Document:

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                                                                     Exhibit 4.2

                             COOLSAVINGS.COM INC.

                         REGISTRATION RIGHTS AGREEMENT

          REGISTRATION RIGHTS AGREEMENT, dated as of July 30, 2001 (this
"Agreement"), among Landmark Ventures VII, LLC and any affiliates or transferee
 ---------
thereof ("Landmark"), the investors listed on Schedule I hereto (the "Current
          --------                                                    -------
Investors", and, together with Landmark, the "Investors") and coolsavings.com
---------                                     ---------
inc., a Michigan corporation (the "Company").
                                   -------

                                R E C I T A L S
                                - - - - - - - -

          WHEREAS, the Current Investors own shares of Series C Convertible
Preferred Stock, with no par value per share, of the Company (the "Series C
                                                                   --------
Preferred Stock"), and/or shares of Common Stock, with no par value per share,
---------------
of the Company (the "Common Stock"); and
                     ------------

          WHEREAS, Landmark has, pursuant to the terms of the Securities
Purchase Agreement, dated as of July 30, 2001, between Landmark and the Company
(the "Purchase Agreement"), agreed to purchase shares of Series B Convertible
      ------------------
Preferred Stock, with no par value per share, of the Company (the "Series B
                                                                   --------
Preferred Stock" and, together with the Series C Preferred Stock, the "Preferred
---------------                                                        ---------
Stock"), warrants to purchase Common Stock (the "Warrants") and a Senior Secured
-----                                            --------
Note of the Company (the "Note"); and
                          ----

          WHEREAS, the shares of Preferred Stock and the Warrants purchased by
Landmark are convertible into shares of Common Stock; and

          WHEREAS, the Current Investors have previously been granted certain
registration rights under that certain Shareholders Agreement, dated June 1,
1998 between the Company and the Holders as defined and listed therein (the
Current Investors that are parties to such Shareholders Agreement are
hereinafter collectively referred to as the "1998 Holders", and are listed on
                                             ------------
Schedule II hereto), and the Registration Rights Agreement, dated as of March 1,
2001 by and among the Company and the purchasers of its 8% senior subordinated
convertible promissory notes (the Current Investors that are parties to such
Registration Rights Agreement are hereinafter collectively referred to as the
"2001 Holders", and are listed on Schedule III hereto), and
 ------------

          WHEREAS, the Company has agreed, as a condition precedent to
Landmark's obligations under the Purchase Agreement, to grant the Investors
certain registration rights; and

          WHEREAS, the Company and the Investors desire to define the
registration rights of the Investors on the terms and subject to the conditions
herein set forth.
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          NOW, THEREFORE, in consideration of the foregoing premises and for
other good and valuable consideration, the parties hereby agree as follows:

          SECTION 1. DEFINITIONS

          As used in this Agreement, the following terms have the respective
meaning set forth below.  Capitalized terms used but not defined herein shall
have the meaning set forth in the Purchase Agreement.

          Exchange Act: shall mean the Securities Exchange Act of 1934, as
          ------------
amended;

          Holder: shall mean any holder of Registrable Securities;
          ------

          Initiating Holder:  shall mean Landmark and any of its successors or
          -----------------
assigns who in the aggregate are Holders of more than 15% of the then
outstanding Registrable Securities and the 2001 Holders subject to the
restrictions set forth in Section 2(a)(3).

          Person:  shall mean an individual, partnership, joint-stock company,
          ------
corporation, trust or unincorporated organization, and a government or agency or
political subdivision thereof;

          Register, Registered and Registration: shall mean a registration
          --------  ----------     ------------
effected by preparing and filing a registration statement in compliance with the
Securities Act (and any post-effective amendments filed or required to be filed)
and the declaration or ordering of effectiveness of such registration statement;

          Registrable Securities: shall mean (A) shares of Common Stock
          ----------------------
issuable upon conversion of the Preferred Stock or exercise of the Warrants, (B)
any additional shares of Common Stock acquired or held as of the date hereof by
the Investors, (C) with respect to Landmark, any additional shares of Common
Stock acquired after the date hereof, and (D) any stock of the Company issued as
a dividend or other distribution with respect to, or in exchange for or in
replacement of, the shares of Preferred Stock, the Warrants or Common Stock
referred to in clause (A) or (B). As to any particular Registrable Securities,
such securities will cease to be Registrable Securities on the earliest of the
following dates: (a) the date such securities have been sold to the public
pursuant to an offering registered under the Securities Act, or (b) the date
such securities have been sold to the public in a transaction exempt from the
registration and prospectus delivery requirements of the Securities Act;

          Registration Expenses: shall mean all expenses incurred by the
          ---------------------
Company in compliance with Section 2(a), (b) and (c) hereof, including, without
limitation, all registration and filing fees, printing expenses, fees and
disbursements of counsel for the Company, fees and expenses of one counsel for
all the Holders in an amount not to exceed $25,000 (provided that if such fees
and expenses of the Holders' counsel are incurred by the Company in connection
with a registration pursuant to Section 2(b) or 2(c), such fees and expenses
shall not exceed $15,000), blue sky fees and expenses and the expense of any
special audits incident to or required by any such registration (but excluding
the compensation of regular employees of the Company, which shall be paid in any
event by the Company);

                                      -2-
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          SEC: shall mean the Securities and Exchange Commission, or any
          ---
successor commission or agency having similar powers;

          Security, Securities: shall have the meaning set forth in Section
          --------------------
2(1) of the Securities Act;

          Securities Act: shall mean the Securities Act of 1933, as amended, and
          --------------
the rules and regulations promulgated thereunder; and

          Selling Expenses: shall mean all underwriting discounts and selling
          ----------------
commissions applicable to the sale of Registrable Securities, all transfer taxes
relating to the sale or disposition of the Registrable Securities and all fees
and disbursements of counsel for each of the Holders other than fees and
expenses of one counsel for all the Holders in an amount not to exceed $25,000
(provided that if such fees and expenses of the Holders' counsel are incurred by
the Company in connection with a registration pursuant to Section 2(b) or 2(c),
such fees and expenses shall not exceed $15,000).

          SECTION 2.    REGISTRATION RIGHTS

     (a)  Requested Registration.
          ----------------------

          (i)  Request for Registration.  If the Company shall receive from an
               ------------------------
     Initiating Holder, at any time, a written request that the Company effect
     any registration with respect to all or a part of the Registrable
     Securities, the Company will:

               (1)  promptly give written notice of the proposed registration,
          qualification or compliance to all other Holders; and

               (2)  as soon as practicable, use its diligent best efforts to
          effect such registration (including, without limitation, the execution
          of an undertaking to file post-effective amendments, appropriate
          qualification under applicable blue sky or other state securities laws
          and appropriate compliance with applicable regulations issued under
          the Securities Act) as may be so requested and as would permit or
          facilitate the sale and distribution of all or such portion of such
          Registrable Securities as are specified in such request, together with
          all or such portion of the Registrable Securities of any Holder or
          Holders joining in such request as are specified in a written request
          received by the Company within 10 business days after written notice
          from the Company is given under Section 2(a)(i)(1) above except as set
          forth in Section 2(a)(ii) below; provided that the Company shall not
                                           --------
          be obligated to effect, or take any action to effect, any such
          registration pursuant to this Section 2(a):

                    (A)  In any particular jurisdiction (x) in which the Company
               would be required to execute a general consent to service of
               process in effecting such registration, qualification or
               compliance, unless the Company is already subject to service in
               such jurisdiction and except as

                                      -3-
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               may be required by the Securities Act or applicable rules or
               regulations thereunder, or (y) where expressions of investment
               interest are not sufficient in such jurisdiction to reasonably
               justify the registration or qualification in such jurisdiction;

                    (B)  After the Company has effected five (5) such
               registrations pursuant to this Section 2(a) and such
               registrations have been declared or ordered effective and the
               sales of such Registrable Securities shall have closed;

                    (C)  If the Registrable Securities requested by all Holders
               to be registered pursuant to such request have an anticipated
               aggregate public offering price (before any underwriting
               discounts and commissions) of less than $5,000,000;

                    (D)  If the Company shall furnish to the Initiating Holder a
               certificate signed by the President of the Company stating that
               in the good faith judgment of the Board of Directors it would be
               seriously detrimental to the Company or its stockholders for a
               registration statement to be filed in the near future, in which
               case the Company's obligation to use its best efforts to comply
               with this Section 2 shall be deferred for a period not to exceed
               ninety (90) days from the date of receipt of written request from
               the Initiating Holder; provided, however, that the Company shall
                                      --------  -------
               not exercise such right more than once in any 360 day period.

               (3)  Notwithstanding anything to the contrary set forth herein,
     Landmark may initiate a total of three (3) requested registrations as an
     Initiating Holder and the 2001 Holders may initiate a total of one (1)
     requested registration under this Section 2(a). The 2001 Holders may only
     initiate such requested registration as an Initiating Holder under the
     following conditions:

                    (A)  The 2001 Holders (or their permitted transferees) shall
     have requested such registration prior to March 1, 2005;

                    (B)  Such request constitutes a request by the holder or
     holders of at least 75% of Registrable Securities held by the 2001 Holders
     (or their permitted transferees); and

                    (C)  Landmark shall have consented in writing to such
     requested registration by the 2001 Holders (or their permitted
     transferees); provided, however, that such written consent from Landmark
                   --------  -------
     shall not be required if either (a) Landmark does not own any Registrable
     Securities and the Company has no outstanding indebtedness of any kind to
     Landmark, or (b) each of the conditions under Section 2(l) have been
     satisfied.

                                      -4-
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          If any of the other Holders request such inclusion, the registration
     statement filed pursuant to the request of the Initiating Holder may,
     subject to the provisions of Section 2(a)(ii) below, include Registrable
     Securities held by such Holders.  In the event any Initiating Holder
     requests a registration pursuant to this Section 2(a) in connection with a
     distribution of Registrable Securities to its affiliates, the registration
     shall provide for the resale by such affiliates, if requested by such
     Initiating Holder.

          (ii) Underwriting.
               ------------

               (1)  If the Initiating Holder intends to distribute the
          Registrable Securities covered by its request by means of an
          underwriting, it shall so advise the Company as a part of its request
          made pursuant to Section 2(a).

               (2)  If any of the other Holders request such inclusion, the
          Initiating Holder shall offer to include the securities of such
          Holders in the underwriting and may condition such offer on their
          acceptance of the further applicable provisions of this Section 2. The
          Holders whose shares are to be included in such registration and the
          Company shall enter into an underwriting agreement (together with such
          other documents as may be required by such underwriting agreement) in
          customary form with the representative of the underwriter or
          underwriters selected for such underwriting by Landmark and reasonably
          acceptable to the Company.

               (3)  Notwithstanding any other provision of this Section 2(a), if
          the representative of the underwriter(s) advises the Holders in
          writing that marketing factors require a limitation on the number of
          shares to be underwritten, the Company shall include in such
          registration (A) first, all of the Registrable Securities requested to
          be included therein by the Initiating Holder, (B) second, the
          Registrable Securities requested to be included therein by Landmark
          (or its successors or assigns), and (C) third, the Registrable
          Securities requested to be included therein by Holders (including the
          2001 Holders) other than Landmark, pro rata among such Holders (based
          on the number of shares held by each such Holder) by such minimum
          number of shares as is necessary to comply with such request. If a
          limitation on the number of shares is still required (even after all
          other Holders have been reduced down to zero), then and only then
          shall the securities held by Landmark be reduced on a pro rata basis
          (based on the number of shares held by Landmark) by such minimum
          number of shares as is necessary to comply with such request. No
          Registrable Securities or any other securities excluded from the
          underwriting by reason of the underwriter's marketing limitation shall
          be included in such registration.

               (4)  If any Holder who has requested inclusion in such
          registration as provided above disapproves of the terms of the
          underwriting, such person may elect to withdraw therefrom by written
          notice to the Company, the underwriter and the Initiating Holder. The
          securities so withdrawn shall also be withdrawn from registration.

                                      -5-
<PAGE>

               (5)  If the underwriter has not limited the number of Registrable
          Securities or other securities to be underwritten, the Company and
          officers and directors of the Company may include its or their
          securities for its or their own account in such registration if the
          representative of the underwriter(s) so agrees and if the number of
          Registrable Securities and other securities which would otherwise have
          been included in such registration and underwriting will not thereby
          be limited.

     (b)  Company Registration.
          --------------------

          (i)  If the Company shall determine to register any of its equity
     securities for its own account, other than a registration relating solely
     to employee benefit plans, or a registration relating solely to an SEC Rule
     145 transaction, or a registration on any registration form which does not
     permit secondary sales or does not include substantially the same
     information as would be required to be included in a registration statement
     covering the sale of Registrable Securities, then the Company will in
     connection with each such registration:

               (1)  promptly give to each of the Holders a written notice
          thereof (which shall include a list of the jurisdictions in which the
          Company intends to attempt to qualify such securities under the
          applicable blue sky or other state securities laws); and

               (2)  include in such registration (and any related qualification
          under blue sky laws or other compliance), and in any underwriting
          involved therein, all the Registrable Securities specified in a
          written request or requests, made by the Holders within fifteen (15)
          days after receipt of the written notice from the Company described in
          clause (1) above, except as set forth in Section 2(b)(ii) below. Such
          written request may specify all or a part of the Holders' Registrable
          Securities. In the event any Holder requests inclusion in a
          registration pursuant to this Section 2(b) in connection with a
          distribution of Registrable Securities to its affiliates, the
          registration shall provide for the resale by such affiliates, if
          requested by such Holder.

          (ii) Underwriting.
               ------------

               (1)  If the registration of which the Company gives notice is for
          a registered public offering involving an underwriting, the Company
          shall so advise each of the Holders as a part of the written notice
          given pursuant to Section 2(b)(i)(1).

               (2)  If any of the Holders request such inclusion, the Company
          shall offer to include the securities of such Holders in the
          underwriting and may condition such offer on their acceptance of the
          further applicable provisions of this Section 2. The Holders whose
          shares are to be included in such registration shall (together with
          the Company) enter into an underwriting agreement (together

                                      -6-
<PAGE>

          with such other documents as may be required by such underwriting
          agreement) in customary form with the representative of the
          underwriter or underwriters selected for underwriting by the Company
          and reasonably acceptable to the Holders.

                (3)  Notwithstanding any other provision of this Section 2(b),
          if the representative of the underwriter(s) determines that marketing
          factors require a limitation on the number of shares to be
          underwritten, the representative may (subject to the allocation
          priority set forth below) limit the number of Registrable Securities
          to be included in the registration and underwriting. The Company shall
          so advise all Holders requesting registration, and the number of
          shares of securities that are entitled to be included in the
          registration and underwriting shall be allocated in the following
          manner: (i) first, the Company shall include in such registration the
          securities that the Company proposes to sell, (ii) second, the Company
          shall include in such registration the Registrable Securities
          requested to be included therein by Landmark (or its successors or
          assigns), (iii) third, the Company shall include in such registration
          the Registrable Securities requested to be included therein by Holders
          (including the 2001 Holders) other than Landmark, pro rata among such
          Holders (based on the number of shares held by each such Holder), and
          (iv) fourth, the Company shall include in such registration the
          securities of the Company held by officers and directors of the
          Company (other than Registrable Securities) requested to be included
          therein by such officers and directors.

                (4)  If any of the Holders or any officer or director
          disapproves of the terms of any such underwriting, he may elect to
          withdraw therefrom by written notice to the Company and the
          underwriter. Any Registrable Securities or other securities excluded
          or withdrawn from such underwriting shall be withdrawn from such
          registration.

          (iii) Notwithstanding the foregoing, the rights of the 1998 Holders
     and the 2001 Holders shall be limited in the following manner.

