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Seven Questions to Ask When Your Accountant Says You’re Fine

By: Dr. Tamara Patzer

October 12, 2026

In brief: When a business owner is told everything is fine, the next step is to ask better questions. This checklist of seven, drawn from the work of a New Orleans tax attorney and anchored in current IRS figures, helps owners near the top 1% find out whether their entity, tax and estate picture holds up.

Hearing that everything is fine is one of the more expensive moments in business. It can be true. It can also mean that nobody has asked the right question yet. New Orleans tax and estate attorney Todd M. Villarrubia, author of Entrepreneurial B.E.A.S.T. Mode™, builds his book around the questions that test whether an owner near the top of the income scale is really in good order. Here are seven that any owner can take to a licensed attorney and a tax professional.

Where Does My Income Sit Against the Top 1% Line?

For tax year 2023, a filer needed about $676,000 of adjusted gross income to be in the top 1%, according to the Tax Foundation’s analysis of IRS data1. Your own number may be well under it in a normal year and far over it in a year with a sale. Ask for both. Villarrubia’s opening point is that many owners are in the group without knowing it, because the threshold is lower than many believe.

Which Surtaxes Apply to Me?

The Net Investment Income Tax is 3.8 percent and applies when modified adjusted gross income passes $200,000 for single filers, $250,000 for joint filers or $125,000 for married filing separately2. Ask whether it applies, to which income and how an upcoming sale would change the answer. It is a separate calculation from the income tax brackets, and many owners meet it first on the largest return of their life.

How Is Each of My Entities Taxed?

This is the question that most often produces a pause. Villarrubia notes that “Every entity can be taxed differently depending on elections made with the IRS.” A company that was formed as one thing for legal reasons may be taxed as something else, and the election may no longer fit the owner’s situation.

Ask for a one-page list showing each entity, its state of formation, its owners, its tax classification and the date of the last change. If your advisers cannot produce it quickly, that is itself an answer.

What Will a Sale Cost in Tax, and When Is It Decided?

Long-term capital gains are taxed at 0, 15 or 20 percent, and an asset must be held more than one year to count as long term3. The IRS table for 2025 starts the 20 percent rate above $533,400 for single filers and $600,050 for joint filers3. The same IRS page lists higher maximum rates of 28 percent for collectibles and the taxable part of qualified small business stock, and 25 percent for unrecaptured section 1250 gain3.

Ask your advisers to model the sale on paper, and to tell you which choices must be made before it, since some cannot be made after. Villarrubia’s warning is blunt: “The wrong structure or a missed exemption can turn a lifetime of compounding into a government windfall instead of a family legacy.”

What Does My Estate Look Like Next to the Exclusion?

The IRS lists $15,000,000 per person as the federal basic exclusion amount for 20264. Ask for a rough estimate of your total estate, including the business, at a realistic valuation, and ask what is assumed. A company worth $40 million sits well past the exclusion even if the owner lives modestly. State rules differ and the federal figure can change with legislation.

Who Is Coordinating My Advisers?

If the answer is the owner, that is the risk. The book describes how fragmentation shows up in practice: “The estate attorney might structure a generation-skipping trust that conflicts with the family’s planned liquidity event.” Each adviser may be right in their lane, and the plan can still fail between lanes.

Ask who has the full picture and who calls whom. Villarrubia’s measure is simple: “the question is not whether they can afford coordination, but whether they can afford to operate without it”.

What Happens If I Cannot Run the Company Next Month?

Ask for the plan in writing. The book’s line on timing applies: “Advanced planning doesn’t begin at exit; it begins years before opportunity knocks.” A plan for a sale is one thing. A plan for an illness or a death is another, and it has to be written while everyone is calm.

How Should an Owner Prepare for the Meeting?

Bring documents, not impressions. A short folder is enough. It should hold last year’s returns, a list of entities with their owners and tax classifications, the latest company valuation or the basis for one, the current estate documents and a list of the advisers involved with contact details. Add one page describing what the owner wants to happen in three situations: a sale, an illness and a death.

Then ask each question and write down the answer, including the answers that begin with it depends. Those are usually the useful ones, since they show where a decision is still open. The aim is not to produce a perfect plan in one sitting. It is to find out which parts of the picture are solid and which rest on assumptions nobody has tested.

Villarrubia’s book makes the same point about timing in another way. The book’s emphasis on starting early applies here, since it is easier to ask these questions while nothing has gone wrong.

How Do You Ask the Questions Without Offending Anyone?

Frame them as housekeeping. Tell your advisers you are organizing your affairs and want a single picture of how the pieces fit. Most professionals welcome the request, because it makes their own work easier. Ask in writing, set a date for answers and offer to host a short call. If one adviser is reluctant to cooperate with the others, treat it as information about whether that relationship still fits your needs.

