event, but, on average we are down 4%. One would have to be very unlucky to have their stock drop 15% over the specific 3 days we are discussing.  The dollars at risk are minimal. Say you make $120K/yr. $10K/month. 15% of this is $1500 and you are buying $1765 worth of stock. The gains, on average are expected to be $265/mo. Doesn't seem like too much, but it's $3180 over a years' time. $3180 in profit for a maximum $1500 at risk at any month's cycle. Short answer is to put the max 15% contribution into your ESPP. Long answer is that since you want to be saving as much as you can anyway, this is a great way to force you to do it, and pick up at least a 15% return every six months (or however often your plan makes a purchase). I say at least because sometimes an ESPP will give you the lower of the beginning or end period stock price, and then a 15% discount off of that (but check the details of your plan). If you feel like your company's stock is a good long term investment, then hold onto the shares when purchased. Otherwise sell as soon as you get them, and bank that 15% return. A 15% discount does not necessarily mean it is a good investment.  The stock price can go down at any point. 15% discount might mean you are getting a little better deal than the average cat.
Great questions -- the fact that you're thinking about it is what's most important. I think a priority should be maximizing any employer match in your 401(k) because it's free money. Second would be paying off high interest debt because it's a big expense. Everything else is a matter of setting good financial habits so I think the order of importance will vary from person to person. (That's why I ordered the priorities the way I did: employer matching is the easiest way to get more income with no additional work, and paying down high-interest debt is the best way to lower your long-term expenses.) After that, continue to maximize your income and savings, and be frugal with your expenses. Avoid debt. Take a vacation once in a while, too! There are two things to consider: taxes - beneficial treatment for long-term holding, and for ESPP's you can get lower taxes on higher earnings. Also, depending on local laws, some share schemes allow one to avoid some or all on the income tax. For example, in the UK £2000 in shares is treated differently to 2000 in cash vesting - restricted stocks or options can only be sold/exercised years after being granted, as long as the employee keeps his part of the contract (usually - staying at the same place of works through the vesting period). This means job retention for the employees, that's why they don't really care if you exercise the same day or not, they care that you actually keep working until the day when you can exercise arrives. By then you'll get more grants you'll want to wait to vest, and so on. This would keep you at the same place of work for a long time because by quitting you'd be forfeiting the grants. This is not right. Inferring the employee stock pool’s takeaway is not as easy as just taking a fraction of the purchase price. As an example, that wouldn’t account for any preferred returns of other ownership classes, among other things.   All considered though, it’s reasonable to assume that the employee stock pool will get some premium. Best of luck. ESPP shares, once purchased, are just normal shares that you got at a discount. They're just as much a part of your current net wealth as any other shares of stock. What you can't do is claim that discount increases your salary, even if it does result in your effectively taking home more money. It's a benefit like the company contribution to your health plan, not a bonus. This will be difficult to achieve.  It can be done, but it's very rare to have an agreement where your employer is willing to max out your contribution limit unless you are a partner in the business or a family relation. In this situation the extra employer money would probably come from a profit sharing contribution. If your employer increases your match, others are correct that your employer would have to increase the match for everyone. Not so with a profit sharing contribution. This is assuming 2 things though: Both of those are BIG if's, and I'd say 99% of the time it's not gonna happen for either of those two reasons. Your chances are better if you don't own >5% of the company, don't make over $120,000/year, and are related to you employer. Good luck! You didn't give enough information.  What is your goal?  What is your financial situation?   A discount to buy company stock can seem very tempting.  I was tempted by it myself, gee, almost 20 years ago.  I still own some of the stock.  But I held mutual funds first. There are two disadvantages that have disuaded me from partaking in the ESPP of my subsequent employers (one of which was a spin-out company of the stock-issuing company, the other having bought the spin-out).  First, putting a bunch of money in a single stock is rather risky.  single stocks will drop dramatically due to market conditions.  Generally market conditions don't act so dramatically on all stock.  Second, is it wise to put not only your salary but also your saved wealth all in one basket? It worked out reasonably well for me.  The stock doubled right before my division was spun out -- I sold half of my position.    And the resulting stock has continued to provide opportunities to diversify.  However, it could have just as easily dropped in half instead of doubled. What is your timeline for holding the stock -- for realizing any gain?  Can you afford patience if the stock value should drop in half? I have co-workers who continue to invest through our new company's ESPP.  At least one co-worker has the stated goal to sell after every purchase -- he holds the stock long enough to make a long-term gain instead of short term, but he sells after every purchase.  