                (1)  All rights of the 1998 Holders under this Agreement shall
          terminate on May 19, 2005.

                (3)  All rights of the 2001 Holders under this Agreement shall
          terminate on March 1, 2005.

     (c)  Form S-3.
          --------

          (i)   The Company shall use its best efforts to qualify for
     registration on Form S-3 for secondary sales. After the Company has
     qualified for the use of Form S-3, each of Landmark, the 1998 Holders and
     the 2001 Holders shall have the right to request registrations on Form S-3
     (such requests shall be in writing and shall state the number of shares of
     Registrable Securities to be disposed of and the intended method of
     disposition

                                      -7-
<PAGE>

     of shares by such holders); provided that the Company shall not be
                                 --------
     obligated to effect, or take any action to effect, any such registration
     pursuant to this Section 2(c):

                 (1)  Unless Landmark, the 1998 Holders or the 2001 Holders
           requesting registration proposes to dispose of shares of Registrable
           Securities having an aggregate price to the public (before deduction
           of underwriting discounts and expenses of sale) of more than
           $2,000,000;

                 (2)  Within 180 days of the effective date of the most recent
           registration pursuant to this Section 2(c) in which securities held
           by Landmark, the 1998 Holders or the 2001 Holders could have been
           included for sale or distribution;

                 (3)  In any particular jurisdiction (x) in which the Company
           would be required to execute a general consent to service of process
           in effecting such registration, qualification or compliance, unless
           the Company is already subject to service in such jurisdiction and
           except as may be required by the Securities Act or applicable rules
           or regulations thereunder, or (y) where expressions of investment
           interest are not sufficient in such jurisdiction to reasonably
           justify the registration or qualification in such jurisdiction;

                 (4)  If the Company shall furnish to Landmark, the 1998 Holders
           or the 2001 Holders, as applicable, a certificate signed by the
           President of the Company stating that in the good faith judgment of
           the Board of Directors it would be seriously detrimental to the
           Company or its stockholders for a registration statement to be filed
           in the near future, in which case the Company's obligation to use its
           best efforts to comply with this Section 2(c) shall be deferred for a
           period not to exceed ninety (90) days from the date of receipt of
           written request from Landmark, the 1998 Holders or the 2001 Holders;
           provided, however, that the Company shall not exercise such right
           --------  -------
           more than once in any 360 day-period.

           (ii)  The Company shall give written notice to all Holders of the
     receipt of a request for registration pursuant to this Section 2(c) and
     shall provide a reasonable opportunity for other Holders to participate in
     the registration, provided that if the registration is for an underwritten
                       --------
     offering, the terms of Section 2(a)(ii) shall apply to all participants in
     such offering.  Subject to the foregoing, the Company will use its best
     efforts to effect promptly the registration of all shares of Registrable
     Securities on Form S-3 to the extent requested by Landmark, the 1998
     Holders or the 2001 Holders thereof for purposes of disposition.  In the
     event Landmark, the 1998 Holders or the 2001 Holders requests a
     registration pursuant to this Section 2(c) in connection with a
     distribution of Registrable Securities to its affiliates, the registration
     shall provide for the resale by such affiliates, if requested by Landmark,
     the 1998 Holders or the 2001 Holders, as applicable.

           (iii) Notwithstanding anything to the contrary set forth herein,
     Landmark shall have the right to request an unlimited number of Form S-3
     registrations, the 1998 Holders shall collectively only have the right to
     request two (2) Form S-3 registrations under this

                                      -8-
<PAGE>

     section 2(c) and the 2001 Holders shall collectively only have the right to
     request three (3) Form S-3 registrations under this Section 2(c). The 1998
     Holders and the 2001 Holders may only initiate such requested registration
     if Landmark shall have consented in writing to such requested registration
     prior to the Company granting such request for registration; provided,
                                                                  --------
     however, that such written consent from Landmark shall not be required if
     -------
     either (A) Landmark does not own any Registrable Securities and the Company
     has no outstanding indebtedness of any kind to Landmark, or (B) each of the
     conditions under Section 2(l) have been satisfied.

     (d)  Expenses of Registration.  All Registration Expenses incurred in
          ------------------------
connection with any registration, qualification or compliance pursuant to this
Section 2 shall be borne by the Company, and all Selling Expenses shall be borne
by the holders of the securities so registered pro rata on the basis of the
number of their shares so registered.

     (e)  Registration Procedures.  In the case of each registration effected
          -----------------------
by the Company pursuant to this Section 2, the Company will keep the Holders, as
applicable, advised in writing as to the initiation of each registration and as
to the completion thereof. At its expense, the Company will:

          (i)    keep such registration effective for a period of one hundred
     twenty (120) days or until the Holders (or in the case of a distribution to
     the affiliates of such Holder, such affiliates), as applicable, have
     completed the distribution described in the registration statement relating
     thereto, whichever first occurs; provided, however, that in the case of any
                                      --------  -------
     registration of Registrable Securities on Form S-3 which are intended to be
     offered on a continuous or delayed basis, such 120-day period shall be
     extended until all such Registrable Securities are sold, provided that Rule
                                                              --------
     415, or any successor rule under the Securities Act, permits an offering on
     a continuous or delayed basis, and provided further that applicable rules
                                        ----------------
     under the Securities Act governing the obligation to file a post-effective
     amendment permit, in lieu of filing a post-effective amendment which (y)
     includes any prospectus required by Section 10(a) of the Securities Act or
     (z) reflects facts or events representing a material or fundamental change
     in the information set forth in the registration statement, the
     incorporation by reference of information required to be included in (y)
     and (z) above to be contained in periodic reports filed pursuant to Section
     12 or 15(d) of the Exchange Act in the registration statement;

          (ii)   furnish such number of prospectuses and other documents
     incident thereto as each of the Holders, as applicable, from time to time
     may reasonably request;

          (iii)  notify each Holder of Registrable Securities covered by such
     registration at any time when a prospectus relating thereto is required to
     be delivered under the Securities Act of the happening of any event as a
     result of which the prospectus included in such registration statement, as
     then in effect, includes an untrue statement of a material fact or omits to
     state a material fact required to be stated therein or necessary to make
     the statements therein not misleading in the light of the circumstances
     then existing; and

          (iv)   furnish, on the date that such Registrable Securities are
     delivered to the underwriters for sale, if such securities are being sold
     through underwriters (1) an

                                      -9-
<PAGE>

     opinion, dated as of such date, of the counsel representing the Company for
     the purposes of such registration, in form and substance as is customarily
     given to underwriters in an underwritten public offering and reasonably
     satisfactory to a majority in interest of the Holders participating in such
     registration, addressed to the underwriters and (2) a letter, dated as of
     such date, from the independent certified public accountants of the
     Company, in form and substance as is customarily given by independent
     certified public accountants to underwriters in an underwritten public
     offering and reasonably satisfactory to a majority in interest of the
     Holders participating in such registration, addressed to the underwriters.

          Each Holder agrees that, upon receipt of any notice from the Company
     of the happening of any event of the kind described in subsection (iii)
     above, such Holder shall forthwith discontinue disposition of shares of
     Common Stock pursuant to a Registration until receipt of an appropriate
     supplement or amendment to the prospectus of such Registration.

     (f)  Indemnification.
          ---------------

          (i)  The Company will indemnify each of the Holders, as applicable,
     each of its officers, directors and partners, and each person controlling
     each of the Holders, with respect to each registration which has been
     effected pursuant to this Section 2, and each underwriter, if any, and each
     person who controls any underwriter, against all claims, losses, damages
     and liabilities (or actions in respect thereof) arising out of or based on
     any untrue statement (or alleged untrue statement) of a material fact
     contained in any prospectus, offering circular or other document (including
     any related registration statement, notification or the like) incident to
     any such registration, qualification or compliance, or based on any
     omission (or alleged omission) to state therein a material fact required to
     be stated therein or necessary to make the statements therein not
     misleading, or any violation by the Company of the Securities Act or the
     Exchange Act or any rule or regulation thereunder applicable to the Company
     and relating to action or inaction required of the Company in connection
     with any such registration, qualification or compliance, and will reimburse
     each of the Holders, each of its officers, directors and partners, and each
     person controlling each of the Holders, each such underwriter and each
     person who controls any such underwriter, for any legal and any other
     expenses reasonably incurred in connection with investigating and defending
     any such claim, loss, damage, liability or action; provided, however, that
                                                        --------  -------
     the Company will not be liable in any such case to the extent that any such
     claim, loss, damage, liability or expense arises out of or is based on (1)
     any untrue statement or omission based upon written information furnished
     to the Company by the Holders or underwriter and stated to be specifically
     for use therein, or (2) a Holder's, or underwriter's, failure to deliver a
     copy of the registration statement or prospectus or any amendments or
     supplements thereto after the Company has furnished such Holder with a
     sufficient number of copies of the same.

          (ii) Each of the Holders will, if Registrable Securities held by it
     are included in the securities as to which such registration, qualification
     or compliance is being effected, severally and not jointly indemnify the
     Company, each of its directors and officers and each underwriter, if any,
     of the Company's securities covered by such a

                                      -10-
<PAGE>

     registration statement, each person who controls the Company or such
     underwriter, each other Holder and each of their officers, directors and
     partners, and each person controlling such other Holder against all claims,
     losses, damages and liabilities (or actions in respect thereof) arising out
     of or based on any untrue statement (or alleged untrue statement) of a
     material fact contained in any such registration statement, prospectus,
     offering circular or other document made by such Holder, or any omission
     (or alleged omission) to state therein a material fact required to be
     stated therein or necessary to make the statements by such Holder therein
     not misleading, and will reimburse the Company and such other Holders,
     directors, officers, partners, persons, underwriters or control persons for
     any legal or any other expenses reasonably incurred in connection with
     investigating or defending any such claim, loss, damage, liability or
     action, in each case to the extent, but only to the extent, that such
     untrue statement (or alleged untrue statement) or omission (or alleged
     omission) is made in such registration statement, prospectus, offering
     circular or other document in reliance upon and in conformity with written
     information furnished to the Company by such Holder and stated to be
     specifically for use therein and then only to the extent that any loss,
     damages or other liability of any kind result from such alleged untrue
     statement; provided, however, that the obligations of each of the Holders
                --------  -------
     hereunder shall be limited to an amount equal to the net proceeds to such
     Holder of securities sold as contemplated herein.

          (iii)  Each party entitled to indemnification under this Section 2(f)
     (the "Indemnified Party") shall give notice to the party required to
           -----------------
     provide indemnification (the "Indemnifying Party") promptly after such
                                   ------------------
     Indemnified Party has actual knowledge of any claim as to which indemnity
     may be sought, and shall permit the Indemnifying Party to assume the
     defense of any such claim or any litigation resulting therefrom; provided
                                                                      --------
     that counsel for the Indemnifying Party, who shall conduct the defense of
     such claim or any litigation resulting therefrom, shall be approved by the
     Indemnified Party (whose approval shall not unreasonably be withheld) and
     the Indemnified Party may participate in such defense at such party's
     expense (unless the Indemnified Party shall have reasonably concluded that
     there may be a conflict of interest between the Indemnifying Party and the
     Indemnified Party in such action, in which case the reasonable fees and
     expenses of one counsel shall be at the expense of the Indemnifying Party),
     and provided further that the failure of any Indemnified Party to give
         -------- -------
     notice as provided herein shall not relieve the Indemnifying Party of its
     obligations under this Section 2 unless the Indemnifying Party is
     materially prejudiced thereby. No Indemnifying Party, in the defense of any
     such claim or litigation shall, except with the consent of each Indemnified
     Party (whose consent shall not be unreasonably withheld), consent to entry
     of any judgment or enter into any settlement which does not include as an
     unconditional term thereof the giving by the claimant or plaintiff to such
     Indemnified Party of a release from all liability in respect to such claim
     or litigation. Each Indemnified Party shall furnish such information
     regarding itself or the claim in question as an Indemnifying Party may
     reasonably request in writing and as shall be reasonably required in
     connection with the defense of such claim and litigation resulting
     therefrom.

          (iv)   If the indemnification provided for in this Section 2(f) is
     held by a court of competent jurisdiction to be unavailable to an
     Indemnified Party with respect to any loss,

                                      -11-
<PAGE>

     liability, claim, damage or expense referred to herein, then the
     Indemnifying Party, in lieu of indemnifying such Indemnified Party
     hereunder, shall contribute to the amount paid or payable by such
     Indemnified Party as a result of such loss, liability, claim, damage or
     expense (solely to the extent such amount is required pursuant to Section
     2(f)) in such proportion as is appropriate to reflect the relative fault of
     the Indemnifying Party on the one hand and of the Indemnified Party on the
     other in connection with the statements or omissions which resulted in such
     loss, liability, claim, damage or expense, as well as any other relevant
     equitable considerations including without limitation the relative fault of
     other Indemnifying Parties. The relative fault of the Indemnifying Party
     and of the Indemnified Party shall be determined by reference to, among
     other things, whether the untrue (or alleged untrue) statement of a
     material fact or the omission (or alleged omission) to state a material
     fact relates to information supplied by the Indemnifying Party or by the
     Indemnified Party and the parties' relative intent, knowledge, access to
     information and opportunity to correct or prevent such statement or
     omission. The foregoing notwithstanding, no Indemnifying Party will be
     required to contribute any amount in excess of the public offering price of
     all Registrable Securities offered by it pursuant to the registration
     statement, and no person or entity guilty of fraudulent misrepresentation
     (within the meaning of Section 11(f) of the Securities Act) will be
     entitled to contribution from any person or entity who was not guilty of
     such fraudulent misrepresentation.

          (v)   Notwithstanding the foregoing, to the extent that the provisions
     on indemnification and contribution contained in the underwriting agreement
     entered into in connection with any underwritten public offering
     contemplated by this Agreement are in conflict with the foregoing
     provisions, the provisions in such underwriting agreement shall be
     controlling.

          (vi)  The foregoing indemnity agreement of the Company and Holders is
     subject to the condition that, insofar as they relate to any loss, claim,
     liability or damage arising out of a statement made in or omitted from a
     preliminary prospectus but eliminated or remedied in the amended prospectus
     on file with the Commission at the time the registration statement in
     question becomes effective or the amended prospectus filed with the
     Commission pursuant to Commission Rule 424(b) (the "Final Prospectus"),
                                                         ----------------
     such indemnity or contribution agreement shall not inure to the benefit of
     any underwriter or Holder if a copy of the Final Prospectus was furnished
     to the underwriter and was not furnished to the person asserting the loss,
     liability, claim or damage at or prior to the time such action is required
     by the Securities Act.

     (g)  Information by the Holders.
          --------------------------

          (i)   Each of the Holders holding securities included in any
     registration shall furnish to the Company such information regarding such
     Holder and the distribution proposed by such Holder as the Company may
     reasonably request in writing and as shall be reasonably required in
     connection with any registration, qualification or compliance referred to
     in this Section 2.

                                      -12-
<PAGE>

          (ii)   In the event that, either immediately prior to or subsequent to
     the effectiveness of any registration statement, any Holder shall
     distribute Registrable Securities to its affiliates, such Holder shall so
     advise the Company and provide such information as shall be necessary to
     permit an amendment to such registration statement to provide information
     with respect to such affiliates, as selling securityholders. Promptly
     following receipt of such information, the Company shall file an
     appropriate amendment to such registration statement reflecting the
     information so provided. Any incremental expense to the Company resulting
     from such amendment shall be borne by such Holder.

