I help high-net-worth families create coordinated, tax-efficient estate plans that grow and adapt with them.

My practice focuses on families with significant assets, multiple state residences, and sophisticated estate and income tax considerations. These families often find that a standard estate plan no longer fits their needs.

As both an estate planning attorney and a CPA, with two advanced degrees in taxation, I approach planning through an integrated lens, considering legal structure, tax consequences, asset ownership, and long-term family objectives together rather than in isolation.

I regularly work with families who:

•	Have $5 million or more in total assets
•	Own real estate in multiple states
•	Have existing estate plans, including irrevocable trusts
•	Are concerned about estate tax exposure, income tax efficiency, or both
•	Have growing wealth, business interests, or evolving family dynamics

Rather than focusing solely on drafting documents, my work emphasizes a structured planning process that can be summarized in three phases:

     1. Design – Clarifying goals, family considerations, asset structure, and tax exposure

     2. Build – Creating estate plans that coordinate legal and tax-aware solutions

     3. Maintain – Reviewing and adapting plans as laws, assets, and family circumstances change over time

Much of my work involves reviewing existing planning documents that are technically “complete,” yet fail due to lack of coordination, outdated assumptions, or changes in wealth or residency. Others engage me before planning begins, seeking a thoughtful and disciplined approach from the outset.

I work closely with clients’ other advisors (including CPAs, financial advisors, and trustees) to ensure alignment between a client’s estate plan, business plan, and overall financial plan.

A pattern I see when meeting with wealthy families is this:


A family builds significant wealth, and only then begins thinking about estate taxes.

The instinct makes sense.
-When wealth is growing, the focus is on building, reinvesting, and expanding.      
-Planning for a transfer often feels premature in your 40s and 50s.
-For some reason, talking about "death and taxes" seems a lot less fun than basically anything else 

The challenge is that timing matters.

Many of the most effective estate tax strategies work best during the growth phase, when asset values are lower, appreciation is still ahead, and flexibility is greater.

By the time a $60 million estate is already built, trying to fit it within a $30 million exemption can feel like an elephant playing the limbo dance. The options become narrower. The tradeoffs become heavier.

Contrast that with planning when the estate is $20 million and growing toward $60 million. At that stage, it’s often possible to structure things in a way that allows future appreciation to occur outside the taxable estate entirely.

The difference isn’t intelligence.
 It isn’t sophistication.
 It’s timing.

Estate planning is rarely about reacting to wealth after it arrives.

It’s about positioning growth before it compounds.

Samuel DiPietro

Helping High-Net-Worth Families Design, Build, and Maintain Coordinated, Tax-Efficient Estate Plans.

Last week, I sat for the California bar exam.

It has been five years since I last took a bar exam (Illinois), and I’m hopeful this will be the final one.

For the past three months, my schedule has been: work from 6:00 a.m. to noon, study from noon to 5:00 p.m., repeat. It felt like every other email I sent began with, “Thank you for your patience…”

Balancing client work with exam preparation is a reminder that discipline is mostly routine, repetition, and showing up on days when you’d rather not.

I’m grateful to the clients and colleagues who extended patience during this marathon. 

If all goes well, I’m looking forward to not seeing another bar prep outline for a very long time

Samuel DiPietro, JD, CPA, LLM, MST

A concerning trend I’ve been seeing lately:

Clients walk in with irrevocable trusts they don’t fully understand.

The documents are signed. The trust is funded. The structure looks sophisticated.

But when I ask simple operational questions:

-How are distributions documented?

-Are beneficiaries aware of the trust?

-Are notice requirements being followed?

-Is anyone tracking the standards outlined in the agreement?

I’m often met with silence.

Here’s the uncomfortable reality:

An irrevocable trust is not just a document setting "guidelines". It’s a system with rules. And like any system, it only works if it’s operated according to its rules.

Distribution standards, notice requirements, trustee procedures, these aren’t recommendations. They’re the very provisions that support the tax treatment and creditor protection the trust was designed to achieve.

If those rules aren’t followed, the benefits can erode.

Trusts are powerful vehicles for transferring wealth across generations. But like any vehicle, you have to understand the controls and follow the maintenance schedule if you expect it to perform as designed.

