Bootstrap Structure Case Study

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I. Tax Impacts of “Bootstrap” Structure
The so called “bootstrap” acquisition is a modified straight stock sale where the purchaser of the ownership interest only purchases a portion of that which is outstanding and the remaining portion is redeemed by the entity itself. This type of transaction will leave the purchaser with complete ownership of the target organization for a lower cost. Both the sale and redemption are allowed to receive sale or exchange treatment, leaving the owners in the same tax position after the transaction as if it had been completed as a straight stock sale. To receive sale or exchange treatment, the redemption must be part of a plan that will completely eliminate the selling shareholder’s interest in the corporation. IRC § 302; Zens v. Quinlivan, 213 F.2d 914 (6th Cir. 1954); Rev. Rule 75-447, 1975-2 C.B. 113.
The owners of a corporation that is transferred through a bootstrap acquisition must recognize capital gain to the extent the total consideration received exceeds their basis in the corporation’s stock. I.R.C. § 302. Here, Doug has received $6.3 million from Olson and $2.7 million from Circle in return for his entire ownership interest in the company. With
I.R.C. § 368(a)(1)(C). The only restriction on the amount of consideration other than voting stock that applies is “continuity of interest” requirement mentioned above requirements at least forty to fifty percent of the total consideration paid in the transaction be the voting stock. Treas. Reg. § 1.368-1(e)(1); Miller, 84 F.2d 415; Rev. Proc. 77-37, 1977 C.B. 568. This means that the transaction can still be classified as a tax-free reorganization even though a substantial portion of the consideration paid is property other than

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