Overlooked Opportunities of Equity Earners
- Garrett Stanley
- Mar 20, 2024
- 3 min read

Hello Friends!
This week we're looking at the top opportunities overlooked by those with equity compensation.
Let's jump in.
Embrace Diversification
Actively managing the balance between company stock and other investments, you can reduce risk while still capitalizing on the growth potential of your company shares. Diversification strategies might include setting rules for selling company stock at certain thresholds or investing in a mix of asset classes.
Align Concentrated Holdings with Wealth Goals
Periodically evaluating how concentrated stock positions fit within your broader wealth goals allows you to make informed decisions about rebalancing, such as when it's more advantageous to diversify holdings to mitigate risk or hold the positions for anticipated future growth. This kind of review ensures the investment strategies support long-term financial objectives.
Strategize Around Vesting
Paying close attention to vesting schedules allows for planning the exercise of options or the sale of shares in a way that aligns with market conditions, tax planning, and liquidity needs. Setting up a calendar of vesting dates and associated action plans can ensure opportunities are not missed. This proactive management can lead to strategic decisions about when to exercise options or sell shares, aligning with both market conditions and personal financial planning.
Plan for Liquidity
By anticipating needs for cash and planning sales of equity compensation in advance, you can better avoid the need to sell in unfavorable market conditions. Creating a liquidity plan that aligns with major life events (e.g., college tuition, home purchase, caring for aging parents) ensures that cash needs are met without disrupting long-term investment goals and strategies.
Leverage Proactive Tax Planning
Understanding the tax implications of different types of equity compensation can lead to strategic decisions that maximize take-home value while minimizing tax liabilities. A few examples:
Knowing when to exercise options or sell shares to optimize for capital gains tax rates instead of ordinary income tax rates can save significant amounts in taxes.
Some equity options, such as Incentive Stock Options (ISOs) are Alternative Minimum Tax (AMT) preference items. Planning liquidity needs with potential AMT in advance can inform decisions on when to exercise and sell.
Utilizing accounts with different tax treatments (e.g., Roth IRA vs. traditional IRA) for investments outside of equity compensation can further enhance tax efficiency.
Leverage Net Unrealized Appreciation (NUA)
In short, NUA strategies can significantly reduce your tax liabilities on company stock distributed from your 401(k) plans. This approach requires planning and timing but can optimize long-term capital gains and minimize ordinary income taxes, resulting in substantial savings.
Develop a Comprehensive Financial Plan
A well-rounded financial plan that includes considerations for personal goals, retirement, estate planning, investment goals, and risk management allows you to see the bigger picture of your financial health. This ensures decisions made in one area (e.g. investments or purchases) support overall financial goals, leading to better alignment on goals and effective wealth building.
Proactive Estate Planning
Early and ongoing estate planning ensures that wealth transfer and taxation are managed according to your wishes. While it isn't fun and may feel uncomfortable, not planning proactively leave large room for error. Tools like wills, trusts, and beneficiary designations can be tailored to your specific needs, providing peace of mind and avoiding potential legal complications.
Consider Comprehensive Wealth Management
Financial advisors, tax professionals, and estate planners provides access to expertise that can navigate the complexities of equity compensation and personal finance. These professionals can offer personalized advice, identify opportunities for growth, and help deliver better outcomes. For most, there isn't enough time in the day to get it all done and coordinated on your own.
Comprehensive wealth management services provide you with one designated professional who can plan and coordinate the other professionals on your behalf, freeing up your time and giving you a dedicated resource at all times.
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