     (h)  Rule 144 Reporting.
          ------------------

          With a view to making available the benefits of certain rules and
regulations of the SEC which may permit the sale of restricted securities to the
public without registration, the Company agrees to:

          (i)    make and keep public information available as those terms are
     understood and defined in Rule 144 under the Securities Act ("Rule 144");
                                                                   --------

          (ii)   use its best efforts to file with the SEC in a timely manner
     all reports and other documents required of the Company under the
     Securities Act and the Exchange Act; and

          (iii)  so long as the Holder owns any Registrable Securities, furnish
     to the Holder upon request a written statement by the Company as to its
     compliance with the reporting requirements of Rule 144 and of the
     Securities Act and the Exchange Act, a copy of the most recent annual or
     quarterly report of the Company, and such other reports and documents so
     filed as the Holder may reasonably request in availing itself of any rule
     or regulation of the SEC allowing the Holder to sell any such securities
     without registration.

     (i)  Assignment.  The registration rights set forth in this Section 2 may
          ----------
be assigned, in whole or in part, to any transferee of Registrable Securities
(who shall be bound by all obligations of this Agreement).

     (j)  Additional Agreements.  Without the written consent of Landmark and
          ---------------------
the holders of a majority of the Registrable Securities held by the Current
Investors, the Company shall not enter into any additional registration rights
agreements.

     (k)  Termination of Prior Agreements.  The 2001 Holders and the Company
          -------------------------------
hereby terminate that certain Registration Rights Agreement, dated as of March
1, 2001, which is hereby declared null and void and of no further force or
effect. The Current Investors hereby irrevocably waive all of their rights under
that certain: (1) Shareholders Agreement, dated June 1, 1998, by and among the
Company and certain of its stockholders; (2) Registration Rights Agreement,
dated May 28, 1999, by and among the Company and the purchasers of its 1999
Unsecured Convertible Subordinated Promissory Notes; and (3) Registration Rights
Agreement, dated

                                      -13-
<PAGE>

December 21, 1999, by and among the Company and its Series A Preferred
stockholders.

     (l)  Requested Registrations Not Subject to Landmark Consent.  The rights
          -------------------------------------------------------
of the 2001 Holders to request registrations pursuant to Sections 2(a) and 2(c)
and the rights of the 1998 Holders to request registrations pursuant Section
2(c) shall not be subject to the written consent of Landmark if such request for
registration (a "Section 2(l) Request") is made after December 31, 2003, and as
                 --------------------
of the date of the Section 2(l) Request the following conditions have been
satisfied:

          (i)    no event of default has occurred and is continuing under that
     certain Amended and Restated Loan and Security Agreement, dated as of
     July 30, 2001, by and between the Company and Landmark Communications,
     Inc. (the "Loan Agreement");
                ---------------

          (ii)   the Company has paid all accrued dividends on the Company's
     Series B Preferred Stock and issued all PIK Warrants (as defined in the
     Loan Agreement) required under the Loan Agreement;

          (iii)  for each of the past four (4) fiscal quarters immediately
     preceding such Section 2(l) Request, the Company has had positive net
     earnings of at least $500,000 and positive earnings before interest, taxes,
     depreciation and amortization ("EBITDA") of at least $1,000,000, and each
                                     ------
     such determination of net earnings and EBITDA has been calculated according
     to generally accepted accounting principles;

          (iv)   the Company has positive Working Capital (as that term is
     defined in the Loan Agreement) of at least $3,000,000;

          (v)    the applicable 1998 or 2001 Holder making a Section 2(l)
     Request provides the Company with a written letter addressed to the Company
     by a nationally recognized investment banking firm which confirms that, as
     of the date of such request for registration, the current market conditions
     and financial condition of the Company are satisfactory for granting such
     Section 2(l) Request taking into account solely the number of shares to be
     issued thereunder;

          (vi)   the Company is listed on a nationally recognized stock exchange
     or is quoted on the automated quotation system of a national securities
     association; and

          (vii)  the Company has not granted a Section 2(l) Request from a 2001
     Holder or 1998 Holder without the written consent of Landmark in the twelve
     (12) months immediately preceding such Section 2(l) Request.

          SECTION 3.  MISCELLANEOUS

                                      -14-
<PAGE>

     (a)  Directly or Indirectly.  Where any provision in this Agreement refers
          ----------------------
to action to be taken by any Person, or which such Person is prohibited from
taking, such provision shall be applicable whether such action is taken directly
or indirectly by such Person.

     (b)  Governing Law.  This Agreement shall be governed by and construed in
          -------------
accordance with the laws of the State of New York applicable to contracts made
and to be performed entirely within such State.

     (c)  Section Headings.  The headings of the sections and subsections of
          ----------------
this Agreement are inserted for convenience only and shall not be deemed to
constitute a part thereof.

     (d)  Notices.
          -------

          (i)    All communications under this Agreement shall be in writing and
     shall be delivered by hand or facsimile or mailed by overnight courier or
     by registered or certified mail, postage prepaid:

                 (1)  if to the Company, to 360 N. Michigan Avenue, Chicago,
          Illinois 60601, Attention: CEO (facsimile: (312) 853-0456), or at such
          other address as it may have furnished in writing to the Holders, with
          a copy to Jaffe, Raitt, Heuer & Weiss, One Woodward Avenue, Suite
          2400, Detroit, Michigan 48226 (facsimile: (313) 961-8358), Attention:
          Peter Sugar.

                 (2)  if to Landmark, at Landmark Communications, Inc., 150 W.
          Brambleton Avenue Norfolk, VA 23510, Facsimile: (757) 664-2164,
          Attention: Guy R. Friddell III, Executive Vice President and General
          Counsel, or at such other address or facsimile number as may have been
          furnished the Company in writing, with copies to Willcox and Savage,
          1800 Bank of America Center, One Commercial Place, Norfolk, Virginia
          23510-2197 (facsimile (757 628-5566), Attention Thomas Inglima, Esq.
          and Willkie Farr & Gallagher, 787 Seventh Avenue, New York, NY 10019
          (facsimile: (212) 728-8111), Attention: William J. Grant, Jr.

                 (3)  if to the Current Investors, at the address or facsimile
          number listed on Schedule II hereto, or at such other address or
          facsimile number as may have been furnished the Company in writing.

          (ii)   Any notice so addressed shall be deemed to be given: if
     delivered by hand or facsimile, on the date of such delivery; if mailed by
     courier, on the first business day following the date of such mailing; and
     if mailed by registered or certified mail, on the third business day after
     the date of such mailing.

     (e)  Reproduction of Documents.  This Agreement and all documents relating
          -------------------------
thereto, including, without limitation, any consents, waivers and modifications
which may hereafter be executed may be reproduced by the parties by any
photographic, photostatic, microfilm, microcard, miniature photographic or other
similar process and the parties may destroy any

                                      -15-
<PAGE>

     original document so reproduced.  The parties hereto agree and stipulate
     that any such reproduction shall be admissible in evidence as the original
     itself in any judicial or administrative proceeding (whether or not the
     original is in existence and whether or not such reproduction was made by
     the parties in the regular course of business) and that any enlargement,
     facsimile or further reproduction of such reproduction shall likewise be
     admissible in evidence.

          (f)  Successors and Assigns. This Agreement shall inure to the benefit
               ----------------------
     of and be binding upon the successors and assigns of each of the parties.

          (g)  Entire Agreement; Amendment and Waiver. This Agreement
               --------------------------------------
     constitutes the entire understanding of the parties hereto and supersedes
     all prior understanding among such parties. This Agreement may be amended,
     and the observance of any term of this Agreement may be waived, with (and
     only with) the written consent of the Company, Landmark and the Holders
     holding a majority of the then outstanding Registrable Securities held by
     the Current Investors.

          (h)  Severability. In the event that any part or parts of this
               ------------
     Agreement shall be held illegal or unenforceable by any court or
     administrative body of competent jurisdiction, such determination shall not
     affect the remaining provisions of this Agreement which shall remain in
     full force and effect.

          (i)  Counterparts. This Agreement may be executed in one or more
               ------------
     counterparts, each of which shall be deemed an original and all of which
     together shall be considered one and the same agreement.

                                      -16-
<PAGE>

     IN WITNESS WHEREOF, the undersigned have executed this Agreement as of the
date first set forth above.

                              COOLSAVINGS.COM INC.

                              By: /s/ Matthew Moog
                                 --------------------------------------
                                 Name: Matthew Moog
                                 Title: President & CEO

                              LANDMARK VENTURES VII, LLC

                              By: /s/ Richard A. Fraim
                                 --------------------------------------
                                 Name: Richard A. Fraim
                                 Title: VP/Sec/Treasurer

                              LEND LEASE INTERNATIONAL PTY.
                                LIMITED [ACN# 000489109]

                              By: /s/ Mark Skinner
                                 --------------------------------------
                                 Name: Mark Skinner
                                 Title: Power of Attorney

                        [Registration Rights Agreement]

<PAGE>

                              STEVEN M. GOLDEN

                              /s/ Steven M. Golden
                              -----------------------------------------

                              STEVEN M. GOLDEN REVOCABLE LIVING
                                   TRUST DATED 3/3/98

                              By: /s/ Steven M. Golden
                                 --------------------------------------
                                 Name: Steven M. Golden
                                 Title: Trustee

                              STEVEN M. GOLDEN L.L.C.

                              By: /s/ Steven M. Golden
                                 --------------------------------------
                                 Name: Steven M. Golden
                                 Title: member

                              MATTHEW MOOG

                              /s/ Matthew Moog
                              -----------------------------------------

                              RICHARD H. ROGEL

                              /s/ Richard H. Rogel
                              -----------------------------------------

                              RICHARD H. ROGEL REVOCABLE LIVING
                                   TRUST DATED 3/21/90

                              By: /s/ Richard H. Rogel
                                 --------------------------------------
                                 Name: Richard H. Rogel
                                 Title:

                        [Registration Rights Agreement]

<PAGE>

                              RICHARD ROGEL -- CHARITABLE
                                   REMAINDER TRUST

                              By: /s/ RICHARD H. ROGEL
                                 --------------------------------------
                                 Name: RICHARD H. ROGEL
                                 Title:

                              HUGH R. LAMLE

                              /s/ HUGH R. LAMLE
                              -----------------------------------------

                              HLBL FAMILY PARTNERS LP

                              By: /s/ HUGH R. LAMLE
                                 --------------------------------------
                                 Name:
                                 Title: Managing G.P.

                              RONALD G. ZACK, M.D.

                              /s/ Ronald Zack
                              -----------------------------------------

                        [Registration Rights Agreement]

<PAGE>

                                   SCHEDULE I

                               CURRENT INVESTORS
<TABLE>
<CAPTION>

Investor Name                                    Investor Address
------------------------------------------------------------------------------------------------
<S>                                              <C>
Lend Lease International Pty. Limited            Level 44 Australia Square
[ACN# 000489109]                                 Sydney, Australia 2000

Steven M. Golden                                 360 N. Michigan Ave., 19/th/ Floor
                                                 Chicago, Illinois 60601

Steven M. Golden Revocable Living Trust dated    360 N. Michigan Ave., 19/th/ Floor
3/3/98; Steven M. Golden as Trustee              Chicago, Illinois 60601

Steven M. Golden L.L.C.                          360 N. Michigan Ave., 19/th/ Floor
                                                 Chicago, Illinois 60601

Matthew Moog                                     360 N. Michigan Ave., 19/th/ Floor
                                                 Chicago, Illinois 60601

Richard H. Rogel                                 416 Shooting Star
                                                 P.O. Box 1659
                                                 Avon, Colorado 81620

Richard H. Rogel Revocable Living Trust dated    416 Shooting Star
3/31/90                                          P.O. Box 1659
                                                 Avon, Colorado 81620

Richard Rogel -- Charitable Remainder Trust      416 Shooting Star
                                                 P.O. Box 1659
                                                 Avon, Colorado 81620

Hugh R. Lamle                                    M.D. Sass Investor Services, Inc.
                                                 1185 Avenue of the Americas
                                                 New York, New York 10036-2699

HLBL Family Partners LP                          M.D. Sass Investor Services, Inc.
                                                 1185 Avenue of the Americas
                                                 New York, New York 10036-2699

Ronald G. Zack, M.D.                             18211 W. Twelve Mile Road
                                                 Lathrup Village, MI 48076

------------------------------------------------------------------------------------------------
</TABLE>

<PAGE>

                                  SCHEDULE II

                                 1998 Holders

<TABLE>
<CAPTION>
-----------------------------------------------------------------------------------
Investor Name                             Investor Address
-----------------------------------------------------------------------------------
<S>                                       <C>
Lend Lease International Pty Limited      Level 44 Australia Square
[ACN# 000489109]                          Sydney, Australia 2000

-----------------------------------------------------------------------------------
Steven M. Golden Revocable Living Trust   360 N. Michigan Avenue, 19/th/ Floor
dated 3/3/98; Steven M. Golden as         Chicago, Illinois 60601
Trustee

-----------------------------------------------------------------------------------
Steven M. Golden L.L.C.                   360 N. Michigan Avenue, 19/th/ Floor
                                          Chicago, Illinois 60601

-----------------------------------------------------------------------------------
Hugh R. Lamle                             c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
HLBL Family Partners LP                   c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
Richard H. Rogel Revocable Living Trust   416 Shooting Star
dated 3/21/90                             P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
Richard Rogel - Charitable Remainder      416 Shooting Star
Trust                                     P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
</TABLE>

<PAGE>

                                  SCHEDULE III

                                  2001 Holders

<TABLE>
<CAPTION>
-----------------------------------------------------------------------------------
Investor Name                             Investor Address
-----------------------------------------------------------------------------------
<S>                                       <C>
Hugh R. Lamle                             c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
HLBL Family Partners LP                   c/o M.D. Sass Investor Services, Inc.
                                          1185 Avenue of the Americas
                                          New York, NY 10036-2699

-----------------------------------------------------------------------------------
Richard H. Rogel Revocable Living Trust   416 Shooting Star
dated 3/21/90                             P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
Richard Rogel - Charitable Remainder      416 Shooting Star
Trust                                     P.O. Box 1659
                                          Avon, CO 81620

-----------------------------------------------------------------------------------
Ronald G. Zack, M.D.                      18211 W. Twelve Mile Road
                                          Lathrup Village, MI 48076

-----------------------------------------------------------------------------------
</TABLE><PAGE>

                                                                    Exhibit 10.1

                             AMENDED AND RESTATED
                             --------------------
                  SENIOR SECURED LOAN AND SECURITY AGREEMENT
                  ------------------------------------------

                                                             Date: July 30, 2001

     THIS AMENDED AND RESTATED SECURED LOAN AND SECURITY AGREEMENT (hereinafter,
the "Agreement") is made between Landmark Communications, Inc. (hereinafter,
     ---------
"Lender"), a corporation organized and existing under the laws of the State of
-------
Virginia having an office at 150 W. Brambleton Avenue, Norfolk, VA 23510, and
coolsavings.com inc. (hereinafter, "Borrower"), a Michigan corporation with its
                                    --------
principal executive offices at 360 N. Michigan Ave., 19/th/ Floor, Chicago, IL
60601, in consideration of the mutual covenants contained herein and benefits to
be derived herefrom.  This Agreement supersedes that certain Loan and Security
Agreement, dated as of June 14, 2001, by and between the Lender and the Borrower
(the "Original Agreement").  The Master Note that was made by the Borrower in
      ------------------
favor of the Lender pursuant to the Original Agreement shall be amended and
restated in its entirety by the Borrower and the Lender on the terms and
conditions of the Senior Secured Note attached hereto as Exhibit A (the "Note").
                                                         ---------       ----
All capitalized terms shall have the respective meanings ascribed to them in
Exhibit B hereto.
---------

                             W I T N E S S E T H:
                             -------------------

                                  ARTICLE 1.

