Get The Most Out Of Employee Stock Options.
An employee stock option plan can be a lucrative investment instrument if properly managed. For this reason, these plans have long served as a successful tool to attract top executives. In recent years, they've become a popular means to lure non-executive employees.
Unfortunately, some still fail to take full advantage of the money generated by their employee stock. Understanding the nature of stock options, taxation and the impact on personal income is key to maximizing such a potentially lucrative perk.
What's an Employee Stock Option?
An employee stock option is a contract issued by an employer to an employee to buy a set amount of shares of company stock at a fixed price for a limited period of time. There are two broad classifications of stock options issued: non-qualified stock options (NSO) and incentive stock options (ISO).
Non-qualified stock options differ from incentive stock options in two ways . First, NSOs are offered to non-executive employees and outside directors or consultants. By contrast, ISOs are strictly reserved for employees (more specifically, executives) of the company. Secondly, nonqualified options do not receive special federal tax treatment, while incentive stock options are given favorable tax treatment because they meet specific statutory rules described by the Internal Revenue Code (more on this favorable tax treatment is provided below).
NSO and ISO plans share a common trait: they can feel complex. Transactions within these plans must follow specific terms set forth by the employer agreement and the Internal Revenue Code.
Grant Date, Expiration, Vesting and Exercise.
To begin, employees are typically not granted full ownership of the options on the initiation date of the contract, also know as the grant date. They must comply with a specific schedule known as the vesting schedule when exercising their options. The vesting schedule begins on the day the options are granted and lists the dates that an employee is able to exercise a specific number of shares.
For example, an employer may grant 1,000 shares on the grant date, but a year from that date, 200 shares will vest, which means the employee is given the right to exercise 200 of the 1,000 shares initially granted. The year after, another 200 shares are vested, and so on. The vesting schedule is followed by an expiration date. On this date, the employer no longer reserves the right for its employee to purchase company stock under the terms of the agreement.
An employee stock option is granted at a specific price, known as the exercise price. It is the price per share that an employee must pay to exercise his or her options. The exercise price is important because it is used to determine the gain, also called the bargain element, and the tax payable on the contract. The bargain element is calculated by subtracting the exercise price from the market price of the company stock on the date the option is exercised.
Taxing Employee Stock Options.
The Internal Revenue Code also has a set of rules that an owner must obey to avoid paying hefty taxes on his or her contracts. The taxation of stock option contracts depends on the type of option owned.
For non-qualified stock options (NSO):
The grant is not a taxable event. Taxation begins at the time of exercise. The bargain element of a non-qualified stock option is considered "compensation" and is taxed at ordinary income tax rates. For example, if an employee is granted 100 shares of Stock A at an exercise price of $25, the market value of the stock at the time of exercise is $50. The bargain element on the contract is ($50 to $25) x 100 = $2,500. Note that we are assuming that these shares are 100 percent vested. The sale of the security triggers another taxable event. If the employee decides to sell the shares immediately (or less than a year from exercise), the transaction will be reported as a short-term capital gain (or loss) and will be subject to tax at ordinary income tax rates. If the employee decides to sell the shares a year after the exercise, the sale will be reported as a long-term capital gain (or loss) and the tax will be reduced.
Incentive stock options (ISO) receive special tax treatment:
The grant is not a taxable transaction. No taxable events are reported at exercise. However, the bargain element of an incentive stock option may trigger alternative minimum tax (AMT). The first taxable event occurs at the sale. If the shares are sold immediately after they are exercised, the bargain element is treated as ordinary income. The gain on the contract will be treated as a long-term capital gain if the following rule is honored: the stocks have to be held for 12 months after exercise and should not be sold until two years after the grant date. For example, suppose that Stock A is granted on January 1, 2007 (100% vested). The executive exercises the options on June 1, 2008. Should he or she wish to report the gain on the contract as a long-term capital gain, the stock cannot be sold before June 1, 2009.
Other Considerations.
Although the timing of a stock option strategy is important, there are other considerations to be made. Another key aspect of stock option planning is the effect that these instruments will have on overall asset allocation. For any investment plan to be successful, the assets have to be properly diversified.
An employee should be wary of concentrated positions on any company's stock. Most financial advisors suggest that company stock should represent 20 percent (at most) of the overall investment plan. While you may feel comfortable investing a larger percentage of your portfolio in your own company, it's simply safer to diversify. Consult a financial and/or tax specialist to determine the best execution plan for your portfolio.
Bottom Line.
Conceptually, options are an attractive payment method. What better way to encourage employees to participate in the growth of a company than by offering them to share in the profits? In practice, however, redemption and taxation of these instruments can be quite complicated. Most employees do not understand the tax effects of owning and exercising their options.
As a result, they can be heavily penalized by Uncle Sam and often miss out on some of the money generated by these contracts. Remember that selling your employee stock immediately after exercise will induce the higher short-term capital gains tax. Waiting until the sale qualifies for the lesser long-term capital gains tax can save you hundreds, or even thousands.

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How To Understand Employee Stock Options and Maximize Financial Gain.
By Amber Spencer | August 28, 2015.
Stock Options are a popular way for companies, especially startups, to compensate their employees. Although there is no guarantee of the success of a company, by fully understanding your stock options and specifically, the tax implications associated with them, you can avoid making common (and big) mistakes that can cost you thousands of dollars.
The most important things to understand are covered in this post: what they are, how they work and any tax implications you may come across.
Because reading your stock option agreement can be quite tedious and difficult to digest, here are the key things you need to understand before delving into the details:
What are stock options?
Stock options are given to you by your employer and they allow you to purchase a specified number of shares of the company at a fixed price (exercise price ) during a fixed timeframe. With stock options, you will hold no shareholder rights, such as receiving dividends or voting. A contract sets out the terms, which include number of shares, vesting schedule, exercise price, and expiry date.
They are usually issued as an incentive for you to work hard to improve the company’s performance and in turn, the stock value. The higher the company value, the higher the stock price and therefore the larger the potential for personal financial gain.
One of the biggest caveats about stock options are the tax implications when it comes to exercising them, which we discuss in some detail below.
How stock options work.
Firstly, it’s important to note that any value in the stock options is completely theoretica l until you pay the exercise price to buy the shares.
There will usually be a minimum length of time you must work at the company before you can exercise your options, known as the vesting period .
Once this period has passed and you have exercised your options, you will own the shares just as you would if you had bought them like any other investor.
Types of Stock Options.
There are different types of options you may be offered, so check your agreement to figure out which one yours fall under.
Stock option plan: You are given the option to purchase shares of the company at a predetermined price.
Employee stock purchase plan (ESPP): You can acquire shares at a discounted price that is less than the market price at the time of acquisition. Most ESPPs require you to work for the company for a certain amount of time before you can acquire the shares.
Stock bonus plan: You receive company shares free of charge.
Exercise Price.
If you have been issued options under a stock option plan (which is the most common of the above types) and the market value of the stock increases, you will still only pay the price per share noted in your stock option agreement.
This price is known as your exercise price.
For example, if you were granted 1,000 stock options at $10 per share when you started, even if the stock price has risen to $50, you will still only pay $10,000 (1,000 shares at $10 each) vs. their market value of $50,000.
In this case, you would receive a financial gain of $40,000 (subject to tax implications, discussed below).
How is the price I receive determined?
For private company options, the exercise price is often based on the price of shares at the company’s most recent funding round. If it is a public company, then usually the strike price is equal to the stock’s market value at the time the option is granted (but not always).
Underwater Stock Options.
Of course, if you’re working within a startup, there is often no guarantee that the company will succeed.
Sometimes employee stock options might have no value. This happens when your exercise price is higher than the current market price of the shares. When this happens, your stock options are said to be “underwater”.
During times of stock market volatility, employees of publicly traded companies may be allowed to exchange underwater options for those that are in money – since the company is legally allowed to cancel the first option grant and issue new options exercisable at the new share price.
Vesting Period.
Your company will determine what type of vesting period you have. By knowing how the vesting period works, you will be able to figure out exactly how long you need to wait before you can exercise your options.
These are the three ways your options could potentially vest:
1. Time-Based Vesting:
95% of companies that offer stock options use this type of vesting period. In this case, your options typically vest upon completion of a specified time period – usually 3 to 5 years. To add to the complexity, there are also two ways they may vest: all at once ( Cliff Vesting ), or in parts over a few years ( Graded Vesting ).
Cliff Vesting: When the option grant vests all at once, i. e. you have to wait the full length of your vesting period before you are able to exercise any of your stock options.
Yearly Graded Vesting: When the options grant vests in a series of parts over time i. e. you may get 25% in your first each year over a period of 4 years until the specified timeframe is up.
One Year Cliff & Monthly Graded Vesting: When the options vest at 25% at the end of the first year and the remaining 75% vest monthly (or quarterly) over the next three or four years. This is typically seen in early stage startups. So if you have a monthly vest with a one year cliff and you leave the company after 18 months, you’ll have vested 37.5% of your stock.
Example of Yearly Graded Vesting:
2. Performance-Based Vesting:
Options vest upon the achievement of a performance condition such as a financial metric or a specific share price.
3. Time-Accelerated Vesting:
A combination of time-based and performance-based vesting periods. With this method, your options are time-based, but if a predetermined market condition is achieved prior to the time-based requirement then this is accelerated.
Expiry Date.
Stock options always have an expiry date. The most common period is 10 years from the date of grant.
So, if you have a 4 year vesting period and the expiry period is 10 years, then you will have 6 years left to exercise your options after your vesting period.
Make sure you exercise your options before the expiration of the grant term. If you do not, you will permanently forfeit them.
Tax Implications.
Understanding the tax implications of owning and exercising your options is essential to ensuring that you keep as much of the money generated by your options as possible.
There are two pieces of taxation to consider when exercising stock options.
1. When you exercise the options.
The difference in the exercise price and the fair market value (FMV) on the date the options are exercised is taxed as employment income.
For example, if you had 10,000 options with an exercise price of $1.00 and the FMV of the shares on the exercise date was $3.00, the taxable benefit would be $20,000. In most cases, you can claim a deduction equal to 50% of the taxable benefit.
