FIRST AMENDMENT TO SECURITY AGREEMENT (Subsidiary)

Exhibit 10.5

FIRST AMENDMENT

TO SECURITY AGREEMENT

(Subsidiary)

This FIRST AMENDMENT TO SECURITY AGREEMENT (this “Amendment”) is made as of the 23 ^rd  day of February, 2009 among:

(a) MEDIABISTRO.COM INC., a Delaware corporation (“Pledgor”); and

(b) KEYBANK NATIONAL ASSOCIATION, as administrative agent for the benefit of the Lenders, as hereinafter defined (“Agent”).

WHEREAS, JUPITERMEDIA CORPORATION, a Delaware corporation, to be known as WebMediaBrands Inc. (“Borrower”), entered into that certain Credit and Security Agreement, dated as of July 12, 2007, with the lenders named therein (the “Lenders”), Agent, and Citizens Bank, N.A., as the syndication agent (as amended, the “Credit Agreement”);

WHEREAS, in connection with the Credit Agreement, Pledgor and Agent entered into that certain Security Agreement, dated as of July 30, 2007 (as the same may from time to time be amended, restated or otherwise modified, the “Security Agreement”);

WHEREAS, Borrower and KeyBank National Association, in its own capacity and not as agent for the Lenders (“KeyBank”), entered into that certain hedge agreement, the terms and conditions of which are governed by that certain 1992 ISDA Master Agreement between Borrower and KeyBank, dated as of July 19, 2007 (the “Master Agreement”), and evidenced by that certain Confirmation between Borrower and KeyBank, dated as of July 19, 2007, executed in accordance with the Master Agreement (collectively, the “Swap Agreement”);

WHEREAS, on the date hereof, Borrower is terminating the Commitment under the Credit Agreement, pursuant to the terms of that certain Payoff Letter, dated as of February 23, 2009, from Agent, and acknowledged and agreed to by Borrower;

WHEREAS, notwithstanding the termination of the Credit Agreement, the obligations under the Swap Agreement (together with any other obligations owing to KeyBank under the Master Agreement, collectively, the “Swap Obligations”) that are currently secured pursuant to the Credit Agreement (and certain other security documents executed in connection therewith, including the Security Agreement) will be permitted to remain outstanding after the termination of the Credit Agreement;

WHEREAS, Pledgor and Agent desire to amend the Security Agreement so that the Security Agreement only continues to secure the Swap Obligations;

WHEREAS, each capitalized term used herein and defined in the Security Agreement, but not otherwise defined herein, shall have the meaning given such term in the Security Agreement; and

WHEREAS, unless otherwise specifically provided herein, the provisions of the Security Agreement revised herein are amended effective as of the date of this Amendment;

NOW, THEREFORE, in consideration of the premises and of the mutual covenants herein and for other valuable consideration, Pledgor and Agent agree as follows:

1. Amendment to Introductory Paragraph . The introductory paragraph of the Security Agreement is hereby amended to delete therefrom the phrase “as administrative agent under the Credit Agreement, as hereinafter defined”, and to insert in place thereof the phrase “as administrative agent for itself and any other Persons that participate in the Swap Obligations”.

2. Amendment to Recitals . Section 1 of the Security Agreement is hereby amended to delete Section 1 therefrom and to insert in place thereof the following:

1. Recitals .

JUPITERMEDIA CORPORATION, a Delaware corporation, to be known as WebMediaBrands, Inc. (“Borrower”), has entered into that certain ISDA Master Agreement, dated as of July 19, 2007, with KeyBank (as the same may from time to time be amended, restated or otherwise modified, the “Master Agreement”), as evidenced by that certain Confirmation, dated as of July 19, 2007, executed in accordance with the Master Agreement (the “Confirmation”, and together with the Master Agreement, collectively, the “Swap Agreement”).

Pledgor, a subsidiary of Borrower, deems it to be in the direct pecuniary and business interests of Pledgor that Borrower continue to obtain from the Lenders, as hereinafter defined, the financial accommodations provided for in the Swap Agreement.

Pledgor understands that the Lenders are willing to continue to grant such financial accommodations to Borrower only upon certain terms and conditions, one of which is that Pledgor continue to grant to Agent, for the benefit of the Lenders, a security interest in and collateral assignment of the Collateral, as hereinafter defined, and this Agreement is being executed and delivered in consideration of the Lenders continuing to grant the financial accommodations provided for under the Swap Agreement and for other valuable consideration.

