0000950123-05-015383 Sample Contracts

GUARANTEE
Guarantee • December 30th, 2005 • Ipayment Inc • Services-business services, nec • New York

Guarantee, dated as of December 27, 2005 (this “Guarantee”), by Carl A. Grimstad (the “Guarantor”) in favor of iPayment, Inc. (the “Guaranteed Party”).

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AGREEMENT AND PLAN OF MERGER AMONG iPAYMENT HOLDINGS, INC., iPAYMENT MERGERCO, INC. AND iPAYMENT, INC. Dated as of December 27, 2005
Agreement and Plan of Merger • December 30th, 2005 • Ipayment Inc • Services-business services, nec • New York

This AGREEMENT AND PLAN OF MERGER is dated as of December 27, 2005 (as amended, modified or supplemented from time to time, this “Agreement”), among iPAYMENT HOLDINGS, INC., a corporation organized under the laws of Delaware (“Parent”), iPAYMENT MERGERCO, INC., a corporation organized under the laws of Delaware and a wholly-owned subsidiary of Parent (“MergerCo”), and iPAYMENT, INC., a corporation organized under the laws of Delaware (the “Company”).

JOINT FILING AGREEMENT
Joint Filing Agreement • December 30th, 2005 • Ipayment Inc • Services-business services, nec

Pursuant to Rule 13d-1(k)(1) promulgated under the Securities Exchange Act of 1934, as amended, the undersigned agree that the statement on Schedule 13D to which this exhibit is attached is filed on behalf of each of them.

EXCHANGE AGREEMENT
Exchange Agreement • December 30th, 2005 • Ipayment Inc • Services-business services, nec • New York

This Exchange Agreement (this “Agreement”) is made and entered into as of December 27, 2005, among iPayment Holdings, Inc., a Delaware corporation (“Parent”), Gregory S. Daily (“GSD”), and Carl A. Grimstad (“CAG”).

Form of Side Letter
Ipayment Inc • December 30th, 2005 • Services-business services, nec

Reference is made to the Exchange Agreement (the “Exchange Agreement”), dated as of the date hereof, between iPayment Holdings, Inc. (“Parent”), Gregory S. Daily (“GSD”) and Carl A. Grimstad (“CAG”), pursuant to which each of GSD and CAG has agreed, subject to the terms and conditions set forth in the Exchange Agreement, to (i) contribute all of his shares of common stock (“Company Stock”) of iPayment, Inc. (the “Company”) to Parent in exchange for shares of common stock (“Parent Stock”) of Parent and (ii) cause certain other persons to contribute shares of Company Stock to Parent in exchange for shares of Parent Stock.

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