2. After you exercise the options and hold the shares.
Any gains or losses are treated no differently than if you purchased the shares on the open market. The FMV of the shares on the exercise date becomes the cost base for your shares.
Continuing with the example above, if the current share price is $7.00 and your cost base is $3.00, you have a capital gain of $4.00 per share. On your 10,000 shares, your total gain is $40,000. In Canada, you pay tax on half of that gain, which would be $20,000.
For Private Companies.
If your company is a CCPC (Canadian-controlled private corporation), the taxable benefit you realize when exercising the options can be deferred until you sell the shares if you hold the shares for at least 2 years before you sell them .
Unlike with public companies, the exercise price and the FMV on the grant date do not have to be equal.
Lifetime Capital Gains Exemption (LCGE)
CCPC shares are often eligible for a lifetime capital gains exemption (LCGE), meaning you pay no tax on any gains up to that amount. In order to qualify for this exemption, the company must be a CCPC when you sell the shares. If your company is going public, make sure you file the appropriate form (T2101) with CRA to make a deemed disposition of some or all of your shares as of that date. You don’t actually sell the shares, you are just recording the gain for tax purposes to take advantage of the exemption.
The LCGE for 2015 is $813,600, so you don’t want to miss out on that if you are fortunate enough to have a gain that big.
For Public Companies.
Make sure that the exercise price on your options was equal to the FMV on the grant date. If it is not, then your shares are not eligible for the 50% deduction. Unlike for CCPCs, the taxable benefit cannot be deferred, it is taxable in the year the options are exercised. Also, the LCGE does not apply to public company shares.
Common Questions.
What if you leave before the vesting period is up?
At the time you leave the company, you’ll want to understand how your departure affects the exercisability of your options to minimise any loss to you.
If you leave before the vesting date, you will either have to forfeit your options, or will have a short time period (typically 60 – 90 days) to exercise.
In other cases, when major job or life events occur such as disability or retirement, certain rules may be triggered under the plan.
What happens if the company is bought or goes public?
With an IPO, nothing changes with regards to your actual stock options (vested or unvested) other than the shares you can buy with them are now easier to sell. Sometimes there will be what is called a ‘lock-up’ period, meaning you have to wait 6 – 12 months after the IPO before you can sell your shares.
If the company is bought, your stock options will likely carry forward – exactly how they do so will be determined by the transaction on a case-by-case basis. In most scenarios, your options should be treated similarly to common shares.
Refer to the tax section above to review the tax implications of private companies going public companies.
What if you want to exercise on departure and the company is still private?
Usually if the company is still private, it is difficult to determine the fair market value of any shares to be received on exercise of an option. The value will be a best guess based on the last round of investment, or a valuation agent will determine the value of the company.
Any sale in this situation may be subject to a right of first refusal. This means your company or any one or more of its shareholders have the right to purchase the the shares at the price that was offered to you – or in some cases, a different price.
So, if you do decide to exercise your option upon leaving the company, you should first understand what rights, if any, the employer has to “recapture” your shares and on what terms.
How do you pay?
Stock plan rules for exercising will vary by company and there are three ways they can be exercised:
Make a cash payment – (Yes, you have to come up with the full cash amount.)
Pay through a salary deduction.
Sell immediately in a cashless exercise – You do not need to provide the cash to exercise the option upfront, but instead you can use the equity built up in the option. In other words, you can use the difference between the market value and the exercise price as a way to exercise the option.
Should you exercise right away?
Once your options have vested, try not to succumb to the desire for instant gratification and jump into exercising and selling your shares. In the long-run, it can be a mistake and your actions should be dictated by your stock option strategy.
An important consideration to make when you exercise your options is to think about the affect they will have on your overall asset allocation (if you currently have an investment portfolio).
For your investment planning to be successful, it is important for your assets to be appropriately diversified and therefore should be aware of any concentrated positions in the company’s stock. Many advisors recommend that no more than 10-15% of your net worth be in your company’s stock. If you are in a senior position with the company, a limit that low may not be practical. An experienced financial advisor can help you manage the risk of a concentrated stock position.
How are stock options different from RSUs?
RSUs (Restricted Stock Unit) are sometimes given instead of stock options. An RSU is valued in terms of the company’s stock, like a stock option. However it is unique in that it does not have an exercise price. This usually means that you do not own the RSUs until the vesting period (the same as the vesting period on stock options) has been met. At this time, they are assigned their current market value and are considered income. Since they’re considered income, a portion of the shares are withheld to pay income taxes. You then receive the remaining shares and can sell them whenever you like.
So, if you were granted 10,000 RSUs, you do not own these shares until the company hits a defined performance condition, such as an IPO. Once that defined period is hit, the company will deliver the 10,000 shares or cash equivalent of the number of shares.
Hopefully this article has helped you more thoroughly understand your stock option agreement. If you have any questions, don’t hesitate to reach out in the comments below!
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Amber is a content contributor at ModernAdvisor. When she's not writing about personal finance, saving money and investing, she's coding, hiking or training for her next fitness competition. Reach out to her at ambsvan.
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Thank you for this post! My employer has just announced that they will be offering a stock option plan to all employees and I was looking for information on this topic in advance of our information session next week. I definitely feel better equipped now.
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26 CFR 1.58-8 - Capital gains and stock options.
(a) In general. Section 58(g)(2) provides that the items of tax preference specified in section 57(a)(6), and § 1.57-1(b) (stock options), and section 57(a)(9), and § 1.57-1(i) (capital gains), which are attributable to sources within any foreign country or possession of the United States shall not be taken into account as items of tax preference if, under the tax laws of such country or possession, preferential treatment is not accorded:
(1) In the case of stock options, to the gain, profit, or other income realized from the transfer of shares of stock pursuant to the exercise of an option which is under United States tax law a qualified or restricted stock option (under section 422 or section 424); and.
(b) Source of capital gains and stock options. Generally, in determining whether the capital gain or stock option item of tax preference is attributable to sources within any foreign country or possession of the United States, the principles of sections 861-863 and the regulations thereunder are applied. Thus, the stock option item of tax preference, representing compensation for personal services, is attributable, in accordance with § 1.861-4, to sources within the country in which the personal services were performed. Where the capital gain item of tax preference represents gain from the purchase and sale of personal property, such gain is attributable, in accordance with § 1.861-7, entirely to sources within the country in which the property is sold. In accordance with paragraph (c) of § 1.861-7, in any case in which the sales transaction is arranged in a particular manner for the primary purpose of tax avoidance, all factors of the transaction, such as negotiations, the execution of the agreement, the location of the property, and the place of payment, will be considered, and the sale will be treated as having been consummated at the place where the substance of the sale occurred.
(c) Preferential treatment. For purposes of this section, gain, profit, or other income is accorded preferential treatment by a foreign country or possession of the United States if (1) recognition of the income, for foreign tax purposes, is deferred beyond the taxpayer's taxable year or comparable period for foreign tax purposes which coincides with the taxpayer's U. S. taxable year in cases where other items of profit, gain, or other income may not be deferred; (2) it is subject to tax at a lower effective rate (including no rate of tax) than other items of profit, gain, or other income, by means of a special rate of tax, artifical deductions, exemptions, exclusions, or similar reductions in the amount subject to tax; (3) it is subject to no significant amount of tax; or (4) the laws of the foreign country or possession by any other method provide tax treatment for such profit, gain, or other income more beneficial than the tax treatment otherwise accorded income by such country or possession. For the purpose of the preceding sentence, gain, profit, or other income is subject to no significant amount of tax if the amount of taxes imposed by the foreign country or possession of the United States is equal to less than 2.5 percent of the gross amount of such income.
(d) Examples. The principles of this section may be illustrated by the following examples:
This is a list of United States Code sections, Statutes at Large, Public Laws, and Presidential Documents, which provide rulemaking authority for this CFR Part.
It is not guaranteed to be accurate or up-to-date, though we do refresh the database weekly. More limitations on accuracy are described at the GPO site.
United States Code.
Reorganization . 1978 Plan No. 4.
Title 26 published on 16-Jun-2017 03:58.
The following are ALL rules, proposed rules, and notices (chronologically) published in the Federal Register relating to 26 CFR Part 1 after this date.
2017-06-30; vol. 82 # 125 - Friday, June 30, 2017.
82 FR 29719 - Regulations Regarding Withholding of Tax on Certain U. S. Source Income Paid to Foreign Persons, Information Reporting and Backup Withholding on Payments Made to Certain U. S. Persons, and Portfolio Interest Treatment; Correction.
This document contains corrections to final and temporary regulations (TD 9808), which were published in the Federal Register on Friday, January 6, 2017 (82 FR 2046). These regulations are related to withholding of tax on certain U. S. source income paid to foreign persons, information reporting and backup withholding with respect to payments made to certain U. S. persons, and portfolio interest paid to nonresident alien individuals and foreign corporations.
This document contains a correction to final and temporary regulations (TD 9809) that were published in the Federal Register on Friday, January 6, 2017 (82 FR 2124). The final and temporary regulations under chapter 4 of Subtitle A (sections 1471 through 1474) of the Internal Revenue Code of 1986 (Code) relate to information reporting by foreign financial institutions (FFIs) with respect to U. S. accounts and withholding on certain payments to FFIs and other foreign entities.
This document contains corrections to final and temporary regulations (TD 9809) that were published in the Federal Register on Friday, January 6, 2017 (82 FR 2124). The final and temporary regulations under chapter 4 of the Subtitle A (sections 1471 through 1474) of the Internal Revenue Code of 1986 (Code) relate to information reporting by foreign financial institutions (FFIs) with respect to U. S. accounts and withholding on certain payments to FFIs and other foreign entities.
This document contains final regulations that allow the Commissioner of Internal Revenue to adopt a streamlined application process that eligible organizations may use to apply for recognition of tax-exempt status under section 501(c)(3) of the Internal Revenue Code (Code). The final regulations affect organizations seeking recognition of tax-exempt status under section 501(c)(3).
82 FR 8811 - Guidance Under Section 355(e) Regarding Predecessors, Successors, and Limitation on Gain Recognition; Guidance Under Section 355(f); Correction.
