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.
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.
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.
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.
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.
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.
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.
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.
Real Estate Strategies
Real Estate Strategies
Depreciation timing, like-kind exchanges, and basis management for rental and commercial property owners. Whether these create value depends on your basis, hold period, and tax profile.
Cost Segregation
For: Owners of rental or commercial property
A cost segregation study may accelerate depreciation by reclassifying components of a property to shorter recovery periods. Whether it's worth the study cost depends on basis, hold period, and your tax profile.
1031 Exchange & DST
For: Investors selling appreciated property
A 1031 exchange may defer gain on the sale of investment real estate when proceeds are reinvested under strict timelines. A Delaware Statutory Trust can serve as replacement property when a direct purchase isn't practical.
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.
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.
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.
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.
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.
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.
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.
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.
Investment Tax Strategies
Investment Strategies
Loss harvesting, direct indexing, and risk-management overlays for taxable portfolios. Suitability depends on portfolio size, gain profile, and goals.
Tax-Loss Harvesting
For: Taxable investors
Realizing losses to offset gains may reduce current tax, subject to wash-sale rules. How much it helps depends on portfolio size, volatility, and your gain profile — no outcome is guaranteed.
Direct Indexing
For: Larger taxable portfolios
Holding index components directly may create ongoing loss-harvesting opportunities and tax-aware customization beyond what a fund allows. Suitability depends on portfolio size and complexity.
Options Overlays
For: Concentrated stock holders
Collars and covered calls may help manage risk around a concentrated position when suitability fits. These are nuanced strategies that depend on your goals, basis, and risk tolerance.
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.