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EXHIBIT 10.38 REDEMPTION AND RECAPITALIZATION AGREEMENT

Recapitalization Agreement

EXHIBIT 10.38 REDEMPTION AND RECAPITALIZATION AGREEMENT | Document Parties: GOLDLEAF FINANCIAL SOLUTIONS INC. You are currently viewing:
This Recapitalization Agreement involves

GOLDLEAF FINANCIAL SOLUTIONS INC.

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Title: EXHIBIT 10.38 REDEMPTION AND RECAPITALIZATION AGREEMENT
Governing Law: New York     Date: 4/26/2006
Industry: Business Services     Law Firm: Simpson Thacher     Sector: Services

EXHIBIT 10.38 REDEMPTION AND RECAPITALIZATION AGREEMENT, Parties: goldleaf financial solutions inc.
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                                                                   EXHIBIT 10.38

                    REDEMPTION AND RECAPITALIZATION AGREEMENT

         This Redemption and Recapitalization Agreement (the "Agreement") is
entered into this April 25, 2006 by and between Lightyear PBI Holdings, LLC, a
Delaware limited liability company ("Investor"), and Private Business, Inc., a
Tennessee corporation ("Company").

         WHEREAS, Investor is the holder of 21,012.5 shares of the Company's
Series A Preferred Stock (together with any additional shares of the Company's
Series A Preferred Stock issued as the result of payments in kind of dividends
for such securities after the date hereof, the "Series A Preferred Stock"),
10,000 shares of the Company's Series C Preferred Stock (together with any
additional shares of the Company's Series C Preferred Stock issued as the result
of payments in kind of dividends for such securities after the date hereof, the
"Series C Preferred Stock"), a warrant to purchase 16,000,000 shares of the
Company's common stock (the "Common Stock") at an exercise price of $1.25 per
share (the "Original Series A Warrant"); warrants to purchase 767,045 shares of
the Company's common stock at an exercise price of $1.25 (the "Series A PIK
Warrants" and, together with the Original Series A Warrant and any additional
warrants issued as the result of payments in kind of dividends for the Series A
Preferred Stock, the "Series A Warrants"); a currently exercisable warrant to
purchase 1,893,940 shares of Common Stock at an exercise price of $1.32 per
share (the "2006 Warrant"); and a warrant to purchase 1,893,939 shares of Common
Stock at an exercise price of $1.32 per share that becomes exercisable on June
9, 2007 (the "2007 Warrant" and, together with the Series A Preferred Stock, the
Series C Preferred Stock, the Series A Warrants and the 2006 Warrant, the
"Investor Securities"); and

         WHEREAS, Company desires to engage in an underwritten offering of its
common stock on substantially the terms set forth in the Registration Statement
on Form S-1 filed with the Securities Exchange Commission on April 25, 2006 (the
"Offering"), a portion of the proceeds of which will be used, along with newly
issued shares of Common Stock, to redeem all of the outstanding shares of Series
A Preferred Stock and Series C Preferred Stock, the 2006 Warrant, and the 2007
Warrant, and any additional securities issued as the result of payments in kind
of dividends for such securities after the date hereof as described herein, and
concurrently therewith, the Company intends to recapitalize the Series A
Warrants in a manner intended to qualify as a plan of reorganization with the
meaning of Section 368 of the Internal Revenue Code.

         NOW, THEREFORE, intending to be legally bound, the undersigned have
agreed as follows:

1.        REDEMPTION OF THE INVESTOR SECURITIES. Effective upon the Closing
         (which, for purposes of this Agreement, shall be defined as the receipt
         by Company of the net proceeds from the sale of its common stock in the
         Offering, the consummation of the transactions set forth below and the
         cancellation of the Investor guarantee as described in Section 5(a)(ii)
         hereof):

         (a)       Investor shall surrender to Company for cancellation all of
                  Investor's right, title and interest in and to the Series A
                  Preferred Stock and the Series C Preferred Stock (the
                  "Preferred Stock Redemption"). Company shall pay Investor at
                  Closing in immediately available funds the purchase price for
                  the Preferred Stock Redemption (the "Preferred Stock Purchase
                  Price"), which shall be calculated as follows:


                                        1
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                  (i)       an amount equal to: (A) the number of shares of
                           Series A Preferred Stock held by Investor at Closing,
                           multiplied by the Original Issue Purchase Price (as
                           defined in the Amended and Restated Designation of
                           Preferences, Limitations, and Relative Rights of
                           Series A Preferred Stock of Private Business, Inc.
                            (the "Series A Designations")); plus (B) all accrued
                           but unpaid dividends owed at Closing pursuant to the
                           Series A Designations on the shares of Series A
                           Preferred Stock held by Investor at Closing; plus

                  (ii)      an amount equal to: (A) the number of shares of
                           Series C Preferred Stock held by Investor at Closing,
                           multiplied by the Original Issue Purchase Price (as
                           defined in the Amended and Restated Designation of
                           Preferences, Limitations, and Relative Rights of
                           Series C Preferred Stock of Private Business, Inc.
                           (the "Series C Designations")); plus (B) all accrued
                           but unpaid dividends owed at Closing pursuant to the
                           Series C Designations on the shares of Series C
                            Preferred Stock held by Investor at Closing.

                  For the avoidance of doubt, a sample calculation of the
                  Preferred Stock Purchase Price is attached hereto as Exhibit
                  A.

         (b)       Investor shall surrender to Company for cancellation all of
                  Investor's right, title and interest in and to the Series A
                  Warrants (the "Series A Warrant Recapitalization"). The
                  securities to be delivered to Investor in exchange for the
                  Series A Warrants in the Series A Warrant Recapitalization
                  (the "Series A Warrant Recapitalization Securities") shall be
                  that number of newly issued shares of Common Stock equal to
                  Fourteen and 9/10ths Percent (14.9%) of the Fully Diluted
                  Common Stock as of the Closing, including the Series A Warrant
                  Recapitalization Securities, (as defined below). For purposes
                   of this Agreement, the Fully Diluted Common Stock as of the
                  Closing shall equal:

                  (i)       the number of shares of Common Stock issued and
                           outstanding immediately following the Closing,
                            excluding (A) the Investor Securities and (B) the
                           outstanding shares of the Company's Series B
                           Preferred Stock, which Company shall redeem within
                           sixty (60) days following the Closing; plus

                  (ii)      One Million Sixty Thousand Six Hundred and Six
                           (1,060,606) shares of Common Stock, representing the
                           amount agreed to by the parties as representing the
                           estimated number of shares to be issued pursuant to
                           existing acquisition earn-outs (which number of
                           shares shall be adjusted for any reverse stock split
                            that Company may effect at or prior to the Closing);
                           plus

                  (iii)     the number of shares of Common Stock allocable to the
                           issued and outstanding options to purchase Common
                           Stock as of the Closing (though there shall not then
                           be issued options exercisable for more than 7,714,680
                           shares of Common Stock), as calculated utilizing the
                            treasury stock repurchase method at the price at
                           which shares of Common Stock are sold in the
                           Offering. For the avoidance of doubt, a sample
                           calculation of the treasury stock repurchase method
                           is attached hereto as Exhibit B.


                                       2

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                  The shares of Common Stock issued to Investor as the Series A
                  Warrant Recapitalization Securities shall be restricted from
                  transfer for a period of eighteen (18) months from Closing
                  (the "Restricted Period") pursuant to the terms of a stock
                  restriction agreement (the "Stock Restriction Agreement"), the
                  form of which shall be agreed to by Investor and Company prior
                  to Closing. Investor is acquiring such shares of Common Stock
                  for its own account and not with a view to their distribution
                  within the meaning of Section 2(11) of the Securities Act of
                  1933, as amended (the "Securities Act"). Investor acknowledges
                  that it is an accredited investor as that term is defined in
                  Rule 501(a) promulgated under the Securities Act, and that
                  such shares of Common Stock have not been registered under the
                  Securities Act or any blue sky laws.

                  Furthermore, the certificates evidencing the shares of Common
                  Stock issued as the Series A Warrant Recapitalization
                  Securities will bear a legend substantially similar to the
                  following:

                           The shares represented by this certificate have not
                           been registered under the Securities Act of 1933, as
                           amended (the "Act") or state securities laws and
                           cannot be offered, sold or otherwise transferred in
                           the absence of registration or the availability of an
                           exemption from registration under the Act and
                           regulations promulgated thereunder and applicable
                            state securities laws. Furthermore, the shares
                           represented by this certificate are subject to
                           certain restrictions on transfer as set forth in a
                           Stock Restriction Agreement, a copy of which is
                           available from the Company upon request.