This document contains corrections to temporary regulations (TD 9805) that published in the Federal Register on Monday, December 19, 2016 (81 FR 91738). The temporary regulations provide guidance regarding the distribution by a distributing corporation of stock or securities of a controlled corporation without the recognition of income, gain, or loss.
82 FR 8144 - Dividend Equivalents From Sources Within the United States.
This document provides guidance to nonresident alien individuals and foreign corporations that hold certain financial products providing for payments that are contingent upon or determined by reference to U. S. source dividend payments. This document also provides guidance to withholding agents that are responsible for withholding U. S. tax with respect to a dividend equivalent, as well as certain other parties to section 871(m) transactions and their agents.
This document contains corrections to the final and temporary regulations (T. D. 9790) that were published in the Federal Register on Friday, October 21, 2016 (81 FR 72858). The regulations relate to the determination of whether an interest in a corporation is treated as stock or indebtedness for all purposes of the Internal Revenue Code.
This document contains corrections to the final and temporary regulations (T. D. 9790) that were published in the Federal Register on Friday, October 21, 2016 (81 FR 72858). The regulations relate to the determination of whether an interest in a corporation is treated as stock or indebtedness for all purposes of the Internal Revenue Code.
This document contains proposed regulations relating to certain financial products providing for payments that are contingent upon or determined by reference to U. S. source dividend payments.
This document contains final regulations under section 7704(d)(1)(E) of the Internal Revenue Code (Code) relating to the qualifying income exception for publicly traded partnerships to not be treated as corporations for Federal income tax purposes. Specifically, these regulations define the activities that generate qualifying income from exploration, development, mining or production, processing, refining, transportation, and marketing of minerals or natural resources. These regulations affect publicly traded partnerships and their partners.
82 FR 7753 - Disclosures of Return Information Reflected on Returns to Officers and Employees of the Department of Commerce for Certain Statistical Purposes and Related Activities; Correction.
This document contains corrections to a notice of proposed rulemaking by cross-reference to temporary regulation (REG-133353-16) that was published in the Federal Register on Friday, December 9, 2016. The proposed regulations authorize the disclosure of specified return information to the Census Bureau (Bureau) for purposes of structuring the censuses and national economic accounts and conducting related statistical activities authorized by title 13.
82 FR 6235 - Application of Modified Carryover Basis to General Basis Rules.
This document contains final regulations regarding the application of the modified carryover basis rules of section 1022 of the Internal Revenue Code (Code). Specifically, the final regulations modify provisions of the Treasury Regulations involving basis rules by including a reference to section 1022 where appropriate. The regulations will affect property transferred from certain decedents who died in 2010. The regulations reflect changes to the law made by the Economic Growth and Tax Relief Reconciliation Act of 2001 and the Tax Relief, Unemployment Insurance Reauthorization, and Job Creation Act of 2010.
In the Rules and Regulations section of this issue of the Federal Register, temporary regulations are being issued under sections 197, 704, 721(c), and 6038B of the Internal Revenue Code (Code) that address transfers of appreciated property by U. S. persons to partnerships with foreign partners related to the transferor. The temporary regulations affect U. S. partners in domestic or foreign partnerships. The text of the temporary regulations also serves as the text of these proposed regulations.
This document withdraws proposed regulations relating to the definition of an authorized placement agency for purposes of a dependency exemption for a child placed for adoption that were issued prior to the changes made to the law by the Working Families Tax Relief Act of 2004 (WFTRA). This document contains proposed regulations that reflect changes made by WFTRA and by the Fostering Connections to Success and Increasing Adoptions Act of 2008 (FCSIAA) relating to the dependency exemption. This document also contains proposed regulations that, to reflect current law, amend the regulations relating to the surviving spouse and head of household filing statuses, the tax tables for individuals, the child and dependent care credit, the earned income credit, the standard deduction, joint tax returns, and taxpayer identification numbers for children placed for adoption. These proposed regulations change the IRS's position regarding the category of taxpayers permitted to claim the childless earned income credit. In determining a taxpayer's eligibility to claim a dependency exemption, these proposed regulations change the IRS's position regarding the adjusted gross income of a taxpayer filing a joint return for purposes of the tiebreaker rules and the source of support of certain payments that originated as governmental payments. These regulations provide guidance to individuals who may claim certain child-related tax benefits.
This document contains temporary regulations that address transfers of appreciated property by United States persons (U. S. persons) to partnerships with foreign partners related to the transferor. The regulations override the rules providing for nonrecognition of gain on a contribution of property to a partnership in exchange for an interest in the partnership under section 721(a) of the Internal Revenue Code (Code) pursuant to section 721(c) unless the partnership adopts the remedial method and certain other requirements are satisfied. The document also contains regulations under sections 197, 704, and 6038B that apply to certain transfers described in section 721. The regulations affect U. S. partners in domestic or foreign partnerships. The text of the temporary regulations also serves as the text of the proposed regulations set forth in the notice of proposed rulemaking on this subject in the Proposed Rules section of this issue of the Federal Register . The final regulations revise and add cross-references to coordinate the application of the temporary regulations.
82 FR 5387 - Certain Transfers of Property to Regulated Investment Companies [RICs] and Real Estate Investment Trusts [REITs]
This document contains final regulations effecting the repeal of the General Utilities doctrine by the Tax Reform Act of 1986. The final regulations address the length of time during which a RIC or a REIT may be subject to corporate level tax on certain dispositions of property. The final regulations affect RICs and REITs.
This document contains final regulations that identify certain stock of a foreign corporation that is disregarded in calculating ownership of the foreign corporation for purposes of determining whether it is a surrogate foreign corporation. These regulations also provide guidance on the effect of transfers of stock of a foreign corporation after the foreign corporation has acquired substantially all of the properties of a domestic corporation or of a trade or business of a domestic partnership. These regulations affect certain domestic corporations and partnerships (and certain parties related thereto) and foreign corporations that acquire substantially all of the properties of such domestic corporations or of the trades or businesses of such domestic partnerships. The text of the temporary regulations also serves as the text of the proposed regulations set forth in the notice of proposed rulemaking on Rules Regarding Inversions and Related Transactions in the Proposed Rules section of this issue of the Federal Register .
This document withdraws portions of a notice of proposed rulemaking (REG-135734-14) published on April 8, 2016, in the Federal Register (81 FR 20588). The withdrawn portions relate to exceptions to general rules addressing certain transactions that are structured to avoid the purposes of section 7874 of the Internal Revenue Code (Code).
In the Rules and Regulations section of this issue of the Federal Register, the Department of the Treasury (Treasury Department) and the IRS are amending portions of temporary regulations that address certain transactions that are structured to avoid the purposes of section 7874 of the Internal Revenue Code (Code). The temporary regulations affect certain domestic corporations and domestic partnerships whose assets are directly or indirectly acquired by a foreign corporation and certain persons related to such domestic corporations and domestic partnerships. The text of the temporary regulations in the Rules and Regulations section of this issue of the Federal Register also serves as the text of these proposed regulations.
This document contains proposed amendments to the definitions of qualified matching contributions (QMACs) and qualified nonelective contributions (QNECs) under regulations relating to certain qualified retirement plans that contain cash or deferred arrangements under section 401(k) or that provide for matching contributions or employee contributions under section 401(m). Under these regulations, employer contributions to a plan would be able to qualify as QMACs or QNECs if they satisfy applicable nonforfeitability and distribution requirements at the time they are allocated to participants' accounts, but need not meet these requirements when they are contributed to the plan. These regulations would affect participants in, beneficiaries of, employers maintaining, and administrators of tax-qualified plans that contain cash or deferred arrangements or provide for matching contributions or employee contributions.
82 FR 1629 - Chapter 4 Regulations Relating to Verification and Certification Requirements for Certain Entities and Reporting by Foreign Financial Institutions.
This document contains proposed regulations under chapter 4 of Subtitle A (sections 1471 through 1474) of the Internal Revenue Code of 1986 (Code) describing the verification requirements (including certifications of compliance) and events of default for entities that agree to perform the chapter 4 due diligence, withholding, and reporting requirements on behalf of certain foreign financial institutions (FFIs) or the chapter 4 due diligence and reporting obligations on behalf of certain non-financial foreign entities. These proposed regulations also describe the certification requirements and procedures for IRS's review of certain trustees of trustee-documented trusts and the procedures for IRS's review of periodic certifications provided by registered deemed-compliant FFIs. In addition, these proposed regulations describe the procedures for future modifications to the requirements for certifications of compliance for participating FFIs. These proposed regulations also describe the requirements for certifications of compliance for participating FFIs that are members of consolidated compliance groups. In addition, in the Rules and Regulations section of this issue of the Federal Register, the Department of the Treasury (Treasury Department) and IRS are issuing temporary regulations that provide additional guidance under chapter 4 (temporary chapter 4 regulations). The text of the temporary chapter 4 regulations also serves as the text of the regulations contained in this document that are proposed by cross-reference to the temporary chapter 4 regulations. The preamble to the temporary chapter 4 regulations explains the temporary chapter 4 regulations and these proposed regulations that cross-reference to the temporary chapter 4 regulations.
In the Rules and Regulations section of this issue of the Federal Register, the Department of the Treasury (Treasury Department) and the IRS are issuing temporary regulations (TD 9808) that revise certain provisions of the final regulations regarding withholding of tax on certain U. S. source income paid to foreign persons and requirements for certain claims for refund or credit of income tax made by foreign persons. The text of the temporary regulations also serves as the text of these proposed regulations.
This document contains final and temporary regulations regarding withholding of tax on certain U. S. source income paid to foreign persons, information reporting and backup withholding with respect to payments made to certain U. S. persons, and portfolio interest paid to nonresident alien individuals and foreign corporations. This document finalizes (with minor changes) certain proposed regulations under chapters 3 and 61 and sections 871, 3406, and 6402 of the Internal Revenue Code of 1986 (Code), and withdraws corresponding temporary regulations. This document also includes temporary regulations providing additional rules under chapter 3 of the Code. The text of the temporary regulations also serves as the text of the proposed regulations set forth in a notice of proposed rulemaking published in the Proposed Rules section of this issue of the Federal Register . The temporary regulations affect persons making payments of U. S. source income to foreign persons.
