Publications
Gratitude and Thanksgiving
I share my ideas and knowledge as a gift to my greater community and readers to learn about the importance of planning and protecting your legacy. With four generations of experience, these issues are top of mind in our family. However, we are contacted by many who are unaware of the pitfalls of letting assets go to probate court or wasting most of the assets value in an estate on legal battles. My wish this holiday season is that you give your family and yourself the peace-of-mind that comes with clear communication and sound estate planning
Year-End Tax Planning 2025
The Game-Changing Tax Reforms You Need to Know before December 31, 2025 to save on your taxes. One Big Beautiful Bill Act (OBBBA), signed into law this past July, represents the most comprehensive federal tax reform since 2017. This year-end action plan provides deadlines for you to consider including tax analysis, investment portfolio review, charitable giving strategy, retirement plan funding, and making updates to your estate plan.
Matthew Erskine, JD Becomes a 2025 Fellow in the Family Firm Institute (FFI)
Matthew Erskine of Erskine & Erskine was announced and honored as a Fellow of the Family Firm Institute on October 30, 2025 at the FFI Global Conference in Boston, Massachusetts, USA. Fellow status signifies that Matt has completed an advanced program of study as part of the Family Firm Institute’s Global Education Network (GEN), presented at FFI annual conferences or published in FFI publications, and has been a member of FFI for more than 10 years. Fellow status is awarded to individuals who have achieved comprehensive professional knowledge and gained significant expertise that can be used as value to family enterprise members, including those with operating businesses and/or family offices.
How Wu-Tang Clan's Secret Album Just Revolutionized Art Law
Not just another intellectual property case. For the first time, a U.S. court has recognized that a creative work, when it’s worth depends on secrecy rather than mass distribution, can be protected as a trade secret. The implications for the art world are staggering. A precedent-setting decision by a New York federal court ruled that Wu-Tang Clan's single-copy album, Once Upon a Time in Shaolin, could qualify as a trade secret under the Defend Trade Secrets Act (DTSA). Traditional Copyright Law isn’t enough for today’s art market.
Integrating Art And Collectibles Into Holistic Planning
Ultra-high net worth (UHNW) clients face unique challenges due to the complexity of their wealth and family dynamics. Integrated, holistic approaches benefit both clients and advisors by addressing diverse needs, including the management of artwork and collectibles, and by fostering more effective, confident decision-making. integrated wealth planning isn't just beneficial—it's essential for today's ultra-high net worth clients who want to preserve, grow, and transfer their complete wealth legacy
For Want Of A Nail… Lessons From Besaw V. Commissioner On Charitable Deductions
For high-net-worth families and collectors, charitable giving can be a powerful estate and tax planning strategy. But as Besaw and similar cases make clear, failure to follow the rules can convert generosity into liability. The IRS and the courts demand precision, and Form 8283 is the roadmap. For want of a properly filled out and documented Form 8283, you will lose your charitable deduction for non-cash donations.
8 Business Valuation Mistakes And How To Avoid Them
Eight critical business valuation mistakes that could impact your legacy planning and wealth transfer strategies. Understanding common pitfalls is essential for high-net-worth individuals, family business owners, and their financial advisors as they navigate the intricate landscape of estate tax planning and business succession.
Estate Planning In World Of Watch Collecting
Collectors can more effectively navigate the complexities of integrating watches into their estate planning strategies and appreciating he intricate balance between the financial and emotional value of watch collecting and its impact on estate planning. Watches hold significant financial and sentimental value and may prove to be strong investments in the coming years. Understanding their role in an estate is crucial.
Planning for Older Clients and Those with Disabilities
Effective elder planning requires a comprehensive approach addressing immediate safety needs, long-term care funding and asset protection. A systematic approach includes Legal and Financial Foundations, Asset Protection and Long-Term Care Funding Strategies, and Care Coordination and Safety Planning.
How To Turn Downturns Into Generational Wealth
Ultra-high-net-worth families often face unique opportunities during periods of market decline, high inflation, or recessionary pressure. This white paper explores a range of advanced estate and gift tax planning techniques for such environments, focusing on family-owned businesses, art/collectibles, and legacy real estate – citing relevant Internal Revenue Code sections, IRS rulings, case law, and academic insights To tie together the above strategies, here are a few illustrative scenarios demonstrating how they can be applied for maximum advantage when markets are down.
