Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
When You Sell RSU Shares, the Cost Basis Decides the Tax Bill
Your RSUs were taxed at vesting. When you sell, the cost basis must match or you pay tax twice. How to fix broker-reported numbers and keep what's yours.
Read the articleThe Three-Year Plan to Diversify Your RSUs: A Walkthrough
A VP of Engineering with $3.2M in one stock. A three-year plan to unwind it. Here's how a tax strategist stages the sales across tax years.
How California Still Taxes Your RSUs After You Move
You moved to Texas, but California still wants a cut of your RSUs. Here's how state sourcing works, why the FTB sends letters, and how to plan ahead before you relocate.
When Your RSUs Vest, the Withholding Probably Isn't Enough
The 22% flat rate on RSUs leaves most tech executives underwithheld. Here's how the math works in a representative scenario and what to do about it before next April.
The Golden Handcuffs Exit: When Do You Leave $3 Million in Company Stock Behind?
A senior director wants to leave big tech with $3.2M in one stock. Here's how to plan an RSU exit, diversify without a tax hit, and coordinate the timing.
When Your RSUs Vest, Your 10b5-1 Plan Decides the Tax Bill
A 10b5-1 plan schedules your RSU sales. But the cost basis method, AMT timing, and wash sale risks it never checks all change what you owe. Here's how the mechanics work.
Your RSUs Are the Biggest Bet You Didn't Choose
Most of your net worth in one stock? Here's how a multi-year plan to diversify works without triggering a tax catastrophe. A senior tech executive's walkthrough.
Augusta Rule Documentation: 3 Steps to Tax-Free Rent in 2026
Collect up to $14,000+ in tax-free rent under the Augusta Rule — but only with proper documentation. Here are 3 must-have records your business needs to keep.
From San Diego to Frisco: How Moving States Could Save You $130K+ a Year
How high earners save $130K+/year relocating from CA to TX. Real numbers on state tax elimination, residency requirements, and strategies most moves miss.
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