Can compensation income from an employee stock purchase plan be negative?
The sentence you quoted does not apply in the case where you sell the stock at a loss. In that case, you recognize zero ordinary income, and a capital loss (opposite of a gain) for the loss. Reference: http://efs.fidelity.com/support/sps/article/article2.html
"IANAL, but no, this is not sound legal advice. There are a few things that stick out to me as fishy. First off: you are calculating the 3% safe-harbor on the 2017 compensation limit of $270k, but limiting yourself to $53k in total contributions which is the 2016 limit. It's hard to tell what tax year you're working in here. If you're planning for 2017, fine, but if you're wrapping up 2016 then you need to use 2016 limits. Secondly (and this is something I think your counsel should know already): you don't take Employer contributions out of gross wages (box 1) on the W-2. They aren't even reported there in the first place! With your base scenario the 2 employees' W-2s would look like this: Employee A's W-2 Gross Wages (box 1) = 280,000 - 14,966.67 = 265,033.33 Employee B's W-2 Gross Wages (box 1) = 280,000 - 0 = 280,000 Elective deferrals are the only thing that should come out of wages. Not the SH 3% or Match. Thirdly: Retirement Plan expenses really aren't an ""above the line"" expense. They are not included in cost of goods sold. Even if you establish a ""pool"" for that expense, it's still not a direct cost attributable to the production of whatever your company sells. Also: Employee B should not have to contribute to the retirement account of Employee A! The only situation I can see where Employee A and B would be required to fund the match equally, were if Employee A & B are both 50% owners and the company has no funds of its own with which to fund the match. The company has obligated itself to fund the match, and if the company doesn't have any money then the money still has to come from somewhere (ie. the owners pony up more funds for the match they promised their employees, it just happens that the employees are also the owners). Even in this situation though, I still stand behind my first 3 points." There are some nuances with HCE definition. To answer your questions. It's compensation as defined by the plan. Usually it's gross comp, but it can exclude things like fringe benefits, overtime pay, commissions, bonuses, etc. The compensation test is also a look-back test, meaning that an EE is determined to be an HCE in the current year if their compensation in the previous year was over the limit. I'm not sure how stock options affect this, but I expect they would be counted. Probably have an ESOP plan at that point too which is a whole other can-o-woms. The 5% owner test applies to the current year and also has a one-year look-back period. If at ANY point, even for a day, an employee was more than 5% owner, they are HCE for that year and next. Yes there is a limit. A company may limit the amount of HCE's to the top 20% of employees by pay like Aganju said. They can also disregard employees that may otherwise have been excluded under the plan using statutory exclusions. Example, they can disregard employees under 21 years and with less than 1 year of service. Hahaha, the IRS does not like to concisely define things. You can look here, that's probably as concise as you'll get. Hope this helps! "I write software myself and was involved in a couple of start ups.  One failed, another was wildly successful, but I did not receive much in compensation. The former I received stock, but since it failed, it was worthless anyway.  There should be compensation for your time in addition to equity in a company.   Any agreement needs be in writing.  In the later situation I was told to expect about a 17%/year bonus, but nothing could be guaranteed.  Translation:  ""It will never happen.""  It didn't, but I meet my lovely wife there so I have that for a bonus. Agreements need to address the bad things can happen.  What happens if one of you is no longer interested in continuing?  What happens if one of you die, or addicted to something?  What happens if one of you gets thrown in jail or disabled?  Right now you are full of optimism and hope, but bad things happen.  Cover those things while you still like each other. It might be enough to have a good salary, and some stock options.  You man not be interested in running the day to day business. Most of all good luck, I wish you all the best!" I have worked for companies that have done this. One did have a match and the other did not. When they figured their profit at the end of the year a portion was given to the employees as a 401K deposit.  retirement-topics-401k-and-profit-sharing-plan-contribution-limits Total annual contributions (annual additions) to all of your accounts   in plans maintained by one employer (and any related employer) are   limited. The limit applies to the total of: elective deferrals employer matching contributions employer nonelective contributions allocations of forfeitures The annual additions paid to a participant’s account cannot exceed the   lesser of: 100% of the participant's compensation, or $54,000 ($60,000 including catch-up contributions) for 2017;  $53,000   ($59,000 including catch-up contributions) for 2016. So as long as everything stays below that $54,000 limit you are good. In one case the decision was made by the company for the employee, the other company gave us the option of bonus check or 401K. I heard that most of the employees wanted the money in the 401K. The net gain isn't $0.  An employer prefers candidate A over candidate B because he thinks A is worth more.  To give the employer adequate incentive to go with B over A, the incentive would have to be worth about as much as A's margin over the expected duration of A's employment.  