This document contains final and temporary regulations under chapter 4 of Subtitle A (sections 1471 through 1474) of the Internal Revenue Code of 1986 (Code) regarding information reporting by foreign financial institutions (FFIs) with respect to U. S. accounts and withholding on certain payments to FFIs and other foreign entities. This document finalizes (with changes) certain proposed regulations under chapter 4, and withdraws corresponding temporary regulations. This document also includes temporary regulations providing additional rules under chapter 4. The text of the temporary regulations also serves as the text of proposed regulations set forth in a notice of proposed rulemaking published in the Proposed Rules section of this issue of the Federal Register . The regulations included in this document affect persons making certain U. S.-related payments to FFIs and other foreign persons and payments by FFIs to other persons.
81 FR 96374 - Information Returns; Winnings From Bingo, Keno, and Slot Machines.
This document contains final regulations under section 6041 regarding the filing of information returns to report winnings from bingo, keno, and slot machine play. The rules update the existing requirements regarding the filing, form, and content of such information returns; allow for an additional form of payee identification; and provide an optional aggregate reporting method. The final regulations affect persons who pay winnings of $1,200 or more from bingo and slot machine play, $1,500 or more from keno, and recipients of such payments.
81 FR 95911 - Mortality Tables for Determining Present Value Under Defined Benefit Pension Plans.
This document contains proposed regulations prescribing mortality tables to be used by most defined benefit pension plans. The tables specify the probability of survival year-by-year for an individual based on age, gender, and other factors. This information is used (together with other actuarial assumptions) to calculate the present value of a stream of expected future benefit payments for purposes of determining the minimum funding requirements for the plan. These mortality tables are also relevant to determining the minimum required amount of a lump-sum distribution from such a plan. In addition, this document contains proposed regulations to update the requirements that a plan sponsor must meet in order to obtain IRS approval to use mortality tables specific to the plan for minimum funding purposes (instead of the generally applicable mortality tables). These regulations affect participants in, beneficiaries of, employers maintaining, and administrators of certain retirement plans.
This document provides proposed changes to the regulations under section 468A of the Internal Revenue Code of 1986 (Code) relating to deductions for contributions to trusts maintained for decommissioning nuclear power plants and the use of the amounts in those trusts to decommission nuclear plants. The proposed regulations revise certain provisions to: Address issues that have arisen as more nuclear plants have begun the decommissioning process; and clarify provisions in the current regulations regarding self-dealing and the definition of substantial completion of decommissioning.
81 FR 95459 - Definitions and Reporting Requirements for Shareholders of Passive Foreign Investment Companies.
This document contains final regulations that provide guidance on determining ownership of a passive foreign investment company (PFIC) and on certain annual reporting requirements for shareholders of PFICs to file Form 8621, “Information Return by a Shareholder of a Passive Foreign Investment Company or Qualified Electing Fund.” In addition, the final regulations provide guidance on an exception to the requirement for certain shareholders of foreign corporations to file Form 5471, “Information Return of U. S. Persons with Respect to Certain Foreign Corporations.” The regulations finalize proposed regulations and withdraw temporary regulations published on December 31, 2013. The final regulations affect United States persons that own interests in PFICs, and certain United States shareholders of foreign corporations.
This document contains corrections to the final regulations (TD 9792) that were published in the Federal Register on Thursday, November 3, 2016 (81 FR 76497). The final regulations provide rules regarding the treatment as United States property of property held by a controlled foreign corporation (CFC) in connection with certain transactions involving partnerships.
This document contains corrections to the final regulations (TD 9792) that were published in the Federal Register on Thursday, November 3, 2016 (81 FR 76497). The final regulations provide rules regarding the treatment as United States property of property held by a controlled foreign corporation (CFC) in connection with certain transactions involving partnerships.
This document contains corrections to a notice of proposed rulemaking (REG-114734-16) that was published in the Federal Register on Thursday, November 3, 2016 (81 FR 76542). The proposed regulations provide rules regarding the determination of the amount of the United States property treated as held by a controlled foreign corporation (CFC) through a partnership.
81 FR 91738 - Guidance Under Section 355(e) Regarding Predecessors, Successors, and Limitation on Gain Recognition; Guidance Under Section 355(f)
This document contains temporary regulations that provide guidance regarding the distribution by a distributing corporation of stock or securities of a controlled corporation without the recognition of income, gain, or loss. The temporary regulations provide guidance in determining whether a corporation is a predecessor or successor of a distributing or controlled corporation for purposes of the exception under section 355(e) of the Internal Revenue Code (Code) to the nonrecognition treatment afforded qualifying distributions, and they provide certain limitations on the recognition of gain in certain cases involving a predecessor of a distributing corporation. The temporary regulations also provide rules regarding the extent to which section 355(f) of the Code causes a distributing corporation (and in certain cases its shareholders) to recognize income or gain on the distribution of stock or securities of a controlled corporation. These temporary regulations affect corporations that distribute the stock or securities of controlled corporations and the shareholders or security holders of those distributing corporations. The text of these temporary regulations also serves as the text of the proposed regulations in the related notice of proposed rulemaking (REG-140328-15) set forth in the Proposed Rules section in this issue of the Federal Register .
This document contains final regulations relating to the health insurance premium tax credit (premium tax credit). These final regulations affect individuals who enroll in qualified health plans through Health Insurance Exchanges (Exchanges, also called Marketplaces) and claim the premium tax credit, and Exchanges that make qualified health plans available to individuals and employers. These final regulations also affect individuals who are eligible for employer-sponsored health coverage.
In the Rules and Regulations section of this issue of the Federal Register, the IRS is issuing temporary regulations that provide guidance regarding the distribution by a distributing corporation of stock or securities of a controlled corporation without the recognition of income, gain, or loss. The temporary regulations provide guidance in determining whether a corporation is a predecessor or successor of a distributing or controlled corporation for purposes of the exception under section 355(e) of the Internal Revenue Code to the nonrecognition treatment afforded qualifying distributions, and they provide certain limitations on the recognition of gain in certain cases involving a predecessor of a distributing corporation. The temporary regulations also provide rules regarding the extent to which section 355(f) causes a distributing corporation (and in certain cases its shareholders) to recognize income or gain on the distribution of stock or securities of a controlled corporation. Those temporary regulations affect corporations that distribute the stock or securities of controlled corporations and their shareholders or security holders of those distributing corporations. The text of those temporary regulations serves as the text of these proposed regulations.
81 FR 91012 - Treatment of Certain Transfers of Property to Foreign Corporations.
This document contains final regulations relating to certain transfers of property by United States persons to foreign corporations. The final regulations affect United States persons that transfer certain property, including foreign goodwill and going concern value, to foreign corporations in nonrecognition transactions described in section 367 of the Internal Revenue Code (Code). The regulations also combine certain sections of the existing regulations under section 367(a) into a single section. This document also withdraws certain temporary regulations.
81 FR 89849 - Treatment of Certain Domestic Entities Disregarded as Separate From Their Owners as Corporations for Purposes of Section 6038A.
This document contains final regulations that treat a domestic disregarded entity wholly owned by a foreign person as a domestic corporation separate from its owner for the limited purposes of the reporting, record maintenance and associated compliance requirements that apply to 25 percent foreign-owned domestic corporations under section 6038A of the Internal Revenue Code.
81 FR 88999 - Issue Price Definition for Tax-Exempt Bonds.
This document contains final regulations on the definition of issue price for purposes of the arbitrage investment restrictions that apply to tax-exempt bonds and other tax-advantaged bonds. These final regulations affect State and local governments that issue tax-exempt bonds and other tax-advantaged bonds.
81 FR 88806 - Income and Currency Gain or Loss With Respect to a Section 987 QBU.
This document contains final regulations that provide guidance under section 987 of the Internal Revenue Code (Code) regarding the determination of the taxable income or loss of a taxpayer with respect to a qualified business unit (QBU) subject to section 987, as well as the timing, amount, character, and source of any section 987 gain or loss. Taxpayers affected by these regulations are corporations and individuals that own QBUs subject to section 987. In addition, published elsewhere in this issue of the Federal Register, temporary and proposed regulations (the temporary regulations) are being issued under section 987 to address aspects of the application of section 987 not addressed in these final regulations.
This document contains temporary regulations under section 987 of the Internal Revenue Code (Code) relating to the recognition and deferral of foreign currency gain or loss under section 987 with respect to a qualified business unit (QBU) in connection with certain QBU terminations and certain other transactions involving partnerships. This document also contains temporary regulations under section 987 providing: an annual deemed termination election for a section 987 QBU; an elective method, available to taxpayers that make the annual deemed termination election, for translating all items of income or loss with respect to a section 987 QBU at the yearly average exchange rate; rules regarding the treatment of section 988 transactions of a section 987 QBU; rules regarding QBUs with the U. S. dollar as their functional currency; rules regarding combinations and separations of section 987 QBUs; rules regarding the translation of income used to pay creditable foreign income taxes; and rules regarding the allocation of assets and liabilities of certain partnerships for purposes of section 987. Finally, this document contains temporary regulations under section 988 requiring the deferral of certain section 988 loss that arises with respect to related-party loans. The text of these temporary regulations also serves as the text of the proposed regulations set forth in the Proposed Rules section in this issue of the Federal Register . In addition, in the Rules and Regulations section of this issue of the Federal Register, final regulations are being issued under section 987 to provide general guidance under section 987 regarding the determination of the taxable income or loss of a taxpayer with respect to a QBU.
Published elsewhere in this issue of the Federal Register, the Treasury Department and the IRS are issuing temporary regulations under section 987 of the Code relating to the recognition and deferral of foreign currency gain or loss under section 987 with respect to a qualified business unit (QBU) in connection with certain QBU terminations and certain other transactions involving partnerships. The temporary regulations also contain rules providing: An annual deemed termination election for a section 987 QBU; an elective method, available to taxpayers that make the annual deemed termination election, for translating all items of income or loss with respect to a section 987 QBU at the yearly average exchange rate; rules regarding the treatment of section 988 transactions of a section 987 QBU; rules regarding QBUs with the U. S. dollar as their functional currency; rules regarding combinations and separations of section 987 QBUs; rules regarding the translation of income used to pay creditable foreign income taxes; and rules regarding the allocation of assets and liabilities of certain partnerships for purposes of section 987. Finally, the temporary regulations contain rules under section 988 requiring the deferral of certain section 988 loss that arises with respect to related-party loans. The text of the temporary regulations serves as the text of these proposed regulations.