That’s why my process begins with a Design Phase.

Before making changes or creating anything new we take existing documents and translate them into plain English. We clarify what is required, what is optional, and what is currently not being done. Most importantly, we discuss why each requirement exists.

Because sophistication without understanding isn’t protection.

Clarity is

One of the most common misconceptions I see is this:

“I have a revocable trust, so I’m probate-proof.”

Often, the client is right about one thing: they do have a revocable trust.

But when we look closer:

-The primary residence isn’t titled in the name of the trust.

-The business interests are still owned individually.

-The vehicles are outside the trust.

-The vacation property was never transferred.

The document exists but the funding was never carried out.

A revocable trust can be an excellent probate-avoidance tool. But the trust only controls what it owns. If assets remain outside of it, probate may still be required for those assets.

An unfunded revocable trust isn’t probate protection. It’s a well-drafted document waiting to be used.

This isn’t a failure of sophistication. It’s usually a breakdown in follow-through. Funding is the step that often gets overlooked because it feels administrative rather than strategic.

But funding is what turns intention into reality.

Estate planning isn’t just about signing documents.
It’s about making sure ownership aligns with the plan.

Because probate avoidance doesn’t happen automatically.

It happens when the details are completed.

What two semesters of teaching estate planning to undergraduates from 7:00 a.m. to 9:00 a.m. taught me about working with clients.

As estate planning attorneys, we love our acronyms: NINGS, DINGS, and just about anything that contains the phrase “intentionally defective.”
But for many clients, those terms might as well be a lost language from the Rosetta Stone.

Teaching red-eyed undergraduates at the crack of dawn made that reality impossible to ignore. You can know the material cold, but if you can’t translate it into something your audience understands, the message doesn’t land.

That experience reinforced something I believe strongly about estate planning: part of the attorney’s job, much like a professor’s, is not just mastering complexity, but breaking it down into plain English.

Clients don’t need to memorize acronyms. They need to understand the goal we’re trying to accomplish, the tradeoffs involved, and why a particular structure fits their situation.

If a client walks away nodding along but not truly understanding, the plan may be sophisticated, but it isn’t successful.

One of the quiet struggles I see in affluent families has nothing to do with tax laws. The struggle is a conversation.

Many families assume their children “don’t really know” there is significant wealth.

But when you grow up in a 10,000-square-foot home, fly private, or spend summers in different states, the existence of wealth is not a mystery.

Children may not know the number. But they know the lifestyle.

The real issue isn’t whether the next generation is aware of the wealth.
It’s whether they are prepared to handle it.

There’s a quote I often return to:

“Families spend years preparing the wealth for the family, but far less time preparing the family for the wealth.”

Estate planning documents can transfer assets. They cannot transfer judgment, discipline, or shared values.

That requires conversation.

-What is the purpose of the wealth?

-What responsibilities come with it?

-What expectations exist around stewardship?

-How should decisions be made?

Avoiding the conversation doesn’t preserve innocence.
It often just delays confusion.

Transferring wealth is technical.
Transferring readiness is intentional.

And in many cases, the second is far more important than the first.

Over the past six months, I’ve seen a dramatic increase in clients asking about LLCs formed in so-called “privacy jurisdictions” like Wyoming and South Dakota.

There’s nothing inherently wrong with those jurisdictions. Privacy-focused entities absolutely have their place in a well-structured estate plan.

The concern is how they’re being marketed.

Recently, a client forwarded me a solicitation offering an “asset protection plan” involving the creation of more than 20 Wyoming LLCs at a “flash sale” price north of $60,000.

Twenty LLCs... the pitch wasn’t really about privacy. It was about being “creditor proof.”

Here’s the reality: forming an LLC in a privacy-friendly state does not magically shield assets from creditors in your home state. If you own Arizona real estate and face an Arizona creditor, creating layers of single-member LLCs does not change the result.

Structure matters but substance matters more.

If it seems too good to be true, it usually is.

Privacy LLCs can be useful tools when:

-There is a legitimate privacy objective

-The structure aligns with the client’s actual risk profile

-The entity is properly formed and operated

But entity window dressing does not equal protection. It often just means more fees and more administrative burden.

