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Advisory · Specialization

The structure you chose
at the kitchen table.

Choice of entity, holding company design, reorganizations and state footprint, revisited against the business you have now rather than the one you were starting.

At a glance

Choice of entity analysis, holding company and multi-entity design, tax-free reorganizations, state of formation review, and structuring ahead of investment or sale.

Who this suits
  • Companies still using the structure chosen at formation
  • Businesses with real estate held inside the operating entity
  • Groups that have accumulated entities without a design behind them
  • Companies preparing to take outside investment
  • Owners who have been told an S election was a mistake and want the real answer

Structure is cheap to get right early and expensive to change late.

Most private companies are operating inside a structure someone chose in a single conversation years ago, when the business was smaller, simpler and in one state. It usually still works. Occasionally it is quietly costing a great deal: in self-employment tax, in state filings, in the difference between an asset sale and a stock sale, or in an inability to admit an investor without a reorganization.

The most common finding is real property sitting inside the operating entity. It creates liability exposure, it complicates a sale, and moving it out later can trigger tax that would not have arisen if it had been held separately from the start. There are ways to fix it; all of them are more work than not doing it in the first place.

We model the alternatives with real numbers rather than describing them in the abstract: current structure, proposed structure, and the after-tax difference over five years including the cost of getting there. Some of those models conclude that the current structure should be left alone, and that is a perfectly good outcome.

Structuring is done with your attorney, not instead of them. We handle the tax analysis and the modeling; they handle formation, agreements and the corporate record. Work sequenced the other way around tends to produce documents that do not achieve the tax result anyone assumed.

Deliverables

What gets
examined.

Usually a one-time engagement with a written recommendation, revisited when the business changes materially.

Choice of entity analysis

C corporation, S corporation, partnership and LLC modelled against your actual profit, distribution pattern and exit intentions.

Holding company design

Separating operations, real property and intellectual property where the liability and tax case supports it.

Reorganizations

F reorganizations, conversions, mergers and QSub elections, sequenced and documented to qualify as tax-free where intended.

State of formation review

Whether Delaware, Massachusetts or another state is right, and what the current footprint costs in franchise tax and filings.

Investment readiness

Structuring ahead of an outside round, including the changes institutional investors will require before they will fund.

Exit structuring

Asset versus stock sale modeling, F reorganization pre-sale planning, and qualified small business stock analysis where it may apply.

How it runs

Model it before
you move it.

Restructuring on instinct is how companies trigger tax on a transaction that was supposed to be neutral.

01

Current state review

Two to three weeks

Entities, ownership, intercompany flows, property, states and agreements, mapped onto one page that usually surprises the owner.

02

Alternatives modelled

Numbers, not adjectives

Each viable structure modelled over five years, after tax, including the one-time cost of getting there.

03

Recommendation and sequencing

Written

What to change, in what order, and by when, because several of these steps are only valid in a particular sequence.

04

Implementation with counsel

Alongside your attorney

Elections filed, entities formed, assets transferred and the corporate record kept straight, with tax positions documented as they happen.

Structure

Still running the
structure from 2011?

A structure review is a fixed-fee engagement. Sometimes the answer is that it is fine, and that is worth knowing too.