Depending on the type of stock options you are granted (ISOs vs NSOs), the stage of your company (early vs late), and your employment status (new hire, employed, or departed), there are a number of ways to reduce potential stock option taxes. From taking advantage of specific IRS filings to simple tips and tricks, you can potentially reduce your stock option exercise taxes significantly.

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The below list is a compilation of 17 different methods:

• Exercise early and File an 83(b) Election
• Exercise and Hold for Long Term Capital Gains
• Exercise Just Enough Options Each Year to Avoid AMT
• Exercise ISOs In January to Maximize Your Float Before Paying AMT
• Get Refund Credit for AMT Previously Paid on ISOs
• Reduce the AMT on the ISOs by Exercising NSOs
• Split your ISO Exercises between December and January
• AMT Disqualifying Disposition
• Move Stock to an Individual Retirement Account (IRA)
• Exercise options in a Qualified Small Business
• Minimize Medicare Taxes by Investing before an Exit
• File an 83(i) Election to defer NSO taxes for 5 years
• Execute a Swap Exercise
• Roll your Capital Gains into an Opportunity Zone Fund
• Move to a Lower State Tax Jurisdiction (Remote / WFH Flexibility)
• Defer Capital Gains Tax via a Deferred Sale Trust
• Reduce NSO Exercise Taxes through a Charitable Contribution of a Conservation Easement

If you hold employee stock options or restricted shares in a private company funded by institutional venture capital, feel free to contact us at ESO Fund for more information on how we can assist you. By doing so, you can not only avoid the risks associated with investing directly in a startup but possibly improve your taxes as well. For specific tax related support related to stock option exercises, please contact Scott Chou.

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Check out ESO Fund's AMT Calculator to help determine your AMT liability. For help funding exercise related taxes, check out how ESO Fund can cover your taxes risk-free.