Good planning is intentional.
Not promotional.

When clients are facing potential estate tax exposure, I often describe the challenge this way:

You’re not fighting paperwork.

You’re fighting math.

And like any battle, you need the right tools.

There are three primary “weapons” we use when planning against the estate tax:

1. Freeze:
Slow the growth of the taxable estate by shifting future appreciation outside of it. The goal isn’t necessarily to move everything today—it’s to prevent tomorrow’s growth from compounding inside the estate.

2. Discount:
Transfer assets in a manner that allows more value to move than exemption consumed. In simple terms, use $1 of exemption to move more than $1 of economic value.

3. Burn:
Intentionally reduce the taxable estate over time. This might involve annual gifting or strategies where the client pays income taxes on assets that are growing outside the estate.

Each of these strategies can be powerful.

But they share something in common: They require time.

Estate tax planning works best when done during the growth phase, not after the estate has already expanded beyond the exemption. Once the numbers are large, the math becomes tighter, and the flexibility narrows.

The most important decision isn’t which strategy is the most sophisticated.

It’s starting early enough to choose intentionally.

Because when it comes to estate tax planning, time is often a client's most valuable ally.

A common asset protection misunderstanding I see is this:


“I have an LLC, so I’m protected.”

I recently met with a first-generation business owner who believed exactly that. He had taken the important first step of forming an LLC. On paper, the entity existed.

But when we looked closer:

-Customer payments were deposited into his personal bank account.

-The business insurance policies were in his individual name.

-There was no operating agreement.

The structure existed, but the substance did not.

Courts don’t just look at whether an entity was formed. They look at whether it was respected. If the business owner treats the LLC like an extension of themselves, a court may do the same.

That’s where real risk emerges.

Asset protection isn’t about filing formation documents. It’s about operating consistently with the structure you created.

An LLC can be a powerful tool, but only if it functions like a real business:

-Separate accounts

-Proper documentation

-Clear agreements

-Consistent formalities

Creating an entity is step one. Running it properly is what lets the entity hold up in court. 

In asset protection, details aren’t technicalities.
They’re the difference between protection and exposure.

I have a 30 to 40 minute commute home from the office.

It does not bother me. In fact, I value it.

It gives me uninterrupted time to listen to audiobooks and continuing legal education. For example, recently, I was listening to a lecture series on ancient Roman history. The professor made a comment that I really took to heart:


“When I began my career in my late twenties, I felt I knew almost everything about Roman history. In my forties, I would say I knew most but not all things about Roman history. Now in my seventies, let me tell you… I know very little about Roman history.”


That progression resonated deeply. While I still have a number of decades before I reach my seventies, I have found the same phenomenon to be true in my own practice.


The more I study and learn estate planning and taxation, the more I realize how much depth there truly is. The Internal Revenue Code has been around for generations, yet its interaction with state law, evolving regulations, valuation principles, and family dynamics creates layers of complexity that cannot be mastered casually.

That realization has not discouraged me. It has refined my practice.

It has led me to narrow my focus to families and business owners whose planning involves meaningful complexity:

-Families with large or potentially taxable estates

-Clients with a presence in multiple states such as Arizona, Washington, Colorado, and Oregon where state tax regimes and property systems intersect

-Business owners and clients with significant commercial real estate holdings

Complex planning demands humility and continuous learning; combined with a willingness to acknowledge that there is always more beneath the surface.



The longer I practice, the more I appreciate that depth and the more I narrow my focus.

I had a long conversation with a potential client yesterday about the intersection of estate planning and income tax planning.

Specifically, we were discussing the step-up in basis that occurs at death and how that interacts with ownership of an S-Corporation. The conversation focused on the relationship between the shareholder’s outside basis and the entity’s inside basis, and how thoughtful planning can significantly affect the tax efficiency of a business sale after the owner’s death.

These types of conversations are a good reminder that estate planning does not exist in a vacuum.

A well-drafted trust may control who receives the assets, but understanding the tax consequences determines what those assets are actually worth when they are transferred or sold.

For business owners in particular, the coordination between estate planning and income tax planning can make a substantial difference for the next generation.

It’s not enough to simply be good at drafting trusts.

