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4 Tax-Friendly Tips for Managing Company Stock Awards Thumbnail

4 Tax-Friendly Tips for Managing Company Stock Awards

Managing company stock awards is an important aspect of financial planning for executives. These awards have the potential to significantly boost earnings, but they require careful consideration and management to optimize their benefits and avoid potential tax liabilities.

In this guide, Dan Trumbower provides valuable tips to help you understand your options and make the best choices for your financial well-being.

Exercise Stock Options Strategically and Plan Ahead for Restricted Stock Units (RSUs) and Restricted Stock Awards (RSAs)

When it comes to company stock awards, executives commonly encounter three types: non-qualified (NQ), incentive stock options (ISO), and Restricted Stock Units/Awards (RSUs/RSAs). Each type offers unique advantages, underlying strategies, and tax considerations. Non-qualified and incentive stock options provide flexibility, allowing you to choose between exercising the shares or selling them to leverage the "spread" and potentially amplify gains based on the stock price.

On the other hand, RSUs/RSAs have no upfront costs and their value is determined by the prevailing stock price on the vesting date. Developing a sound strategy tailored to your goals, risk management, and tax optimization is crucial for successfully monetizing your stock awards. To navigate these complexities effectively, it's essential to collaborate with a Wealth Advisor who specializes in this area and work closely with your Certified Public Accountant (CPA) to anticipate any potential tax surprises.

Solutions for Managing Concentrated Stock Positions

Managing concentrated stock positions is another important consideration. While traditional diversification strategies like straight sales or "limit orders" can help spread out the risk, it's worth exploring other creative solutions as well.

  1. 10b5-1 Trading Plans: A highly recommended solution for key employees and corporate insiders is the implementation of a 10b5-1 Trading Plan. This plan allows you to schedule trades (such as shares or option exercises) in advance, providing protection against potential insider trading allegations for both you and your company. It can be implemented by anyone who does not possess material non-public information during an open trading window. To maximize the benefits of a 10b5-1 Trading Plan, it's advisable to develop a customized diversification strategy that takes into account company-specific guidelines.
  1. Net Unrealized Appreciation (NUA): Another avenue for diversifying company stock held within a workplace retirement plan is through Net Unrealized Appreciation (NUA). NUA represents the unrealized gains accrued over time, which is the difference between the current market value of employer stock and its cost basis. What makes NUA attractive is its unique tax treatment. The cost basis of the stock is taxed as ordinary income, while the NUA component is taxed at the long-term capital gains rate at the federal level. By utilizing NUA, you can even fulfill your first (and possibly second) Required Minimum Distributions (RMDs) with favorable tax treatment.
  1. Donor Advised Fund (DAF): If you have philanthropic inclinations, a Donor Advised Fund (DAF) presents a creative solution to diversify appreciated stock. Similar to a private foundation but with more flexibility and ease of establishment, a DAF allows you to contribute appreciated long-term securities during high-income years and receive a tax deduction in the year of the contributions. Additionally, you can grow your legacy by investing your contributions within the DAF and making grants to your chosen charitable organizations, both now and in the future.
  1. Borrowing Against the Position: As a client of Halpern Financial, you gain access to private lending channels through our institutional relationships. Borrowing against the value of your concentrated stock position offers immediate liquidity without the need to sell shares and potentially trigger taxable gains. This approach allows your portfolio, or specific stock position, to remain invested, utilizing those positions as collateral for liquidity.

Careful Financial Planning is Key

Effectively managing company-awarded stock holdings, exploring creative diversification solutions, and making strategic financial planning decisions require careful consideration.

However, with the right guidance and a well-thought-out approach, you can optimize your financial position as an executive, maximizing benefits while mitigating associated risks.

(Note: The information provided above is for general purposes only and should not be considered as financial or investment advice. Consult with a professional advisor for personalized guidance based on your specific circumstances.)

Daniel Trumbower

Senior Wealth Advisor