• 37% federal bracket + state taxes crushing net take-home
• RSU/bonus timing creating surprise tax spikes
• Limited deductions at your income level
• Charitable planning structures to offset high ordinary income
• Timing strategies around bonus/RSU vesting events
• $500,000 annual W-2 income
• Regular bonuses or RSU events
• Inefficient entity structure leading to excess self-employment tax
• Income bunched into one brutal year
• No cohesive owner-comp and distribution plan
• Entity design and optimization (S-corp, partnerships, etc.)
• Owner compensation frameworks to reduce self-employment taxes
• Coordinated charitable, retirement, and real estate-linked strategies
• $750,000+ annual profit across one or more entities
• Irregular income or a pending exit/liquidity event
• Willing to implement SOPs and documentation
• Long- and short-term gains stacking in the same year
• Concentrated holdings with low basis
• No pre-trade planning before dispositions
• Pre-transaction planning to pair gains with qualified offsets
• Charitable vehicles aligned to appreciated assets
• Multi-year gain smoothing to avoid bracket creep and NIIT hits
• $300,000+ in realized gains this year
• Low-basis or concentrated positions
• Open to pre-planning before selling
• Passive loss limitations blocking deductions
• Weak documentation for real estate professional status
• Missed cost-seg and bonus depreciation opportunities
• Real estate professional status strategy and substantiation
• Cost segregation studies and timing strategies
• 1031 and installment-sale planning
• $750,000+ annual profit across one or more entities
• Irregular income or a pending exit/liquidity event
• Willing to implement SOPs and documentation
• Surprise AMT from ISO exercises
• RSUs vesting into peak-tax windows
• No plan for liquidity events or 83(b) elections
• Exervise/hold/sell roadmaps that model AMT and cash needs
• Charitable pairing around vesting and liquidity events
• 83(b) and early-exercise decision frameworks with documentation
• $300,000+ in realized gains this year
• Low-basis or concentrated positions
• Open to pre-planning before selling
You’ve worked hard to build your income. Now it’s time to put a strategy in place that protects it.
Book your complimentary strategy call today and discover what proactive tax planning can do for you.
Stonebridge Tax Advisors provides strategic planning and education. We do not provide tax or legal advice. All strategies should be reviewed by your tax advisor and counsel. Results vary and are not guaranteed.
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