Recorded on 12/10/2025

Year-End Playbook: Navigating OBBBA Impacts and New Tax Opportunities

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This timely year-end conversation brought together Cresset’s tax team and RSM’s national specialists to discuss the One Big Beautiful Bill Act (OBBA) and outline planning considerations for families, founders, and investors as 2025 comes to a close and new rules begin to take effect in 2026.

Key Themes

OBBA Landscape and Timing Considerations
OBBA includes a wide range of provisions with varying effective dates, combining tax cuts and revenue raisers. As year-end deadlines converge, proactive modeling may help families evaluate differences between taking action in 2025 and waiting until 2026.

SALT Planning and Entity-Level Strategies
The SALT cap increased to $40,000 for certain taxpayers, though income-based phaseouts may limit its impact for many high earners. For eligible business owners, the pass-through entity tax (PTET) election continues to be a strategy to evaluate, particularly where entity-level deductions may result in different tax outcomes depending on individual circumstances and state rules.

Charitable Giving Under New Limitations
Beginning in 2026, charitable deductions may be reduced by a new floor and an overall itemized deduction limitation, potentially affecting the tax treatment of charitable giving. For philanthropic families, accelerating certain gifts into 2025 and coordinating with donor-advised funds may help address these changes, while qualified charitable distributions from IRAs remain a planning option under current rules and are not subject to the new constraints.

Estate, Gift, and Multigenerational Planning in a “Permanent” Era
OBBA increases the estate and gift exemption to $15 million per person in 2026, though future legislative changes remain possible. The discussion emphasized building flexible estate plans, confirming available exemption amounts based on prior gifts, weighing lifetime gifting against step-up considerations, and incorporating generation-skipping strategies where aligned with family goals.

Expanded Planning Considerations for QSBS and Opportunity Zones
OBBA introduces changes affecting Qualified Small Business Stock (QSBS) planning, including higher exclusion thresholds, partial exclusions at shorter holding periods, and broader eligibility based on company asset limits, while underscoring the importance of documentation and avoiding disqualifying transfers. The bill also includes updates to Qualified Opportunity Zones through ongoing designations and additional rural incentives, alongside increased compliance and reporting requirements that may influence implementation decisions.

About Amber Waldman

Amber is an estate and gift senior manager in RSM’s Washington National Tax practice. She spends most of her time serving ultra high net worth clients as an estate, gift, and generation-skipping transfer tax subject matter expert.

Amber has over ten years of experience in public accounting serving ultra high net worth families. She is passionate about helping clients accomplish their business, personal, and family planning goals by first listening to their concerns, and then creating well-thought-out tax strategies. She advises on a wide spectrum of tax matters, including generation-skipping transfer tax remedies, adequate disclosure and proper gift tax reporting, estate and gift special valuation issues, and income tax ramifications of estate planning decisions. Amber has authored thought leadership published in The Tax Adviser, Bloomberg Tax, Probate & Property Magazine, and Houston Business Journal.Amber is mom to a playful preschooler and enjoys baking, hiking with her two dogs, and listening to Ingrid Michaelson. She plays the ukulele which she learned when she taught preschool creative movement and music classes prior to her career in accounting.

About John Charin

John Charin is a Senior Manager in RSM’s Washington National Tax office with a focus on accounting methods and periods. John is the technical lead for the real estate industry group, and in this role provides tax advice and client services, as well as preparing and delivering
professional education for other lawyers and accountants. John regularly publishes on OBBBA's impact on real estate and provides VIP client services and tax law briefings to real estate clients.

In his current role, John advises and consults on complex tax matters, assists engagement teams in research and planning, and provides technical oversight on accounting method changes and IRS filings. John is a subject matter expert on leasing transactions, like-kind exchange and involuntary conversions, casualty and disaster events.

John currently serves as Vice Chair of the American Bar Association's Capital Recovery and Leasing Committee, and routinely moderates or participates on ABA panels for several committees as a tax technical expert. John is a lifetime resident of the Washington, D.C. area, where he can usually be found pushing a stroller around the National Zoo or other Smithsonian museums.

About Matt Talcoff

Matt is the leader of RSM’s Washington National Tax practice and a member of the Firm’s Board of Directors. He also is a member of RSM’s national tax leadership team and works with the firm’s tax policy and legislative services teams. Matt was previously RSM’s national tax industry Leader.
Matt has assisted middle market clients, many of which are globally active and high net worth individuals, with tax planning and compliance services for more than 30 years. He primarily works with privately held and private-equity-owned middle market businesses and their owners, as well as financial fund executives and family offices. He serves clients across a broad range of industries, with a focus on the consumer product industry’s restaurant, retail, and food and beverage sectors, as well as the financial services industry.

Matt leads RSM’s Washington National Tax practice, which features the firm’s most technical tax resources, and ensures our clients benefit from that knowledge. Matt also coordinates and supports the firm’s commitment to serving middle market clients by ensuring an industry approach is embedded in RSM’s efforts to provide an unmatched client experience. He works with the firm’s national industry and national tax leadership to ensure alignment of strategic efforts. He also assists the firm’s private client services leadership team on global initiatives, as well as initiatives related to fund executives and family offices.

Matt joined RSM in 2008 following 17 years at a Big Four firm. He frequently speaks and writes about private client and consumer products tax matters that affect business owners and their businesses. Matt speaks on tax policy and matters on Capitol Hill and at industry association conferences. His speaking engagements have included the ICR Retail Investment Conference, National Restaurant Association, Franchise Times, American Apparel and Footwear Association on topics including the effects of tax reform on retail and restaurant businesses and owners. He has spoken at PrivCap events about tax planning for fund executives.

About Nick Gruidl

Nick is experienced in working with publicly and privately held businesses. He focuses on advising clients and firm personnel on corporate merger and acquisition activity; spin-offs, bankruptcy and debt restructuring; private equity transactions; consolidated group issues; analysis of net operating loss issues; and partnership taxation. Nick develops and delivers internal and external training on corporate tax and transaction-related issues.

Cresset refers to Cresset Capital Management, LLC and its respective direct and indirect subsidiaries and controlled affiliates. Cresset Asset Management, LLC, also conducts advisory business under the names of Cresset Sports & Entertainment, CH Investment Partners, and Cresset Capital. Cresset provides investment advisory, family office, and other services to individuals, families, and institutional clients. Cresset also provides investment advisory services to investment vehicles investing in private equity, real estate, and other investment opportunities. Cresset Asset Management, LLC and Monticello Associates, LLC are SEC registered investment advisers. SEC registration does not imply any specific level of skill or training.

*Third-party prepared biographies are provided for informational purposes only; Cresset does not validate their accuracy or completeness.

Featuring

Amber Waldman

Amber Waldman

Senior Manager, Washington National Tax, RSM
John Charin

John Charin

Senior Manager, Washington National Tax, RSM
Matt Talcoff

Matt Talcoff

Partner, Washington National Tax, RSM
Nick Gruidl

Nick Gruidl

Partner, RSM

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