When Wealth Moves Sideways: What Horizontal Transfers Mean for Dropbox Households

'Dropbox employees should treat the first spouse’s death as a bracket stress test—model RMDs early, pace Roth conversions, engage both partners, and coordinate with tax and legal professionals before surprises hit.' — Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

'For Dropbox employees, charting how assets shift to a surviving spouse can reduce unexpected surprises. Talking to qualified tax and estate advisors can help.' — Brent Wolf, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

1. The horizontal transfer of wealth between spouses and its growing impact on estate planning for Dropbox families.

2. The tax implications of Required Minimum Distributions (RMDs) and strategic Roth conversions to manage income brackets and help preserve assets.

3. The evolving role of charitable giving and spousal financial engagement in shaping effective multi-generational legacy plans.

Major wealth transfers are anticipated over the coming decades. By 2045, more than $84 trillion is expected to change hands—$11.9 trillion to charities and $72.6 trillion to heirs and family members ¹ —and many of those dollars will first move “across” to surviving spouses rather than straight “down” to children.

Because women often live longer than men, a sizable share of assets may shift laterally to widows before any vertical bequests occur, a point stressed by Wealth Enhancement senior wealth advisor Mike Corgiat. This is important for Dropbox retirees with sizable IRAs to note. 

Pre-boomer generations are projected to pass $15.8 trillion in the next decade, while baby boomers may transfer nearly $53 trillion ¹ —frequently after the first spouse dies—illustrating how wealth rarely travels in a clean vertical line. 

This horizontal detour has real implications for required minimum distributions (RMDs), retirement savings, and estate tax exposure that can affect Dropbox employees late in retirement.

Current rules require RMDs to begin at age 73 for those born 1951–1959 and at 75 for those born in 1960 or later, and a surviving spouse can often roll an inherited IRA into their own to delay distributions—sometimes compressing taxable income into fewer years.

Brent Wolf, a retirement income planner with Wealth Enhancement, notes that once RMDs start and the survivor files as single, identical withdrawals can land in higher brackets—an issue that can surprise a survivor when income sources are already shifting.

Strategic Roth conversions while both spouses are alive—often in the 60s or early 70s—may help trim future RMDs and give the survivor more control, a tactic many Dropbox retirees may want to evaluate while they still benefit from joint tax brackets.

Corgiat emphasizes that conversions executed at comparatively lower rates can lessen the tax hit on both the survivor and heirs, while Wolf adds that thoughtful timing lowers the odds of large, forced taxable withdrawals later—key considerations for Dropbox employees eyeing estate efficiency.

Philanthropy is shifting too, as more affluent families embrace “living legacy” giving so they can witness impact, but a sudden asset windfall can delay or confuse charitable intent if the less-involved spouse isn’t already engaged in the broader plan. 

Wolf recommends that spouses who haven’t driven the finances start participating early, since many women may ultimately steer multimillion-dollar portfolios and will benefit from hands-on experience before the transfer moment arrives. 

Coordinated planning across tax, investment, and estate disciplines can answer pivotal questions for Dropbox retirees: How large might RMDs become with only one personal exemption? Would spreading Roth conversions over several years keep income in more favorable brackets? Are beneficiary designations current on retirement plans and insurance? Do charitable goals call for donor-advised funds, qualified charitable distributions (QCDs) from IRAs, or a family foundation? Has the estate been reviewed for credit shelter or portability strategies and potential federal or state estate taxes?

The death of the first spouse often triggers the most dramatic ownership and tax changes, so acting earlier—stress-testing single-life cash flows, harvesting gains or losses, accelerating withdrawals in low-income years, and reviewing insurance and titling—can materially influence outcomes for Dropbox retirees.

Those headline numbers—$84.4 trillion overall, $72.6 trillion to heirs, $11.9 trillion to charities—signal the size of what’s coming, but the net amount that actually arrives depends on how transfers occur and which tax rules apply, especially for families with layered benefits and investments.

As this horizontal phase of wealth transfer approaches, Dropbox employees may benefit by preparing actively to pass the baton to a suriving spouse.

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Analogy:  Picture a family’s wealth as a relay baton on an L-shaped track headed toward a $84.4 trillion finish line—$72.6 trillion earmarked for heirs and $11.9 trillion for charity—and the baton must first take a sideways turn between spouses, a reality many Dropbox couples will face before assets sprint down the straightaway to children and philanthropy.

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Sources:

1. Cerulli Associates. “ Cerulli Anticipates $84 Trillion in Wealth Transfers Through 2045 .' 20 Jan. 2022.

2. MassMutual. “ The horizontal wealth transfer: Redefining women’s wealth ,” by Shelley Gigante, 10 Mar. 2025.

3. MarketWatch. “ When a spouse dies, there can be a ‘tax explosion’ for the one left behind ,” by Beth Pinsker, 18 Jan. 2025.