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  • Where tax strategy meets real-world decisions.

    An independent publication delivering CPA-led insights

    on tax strategy, business growth, and wealth planning.

    757-384-9020

    Where tax strategy meets real-world decisions.


    An independent publication delivering CPA-led insight on tax strategy, business growth, 

    and wealth planning.

    Where tax strategy meets real-world decisions.
    An independent publication delivering CPA-led insight on tax strategy, business growth, and wealth planning.
    Where tax strategy meets real-world decisions
  • Where tax strategy meets real-world decisions.

    An independent publication delivering CPA-led insight on tax strategy, business growth, and wealth planning.


    • Tax Strategy & Planning
    • Business Growth & Advisory
    • Wealth Preservation & Legacy Planning
    • Business Transition & Exit Planning
    • Local Business Spotlights & Expert Interviews
    • Press Release
3 Minutes Read

The Collapse of Trust Protections: What Business Owners Must Know

Effective estate planning strategies ensure wealth protection under trust protection laws.


Understanding New Trust Laws: What They Mean for Your Family Wealth

For small business owners and military families in the greater Hampton Roads area, understanding the evolving landscape of trust law is crucial. Recent discussions at prominent estate planning conferences, such as the Heckerling Institute, reveal significant shifts that can affect how wealth is managed and passed down through generations.

In states across the U.S., regulations surrounding trust management have changed, leading to a concerning erosion of beneficiary protections. The consequences could be profound for families who depend on trusts to safeguard their assets and legacy.

What’s at Stake: The Dismantling of Beneficiary Protections

Trusts have long been a reliable option for wealthy families to manage their estates. However, recent legislative trends illustrate a rush to attract trust business, often sacrificing essential protections along the way. This competitive race has resulted in a series of laws that dismantle the “irreducible core” of fiduciary duties that trustees have historically owed to beneficiaries.

As highlighted in a prominent presentation, trustees may soon find themselves with less accountability for their actions. Families could become unaware of the existence of their trusts, leaving them vulnerable to mismanagement just when they need these legal structures most.

The Duty of Good Faith: A Fundamental Yet Fragile Trust

Historically, a trustee's duty to act in good faith has been sacrosanct. However, states such as Tennessee have begun to allow the exclusion of this fundamental obligation. This lack of accountability could drastically shift the power dynamics in family wealth management. Without a requirement for good faith, the potential for exploitation increases, raising alarms for families relying on their trusts for protection.

Consider the implications: if your trustee is not legally bound to operate with integrity, how can you ensure your family's interests are safeguarded against mismanagement?

Risky Business: The Rise of Exculpatory Clauses

Modern trust laws also enable the use of exculpatory clauses that prevent trustees from being held liable for nearly all non-fraudulent actions. Delaware's minimal restrictions mean a trustee could sidestep responsibility for gross negligence—all while families unknowingly place their trust in a potentially harmful framework.

This stark contrast to traditionally stringent jurisdictions, such as New York, underscores the necessity for families to re-evaluate their trust agreements. Simple actions like reviewing trust provisions could save them from detrimental losses.

Silent Trusts: When Ignorance Isn’t Bliss

The emergence of “silent trusts,” which keep beneficiaries in the dark about their interests, poses a significant challenge. In South Dakota, for example, trusts can remain silent indefinitely, allowing trustees to operate without any scrutiny. Families aiming for continuity can ironically end up disrupting the very legacy they seek to protect.

The implications for family businesses are particularly troubling. Without knowledge of their interests, future generations could lose connection and investment in family enterprises, undermining long-term sustainability.

Taking Proactive Steps: One Big Beautiful Bill Act of 2025

As the landscape shifts, estate planning strategies must evolve as well. The One Big Beautiful Bill Act (OBBBA) enacted a higher estate and gift tax exemption, presenting a unique opportunity for families. With these changes, ensuring your estate plan is flexible and responsive to current laws can maximize your family's wealth preservation.

For small business owners, this is a call to action: connect with local CPAs specializing in strategic tax planning to reassess your trusts and estate planning strategies in light of recent regulations.

Active Management of Your Wealth Strategy

It's essential for families to regularly revisit their estate plans to ensure they reflect the changing laws. By establishing a proactive tax strategy and planning framework, families in the Hampton Roads area can safeguard their legacies against these new vulnerabilities.

This may include exploring tools like Spousal Lifetime Access Trusts (SLATs) or Irrevocable Life Insurance Trusts (ILITs) that can provide both flexibility and protections aligned with your family’s needs. Consulting a qualified estate planning attorney can pave the way for a tailored approach that considers current and future laws.

Ultimately, as trust regulations become less reliant on beneficiary protections, it is fundamentally imperative to ensure your planning is sound. By staying informed and involving the right professionals, families can shield their wealth and ensure peace of mind for generations to come.


