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Handling of a combined accelerated vesting and repurchase of restricted stock

I have a couple of questions about how to handle the termination of a restricted stock agreement related to some consulting work in did in 2017 and 2018:

1) In 2017, I started consulting for a startup, compensation for which involved a restricted stock purchase agreement.

2) For 2017, I made a Section 83(b) election, and paid taxes on the fair market value of the restricted stock compensation, as ordinary income.

3) In 2018, due to a business conflict of interest, the restricted stock purchase agreement was terminated, in the following manner:

3.1) For about 5.5% of the restricted stock grant, in recognition of services performed to date, vesting was accelerated, and those shares were granted outright.

3.2) For the remaining restricted stock, the company exercised its right of repurchase, and purchased them at the original estimated fair market value.

So the questions I had were:

a) Since I haven't sold any of the vested stock, would I need to report anything relating to the vesting on my taxes for 2018?

b) Since with the Section 83(b) election, I already paid taxes on the fair market value of the full set of restricted stock in 2017, would I need to report and pay taxes on the amount paid for repurchasing the non-vested shares in 2018?

Any information that anyone could provide, or points to appropriate publications, would be greatly appreciated.

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1 Reply
DDollar
Expert Alumni

Handling of a combined accelerated vesting and repurchase of restricted stock

You need to report the sale of the shares that were repurchased, even though the cost basis and the proceeds will be the same, and therefore no gain or loss.  If you haven't sold or surrendered the "5.5%" shares that were granted, then there is nothing to report.

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