                                  THE LOAN

     1.1.  Initial Loan and Advances.
           -------------------------

           (a)  For value received Borrower unconditionally promises to pay to
the order of Lender on the Maturity Date (as defined below), without offset, the
original principal sum of Five Million Dollars ($5,000,000.00) (the "Original
                                                                     --------
Principal Amount") with interest on the outstanding principal amount which shall
----------------
accrue and compound thereon at the interest rates set forth below (the "Initial
                                                                        -------
Loan") and as set forth in the Note.
----
           (b)  For value received Borrower unconditionally promises to pay to
the order of Lender ON DEMAND, without offset, the unpaid principal amount of
any and all sums advanced to the Borrower at the Lender's sole discretion, from
time to time (an "Advance") and outstanding under that certain Commercial Demand
                  -------
Grid Note attached hereto as Exhibit C (the "Grid Note") together with interest
                             ---------       ---------
on each and all such Advances from the date of any such Advance which shall
accrue and compound thereon at the interest rates set forth below (the Initial
Loan together with any and all Advances, the "Loan"). Notwithstanding the
                                              ----
foregoing, the aggregate amount of any Advances under the Grid Note shall at no
time exceed Five Million Dollars ($5,000,000). Lender shall not be obligated to
make any Advance to Borrower at any time and should Lender, in its sole
discretion, make an Advance, the decision to evidence Borrower's repayment
obligation with respect thereto under the Grid Note shall also be at Lender's
sole discretion. The Grid Note shall be a demand obligation which shall be
payable by the Borrower at Lender's demand at any time and from time to time.
For purposes of this
<PAGE>

Agreement, "Advance" shall be deemed to include any reimbursement obligation of
Borrower to Lender that Lender records as an advance under the Grid Note.

           (c)  As additional consideration for the Initial Loan, the Borrower
shall issue to the Lender a warrant to purchase common stock of the Borrower in
the form attached hereto as Exhibit D (the "Initial Warrant").
                            ---------       ---------------

     1.2.  Interest on the Initial Loan and Repayment.
           ------------------------------------------

           (a)  The outstanding principal amount on the Initial Loan shall bear
interest at the rate of twelve percent (12%) per annum; provided, however, that
                                                        --------  -------
if the First Tranche Closing as such term is defined in that certain Securities
Purchase Agreement, dated as of July 30, 2001, by and among the Borrower, the
Lender and Landmark Ventures VII, LLC (the "Purchase Agreement") is consummated,
                                            ------------------
then from and after the date of such Closing the Initial Loan (including the
outstanding principal and interest that has then accrued) shall bear interest at
the rate of eight percent (8%) per annum. Interest shall be computed on the
actual number of days elapsed on the basis of a year consisting of 360 days. All
interest shall accrue and compound quarterly on: October 31, January 31, April
30 and July 31 of each year (each such date, a "Quarterly Payment Date"). Such
                                                ----------------------
accrued and compounded interest shall be added to the principal amount of the
Note.

           (b)  Notwithstanding the foregoing, any amount outstanding under the
Initial Loan shall bear interest from and after the Maturity Date at the rate of
sixteen (16%) per annum (the "Default Interest Rate"), increasing monthly by an
                              ---------------------
annual rate which is one (1) percentage point above the then current Default
Interest Rate for each month that the Note remains overdue. Any interest on the
Initial Loan accruing after the Maturity Date shall accrue and be compounded
monthly (the date of such compounding, the "Monthly Compounding Date" and
                                            ------------------------
collectively with the Quarterly Payment Date, the "Compounding Date") until the
                                                   ----------------
obligation of Borrower, with respect to the payment of such interest, has been
discharged (whether before or after judgment). Such accrued and compounded
interest shall be added to the principal amount of the Note.

           (c)  Notwithstanding the foregoing, the effective annual rate under
the Initial Loan (including the Default Interest Rate) shall not exceed a
maximum annual rate of twenty-four (24%) percent or the maximum annual rate
permitted by law, whichever is less.

           (d)  The Initial Loan shall be paid in full on the Maturity Date.
Until the Initial Loan is paid in full, on each Compounding Date, in lieu of a
cash payment of the interest due, Borrower shall pay such interest "in-kind". In
lieu of delivering separately documented and certificated promissory notes (the
"Note PIK Payment") and warrants (the "Warrant PIK Payment") for such "in-kind"
 ----------------                      -------------------
payments, the Note PIK Payment shall be effected by adding the accrued interest
to the principal amount of the Note (as described by the compounding in Sections
1.2(a) and 1.2(b) above) and the Warrant PIK Payment shall be effected through
the provision in the Initial Warrant which provides that for every dollar of
interest accrued, compounded and added to the principal amount of the Initial
Loan, the aggregate number of shares of Borrower's common stock that may be
purchased under the Initial Warrant shall be increased by two (2) (as such
number may be adjusted for dividends, splits, combinations and the

                                      -2-
<PAGE>

like). The foregoing notwithstanding, no Warrant PIK Payment shall be required
until after the First Tranche Closing and then only in respect of interest
payments accruing thereafter under the Initial Loan. Lender acknowledges that
the amount of the Note PIK Payment shall be deemed an additional loan borrowed
from the Lender (it being further acknowledged by the Borrower that it shall not
receive additional funds in connection with any such loan).

           (e)  Borrower may not prepay the Initial Loan except as follows: On
or after the third anniversary of the date hereof, the Borrower may prepay the
Note if and only if (i) the Borrower has had earnings and positive cash flow
during the most recent four fiscal quarters prior to such payment, (ii) Borrower
has no Indebtedness outstanding other than the Initial Loan, the Senior Secured
Note and trade payables incurred in the ordinary course of business (none of
which shall be more than ninety (90) days past due), (iii) the Quick Ratio set
forth in 4.12 below, immediately after giving effect to the prepayment, will be
2 to 1 and the Working Capital, also immediately after giving effect to the
prepayment, will be a net positive of $3 million, and (iv) Borrower's chief
financial officer has certified to Lender in writing (including supporting
computations) that each of the foregoing conditions is satisfied.

     1.3.  Interest on any Advances.
           ------------------------

           (a)  The outstanding principal amount on any Advances hereunder shall
bear interest at the rate of eight percent (8%) per annum. Interest shall be
computed on the actual number of days elapsed on the basis of a year consisting
of 360 days.

           (b)  Any amounts outstanding under any Advances hereunder that shall
have been demanded by the Lender hereto and not paid shall bear interest from
and after the date of such applicable demand at the rate of sixteen (16%) per
annum (the "Demand Interest Rate"), increasing monthly by an annual rate which
            --------------------
is one (1) percentage point above the then current Demand Interest Rate for each
month that the Grid Note remains overdue. Any interest on the Advances shall
accrue and be compounded monthly until the obligation of Borrower, with respect
to the payment of such interest, has been discharged (whether before or after
judgment).

           (c)  Notwithstanding the foregoing, the effective annual rate under
the Advances (including the Demand Interest Rate) shall not exceed a maximum
annual rate of twenty-four (24%) percent or the maximum annual rate permitted by
law, whichever is less.

           (d)  Borrower may prepay the Grid Note at any time and from time to
time.

     1.4.  Priority of Payment.
           -------------------

           (a)  All payments under the Loan shall be made to Lender at its
address specific above, or at such other address as Lender may specify in
writing to Borrower. All payments received from Borrower hereunder shall be
applied, at the option of Lender, first in payment of any costs or expenses of
Lender due to Lender pursuant to the terms of this Agreement, second in payment
of interest accrued and unpaid on the Grid Note, third in payment of the
outstanding principal balance of the Grid Note, and, when prepayment is
permitted, fourth to the payment of interest accrued and unpaid on the Note, and
fifth, to reduce the principal balance of the Note.

                                      -3-
<PAGE>

           (b)  At Lender's sole discretion, Lender may forgive any portion of
any principal or interest amounts due under the Grid Note and unpaid as
effective payment of any portion of the exercise price of any warrants to
purchase common stock of Borrower that Lender then holds and wishes to exercise.
Any payments of expenses, principal or interest shall be made in lawful money of
the United States of America.

     1.5.  Maturity Date of the Initial Loan. Borrower shall pay all outstanding
           ---------------------------------
principal and unpaid accrued interest on the Note in full on January 26, 2002
(the "Maturity Date"); provided, however, that, if the transactions contemplated
      -------------
under the Purchase Agreement are consummated, the Maturity Date of the Note
shall be June 30, 2006. Notwithstanding the foregoing if any amount under the
Initial Loan or any Advances are not paid in full when due or demanded, whether
at maturity, by acceleration or otherwise (the "Default Date"), the Maturity
                                                ------------
Date shall be the Default Date.

     1.6.  Change of Control. If at any time after the date of this Agreement
           -----------------
and prior to the Maturity Date, Borrower shall undergo a Change of Control, then
the holder hereof shall have the option to accelerate the Maturity Date to the
date of the consummation of such Change of Control and demand payment of all
outstanding principal and unpaid accrued interest on the Note and the Grid Note
in full in lawful money of the United States of America payable at the principal
office of Lender, or at such other place as Lender may specify in writing to
Borrower.

     1.7.  Use of Proceeds.  The proceeds of the Loan shall be used solely for
           ---------------
general working capital purposes.

                                  ARTICLE 2.

                          GRANT OF SECURITY INTEREST

     2.1.  Grant of Security Interest. To secure Borrower's prompt, punctual,
           --------------------------
and faithful performance of all and each of Borrower's Liabilities, Borrower
hereby grants to Lender a continuing security interest in and to, and assigns to
Lender, the following, and each item thereof, whether now owned or now due, or
in which Borrower has an interest, or hereafter acquired, arising, or to become
due, or in which Borrower obtains an interest, and all products, proceeds,
substitutions, and accessions of or to any of the following (all of which,
together with any other property in which Lender may in the future be granted a
security interest, is referred to herein as the "Collateral"):
                                                 ----------
           (a)  All Accounts and Accounts Receivable (including health-care-
insurance receivables);

           (b)  All Inventory;

           (c)  All Contract Rights (or other rights to the payment of money);

           (d)  All General Intangibles (including without limitation all
intellectual property, payment intangibles, patents, patent applications,
trademarks, trademark applications, trade names, copyrights, copyright
applications, engineering drawings, service marks, and all licenses, permits,
agreements of any kind or nature pursuant to which Borrower possesses, uses

                                      -4-
<PAGE>

or has authority to possess or use property (whether tangible or intangible) of
others or others possess, use or have authority to possess or use property
(whether tangible or intangible) of Borrower);

           (e)  All Investment Property;

           (f)  All Equipment (and any accessions thereto);

           (g)  All Goods;

           (h)  All Fixtures;

           (i)  All Chattel Paper (whether tangible or electronic);

           (j)  All books, records, and information relating to the Collateral
and/or to the operation of Borrower's business, and all rights of access to such
books, records, and information, and all property in which such books, records,
and information are stored, recorded and maintained;

           (k)  All software, computer programs, customer lists, tax refunds,
goodwill, trade secrets, and other recorded data, including without limitation
writings, plans, specifications and schematics, and all rights relating to the
foregoing;

           (l)  All Instruments (including promissory notes), Documents of
Title, Documents, policies and certificates of insurance, Securities and all
other investment property, supporting obligations, deposits, deposit accounts,
letter-of-credit rights (whether or not the letter of credit is evidenced by a
writing), commercial tort claims, general tort claims, impressed accounts,
compensating balances, money, cash, or other property;

           (m)  All insurance claims and proceeds, refunds and premium rebates,
including, without limitation, proceeds of fire and credit insurance, whether
any of such proceeds, refunds, and premium rebates arise out of any of the
foregoing ((a) - (1)) or otherwise; and

           (n)  All liens, guaranties, rights, remedies, and privileges
pertaining to any of the foregoing including the right of stoppage in
transit.

           (o)  Any and all Bank Collateral and Additional Bank Collateral as
such terms are defined in Section 2(h) of the Forbearance and Reaffirmation
Agreement dated as of June 15, 2001, as amended July 27, 2001, by and between
American National Bank and Trust Company ("ANB") and the Borrower (the "ANB
                                           ---                          ---
Forbearance Agreement").
---------------------

     2.2.  Extent and Duration of Security Interest.  This grant of a security
           ----------------------------------------
interest is in addition to, and supplemental of, any security interest
previously granted by Borrower to Lender, is applicable to all Liabilities, and
shall continue in full force and effect until all Liabilities have been paid
and/or satisfied in full and the security interest granted herein is
specifically terminated in writing by a duly authorized officer of Lender.

                                      -5-
<PAGE>

                                  ARTICLE 3.

               GENERAL REPRESENTATIONS, WARRANTIES AND COVENANTS

     To induce Lender to establish the loan arrangement contemplated herein and
to make loans and advances and to provide financial accommodations hereunder,
each of which loans shall be deemed to have been made in reliance thereupon,
Borrower, in addition to all other representations, warranties, and covenants
made by Borrower in any other Loan Document, makes the following
representations, warranties, and covenants.

     3.1.  Due Organization. Borrower presently is and shall hereafter remain in
           ----------------
good standing as a corporation in its state of formation and is and shall
hereafter remain duly qualified and in good standing in every other State in
which, by reason of the nature or location of Borrower's assets or operation of
Borrower's business, such qualification may be necessary and the failure to be
so qualified would have a Material Adverse Effect on the Borrower or its
businesses.

     3.2.  Corporate Authorization. Borrower has all requisite corporate power
           -----------------------
and authority to execute and deliver to Lender all and each of the Loan
Documents to which Borrower is a party, and has and will hereafter retain all
requisite corporate power to perform all and singular of the Liabilities.

     3.3.  Enforceability. The Loan Documents have been duly executed and
           --------------
delivered by Borrower and are the legal, valid and binding obligations of
Borrower, enforceable against Borrower in accordance with their respective
terms.

     3.4.  Consents and Approvals; No Violations. The execution and delivery of
           -------------------------------------
the Loan Documents and the consummation of the transactions contemplated hereby
and thereby will not: (a) violate or conflict with any provision of the Charter
or bylaws of Borrower; or (b) breach, violate or constitute a material event of
default (or an event which with the lapse of time or the giving of notice or
both would constitute a material event of default) under, give rise to any right
of termination, cancellation, modification or acceleration under, or require any
consent or the giving of any notice under, any note, bond, indenture, mortgage,
security agreement, lease, license, franchise, permit, agreement or other
instrument or obligation to which Borrower is a party, or by which Borrower or
any of its properties or assets may be bound, or result in the creation of any
material lien, claim or encumbrance or other right of any third party of any
kind whatsoever upon the properties or assets of Borrower pursuant to the terms
of any such instrument or obligation (other than any breach, violation or
default that has been expressly waived in connection herewith) and other than
any liens granted pursuant to the Loan Documents. All of the representations and
warranties under the Original Agreement were and are, respectively, true and
correct in all respects at and as of the date of the Original Agreement and on
and as of the date hereof (as though made on and as of the date hereof).

     3.5.  Title to Properties; Security Interest. Borrower has good and valid
           --------------------------------------
title to all personal property, tangible or intangible, which Borrower purports
to own and which is pledged hereunder, including the properties reflected on the
Balance Sheet or acquired after the date thereof (other than properties and
assets sold or otherwise disposed of in the ordinary course of

                                      -6-
<PAGE>

business and consistent with past practice since the Statement Date), free and
clear of any claims, liens, pledges, security interests or encumbrances of any
kind whatsoever, except those in favor of Lender, subject only to the prior
security interests granted to ANB and Midwest Guaranty Bank (solely with respect
to equipment leases). The security interests granted to Lender in the Collateral
constitute valid and perfected security interests in the Collateral.