         (c)       Investor shall surrender to Company for cancellation all of
                  Investor's right, title and interest in and to the 2006
                  Warrant (the "2006 Warrant Redemption"). The purchase price
                  for the 2006 Warrant Redemption (the "2006 Warrant Purchase
                  Price") shall be One Million Two Hundred Thousand Dollars
                  ($1,200,000), payable by Company at Closing in immediately
                  available funds.

         (d)       The 2007 Warrant shall be cancelled without further action in
                  accordance with its terms based upon the redemption of the
                   Series C Preferred Stock.

2.        TERMINATION OF RIGHTS, OBLIGATIONS, DEBTS AND AGREEMENTS.

         (a)       At Closing, and with the exception of any rights, obligations,
                  debts or agreements created by the terms of this Agreement and
                  the Stock Restriction Agreement, all rights, obligations,
                  debts, and agreements, whether or not matured or asserted,
                  between Investor and Company shall be cancelled, terminated
                   and of no further effect including, but not limited to, the
                  following:

                  (i)       termination of the following agreements, together
                           with termination of all rights, obligations, debts
                            and agreements arising thereunder: the Amended and
                           Restated Securities Purchase Agreement dated December
                           24, 2003, between Company and Investor; the Warrant
                            Agreement dated January 20, 2004, by and among
                           Company and Investor; subject to clause (b) below,
                           the Securityholders Agreement dated January 20, 2004,
                           by and among Company and Investor (the
                           "Securityholders Agreement"); the Guaranty Side
                           Letter dated January 23, 2006

                                       3
<PAGE>
                           between Company, Investor, and The Lightyear Fund,
                           L.P.; the Exchange Agreement dated January 23, 2006
                           between Company and Investor; the Amended and
                           Restated Warrant Agreement dated January 23, 2006
                            between Company and Investor; the Securities Purchase
                           Agreement dated December 9, 2005 between Company and
                           Investor; and each and every certificate representing
                            shares of Series A Preferred Stock, shares of Series
                           C Preferred Stock, or warrants issued pursuant to any
                           of the foregoing agreements; and


                  (ii)      termination of all rights, obligations, debts and
                           agreements arising under each of the Series A
                           Designations and the Series C Designations.

         (b)       The Securityholders Agreement will be amended in a form
                   reasonably acceptable to the Investor and the Company to
                  eliminate all of Investor's rights thereunder except a single
                  demand registration right and unlimited piggyback registration
                  rights, each of which shall only be exercisable after the
                  Restricted Period (with the exception of a single exercise of
                  the piggyback registration rights, which shall be exercisable
                  during the Restricted Period), all on substantially the same
                  terms as are set forth in the Securityholders Agreement.

         (c)       Investor hereby waives its registration rights and pre-emptive
                  rights associated with the Offering.

3.        INVESTOR COVENANTS.

         (a)       Prior to the Closing, Investor irrevocably and unconditionally
                  agrees that at any meeting (whether annual or special, and at
                  each adjourned or postponed meeting) of the shareholders of
                  Company, however called, Investor will (i) appear at each such
                  meeting or otherwise cause its shares of Common Stock, Series
                  A Preferred Stock and Series C Preferred Stock to be counted
                   as present thereat for purposes of calculating a quorum, and
                  (ii) vote, or cause to be voted at such meeting, all of
                  Investor's shares of Common Stock, Series A Preferred Stock
                  and Series C Preferred Stock (A) to approve the reverse stock
                  split as described in Proposal 3 of the Company's proxy
                  statement dated April 13, 2006, (B) to approve any proposal
                  required to be made to the shareholders of Company to
                  facilitate the Offering or any transaction by which Company
                  raises the equity and/or debt required to consummate the
                  transactions contemplated in this Agreement, (C) against any
                   proposal made in opposition to, or in competition or
                  inconsistent with, the transactions expressly contemplated by
                  this Agreement, and (D) against any liquidation or winding up
                  of Company.

         (b)       Following the Closing, David Glenn shall remain on the board
                  of directors of Company as the sole remaining director
                  affiliated with Investor (such remaining director shall be
                  referred to as the "Investor Director"), it being understood
                  that this provision shall not impact the continued service of
                  directors McCabe and Hough who are not affiliates of Investor.

4.        COMPANY COVENANTS. Following the Closing, Company shall take such
         actions as may be required under applicable law to cause the board of
         directors of Company (including any nominating committee thereof) to
         nominate and elect the Investor Director to continue to serve on the
         board of directors of Company until the earlier of (a) the resignation
         of the Investor Director o


 
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