81 FR 88103 - Covered Asset Acquisitions.
This document contains temporary Income Tax Regulations under section 901(m) of the Internal Revenue Code (Code) with respect to transactions that generally are treated as asset acquisitions for U. S. income tax purposes and either are treated as stock acquisitions or are disregarded for foreign income tax purposes. These regulations are necessary to provide guidance on applying section 901(m). The text of the temporary regulations also serves in part as the text of the proposed regulations under section 901(m) (REG-129128-14) published in the Proposed Rules section of this issue of the Federal Register .
This document contains proposed Income Tax Regulations under section 901(m) of the Internal Revenue Code (Code) with respect to transactions that generally are treated as asset acquisitions for U. S. income tax purposes and either are treated as stock acquisitions or are disregarded for foreign income tax purposes. In the Rules and Regulations section of this issue of the Federal Register, temporary regulations are being issued under section 901(m) (the temporary regulations), the text of which serves as the text of a portion of these proposed regulations. These regulations are necessary to provide guidance on applying section 901(m). These regulations affect taxpayers claiming foreign tax credits.
81 FR 87444 - Tax Return Preparer Due Diligence Penalty Under Section 6695(g)
This document contains temporary regulations that modify existing regulations related to the penalty under section 6695(g) of the Internal Revenue Code (Code) relating to tax return preparer due diligence. These temporary regulations implement recent law changes that expand the tax return preparer due diligence penalty under section 6695(g) so that it applies to the child tax credit (CTC), additional child tax credit (ACTC), and the American Opportunity Tax Credit (AOTC), in addition to the earned income credit (EIC). The temporary regulations affect tax return preparers. The substance of the temporary regulations is included in the proposed regulations set forth in the notice of proposed rulemaking on this subject in the Proposed Rules section in this issue of the Federal Register .
In the Rules and Regulations section of this issue of the Federal Register, the IRS is issuing temporary regulations that will modify the existing regulations related to the penalty under section 6695(g) of the Internal Revenue Code (Code) relating to tax return preparer due diligence. The temporary regulations implement recent law changes that expand the tax return preparer due diligence penalty under section 6695(g) so that it applies to the child tax credit (CTC), additional child tax credit (ACTC), and the American Opportunity Tax Credit (AOTC), in addition to the earned income credit (EIC). The text of those regulations also serves as the text of these proposed regulations.
81 FR 86953 - Consistent Basis Reporting Between Estate and Person Acquiring Property From Decedent.
This document contains final regulations that provide transition rules providing that executors and other persons required to file or furnish a statement under section 6035(a)(1) or (2) regarding the value of property included in a decedent's gross estate for federal estate tax purposes before June 30, 2016, need not have done so until June 30, 2016. These final regulations are applicable to executors and other persons who file federal estate tax returns required by section 6018(a) or (b) after July 31, 2015.
81 FR 85450 - Dollar-Value LIFO Regulations: Inventory Price Index Computation (IPIC) Method Pools.
This document contains proposed regulations that relate to the establishment of dollar-value last-in, first-out (LIFO) inventory pools by certain taxpayers that use the inventory price index computation (IPIC) pooling method. The proposed regulations provide rules regarding the proper pooling of manufactured or processed goods and wholesale or retail (resale) goods. The proposed regulations would affect taxpayers who use the IPIC pooling method and whose inventory for a trade or business consists of manufactured or processed goods and resale goods.
81 FR 85190 - Update to Minimum Present Value Requirements for Defined Benefit Plan Distributions.
This document contains proposed regulations providing guidance relating to the minimum present value requirements applicable to certain defined benefit pension plans. These proposed regulations would provide guidance on changes made by the Pension Protection Act of 2006 and would provide other modifications to these rules as well. These regulations would affect participants, beneficiaries, sponsors, and administrators of defined benefit pension plans. This document also provides a notice of a public hearing on these proposed regulations.
81 FR 84518 - Fractions Rule.
This document contains proposed regulations relating to the application of section 514(c)(9)(E) of the Internal Revenue Code (Code) to partnerships that hold debt-financed real property and have one or more (but not all) qualified tax-exempt organization partners within the meaning of section 514(c)(9)(C). The proposed regulations amend the current regulations under section 514(c)(9)(E) to allow certain allocations resulting from specified common business practices to comply with the rules under section 514(c)(9)(E). These regulations affect partnerships with qualified tax-exempt organization partners and their partners.
81 FR 80993 - Liabilities Recognized as Recourse Partnership Liabilities Under Section 752; Correction.
This document contains corrections to final and temporary regulations (TD 9788) that were published in the Federal Register on Wednesday, October 5, 2016 (81 FR 69282). The final and temporary regulations provide rules concerning how liabilities are allocated for purposes of section 707 of the Internal Revenue Code and when certain obligations are recognized for purposes of determining whether a liability is a recourse partnership liability under section 752.
This document contains corrections to final and temporary regulations (TD 9788) that were published in the Federal Register on Wednesday, October 5, 2016 (81 FR 69282). The final and temporary regulations provide rules concerning how liabilities are allocated for purposes of section 707 of the Internal Revenue Code and when certain obligations are recognized for purposes of determining whether a liability is a recourse partnership liability under section 752.

Capital gains exemption stock options

This article discusses the pros and cons of stock options vs shares for employees of Canadian – private and public – companies. The taxation issues are poorly understood and can be very confusing. Current tax regulations can make it difficult for companies to bring new employees and partners in as shareholders.
Stock options are a popular way for companies to attract key employees. They are the next best thing to share ownership. Employees are motivated to add value to their companies in the same way that founder/owners are. Options are also a key part of a compensation package. In larger companies, options contribute substantially – often many times the salary portion – to income. In a recent survey of executive compensation (see vancouversun/execpay), the top 100 BC-based public company executives all earned over $1 million in 2009 income. However, only 5 of them received base salaries over $1 million. Most of the compensation came from stock options – no wonder the CRA (Canada Revenue Agency) wants to tax them!
Unfortunately, tax law can turn stock options into a huge disincentive in attracting key employees. For example , if an employee of a company (private or public) exercises options to buy shares, that employee may have a tax liability even if he sells the shares at a loss. If the company fails, the liability does not disappear. The tax treatment is not the same for Canadian Controlled Private Companies (CCPCs) as it is for public or non-CCPC companies. CCPCs have an advantage over other Canadian companies.
For CCPCs – Canadian Controlled Private Corporations.
This discussion is applicable to Canadian Controlled Private Companies (CCPCs). It addresses how a start-up can best get shares into the hands of employees while being aware of possible tax issues.
To give employees an ownership stake (and incentive) in the company, the best solution is to give them founders shares just like the founders took for themselves when the company was formed. Companies should issue founders shares from treasury as early as possible. Some companies issue extra founders shares and hold them in a trust for future employees. Sometimes, the founders will transfer some of their own founders shares to new partners. As a general rule, try to give employees founders shares early in the company’s life. However, make sure that the shares reverse-vest over time (or based on performance), so that quitters and non-performers don’t get a free ride.
By owning shares in a CCPC (Canadian Controlled Private Corporation) for at least 2 years, shareholders get the benefit of the $750,000 life-time capital gains exemption (i. e. pay no tax on the first $750K in capital gains). This is a HUGE benefit. They also get a 50% deduction on additional gains.
If a company is beyond its start up phase, there is a worry that if these shares are simply given (for free or for pennies) to an employee, CRA (Canada Revenue Agency) considers this an “employment benefit” on which income tax is payable. This benefit is the difference between what the employee paid for the shares and their FMV (Fair Market Value).
This benefit is taxed as regular employment income . For CCPCs, this benefit may be deferred until the shares are sold. If held for more than 2 years, there is also a 50% deduction available on the benefit. If held for less than 2 years, another 50% deduction can be used if the shares where purchased at FMV.
However, if the shares are later sold (or deemed to have been sold by virtue of a liquidation) at a lower price than the FMV at the time of acquisition, the tax on the deferred benefit is STILL DUE. And, although this loss (i. e. the difference between FMV and the selling price) is a “capital loss”, it does not offset the tax owing. It may be possible to claim an ABIL (Allowable Business Investment Loss) to offset the tax owing on the deferred benefit, i. e. if you buy shares in a CCPC, you can claim 50% of your investment loss and deduct from other income.
Other than issuing zero-cost founders shares, the next best approach is to sell shares to employees at a “good” price which one could argue is at FMV considering the substantial restrictions on the shares (eg reverse-vesting and risk of forfeiture). This may work well if the company is still quite young and has not raised substantial sums from independent investors.
(In the case of publicly-listed companies, options grants are the norm since FMV can be readily determined – and a benefit assessed – and because regulations often prevent the issuance of zero-cost shares. But for pubcos and non-CCPCs, the tax on these benefits may not be deferred. It is payable in the year in which the option is exercised. This is a real problem for smaller public, venture-listed companies insofar as this tax forces the option to sell some shares just to be the tax! It discourages ownership. )
Some disadvantages of issuing stock are:
Deferred tax liability if shares are bought below FMV (if you can figure out what FMV is – remember, these shares are highly restrictive and are worth less than those purchased by angels and other investors.) A CRA assessment of the deemed benefit is a remote possibility. May need to defend the FMV. May need independent valuation. (I’ve never heard of this happening.) Need to make sure that shareholder agreement provisions are in place (eg vesting, voting, etc). Issuance of shares at very low prices on a cap table may look bad to new investors (whereas option exercises are considered normal) More shareholders to manage.
The benefits of owning shares are:
Can get up to $750,000 in life-time tax-free capital gains 50% deduction on gains if shares held for more than 2 years OR if shares where issued at FMV Losses in a CCPC can be used as allowable business losses (if the business fails) Can participate in ownership of company – voting, dividends, etc Less dilution than if stock options are issued.
