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I was taxed at the time of my grant, and then again on the gain when I sell. Had I put them in a self directed IRA i could have bypassed 6 figures of cap gains tax.

You can’t contribute in-kind to an IRA.

Actually that’s a great point. Depending on your company and your role in the company I’m sure there are ways to get around that, but that would require your company to play ball and get creative with you.

The ole mitt Romney.

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