Exhibit 10.4

GUARANTY OF PAYMENT

This GUARANTY OF PAYMENT (as the same may from time to time be amended, restated
or otherwise modified, this “Agreement”) is made as of the 12th day of July,
2007, by WORKBOOK, INC., a California corporation (“Guarantor”), in favor of
KEYBANK NATIONAL ASSOCIATION, as the administrative agent under the Credit
Agreement, as hereinafter defined (“Agent”), for the benefit of the Lenders, as
hereinafter defined.

1. Recitals.

JUPITERMEDIA CORPORATION, a Delaware corporation (together with its successors
and assigns, “Borrower”), is entering into that certain Credit and Security
Agreement, dated as of July 12, 2007, with the lenders from time to time listed
on Schedule 1 thereto (together with their respective successors and assigns and
any other additional lenders that become party to the Credit Agreement,
collectively, the “Lenders” and, individually, each a “Lender”), Agent, and
Citizens Bank, N.A., as the syndication agent (as the same may from time to time
be amended, restated or otherwise modified, the “Credit Agreement”). Guarantor
desires that the Lenders grant the financial accommodations to Borrower as
described in the Credit Agreement. Except as specifically defined herein,
capitalized terms used herein that are defined in the Credit Agreement shall
have their respective meanings ascribed to them in the Credit Agreement.

Guarantor, a subsidiary of Borrower whose financing is provided by the Loans and
Letters of Credit, deems it to be in the direct pecuniary and business interests
of Guarantor that Borrower obtain from the Lenders the Commitment and the Loans
and Letters of Credit provided for in the Credit Agreement.

Guarantor understands that the Lenders are willing to enter into the Credit
Agreement only upon certain terms and conditions, one of which is that Guarantor
guarantee the payment of the Obligations, as hereinafter defined, and this
Agreement is being executed and delivered in consideration of the Lenders
entering into the Credit Agreement and for other valuable consideration.

2. Definitions. As used in this Agreement, the following terms shall have the
following meanings:

“Collateral” means, collectively, all property, if any, securing the Obligations
or any part thereof at the time in question.

“Obligations” means, collectively, (a) all Indebtedness and other obligations
incurred by Borrower to Agent, the Fronting Lender, the Swing Line Lender or any
Lender pursuant to the Credit Agreement, and includes the principal of and
interest on all Loans and all obligations pursuant to Letters of Credit;
(b) each extension, renewal or refinancing of any of the foregoing, in whole or
in part; (c) the commitment fees, any prepayment fees and any other fees payable
pursuant to the Credit Agreement, and all fees and charges in connection with
the Letters of

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Credit; and (d) every other liability, now or hereafter owing to Agent or any
Lender by any Obligor pursuant to the Credit Agreement or any other Loan
Document; and (e) all Related Expenses.

“Obligor” means Borrower or any other Credit Party.

3. Guaranty of the Obligations. Guarantor hereby absolutely and unconditionally
guarantees (as a guaranty of payment and not merely a guaranty of collection)
the prompt payment in full of all of the Obligations as and when the respective
parts thereof become due and payable. If the Obligations, or any part thereof,
shall not be paid in full when due and payable, Agent, on behalf of the Lenders,
in each case, shall have the right to proceed directly against Guarantor under
this Agreement to collect the payment in full of the Obligations, regardless of
whether or not Agent, on behalf of the Lenders, shall have theretofore proceeded
or shall then be proceeding against Borrower or any other Obligor or Collateral,
if any, or any of the foregoing, it being understood that Agent, on behalf of
the Lenders, in its sole discretion, may proceed against any Obligor and any
Collateral, and may exercise each right, power or privilege that Agent or the
Lenders may then have, either simultaneously or separately, and, in any event,
at such time or times and as often and in such order as Agent, on behalf of the
Lenders, in its sole discretion, may from time to time deem expedient to collect
the payment in full of the Obligations. Guarantor agrees that all payments made
by Guarantor under this Agreement shall be made free and clear of, and without
deduction or withholding for or on account of any Taxes or Other Taxes, in
accordance with Section 3.2 of the Credit Agreement.

