ULTRA High Net Worth Tax Planning

Remember, with an almost $14 million Exemption, a married couple doesn’t face this issue unless they are north of $27 million. Now, take a client that is north of $50 million or $100 million, Estate and Gift Tax is king. And worse yet, at the end of 2025 that Exemption will drop to $7 million each ($14 million combined). The hottest thing in Estate Planning this year and next will be locking in the $14 million Exemption. I promise you that attorneys who don’t practice regularly with these higher net worth clients aren’t aware of these strategies. The old saying holds true— “they don’t know what they don’t know”!

“Multi-generational” Generation Skipping Trusts. This is one of the most complex topics in all of Estate Planning. The average attorney would have a difficult time explaining it, let alone knowing the rules. But, simply put, with GST Planning (“Generation Skipping Tax”), once a Trust is free of Estate Taxes to the client, it is free of Estate Taxes for the next 500 years or more as the kids, grand kids, and great grand kids use the financial benefits of the Trust without having the Estate Tax Liability when they die.

These clients tend to be business owners, or CEO’s of publicly traded companies, etc. They have huge capital gains issues when they go to sell and diversify these shares in the future. Most of these strategies have some form of a charitable component. A thorough understanding of Private Foundations, Charitable Remainder Trusts and Charitable Lead Trusts are crucial.

Practicing at this level is a definite “team approach,” requiring input from the clients’ CPA (Income Tax Advisor), Financial Advisor, Life Insurance Professional, and Trust Officer. So many of the complex issues can be solved only with combining different strategies and perspectives. The competition between the Estate Tax and Capital Gains Taxes as well as Income Tax strategies and solutions have to be carefully coordinated. What may be beneficial from an Estate Tax standpoint could be a huge mistake from an Income Tax standpoint.

In regular Estate Planning, more time is spent drafting documents than learning and understanding the strategies that apply to you. Practicing at a higher level involves much more time, maybe 3 or 4 times more, in the discussion and understanding of the many applicable strategies. It involves reading our articles and coming to the meetings prepared. And when you come to each “Estate Planning Session”, we will have flowcharts that clearly show how these strategies work. We will also have Excel spreadsheets that illustrate the Estate Tax Savings. But our biggest strength is our ability to explain complex Estate Tax strategies in easy-to-understand dialogue. Take a look at our articles and our videos and you will truly see that we are different. Before we draft any documents, we want to make sure that you understand each strategy that is available to you, the Estate Tax Savings, and the cost of implementation. Then you will be prepared to make solid decisions as to which strategies you want to implement. Normally it takes 3 to 5 sessions to understand these concepts. At the end of the sessions, we will provide you with a comprehensive Estate Planning Proposal that you can share with all of your advisors. We generally charge a flat fee to go through these sessions and prepare the Estate Planning Proposal.

Tier 3 clients are clients who have an Estate Tax problem, regardless of the size of their estate. Their net worth exceeds the Federal Estate Tax Exemption. With the 2025 sunset now in effect, that threshold is approximately $7 million for a single individual and $14 million for a married couple.

At this wealth level, the conversation is completely different at Dana Whiting Law. We are not focused on avoiding probate. We are focused on protecting your family from a very significant federal tax liability and on building a legacy that can last for generations. Tier 3 clients are also frequently looking to defer or eliminate Capital Gains on the sale of a business, appreciated stock, or substantial real estate holdings.

The key question when choosing an attorney is their tax training. Most attorneys who practice Estate Planning have very little tax training and experience. It all starts with the courses taken, and this is where having an LL.M. (Master of Laws in Taxation) is crucial. Other credentials, like being a CPA or holding an MBA, matter too.

Standard estate planning is largely focused on avoiding probate and distributing assets according to your wishes. Tier 3 planning is driven almost entirely by the Tax Code. It requires significantly more time upfront in discussion and design, not just drafting documents, and it demands careful coordination with a full team of professional advisors. The old saying holds true here: they don’t know what they don’t know.

Over the years, Dana Whiting Law has implemented estate plans for high-net-worth clients that will save their families hundreds of millions of dollars in Estate Taxes using the most cutting-edge strategies available. Common tools we utilize include:

• Family Limited Partnerships / LLCs for valuation discounts (the “Squeeze”)
• Installment Sales to Intentionally Defective Grantor Trusts (IDGTs) to freeze the growth of your taxable estate (the “Freeze”)
• Testamentary Charitable Lead Annuity Trusts (TCLATs) to zero out estate taxes at death (the “Washing Machine”)
• Stand-Alone Generation-Skipping Trusts to protect wealth across multiple generations
• Private Family Foundations and Charitable Remainder Trusts (CRTs) to balance philanthropic goals with tax mitigation
• Each strategy is selected based on your specific tax picture, your family’s dynamics, and your long-term goals.

Most business owners call their CPA or financial advisor first when a sale is on the horizon. That makes sense, but if an estate planning attorney with serious tax training is not at the table before the deal closes, you may be leaving millions of dollars behind permanently.

Once a sale is finalized, your options disappear. The window to implement strategies like Installment Sales to Intentionally Defective Grantor Trusts, Charitable Remainder Trusts, and Charitable Lead Trusts closes the moment the transaction is done. These tools can defer or in some cases eliminate a significant portion of the capital gains tax, but they have to be structured in advance.

Over the years, Dana Whiting Law has saved business owners millions of dollars in capital gains by getting involved before the sale closes. If a transaction is anywhere on your horizon, that conversation needs to happen now.

Generation-Skipping Trust planning is one of the most complex topics in all of Estate Planning. The average attorney would have a difficult time explaining it, let alone knowing all the rules. But once a Trust is properly structured and free of Estate Taxes for the initial client, it remains free of Estate Taxes for your children, grandchildren, and great-grandchildren, potentially for up to 500 years or more under state law.

Your family members enjoy the full financial benefits of the Trust without facing a new Estate Tax liability every time wealth passes to the next generation. For families at the Tier 3 level, this is one of the most important strategies we implement.

The process begins with a complimentary consultation and a simple two-page “Fact Finder” to understand your financial landscape and assign the right attorney. We do not charge for that initial meeting. We believe you should feel confident that we are the right fit before any engagement begins.

Because Tier 3 planning is complex, the design phase typically involves 3 to 5 strategic sessions. During these meetings, we use visual flowcharts and Excel spreadsheets to illustrate your estate tax exposure and the exact savings each strategy can generate. Your CPA and Financial Advisor are encouraged to attend the sessions that pertain to them. At the end of the process, we provide a comprehensive Estate Planning Proposal that you can share with all of your advisors.

We charge a flat fee to guide you through the comprehensive design sessions and prepare your Estate Planning Proposal. During that process, you will see the projected tax savings and understand the ongoing annual maintenance cost of every strategy on the table.

As Matt has said, “You are not paying for a stack of papers. You are paying for our experience, our advice, and our guidance in making key decisions.” Once you have decided which strategies make sense for your family, you will receive a flat-fee cost to draft and execute the specific trusts. Bundling multiple strategies together typically results in a lower per-trust cost.

Practicing at this level is a definite team approach. The competition between Estate Tax strategies, Capital Gains strategies, and Income Tax strategies has to be carefully coordinated. What works well from an Estate Tax standpoint can be a costly mistake from an Income Tax standpoint if no one is watching both sides of the equation at the same time.

Your estate planning attorney works directly with your CPA, Financial Advisor, Life Insurance Professional, and Trust Officer to make sure every strategy fits together correctly. At Dana Whiting Law, we want to be the quarterback of that team, your personal legal counsel and trusted advisor, not just for today, but for the generations that follow.