Unveiling expert strategies for savvy tax planning with concentrated stock positions, this article distills the wisdom of financial gurus into actionable insights. It presents a range of options for optimizing tax implications, from charitable donations to strategic sales timing. Readers will find a trove of valuable advice to enhance their financial acumen without getting lost in complexity.
- Donate Appreciated Stock to a DAF
- Gift Appreciated Shares to Charity
- Spread Sales Over Multiple Tax Years
Donate Appreciated Stock to a DAF
Balancing the risk of holding concentrated stock with the tax consequences of selling is a common challenge we confront with clients, using a number of strategies.
Donor-Advised Fund (DAF) – We have clients donate highly appreciated stock to a charitable fund instead of cash. A DAF grants a charitable deduction while avoiding capital gains tax. The stock can be sold tax-free within the DAF and reinvested to align with the client’s philanthropic goals. We also have clients sell shares outside of the DAF while simultaneously front-loading several years’ worth of gifting to maximize the deduction.
Gifting to Friends or Family – When gifting stock to friends or family, the recipient assumes the cost basis. If they sell, they may owe capital gains tax. This works well if they’re in a lower tax bracket. For example, a child taking a gap year may qualify for the 0% capital gains rate.
Tax Bracket Management – Selling stock gradually can minimize the tax impact. We analyze a person’s projected tax brackets to effectively determine the timing and amount of sales, preventing unnecessary jumps to higher tax rates. We often aim to fill up the 15% capital gains bracket (up to $600,050 taxable income for Married Filing Jointly in 2025).
Tax-Loss Harvesting – By selling losing positions and replacing them with similar investments, investors can offset gains from concentrated stock sales, reducing taxes while maintaining market exposure.
Direct Indexing – This strategy builds a portfolio that tracks a market index while excluding the concentrated position, helping reduce risk. It also facilitates tax-loss harvesting, as individual securities can be sold strategically to generate tax benefits and offset gains.
Equity Compensation Planning – Many people end up with concentrated stock because they receive equity compensation. These stock plans bring a new set of tax considerations. I recently helped an individual prioritize his sales of company stock acquired via his 401(k), Restricted Stock Units (RSUs), and Non-Qualified Stock Options (NQSOs). The stock was a significant risk in his portfolio, but he felt overwhelmed by the different rules. We diversified his 401(k) without tax consequences, began selling new RSUs as they vested (minimal taxes on the sale), and began exercising the NQSOs closer to the vesting period to limit the ordinary income tax component.
Each strategy has its nuances, but with proper planning, you can diversify, reduce risk, and manage taxes effectively.
Matt Jude
Financial Advisor, Rebalance
Gift Appreciated Shares to Charity
When dealing with a concentrated stock position, the goal is to reduce tax liability while diversifying risk. One of the most effective strategies is to gift appreciated shares to a donor-advised fund or directly to a charity, which allows the donor to avoid capital gains tax and take a deduction for the full fair market value. For clients looking to retain some control, a Charitable Remainder Trust (CRT) can offer income for a set term while deferring taxes.
For those intending to sell, a structured selling plan under Rule 10b5-1 can help manage the sale over time, potentially optimizing for tax brackets and market conditions. Another tactic is tax-loss harvesting—pairing gains from the concentrated position with losses elsewhere in the portfolio to offset taxable income. In some cases, setting up a family limited partnership or a grantor retained annuity trust (GRAT) can help shift appreciation out of the estate, reducing both income and estate taxes over time. Each option requires careful coordination with legal and tax advisors to align with broader estate and financial goals.
Matthew Odgers
Estate Planning Attorney, Opelon LLP
Spread Sales Over Multiple Tax Years
When dealing with concentrated stock positions, tax planning is key to minimizing liabilities and maximizing returns. Spreading sales over multiple tax years can help manage Capital Gains Tax (CGT) by keeping gains within lower tax bands. Making use of the £3,000 CGT allowance (for 2024/25) is also a smart move, as this represents a reduction from previous years. Holding shares for at least two years before selling may qualify them for Business Asset Disposal Relief (formerly known as Entrepreneurs’ Relief), reducing CGT to 10% if they meet the eligibility criteria.
Gifting shares to a spouse or civil partner can defer CGT, as transfers between them are tax-free. Donating shares to a registered charity removes any CGT liability and may qualify for Income Tax relief. Using tax-efficient wrappers like ISAs or pensions when reinvesting proceeds can also reduce future tax exposure.
Additionally, considering an Enterprise Investment Scheme (EIS) or Venture Capital Trust (VCT) for reinvestment might provide further tax advantages for eligible investors. Given the complexity, seeking tailored financial advice ensures the best approach for your situation.
Kwin Santonil
Training & Quality Lead – Tax Preparation, Pie – The Self Assessment App
