Multigenerational Wealth Transfer: Beyond the Basics
By Anne McCabe & Atricia Roberts
There's a question we often hear (sometimes whispered) after the technical part of a meeting wraps up. “How do I make sure my kids are ready for this?”
It rarely comes up first. Wills, trusts, and beneficiary forms tend to lead the conversation. But once the legal scaffolding is in place, the real worry surfaces. Will my children know what to do with what I leave behind? Will they understand the work it took to build? Will they be okay?
If you're a woman thinking seriously about generational wealth, especially one who has lived through a major life transition, you already know that money is rarely just about the numbers. You’ve seen what happens when families don't talk. You may have inherited something yourself and felt unprepared. You want better for the people you love.
That's the heart of multigenerational wealth transfer. The legal documents matter, but they're only one layer of the work.
Why “Beyond the Basics” Matters
A solid estate plan is the starting point, not the finish line. Most women we work with already have a will, a trust, beneficiaries on retirement accounts, and powers of attorney in place. If you don't yet have those in place, that's a good place to start. Those documents help safeguard your wishes and your family.
But sophisticated wealth transfer asks more of us than checking boxes on legal forms. It asks how, when, and to whom you want assets to flow; what you want those assets to do for the people receiving them; and what gets transferred alongside the money: values, expectations, judgment, and capability.
You've probably heard the saying “shirtsleeves to shirtsleeves in three generations.” Wealth rarely lasts on its own; preparation is what carries it forward.
The Conversation Gap
In our experience, the most overlooked piece of wealth transfer planning is the conversation itself. Many high-achieving women spent decades being private about money. Many were taught to be responsible with it, but not to talk about it openly. It wasn't discussed at the dinner table growing up, and it doesn't come naturally now.
The result is that adult children often inherit not just assets but surprises. They don't know what's coming, or what's expected of them when it does. They may not know whether the money is meant to support a lifestyle, fund a business, fuel a philanthropic vision, or simply be preserved.
You don't have to share a balance sheet to start the conversation. You can start with values. What does your family stand for? What do you hope your wealth makes possible, and what do you hope it doesn't enable? Conversations like these set the foundation for the technical decisions that follow.
Strategies to Know About
Once the foundation is in place, there are tools and strategies that go well beyond a basic will. A few that come up often in our work with clients:
Lifetime Gifting
The current federal lifetime gift and estate tax exemption is historically high, but it's scheduled to change. Strategic gifting during your lifetime, whether through outright gifts, 529 plans, or trusts, can transfer significant wealth tax-efficiently and let you see your gifts at work.
Trusts that Shield and Educate
A trust isn't only about control; well-designed trusts can shield assets from creditors, divorce, and poor decisions, while also creating structure that helps the next generation grow into the responsibility. Some families use staged distributions, others use incentive provisions, and others appoint co-trustees to teach by doing.
Roth Conversions As a Legacy Tool
For women in lower-income years, often after retirement and before required minimum distributions begin, Roth conversions can be a powerful way to pass tax-free assets to the next generation. The right window for this is narrower than most people realize, and it tends to close quickly.
Charitable Structures
Donor-advised funds, charitable remainder trusts, and qualified charitable distributions allow you to fold giving into your wealth transfer plan. They can also become a meaningful way to involve children and grandchildren in family decisions about generosity.
Step-up in Basis and the Capital Gains Trade-off
Sometimes the most tax-efficient strategy is the simplest one: hold appreciated assets until death, when heirs generally receive a step-up in basis. If you bought a stock years ago at $50,000 that's now worth $500,000, gifting it during your lifetime passes that low cost basis to the recipient, who will owe capital gains tax when they sell. Holding it until death typically resets the basis to the value at the date of death, which can erase years of built-in gains.
That trade-off is why we often recommend gifting cash or higher-basis assets during your lifetime and holding the most appreciated positions for step-up. The math doesn't always favor one approach. Your state of residence, your overall tax picture, and your family's needs all shift the answer, and that's where good planning earns its keep.
How You Title Assets
Wills and trusts get most of the attention in estate conversations, but how an asset is titled often does more of the actual work. Beneficiary designations on retirement accounts, life insurance, and annuities pass directly to the named person, regardless of what your will says. Transfer-on-death and pay-on-death designations on bank and brokerage accounts work the same way. Joint ownership shifts assets immediately at death.
Each of these mechanisms carries different tax and control consequences. A jointly held brokerage account passes outside probate but, in most states, only steps up half the basis at the first death (community property states allow a step-up on both halves). A revocable living trust keeps assets out of probate and allows for coordinated management if you become incapacitated. A beneficiary designation that hasn't been updated in 20 years can override an otherwise excellent estate plan.
Reviewing how every account is titled, and who is named on every beneficiary form, is one of the simplest ways to find expensive mistakes before they happen.
