Tax Strategy Blog
Actionable strategies for real estate investors, business owners, and high earners — written by the Roadmap Tax team.
Your RSUs Vested This Quarter. Here's Why the Tax Bill Comes Due in January.
Your Q3 RSUs just vested. At 22% withholding, you're covering less than half the actual tax. Here's how to fix the gap before year-end while there's still time.
When You Sell RSU Shares, the Cost Basis Decides the Tax Bill
Your RSUs were taxed at vesting. If your 1099-B shows a zero or missing cost basis, you pay tax twice unless you adjust it on Form 8949. Step-by-step fix.
The Three-Year Plan to Diversify Your RSUs: A Walkthrough
Avoid concentration risk with a clear, year-by-year RSU diversification plan. See exactly when to sell, what to buy, and how to stay tax-efficient.
How California Still Taxes Your RSUs After You Move
Moved out of California but still owe RSU tax? How state sourcing works, why the FTB sends letters, and how to plan your move.
When Your RSUs Vest, the Withholding Probably Isn't Enough
Your RSUs may be withheld at 22%, but you could owe far more. Learn how to plan ahead and avoid a surprise tax bill at filing.
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
Your 10b5-1 plan schedules RSU sales but ignores cost basis, AMT timing, and wash sale risks. Each one changes what you owe. Fix the gaps before tax season.
Your RSUs Are the Biggest Bet You Didn't Choose
Most of your net worth in one stock? How a multi-year plan to diversify RSUs without a tax catastrophe. Walkthrough for tech executives.
Augusta Rule Documentation: 3 Steps to Tax-Free Rent in 2026
The 5 documents you need to survive an Augusta Rule audit: meeting minutes, fair rental comps, payment records, and more. Complete checklist.
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.
Talk to a strategist