How to Effectively Manage Capital Gains from Concentrated Stock Positions

If you’ve ever received stock options or shares as part of your equity compensation package, it may be tempting to concentrate your portfolio in your company’s stock. However, diversifying your investments is essential to mitigate risks and protect your wealth. In recent years, our wealth managers have seen employees from highly valued companies like Apple (AAPL) and NVIDIA (NVDA) reap significant rewards, with Apple’s stock price nearly doubling and NVIDIA’s increasing over fivefold in the past five years. These success stories certainly make these stocks attractive options for concentrated investments. It’s easy to see why employees would be excited and tempted to think the good times will never end.

However, holding a large amount of stock in a single company can be a double-edged sword. While the potential for profits is high, the risks are equally significant. Without diversification, your portfolio becomes vulnerable to the fluctuations of a single stock. Managing these concentrated stock positions and the associated capital gains is essential to protect your wealth and mitigate potential losses.

By understanding the risks and exploring strategic approaches, you can better protect your financial future. Let’s take a look at the dynamics of risk and reward, various strategies to manage your concentrated stock positions and practical tips for compliance, capital gains management and diversification. Whether you want to hold, hedge or donate your shares, we can help you explore your options.

Managing your stock concentration

Preserving accumulated wealth, particularly from executive compensation and price appreciation, can lead to significant family assets. While the rewards of concentrated positions can be substantial, they also expose your portfolio to considerable risk. To balance these rewards with potential risks, it’s crucial to diversify your investments and implement strategic approaches. Diversifying helps spread risk across different assets, ensuring you maintain control of your financial future.

Here are a few ways to manage your concentrated stock positions:

1. Holding period: Hold the investment long-term, ideally for more than one year, to qualify for lower long-term capital gains tax rates. This strategy allows investors to take advantage of the preferential tax treatment for long-term capital gains.
2. Tax-loss harvesting: This involves selling investments at a loss to offset capital gains from other investments, reducing overall tax liability. For example, if you have gains from NVDA but losses in another stock, selling the losing stock can help mitigate the taxes on your gains. Effective capital gains management is crucial for maintaining your wealth.
3. Gifting: For philanthropically inclined investors, donating appreciated shares to charitable organizations can also be tax-efficient. This approach allows investors to avoid paying capital gains taxes on the donated shares while potentially qualifying for a charitable deduction. Another option is to give a gift to a family member directly or through a trust, benefiting them if they are in a lower tax bracket. If the family member is younger, the gift may make sense from a time horizon standpoint and an after-tax standpoint if the younger family member is in a lower tax bracket.
4. Spreading capital gains: Instead of selling your entire position at once, gradually diversify your portfolio by selling a portion of your shares each year. This approach can help spread your capital gains over multiple tax years, potentially reducing the overall tax impact.
5. Hedging: Hedging strategies can be instrumental in managing risk associated with concentrated stock positions. Here are some common hedging techniques:
   • Options: Put options, which give you the right to sell your stock at a predetermined price, allow you to protect against downside risk. Alternatively, call options can generate additional income but come with the risk of selling your stock if it rises above the strike price.
   • Equity Collars: This strategy involves simultaneously buying put options and selling call options on the same stock. The put option limits downside risk, while the call option caps potential upside gains but provides premium income.
   • Exchange Funds: An exchange fund is an investment vehicle that allows investors to pool their concentrated stock positions into a diversified portfolio without triggering a taxable event. By contributing your concentrated stock to an exchange fund, you can diversify your holdings, reduce risk and maintain investment potential. These funds pool shares from multiple investors, providing a more balanced and diversified portfolio in return.
   • Prepaid Variable Forward Contracts: This complex strategy involves agreeing to sell a certain number of shares at a future date for a price determined today. It provides liquidity and downside protection while deferring capital gains taxes until the contract settles.
6. Charitable Remainder Trust (CRT): Investors who want an income stream from concentrated stock positions can create a Charitable Remainder Trust (CRT). The investor can transfer the concentrated stock positions into the CRT, have the CRT sell the assets, buy a basket of diversified investments, and then pay the investor a fixed percentage based on the fair value of the assets. Since the sale of the concentrated stock occurred in the CRT, the investor does not have to pay capital gains on the sale.

Strategic planning for long-term financial success

Effective planning is crucial for maximizing gains from concentrated investments while ensuring long-term financial health and stability. By seeking professional financial planning advice, you can confidently navigate the complexities of concentrated positions and work towards achieving your long-term financial goals. This guidance can provide reassurance and confidence in your financial decisions, especially regarding capital gains management.

Take control of your financial future and diversify your portfolio strategically with diversification strategies. Talk with an Aspiriant wealth manager to better understand how we can help you manage your concentrated stock positions and effectively handle your capital gains.