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Strategic Wealth Management With Pre-Tax Retirement Accounts for HNW Families

Explore how high net worth individuals can optimize tax diversification across pre-tax retirement accounts and other savings to enhance lifetime wealth management and legacy planning.

Award-winning Financial Advising

Award-winning Financial Advising

Explore how high net worth individuals can optimize tax diversification across pre-tax retirement accounts and other savings to enhance lifetime wealth management and legacy planning.
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The Trouble With an All-Pre-Tax Retirement

For years, the standard retirement advice was simple: max out your traditional 401(k), take the upfront deduction, and let Uncle Sam wait to tax your Required Minimum Distributions (RMDs) in retirement. Watching your taxable income shrink on your W-2 can feel like an immediate win. But if you follow this path for decades, you may arrive at retirement with a less welcome discovery: a portfolio that is almost entirely pre-tax is not a nest egg so much as an income tax bill in waiting. On top of that, if your heirs are non-spouses, they’ll likely face the 10-year distribution rule on any pre-tax IRA they inherit, often during their own high-earning years.

Every dollar you pull from a traditional 401(k) or IRA is taxed as ordinary income. Once your RMDs begin in your mid-70s, the IRS no longer waits for permission. Those forced withdrawals can push you into a higher bracket, trigger Medicare’s IRMAA surcharges, and increase how much of your Social Security is taxed. Your goal shouldn’t be minimizing taxes in any single year but over your lifetime, and that could mean paying a bit more now to avoid paying far more later.

Because no one can reliably predict future tax brackets, markets, or policy, the more durable strategy is tax diversification: spreading your savings across three buckets with different tax treatments.

Tax-deferred accounts, such as traditional 401(k)s and IRAs, are funded pre-tax and grow tax-deferred, with withdrawals taxed as ordinary income later. Their advantage is straightforward: they boost your savings capacity during peak earning years by lowering your current tax bill. Taxable accounts, including individual and joint brokerage or trust accounts, are funded with your after-tax dollars and offer complete flexibility, since there are no early-withdrawal penalties and your heirs receive a step-up in cost basis. Tax-free accounts, namely Roth IRAs, Roth 401(k)s, and Health Savings Accounts, are also funded after-tax, but your growth and qualified withdrawals are entirely tax-free, your RMDs disappear, and your beneficiaries inherit the assets income-tax-free.

Holding all three creates flexibility that a single-bucket strategy can’t match. You can draw selectively from a pre-tax IRA during your low-income years, such as the stretch between retirement and claiming Social Security, filling up your lower brackets without spilling into higher ones. Large purchases become easier to fund efficiently too: pulling $100,000 entirely from a traditional IRA can trigger a meaningful tax hit, while blending the withdrawal across your Roth, taxable, and pre-tax accounts can keep your effective rate in check.

Tax diversification can positively impact your estate picture as well. If your non-spouse heirs inherit a traditional IRA, they’ll face the 10-year distribution rule, often during their own highest-earning years, while inherited Roth assets or stepped-up taxable accounts pass along a far cleaner legacy. This has been further compounded for heirs since the SECURE Act eliminated the “stretch IRA,” which once allowed beneficiaries to spread withdrawals, and taxes, across their own lifetimes.

If you’re still accumulating assets, your strategy may not require a dramatic overhaul. If you’re funneling everything into a pre-tax workplace plan, you might start directing a portion into a Roth 401(k) option, or build up a taxable brokerage account alongside it. If you’re a high earner phased out of direct Roth contributions, you can often still get there through a backdoor Roth IRA or a mega-backdoor conversion within your 401(k). It’s also worth mapping out your projected tax trajectory to identify windows, perhaps in early retirement before your RMDs and Social Security begin, when converting pre-tax balances to Roth at today’s known rates could save you considerably down the road. All of this works best as part of a broader decumulation plan that looks at your full balance sheet across your lifetime rather than one filing year at a time.

Tax laws shift, markets move, and no single formula fits every family. A personalized lifetime tax projection can show you how your current savings mix holds up under different scenarios, and where more balance might pay off. If you’re interested in this type of analysis, please reach out to your Wealth Manager.

The Trouble With an All-Pre-Tax Retirement
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Explore how high net worth individuals can optimize tax diversification across pre-tax retirement accounts and other savings to enhance lifetime wealth management and legacy planning.


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Testmonials

Testimonials provided by current clients of Robertson Stephens. Testimonials may not be representative of the experience of other customers and are no guarantee of future performance or success.

We have been clients of Michael Tierney for over 15 years. Michael stays well attuned to the various market issues and specifically follows strategists who have proven track records and philosophies. His frequent news emails have been especially helpful in keeping us informed of market happenings with his ongoing thoughts and educating us. On a more personal note, Michael has always been easily approachable, encouraging us to call anytime to answer questions or entertain ideas. There have also been personal business visits during which we appreciate Michael’s warmth and friendliness. His assistants through the years have also been very helpful in handling any necessary matters.

Client of over 15 years

After being introduced via trusted friends and neighbors, we have worked with Frank Corrado and team for over 10 years. The life transition we were facing was planning for our retirements. My husband and I have a seven-year age difference, so working with Frank, we established goals that reflected our greatest hopes for the future: paying off our mortgage by the time Sydney was 65, giving him financial freedom to return part-time to substitute teaching, while also helping me with a plan to retire from my full-time position in NYC when I turned 65. The mantra was always - how do we approach our portfolio in a way that allows us to sleep well at night and know that our savings will cover us for the remainder of our lives but would also allow for growth? Helping fund a grandchild's education, paying for two weddings, investing in the upkeep and upgrade of our beloved home of 30-plus years, ensuring plenty of funds to cover our love of travel, and devising strategic giving plans that supported our philanthropic goals were all reflected in our financial plan. Most importantly, Frank and his team are part of our family, committed to our well-being, going above and beyond to coordinate with our lawyer, insurance broker and even my mother's financial advisors! Frank believes in living your best life; he's committed to helping us ensure this is possible for our entire family.

Dana & Syd

Avi and his team have functioned as a private office for me, extending my capacities by managing my personal wealth and advising me on anything finance-related. Whenever I pose a question to them or ask them to handle a task, I know that it will be done promptly with consistent communication, the utmost skill, and great integrity. I could not have hired a better team. I don’t know what I would have done without Avi. When a sudden liquidity event completely transformed the scale of my wealth, Avi was there to help me navigate all of the new questions and opportunities. My prior wealth plan went out the window, and I had to make decisions about investing, taxes, estate lawyers, risk, charitable donations, supporting my family, and even personal security. Avi helped me navigate all those things, connecting me with the best possible advisors and giving me the support I needed to make informed decisions.

Client since 2019

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Questions
How does Robertson Stephens manage investments?

We build personalized portfolios based on your specific situation, including your risk tolerance, tax sensitivity, liquidity needs, and values. We use a disciplined approach that balances long-term growth strategies with short-term opportunities when they make sense. We continuously monitor your investments and adjust as needed, drawing on institutional-quality research and due diligence.

Can Robertson Stephens help me create a financial plan?

Yes. Every financial plan at Robertson Stephens is completely customized to you. Our advisors conduct an in-depth discovery process to understand your specific needs, goals, and concerns, then build a bespoke wealth plan tailored to your unique situation - covering everything from your risk profile to your tax sensitivity, liquidity needs, and even your personal values.

How does Robertson Stephens Wealth Managers get paid?

We work on a fee-based model, which means our compensation is tied to the assets we manage for you rather than commissions on products we sell. This aligns our interests with yours - when your portfolio grows, we do better too. The specific fee structure varies by client based on your situation and needs.


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