3. Amendment to the Introductory Clause of Section 2 . Section 2 of the Security Agreement is hereby amended to delete the introductory clause therefrom and to insert in place thereof the following:

“Except as specifically defined herein, terms that are defined in the U.C.C. are used herein as so defined. As used in this Agreement, the following terms shall have the following meanings:”

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4. Amendment to Definitions . Section 2 of the Security Agreement is hereby amended to delete the definitions of “Immaterial Deposit Account”, “Obligations” and “Proceeds” therefrom, and to insert in place thereof, respectively, the following:

“Immaterial Deposit Account” means a Deposit Account maintained by Pledgor or Borrower that at all times, has a balance of less than One Hundred Thousand Dollars ($100,000); provided that the Immaterial Deposit Accounts of Pledgor and Borrower shall not, at any time, aggregate in excess of One Hundred Thousand Dollars ($100,000).

“Obligations” means, collectively, (a) all present and future obligations and liabilities of any kind incurred by Borrower pursuant to the Swap Agreement, including all Transactions, as defined in the Swap Agreement, entered into thereunder and all termination values, expenses and damages payable in accordance with the terms thereof; (b) interest from time to time accruing on any of the foregoing, and all fees and other amounts payable by Borrower pursuant to the Swap Agreement or any other Loan Document; and (c) all Related Expenses.

“Proceeds” means (a) proceeds as defined in the U.C.C., and any other proceeds, and (b) whatever is received upon the sale, exchange, collection or other disposition of Collateral or proceeds, whether cash or non-cash. Cash proceeds include, without limitation, moneys, checks and Deposit Accounts. Proceeds include, without limitation, any Account arising when the right to payment is earned under a contract right, any insurance payable by reason of loss or damage to the Collateral, and any return or unearned premium upon any cancellation of insurance. Except as expressly authorized in this Agreement, the right of Agent and the Lenders to Proceeds specifically set forth herein or indicated in any financing statement shall never constitute an express or implied authorization on the part of Agent or any Lender to a Company’s sale, exchange, collection or other disposition of any or all of the Collateral.

5. Additions to Definitions . Section 2 of the Security Agreement is hereby amended to add the following new definitions thereto:

“Business Day” means any day that is not a Saturday, a Sunday or another day of the year on which national banks are authorized or required to close in Cleveland, Ohio or New York, New York.

“Companies” means Borrower and all Subsidiaries of Borrower.

“Company” means Borrower or a Subsidiary of Borrower.

“Default Rate” means the Default Rate, as defined in the Swap Agreement.

“Foreign Subsidiary” means a Subsidiary of Pledgor that is organized under the laws of any jurisdiction other than the United States, any State thereof or the District of Columbia.

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“Governmental Authority” means any nation or government, any state, province or territory or other political subdivision thereof, any governmental agency, department, authority, instrumentality, regulatory body, court, central bank or other governmental entity exercising executive, legislative, judicial, taxing, regulatory or administrative functions of or pertaining to government, any securities exchange and any self-regulatory organization exercising such functions.

“KeyBank” means KeyBank National Association, a national banking association, and its successors and assigns.

“Lender” or “Lenders” means KeyBank.

“Lien” means any mortgage, deed of trust, security interest, lien (statutory or other), charge, assignment, hypothecation, encumbrance on, pledge or deposit of, or conditional sale, leasing (other than operating leases), sale with a right of redemption or other title retention agreement and any capitalized lease with respect to any property (real or personal) or asset.

“Loan Documents” means, collectively, this Agreement, the Swap Agreement, any documents executed in connection with the Swap Agreement, and any documents that secure the Swap Agreement, and any document executed by Borrower in connection with obligations that are secured by the security interest granted under this Agreement; as any of the foregoing may from time to time be amended, restated or otherwise modified or replaced, and any other document delivered pursuant thereto.

“Person” means any individual, sole proprietorship, partnership, joint venture, unincorporated organization, corporation, limited liability company, unlimited liability company, institution, trust, estate, Governmental Authority or any other entity.