The real value comes from understanding how legal structure, tax basis, and long-term tax planning work together.

Because the best estate plan isn’t just about transferring assets. It’s about transferring them efficiently.

For clients living in states with their own estate tax, planning can feel like ballet dancing in a minefield.

Every step matters.

You’re trying to:

-Maximize a much smaller state estate tax exemption

-Preserve a stepped-up basis for income tax purposes

-Ensure the surviving spouse has sufficient liquidity

-Avoid building something so complex the family can’t realistically administer it

Move too aggressively and you may sacrifice income tax benefits.
Move too cautiously and you may leave unnecessary estate tax exposure.
Add too much structure and you create administrative friction.

This is where estate planning stops being about forms and starts being about judgment.

It’s more than sending a questionnaire asking for fiduciary names and addresses. It requires modeling scenarios, stress-testing assumptions, and sometimes opening Excel to see how different structures actually perform under various outcomes.

Because state-level estate tax planning isn’t just about avoiding tax.

It’s about balancing competing objectives:

-Tax efficiency

-Liquidity

-Simplicity

-Long-term sustainability

Good planning doesn’t eliminate tradeoffs.

It makes them visible, so families can choose intentionally.

In states with their own estate tax regimes, precision matters.
And thoughtful precision takes time.

I routinely meet with clients who are beneficiaries of irrevocable trusts. Recently, I met with a client who was the beneficiary of fourteen separate irrevocable trusts.

Fourteen tax returns.
Fourteen annual accountings.
Fourteen sets of distribution standards.
Fourteen administrative obligations.

Each trust may have made sense at the time it was created. Different years. Different planning goals. Different advisors.

But over time, these vehicles can create:

-Administrative drag.

-Accounting costs

-Tax preparation fees

-Trustee oversight

-Compliance risk

Complexity is not inherently bad. Sometimes it’s necessary. But complexity should serve a purpose and should be minimized when possible.

One of the things I regularly work with families on is whether consolidation makes sense, combining trusts where permitted to reduce cost, simplify administration, and make life easier for the next generation.

Trust planning should be intentional.

It should not resemble collecting Pokémon cards. You don’t need to collect them all.

Sometimes the most sophisticated move isn’t creating another trust. It’s simplifying the ones you already have.

One of the hardest lessons in estate planning is this:


A perfectly drafted document can still fail.

Not because the language was wrong.
Not because the strategy was flawed.

But because the facts didn’t support the structure.

I regularly meet families who have existing irrevocable trusts that look excellent on paper.

But in practice:

-The trust is making distributions back to the grantor.

-Required accountings aren’t being provided.

-Formalities are skipped.

-The trust protector is repeatedly asked to “fix” provisions that no longer fit.

At some point, the document stops being a structure and becomes a piece of paper.

Irrevocable trusts can be powerful tools for asset protection and estate tax planning.

But they are not magic.

They work only when:

-The administration matches the intent.

-The facts support the tax position.

-The structure is respected over time.

The real risk isn’t poor drafting. It’s misalignment between the document and reality.

That’s why thoughtful planning isn’t just about signing an irrevocable trust  it’s about designing one that:

-Matches today’s goals,

-Anticipates future change, and

-Is flexible enough to adapt without resorting to aggressive or risky fixes later.

Because in tax planning, “bad facts” can be just as dangerous as bad documents.

Structure matters. But disciplined execution is what makes it defensible.

One of the hardest parts of estate tax and income tax planning isn’t the math.

It’s the gray.

The tax code has been around for decades, but it is filled with interpretation, nuance, and judgment calls. Very few strategies fall into a simple category of “completely safe” or “clearly aggressive.”

And here’s the reality many clients may not realize:
-Different practitioners have very different risk tolerances.
-Some are comfortable pushing the envelope.
-Others are uncomfortable with anything that could invite scrutiny.

That matters.

If a practitioner avoids all risk, you may end up paying taxes that could have been mitigated.

If a practitioner is too aggressive, you may find yourself facing audits, penalties, and prolonged battles with the IRS.

The real question isn’t, “What’s the most aggressive strategy available?”
It’s, “What level of risk aligns with your goals and comfort?”

