With wealth comes unique financial planning challenges. Learn how a financial advisor specializing in tax strategies for wealthy individuals and couples can help.
If you’ve accumulated considerable wealth throughout your lifetime, it’s common to have questions about how you can enjoy a comfortable retirement while leaving a legacy for your family and any charitable organizations you choose to support.
And among high net worth individuals and couples, taxes often rank among the greatest risks threatening your ability to preserve wealth and achieve your estate planning goals.
Smart Tax Planning Strategies for High Net Worth Individuals and Couples
In the Q&A below, you’ll gain insights from financial advisors who work with high net worth individuals and couples to help them implement smart tax planning strategies. With their expert guidance coordinated with professionals like accountants and estate planning attorneys, you can feel confident you’re taking the steps necessary today to preserve your wealth for the next generation and beyond.
Do you have questions not answered below? Use the form on this page to submit your questions, and we’ll update this article with answers from the financial professionals and educators in the Wealthtender community. You can also contact the financial advisors featured in this article directly to set up an introductory call or ask your questions by email.
Key Takeaways
The 2025 Tax Law Changes Permanently Reshape Planning for High Net Worth Individuals
The One Big Beautiful Bill Act, signed July 4, 2025, made TCJA rates permanent, raised the estate tax exemption to $15 million per individual ($30 million per couple), and increased the SALT deduction cap to $40,000 through 2029. If you haven’t revisited your financial plan since this legislation passed, now is the time to act.
Concentrated Stock Positions Carry Hidden Tax Liability That Demands a Proactive Strategy
When a single position represents a large share of your net worth, you face both company-specific volatility and a significant embedded capital gains tax bill. Strategies including charitable gifting of appreciated shares, systematic tax-year spreading, and Section 351 ETF exchanges each carry unique eligibility requirements — making specialist guidance essential before acting.
Year-Round Tax Planning Prevents the Costliest Mistakes High Earners Make
Bonus withholding gaps, missed estimated quarterly payments, IRMAA surcharges triggered by pre-Medicare income mismanagement, and poorly timed Roth conversions are among the most expensive — and preventable — tax errors for high net worth individuals. A proactive, year-round plan that incorporates HSA optimization, equity compensation timing, and Roth strategy can make the difference of thousands of dollars annually.
Are you looking for a financial advisor specializing in tax strategies to preserve your wealth?
You’ll likely find dozens of nearby financial advisors well-suited to help you reach your money goals with a personalized plan. But it may be more difficult to find a financial advisor specializing in tax planning strategies for high net worth individuals and couples.
Fortunately, many financial advisors offer virtual services so you can meet online no matter where you (or they) live. This means you can choose to hire a specialist financial advisor who lives hundreds of miles away if you decide their specialized knowledge and experience is a better fit to help with your unique financial planning needs.
In this article, we’ll introduce you to specialist financial advisors who you may want to contact to learn more about their services and how they can work with you to develop a personalized plan.
Resources to Help You Choose a Financial Advisor
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💸 Tax Strategies for High Net Worth Individuals and Couples
This page is organized into sections to help you quickly find the information you need and get answers to your questions:
- Q&A with Financial Advisors Specializing in Tax Strategies for Wealthy Individuals and Couples
- Get Answers to Your Questions About Tax Strategies to Preserve Your Wealth
- Browse Related Articles
Expert Answers: Tax Planning Strategies for High Net Worth Individuals and Couples
Six Questions on Tax Strategies for Wealthy Clients with Todd Stankiewicz, CMT®, CFP®, EA, ChFC®, ABFP™
We asked Harrison, NY-based financial advisor and tax planning specialist Todd Stankiewicz to answer six questions to help us understand the benefits of tax planning strategies for high net worth individuals and couples interested in preserving their wealth.
Q: Why do so many high earners end up with an unexpected tax bill on their bonus?
Todd: The IRS generally requires employers to withhold federal income tax on supplemental wages like bonuses at a flat 22%, but many high income earners fall into higher tax brackets. That gap can mean thousands of dollars in underwithholding that shows up as a surprise bill in April. The fix can be straightforward: we may adjust estimated quarterly payments or modify withholding to account for the difference throughout the year, so we minimize the chance of surprises. For clients with equity compensation, we also look carefully at the timing of vesting and exercises to manage stacking income into a single tax year.
Q: What should high-net-worth individuals know about the major tax law changes that just took effect?