Wealth Preservation & Legacy Planning

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02.22.2026

Unlocking Wealth Transfer: The Strategic Benefits of Carried Interest Gifting for Small Business Owners

Update Why Carried Interest Gifting Has Become a Game Changer In recent years, estate planning for private equity and venture capital partners has seen a renaissance, driven largely by legislative shifts like the One Big Beautiful Bill Act (OBBBA). This significant change has solidified the federal estate and gift tax exemption levels. As a result, there's less pressure on small business owners and fund principals to act hastily when planning their estates. Instead, strategic thinking can now take the forefront of their planning efforts, especially when it comes to gifting strategies. Utilizing Gifting as a Strategic Tax Planning Tool Gifting carried interest presents a unique opportunity to strategically transfer wealth while keeping tax efficiency in mind. For many in the greater Hampton Roads area, particularly those with a background in military service or small business ownership, understanding the nuances of this approach is crucial. Gifting allows individuals to leverage assets that are currently undervalued yet hold potential for significant appreciation. Specifically, carried interest often faces value suppression during the early stages of investment funds. Early-stage carries are associated with high risk and uncertain cash flows, making their current market value lower. However, this low valuation translates into a tremendous opportunity because it allows for gifting at a lower tax basis. By transferring carried interest before its value appreciates significantly due to improved fund performance, business owners can effectively reduce their taxable estate while securing future growth for their beneficiaries. This proactive tax planning solution is critical for safeguarding wealth for the next generation. Understanding Carried Interest in Context Carried interest refers to the share of profits that investment fund managers receive, contingent upon favorable fund performance. This concept is often undervalued in a fund’s early years, making it a prime candidate for gifting. Here in Hampton Roads, where entrepreneurship thrives, especially among military affiliates, awareness of carried interest's characteristics can lead to optimized tax strategy and estate planning. A properly structured gifting strategy can ensure that high-growth potential assets are moved out of an individual’s estate before they fully appreciate in value. By gifting these interests, business owners not only reduce their estate tax liability but also secure a tax-efficient wealth transfer to their heirs. Assessing Risks and Opportunities in Gifting 1. Leveraging Market Conditions: In a fluctuating economic climate, market conditions can significantly impact the decision to gift. Early investments in technology or healthcare sectors, for example, may entail substantial risk but also exhibit impressive upside potential. Understanding the nature of these investments allows business owners to make informed decisions. 2. Engaging Professional Advisors: For those in the Hampton Roads community looking to navigate this complex terrain, working with a CPA or financial professional experienced in strategic tax planning is paramount. They can assist in valuing carried interests accurately, ensuring that the gifting process is executed in a manner that aligns with both tax obligations and personal financial goals. Final Thoughts: Transforming Wealth Across Generations In conclusion, the landscape of tax strategy and estate planning is evolving, and carried interest gifting is at the forefront of this change. By seizing the opportunities presented by the OBBBA to implement strategic gifting, small business owners in southeastern Virginia can ensure that their hard-earned wealth is preserved for future generations. Whether you operate a local business or have substantial investments in the community, embracing proactive tax strategies can provide lasting benefits. Actionable Insight: If you’re a small business owner or entrepreneur in the Hampton Roads area, now is the time to assess your estate planning strategies. Consult with a qualified financial advisor to explore how carried interest gifting can enhance your tax efficiency and secure your family’s financial future.