Getting cheap shares into the hands of employees is the best way to go for a CCPC. The only downside risk arises if the company fails in less than two years. (See Bottom Line below) .
[NOTE: Companies can issue shares (instead of options) to employees at any price and not trigger an immediate taxable event – it’s the same as giving an option grant that is immediately exercised. If shares (instead of options) are given at a very low (e. g. zero) price, fewer shares can be issued than when granting options with a higher exercise price.]
To avoid the risk of having to pay the tax on the deferred benefit if shares are issued to an employee below the FMV, options are often granted. This is only a risk if shares are ultimately sold below the FMV, as may be the case in a bankruptcy . Stock options, if unexercised, avoid this potential problem. An option gives one the right to buy a certain number of shares for a stated price (the exercise price) for a given period of time. The is no liability at the time that options are granted. Only in the year that options are exercised, is there is a tax liability. For CCPCs this liability can be deferred until the shares are actually sold. If the shares are held for more than 2 years, this tax liability is calculated at 50% of the benefit. That is, both a deferral and a deduction of 50% are available to those having exercised options. (If shares are held for less than 2 years, a 50% deduction is available if shares were purchased at FMV.)
Some disadvantages with stock options are:
The tax liability (if options are exercised) is never erased – this is exactly the same scenario as if shares were given. The lifetime capital gains exemption cannot be used unless the shares – not the options – are held for 2 years after exercising. Capital gains are calculated on the difference between the selling price and the FMV when exercised. Must hold the shares for 2 years, after exercising the option to get the 50% deduction. (If exercise price of option = FMV at date of option grant, a 50% deduction is also available). The benefit is considered “income”, not a capital gain and if shares are subsequently sold at a loss, the income benefit cannot be reduced by this capital loss. The tax risk increases over time since it is the difference between FMV and exercise price at the time of exercise that sets up the contingent tax liability, so the longer you wait to exercise (assuming steadily increasing FMV), the greater the potential tax liability. Options do not constitute ownership; optioned shares cannot be voted. Large option pools are negatively viewed by investors because they may cause substantial future dilution (unlike public companies that are generally limited to 10% in options, private companies can have very large option pools). Still need to have a defensible FMV; may need independent valuation. It may become a real headache if CRA requires that this be done retroactively when an exit is achieved. They could expire too soon. May need to have a very long term, say 10 years or more. Showing lots of stock options on the company’s cap table directly impacts (negatively) the per-share valuation in on-going financings since investors always look at all outstanding options as outstanding shares.
Some benefits with stock options are:
No tax liability when options are received, only when they are exercised. No cash outlay required until exercised and even then, it may be minimal. Can exercise options to buy shares immediately at discounted prices without having to pay any tax until shares are sold. An early exercise avoids a higher FMV, and hence avoids a greater taxable benefit, later.
From the company’s perspective, granting shares (instead of options) at a very low price means that fewer shares need to be issued – which is good for all shareholders. For example, giving shares at a penny instead of granting options exercisable at 50 cents means that more options must be granted which means greater dilution later when an exit is realized . The extra 49 cents doesn’t do much for shareholders as the exercise amount by then is nominal compared to the exit value. That amount will go right back to the new owner of the company meanwhile diluting all shareholders participating in the exit!
Action item for investors: check your company’s cap table for options and get rid of them! Give shares instead that are notionally equal to the Black-Scholes value of the option. Example, Joe Blow holds an option to buy 100K shares at 60 cents. The shares are currently valued at 75 cents (based on recent investments). The value of the options is determined to be 35 cents (i. e. $35K in total value). The 35 cents is based on the value of the option (say 20 cents) plus the in-the-money amount of 15 cents. As a rule of thumb, when an option is issued with an exercise price equal to current share price, an approximate determination of the options value is taken by dividing the price by 3 which in this example is 60/3 = 20 cents. Now, take the total value of $35K and issue 46,666 shares for $1.00 (because 46,666 shares at 75 cents = $35K). This is better than showing 100K shares as options on the cap table!!
RECOMMENDATION FOR CCPCs :
Grant stock options, exercisable at a nominal cost, say 1 cent – good for at least 10 years or more. Suggest that option holders exercise their option and buy shares immediately (just skip step #1 altogether) Make sure that grantees understand that if they exercise early or immediately, they start the 2-year clock on the deduction and also get the lifetime capital gains exemption. (They should also understand that there may be a possible downside in so doing – i. e. the liability on the “benefit” when options are exercised is still taxable even if the company fails – in which case, they can still claim the ABIL offset. Grantees may elect to trade-off this potential liability by forfeiting the deduction and exemption and not exercising until there is an exit in which case they take no risk but have a much lower – as much as 50% lower – profit).:
An employee is given an option to buy shares for a penny each. Shares are currently being sold to investors for $1.00 each (CRA would argue that the $1.00 price is the FMV). If the employee exercises the option immediately and buys shares, then he is deemed to have received an employment benefit of 99 cents which is fully taxable as income BUT both a DEFERRAL and a DEDUCTION may be available. First, the tax on this income can be deferred until the shares are sold (if the company fails, they are considered to be sold). Companies must file T4 slips with CRA (so you can’t hide this sale). Second, if the Shares (not the Option) are held for at least 2 years, then only 50%, i. e. 49.5 cents is taxed as income. The difference between the selling price (and the FMV at the time the shares were acquired) is taxed as a capital gain which is also eligible for a $750K life-time exemption! If the shares are sold for $1.00 or more – no problem! But, if the shares are sold for less than $1.00, the employee is still on the hook for the 99 cent (or .495 cent) benefit and although he would have a capital loss , it cannot be used to offset the liability. He can mitigate this by claiming an Allowable Business Investment Loss (ABIL). 50% of the ABIL can be reduced to offset employment income. In this example, 49.5 cents would be allowed as a deduction against the 49.5 cents that is taxed as income, leaving the employee in a neutral position with respect to tax liability. Caution – claiming an ABIL may not work if the company has lost its CCPC status along the way.
(Note: I’ve heard of people in this situation claiming that the FMV is exactly what they paid since it was negotiated at arms-length, the shares could not be sold, the company was desperate, etc, etc. Their attitude is let CRA challenge it. That’s OK as long as the Company didn’t file a T4, as it should but likely won’t if it’s bankrupt.)
On the other hand, if the company succeeds, employees can enjoy tax-free gains (up to $750K) without having to put up much capital and taking only a limited risk.
If the employee holds an option until the company is sold (or until the shares become liquid) and then exercises the option and immediately sells the shares, the employee’s entire gain (i. e. the difference between his selling price and the penny he paid for each share) is fully taxed as employment income and there is no 50% deduction available (unless the exercise price of the option = FMV when the option was granted).
THE BOTTOM LINE:
The best deal for both the company (if it’s a CCPC) and its employees is to issue shares to employees for a nominal cost, say 1 cent per share. If this grant is to garner an employee’s commitment for future work, reverse-vesting terms should be agreed to before the shares are issued. To determine the number of shares, start by arbitrarily setting the price per share. This could be the most recent price paid by arms-length investors or some other price that you can argue is reasonable under the circumstances. Let’s say that the price per share is $1.00 and you want to give your recently recruited CFO a $250K signing bonus. Therefore, he’d get 250K shares as an incentive (these should vest daily over a 3-year period). He pays $2,500 for these. Tax-wise, he is now liable for the tax on $247.5K in employment income . However, he can defer payment of this tax until the shares are sold.
Here are the possible outcomes and consequences:
a)Shares are sold for $1.00 or more after holding the shares for at least 2 years: he is taxed on income of 50% of $247.5K (i. e. $250K minus the $2,500 paid for the shares), i. e. the deferred benefit, less the 50% deduction PLUS a capital gain on any proceeds above his $1.00 per share “cost”. This gain is taxed at a rate of 50% and, if not previously claimed, his first $750K in gains is completely tax-free.
b)Shares are sold for $1.00 or more but in less than 2 years: he is taxed on income of $247.5K, i. e. the deferred benefit, as there is no deduction available PLUS a capital gain on any proceeds above his $1.00 per share “cost”. He does not benefit from the 50% deduction on the employment benefit nor the 50% capital gains deduction. This is why it makes sense to own shares as soon as possible to start the 2-year clock running.
c)Shares are sold for less than 1.00 after holding the shares for more than 2 years: he is taxed on income of 50% of $247.5K, i. e. the deferred benefit less the 50% deduction. He can offset this tax by claiming an ABIL. He can take 50% of the difference between his selling price and $1.00 and deduct that from his employment income – this is a direct offset to the deferred benefit. If the company fails and the shares are worthless, he is taxed on employment income of 50% of $247,500 MINUS 50% of $250K – i. e. no tax (indeed, a small refund).
d)Shares are sold for less than 1.00 after holding the shares for less than 2 years: he is taxed on income of $247.5K, i. e. the deferred benefit as there is no deduction available. He can offset this tax by claiming an ABIL. He can take 50% of the difference between his selling price and $1.00 and deduct that from his employment income – this is a partial offset to the deferred benefit. If the company fails and the shares are worthless, he is taxed on employment income of $247,500 MINUS 50% of $250K = $122,500. NOT GOOD! This is the situation that must be avoided. Why pay tax on $122.5K of unrealized income that has never seen the light of day? How? Make sure you let 2 years pass before liquidating if at all possible. You can also argue that the benefit was not $247,500 because there was no market for the shares, they were restricted, you could not sell any, etc. Let CRA challenge you and hope they won’t (I’ve not heard of any cases where they have – in the case of CCPCs).
Why bother with options when the benefits of share ownership are so compelling? And the only possible financial risk to an employee getting shares instead of stock options arises in (d) above if shares are sold at a loss in less than 2 years. If the company fails that quickly, the FMV was likely never very high and besides, you can stretch the liquidation date if you need to.
Contractors and Consultants.
The deferral of tax liability in respect of CCPCs is granted only to employees of the CCPC in question (or of a CCPC with which the employer CCPC does not deal at arm’s length). Contractors and consultants are not entitled to the benefit of the deferral. Consequently, contractors and consultants will be liable to pay tax upon exercise of any options.
