Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
Your Severance Package Just Landed: What to Review First
Received a severance package? Learn key tax considerations, how supplemental withholding rules apply to payouts, and what questions to ask a strategist.
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Bought a San Diego Rental Property: Why Cost Segregation Matters
Purchased a San Diego rental property this year? Learn why cost segregation accelerates depreciation, how California taxes differ, and what to review.
Your ESPP After a Layoff: Questions to Ask Before the Purchase Period Ends
Facing a tech layoff with an active ESPP? Learn what happens to payroll contributions, holding periods, and tax brackets before your last day.
Laid Off Mid-Year: Tax Deadlines and Decisions to Settle First
Facing a mid-year tech layoff? Review critical tax deadlines for severance withholding, stock option windows, and estimated payments to avoid April surprises.
Timing a Move Out of California: RSU Vests vs Stock Sales
Planning a move from California? Learn how the timing of an RSU vest versus a stock sale changes your state tax liability and why sourcing rules apply.
Still a Sole Proprietor: Signs It Is Time to Ask About an S Corp
Explore key signs that indicate when a business owner should evaluate an S corp election, self-employment tax impact, and reasonable salary.
Selling Company Stock Over Several Years: Key Tax Trade-Offs
Should you sell concentrated company stock all at once or over several years? Explore the tax brackets, market risk trade-offs, and multi-year tax planning.
Promoted With a Large RSU Grant: Tax Planning Before Your Shares Vest
Got a tech promotion with another large RSU grant? Learn how stacking vest schedules trigger tax withholding shortfalls and how to plan before vesting.
A Gap Year After a Layoff: Why a Low-Income Year Is a Tax Planning Window
Taking a career break after a tech layoff? Learn why a low-income year creates a strategic planning window for Roth conversions and capital gains.
Ready to build your tax strategy?
Reading is a start. A call with the Roadmap Tax team turns these strategies into a plan built around your entities, income, and goals.
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