The CTA: Compliance Reinstated With March 21, 2025 Filing Deadline
The recent court decision reinstating the CTA’s reporting obligations marks a significant development in corporate compliance requirements. With the March 21, 2025 deadline rapidly approaching, affected entities must act swiftly to meet their reporting obligations and avoid penalties. Given the complex nature of these requirements and the potential for future legal and legislative developments, seeking professional legal and compliance advice is highly recommended.
Entities can complete their BOI reports through the FinCEN portal here. Time is of the essence—act now to ensure compliance and avoid unnecessary legal and financial repercussions.
The Trump Administration’s Estate Planning Proposals
The Need For Proactive Estate Planning
While the Trump administration’s proposals have not yet been enacted, they signal a potential shift in how wealth transfer is taxed in the U.S. estate planners and their clients must stay informed and prepared to adjust their strategies based on legislative developments. Whether through permanent estate tax repeal, capital gains tax changes, or other tax reforms, the future of estate planning is evolving, requiring a proactive and flexible approach now, rather than in the last few weeks of 2025.
Should You Treat Your Family Business Investment Like You Treat Your Stock Portfolio?
Rather than viewing themselves as a single operating company family-owned businesses should take a page from asset management firms by adopting a structured, professionalized approach. They should think in terms of a portfolio of assets, managed with a focus on long-term sustainability. Some say family-owned businesses (FOBs)—where emotional ties, legacy, and control outweigh financial considerations. The wisest families, however, will do both—adapting where necessary while preserving the values that made their enterprise successful in the first place.
Court Blocks Corporate Transparency Act: A Win For Federalism?
The U.S. District Court for the Eastern District of Texas issued a nationwide preliminary injunction against the enforcement of the Corporate Transparency Act (CTA), questioning its constitutionality and its impact on small businesses. The CTA, enacted as part of broader anti-money laundering efforts, mandates companies to disclose their beneficial ownership information to a federal database maintained by the Financial Crimes Enforcement Network (FinCEN). The plaintiffs, including small business owners and a trade association, argued that the CTA compels speech and association, infringing on First Amendment protections. They also raised concerns about privacy violations under the Fourth Amendment, given the extensive personal information required.
Planning For The Unexpected Return: Lessons From Grubhub’s Founder
Why Do Founders Buy Back Their Businesses?Selling a company doesn't always mean closing the door for good. In some cases, owners find themselves wanting, or even needing, to regain control of the very businesses they once let go. From a planning perspective, it's critical to understand why owners might want to reclaim their former enterprises. While it may seem counterintuitive to want to buy back a company that was sold for a significant profit, there are many reasons why this occurs.
Navigating The Charitable Deduction Minefield: Insights From The IQ Holdings Case
As the landscape of charitable giving and tax planning becomes increasingly complex, adherence to IRS requirements is not just a recommendation but a necessity to safeguard against penalties and maximize tax benefits.
The IQ Holdings case highlights several critical requirements that taxpayers must meet to successfully claim charitable deductions under Section 170 of the Internal Revenue Code.
Are Deferred Sale Trusts A Tax-Efficient Way To Defer Capital Gains?
DSTs provide income deferral and asset control, but come with higher administrative costs, market risks and potential IRS scrutiny. CRTs and CLTs, in contrast, are highly tax-efficient for capital gains and estate planning purposes, especially for those with philanthropic goals. However, the irrevocable nature and charitable commitments can limit their applicability for those wishing to retain assets within their family.
Treasury’s 2024-2025 Priority Guidance Plan
The 2024-2025 Priority Guidance Plan signals an aligning tax policy with economic, social, and environmental priorities. It seeks to streamline tax administration, promote taxpayer compliance, and adapt tax regulations to evolving economic landscapes. By integrating public feedback and addressing emerging challenges, the Treasury and IRS aim to create a more responsive, resilient, and inclusive tax system.
Power of Attorney, Debt and Death: What you need to know
A power of attorney — POA, for short — isn’t a person or entity. Instead, it’s a legal document that passes decision-making power from one individual or entity to another. You can’t “be” a power of attorney. But you can attain it if an individual (the principal) authorizes you as an agent or attorney-in-fact. Learn about the types of POA and your responsibilities, as well as what debts don't belong to your acting as Power of Attorney.
Facing Estate Tax Challenges For Business Owners, Artists, And Gallery Owners
As 2024 progresses, the sunsetting of key tax provisions presents unique challenges for business owners, artists, art dealers, and gallery owners alike. With the estate tax exemption set to decrease and potential changes looming in capital gains and valuation practices, it is crucial to review and adapt estate and tax plans to avoid pitfalls.