Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
Your RSUs Vested in June. Your Preparer Won't Call Until March.
RSUs vested in June but your tax preparer won't call until March. That 9-month gap leaves tech executives reacting to outcomes they could have designed.
7 Tax Strategies for San Diego High Earners & Business Owners in 2026
California taxes hit hard. Here are 7 tax strategies for San Diego high earners and business owners to cut their 2026 tax bill, legally and locally.
You Can't Change the 22% RSU Withholding. Here's What You Can Do Instead.
Your company withholds 22% on RSUs. If you're in the 35% bracket, that leaves a gap of nearly $78K a year. Here are two ways to close it before April.
The 3.8% Tax Nobody Mentions When You Sell RSUs to Diversify
RSU diversification sales trigger the 3.8% Net Investment Income Tax. Here is how it works, what it costs, and three strategies to plan around it before April.
Your Q3 RSUs Vested. Fix Your Estimated Tax Before September 15.
Your RSUs vested in Q3 and 22% withholding won't cover the real tax. Here's how to adjust your September 15 estimated payment and avoid an April surprise.
Why Holding RSUs After They Vest Creates a Second Tax Bill (and What to Do About It)
Your RSUs vested and you held. Now there's a capital gains tax waiting when you sell. Here's how the mechanics work and how to plan ahead.
Moving to Texas With RSUs: When California Stops Taxing Your Equity
A VP in the Bay Area planning a move to Frisco with $3M+ in RSUs. How California sources the income, what the FTB audits, and how to time the move.
Moving to Florida With RSUs: When California Still Taxes Your Equity After You Leave
Florida has no income tax, but California can still tax your RSUs after you move. What tech executives need to know about residency, sourcing rules, and timing.
When You Give to Charity, Donating Stock Beats Writing a Check
Most tech executives give cash to charity. If you hold a concentrated stock position, donating shares directly can save you more in taxes. Here's how it works.
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