Richard Friedman
NEW! All publicly traded companies face the risk that an executive or employee may violate corporate, tax, or securities law. This article series outlines practices for executives to help them avoid compliance problems, and explains the possible penalties of noncompliance. Part 2 presents issues involving foreign financial interests, nonresident state tax returns, retirement plan funding, company rules, and more.
Tom Davison and William Whitaker
NEW! "My income is around half a million dollars, and I'm paying the alternative minimum tax. It's annoying, and I feel trapped. Now what?" Surprisingly, the best move may be to increase income, and pay even more alternative minimum tax! Find out why by reading this intriguing article.
Andy Wagner
NEW! Having both nonqualified stock options and nonqualified deferred compensation gives you a tremendous amount of flexibility to optimize your financial planning and tax situation. In this article, I explain how I have used the two plans in concert with one another.
Michael Melbinger
NEW! Some significant tax and estate-planning opportunities—and traps—exist for foreign executives who come to the United States to work (and when they leave too). This article outlines the principal areas of concern.
Robert Gordon
A regulatory change in 2009 by the SEC now lets unexercised employee options act as collateral for listed publicly traded options. Learn about the rules, possibilities, and limits of this technique.
Chris Murphy
If the majority of your net worth lies in unexercised stock options or company stock, it may make sense to sell a portion to reduce the concentration risk while holding on to a portion to participate in future appreciation. However, if most financial goals can be reached without these proceeds and your position is not heavily concentrated, other strategies are worth exploring. One that is gaining popularity is writing call options on vested ESOs to generate some income.
Robert Gordon
Understand the key issues and limits of hedging NQSOs, including company, SEC, and tax law constraints. Then you can analyze potential hedging strategies for your stock options, such as collars.
Robert Gordon and Charlotte Lyman
Market volatility has made many high-net-worth executives want to hedge their exposure to concentrated positions in company stock. Unfortunately, most of the tools for hedging are not very efficient with NQSOs. Part 2 in this series examines alternative approaches.
Robert Gordon and Charlotte Lyman
Your company stock represents a large, concentrated portion of your wealth, making you nervous. You want to protect your gains and get your hands on some money.
Robert Gordon and Charlotte Lyman
After understanding hedging basics, you need to answer a few questions and decide whether your goals go beyond risk reduction to liquidity creation.
Robert Gordon and Charlotte Lyman
After learning the basic rules and restrictions, you now need to decide on the appropriate hedging tool and understand variable forwards and the final issues to consider in crafting your hedging strategy.
Mark Miller
For employees and executives, international travel and relocation are increasingly common. The taxation of "mobile employees" is always complex, and never more than with equity compensation. Part 1 introduces the key concepts and rules, including the sourcing and apportioning of income.
Mark Miller
International assignments or relocations can present attractive opportunities for career advancement. However, the taxation of equity compensation for mobile employees raises complex issues. Part 2 looks at specific scenarios, withholding taxes, and tax equalization.
Carol Cantrell
UPDATED! You may have employee stock options with a large spread but don't need the money, and you may want to defer the tax upon exercise as long as possible. But you also want to minimize your risk of owning a single stock. Learn about the possibility of substituting a nonqualified deferred compensation plan for your unexercised options.
Robert Gordon and Charlotte Lyman
Hedging stock from exercises of incentive stock options (ISOs) is complex, but it is possible in certain situations. Financial engineering can create a floor under the ISO stock while letting the capital gains holding period continue.
myStockOptions.com Editorial Staff & Contributors
UPDATED! Finding legal techniques to minimize taxes is almost as popular in the US as stock compensation. These sophisticated techniques with founder's stock and options can defer or reduce taxes.
myStockOptions.com Editorial Staff & Contributors
UPDATED! You want to defer gain on the sale of publicly traded securities, but they do not qualify as qualified small business (QSB) stock. Here's another way to defer tax on those holdings.
Stanley Trotta with Robert Gordon
With tax increases in mind, now may be a good time to re-evaluate your current financial-planning strategy for equity compensation and company stock holdings to determine whether action is required before new rates apply. Part 1 looks at nonqualified stock options.
The New York Times
This interactive article presents the compensation and wealth accumulation of the highest-paid CEOs. The figures, including the value of stock and options awards, are calculated from companies' proxy statements.
Megan Johnston
Financial Week
The IRS is targeting certain types of variable prepaid forward contracts, which some senior executives and founders with substantial company stock holdings have used to get cash for their shares without selling.
Geoffrey Colvin
Fortune
Next time you encounter a too-good-to-be-true strategy related to your company stock that greatly reduces taxes and puts money in your pocket, consider this tale of how the IRS caught up with many too-clever executives and charged them for tax evasion.
Alyn Ackermann
Financial Advisor
Executives with both concentrated positions in company stock and retention requirements need to understand the risks and strategies.
Internal Revenue Service
The IRS tips its hand on what its agents look for in audits related to all types of stock pay to ensure compliance, whether by corporations or executives.
Internal Revenue Service
This IRS manual summarizes the taxation of nonqualified deferred compensation, which can include certain types of equity awards, along with the hot spots for IRS review. For more about nonqualified deferred compensation, see
myNQDC.com, a sibling website to myStockOptions.com.
