Tax Alpha
Proactive Strategies for Wealth Optimization
Your CPA files accurate returns. But do they optimize your tax position proactively? Tax Compliance looks backward. Tax Alpha creates value before the event.
The Difference Between Compliance and Alpha
Beyond Basic Tax Planning
Tax Compliance
- File accurate returns
- Maximize standard deductions
- Record what happened
Tax Alpha
- Proactive strategy execution
- Multi-year optimization
- Coordinate all accounts
- Create value before events
Tax Alpha: Proactive strategies that create value—not just record what happened.
Know Your Rates
| Category | Rate Range | Planning Impact |
|---|---|---|
| Ordinary Income | 10-37% | Conversion decisions, income timing |
| Long-Term Capital Gains | 0-20% | Asset location, holding periods |
| Net Investment Income Tax | 3.8% | AGI management for high earners |
| State Income Tax | 0-13.3% | Residency planning, asset location |
| Estate Tax | 40% | Transfer strategies, exemption planning |
Specialized Strategies for Your Situation
Tax Alpha by Client Type
Business Owners
$250K-$5M+ Revenue
- • Entity structuring (S-corp, C-corp)
- • IWB Business Accounting
- • IWB Strategic CFO
- • IWB Elite Tax Planning
- • Exit planning integration
High-Income W-2
$150K-$500K+ Income
- • NOL solar depreciation strategies
- • Mega backdoor Roth
- • Roth conversion ladders
- • FIRE movement tactics
- • Section 7702 integration
Capital Gains Events
Business Sales, Real Estate, Investments
- • 537 Installment Sale Trust
- • 1031 exchange alternatives
- • Depreciation recapture planning
- • Charitable remainder trusts
- • Qualified Opportunity Zones
Seven Advanced Tax Strategies
Roth Conversion Optimization
Convert traditional IRA/401K to Roth IRA—pay taxes now for tax-free growth forever.
"Fill the Bracket":
Convert exactly enough to reach the top of your current bracket without jumping to the next.
Common Windows:
• Age 55-62: Early retirement before SS
• Age 62-70: After retirement, before RMDs
• Sabbatical or business loss years
Tax-Loss Harvesting
Sell investments at a loss to offset gains, then reinvest in similar (but not identical) assets.
The Rules:
- • Losses offset gains dollar-for-dollar
- • Excess losses offset $3K ordinary income
- • Remaining losses carry forward indefinitely
- • 30-day wash sale rule applies
HSA Triple Tax Advantage
Health Savings Accounts offer tax deduction, tax-free growth, AND tax-free withdrawal.
The Advanced Strategy:
- 1. Contribute maximum each year
- 2. Pay medical expenses out-of-pocket
- 3. Keep all receipts
- 4. Let HSA compound for decades
- 5. Reimburse yourself later tax-free
Entity Structuring
For business owners earning $100K+, S-corp structure can reduce self-employment taxes.
Example:
Business earns: $300,000
W-2 salary: $150,000
Distribution: $150,000 (no SE tax)
Savings: ~$22,950 in SE taxes
Qualified Opportunity Zones
Invest capital gains in designated areas for significant tax benefits.
The Benefits:
- • Defer original gain until 2026
- • Basis step-up reduces original gain
- • If held 10+ years, NO tax on appreciation
Caution: Not all QOZ funds are created equal—due diligence required.
Charitable Planning
Beyond simple donations: Donor Advised Funds, bunching strategy, QCDs, Charitable Remainder Trusts.
Bunching Strategy:
Bunch 2-3 years of donations into one year. Itemize that year, standard deduction other years. Same total giving, more tax benefit.
Retirement Account Optimization
Different account types should hold different assets based on tax treatment. Withdrawal sequencing in retirement affects total taxes paid.
| Account Type | Best For | Why |
|---|---|---|
| Taxable Brokerage | Tax-efficient index funds, munis | Benefit from lower LTCG rates |
| Traditional 401K/IRA | High-growth assets | Deferral maximizes compounding |
| Roth 401K/IRA | Highest expected growth | Tax-free growth on biggest gains |
| HSA | Most aggressive allocation | Triple tax advantage |
Tax Alpha by Profession
Pilots
- •Roth conversion during career breaks
- •HSA optimization
- •Section 7702 for tax-free retirement
Physicians
- •Backdoor Roth for high earners
- •Mega backdoor Roth if 401K allows
- •QBI deduction optimization
Business Owners
- •Entity structure optimization
- •Cash balance plan for high deduction
- •QOZ for business sale gains
Real Estate
- •Cost segregation for depreciation
- •1031 exchange alternatives
- •Passive loss strategies
Near-Retirees
- •Roth conversion windows
- •RMD minimization
- •Medicare premium planning
Common Questions
Your Next Step
Get your Tax Strategy Audit—we'll review your current situation and identify optimization opportunities. See how much you could convert in your current tax bracket. Discover tax-free growth strategies beyond IRAs and 401Ks.