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Question

Should I sell all my company stock immediately when the lockup expires?

Answer

Selling everything at once can trigger a massive tax bill, expose you to market timing risk, and lead to regret. Build a multi-year plan that staggers sales over several years to smooth out taxes, reduce timing risk, and align with your personal financial goals.

Related FAQs

Self-managing post-IPO wealth or working with an advisor: which is better?

Selling all at once or staggering sales: which approach is better?

RSUs or ISOs: which has better tax treatment?
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Last Updated May 20, 2026
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