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Perhaps, depending on the structure of the plan. In general, the IRS wants to know about the foreign assets of US taxpayers to be sure taxes are paid on any earnings. There are two major reporting requirements for US taxpayers who have offshore holdings that qualify for disclosure...
Stock ownership guidelines specify how much company stock you must own in total or as a multiple of salary. Most companies count in the calculation the...
Although stock ownership guidelines are more common, retention mandates and requirements for CEOs and senior executives have become popular, as shown by survey data and corporate proxy statement disclosures. Supporters of share retention rules believe they show...
Yes, stock options and restricted stock can be granted to the directors on a company's board. Surveys by research and consulting firms show corporate trends in director stock compensation...
At some companies, international assignments are often accompanied by what is commonly called an equalization package. To give you an incentive to accept the international assignment, the company agrees to...
Yes, substantially. In addition, fluctuations of income, which can be caused by stock compensation, are a red flag that can trigger an audit. According to research...
A concentrated stock position occurs when a significant chunk of your net worth is tied up in a single stock. Strategies for hedging, diversification, and liquidity include...
Brokers are allowed by Regulation T of the Federal Reserve to lend up to 50% of a stock's market price on the day of the loan...
SEC Rule 10b5-1 provides a defense against charges of insider trading if you later trade stock while you know confidential, important information about your company. A Rule 10b5-1 trading plan is a program for the preset purchase and/or sale of your stock that meets the requirements of this SEC rule, including the need to...
Your estate-planning opportunities are more effective with company stock than with options. As a general rule, the contribution of the stock options themselves to a CRT is rather...
Most stock plans do not permit this for stock options or restricted stock during your life (i.e. transferable only at death), or they allow it only...
A clawback is triggered when you leave to work for a direct competitor or engage in...
Clawback provisions occur in company stock grant agreements, which tend to be not publicly available. However, a survey...
The exact tax impact is not always clear, especially when the repayment happens in the year after you recognized the income on your tax return, or if it occurs after taxes were withheld. You would...
At least for senior executives, you can find useful information. You can either go to the...
A number of tax law provisions that may affect your stock grants were introduced in the American Jobs Creation Act (AJCA); the final regulations on deferred compensation under IRC Section 409A, which adopt the...
It has become easier to sell call options on your vested employee stock options. This creates both an income-producing opportunity and a hedging strategy, if you are allowed to do this and you understand the risks...
Don't confuse restricted securities and restricted stock. They are very different...
You are in luck. SEC Rule 10b5-1 now provides an affirmative defense...
During any 401(k) blackout period, directors and executive officers...
Using a blind trust goes beyond the protections of Rule 10b5-1 plans, yet has more restrictions. These are irrevocable grantor trusts with...
The SEC's Division of Enforcement has been investigating executives' reporting of certain derivative securities transactions. When you enter into a hedging type of transaction, such as collars or prepaid variable forward contracts, you need to...
This depends on the approach you take. For most taxpayers, qualified dividends are taxed at a top rate of...
The put options you buy give you the right to sell the stock at a price you choose. With call options you are selling the right to someone else to "call away" the stock you own. The IRS ruled that the...
This depends on what triggers vesting. Section 162(m) of the tax code limits your company's deduction to $1 million unless a senior officer's compensation over this amount meets the performance-based exception. Stock grants are structured to meet this by...
This is a special feature included in a stock option at the time of grant. It provides for...
A reload encourages you to exercise the original stock options earlier than you otherwise might have. This lets you...
Under a limited number of stock plans, it used to be possible to defer delivery of shares, and related taxes, to some time after exercise or vesting. However, under Section 409A of the American Jobs Creation Act of 2004 (AJCA), this type of deferred compensation is...
Yes, but the arrangement must be carefully structured not to be considered a stock option or nonrecourse loan...
Yes. Section 16(a) of the Securities Exchange Act of 1934 provides that every person who is a director or executive officer (or a 10% beneficial owner) of a public company must file periodic reports of stock ownership with the SEC...
Having recoverable profits under Section 16(b) for a matching purchase or sale within six months does not mean that you will report the same amount as income for taxes. You calculate the profits under Section 16(b) differently...
To satisfy Rule 144, you must follow the resale rules for...
Be very careful, as IRS actions and new rules have essentially shut down the use of these techniques. Before recent developments, some tax planners advised...
Yes. Your intentions do not matter under the securities laws. You cannot...
Receiving deferred stock units, or RSUs that let you delay the delivery of shares (and thus taxes) at vesting, depends on...
Yes, but whether it applies to you depends on your income and net worth. Under IRC Section 877A, US citizens who relinquish their US citizenship, along with foreigners who are long-term tax residents (e.g. green-card holders) but end US residence, are subject to the exit tax if they meet certain conditions...
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CFP® Credit
Tax errors can be costly! Don't draw unwanted attention from the IRS. Our Tax Center explains and illustrates the tax rules for sales of company stock, W-2s, withholding, estimated taxes, AMT, and more.
Test your knowledge with our Financial Planning quiz.
Compliance Concerns That Executives Must Understand To Prevent SEC, IRS, And Corporate Problems (Part 2) 
