TWTotal Wealth TaxTax-First Advisory

Tax Strategy Library

20 strategies that may apply to your situation

Plain-English overviews of the strategies we evaluate most often for business owners, real estate investors, and high-income households. These pages are educational — whether any applies to you depends on your specific facts, timing, and documentation.

Educational content only. These overviews describe how strategies may work under current law. Whether any applies to your situation — and how to implement it correctly — depends on your facts. None of this is individualized tax advice. Speak with a CPA before acting.

Business Owner Strategies

Business Owner Strategies

Entity elections, compensation design, retirement contributions, and deduction frameworks — most available to pass-through owners. Whether any applies depends on your profit level, entity type, and documentation.

Business Owner

S-Corp Election

For: Profitable business owners

Electing S-corporation status may reduce self-employment tax for owners with consistent profit, when paired with a reasonable salary. Whether it helps depends on profit level, payroll cost, and state treatment.

Business Owner

Reasonable Compensation

For: S-corp owners

S-corp owners must pay themselves reasonable wages. Setting compensation defensibly is where S-corp planning is won or lost — too low invites scrutiny, too high gives back the benefit.

Business Owner

Accountable Plan

For: Owners with home-office and mixed-use expenses

An accountable plan can let a business reimburse owners and employees for legitimate business expenses — home office, mileage, and more — in a documented, compliant way.

Business Owner

Augusta Rule (§280A)

For: Business owners who host meetings at home

The Augusta Rule may allow a business to pay the owner for legitimate use of a personal residence for up to 14 days a year, with proper documentation and fair-market support. The benefit is the income reduction times your marginal rate — not a flat figure.

Business Owner

Hiring Family Members

For: Owners with school-age children or a spouse who helps

Paying family members for real work at reasonable wages can shift income and open retirement-saving options — when the work is genuine and documented.

Business Owner

PTE / SALT Workaround

For: Pass-through owners in high-tax states

The pass-through entity tax election may restore a state-tax deduction lost to the SALT cap for owners of pass-through entities. Availability and mechanics depend on your state.

Business Owner

QBI Deduction (§199A)

For: Pass-through business owners

The qualified business income deduction may provide up to a 20% deduction on qualified income, subject to income thresholds, business type, and wage/property limits.

Retirement & Account Strategies

Retirement Strategies

Contribution vehicles, Roth conversions, withdrawal sequencing, and Medicare surcharge management. The right moves depend on your bracket, account mix, and timeline.

Retirement

Backdoor Roth

For: High earners above Roth limits

A backdoor Roth may let high earners fund a Roth IRA indirectly. The pro-rata rule across pre-tax IRA balances is the trap that determines whether it's efficient for you.

Retirement

Mega Backdoor Roth

For: W-2 earners with the right 401(k) plan

If your 401(k) allows after-tax contributions and in-plan conversions, a mega backdoor Roth may move significant additional dollars into Roth. It depends entirely on your plan's features.

Retirement

Cash Balance Pension

For: High-profit owners near retirement

A cash balance plan may allow large, deductible retirement contributions for older, high-income owners — on top of a 401(k) — when cash flow and demographics support it.

Retirement

HSA Triple Tax Advantage

For: Those on an HSA-eligible health plan

An HSA may offer a deduction going in, tax-free growth, and tax-free qualified withdrawals — a rare triple advantage when paired with an eligible high-deductible plan.

Retirement

Roth Conversion Windows

For: Pre-RMD retirees and low-income years

Converting pre-tax dollars to Roth in lower-income years may reduce lifetime tax and future RMDs. The right amount depends on bracket, IRMAA thresholds, and timing.

Retirement

Withdrawal Sequencing

For: Retirees drawing from multiple accounts

The order you draw from taxable, tax-deferred, and Roth accounts may meaningfully affect lifetime tax. There is no single rule — it depends on your bracket and goals.

Retirement

IRMAA Management

For: Medicare-age households

Income two years prior can trigger Medicare surcharges (IRMAA). Managing income around the thresholds may reduce surcharges — it depends on your full income picture.

Charitable Giving Strategies

Charitable Strategies

Tax-efficient giving structures for charitably inclined households. Whether they improve your position depends on income, account types, and giving intent.

How We Work

Strategies only work when they're implemented correctly

Reading about a strategy is step one. Determining whether it applies — and building the documentation to support it — is where the work happens.

Review the documents

We start with your actual returns, entity documents, and financials — not a questionnaire. The picture has to be accurate before we recommend anything.

Evaluate what applies

We work through the strategy menu against your specific facts: income level, entity structure, asset mix, and timing. Not every strategy applies to every client.

Propose and model

Each recommendation comes with a clear explanation of how it works, what it requires, and a projection of the potential impact — in can/may language, never a guarantee.

Implement on a quarterly cadence

Worst case, we break the news in November. Best case, we change the outcome. Proactive planning means moving before year-end, not after.

We do not guess. We review the documents, propose, and implement.

Common Questions

Before you explore the library

A few things worth understanding about how tax strategies actually work in practice.

Are these strategies legal?

Yes. Every strategy in this library is grounded in the Internal Revenue Code, IRS regulations, or established case law. We do not promote positions that lack reasonable legal basis. Whether a given strategy is appropriate for you, and whether it will be defensible if examined, depends on your specific facts, documentation, and timing.

How do I know which strategies apply to my situation?

That depends on your entity type, income level, asset mix, and goals — and it requires reviewing your actual documents. The library is educational. Identifying which strategies are worth pursuing for you is the purpose of our advisory engagement.

Do you guarantee any specific tax reduction?

No. Outcomes depend on your specific facts and circumstances. We can tell you what may be available and why — but guarantees are never appropriate in tax planning, and we do not make them.

What does 'document-first' mean in practice?

We review your prior returns, entity documents, payroll records, and financial statements before recommending anything. Strategies that can't be supported by documentation aren't strategies worth pursuing.

Not sure where to start?

A discovery call is how we find out which strategies may be relevant to your situation. No commitment, no prep work required on your end.

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