4. Payments Conditional. Whenever Agent or any Lender shall credit any payment
to the Obligations or any part thereof, whatever the source or form of payment,
the credit shall be conditional as to Guarantor unless and until the payment
shall be final and valid as to all the world. Without limiting the generality of
the foregoing, Guarantor agrees that if any check or other instrument so applied
shall be dishonored by the drawer or any party thereto, or if any proceeds of
Collateral or payment so applied shall thereafter be recovered by any trustee in
bankruptcy or any other Person, each Lender, in each case, may reverse any entry
relating thereto on its books and Guarantor shall remain liable therefor, even
if such Lender may no longer have in its possession any instrument evidencing
the Obligations to which the payment in question was applied.

5. Guarantor’s Obligations Absolute and Unconditional. Regardless of the
duration of time, regardless of whether Borrower may from time to time cease to
be indebted to the Lenders and irrespective of any act, omission or course of
dealing whatever on the part of Agent or any Lender, Guarantor’s liabilities and
other obligations under this Agreement shall remain in full effect until the
payment in full of the Obligations. Without limiting the generality of the
foregoing:

5.1. Lenders Have No Duty to Make Advances. Without limiting the obligations of
Agent and the Lenders under the Credit Agreement, no Lender shall at any time be
under any duty to Guarantor to grant any financial accommodation to Borrower,
irrespective of any duty or commitment of any of the Lenders to Borrower, or to
follow or direct the application of the proceeds of any such financial
accommodation;

 

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5.2. Guarantor’s Waiver of Notice, Presentment. Guarantor waives (a) notice of
the granting of any Loan to Borrower, the issuance of any Letter of Credit or
the incurring of any other Indebtedness by Borrower or the terms and conditions
thereof, (b) presentment, demand for payment and notice of dishonor of the
Obligations or any part thereof, or any other Indebtedness incurred by Borrower
to any of the Lenders, (c) notice of any indulgence granted to any Obligor, and
(d) any other notice to which Guarantor might, but for this waiver, be entitled;

5.3. Lenders’ Rights Not Prejudiced by Action or Omission. Agent and the
Lenders, in their sole discretion, may, pursuant to the Credit Agreement,
without any prejudice to their rights under this Agreement, at any time or
times, without notice to or the consent of Guarantor, (a) grant Borrower
whatever financial accommodations that Agent and the Lenders may from time to
time deem advisable, even if Borrower might be in default in any respect and
even if those financial accommodations might not constitute Indebtedness the
payment of which is guaranteed hereunder, (b) assent to any renewal, extension,
consolidation or refinancing of the Obligations, or any part thereof,
(c) forbear from demanding security, if Agent and the Lenders shall have the
right to do so, (d) release any Obligor or Collateral or assent to any exchange
of Collateral, if any, irrespective of the consideration, if any, received
therefor, (e) grant any waiver or consent or forbear from exercising any right,
power or privilege that Agent and the Lenders may have or acquire, (f) assent to
any amendment, deletion, addition, supplement or other modification in, to or of
any writing evidencing or securing any of the Obligations or pursuant to which
any of the Obligations are created, (g) grant any other indulgence to any
Obligor, (h) accept any Collateral for, or any other Obligor upon, the
Obligations or any part thereof, and (i) fail, neglect or omit in any way to
realize upon any Collateral, to perfect any security interest with respect to
Collateral, or to protect the Obligations or any part thereof or any Collateral
therefor;

5.4. Liabilities Survive Guarantor’s Dissolution. Guarantor’s liabilities and
other obligations under this Agreement shall survive any dissolution of
Guarantor; and

5.5. Liabilities Absolute and Unconditional. Guarantor’s liabilities and other
obligations under this Agreement shall be absolute and unconditional
irrespective of any lack of validity or enforceability of the Credit Agreement,
any Note, any Loan Document or any other agreement, instrument or document
evidencing the Loans or Letters of Credit or related thereto, the existence of
any claim, set-off or other rights that Guarantor may have against Borrower or
any other Person, or any other defense available to Guarantor in respect of this
Agreement (other than the payment in full of the Obligations).