Educating the Next Generation
You can have the best plan in the world, and it can still fall apart if the people receiving the wealth aren't ready. This is one of the areas where we see women lead beautifully in their families. They tend to think about preparation, not just transfer.
Practical ways to prepare heirs include bringing adult children into a meeting with your advisor (with your permission and in your presence), writing a letter of wishes to accompany legal documents, and creating opportunities to practice. We've seen families give adult children a small investment account to manage, not because the dollars matter, but because the experience does. Some hold annual family meetings, while some pair gifts with conversations about what was hoped for and why.
Values Travel With the Money
Successful wealth transfers we've seen aren't just well-structured, they're well-explained. The next generation knows the story. They know what mattered to you, what you sacrificed for, and what you hope they'll do with the freedom you've worked to create.
That kind of clarity doesn't happen by accident. It comes from sitting down, often more than once, and being honest about what your wealth is meant to make possible.
How We Help
At Curo Private Wealth, we're women helping women navigate exactly these conversations. We coordinate with your estate attorney and CPA to verify the technical pieces are sound. We help you think through gifting strategies, trust structures, and tax planning. And we sit with you in the harder conversations: the ones about family dynamics, fairness across siblings, and how to talk to your kids about money.
More than an estate planning project, multigenerational wealth transfer is a relationship project, and it deserves the same care you'd bring to any other part of your life.
If you're ready to think beyond the basics, we'd love to help. Schedule a complimentary consultation or reach us at (301) 652-9677 or info@curoprivatewealth.com.
Frequently Asked Questions
What is multigenerational wealth transfer?
Multigenerational wealth transfer is the process of passing assets, values, and financial knowledge from one generation to the next, typically across at least three generations. It includes the legal documents (wills, trusts, beneficiary designations), the tax strategies (gifting, step-up in basis, charitable structures), and the conversations that prepare heirs to manage what they receive.
Why do most families lose generational wealth?
Most family wealth dissipates within three generations, a pattern often summarized as “shirtsleeves to shirtsleeves.” The reasons are usually less about poor investments and more about preparation: heirs who haven't been taught to manage significant wealth, families that don't talk openly about money, and estate plans that focus on legal documents without addressing values and family dynamics.
What is a step-up in basis?
A step-up in basis resets the cost basis of an inherited asset to its fair market value on the date of the original owner's death. This typically eliminates capital gains tax on appreciation that built up during the owner's lifetime. If you bought a stock at $50,000 and it's worth $500,000 at your death, your heirs' new cost basis becomes $500,000, and selling at that price would generate no capital gains tax.
What's the difference between a will and a trust?
A will directs how your assets are distributed after death and goes through probate, a court-supervised process that becomes part of the public record. A trust can hold and distribute assets without probate, can include conditions on how funds are used, and can take effect during your lifetime as well as at death. Most comprehensive estate plans use both.
Should I gift assets during my lifetime or leave them in my estate?
It depends on the asset's cost basis. Gifting appreciated assets during your lifetime passes your original cost basis to the recipient, who will owe capital gains tax when they sell. Assets passed at death generally receive a step-up in basis, which can erase those built-in gains. As a general rule, gift cash or higher-basis assets, and hold the most appreciated positions for step-up.
Do beneficiary designations override a will?
In most cases, yes. Retirement accounts, life insurance policies, annuities, and accounts with transfer-on-death designations pass directly to the named beneficiaries, regardless of what your will says. Reviewing those forms every few years, and especially after major life events like marriage, divorce, or a death in the family, is one of the most important things you can do.
Can my financial advisor work with my existing estate attorney?
At Curo Private Wealth, we collaborate: your attorney drafts the documents, and we help you think through the financial strategy, fund the trusts properly, coordinate with your CPA, and revisit the plan as your life changes.
About Atricia
Atricia Roberts is Chief Operating Officer and Partner at Curo, where she serves as lead advisor for Rockville clients and helps guide the firm’s growth and operations. With more than 15 years in financial services, Atricia is passionate about delivering human-centered financial planning and expanding access to comprehensive education for underserved communities. As a black female financial advisor and a member of the Association of African American Financial Advisors (Quad-A), she is dedicated to increasing the presence and success of Black professionals in the industry. A CFP® professional, she focuses on helping clients align their finances with their life goals. To learn more about Atricia, connect with her on LinkedIn.
About Anne
Anne McCabe is Chief Executive Officer and Partner of Curo Private Wealth, where she sets the firm’s vision and leads its advisory practice. With more than two decades in the industry, Anne’s career began on Wall Street before evolving into a mission to build a firm rooted in purpose, integrity, and values-driven advice. A CFP® professional, she is widely recognized for her leadership, mentorship, and commitment to lifelong learning. To learn more about Anne, connect with her on LinkedIn.