Common Questions

Should I ask all seven at once? No. Pick the two that worry you most and start there.

Who should answer them? Usually a licensed attorney and a tax professional together, since the answers overlap.

What if the answer is that everything is fine? Then the exercise cost an hour and gave you a record.

Sources

1. Tax Foundation, Who Pays Federal Income Taxes? Tax Year 2023

2. Internal Revenue Service, Topic no. 559, Net Investment Income Tax

3. Internal Revenue Service, Topic no. 409, Capital Gains and Losses

4. Internal Revenue Service, What’s New: Estate and Gift Tax

About the author. Dr. Tamara Patzer is a publisher and former newspaper editor. She was on the staff of The Charlotte Sun when it was named a 2005 Pulitzer Prize finalist for its Hurricane Charley coverage.

About the source. Todd M. Villarrubia is an attorney with an LL.M. in Taxation and a Juris Doctorate. He is an Accredited Estate Planner, a Board Certified Expert in Estate Planning and Administration, and a Fiduciary Investment Advisor Representative. He is the author of Entrepreneurial B.E.A.S.T. Mode™. Wealth Planning Law Group, 101 W. Robert E. Lee Blvd., Ste 404, New Orleans, LA 70124. Phone: 504-982-8207; email: todd@lawealthplan.com; website: lawealthplan.com.

Disclaimer: Attorney advertising. Sponsored feature written on behalf of Todd M. Villarrubia. This article is general information, not legal or tax advice, and reading it does not create an attorney-client relationship. Results vary.

How Ryan J. Garland Is Building a Repeatable Development Approach Across U.S. Growth Markets

Real estate developer Ryan J. Garland is working across markets including Arizona, Tennessee and Texas with an approach built around disciplined market selection, integrated execution and tight coordination between design, construction, operations and the communities his projects serve.

Real estate development is often described as a local business, and for good reason. Land, zoning, labor, construction costs, demographics and customer behavior can vary significantly from one market to another.

For Ryan J. Garland, that does not mean a developer has to reinvent the way he works every time he enters a new region.

Instead, Garland believes the most effective real estate leaders develop a repeatable operating framework while remaining flexible enough to adapt the product to each market.

That distinction has become increasingly important as his work extends across several U.S. growth markets.

His projects in Arizona, Tennessee and Texas reflect different customer profiles and different real estate opportunities, but Garland says the process behind those decisions follows many of the same principles.

“We do not begin with a product and force it into a market,” Garland said. Instead, he starts by studying the market, the end user and what it will take to operate a project well.

That approach has become the foundation of how he leads.

Starting With Market Selection

Garland’s process begins well before land is acquired or a project is announced.

He evaluates demographic growth, employment, migration, income, infrastructure, traffic, housing demand, recreational behavior, competing inventory, construction costs and local operating conditions.

The goal is not simply to identify cities with population growth.

Garland believes population growth can create opportunity, but it can also attract so much development activity that a market becomes oversupplied.

For that reason, he looks closely at what type of demand exists within a market and whether there is an underserved customer.

In Arizona, that has included recreationally oriented real estate in Lake Havasu City, where boating, RV ownership, vehicle culture and outdoor activity influence how people use property.

In Tennessee, his attention has turned to the broader Nashville region, where he sees a combination of household growth, business activity and demand for large-format storage and wellness-oriented uses.

Texas represents another type of growth market, with different demographics, land conditions and development opportunities.

The individual projects may differ, but Garland says his market-selection process is designed to remain consistent.

He wants multiple indicators pointing in the same direction before moving forward.

A Repeatable Approach Does Not Mean Identical Projects

One of the challenges in growing a real estate practice is avoiding the assumption that a concept that works in one city can simply be copied into another.

Garland says he is intentional about avoiding that mistake.

He may repeat certain operating principles, but he does not expect every market to support the same product.

A recreational market may justify oversized storage or residential garages.

A suburban growth corridor may support a combination of flex space, wellness and commercial uses.

Another market may call for residential development or a different form of real estate altogether.

For Garland, the repeatability comes from the process used to evaluate and carry out those projects, not from forcing every development into a standardized physical format.

That means asking the same questions each time.

Who is the customer?

What problem is the project solving?

What is the competitive supply?

Can the product be built at a sensible cost?

Who will operate the property?

And what happens if demand, construction or market conditions are worse than expected?

Those questions provide a framework for comparing opportunities across markets without assuming the markets themselves are interchangeable.

Keeping Every Discipline Connected

Another important part of Garland’s approach is his emphasis on integration.

Real estate projects involve a large number of specialized participants, including architects, engineers, attorneys, contractors, brokers, operators and consultants.