6. Representations and Warranties. Guarantor represents and warrants to Agent
and each of the Lenders that (a) Guarantor is a duly organized and validly
existing corporation, in good standing under the laws of the state of its
incorporation (as referenced in the first paragraph of this Agreement), and is
qualified to do business in each state where a failure to so qualify would have
a material adverse effect on Guarantor; (b) Guarantor has legal power and right
to execute and deliver this Agreement and to perform and observe the provisions
hereof; (c) the officers executing and delivering this Agreement on behalf of
Guarantor have been duly authorized to do so, and this Agreement, when executed,
is legal and binding upon Guarantor in

 

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every respect; (d) except for matters described or referenced in the Credit
Agreement or any Schedule thereto, no litigation or proceeding is pending or
threatened against Guarantor before any court or any administrative agency that,
in Guarantor’s opinion, after consultation with Guarantor’s counsel, is
reasonably expected to have a material adverse effect on Guarantor;
(e) Guarantor has received consideration that is the reasonable equivalent value
of the obligations and liabilities that Guarantor has incurred to Agent, for the
benefit of the Lenders; (f) Guarantor is not insolvent, as defined in any
applicable state or federal statute, nor will Guarantor be rendered insolvent by
the execution and delivery of this Agreement to Agent and the Lenders;
(g) Guarantor is not engaged or about to engage in any business or transaction
for which the assets retained by Guarantor are or will be an unreasonably small
amount of capital, taking into consideration the obligations to the Lenders
incurred hereunder; and (h) Guarantor does not intend to, nor does Guarantor
believe that Guarantor will, incur debts beyond Guarantor’s ability to pay such
debts as they mature.

7. Disability of Obligor. Without limiting the generality of any of the other
provisions hereof, Guarantor specifically agrees that upon the occurrence and
during the continuance of an Event of Default, Agent and the Required Lenders,
in their sole discretion (but subject to the terms of the Credit Agreement), may
declare the unpaid principal balance of and accrued interest on the Obligations
to be forthwith due and payable in full without notice. Upon the occurrence of
any of the events enumerated in the immediately preceding sentence, Guarantor
shall, upon demand of Agent, on behalf of the Lenders, whenever made, pay to
Agent, for the benefit of the Lenders, an amount equal to the then unpaid
principal balance of and accrued interest on the Obligations.

8. Waiver of Guarantor’s Rights Against Borrower and Collateral. To the extent
permitted by law, Guarantor hereby waives any claim or other right that
Guarantor might now have or hereafter acquire against Borrower or any other
Obligor that arises from the existence or performance of Guarantor’s liabilities
or other obligations under this Agreement, including, without limitation, any
right of subrogation, reimbursement, exoneration, contribution, indemnification,
and any right to participate in any claim or remedy of Agent or any Lender
against Borrower or any Collateral that Agent or any Lender now has or hereafter
acquires, whether or not such claim, remedy or right arises in equity, or under
contract, statute or common law.

9. Maximum Liability of Guarantor. Anything in this Agreement to the contrary
notwithstanding, in no event shall the amount of Guarantor’s liability hereunder
exceed the maximum amount that (after giving effect to the incurring of the
obligations hereunder and to any rights to contribution of Guarantor from other
affiliates of Borrower) would not render the rights to payment of Agent and the
Lenders hereunder void, voidable or avoidable under any applicable fraudulent
transfer law.

10. Stay of Acceleration. In the event that acceleration of the time for payment
of any of the Obligations is stayed, upon the insolvency, bankruptcy or
reorganization of Borrower or any other Person, or otherwise, all such amounts
shall nonetheless be payable by Guarantor immediately upon demand by Agent.

 

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11. Notice. All notices, requests, demands and other communications provided for
hereunder shall be in writing and, if to Guarantor, mailed or delivered to it,
addressed to it at the address specified on the signature page of this
Agreement, if to Agent or any Lender, mailed or delivered to it, addressed to
the address of Agent or such Lender specified on the signature pages of the
Credit Agreement, or, as to each party, at such other address as shall be
designated by such party in written notice to each of the other parties. All
notices, statements, requests, demands and other communications provided for
hereunder shall be deemed to be given or made when delivered or two Business
Days after being deposited in the mails with postage prepaid by registered or
certified mail, addressed as aforesaid, or sent by facsimile with telephonic
confirmation of receipt, except that notices from Guarantor to Agent or any
Lender pursuant to any of the provisions hereof shall not be effective until
received.

