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