Exhibit 10.1

EIGHTH AMENDMENT TO AMENDED AND RESTATED
LOAN AND SECURITY AGREEMENT

     THIS EIGHTH AMENDMENT TO AMENDED AND RESTATED LOAN AND SECURITY AGREEMENT
(this “Agreement”) is entered into as of July 1, 2004, by and among SILICON
VALLEY BANK, a California chartered bank, doing business in Virginia as “Silicon
Valley East” (“Bank”) with its principal place of business at 3003 Tasman Drive,
Santa Clara, California 95054 and with a loan production office located at 8020
Towers Crescent Drive, Suite 475, Vienna, Virginia 22182, (ii) BLACKBOARD INC.,
a Delaware corporation, having an address at 1899 L Street, N.W., Washington,
D.C. 20036 (“Company”), BLACKBOARD ACQUISITION COMPANY, LLC, a Delaware limited
liability company having an address at 1899 L Street, N.W., Washington, D.C.
20036 (“Blackboard Acquisition”), BLACKBOARD CAMPUSWIDE, INC., a Delaware
corporation, BLACKBOARD ICOLLEGE, INC., a Delaware corporation having an address
at 1899 L Street, N..W., Washington, D.C. 20036, BLACKBOARD CAMPUSWIDE OF TEXAS,
INC., (formerly known as AT&T Campuswide Access Solutions Of Texas, Inc.), a
Texas corporation having an address at 1899 L Street, N.W., Washington, D.C.
20036, and BB ACQUISITION CORP., a Delaware corporation, having an address at
1899 L Street, N.W., Washington, D.C. 20036 (each a “Borrower” and collectively,
the “Borrowers”).

RECITALS.

     A.     The Borrowers and Bank are all parties to that certain Amended and
Restated Loan and Security Agreement dated November 30, 2001, but effective as
of October 5, 2001, as amended by that certain First Amendment to Amended and
Restated Loan and Security Agreement dated as of January 11, 2002 among
Borrowers and Bank, that certain Second Amendment to Amended and Restated Loan
and Security Agreement dated as of October 4,

 

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2002 among Borrowers and Bank, that certain Third Amendment to Amended and
Restated Loan and Security Agreement dated as of February 17, 2003 among
Borrowers and Bank, that certain Fourth Amendment to Amended and Restated Loan
and Security Agreement dated effective as of May 28, 2003 among Borrowers and
Bank, that certain Fifth Amendment to Amended and Restated Loan and Security
Agreement dated as of June 30, 2003 among Borrowers, Bank and certain affiliates
of Borrowers that were made “Borrowers” under the Amended and Restated Loan and
Security Agreement and subsequently removed as “Borrowers” under the Amended and
Restated Loan Documents, that certain Sixth Amendment to Amended and Restated
Loan and Security Agreement dated as of July 25, 2003 among Borrowers and Bank
and that certain Seventh Amendment to Amended and Restated Loan and Security
Agreement dated as of April 4, 2004 between Borrowers and Bank (as the same may
be amended from time to time, the “Loan Agreement”), pursuant to which Bank has
agreed to establish (i) a revolving line of credit in the maximum principal
amount of Eight Million Dollars ($8,000,000) to be used by Borrowers for working
capital needs and general corporate purposes, (ii) an equipment line of credit
in the maximum principal amount of Three Million Dollars ($3,000,000) to be used
by the Borrowers for the purchase of equipment, and (iii) an equipment line of
credit in the maximum principal amount of One Million Five Hundred Thousand
Dollars ($1,500,000) to be used by the Borrowers for the purchase of equipment,
all as more fully described in the Loan Agreement.

     B.      The Borrowers have requested that Bank amend certain provisions of
the Loan Agreement and Bank has agreed on the condition, among others, that
Borrowers execute and deliver this Agreement.

     C.      All capitalized terms used herein and not otherwise defined shall
have the meanings given to such terms in the Loan Agreement.

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     NOW, THEREFORE, in consideration of the foregoing, and for other good and
valuable consideration, the receipt and sufficiency of which is hereby
acknowledged, Borrowers and Bank do hereby agree as follows:

     1.      Recitals. The parties hereto acknowledge and agree that the above
Recitals are true and correct in all material respects and that the same are
incorporated herein and made a part hereof by reference.