     3.6.  Name; Location of Chief Executive Office; Location of Collateral.
           ----------------------------------------------------------------
Except as disclosed on Schedule 3.6, Borrower has not done business and will
                       ------------
not, without at least thirty (30) days prior written notice to Lender, do
business under any name other than that specified in the preamble above. The
chief executive office of Borrower is located at the address indicated in the
preamble above. Schedule 3.6 is a complete and accurate list of every location
at which any of the Collateral is located. Borrower shall not effect the Merger
contemplated under the Purchase Agreement unless and until (a) the surviving
corporation assumes all of Borrower's obligations hereunder and (b) Borrower
takes all steps required to preserve and maintain Lender's perfected security
interests in the Collateral, subject only to the prior security interests
granted to ANB and Midwest Guaranty Bank (solely with respect to equipment
leases).

     3.7.  Representations, Warranties, and Covenants Contained in Purchase
           ----------------------------------------------------------------
Agreement.  Borrower represents, warrants and covenants that all of the
representations, warranties, and covenants made by Borrower under the Purchase
Agreement are true and complete as of the date hereof, and agrees that such
representations, warrants and covenants are incorporated and made part of this
Agreement by reference and shall continue in full force and effect regardless of
any termination of such Purchase Agreement or any survival limitation therein.

     3.8.  Disclosure. No representation or warranty by Borrower contained in
           ----------
this Agreement or the Purchase Agreement and no statement contained in any
schedule, certificate or other document or instrument delivered or to be
delivered pursuant to the Loan Documents by Borrower or its representatives
contains or will contain any untrue statement of a material fact or omits or
will omit to state any material fact necessary to make the statements contained
therein not misleading when made.

                                  ARTICLE 4.

                             AFFIRMATIVE COVENANTS

     Borrower covenants and agrees that, until payment in full of the
outstanding Liabilities or for so long as Lender may have any commitment to make
any loans or advances, Borrower will continue to do all of the following:

     4.1.  Payment of Obligations. Punctually pay the principal of and interest
           ----------------------
on the Liabilities, at the times and places, in the manner and in accordance
with the terms of this Agreement, the Note, the Grid Note, and the other Loan
Documents.

     4.2.  Conduct of Business and Maintenance of Existence. Continue to engage
           ------------------------------------------------
in business of the same general type as now being conducted by the Borrower, and
do and cause to be done all things necessary to maintain and keep in full force
and effect its corporate existence in good standing in each jurisdiction in
which it conducts business.

                                      -7-
<PAGE>

     4.3.  Compliance with Laws, Etc. Comply in all material respects with all
           --------------------------
laws, statutes, ordinances, orders, rules or regulations applicable to the
Borrower or to the Collateral (or any part thereof) or to any other property
owned, leased, operated or used by the Borrower, including, without limitation,
environmental laws, the violation of which would have a material adverse effect
on the business, operations, properties or financial condition of the Borrower;
provided, Lender acknowledges that Borrower is currently not in compliance to
the extent described in Schedule 3.12 of the Purchase Agreement; and, provided,
                        -------------
further that notwithstanding such acknowledgement Borrower shall use its best
efforts to promptly cure such non-compliance and nothing herein shall be deemed
or construed to excuse or otherwise modify Borrower's indemnification
obligations under the Purchase Agreement with respect to such matters.

     4.4.  Payment of Liabilities and Taxes. Pay, when due, all of its
           --------------------------------
Indebtedness and liabilities, and pay and discharge promptly all taxes,
assessments and governmental charges and levies (including, without limitation,
F.I.C.A. payments and withholding taxes) upon the Borrower or upon the
Borrower's income, profits or property (including, without limitation, the
Collateral), except to the extent the amount or validity thereof is contested in
good faith by appropriate proceedings so long as adequate reserves have been set
aside therefor. It is acknowledged that existing payment defaults have been
disclosed under Schedule 3.8 of the Purchase Agreement and that such defaults
shall be cured in the manner described in Section 5.15 of the Purchase
Agreement.

     4.5.  Contractual Obligations.  Comply with any agreement or undertaking to
           -----------------------
which the Borrower is a party and maintain in full force and effect all
contracts and leases to which the Borrower is or becomes a party unless the
failure to do so would not have a material adverse effect on the business,
operation, properties or financial condition of the Borrower.

     4.6.  Maintenance of Properties. Do all things necessary to maintain,
           -------------------------
preserve, protect and keep its properties in good repair, working order and
condition, and make all necessary and proper repairs, renewals and replacements
so that the Borrower's business may be properly conducted at all times, unless
the failure to do so would not have a material adverse effect on the business,
operation or financial condition of the Borrower. The Borrower shall promptly
notify the Lender of any event causing deterioration, loss or depreciation in
value of any substantial portion of the Collateral and the amount of such loss
or depreciation. The Borrower shall perform, observe, and comply with all of the
terms and provisions to be performed, observed or complied with by it under each
contract, agreement or obligation relating to the Collateral. The Lender shall
have no duty to, and the Borrower hereby releases the Lender from all claims for
loss or damage caused by the failure of the Lender to, collect, protect,
preserve or enforce any of the Collateral or preserve rights against account
debtors and prior parties to the Collateral.

     4.7.  Insurance.
           ---------
           (a)  Borrower, at its expense, shall keep the Collateral insured
against loss or damage by fire, theft, explosion, sprinklers, and all other
hazards and risks, and in such amounts, as ordinarily insured against by other
owners in similar businesses conducted in the locations where Borrower's
business is conducted. Borrower shall also maintain insurance relating to
Borrower's ownership and use of the Collateral in amounts and of a type that are
customary to

                                      -8-
<PAGE>

businesses similar to Borrower's. Borrower shall also maintain liability
insurance and worker's compensation insurance.

           (b)  All such policies of insurance shall be in such form, with such
companies, and in such amounts as are reasonably satisfactory to Lender. All
such policies of property insurance shall contain a lender's loss payable
endorsement, in a form satisfactory to Lender, showing Lender as an additional
loss payee thereof and all liability insurance policies shall show the Lender as
an additional insured, and shall specify that the insurer must give at least
twenty (20) days notice to Lender before canceling its policy for any reason. At
Lender's request, Borrower shall deliver to Lender certified copies of such
policies of insurance and evidence of the payments of all premiums therefor. All
proceeds payable under any such policy shall, at the option of Lender, be
payable to Lender.

     4.8.  Inspection.  Permit the Lender, by its representatives and agents, to
           ----------
inspect any of the properties, books and financial records of the Borrower, to
examine and make copies of the books of accounts and other financial records of
the Borrower, and to discuss the affairs, finances and accounts of the Borrower
with, and to be advised as to the same by, the Borrower (or its representatives)
at such reasonable times and intervals as the Lender may designate.  In
connection with the foregoing, the Lender and its representatives and agents, at
the expense of the Borrower, shall have the right to (a) enter any business
premises of the Borrower or any other premises where the Collateral and the
records relating thereto may be located and to audit, appraise, examine and
inspect the Collateral and all records related thereto and to make extracts
therefrom and copies thereof, and (b) verify under reasonable procedures the
validity, amount, quality, quantity, value and condition of, and any other
matter relating to, the Collateral, including contacting account debtors or any
person possessing any of the Collateral.

     4.9.  Collection of Receivables Collateral. Collect its Receivables
           ------------------------------------
Collateral only in the ordinary course of business consistent with Borrower's
past practices, and shall not, without the Lender's prior written consent unless
done so in the ordinary course of business consistent with past practices made
known to the Lender in writing, compromise or adjust the amount of any
Receivable Collateral or extend the time for payment of any Receivable
Collateral.

     4.10. Further Assurances. Defend the title of the Borrower to the
           ------------------
Collateral and the security interest and lien thereon of the Lender against all
persons and against all security interests and liens on the Collateral adverse
to those of the Lender. The Borrower will, from time to time, at the expense of
the Borrower, execute, deliver, acknowledge and cause to be duly filed, recorded
or registered any statement, assignment, instrument, paper, agreement or other
document and take any other action that from time to time may be necessary or
desirable, or that the Lender may reasonably request, in order to create,
preserve, continue, perfect, confirm or validate the security interest and lien
of the Lender on the Collateral or to enable the Lender to obtain the full
benefits of this Agreement or to exercise and enforce any of its rights, powers
and remedies hereunder or under applicable laws. The Borrower shall pay all
costs of, and incidental to, the filing, recording or registration of any such
document as well as any recordation, transfer or other tax required to be paid
in connection with any such filing, recordation or registration. The Borrower
hereby covenants to save harmless and indemnify the Lender from and against any
liability resulting from the failure to pay any required documentary stamps,
recordation and transfer taxes and recording costs incurred by the Lender in
connection with this Agreement or

                                      -9-
<PAGE>

the Collateral which covenant shall survive the termination of this Agreement
and the payment of all other Liabilities. The Borrower agrees that a carbon,
photographic, photostatic or other reproduction of this Agreement or of a
financing statement signed by the Borrower in connection with this Agreement
shall be sufficient as a financing statement. If any Receivable Collateral
arises out of a contract with the United States of America or any state, county,
municipality or any department, agency or instrumentality thereof, the Borrower
shall immediately notify the Lender thereof and, if required by the Lender,
execute and deliver any agreements, notices and/or assignments and do such other
things as may be satisfactory to the Lender in order that all sums due or to
become due to the Borrower under such contract shall be duly assigned to the
Lender in accordance with the Federal Assignment of Claims Act and/or any other
applicable federal, state and local laws or regulations relating to the
assignment of governmental obligations. If, in the reasonable opinion of the
Lender, any Equipment is or may become a part of any real estate owned or leased
by the Borrower, the Borrower will, upon the request of the Lender, use its best
efforts to furnish to the Lender in form and content satisfactory to the Lender,
a landlord's waiver by the record owner of such real estate and a mortgagee's
waiver by any person who has a security interest or lien on such real estate
which is or may be superior to the security interest and lien of the Lender on
such Equipment.

     4.11.  Notice.  Promptly give written notice to the Lender of (a) the
            ------
occurrence of any Default or any event, development or circumstance which might
materially adversely effect the business, operations, properties or financial
condition of the Borrower, (b) any litigation instituted or threatened against
the Borrower or any judgment against the Borrower where claims against the
Borrower exceed $50,000 and are not covered in full by insurance, and (c) any
notice of a claim against, or investigation of, the Borrower, the Collateral or
any other property owned, leased, operated or used by the Borrower. Borrower
shall also promptly provide Lender with copies of all notices received from, or
required to be provided to, ANB or Midwest Guaranty Bank under the Forbearance
Agreements, or to any landlord from which the Borrower leases any real property
under any lease agreement.

     4.12.  Financial Covenants.
            -------------------

            (a)  Performance Against Forecast.  By e-mail dated July 27, 2001,
                 ----------------------------
Borrower delivered to Lender a "coolsaving.com (Conservative Case) Cash Source &
Use Forecast 2001 (Jun 18 to Dec 31)" (the "Conservative Forecast") 7/27/01
                                            ---------------------
12:00 AM./1/ During each calendar month in 2001 and each calendar quarter in
2002, Borrower shall comply with each of the following:

                 (i)  Borrower's Earned Cash Billings (defined below) shall not
be less than the "Invoicing (Est.) cash" amount for the applicable month or the
"[number] quarter 2002 cash" amount for the applicable quarter as set forth in
Section II of the Conservative Forecast (e.g., $1,998,000 for September 2001);

___________________________

/1/  For purposes of identification, the Conservative Forecast indicates
Projected Cash (Requirement) of $1,316,357.69 at 31-Dec-01 and ($5,075,595.70)
at 4th Quarter 2002.

                                      -10-
<PAGE>

          (ii)   Borrower's actual Costs of Services and actual Marketing
expenses shall not exceed the "Cost of Services" and "Marketing" amounts,
respectively (each, a "Cost Threshold"), for the applicable month or quarter as
set forth in Sections VI and VII of the Conservative Forecast (e.g., $235,224.10
in Costs of Services and $478,696 in Marketing for September 2001) unless the
amount by which the applicable Cost Threshold is exceeded in the applicable
month or quarter is offset on a dollar-for-dollar basis by the amount by which
the Earned Cash Billings exceed the "Invoicing (Est.) cash" amount in the
applicable month or quarter;

          (iii)  Borrower's actual capital expenditures shall be in an amount at
least equal to the "Capital Expenditure Budget" amount for the applicable month
or quarter as set forth in Section VII of the Conservative Forecast;

          (iv)   Borrower's actual accounts payable balance shall not exceed the
"Period Ending A/P balance" amount for the applicable month or quarter as set
forth in Section V of the Conservative Forecast by an amount more than the
lesser of (A) $100,000, or (B) 2% of the applicable "Period Ending A/P balance"
on the Conservative Forecast;

          (v)    Borrower's actual cash on hand shall not be less than 98% of
the "Projected Cash Requirement" amount for the applicable month or quarter as
set forth in Section IX of the Conservative Forecast; and

          (vi)   Borrower's bad debt experience with respect to the billings
rendered in a month or quarter, as applicable, shall not be more than 3% of the
Earned Cash Billings for such month or quarter.

Each item used or included for purposes of calculating an entry on the
Conservative Forecast (such as "Cost of Services") shall be consistently used
and included for purposes of calculating the "actual" amount of such entry in
the applicable test set forth above; provided, Earned Cash Billings shall be
calculated as provided below.

     (b)  Minimum Working Capital and Ratio.  Borrower shall maintain on a
          ---------------------------------
consolidated basis, as of the last day of each calendar month, Working Capital
(defined below) and a Quick Ratio (defined below) of at least the following
amounts at the following times:

   Minimum Working Capital        Quick Ratio                  Period
   -----------------------        -----------                  ------
  ($4,500,000; deficit            .3 to 1.0        through First Tranche Closing
  increasing by $1,500,000 for
  each month after 9/30/01 that
  First Tranche Closing is
        delayed)
        $200,000                  .4 to 1.0        First Tranche Closing through
                                                   Second Tranche Closing
        $600,000                  .5 to 1.0        Second Tranche Closing
                                                   through June 30, 2002
        $750,000                  1.0 to 1.0       July 1, 2002 through December
                                                   31, 2002
        $2,000,000                1.3 to 1.0       At all times thereafter

                                      -11-
<PAGE>

            (c)  Total Indebtedness to Tangible Net Worth.  Borrower shall
                 ----------------------------------------
maintain on a consolidated basis, as of the last day of each calendar month, a
ratio of Total Indebtedness (defined below) to Tangible Net Worth (defined
below) of at least the following amounts at the following times:

          Indebtedness/Net
          ----------------
           Worth Ratio:                                Period
           -----------                                 ------

             [N/A]                         through First Tranche Closing
           8.0 to 1.0                      First Tranche Closing through Second
                                           Tranche Closing
           2.0 to 1.0                      Second Tranche Closing through first
                                           four full fiscal quarters
                                           thereafter
           1.0 to 1.0                      At all times thereafter

            (d)  Total Indebtedness to EBITDA.  Borrower shall maintain on a
                 ----------------------------
consolidated basis, as of the last day of each calendar month, a ratio of Total
Indebtedness to EBITDA (defined below) of at least the following amounts at the
following times:

          Indebtedness/
          ------------
          EBITDA Ratio:                                Period:
          -------------                                ------
            3.0 to 1.0                 From and after December 31, 2002

            (e)  Compliance Certificate. Within fifteen (15) business days after
                 ----------------------
the end of each calendar month and twenty (20) days after the end of each
quarter, as applicable,, Borrower shall deliver to Lender a compliance
certificate, executed by Borrower's president and its chief financial officer
(and in a form reasonably satisfactory to Lender) which certifies Borrower's
compliance with the financial covenants in this Section 4.12 for the immediately
preceding month and quarter, as applicable.