Todd: The One Big Beautiful Bill Act, signed into law on July 4, 2025, introduced some of the most sweeping changes to the tax code in years. The TCJA tax rates are now permanent, which may provide greater certainty for planning. The estate tax exemption increased to $15 million per individual and $30 million per married couple for 2026 and beyond, which can be a meaningful shift for clients doing estate planning. The SALT deduction cap also moved to $40,000 for 2025 through 2029, subject to income limitations. If you have not revisited your plan since this passed, now is the time.
Q: What are the tax risks of holding too much of one stock, and what can I do about it?
Todd: Concentration risk and tax exposure go hand in hand. When a single position represents a large portion of your net worth, you face both the volatility of that company and a significant embedded tax liability if you sell. One simple but often overlooked move for clients who already make charitable donations: donate the appreciated stock directly instead of writing a check. You never recognize the gain, you still receive the full deduction at fair market value, and the charity receives the same amount. For larger positions, systematic selling spread across tax years and newer structures like Section 351 ETF exchanges are worth a serious conversation. Keep in mind, each of these strategies has its own unique eligibility criteria, risks and requirements to qualify. That is why it is so important you work with a professional that understands how to properly implement these strategies. These should not be implemented without consulting a qualified professional.
Q: When does a Roth conversion actually make sense for a high-net-worth individual?
Todd: Roth conversions tend work best when you can convert at a lower tax rate than you expect to pay in retirement, or when you want to pass assets tax-free to heirs. For high-net-worth clients, the window often opens in years where income dips, such as a gap between retirement and Social Security, a down year in business income, or a year with significant deductions. Converting strategically over several years, rather than all at once, keeps you from pushing into higher brackets unnecessarily. With SECURE 2.0 also eliminating required minimum distributions on Roth 401(k)s, the case for building Roth assets has gotten stronger.
Q: What tax mistakes do high-net-worth individuals make that their advisors should have caught?
Todd: The most common one we see is bonus and equity compensation hitting the wrong withholding rate and nobody adjusting for it during the year. A close second is missing quarterly estimated payments when business or investment income is unpredictable. For retirees, mismanaging income in the two years before Medicare enrollment can trigger IRMAA surcharges that add thousands in unexpected premiums. We also see business owners mixing personal and entity cash flow in ways that create avoidable tax exposure. Most of these are preventable with a plan that runs year-round, not just at tax time.
Q: Can high earners actually benefit from an HSA, or is it only useful for people with lower incomes?
Todd: HSAs can often be underutilized by high-income clients. The triple tax advantage is real: contributions are tax-deductible, growth is tax-free, and qualified withdrawals are tax-free when certain conditions are met. For clients who can afford to cover current medical expenses out of pocket, the more compelling strategy is often to leave the HSA invested and allow it to compound over time. There is no expiration on reimbursements, so receipts can be saved and used to take tax-free distributions years later. Eligibility starts with enrollment in a qualified high-deductible Health Plan, which is typically the first step in determining whether this strategy fits. Keep in mind that HSAs are most beneficial for those with high-deductible health plans and the ability to cover current expenses out of pocket because there can be penalties for non qualified withdrawals and the high-deductible health plans can require significant out of pocket cash to before insurance benefits kick in.
Advisory Services offered through SYKON Capital LLC, a registered investment advisor with the U.S. Securities and Exchange Commission. This material is intended for informational purposes only. It should not be construed as legal or tax advice and is not intended to replace the advice of a qualified attorney or tax advisor. The information contained in this presentation has been compiled from third party sources and is believed to be reliable as of the date of this report.
Certified Financial Planner Board of Standards, Inc. owns the CFP® certification mark, the CERTIFIED FINANCIAL PLANNER® certification mark, and the CFP® certification mark (with plaque design) logo in the United States, which it authorizes use of by individuals who successfully complete CFP Board’s initial and ongoing certification requirements. CMT Association owns the CMT® and Chartered Market Technician® marks.
Todd Stankiewicz, CFP®, ChFC®, CMT®, ABFP®, EA | SYKON Capital
Or visit his website to learn more.
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About the Author
Brian Thorp
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Brian and his wife live in Texas, enjoying the diversity of Houston and the vibrancy of Austin.
With over 25 years in the financial services industry, Brian is applying his experience and passion at Wealthtender to help more people enjoy life with less money stress.