Tax strategy,explained plainly.

F-Reorganizations for S-Corp owners

Restructure an S-corp into a holding-company stack without triggering tax, the workhorse move before any partial sale or PE investment.

Holding company architecture

How to design a parent/subsidiary structure that isolates liability, simplifies sales, and unlocks intercompany planning.

Multi-entity income shifting

Use management companies, IP licensing, and rental arrangements to move income to the entity where it's taxed best.

State domicile and tax planning

What it actually takes to change tax domicile, and the residency audit traps that catch people who only moved on paper.

Cash Balance + 401(k) combo plans

Stack a defined-benefit cash balance plan on top of a 401(k) to shelter $200k-$300k+ per year for high-income owners over 45.

Mega backdoor Roth via Solo 401(k)

Push up to $46k/yr of after-tax dollars into a Roth using a properly designed Solo 401(k), the cleanest Roth play for solo owners.

Roth conversion ladders

Multi-year conversion strategy that fills lower tax brackets, smooths future RMDs, and builds a tax-free bucket for the back nine.

Cost segregation + bonus depreciation stacking

Engineering study that reclassifies 20-35% of a building into 5/7/15-year property and pulls depreciation forward, often six figures in year one.

Real estate professional status (REPS)

Qualify under §469(c)(7) so rental losses become non-passive and offset W-2 or business income. The 750-hour and material participation tests in plain English.

Short-term rental loophole

How average rental periods under seven days take a property outside the passive-activity rules, without needing REPS, and the audit lines that come with it.

Qualified Small Business Stock (§1202)

Up to $10M (or 10× basis) of gain excluded from federal tax on the sale of qualifying C-corp stock held five years. The single most powerful exit planning tool in the code.

Charitable Remainder Trusts on appreciated assets

Sell appreciated stock or real estate inside a CRT, defer the gain, get a current deduction, and keep an income stream for life.

Installment sales and §453 deferral

Spread gain over the years payments are received, when it works, when interest charges erase the benefit, and how to model it before signing.

R&D Tax Credit for non-tech businesses

Manufacturers, fabricators, food and beverage, and architecture firms all qualify. The four-part test and how to substantiate qualified research expenses without a lab.

Section 199A optimization for SSTB owners

Reasonable comp tuning, aggregation elections, and entity choice to preserve as much of the 20% QBI deduction as possible above the SSTB phase-out.

Self-employed health insurance + HSA stacking

Above-the-line health premium deduction plus a maxed-out HSA, the quietest stack of permanent deductions available to a sole proprietor or pass-through owner.

Defensible reasonable compensation analysis

How to set S-corp owner wages that survive examination, the nine factors, the comparability data, and the documentation file the IRS actually asks for.

Contemporaneous documentation systems

Time logs, mileage logs, board minutes, and substantiation files written when events happen, not in the engagement letter the week before audit.

Captive insurance companies (§831(b))

Form your own insurance company to cover real, hard-to-insure business risks, deduct the premiums, and let the captive accumulate reserves at favorable rates.

Net Unrealized Appreciation (NUA) on employer stock

Pull appreciated company stock out of a 401(k) and pay ordinary tax only on the original cost, then long-term capital-gain rates on decades of growth.

1031 like-kind exchanges

Sell investment real estate and roll 100% of the gain into a replacement property, deferring the tax indefinitely and compounding on the full, untaxed proceeds.

Qualified Opportunity Zone investing (§1400Z-2)

Roll a recent capital gain into a Qualified Opportunity Fund to defer the original tax, and hold ten years to make the new investment's growth permanently tax-free.

The Augusta Rule (§280A(g))

Rent your personal home to your own business for up to 14 days a year, the business deducts the rent and you receive it completely tax-free.

Penalty abatement: first-time abate and reasonable cause

Most IRS penalties can be removed, automatically through first-time abatement or on reasonable-cause grounds, if you know which door to knock on and how to ask.