     4.13.  Commercial Tort Claims. If Borrower shall at any time hold or
            ----------------------
acquire a commercial tort claim, Borrower shall immediately notify Lender in a
writing signed by Borrower of the brief details thereof and grant to Lender in
such writing a security interest therein and in the proceeds thereof, all upon
the terms of this Agreement, with such writing to be in form and substance
satisfactory to Lender.

     4.14.  Newly Created Intellectual Property. Borrower will promptly notify
            -----------------------------------
Lender of all new trademark, patent and copyright registrations and applications
for registration now or hereafter filed by Borrower.

                                  ARTICLE 5.

                              NEGATIVE COVENANTS

     Borrower covenants and agrees that, until payment in full of the
outstanding Liabilities, Borrower will not do any of the following:

                                      -12-
<PAGE>

     5.1.  Dispositions.  Convey, sell, lease, transfer or otherwise dispose of
           ------------
(collectively, a "Transfer"), all or any part of its business or property, other
                  --------
than Transfers: (i) of inventory in the ordinary course of business, (ii) of
non-exclusive licenses and similar arrangements for the use of the property of
Borrower in the ordinary course of business; (iii) that constitute payment of
normal and usual operating expenses in the ordinary course of business; or (iv)
of worn-out or obsolete equipment.

     5.2.  Changes in Business.  Engage in any business, other than the
           -------------------
businesses currently engaged in by Borrower and any business substantially
similar or related thereto (or incidental thereto). The Company acknowledges
that excessive e-mail transmissions, while promoting short-term revenue
increases, could have detrimental effects on the long term financial prospects
of the Company. The Company agrees to monitor the member opt-out rate and to not
transmit excessive member e-mails that could cause such opt-out rate to exceed
3.5%.

     5.3.   Dividends or Investments. Borrower shall not, without the prior
            ------------------------
written consent of Lender:

            (a)  Pay any cash dividend or make any other distribution in respect
of any class of Borrower's capital stock (other than dividends paid in kind with
respect to Borrower's Series B Preferred Stock);

            (b)  Own, redeem, retire, purchase, or acquire any of Borrower's
capital stock;

            (c)  Invest in or purchase any stock or securities or rights to
purchase any such stock or securities, of any corporation or other entity;

            (d)  Merge or consolidate or be merged or consolidated with or into
any other corporation or other entity or acquire all or substantially all of the
assets of any corporation or other entity;

            (e)  Consolidate any of Borrower's operations with those of any
other corporation or other entity;

            (f)  Organize or create any Related Entity; or

            (g)  Subordinate any debts or obligations owed to Borrower by any
third party to any other debts owed by such third party to any other Person.

     5.4.   Restrictions on Indebtedness; Expenditures and Material Obligations.
            -------------------------------------------------------------------

            (a)  Borrower shall not make any loans or advances to, nor acquire,
guarantee or otherwise become responsible for the Indebtedness of, any Person,
other than advance payments made to Borrower's suppliers in the ordinary course
or to Borrower's employees for travel and related expenses.

            (b)  Borrower shall not create, incur, assume or be or remain liable
with respect to Indebtedness, except for (i) Permitted Indebtedness and (ii)
trade indebtedness incurred in the ordinary course of business.

                                      -13-
<PAGE>

          (c)  Borrower shall not make any payment in respect of any
Indebtedness, except payments made in respect of (i) Permitted Indebtedness, to
the extent such payments are made in compliance with the terms of such Permitted
Indebtedness (and do not constitute prepayments, other than the prepayments
required under the terms of the Forbearance Agreements) and (ii) trade
indebtedness incurred in the ordinary course of business. Without limiting the
payments prescribed in the preceding sentence, Borrower shall not (A) make any
payment out of the ordinary course of business, (B) make any payment to any
shareholder or shareholder Affiliate (excluding payments made to Borrower and/or
its Affiliates) or any director, officer or employee (excluding employee
salaries, board fees and expense reimbursements in accordance with Borrower's
policies and procedures) or (C) make any payment that could cause Borrower to
breach the financial covenants made under this Agreement or prevent Borrower
from paying, when due, accrued dividends on its Series B Preferred Stock.

          (d)  Borrower shall not amend any provision contained in any
documentation relating to any Indebtedness (including Permitted Indebtedness)
without Lender's prior written consent.

          (e)  Borrower shall not make any material increases in annual salaries
of its employees outside of the ordinary course and consistent with past
practice.

          (f)  Borrower shall not enter into any material agreements, joint
venture agreements, license agreements, revenue sharing agreements, or other
arrangements which allocate revenues to a third party or obligate Borrower to
pay any kind of fees which, individually, would exceed $250,000 per year, or
$750,000 over the term such arrangement, or which when combined with all similar
arrangements would involve fees in excess of $2,000,000.

          (g)  Borrower shall not enter into any material agreements, joint
venture agreements, license agreements, revenue sharing agreements, alliances or
other arrangements which allocate revenues to a third party or obligate Borrower
to perform any services which on an arms length basis calculated at fair market
value, individually would exceed $250,000 per year, or $750,000 over the term of
such arrangement, or which when combined with all similar arrangements would
involve in kind services on an arms length basis calculated at fair market value
in excess of $2,000,000.

     5.5.  Transactions with Affiliates.  Directly or indirectly enter into any
           ----------------------------
material transaction with any Affiliate of Borrower or permit to exist any such
material transaction other than as set forth on Schedule 5.5 (which shall only
                                                ------------
list transactions existing through the date hereof) except for transactions that
are in the ordinary course of Borrower's business, upon fair and reasonable
terms that are no less favorable to Borrower than would be obtained in an arm's
length transaction with a nonaffiliated Person.

     5.6.  Executive Management. Borrower shall not change its Chief Executive
           --------------------
Officer, Chief Financial Officer, Chief Technology Officer, or Executive Vice
President, Business Development from those individuals occupying such positions
at the execution of this Agreement without the written consent of Lender.

                                      -14-
<PAGE>

     5.7.  Amendment to Forbearance Agreements; Additional Borrowings. Without
           ----------------------------------------------------------
the prior written consent of the Lender, the Borrower shall not (i) amend, alter
or terminate the ANB Forbearance Agreement or that certain Forbearance Agreement
between Midwest Guaranty Bank and the Borrower dated July 27, 2001, or that
certain Letter Agreement between 360 Michigan Trust and the Borrower dated June
14, 2001 (collectively, the "Forbearance Agreements") or (ii) incur any
                             ----------------------
additional indebtedness from ANB or Midwest Guaranty Bank at any time, whether
under existing loan documents or otherwise.

     5.8.  Change in Control. Borrower shall not, without the prior written
           -----------------
consent of Lender, change the ownership of the capital stock of Borrower such
that a Change of Control would result.

     5.9.  Changes in Business Locations or Incorporation.  Borrower will not,
           ----------------------------------------------
without at least thirty (30) days prior written notification to Lender, relocate
its chief executive office or add any new offices or business locations or
create any Subsidiary or reincorporate in any other jurisdiction (excluding the
reincorporation contemplated by the Merger).

     5.10. Encumbrances.  Create, incur, assume or suffer to exist any Lien with
           ------------
respect to any of its property, or assign or otherwise convey any right to
receive income, including the sale of any Accounts, except for permitted
Encumbrances hereunder.

                                  ARTICLE 6.

                               EVENTS OF DEFAULT

     The occurrence of any event described in this Article 6 shall constitute an
"Event of Default" herein.  Upon the occurrence of any Event of Default any and
 ----------------
all Liabilities shall become due and payable, without any further act on the
part of Lender.  Upon the occurrence of any Event of Default, or the entry of
any order for relief with respect to Borrower under the Bankruptcy Code, any and
all Liabilities of Borrower to Lender shall become immediately due and payable,
at the option of Lender and without notice or demand.  The occurrence of any
Event of Default shall also constitute, without notice or demand, a default
under all other agreements between Lender and Borrower and instruments and
papers given Lender by Borrower, whether such agreements, instruments, or papers
now exist or hereafter arise.

     6.1. Failure to Pay the Loan. The failure by Borrower to pay, when due, any
          -----------------------
amount under the Loan or any other Liability provided that such failure to pay
is not cured within five (5) business days.

     6.2.  Failure to Perform Covenant or Liability. Except for payment defaults
           ----------------------------------------
as set forth in Section 6.1, the failure by Borrower to promptly, punctually,
faithfully and timely to perform or discharge, or to comply with, any covenant
to or with Lender or any Liability, provided, however, that such failure or
breach is not cured within twenty (20) days from date of notice given by Lender
in the manner provided in Section 9.15; provided, further, that (a) no further
notice shall be required from Lender if Borrower has delivered to Lender a
certificate in which the breach or default is disclosed or is otherwise aware of
the breach or default as a result of written notices sent or received by
Borrower, and (b) the cure period under this Section 6.2 shall

                                      -15-
<PAGE>

be interpreted to run concurrently and not consecutively with Section 9.2(e) of
the Purchase Agreement.

     6.3.  Misrepresentation. The determination by Lender that any
           -----------------
representation or warranty at any time made by Borrower to Lender, including
without limitation any representation and warranty made under the Original
Agreement, this Agreement or the Purchase Agreement, was not true or complete in
all material respects (in all respects to the extent the representation or
warranty is qualified by a materiality standard) when given or has otherwise
been breached; provided, however, to the extent the breach relates to a breach
of a representation and warranty under the Purchase Agreement (which would
otherwise trigger an Event of Default under this Agreement by virtue of being
incorporated by reference), then an Event of Default hereunder shall not be
deemed to exist unless under the terms of the Purchase Agreement, Borrower or
its Affiliate is entitled to be indemnified for any Losses (as defined in the
Purchase Agreement) (any such breach as excepted hereunder is hereafter a
"Representation and Warranty Exception").

     6.4.  Acceleration of Other Debt. The occurrence of any event such that any
           --------------------------
Indebtedness of Borrower to any creditor other than Lender has been accelerated
and has not been cured within five (5) business days.

     6.5.  Default Under Other Agreements. The occurrence of any breach or
           ------------------------------
default under any agreement between Lender and Borrower (subject to
Representation and Warranty Exception) or under any of the Forbearance
Agreements (including for such purposes an event which, with or without notice
or the passage of time or both, would constitute a breach or default) including
without limitation any breach of a covenant, representation or warrant made
under this Agreement, the Forbearance Agreements, the Purchase Agreement, or any
instrument or paper given to Lender by Borrower, whether such agreement,
instrument, or paper now exists or hereafter arises (notwithstanding that Lender
may not have exercised its rights upon default under any such other agreement,
instrument or paper).

     6.6.  Termination of Purchase Agreement.  The termination of the Purchase
           ---------------------------------
Agreement prior to the First Tranche Closing, by any party thereto, pursuant to
Section 9.2 of the Purchase Agreement.

     6.7.  Failure to Pay Dividends; Redemption of Series B Preferred Stock. The
           ----------------------------------------------------------------
failure of the Borrower to declare or pay dividends on the Borrower's Series B
Preferred Stock or to redeem any shares of the Series B Preferred Stock pursuant
to the Borrower's Charter.

     6.8.  Casualty Loss; Non-Ordinary Course Sales.  The occurrence of any (a)
           ----------------------------------------
uninsured loss, theft, damage, or destruction of or to any material portion of
Borrower's assets, or (b) sale (other than sales in the ordinary course of
business) of the assets of Borrower.

     6.9.  Judgment; Restraint of Business.
           -------------------------------

           (a)  The service of process upon Lender seeking to attach, by
trustee, mense, or other process, any of Borrower's funds on deposit with, or
assets of Borrower in the possession of, Lender.

                                      -16-
<PAGE>

          (b)  The entry of any judgment against Borrower, which judgment is not
satisfied (if a money judgment) or appealed from (with execution or similar
process stayed) within fifteen (15) days of its entry.

          (c)  The entry of any order or the imposition of any other process
having the force of law, the effect of which is to restrain in any material way
the conduct by Borrower of its business in the ordinary course.

     6.10. Business Failure. Any act by, against, or relating to Borrower, or
           ----------------
its property or assets, which act constitutes the application for, consent to,
or sufferance of the appointment of a receiver, trustee, or other person,
pursuant to court action or otherwise, over all, or any part of Borrower's
property; the granting of any trust mortgage or execution of an assignment for
the benefit of the creditors of Borrower, or the occurrence of any other
voluntary or involuntary liquidation or extension of debt agreement for
Borrower; or the offering by or entering into by Borrower of any composition,
extension, or any other arrangement seeking relief from or extension of the
debts of Borrower, or the initiation of any other judicial or non-judicial
proceeding or agreement by, against, or including Borrower which seeks or
intends to accomplish a reorganization or arrangement with creditors (however,
it shall not be an Event of Default hereunder until the earlier of (x) the entry
of an order for relief against Borrower, or (y) the expiration of thirty (30)
days without dismissal of such complaint, application, or petition if such
complaint, application or petition filed against Borrower was not filed by or at
the direction of Borrower or any Related Entity, and is being diligently
contested).

     6.11.  Bankruptcy.  The failure by Borrower to generally pay the debts of
            ----------
Borrower as they mature; adjudication of bankruptcy or insolvency relative to
Borrower; the entry of an order for relief or similar order with respect to
Borrower in any proceeding pursuant to the Bankruptcy Code or any other federal
bankruptcy law; the filing of any complaint, application, or petition by or
against Borrower initiating any matter in which Borrower is or may be granted
any relief from the debts of Borrower pursuant to Bankruptcy Code or any other
insolvency statute or procedure (however, it shall not be an Event of Default
hereunder until the earlier of (x) the entry of an order for relief against
Borrower, or (y) the expiration of thirty (30) days without dismissal of such
complaint, application, or petition of such complaint, application or petition
filed against Borrower was not filed by or at the direction of Borrower or any
Related Entity, and is being diligently contested).

     6.12.  Michigan Law.  The opt-in or adoption by Borrower of any provisions
            ------------
whether in the Borrower's Charter, Bylaws or otherwise contained in Sections 7A
or 7B of the Michigan Business Corporation Act.

                                  ARTICLE 7.

                       RIGHTS AND REMEDIES UPON DEFAULT

     In addition to all of the rights, remedies, powers, privileges, and
discretions which Lender is provided prior to the occurrence of an Event of
Default, Lender shall, at its election, without notice of its election and
without demand, have the following rights and remedies upon the occurrence of
any Event of Default and at any time thereafter.

                                      -17-
<PAGE>

     7.1.  Rights of Enforcement. Lender shall have all of the rights and
           ---------------------
remedies of a secured party upon default under the UCC, in addition to which
Lender shall have all and each of the following rights and remedies, upon seven
(7) days notice to the Borrower:

           (a)  To collect the Receivables Collateral with or without the taking
of possession of any of the Collateral;

           (b)  To apply the Receivables Collateral or the proceeds of the
Collateral towards (but not necessarily in complete satisfaction of) the
Liabilities;

           (c)  To take possession of all or any portion of the Collateral;

           (d)  To sell, lease, or otherwise dispose of any or all of the
Collateral, in its then condition or following such preparation or processing as
Lender deems advisable and with or without the taking of possession of any of
the Collateral; and

           (e)  To exercise all or any of the rights, remedies, powers,
privileges, and discretions under all or any of the Loan Documents.

     7.2.  Sale of Collateral.
           ------------------

           (a)  Any sale or other disposition of the Collateral may be at public
or private sale upon such terms and in such manner as Lender deems advisable,
having due regard to compliance with any statute or regulation which might
affect, limit, or apply to Lender's disposition of the Collateral.