Never underestimate the power of the Canada Revenue Agency. One might expect them to chase after the winners – those with big gains on successful exits but what about the folks that got stock options, deferred the benefit and sold their shares for zip? Will CRA kick the losers when they’re down?
For Publicly Listed Corporations and non-CCPCs.
In the case of public companies, stock option rules are different. The main difference is that if an employee exercises an option for shares in a public company, he has an immediate tax liability.
Up until the Federal Budget of March 4th, 2010, it was possible for an employee to defer the tax until he actually sells the shares. But now, when you exercise a stock option and buy shares in the company you work for, CRA wants you to pay tax immediately on any unrealized “paper” profit even if you haven’t sold any shares.
Furthermore, CRA now wants your company to withhold the tax on this artificial profit. This discourages the holding of shares for future gains. If the company is a junior Venture-Exchange listed company, where will it find the cash to pay the tax – especially if it is thinly traded?
This process is not only an accounting nightmare for you and the company – it’s also fundamentally wrong in that CRA is making your buy/sell decisions for you.
It is also wrong in that stock options will no longer be an attractive recruiting inducement. Emerging companies will find it much harder to attract talent.
It will also be a major impediment to private companies that wish to go public. In the going-public process, employees usually exercise their stock options (often to meet regulatory limits on option pools). This could result in a tax bill of millions of dollars to the company. Also, it won’t look good to new investors to see employees selling their shares during an IPO even though they have to.
Before the March 4th budget, you could defer the tax on any paper profit until the year in which you actually sell the shares that you bought and get real cash in hand. This was a big headache for those who bought shares only to see the price of the shares drop.
The stories you may have heard about Nortel or JDS Uniphase employees going broke to pay tax on worthless shares are true. They exercised options when shares were trading north of $100, giving them huge paper profits and substantial tax liabilities. But when the shares tanked, there was never any cash to cover the liability – nor was there any offset to mitigate the pain. The only relief is that the drop in value becomes a capital loss but this can only be applied to offset capital gains. In the meantime, though, the cash amount required to pay CRA can bankrupt you.
CRA argues that the new rule will force you to sell shares right away, thereby avoiding a future loss. (Aren’t you glad that they’re looking after you so well?) But, that’s only because the stupid “deemed benefit” is taxed in the first instance.
Example: You are the CFO of a young tech company that recruited you from Silicon Valley. You have a 5-year option to buy 100,000 shares at $1.00. Near the expiration date, you borrow $100,000 and are now a shareholder. On that date, the shares are worth $11.00. Your tax bill on this is roughly $220,000 (50% inclusion rate X the top marginal tax rate of 44%X $1 million in unrealized profit) which you must pay immediately (and your Company must “withhold” this same amount). Unless you’ve got deep pockets, you’ll have to sell 29,000 shares to cover your costs – 20,000 more than if you did a simple cashless exercise. So much for being an owner! In this example, if the company’s shares drop in price and you later sell the shares for $2.00, you’ll be in the hole $120,000 ($200,000 less $320,000) whereas you should have doubled your money! Sure, you have a capital loss of $9 (i. e. $11 less $2) but when can you ever use that?
As part of the March 4 changes, CRA will let the Nortel-like victims of the past (i. e. those that have used the previously-available deferral election) file a special election that will limit their tax liability to the actual proceeds received, effectively breaking-even but losing any potential upside benefit. I guess this will make people with deferrals pony up sooner. The mechanics of this are still not well defined. (see the paragraph titled “deferrals election” below)
Interestingly, warrants (similar to options) given to investors are NOT taxed until benefits are realized. Options should be the same. Investors get warrants as a bonus for making an equity investment and taking a risk. Employees get options as a bonus for making a sweat-equity investment and taking a risk. Why should they be treated less favorably?
I don’t understand how such punitive measures make their way into our tax system. Surely, no Member of Parliament (MP) woke up one night with a Eureka moment on how the government can screw entrepreneurs and risk takers. Such notions can only come from jealous bureaucrats who can’t identify with Canada’s innovators. What are they thinking?
A common view is that large public corporations, while it creates more accounting work for them, aren’t that upset about this tax. They do see it as a benefit and for them and their employees, it might be better to sell shares, take the profit and run. For smaller emerging companies – especially those listed on the TSX Venture exchange, the situation is different. For one thing, a forced sale into the market can cause a price crash, meaning having to sell even more shares. Managers and Directors of these companies would be seen as insiders bailing out. Not good.
The rules are complex and hard to understand. The differences between CCPCs, non-CCPCs, public companies and companies in transition between being private and non-private give you a headache just trying to understand the various scenarios. Even while writing this article, I talked to various experts who gave me somewhat different interpretations. Does your head hurt yet? What happens if you do this…or if you do that? It’s messy and unnecessary.
The solution: don’t tax artificial stock option “benefits” until shares are sold and profits are realized. For that matter, let’s go all the way and let companies give stock – not stock option – grants to employees.
I wonder how many MPs know about this tax measure? I wonder if any even know about it. It’s a complex matter and not one that affects a large percentage of the population – certainly not something that the press can get too excited about. I’m sure that if they are made aware of it, they’d speak against it. After all, on the innovation front, it’s yet another impediment to economic growth.
For another good article on the subject, please read Jim Fletcher’s piece on the 2010 Budget on BootUp Entrepreneurial Society’s blog.
For those who exercised an option before March 2010, and deferred the benefit, CRA is making a special concession. On the surface it looks simple: You are allowed to file an election that lets you limit your total tax bill to the cash you actually receive when you sell the shares (which will likely leave you with nothing for your hard work) rather than be subject to taxes on income you never realized (as is the case before March 2010). Indeed, CRA thinks it’s doing everyone a big favor because it’s being kind in helping with a mess that it created in the first place!
There’s a detailed and lengthy discussion in an article by Mark Woltersdorf of Fraser Milner Casgrain in “Tax Notes” by CCH Canadian. The key point in the article is that you have until 2015 to decide how to handle any previously deferrals. The decision is not straightforward because it depends on an individual’s specific circumstances. For example, if there are other capital gains that could be offset, filing the election would result in not being able to offset these. The article states: “On filing the election, the employee is deemed to have realized a taxable capital gain equal to one-half of the lesser of the employment income or the capital loss arising on the sale of optioned shares. The deemed taxable capital gain will be offset (partially or in full) by the allowable capital loss arising from the disposition of the optioned share. What is the value of the allowable capital loss that is used, and therefore, not available to offset other taxable capital gains?” The article gives a few good examples to illustrate various scenarios. So, if you’re in this situation – do your analysis. I tried to link to the article, but it’s a pay-for publication, so that’s not available. Your tax accountant might give you a copy.
Thanks to Steve Reed of Manning Elliott in Vancouver for his tax insights and to Jim Fletcher, an active angel investor, for his contributions to this article.
Footnotes (the devil is in the details):
1.”Shares” as referred to herein means “Prescribed Shares” in the Income Tax Act. Generally this means ordinary common shares – BUT – if a Company has a right of first refusal to buy back shares, they may no longer qualify for the same tax treatment.
2.There are really two 50% deductions are available: The regular capital gains deduction which permits a 50% deduction on capital gains made on shares that are acquired at FMV and the 50% deduction available to offset the employment income benefit on shares that are held for more than 2 years. (Of course, only one 50% deduction is available. )
3.CCPC status may unknowingly be forfeited. For example, if a US investor has certain rights whereby he has, or may have, “control”, the company may be deemed to be a non-CCPC.
37 Responses to “Shares vs Stock Options”
Mike – thanks for this very valuable contribution to the community. Options are one of the most common mistakes I see in corporate structures. A couple of additional points:
1. When companies use options, or vesting stock, they are subject to the stock based compensation rules. This makes the preparation of financial statements much more complicated and expensive.
2. Options are also much more dilutive. Few people actually ‘get this’ but the short description is that everyone I’ve met always counts all of the options into the fully diluted calculation without considering the additional cash from the exercise. That makes the dilution effectively equal between a share or option.
But employees consider an option as worth much less than a share. So to get the same incentive, in practice, you have to allocate more options than shares.
3. The additional governance complexity you point out is a consideration. I prefer to make the employee shares a different class with equal economic advantage, but without votes.
In the US, options have become so much less desirable that many companies, for example Microsoft, have just stopped using them as a way to motivate the team.
It would be interesting to see comments here from some of our friends in the legal and accounting professions. They are often the ones advising young companies on this.
Thanks again for the excellent summary.
Your input is excellent but I am curious about the implications of FMV and the Issuance of extra founders shares set aside in Trust. Although we have been ‘doing business as’… for over a year now, we are now preparing to incorporate and issue founders shares. Are you saying that although I can issue additional founders shares without tax implication, in the beginning, in trust to be issued to new staff at a later date, if I transfer them at a later date they may have serious tax implications? Re-worded, do these shares even though they have already been issued and all new shareholders would be aware of the dilution factor of those shares, once a major investor comes on board, does the transfer of those shares now represent a benefit and therefore a differed tax presence? If so what would be the point in issuing them in trust. Why not simply issue them. If I am guessing at the reason, it would be because once you have a tangible investor, you have a distinctive FMV and therefore your later issuance of founders shares represents a very real conflict in the interests to your new higher paying shareholders?
Good questions. A trust may be useful in that you would allocate shares in your cap table and all shareholders would regard them as part of the founders block.
As a CCPC you can issue shares at any time at any price (just make sure you comply with the securities regulations). Suppose that an investor has just paid $1.00 per share. If an employee gets 100,000 shares for free (say $.0001 per share), she has a “deferred employment benefit” of $100K on which she has to pay tax WHEN she sells the shares. You might be thinking that the investor who just paid $1.00 will be annoyed if someone else gets shares for free, right? In this case you have to explain to the investor that a) the employee is getting this break as part of her compensation package (and working for a low salary) and b) it’s a good deal for all shareholders because if you issued options at $1.00, you’d likely have to issue more than 100,000 which means more dilution later to all shareholders. Also, by her holding CCPC shares for 2 years, she gets up to $750K in capital gains tax-free!