“Related Expenses” means any and all costs, liabilities and expenses (including, without limitation, losses, damages, penalties, claims, actions, attorneys’ fees, legal expenses, judgments, suits and disbursements) (a) incurred by Agent, or imposed upon or asserted against Agent or any Lender, in any attempt by Agent and the Lenders to (i) enforce this Agreement, the Swap Agreement or any Related Writing, or to obtain, preserve or perfect any security interest evidenced by this Agreement, the Swap Agreement or any Related Writing; (ii) obtain payment, performance or observance of any and all of the Obligations; or (iii) maintain, insure, audit, collect, preserve, repossess or dispose of any of the collateral securing the Obligations or any part thereof, including, without limitation, costs and expenses for appraisals, assessments and audits of any Company or any such collateral; or (b) incidental or related to (a) above, including, without limitation, interest thereupon from the date incurred, imposed or asserted until paid at the Default Rate, as defined in the Swap Agreement.

“Related Writing” means each Loan Document and any other assignment, mortgage, security agreement, guaranty agreement, subordination agreement, financial statement, audit report or other writing furnished by Borrower, any guarantor of payment

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or any mortgagor, or any officers or agents of any of the foregoing, to Agent or the Lenders pursuant to or otherwise in connection with the Obligations.

“Subsidiary” means (a) a corporation more than fifty percent (50%) of the Voting Power of which is owned, directly or indirectly, by Pledgor or by one or more other subsidiaries of Pledgor or by Pledgor and one or more subsidiaries of Pledgor, (b) a partnership, limited liability company or unlimited liability company of which Pledgor, one or more other subsidiaries of Pledgor or Pledgor and one or more subsidiaries of Pledgor, directly or indirectly, is a general partner or managing member, as the case may be, or otherwise has an ownership interest greater than fifty percent (50%) of all of the ownership interests in such partnership, limited liability company or unlimited liability company, or (c) any other Person (other than a corporation, partnership, limited liability company or unlimited liability company) in which Pledgor, one or more other subsidiaries of Pledgor or Pledgor and one or more subsidiaries of Pledgor, directly or indirectly, has at least a majority interest in the Voting Power or the power to elect or direct the election of a majority of directors or other governing body of such Person.

“Voting Power” means, with respect to any Person, the exclusive ability to control, through the ownership of shares of capital stock, partnership interests, membership interests or otherwise, the election of members of the board of directors or other similar governing body of such Person. The holding of a designated percentage of Voting Power of a Person means the ownership of shares of capital stock, partnership interests, membership interests or other interests of such Person sufficient to control exclusively the election of that percentage of the members of the board of directors or similar governing body of such Person.

6. Amendment to Representations and Warranties . Section 4 of the Security Agreement is hereby amended to delete subsections 4.5 therefrom and to insert in place thereof the following:

4.5 Except with respect to the security interests previously granted to Agent, and except as set forth on Schedule 2 hereto, (a) there is no effective U.C.C. Financing Statement outstanding covering the Collateral, or any part thereof; (b) none of the Collateral is subject to any security interest or Lien of any kind; (c) the Internal Revenue Service has not alleged the nonpayment or underpayment of any tax by Pledgor or threatened to make any assessment in respect thereof; and (d) Agent has, for the benefit of the Lenders, a valid and enforceable first security interest in the Collateral (to the extent perfection can be accomplished by the filing of a U.C.C. Financing Statement) that is the type in which a security interest may be created under the U.C.C. by the execution of a security agreement and perfected by the filing of a U.C.C. Financing Statement (other than commercial tort claims). Pledgor does not own any Subsidiaries.

7. Amendment to Insurance . Section 5 of the Security Agreement is hereby amended to delete Section 5 therefrom and to insert in place thereof the following:

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5. Insurance . Pledgor shall at all times maintain insurance upon its Inventory, Equipment and other personal and real property with financially sound and reputable insurance companies in at least such amounts and against at least such risks as are generally insured against in the same general area by companies engaged in the same or similar business, with provisions reasonably satisfactory to Agent for payment of all casualty losses thereunder to Agent, for the benefit of the Lenders, and Pledgor as their interests may appear (loss payable endorsement in favor of Agent, for the benefit of the Lenders), and, if required by Agent, Pledgor shall deposit the policies with Agent. Any such policies of insurance shall provide for no fewer than thirty (30) days prior written notice of cancellation to Agent and the Lenders. Any sums received by Agent in payment of insurance losses, transfers or takings under the policies, where the sums received from such loss, transfer or taking are in excess of One Million Dollars ($1,000,000) (“Insurance Funds”), shall be held by Agent, in an account at KeyBank in Pled