           (b) Unless the Collateral is perishable or threatens to decline
speedily in value, or is of a type customarily sold on a recognized market (in
which event Lender shall provide Borrower with such notice as may be practicable
under the circumstances), Lender shall give Borrower at least seven (7) days
prior written notice of the date, time, and place of any proposed public sale,
and of the date after which any private sale or other disposition of the
Collateral may be made. Borrower agrees that such written notice shall satisfy
all requirements for notice to Borrower which are imposed under the UCC or other
applicable law with respect to Lender's exercise of Lender's rights and remedies
upon default.

           (c)  Lender may purchase the Collateral, or any portion of it at any
sale held under this Article.

           (d)  Lender shall apply the proceeds of any exercise of Lender's
Rights and Remedies under this Article 7 towards the Liabilities in such manner,
and with such frequency, as Lender determines.

     7.3.  Collection of Accounts. Upon the occurrence and during the
           ----------------------
continuance of an Event of Default, Lender may notify any Person owing funds to
Borrower of Lender's security interest in such funds and verify the amount of
such funds. Borrower shall collect all amounts owing to Borrower for Lender,
receive in trust all payments as Lender's trustee, and if requested or required
by Lender immediately deliver such payments to Lender in their original form as
received from the account debtor, with proper endorsements for deposit.

                                      -18-
<PAGE>

     7.4.  Occupation of Business Location. In connection with Lender's exercise
           -------------------------------
of Lender's rights under this Article, Lender may enter upon, occupy, and use
any premises owned or occupied by Borrower, and may exclude Borrower from such
premises or portion thereof as may have been so entered upon, occupied, or used
by Lender. Lender shall not be required to remove any of the Collateral from any
such premises upon Lender's taking possession thereof, and may render any
Collateral unusable to Borrower. In no event shall Lender be liable to Borrower
for use or occupancy by Lender of any premises pursuant to this Article, nor for
any charge (such as wages for Borrower's employees and utilities) incurred in
connection with Lender's exercise of Lender's Rights and Remedies.

     7.5.  Grant of Nonexclusive License. Borrower hereby grants to Lender a
           -----------------------------
royalty-free, nonexclusive, irrevocable license to use, apply, and affix any
trademark, trade name, logo, or the like in which Borrower now or hereafter has
rights, such license being with respect to Lender's exercise of the rights
hereunder including, without limitation, in connection with any completion of
the manufacture of Inventory or sale or other disposition of Inventory.

     7.6.  Assembly of Collateral. Lender may require Borrower to assemble the
           ----------------------
Collateral and make it available to Lender at Borrower's sole risk and expense
at a place or places which are reasonably convenient to both Lender and
Borrower.

     7.7.  Rights and Remedies.  The rights, remedies, powers, privileges, and
           -------------------
discretions of Lender hereunder (herein, the "Lender's Rights and Remedies")
                                              ----------------------------
shall be cumulative and not exclusive of any rights or remedies which it would
otherwise have.  No delay or omission by Lender in exercising or enforcing any
of Lender's Rights and Remedies shall operate as, or constitute, a waiver
thereof.  No waiver by Lender of any Event of Default or of any default under
any other agreement shall operate as a waiver of any other default hereunder or
under any other agreement.  No single or partial exercise of any of Lender's
Rights or Remedies, and no express or implied agreement or transaction of
whatever nature entered into between Lender and any person, at any time, shall
preclude the other or further exercise of Lender's Rights and Remedies.  No
waiver by Lender of any of Lender's Rights and Remedies on any one occasion
shall be deemed a waiver on any subsequent occasion, nor shall it be deemed a
continuing waiver.  All of Lender's Rights and Remedies and all of Lender's
rights, remedies, powers, privileges, and discretions under any other agreement
or transaction are cumulative, and not alternative or exclusive, and may be
exercised by Lender at such time or times and in such order of preference as
Lender in its sole discretion may determine. Lender's Rights and Remedies may be
exercised without resort or regard to any other source of satisfaction of the
Liabilities.

                                  ARTICLE 8.

                               TERM OF AGREEMENT

     8.1.  Termination of Loan. The Loan shall terminate upon the earlier of (i)
           -------------------
the Maturity Date of the Initial Loan, (ii) after the occurrence of an Event of
Default or (iii) after a demand under the Grid Note that is not immediately paid
by the Lender. Upon such termination, all Liabilities under the Loan (and the
Note and Grid Note) shall be immediately due and payable in full.

                                      -19-
<PAGE>

                                  ARTICLE 9.

                                    GENERAL

     9.1.  Delivery of Additional Documentation Required. Borrower shall from
           ----------------------------------------------
time to time execute and deliver to Lender, at the request of Lender, all
Collateral, and all financing statements and other documents that Lender may
request, in form satisfactory to Lender, to perfect and continue to perfect
Lender's security interests in the Collateral (and ensure the priority thereof)
and in order to fully consummate all of the transactions contemplated under the
Loan Documents.

     9.2.  Successors and Assigns.
           ----------------------

           (a)  This Agreement shall be binding upon Borrower and Borrower's
representatives, successors, and assigns and shall inure to the benefit of
Lender and Lender's successors and assigns, provided, however, no trustee or
                                            --------  -------
other fiduciary appointed with respect to Borrower shall have any rights
hereunder.

           (b)  Lender shall have the unrestricted right at any time or from
time to time, and without Borrower's or any guarantor's consent, to assign all
or any portion of its rights and obligations hereunder to any of its affiliates
(each, an "Assignee"), and Borrower and each guarantor agrees that it shall
           --------
execute, or cause to be executed, such documents, including without limitation,
amendments to this Agreement and to any other documents, instruments and
agreements executed in connection herewith as Lender shall deem necessary to
effect the foregoing. In addition, at the request of Lender and any such
Assignee, Borrower shall issue one or more new promissory notes, as applicable,
to any such Assignee and, if Lender has retained any of its rights and
obligations hereunder following such assignment, to Lender, which new promissory
notes shall be issued in replacement of, but not in discharge of, the liability
evidenced by the promissory note or notes held by Lender prior to such
assignment and shall reflect the amount of the respective commitments and loans
held by such Assignee and Lender after giving effect to such assignment. Upon
the execution and delivery of appropriate assignment documentation, amendments
and any other documentation required by Lender in connection with such
assignment, and the payment by Assignee of the purchase price agreed to by
Lender and such Assignee, such Assignee shall be a party to this Agreement and
shall have all of the rights and obligations of Lender hereunder (and under any
and all other guaranties, documents, instruments and agreements executed in
connection herewith) to the extent that such rights and obligations have been
assigned by Lender pursuant to the assignment documentation between Lender and
such Assignee, and Lender shall be released from its obligations hereunder and
thereunder to a corresponding extent.

           (c)  Lender may transfer any investment securities held by Lender as
Collateral into Lender's name or that of its nominee and may receive the income
and any distributions thereon and hold the same as Collateral for the
Liabilities, or apply the same to any Liability, whether or not a default or an
Event of Default has occurred.

     9.3.  Severability. Any determination that any provision of this Agreement
           ------------
or any application thereof is invalid, illegal, or unenforceable in any respect
in any instance shall not

                                      -20-
<PAGE>

affect the validity, legality, or enforceability of such provision in any other
instance, or the validity, legality, or enforceability of any other provision of
this Agreement.

     9.4.  Amendments; Course of Dealing.  This Agreement and the other Loan
           -----------------------------
Documents incorporate all discussions and negotiations between Borrower and
Lender, either express or implied, concerning the matters included herein and in
such other instruments, any custom, usage, or course of dealings to the contrary
notwithstanding.  No such discussions, negotiations, custom, usage, or course of
dealings shall limit, modify, or otherwise affect the provisions thereof.  No
failure by Lender to give noticed to Borrower of Borrower's having failed to
observe and comply with any warranty or covenant included in any Loan Document
shall constitute a waiver of such warranty or covenant or the amendment of the
subject Loan Document.  This Agreement may be amended only with the written
consent of all parties hereto.

     9.5.  Power of Attorney. In connection with all powers of attorney included
           -----------------
in this Agreement, Borrower hereby grants unto Lender full power to do any and
all things necessary or appropriate in connection with the exercise of such
powers as fully and effectually as Borrower might or could do, hereby ratifying
all that said attorney shall do or cause to be done by virtue of this Agreement.
No power of attorney set forth in this Agreement shall be affected by any
disability or incapacity suffered by Borrower and each shall survive the same.
All powers conferred upon Lender by this Agreement, being coupled with an
interest, shall be irrevocable until this Agreement is terminated.

     9.6.  Lender's Costs and Expenses. Borrower shall pay on demand all Costs
           ---------------------------
of Collection and all reasonable expenses of Lender in connection with the
preparation, execution, and delivery of this Agreement, and any and all
documents, instruments and agreements delivered to Lender in connection
herewith, whether evidencing the Liabilities, or granting Lender certain rights
with respect to Borrower, or its shares of stock, and of any Loan Documents,
whether now existing or hereafter arising, and all other reasonable expenses
which may be incurred by Lender in preparing or amending this Agreement and all
other agreements, instruments, and documents related thereto, or otherwise
incurred with respect to the Liabilities. Borrower specifically authorizes
Lender to pay all such fees and expenses.

     9.7.  Copies and Facsimiles.  This Agreement and all documents which relate
           ---------------------
thereto, which have been or may be hereinafter furnished Lender may be
reproduced by Lender by any photographic, microfilm, xerographic, digital
imaging, or other process, and Lender may destroy any document so reproduced.
Any such reproduction shall be admissible in evidence as the original itself in
any judicial or administrative proceeding (whether or not the original is in
existence and whether or not such reproduction was made in the regular course of
business).

     9.8.  Governing Law. This Agreement and all rights and obligations
           -------------
hereunder, including matters of construction, validity, and performance, shall
be governed by the laws of the State of Illinois.

     9.9.  Consent to Jurisdiction. Borrower agrees that any legal action,
           -----------------------
proceeding, case, or controversy against Borrower with respect to any Loan
Document may be brought in the City of Norfolk in the Commonwealth of Virginia,
as Lender may elect in Lender's sole discretion.  By execution and delivery of
this Agreement, Borrower, for itself and in respect of its property,

                                      -21-
<PAGE>

accepts, submits, and consents generally and unconditionally, to the
jurisdiction of the aforesaid courts.

     9.10.  Indemnification. Borrower shall indemnify, defend, and hold Lender
            ---------------
and any employee, officer, or agent of Lender (each, an "Indemnified Person")
                                                         ------------------
harmless of and from any claim brought or threatened against any Indemnified
Person by Borrower, any guarantor or endorser of the Liabilities, or any other
Person (as well as from attorneys' reasonable fees and expenses in connection
therewith) on account of Lender's relationship with Borrower or any other
guarantor or endorser of the Liabilities (each of which may be defended,
compromised, settled, or pursued by the Indemnified Person with counsel of
Lender's selection, but at the expense of Borrower) other than any claim as to
which a final determination is made in a judicial proceeding (in which Lender
and any other Indemnified Person has had an opportunity to be heard), which
determination includes a specific finding that the Indemnified Person seeking
indemnification had acted in a grossly negligent manner or in actual bad faith.
The within indemnification shall survive payment of the Liabilities and/or any
termination, release, or discharge executed by Lender in favor of Borrower.

     9.11.  Agreement Controlling.  The Loan Documents shall be construed and
            ---------------------
interpreted in a harmonious manner, provided, however, that in the event of any
inconsistency between the provisions of this Agreement and any other Loan
Document, the provisions of this Agreement shall govern and control.

     9.12.  Right of Set-Off. Borrower and any guarantor hereby grant to Lender
            ----------------
a lien, security interest and right of setoff as security for all Liabilities
and obligations to Lender, whether now existing or hereafter arising upon and
against all deposits, credits, collateral and property, now or hereafter in the
possession, custody, safekeeping or control of Lender or any entity under the
control of Lender, or in transit to any of them. At any time without demand or
notice, Lender or any entity under control of Lender may set off the same or any
part thereof and apply the same to any liability or obligation of Borrower and
any guarantor even though unmatured and regardless of the adequacy of any other
collateral securing the loan. ANY AND ALL RIGHTS TO REQUIRE LENDER TO EXERCISE
ITS RIGHTS OR REMEDIES WITH RESPECT TO ANY OTHER COLLATERAL WHICH SECURES THE
LOAN, PRIOR TO EXERCISING ITS RIGHT OF SETOFF WITH RESPECT TO SUCH DEPOSITS,
CREDITS OR OTHER PROPERTY OF BORROWER OR ANY GUARANTOR, ARE HEREBY KNOWINGLY,
VOLUNTARILY AND IRREVOCABLY WAIVED.

     9.13.  Waivers.
          -------

          (a)  Borrower (and all guarantors, endorsers, and sureties of the
Liabilities) make each of the waivers included in Section 9.13(b), below,
knowingly, voluntarily, and intentionally, and understands that Lender, in
entering into the financial arrangements contemplated hereby and in providing
loans and other financial accommodations to or for the account of Borrower as
provided herein, whether now or in the future, is relying on such waivers.

                                      -22-
<PAGE>

           (b) BORROWER, AND EACH SUCH GUARANTOR, ENDORSER, AND SURETY
RESPECTIVELY KNOWINGLY, VOLUNTARILY AND INTENTIONALLY WAIVES THE FOLLOWING:
                                                      ------

               (i)    Except as otherwise specifically required hereby, notice
     of non-payment, demand, presentment, protest and all forms of demand and
     notice, both with respect to the Liabilities;

               (ii)   Except as otherwise specifically required hereby, the
     right to notice and/or hearing prior to Lender's exercising of Lender's
     rights upon default; and

               (iii)  THE RIGHT TO A JURY IN ANY TRIAL OF ANY CASE OR
     CONTROVERSY IN WHICH LENDER IS OR BECOMES A PARTY (WHETHER SUCH CASE OR
     CONTROVERSY IS INITIATED BY OR AGAINST LENDER OR IN WHICH LENDER IS JOINED
     AS A PARTY LITIGANT), WHICH CASE OR CONTROVERSY ARISES OUT OF OR IS IN
     RESPECT OF, ANY RELATIONSHIP AMONGST OR BETWEEN BORROWER OR ANY OTHER
     PERSON AND LENDER (AND LENDER LIKEWISE WAIVES THE RIGHT TO A JURY IN ANY
     TRIAL OR ANY SUCH CASE OR CONTROVERSY).  THIS WAIVER CONSTITUTES A MATERIAL
     INDUCEMENT FOR LENDER TO ACCEPT THIS AGREEMENT AND MAKE THE LOANS AND
     ADVANCES HEREUNDER.

     9.14. Usury Laws. All agreements between Borrower and any guarantor and
           -----------
Lender are hereby expressly limited so that in no contingency or event
whatsoever, whether by reason of acceleration of maturity of the indebtedness
evidenced hereby or otherwise, shall the amount paid or agreed to be paid to
Lender for the use or the forbearance of the indebtedness evidenced hereby
exceed the maximum permissible under applicable law. As used herein, the term
"applicable law" shall mean the law in effect as of the date hereof provided,
however, that in the event there is a change in the law which results in a
higher permissible rate of interest, then this Agreement shall be governed by
such new law as of its effective date. In this regard, it is expressly agreed
that it is the intent of Borrower and Lender in the execution, delivery and
acceptance of this Agreement to contract in strict compliance with the laws of
the State of Illinois from time to time in effect. If, under or from any
circumstances whatsoever, fulfillment of any provision hereof or of any of the
Loan Documents at the time of performance of such provision shall be due, shall
involve transcending the limit of such validity prescribed by applicable law,
then the obligation to be fulfilled shall automatically be reduced to the limits
of such validity, and if under or from circumstances whatsoever Lender should
ever receive as interest an amount which would exceed the highest lawful rate,
such amount which would be excessive interest shall be applied to the reduction
of the principal balance evidenced hereby and not to the payment of interest.
This provision shall control every other provision of all agreements between
Borrower and any guarantor and Lender.