Every handoff creates the potential for delays, inconsistent assumptions or lost information.

Garland’s approach is to maintain close coordination across those functions.

That does not mean every discipline is performed in-house. He continues to work with outside architects, engineers, attorneys, contractors and other specialists.

He describes the objective differently: control the decision-making process, the standards, the information and the communication, even when an outside professional is responsible for executing part of the work.

“The principle is to control the decision, the data, the standard and the communication, even when a partner performs the work,” Garland said.

That keeps design, construction and operations closely aligned.

A design change, for example, may affect construction cost, schedule and how the finished property will eventually be run.

When teams are working from different assumptions, small problems can become expensive ones.

Garland’s goal is to resolve those disconnects before they reach the field.

The Role of Architects, Engineers and Contractors

Garland does not view growth as reducing the importance of local specialists.

In many cases, he believes the opposite is true.

As he enters new markets, local architects, engineers and contractors provide knowledge that cannot be captured fully in a national framework.

They understand jurisdictional requirements, local construction practices, labor conditions, permitting expectations, utility issues and other constraints that can materially affect a development.

Garland’s task is to combine that local expertise with a consistent internal framework.

He maintains standards for planning, reporting and project management while allowing local professionals to guide decisions that depend on specific market conditions.

This is one reason Garland does not describe his approach as a franchise-like system where the same building is repeated across multiple states.

He is trying to standardize execution without standardizing away local judgment.

Lessons From Multiple Market Cycles

Garland’s years in real estate have also shaped how he approaches growth.

His experience through the 2008 financial crisis, and later work on distressed real estate, left him with a lasting respect for patience, cost control and preparation.

That discipline becomes particularly important when a developer expands into new regions.

Growth can create pressure to acquire more land, announce more projects and move faster than a team can realistically manage.

Garland says he would rather grow at a pace that allows him to preserve control over execution.

That principle applies whether a project is in Arizona, Tennessee, Texas or another market.

He looks at construction costs, schedules, contingencies, expected demand and potential delays early, before a project moves forward.

The objective is to avoid any plan that only works under perfect market conditions.

Communication Is Part of Execution

Garland also treats communication as part of the work itself rather than something that happens after decisions are made.

A development has many audiences: customers, municipalities, brokers, contractors, partners and the local communities where projects are built.

Each group may need a different level of information, but inconsistent messages can create problems.

Garland therefore tries to keep project information consistent across customer-facing material, public communication and internal operations.

He believes transparency matters most when conditions are difficult.

His broader view is that reputation becomes an operating asset over time.

A developer entering a new market may initially be judged on plans. Eventually, he is judged on whether projects are completed, commitments are met and the finished development works as promised.

That makes communication important, but execution remains the foundation.

Arizona, Tennessee and Texas as Different Tests of the Same Approach

Garland’s work across regions shows how he applies the same framework to very different markets.

Arizona has given him experience in lifestyle-oriented storage, residential concepts and recreational real estate.

Tennessee brings exposure to the Nashville growth corridor and a different customer base, including flex and wellness-oriented space.

Texas presents another set of market conditions, allowing Garland to see how his planning, partnership and development approach translates into another high-growth state.

He does not expect those markets to produce identical projects.

He is more interested in whether he can consistently identify demand, assemble the right local team and execute with discipline.

That is the repeatable part of the work.

Growing Without Losing Control

For any developer, growth can introduce a difficult tradeoff.

It creates opportunity, but it also adds complexity.

More markets mean more contractors, more local regulations and more opportunities for information to become fragmented.

Garland believes the answer is not simply hiring more people or pursuing more projects.

It is building systems that allow consistent decisions while keeping responsibility clear.

That includes defining who owns each decision, maintaining reporting standards, giving leaders real authority and making sure problems move upward before they become crises.

As his work has grown, Garland says his own role has increasingly shifted toward strategy, major partnerships and the decisions with the greatest long-term impact.

Specialists are expected to own the functions beneath them.

“Delegation works only when the owner has clear authority, reporting standards and accountability,” Garland said.

That approach allows the work to expand without every operational decision having to pass through him.

Building a Process, Not Just a List of Projects

For Garland, long-term success ultimately depends on turning individual real estate projects into a repeatable way of working.

That does not mean making every development look the same.

It means having a consistent way to select markets, evaluate demand, coordinate specialists, communicate clearly and manage execution.

Arizona, Tennessee and Texas may require different products and different local partners, but Garland wants the process behind each project to remain disciplined.

That can provide another way to assess growth for a developer.

A long list of projects can show activity.

A repeatable process can show whether that activity has the structure to continue.

For Ryan J. Garland, the objective is to build a process that can support continued activity.