That's probably not just like $5k. It's legal. In fact, they are required to do this, assuming you are in fact a HCE (highly compensated employee) to avoid getting in trouble with the IRS. I'm guessing they don't provide documentation for the same reason they don't explain to you explicitly what the income thresholds are for social security taxes, etc - that's a job for your personal accountant. Here's the definition of a HCE:  An individual who: Owned more than 5% of the interest in the business at any time during   the year or the preceding year, regardless of how much compensation   that person earned or received, or For the preceding year, received   compensation from the business of more than $115,000 (if the preceding   year is 2014; $120,000 if the preceding year is 2015, 2016 or 2017),   and, if the employer so chooses, was in the top 20% of employees when   ranked by compensation. There are rules the restrict distributions from plans like 401ks. For example, treasury reg 1.401a(4)-5(b)(3) says that a plan cannot make a distribution to a HCE if that payment reduces the asset value of the plan to below 110% of the value of the plan's current liabilities. So, after taking account all distributions to be made to HCEs and the asset value of the plan, everyone likely gets proportionally reduced so that they don't run afoul of this rule. There are workarounds for this. But, these are options that the plan administrators may take, not you. I suppose if you were still employed there and at a high enough level, a company accountant would have discussed these options with you. Note, there's a chance there's some other limitation on HCEs that I'm missing which applies to your specific situation. Your best bet, to understand, is simply ask. Your money is still there, you just can't get it all this year. I just had a reverse split done 1 to 35. I went from 110,000 shares and a negative 13k to 3172 shares, and I still had a negative 13k. If your company does a reverse split take the lost and get out, it's bad news all the way around. You're talking about NQO - non-qualified stock options. Even assuming the whole scheme is going to work, the way NQO are taxed is that the difference between the fair market value and the strike price is considered income to you and is taxed as salary. You'll save nothing, and will add a huge headache and additional costs of IPO and SEC regulations. As I recall, the gain for ISOs is considered ordinary income, and capital losses can only negate up to $3000 of this each year.  If you exercised and held the stock, you have ordinary income to the exercise price, and cap gain above that, if you hold the stock for two years.  EDIT - as noted below, this answer works for USians who found this question, but not for the OP who is Canadian, or at least asked a question at it relates to Canada's tax code. Your gain is $1408. The difference between 32% of your gain and 15% of your gain is $236.36 or $1.60 per share. If you sell now, you have $3957.44 after taxes.  Forget about the ESPP for a moment. Are you be willing to wager $4000 on the proposition that your company's stock price won't go down more than $1.60 or so over the next 18 months? I've never felt it was worth it. Also, I never thought it made much sense to own any of my employer's stock. If their business does poorly, I'd prefer not to have both my job and my money at risk. If you sell now: Now assuming you hold for 18 months, pay 15% capital gains tax, and the stock price drops by $1.60 to $23.40: 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. What most respondents are forgetting, is when a company allows its employees to purchase its shares at a discount with their salary, the employee is usually required to hold the stock for a number of years before they can sell them. The reason the company is allowing or promoting its employees to purchase its shares at a discount is to give the employees a sense of ownership of the company. Being a part owner in the company, the employee will want the company to succeed and will tend to be more productive. If employees were allowed to purchase the shares at a discount and sell them straight away, it would defeat this purpose. Your best option to decide whether or not to buy the shares is to work out if the investment is a good one as per any other investment you would undertake, i.e. determine how the company is currently performing and what its future prospects are likely to be. Regarding what percentage of pay to purchase the shares with, if you do decide to buy them, you need to work that out based on your current and future budgetary needs and your savings plan for the future. 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. It's not a 60% raise. He made 60% more than the previous year. There's lots of things that could account for that. One of them is an annual bonus that was larger than his previous annual bonus - the calculation of that bonus was likely negotiated as part of his contract.  A large chunk of the gains seems to be between that and stock/option awards. Often stock/option vest differently in the first year than remaining years, and the value changes over time as the stock market moves. If you have options granted with a strike price set based on the closing price of stock the day you start, and you cash them out as you get them, after a year if it's gone up 5% you make a bit. After the second year if it's gone up 10%, you doubled your income from that source even though you didn't receive any more options that year.  His salary raise doesn't seem out of line. I've gotten larger raises in my career.  Now... suppose all of his compensation was spread out evenly across all of the employees. CAT has a bit over 100K employees. His total compensation was $16M 16M / 100K = $160. You could give every employee $160/yr more for the cost of the CEO's entire compensation package. That comes out at 7-8 cents/hour. If you only do it with his raise and not the one time bonuses and returns from stock/option grants well... $3/employee/yr.  The best way to invest in people is to offer training to help them move to higher value jobs. Things like tuition reimbursement programs based on maintaining good performance in classes are solid benefits to offer. Or even job training to those who show aptitude for different classes of work. Maybe some merit based bonus structure - people who come up with good ideas for cutting costs, improving efficiency, etc and work to see them implemented qualify for some sort of bonus based on a percentage of the value of that change.  The bigger problem with those types of programs is that collective bargaining agreements tend to forbid any sort of merit based pay. They also make jumping line in seniority impossible - i.e. the union agreement would say that the person most qualified for the extra training is the one who's been in the job the longest. Some of these rules make sense if your goal is that everybody is equal and your idea of fairness is based on avoiding inequality. To justify it, they'll throw up things like the boss's cousin's brother-in-law's ex-wife's son could get preferential treatment if the contract doesn't prevent it. I'm guessing you're talking about options given to employees. The company can issue stock options at whatever strike price it wants. The difference between the strike price and the actual market value is considered income to the employee. You can get the options at $0 strike just as well (although companies generally just give RSUs instead in this case).