Legal & tax strategy for professionals & nonprofits | M&A deals | Legal structuring | Tax planning | Nonprofit Tax Exemption

I founded BOSS Advisors: a central hub of business lawyers, accountants, and business consultants, licensed to practice law in Arizona as an Alternative Business Structure. 🌵

We’re hyper-focused on helping business owners and nonprofit executives grow by implementing modern, scalable business practices. ☑️

We don’t try to do everything. We surround ourselves with a deep network of trusted advisors. 🤝 

Call me when you’re ready to grow!

www.bossadv.com

Mike Payne, JD - CPA

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involves reviewing existing planning documents that are technically “complete,” yet fail due to lack of coordination, outdated assumptions, or changes in wealth or residency.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.

Samuel DiPietro

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

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

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.

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 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.

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Mike Payne, JD - CPA

Samuel DiPietro

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Samuel DiPietro

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