02.22.2026

Unlock Wealth Preservation: Why Picking the Right Trust Situs Matters

Update Understanding the Value of Trust Situs for Small Business Owners For small business owners, particularly those in the greater Hampton Roads area, the concept of trust situs might initially seem distant or irrelevant. Yet, for many entrepreneurs, understanding where to establish a trust can be critically important for ensuring long-term financial security. The Trust Landscape: A Closer Look at Key States In the U.S., several states stand out as leaders in favorable trust regulations: South Dakota, Nevada, Alaska, Delaware, and Wyoming. Each of these states offers unique benefits including asset protection, privacy, and tax advantages that can significantly impact wealth preservation strategies for families and businesses alike. South Dakota, in particular, has become a dominant player in trust administration, with the amount of trust assets growing from $165 billion in 2014 to over $800 billion today. The state has no state income tax on trust income, and it seals trust filings for automatic court privacy. For business owners in southeastern Virginia, these factors can be crucial when considering how to structure their estate plans to shield their assets from debts and litigation. Why Trust Duration Matters: The Perpetuity Factor The concept of perpetuity—the ability to keep a trust in effect indefinitely—can offer immense advantages. States like South Dakota and Alaska allow trusts to last for an astounding 1,000 years. This means that trust funds can be administered in a way that benefits multiple generations without the risk of sudden tax liabilities, such as those that might arise if a trust in states like California must be terminated within 21 years. For military families or those with substantial assets, establishing a long-lasting trust can be a way to ensure that their wealth remains intact, even as their family dynamics or financial landscapes evolve. Trusts as a Proactive Tax Strategy Trusts are not merely legal instruments; they can also serve as a powerful tax strategy. For small business owners, understanding how to leverage trusts can lead to significant tax savings. Implementing a trust in a low-tax jurisdiction allows business owners to retain more of their wealth while ensuring it is securely passed down to future generations. For instance, establishing a dynasty trust in Nevada (which allows 365-year trust durations) for business assets can protect against both income and estate taxes. Moreover, the structured approach of trusts can provide a clear framework for how assets are managed and distributed, which is particularly beneficial for families with diverse financial interests. Practical Insights for Small Business Owners So how can small business owners in the Hampton Roads area practically approach choosing a trust situs? Here are some actionable insights: Consult with Professionals: Given the complexity of trust laws across different states, working with a CPA or legal advisor who specializes in tax strategies for small businesses can provide clarity. They can help evaluate which state might be best for your specific situation. Evaluate Family Needs: Consider your long-term goals not just for business assets but also for family wealth preservation. A tailored estate plan that includes long-lasting trusts can mitigate potential risks associated with creditors or unforeseen circumstances. Remain Informed: Keep abreast of changes in tax policies and estate planning laws. The landscape is continually evolving, with states like Florida and Texas recently enhancing their trust legislation, potentially offering new opportunities. Building a Legacy: The Importance of Strategic Planning Ultimately, the importance of choosing the right trust situs cannot be overstated. As small business owners consider how to secure their assets for the long haul, strategic tax planning and thoughtful estate management become paramount. By establishing trusts in states offering favorable legislation, locals in the greater Hampton Roads area can ensure not just current wealth preservation but also set up a strong framework for future generations. Investing in knowledge and planning today can pave the way for enduring financial security across generations. Empower Your Future: Take Action Today Understanding the intricacies of tax strategy and planning is not just for the ultra-wealthy. Small business owners in southeastern Virginia should actively consider the benefits of trusts in their estate planning. Engaging a financial planner who understands these dynamics can lead you on a path to creating a robust financial legacy.

02.19.2026

Essential Insights on Tax Strategy: IRC Section 409A vs Gift Tax Valuations

Update Understanding the Distinction Between IRC Section 409A and Gift Tax Valuations The intricacies of estate planning can often leave both advisors and clients bewildered, particularly when it comes to the specifics of tax valuations. For small business owners in southeastern Virginia, particularly those navigating the complexities of estate and gift tax, understanding the distinction between IRC (Internal Revenue Code) Section 409A and gift tax valuations is crucial. The Essentials of Section 409A IRC Section 409A governs non-qualified deferred compensation plans, such as stock options and phantom stocks. A 409A valuation serves a specific purpose—establishing the current value of an employee's deferred compensation to help determine tax obligations. This valuation is primarily compliance-driven and does not equate to a fair market valuation in terms of gifts or estate planning. Gift Tax Valuations: What You Should Know On the other hand, gift tax valuations assess the value of transferred assets to determine how much tax a donor may owe on a gifted amount. These valuations must comply with IRS standards, notably outlined in revenue rulings that guide attorneys and CPAs in determining fair market value (FMV) for tax purposes. Why These Differences Matter Understanding these distinctions is fundamental for avoiding costly missteps. A 409A valuation might be inappropriate for gift tax purposes. For instance, while a 409A might indicate certain equity values, it’s not designed to incorporate factors like discounts for lack of control or marketability, which are crucial for gift tax assessments. As discussed in a comprehensive review by experts, failing to recognize these differences can lead to IRS adjustments, penalties, and even audit risks. Moreover, while 409A valuations maintain some level of audit immunity, gift tax valuations come with stricter scrutiny, potentially exposing clients to additional liabilities if the wrong assessments are made. Best Practices for Advisors For advisors working with small business owners, it's prudent to maintain clear guidelines when assessing valuations for estate and gift purposes. Establishing best practices can mitigate audit risks significantly. Always strive for a separate valuation that explicitly meets IRS guidelines for gift and estate tax filings, even if you already have a recent 409A report in hand. Future Implications on Tax Strategy and Planning As the IRS continues to evolve in its approach to equity compensation and estate tax audits, advisors must stay informed on potential changes. Integrating tactical tax planning into everyday business decisions not only prepares clients for the future but also fosters a proactive approach to minimizing liabilities. Planning strategies, such as year-round tax strategy consultations tailored for the unique circumstances of military families and business owners in the Hampton Roads metropolitan area, can lead to both financial security and compliance. Creating Custom Solutions for Small Business Owners The landscape of tax evaluations isn’t static; it requires a nuanced understanding of both current regulations and strategic foresight. Small business owners, especially in a complex market like southeastern Virginia, should leverage proactive tax planning services and consult experienced professionals to assess their unique needs effectively. In conclusion, small business owners need to grasp the distinct roles of IRC Section 409A and gift tax valuations, and the expertise of their advisors is paramount. Applying these insights not only aids in compliance but also enhances their overall financial health. For more tailored advice on navigating these valuation complexities, consider reaching out to financial professionals who specialize in strategic tax planning for small business owners.

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