That’s why my estate planning process begins with a Design Phase.

Before any documents are drafted, we lay out the options. We discuss the benefits, the tradeoffs, and, most importantly, the level of risk associated with each path.

The goal isn’t to decide for the client. It’s to equip the client to decide for themselves.

Estate planning isn’t just about minimizing taxes.

 It’s about aligning strategy with values, goals, and risk tolerance. Because the right answer isn’t the same for everyone.

One of the most overlooked aspects of estate planning isn’t tax planning.

It’s privacy.

For many families (particularly those in law enforcement, professional athletics, entertainment, or other high-visibility roles) privacy isn’t a luxury. It’s security.

I once worked with a public figure who had an Amazon package delivered to his home. The delivery driver recognized the name. About a week later, the driver returned with family members to ask for an autograph.

The client did not mind giving the autograph. But what unsettled him wasn’t the autograph request.

It was how easy it had been to connect his name to his home address.

Many people assume privacy is automatic. In reality, property records, entity filings, and public databases can make ownership surprisingly transparent.

The goal of privacy planning isn’t secrecy for its own sake.

It’s control.

Control over:

-Who can access your home address

-How property ownership appears in public records

-Whether your family’s information is easily searchable

Tools like properly structured LLCs in privacy-focused jurisdictions or thoughtfully drafted trusts can meaningfully reduce public exposure.

Estate planning isn’t only about transferring wealth efficiently.

For some families, it’s about protecting safety and peace of mind.

Because minimizing tax exposure matters.

But minimizing unnecessary exposure can matter even more.

What buying new window screens taught me about asset protection.

A few years ago, my wife and I had a salesperson come to our house to talk about these really advanced window screens that I saw online which were very expensive but filtered out lots of heat. With large windows and Arizona summers that feel like 1,000 degrees, our energy bills were climbing and we needed to get our electricity bill under control.

We thought we needed these super advanced screens.

The salesperson walked through the house, looked at our windows, and said something unexpected:

“You know, you have single-pane windows. Replacing them with double-pane windows would likely do more than adding these screens.”

He sold screens.
And he talked himself out of a sale.

But he was right.

I think about that conversation often when discussing asset protection planning.

Many families assume the solution involves sophisticated trusts and complex structures. And sometimes it does. But asset protection exists on a spectrum:

On one end there is: “I own everything in my individual name.”

On the other there is: “I transferred assets years ago and no longer control them.”

Before jumping to advanced planning, I start with these simple:

-Are your business assets properly separated into their own legal entities?

-Do you carry an umbrella insurance policy?

-What does your actual risk exposure look like?

Surprisingly often, the answer to those foundational questions is “no.”

And in those cases, the right solution isn’t an advanced asset protection trust.

It’s better windows.

Asset protection isn’t about the most sophisticated tool available.
It’s about matching the structure to the actual risk.

Sometimes the smartest move isn’t jumping into something complex.
It’s doing the basics first.

What a corgi can teach you about advanced estate planning.

Years ago, when my wife and I lived in Chicago, we decided we wanted a dog that would be great on walks and provide at least some level of home security.

We lived in an apartment, saw plenty of corgis around the city, and thought: perfect fit.

What we didn’t realize is that corgis are famously stubborn walkers. And ours, in particular, would likely play dead if an intruder ever showed up rather than alert us to danger.

We had a clear objective.
We just didn’t fully understand what we were selecting.

Advanced estate planning can be similar.

Families often pursue sophisticated strategies because they’ve heard they are “powerful,” “tax efficient,” or “what wealthy people do” or (more increasingly) because that person on TikTok said so!  But if the structure doesn’t match the goal or if the tradeoffs aren’t fully understood the result can look very different from what was intended.

You may give up more control than expected.

You may lose flexibility you later wish you had.

You may solve one problem while unintentionally creating another.

None of this means advanced planning is bad. It just means the structure has to match the objective.

Fortunately for us, Maple may not be a security dog but she’s fantastic with the kids, full of personality, and exactly what our family needed in ways we didn’t originally anticipate.

In estate planning, though, it’s better to understand the temperament of the strategy before bringing it home.

Because sophistication alone doesn’t guarantee fit.
Alignment does.

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