12. Successors and Assigns. This Agreement shall bind Guarantor and Guarantor’s
successors and assigns and shall inure to the benefit of Agent and each Lender
and their respective successors and assigns, including (without limitation) each
holder of any Note evidencing any of the Obligations.

13. Invalidity. If, at any time, one or more provisions of this Agreement is or
becomes invalid, illegal or unenforceable in whole or in part, the validity,
legality and enforceability of the remaining provisions shall not in any way be
affected or impaired thereby.

14. Entire Agreement. This Agreement constitutes a final written expression of
all of the terms of this Agreement, is a complete and exclusive statement of
those terms and supersedes all oral representations, negotiations and prior
writings, if any, with respect to the subject matter hereof.

15. Relationship of Parties; Setoffs. The relationship between (a) Guarantor and
(b) Agent and the Lenders with respect to this Agreement is and shall be solely
that of debtor and creditors, respectively, and Agent and the Lenders shall have
no fiduciary obligation toward Guarantor with respect to this Agreement or the
transactions contemplated hereby. If and to the extent any payment is not made
when due hereunder, Agent and each Lender may setoff and charge from time to
time any amount so due against any and all of Guarantor’s accounts or deposits
with Agent or such Lender.

16. Headings. The headings and subheadings used herein are for convenience of
reference only and shall be ignored in interpreting the provisions of this
Agreement.

17. Governing Law; Submission to Jurisdiction. The provisions of this Agreement
and the respective rights and duties of Guarantor, Agent and the Lenders
hereunder shall be governed by and construed in accordance with Ohio law,
without regard to principles of conflicts of laws which would result in the
application of the law of any other state. Guarantor hereby irrevocably submits
to the non-exclusive jurisdiction of any Ohio state or federal court sitting in
Cleveland, Ohio, over any action or proceeding arising out of or relating to
this Agreement, any Loan Document or any Related Writing, and Guarantor hereby
irrevocably agrees that all claims in respect of such action or proceeding may
be heard and determined in such Ohio state or federal court. Guarantor, on
behalf of itself and its Subsidiaries, hereby irrevocably waives, to

 

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the fullest extent permitted by law, any objection it may now or hereafter have
to the laying of venue in any such action or proceeding in any such court as
well as any right it may now or hereafter have to remove such action or
proceeding, once commenced, to another court on the grounds of FORUM NON
CONVENIENS or otherwise. Guarantor agrees that a final, nonappealable judgment
in any such action or proceeding in any state or federal court in the State of
Ohio shall be conclusive and may be enforced in other jurisdictions by suit on
the judgment or in any other manner provided by law.

[Remainder of page intentionally left blank.]

 

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JURY TRIAL WAIVER. GUARANTOR, TO THE EXTENT PERMITTED BY LAW, HEREBY WAIVES ANY
RIGHT TO HAVE A JURY PARTICIPATE IN RESOLVING ANY DISPUTE, WHETHER SOUNDING IN
CONTRACT, TORT, OR OTHERWISE, AMONG AGENT, THE LENDERS, BORROWER AND GUARANTOR,
OR ANY THEREOF, ARISING OUT OF, IN CONNECTION WITH, RELATED TO, OR INCIDENTAL TO
THE RELATIONSHIP ESTABLISHED AMONG THEM IN CONNECTION WITH THIS AGREEMENT OR ANY
NOTE OR OTHER AGREEMENT, INSTRUMENT OR DOCUMENT EXECUTED OR DELIVERED IN
CONNECTION THEREWITH OR THE TRANSACTIONS RELATED THERETO.

IN WITNESS WHEREOF, the undersigned has executed and delivered this Guaranty of
Payment as of the date first set forth above.

 

Address:   23 Old Kings Highway South   WORKBOOK, INC.  

Darien, Connecticut 06820

Attention: President or General Counsel

  By:  

/s/ Christopher S. Cardell

      Christopher S. Cardell       President, Chief Operating Officer and
Secretary

 

Signature Page to

Guaranty of Payment