I believe that I read in your article that the founders block in a publicly held corporation can be as much as 10% of the shares in a company, or maybe that was the block which was allocated to options in a public company. Anyways, is there a maximum percentage of shares that can be issued into trust or is this simply a common sense issue where if you have way too many shares in trust that you will more than likely make some of your early investors a bit concerned about investing in your company with so many shares outstanding?
10% is a kind of a rule of thumb for public and private companies. Public companies are restricted – usually to a max of but more normally 10%. There’s no limit on private companies. If the shares are all issued, it shouldnt make investors nervous – it’s when they get diluted from stock option exercises that they get nervous.
Thanks very much for the super helpful post! I have been trying to figure this all out for the past year, reading so many different articles and sources that left me completely confused. Your article was amazing summary of all the scenarios, written in easy to understand style and will really help me with my venture plans… and also help my students I teach as well in an entrepreneurship class.
Mike thank you for your input. Do you know if a public Canadian Company can grant its Directors the stock option on the name of the Director’s private company and not in the name of the director him/herself?
I don’t see why not. But, check with a secuties lawyer. Also, check any tax implications either way. Mike.
Do these rules apply regardless of the company being public or private? My accountant seems to think so…
The rules are quite different for public vs private companies. They are more favorable to private companies because stock option benefits can be deferred whereas there is no deferral for public companies. It means that, in a public company, you are forced to sell some shares immediately so that you can pay the taxes. It discourages ownership which is unfortunate.
What are the tax implications for purchase, nominal value transfer or gifting of shares in a CCPC between two shareholders of the CCPC? Thx–this article seems to be one of the best around on this topic.
I think it depends on the nature of the transaction and the current value of the shares.
If you make a disposition, e. g. as a gift, you might have to pay tax on the appreciated value. The recipient wouldn’t have a tax issue until the shares are sold.
If you give shares to someone in lieu of pay, then they will have to pay tax on the benefit (diff between fair value and their cost) and you will have to pay tax on the appreciated value.
I have vested share options in a private canadian corporation that I VERY recently exercised at a penny a share. The fair market value is 70 cents a share. In the next month or two we expect the company to be sold to some corporation overseas for at least $1 a share. Am I right in expecting that the 69cents between the fair market value (70cents) and my exercise price (1 cent) will be taxed as income, while the gain between 70cents and the $1+ per share the company is sold at will be taxed as captial gains?
There is absolutely no 2 year hold period possible, but some people think the quick time period (1-2 months) between exercising options and the sale of the company might somehow be ‘exempt’ from going the capital gains route and instead just be treated as regular income.
Thanks so much for the article Mike. It is very clear.
What happens if say you hold the shares of a CCPC for 1.5 years and at that point it becomes public (IPO) and is no longer CCPC? Do you not get the 750K tax exemption or the other goodies? Even if you wait another 0.5 year before selling so it’s 2 years in total?
I’m pretty sure you’re stuck. And, it’s just not being a CCPC that’s required – the CCPC has to be a QSB (Qualified Small Business-check CRA Website).
What are the benefits of receiving “no-cost founder shares”?
Are the shares deemed to have a different FMV, ex. the FMV when the company was established?
Great article, I’m just a little unsure of the definition for founder shares.
The benefit is that they cost you nothing and will someday, hopefully, be very valuable. The FMV (Fair Market Value) is what they are worth on the day you get them. Founders shares are usually issued when the company is founded (started) and at its early stages when partners are brought in to work in the company long before investors are brought in. At this stage, they are usually considered to be of zero value (at least for tax purposes).
Mike…. thank you (again) for your helpful post (May 2011!).
I am interested in the SHARE issue concept (“founders shares”) – specifically the opportunity for the recipient employee to defer tax for 2 years or more. We have recently awarded two employees with share ownership, but everything I can find on CRA web site indicates that such awards are immediately taxable.
I can not find any CRA reference to the defef\rrment opportunity. Specifically CRA bulletin IT113R4 provides advice on this – but not about deferrment.
Can you point me to a CRA reference in this regard?
On CRA’s website, there are instruction on completing the tax return Line 101 Security Option Benefits where it says: “If your employer is a Canadian controlled private corporation (CCPC), which you deal with at arm’s length, you only have to report this taxable benefit on your tax return for the year you sell the securities. If your employer is not a CCPC you may have to report taxable benefits you received in (or carried forward to) the year you exercise your stock option.”
BUT… the sentence you quoted: “On CRA’s website, there are instruction on completing the tax return Line 101 Security Option Benefits where it says: “If your employer is a Canadian controlled private corporation (CCPC), which you deal with at arm’s length, you only have to report this taxable benefit on your tax return for the year you sell the securities.” …
is preceded by “A security option benefit results when you buy securities through your employer at apre-established price which is less than the fair market value of the securities.”
So … doesn’t that mean this reference is related to stock option plans (i. e. “a pre-established price”)…. not to a general award or gift of shares ?
If you get below-cost shares in a QSB (regardless of whether they are a gift, a discount, bonus, etc) then you have a benefit. This benefit can be defered until you sell the shares.
For the first time in many years I have exercised options of a public company. I have “Security Options Benefits” and “Security Options Deductions” on my T4, leaving me with 50% of the gain on the option sale within my income.
I also have a tremendous amount of carryforward capital losses. I was hoping the the option gain could be fully offset by these losses, as they both arise from publicly traded stock.
But I can find no method of “deducting” my capital losses against the income that has been built into my T4. This income IS the result of a capital gain on the disposition of the share options, so why can’t I find a way to use my loss carryforward against it?
To add insult to this, last year I had “qualified” gains on the disposition of farm property. Instead of allowing me to deduct the gain from my “lifetime exemption”, the CRA forced me to us my carryforward capital losses. When I do finally have gains on shares, my losses won’t be there to limit the tax.
Wouldn’t be so awful, except I made those losses on borrowed money, and I need all the gains to pay back the loans. I have loans outstanding after the underlying asset has gone – sold at a loss. It’s simply crazy!
Now here I am with legitimate gains, but can’t find a way to exercise the losses against them.
I sympathize with you! The only thing I can offer is that you can at least deduct the interest on your loan. Also, let’s hope you have lots of capital gains in the future against whcih you can use your accrued losses.
Excellent post Mike! Very informative.
If a corporation was created 17 years ago and some employees worked there for 15 years, can founder shares still be created and assigned to these employees?
Is there a tax benefit of getting these shares assigned to a corporation the employee owns? Instead of big corporation providing shares to directly to the employee they first go to another corporation that the employee owns?
Regardless of the above, “the bottom line” section of your post still sounds like an amazing deal. Most taxes deferred. Assuming no change in valuation eventually taxed at normal employment income like figure of gifted shares in the event of a sale. Seems too good to be true!
Can you recommend further reading materials? I am especially interested in private established corporations gifting shares to their employees.
Rob, you can create “founders” shares any time you like – that is, by founders shares I trust you mean zero-cost shares. I believe that if the shares are issued to a corporation, there’d be taxable benefit although I’m not sure if it can be deferred. I suggest that you check with your own accountant about your particular situation – just to be safe.
a CCPC grants share to employee with an FMV and the employee could defer the tax benefits till selling the shares. If the employee never sells the shares because the later share value is lower than the previous FMV when shares granted, will deferred tax be erased?
I don’t think the benefit ever gets erased. And there’s never a “never sell” because either the company or the shareholder will die someday (and then there’s a deemed disposition).
thanks Mike! Oh, yes, the shares could be sold passively. how CRA could determine the FMV of a shared granted by a CCPC 5 years ago?
Yes, that’s the challenge. I’ve never actually heard of CRA determining this for a small CCPC startup. I’d love to hear from anyone that has.
Hi Mike, Thanks for the very informative article. Can you please refer me to the section of the Income Tax Act that allows for a deferral AND/OR 50% deduction as it relates to the taxable benefit under a SHARE sale. I believe what you are looking at covers Options and not shares. Thanks, Levi.
Follow up the questions above from Ken and Levi, has this been resolved re whether these rules only apply to options and not shares? Ken and Levi were looking for confirmation/references to the tax act allowing the deferral relating to shares (not stock options). Thanks for any comments on this.
The rules relate to shares. Options are just a right to buy shares. If you acquire shares below the so-called market value, this could be due to an option that you’ve exercised or simply due to an agreement (eg employment agreement). Regardless of how or why you got “cheap” shares, the tax liability kicks in when you get the “benefit”. This benefit is taxable but it can be deferred (for a private company) until you sell the shares. There is no tax due when you receive stock options – regardless of the terms of the option grant.
Hi, Mike, excellent article. I’m wondering if Founders Share should be hold by founder or company, if hold by founder, can deferred rules apply?
Companies don’t hold shares in themselves. Founders shares would be held by individual “founders” which could really be anyone you wish to deal in.
Great article. Have any of these provisions been updated in the 6 years since the article was originally published? We’re based in Toronto and setting up a new tech startup. We’ve decided to incorporate in Delaware as we want to eventually attract money from the valley. But for founders and key employees it seems that both options and founders shares could be problematic? as a non CCPC, Canadian employees who receive options would be in a situation similar to your CFO with 100,000 options in a Silicon Valley startup – they would have a tax liability on the FMV at time of exercising, due immediately. Is this still the case?
If we issue shares (founder shares?) as a non-CCPC, even with reverse vesting (or RSU equivalents), it seems there would be an immediate tax liability based on FMV at the time the shares are issued – am I understanding that correctly?
I’m not aware of any changes in the past 6 years since I wrote the post. Yes, the rules are different in the USA. Not as good as in Canada. Many startups I know have no trouble attracting Valley Capital because they are CCPCs. In your case, if the recipients of the founders shares (in the Delaware Corp) are Canadian, I believe that the Canadian rules are applicable and they have no immediate tax liability. BUT – they do not get a shot at the $835K Cap Gains exemption. Then, of course, there’s also the question of what is the FMV. If no capital has been raised, and if the company is brand new, I’d argue that the FMV is zero. Even for later stage issuances, I’ve not heard of CRA setting an FMV.
Thanks Mike! Again, great article – very informative.