And it seems to him that the stock always drops right when he wants to sell. "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." I did this for the last tax year so hopefully I can help you. You should get a 1099-B (around the same time you're getting your W-2(s)) from the trustee (whichever company facilitates the ESPP) that has all the information you need to file. You'll fill out a Schedule D and (probably) a Form 8949 to describe the capital gains and/or losses from your sale(s). It's no different than if you had bought and sold stock with any brokerage. "I'm in the US, so there may be idiosyncrasies with UK taxes that I'm not familiar with, but here's how I've always treated stock I get as compensation.   Suppose the vested shares are worth X.  If I had X in cash, would I buy my company's stock as an investment?  Usually the answer is no, not because I think the stock will tank, but because there's better things I can do with that cash (pay off debt, unfortunately).  Therefore I sell the shares and use the cash for something else. You have stock options. So suppose the stock value is X but you can buy it for Y.  You can either: Therefore, the math is the same. If you had X in cash, would you buy your company's stock as an investment?  If so, then option 2 is best, because you can get X in stock for a lower cost. (Option 3 might be better if the gain on the stock will be taxed higher, but they're pretty much equivalent if there's no chance that the stock will drop below Y) If not, then option 4 is best since you will likely get more than X-Y from selling the options that by exercising them and selling the stock (since options have time value). If option 4 is not a possibility, then option 1 is best - you pocket X-Y as ""income"" and invest it however you see fit." Usually the amount of the ESPP stocks is very small compared to the overall volume of the trading, so it shouldn't matter. But check if for your company it not so (look at the stock history for the previous ESPP dates, and volumes). Here's the best explanation I found relating to why your T4 box 39 might not have an amount filled in, even when box 38 has one: Department of Finance – Explanatory Notes Relating to the Income Tax Act [...]. It's a long document, but here's the part I believe relevant, with my emphasis: Employee Stock Options ITA 110(1)   [...]   Paragraph 110(1)(d) is amended to include a requirement that the   employee [...] exercise the employee’s rights under the stock   option agreement and acquire the securities underlying the agreement   in order for the deduction in computing taxable income to be   available [...] ensures that   only one deduction is available in respect of an employment benefit. In other words, if employee stock option rights are surrendered to an   employer for cash or an in-kind payment, then (subject to new   subsections 110(1.1) and (1.2)) the employer may deduct the payment   but the employee cannot claim the stock option deduction. Conversely,   where an employer issues securities pursuant to an employee’s exercise   of stock options, the employer can not deduct an amount in respect of   the issuance, but the employee may be eligible to claim a deduction   under paragraph 110(1)(d). Did you receive real shares based on your participation in the ESPP, or did you get a cash payment for the net value of shares you would have been issued under the plan? From what I can tell, if you opted for a cash payment (or if your plan only allows for such), then the part I emphasized comes into play. Essentially, if conditions were such that your employer could claim a deduction on their corporate income tax return for the compensation paid to you as part of the plan, then you are not also able to claim a similar deduction on your personal income tax return. The money received in that manner is effectively taxed in your hands the same as any bonus employment income would be; i.e. it isn't afforded tax treatment equivalent to capital gains income. Your employer and/or ESPP administrator are best able to confirm the conditions which led to no amount in your box 39, but at least based on above you can see there are legitimate cases where box 38 would have an amount while box 39 doesn't. This is great, thank you. Can you think of any cases where expected return is greater than interest payments (like in #2) but the best choice would still be raise money through equity issuing? My intuition tells me this may be possible for an expensive company. 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. The typical deal is you can put 10% of your gross pay into the ESPP. The purchase will occur on the last deposit date, usually a 6 month period, at a 15% discount to the market price.  So, the math is something like this: Your return if sold the day it's purchased is not 15%, it's 100/85 or 17.6%. Minor nitpick on my part, I suppose.  Also the return is not a 6 month return, as the weekly or bi-weekly deductions are the average between the oldest (6 mo) and the most recent (uh, zero time, maybe a week.) This is closer to 3 months. The annualized rate is actually pretty meaningless since you don't have 4 opportunities to achieve this return, it's important only if the cash flow hit causes you to borrow to support the ESPP purchases. The risk is whether the stock drops the 15% before you can execute the sell to take advantage of the gain.  Of course the return is gross, you need to net for taxes.  Edit to respond to comment below - When I said meaningless, I meant that you can't take the 17.6%, annualize it to 91.2% per year and think your $1000 will compound to $1912. It's as meaningless as when an investor gets a 10% gain on a stock in one day, and (with 250 trading days per year) decides his $1000 will be worth $2 quadrillion dollars after a year. The 17.6% is significant in that it's available twice per year, for a true 38% return over a year, but if borrowing to help the cash flow, that rate is really over 3 months. Is it inevitably taxed by the government? Which government? Tax treatment of familial loans varies greatly be jurisdiction. What is proper documentation procedure? If you want to get paid back, definitely a lawyer ... each. Is it better to ask several family members to help contribute so each person loans less? Or is it taxed the same? If this is only a tax issue then see above. If it is a means of spreading risk then sure.