     2.      Definitions. From and after the date hereof, the definitions of
Revolving Maturity Date set forth in Section 13.1 of the Loan Agreement is
hereby amended and restated in its entirety as follows:

     "Revolving Maturity Date” is August 30, 2004.

     3.      Facility Fee. Borrowers shall pay to Bank on the date hereof a loan
fee on the Committed Revolving Line in the amount of Three Thousand Three
Hundred Dollars ($3,300) (the “Committed Revolving Line Fee”). The Committed
Revolving Line Fee is considered earned when paid and is not refundable.

     4.      Conditions Precedent. This Agreement shall become effective on the
date the Bank receives the following documents, each of which shall be
satisfactory in form and substance to the Bank:

          (a)      proof that Borrowers have paid all fees, costs and expenses
to Bank in connection with this Agreement, including but not limited to all the
Bank’s reasonable attorneys fees and expenses; and

          (b)      such other information, instruments, opinions, documents,
certificates and reports as the Bank may deem necessary.

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     5.      Counterparts. This Agreement may be executed in any number of
duplicate originals or counterparts, each of which duplicate original or
counterpart shall be deemed to be an original and all taken together shall
constitute one and the same instrument.

     6.      Loan Documents; Governing Law; Etc. This Agreement is one of the
Loan Documents defined in the Loan Agreement and shall be governed and construed
in accordance with the laws of the Commonwealth of Virginia. The headings and
captions in this Agreement are for the convenience of the parties only and are
not a part of this Agreement.

     7.      Acknowledgments. The Borrowers hereby confirm to the Bank the
enforceability and validity of each of the Loan Documents. In addition, the
Borrowers hereby agree that the execution and delivery of this Agreement and the
terms and provisions, covenants or agreements contained in this Agreement shall
not in any manner release, impair, lessen, modify, waive or otherwise limit the
liability and obligations of the Borrowers under the terms of any of the Loan
Documents, except as otherwise specifically set forth in this Agreement. Each
Person included in the term “Borrower” hereby issues, remakes, ratifies and
confirms the representations, warranties and covenants contained in the Loan
Documents on and as of the date hereof, both before and after giving effect to
this Agreement except as may be modified by the provisions of this Agreement,
and that no Event of Default or Default has occurred and is continuing or exists
or would occur or exist after giving effect to this Agreement. Nothing in this
Agreement shall be deemed to waive any defaults existing under any of the Loan
Documents as of the date hereof.

     8.      Modifications. This Agreement may not be supplemented, changed,
waived, discharged, terminated, modified or amended, except by written
instrument executed by the parties.

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     9.      Consistent Changes. The Loan Documents are hereby amended wherever
necessary to reflect the changes described above.

      

[SIGNATURES APPEAR ON FOLLOWING PAGE]

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     IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be
executed as of the date first above written.

                  WITNESS:       SILICON VALLEY BANK    
 
                /s/ David Steigerwald       By: /s/ Tony Wolfe   (SEAL)

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          Name: Tony Wolfe    

          Title: Vice President    
 
                WITNESS/ATTEST:       BLACKBOARD INC.    
 
                /s/ Matthew Small       By: /s/ Michael L. Chasen   (SEAL)

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          Michael L. Chasen    

          Chief Executive Officer    
 
                WITNESS/ATTEST:       BLACKBOARD ACQUISITION            
COMPANY, LLC             By: Blackboard Inc., its Member    
 
                /s/ Matthew Small       By: /s/ Michael L. Chasen   (SEAL)

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          Michael L. Chasen    

          President    
 
                WITNESS/ATTEST:       BLACKBOARD CAMPUSWIDE, INC.    
 
                /s/ Matthew Small       By: /s/ Michael L. Chasen   (SEAL)

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          Michael L. Chasen    

          President    
 
                WITNESS/ATTEST:       BLACKBOARD ICOLLEGE, INC.    
 
                /s/ Matthew Small       By: /s/ Michael L. Chasen   (SEAL)

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          Michael L. Chasen    

          President    

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                  WITNESS/ATTEST:       BLACKBOARD CAMPUSWIDE OF TEXAS, INC.
 
               
/s/ Matthew Small
      By:   /s/ Michael L. Chasen   (SEAL)

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          Michael L. Chasen    

          President    
 
                WITNESS/ATTEST:       BB ACQUISITION CORP.    
 
               
/s/ Matthew Small
      By:   /s/ Michael L. Chasen   (SEAL)

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          Michael L. Chasen    

          Chief Executive Officer    

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