He had years of vested RSUs and a position that had quietly come to dominate his portfolio. He knew it was too concentrated, but he wouldn’t sell, because he was sure the tax bill would be brutal. On most of his shares, it wasn’t.

In this video, the advisor breaks down:
• Why RSUs are taxed as ordinary income at vesting — so the income tax is already paid
• How cost basis resets at vest, making freshly vested shares nearly tax-free to sell
• The “two-speed” reality: which shares to sell now vs. which to hold and time
• Why waiting to sell appreciated shares for a lower-bracket year is genuinely smart planning
• The plan we built: selling low-gain lots first, a 10b5-1 schedule for future vests, gain-budgeting, and a donor-advised fund for the lowest-basis shares

Tom is a composite archetype, not a real client, used to illustrate planning issues common among senior technology professionals. This content is for educational purposes only and does not constitute financial, tax, or legal advice.

RADIANT Wealth Planning is a fee-only fiduciary firm working with technology professionals and executives across Silicon Valley and the Washington, D.C. area navigating equity compensation, concentrated stock, and the years approaching retirement.

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Schedule an introductory meeting with Randa or email Randa with any questions: Randa@RadiantWealthPlanning.com

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