Got Stock Options? Don’t Miss These Year-End Tax Moves With Ally Jane Ayers (EP.182)

The Long Term Investor

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Navigating equity compensation can be tricky, especially when the year-end tax clock is ticking.

In this episode, Ally Jane Ayers, a leading expert in the complex world of equity compensation, shares tax-smart strategies to optimize your stock options, RSUs, and equity packages. Whether you hold RSUs, ISOs, or stock options at a private company, Ally’s insights will help you tackle tricky tax issues, reduce over-concentration risks, and align your equity with your financial goals.

Listen now and learn:

• Key tax considerations for equity compensation before December 31
• How to avoid costly under-withholding on RSUs.
• Advanced strategies to diversify concentrated stock positions and preserve gains.
• The power of 10b5-1 plans for stress-free stock selling.

Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.

(00:37) Key Tax Considerations for Year-End Stock Compensation Planning

(03:54) The Importance of Multiyear Equity Planning

(09:24) Exercising Stock Options at Private Companies

(14:10) Managing Risk with Equity Compensation

(22:27) Advanced Strategies for Managing Mixed Equity Packages

(25:38) Creative Ways to Preserve Gains and Minimize Taxes

(32:49) Leveraging 10b5-1 Plans for Stress-Free Selling

(34:56) Final Tips for Equity Compensation Holders