     9.15. Notices.  All communications under this Agreement shall be in writing
           -------
and shall be delivered by hand or facsimile or mailed by overnight courier or by
registered mail or certified mail, postage prepaid:

                                      -23-
<PAGE>

          (a)  if to Landmark, at Landmark Communications, Inc., 150 W.
Brambleton Avenue, Norfolk, VA 23510 (facsimile: (757) 664-2164), Attention: Guy
R. Friddell, III, Executive Vice President and General Counsel, or at such other
address or facsimile number as Landmark may have furnished the Company in
writing, with a copies to: (i) Willcox & Savage, P.C., 1800 Bank of America
Center, Norfolk, VA 23510 (facsimile: (757) 628-5566), Attention: Thomas C.
Inglima; and (ii) Willkie Farr & Gallagher, 787 Seventh Avenue, New York, NY
10019 (facsimile: (212) 728-8111), Attention: William J. Grant, Jr.; and

            (b)  if to the Company, at 360 N. Michigan Avenue, 19th Floor,
Chicago, IL 60601 (facsimile: (312) 853-0456), Attention: Robert Gorman, or at
such other address or facsimile number as it may have furnished Landmark in
writing, with a copy to Jaiffe, Raitt, Heuer & Weiss, P.C., One Woodward Avenue,
Suite 2400, Detroit, MI 48226 (facsimile: (313) 961-8358), Attention: Peter
Sugar.

            (c)  Any notice so addressed shall be deemed to be given: if
delivered by hand or facsimile, on the date of such delivery; if mailed by
courier, on the first business day following the date of such mailing; and if
mailed by registered or certified mail, on the third business day after the date
of such mailing.

     9.16.  Definitions.  All capitalized terms herein shall have the meaning
            -----------
attributed thereto in EXHIBIT B attached hereto.

     9.17.  Counterparts.  This Agreement may be executed in one or more
            ------------
counterparts, each of which shall be deemed an original and all of which
together shall be considered one and the same agreement.

                 [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK -
                            SIGNATURE PAGE FOLLOWS]

                                      -24-
<PAGE>

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

                              Borrower:

                              coolsavings.com inc.

                              By: /s/ Matthew Moog
                                  -----------------------------------

                              Print Name: Matthew Moog
                                         ----------------------------

                              Title: President
                                    ---------------------------------

                              Lender:

                              Landmark Communications, Inc.

                              By: /s/ Guy R. Friddle, III
                                 ------------------------------------

                              Print Name: Guy R. Friddle, III
                                         ----------------------------

                              Title: Executive Vice President
                                    ---------------------------------

                                      -25-
<PAGE>

                                   EXHIBITS
                                   --------

The following Exhibits to this Loan and Security Agreement are respectively
described in the Section indicated below.  Those schedules for which no
information has been inserted or provided shall be deemed to read "None."

                                      -26-
<PAGE>

                                                                       EXHIBIT A
                                                                       ---------

                              SENIOR SECURED NOTE
                              -------------------

Original Aggregate Principal Amount:  $5,000,000

                                                       Chicago, Illinois
                                                       July 30, 2001

FOR VALUE RECEIVED, the undersigned, coolsavings.com inc., a Michigan
corporation with its principal offices at 360 N. Michigan Avenue, 19th Floor,
Chicago, IL 60601 (the "Borrower"), promises to pay to the order of Landmark
Communications, Inc., a Delaware corporation with an office at 150 W. Brambleton
Avenue, Norfolk, VA 23510 (hereinafter, with any subsequent holder, the
"Lender") at an office of Lender, on the Maturity Date (defined below), without
offset, the principal sum of Five Million and no/100 Dollars ($5,000,000),
adjusted as provided below, together with interest as provided below. This note
(the "Note") evidences the Initial Loan made by Lender to Borrower pursuant to
the Amended and Restated Senior Secured Loan and Security Agreement of even date
(as such may be amended hereafter) (the "Loan Agreement"). As additional
consideration for the Initial Loan, Borrower is issuing to Lender a warrant to
purchase common stock as described in and attached to the Loan Agreement (the
"Initial Warrant"). The payment of this Note is secured by the Loan Agreement
and the collateral described therein. All capitalized terms not defined herein
shall have the meaning ascribed to them in the Loan Agreement. All obligations
under this Note shall be pari passu with the Grid Note, consistent with the Loan
Agreement.

     The outstanding principal amount on this Note shall bear interest at the
rate of twelve percent (12%) per annum and shall commence from the date hereof
and shall continue on the outstanding principal; provided, however, that if the
                                                 --------  -------
First Tranche Closing, as such term is defined in the Purchase Agreement, is
consummated, then from and after the date of such closing this Note (including
the outstanding principal and interest that has then accrued) shall bear
interest at the rate of eight percent (8%) per annum. Interest shall be computed
on the actual number of days elapsed on the basis of a year consisting of 360
days. All interest shall accrue and compound quarterly on: October 31, January
31, April 30 and July 31 each year (each such date, a "Quarterly Payment Date").
Such accrued and compounded interest shall be added to the principal amount of
the Note.

     Notwithstanding the foregoing, any amount outstanding under this Note shall
bear interest from and after the Maturity Date at the rate of sixteen (16%) per
annum (the "Default Interest Rate"), increasing monthly by an annual rate which
is one (1) percentage point above the then current Default Interest Rate for
each month that the Note remains overdue. Any interest on this Note accruing
after the Maturity Date shall accrue and be compounded monthly (the date of such
compounding, the "Monthly Compounding Date" and collectively with the Quarterly
Payment Date, the "Compounding Date") until the obligation of Borrower, with
respect to the payment of such interest, has been discharged (whether before or
after judgment).

     Notwithstanding the foregoing, the effective annual rate under the Loan
(including the Default Interest Rate) shall not exceed a maximum annual rate of
twenty-four (24%) percent or the maximum annual rate permitted by law, whichever
is less.

                                       1
<PAGE>

     This Note shall be paid in full on the Maturity Date. Until this Note is
paid in full, on each Compounding Date, in lieu of a cash payment of the
interest due, Borrower shall pay such interest "in-kind". In lieu of delivering
separately documented and certificated promissory notes (the "Note PIK Payment")
and warrants (the "Warrant PIK Payment") for such "in-kind" payments, the Note
PIK Payment shall be effected by adding the accrued interest to the principal
amount of this Note (as described by the compounding set forth above) and the
Warrant PIK Payment shall be effected through the provision in the Initial
Warrant which provides that for every dollar of interest accrued, compounded and
added to the principal amount of this Note, the aggregate number of shares of
Borrower's common stock that may be purchased under the Initial Warrant shall be
increased by two (2) (as such number may be adjusted for dividends, splits,
combinations and the like). The foregoing notwithstanding, no Warrant PIK
Payment shall be required until after the First Tranche Closing and then only in
respect of interest payments accruing thereafter under this Note. Lender
acknowledges that the amount of the Note PIK Payment shall be deemed an
additional loan borrowed from the Lender (it being further acknowledged by the
Borrower that it shall not receive additional funds in connection with any such
loan).

     Borrower may not prepay this Note except as follows: On or after the third
anniversary of the date hereof, the Borrower may prepay the Note if and only if
(a) the Borrower has had earnings and positive cash flow for at least 365
consecutive days in the one year period prior to such payment, (b) the Borrower
has no Indebtedness outstanding other than the Initial Loan, the Grid Note and
trade payables in the ordinary course of business, and (c) the Quick Ratio set
forth in Section 4.12 of the Loan Agreement is 2 to 1 and the Working Capital is
a net positive of $3 million.

     All payments shall be made to Lender at its address specified above, or at
such other address as Lender may specify in writing to Borrower. All payments
received from Borrower hereunder shall be applied first, to the payment of any
expenses due to Lender pursuant to the terms of the Loan Agreement, second, to
the payment of interest accrued and unpaid on the Note, and third, to reduce the
principal balance hereunder. Any payments of expenses, principal or interest
shall be made in lawful money of the United States of America.

     The Borrower shall pay all outstanding principal and unpaid accrued
interest on the Note in full on January 26, 2002 (the "Maturity Date");
provided, however, that, if the transactions contemplated under the Purchase
--------  -------
Agreement are consummated, the Maturity Date shall be June 30, 2006.
Notwithstanding the foregoing if any amount under the Note is not paid in full
when due, whether at maturity, by acceleration or otherwise (the "Default
Date"), the Maturity Date shall be the Default Date.

     Within ten (10) days of each Compounding Date, or as reasonably requested
by the Holder, the Company shall issue to the Holder a certificate executed by
the Company's chief financial officer or other executive officer setting forth
the aggregate outstanding principal amount of the Note as of such date and the
amount of the interest accrued, compounded and added to the Initial Loan.

     This Note is secured by the Collateral defined and described in the Loan
Agreement.  In addition, any and all deposits or other sums at any time credited
by or due to Borrower from

                                       2
<PAGE>

Lender or any of its banking or lending affiliates or any bank acting as a
participant under any loan arrangement between Lender of Borrower, and any cash,
securities, instruments, or other property of Borrower in the possession of
Lender, or any of its banking or lending affiliates, and any bank acting as a
participant under any loan arrangement between Lender and Borrower, whether for
safekeeping, or otherwise, or in transit to or from Lender or any of its banking
or lending affiliates or any such participant, or in the possession of any third
party acting on Lender's behalf (regardless of the reason Lender had received
same or whether Lender has conditionally released the same) shall at all times
constitute security for any and all Liabilities, and may be applied or set off
against such Liabilities at any time, whether or not the Liabilities are then
due or whether or not other collateral is available to Lender.

     Any Event of Default under the Loan Agreement shall constitute an event of
default under this Note. Upon an event of default, the entire principal amount
then outstanding, and all accrued and unpaid interest, and all other sums
required under this Note and the Loan Agreement shall, notwithstanding the
stated maturity in this Note, become immediately due and payable, without notice
or demand to Borrower. Upon default, Lender shall have the right, immediately
and without notice to Borrower or the taking of any other action, to set-off
against this Note, all liabilities of Lender to Borrower and all obligations for
money or money's worth owed by Lender to Borrower, whether or not due, without
notice to Borrower (such liabilities and obligations including, without
limitation, all money, stocks, bonds or other security or property of any kind
or nature held by or in the possession of Lender to or for the credit of
Borrower); and Lender shall be deemed to have made a charge against any such
liabilities or obligations immediately upon the occurrence of any event of
default under this Note even though such charge is subsequently made or entered
on the behalf of Lender. The remedies provided in this Note upon default and in
other agreement between Lender and Borrower are cumulative and not exclusive of
any other remedies provided under the Loan Agreement or at law or in equity.

     No delay or omission by Lender in exercising or enforcing any of Lender's
powers, rights, privileges, remedies, or discretions hereunder shall operate as
a waiver thereof on that occasion nor on any other occasion.  No waiver of any
default hereunder shall operate as a waiver of any other default hereunder, nor
as a continuing waiver.

     Borrower, and each endorser and guarantor, if any, of this Note, shall
indemnify, defend, and hold Lender harmless against any claim brought or
threatened against Lender by Borrower (other than a claim which is finally
judicially determined against Lender), by any endorser or guarantor, or by any
other person (as well as from attorneys' reasonable fees and expenses in
connection therewith) on account of Lender's relationship with Borrower or any
endorser or guarantor hereof (each of which may be defended, compromised,
settled or pursued by Lender with counsel of Lender's selection, but at the
expense of Borrower and any endorser and/or guarantor).

     Borrower will pay on demand all attorneys' reasonable fees and out-of-
pocket expenses incurred by Lender in the administration of all Liabilities and
obligations of Borrower to Lender, including, without limitation, costs and
expenses associated with travel on behalf of Lender. Borrower will also pay on
demand, without limitation, all attorneys' reasonable fees, out-of-pocket
expenses incurred by Lender's attorneys and all costs incurred by Lender,
including, without limitation, costs and expenses associated with travel on
behalf of Lender, which costs

                                       3
<PAGE>

and expenses are directly or indirectly related to the protection or enforcement
of any of Lender's rights against Borrower or any such endorser or guarantor and
against any collateral given Lender to secure this Note or any other Liabilities
of Borrower or such endorser and guarantor to Lender (whether or not suit is
instituted by or against Lender).

     Borrower, and each endorser and guarantor of this Note, respectively waives
presentment, demand, notice, and protest, and also waives any delay on the part
of the holder hereof. Each assents to any extension or other indulgence
(including, without limitation, the release or substitution of collateral)
permitted Borrower or any endorser or guarantor by Lender with respect to this
Note and/or any collateral given to secure this note or any extension or other
indulgence, as described above, with respect to any other liability or any
collateral given to secure any other liability of Borrower or any endorser or
guarantor to Lender.

     This Note shall be binding upon Borrower and each endorser and guarantor
hereof and upon their respective heirs, successors, assigns, and
representatives, and shall inure to the benefit of Lender and its successors,
endorsees, and assigns.

     The liabilities of Borrower and any endorser or guarantor of this Note are
joint and several; provided, however, that the release by Lender of Borrower or
any one or more endorser or guarantor shall not release any other person
obligated on account of this Note. Each reference in this Note to Borrower, any
endorser, and any guarantor, is to such person individually and also to all such
persons jointly. No person obligated on account of this Note may seek
contribution from any other person also obligated unless and until all
liabilities, obligations and indebtedness to Lender of the person from whom
contribution is sought have been satisfied in full.

     Borrower and each endorser and guarantor hereof each authorizes Lender to
complete this Note if delivered incomplete in any respect.

     This Note is delivered to Lender at its offices at 150 W. Brambleton
Avenue, Norfolk, VA  23510, shall be governed by the laws of the State of
Illinois, and shall take effect as a sealed instrument. Borrower and each
endorser and guarantor of this Note each submits to the jurisdiction of the
courts of the State of Illinois for all purposes with respect to this Note, any
collateral given to secure their respective liabilities, obligations and
indebtedness to Lender, and their respective relationships with Lender.  Any
determination that any provision of this Note or any application thereof is
invalid, illegal, or unenforceable in any respect in any instance shall not
affect the validity, legality or enforceability of such provision in any other
instance, or the validity, legality or enforceability of any other provision of
this Note.

     The undersigned makes the following waiver knowingly, voluntarily, and
intentionally, and understands that Lender, in the establishment and maintenance
of Lender's relationship with Borrower contemplated by the within Note, is
relying thereon.  THE UNDERSIGNED, TO THE EXTENT ENTITLED THERETO, WAIVES ANY
                                                                   ------
PRESENT OR FUTURE RIGHT OF THE UNDERSIGNED, OR OF ANY GUARANTOR OR ENDORSER OF
THE UNDERSIGNED OR OF ANY OTHER PERSON LIABLE TO LENDER ON ACCOUNT OF OR IN
RESPECT TO THE LIABILITIES, TO A TRIAL BY JURY IN ANY CASE OR CONTROVERSY IN
WHICH LENDER IS OR BECOMES A PARTY (WHETHER SUCH CASE OR CONTROVERSY IS
INITIATED BY OR AGAINST LENDER OR IN WHICH LENDER IS

                                       4
<PAGE>

JOINED AS A PARTY LITIGANT), WHICH CASE OR CONTROVERSY ARISES OUT OF, OR IS IN
RESPECT TO, ANY RELATIONSHIP AMONGST OR BETWEEN THE UNDERSIGNED, ANY SUCH
PERSON, AND LENDER.

     Borrower has read all of the terms and conditions of this Note and
acknowledges receipt of an exact copy of it.

WITNESS                                    coolsavings.com inc.
Signed in my Presence

/s/ John J. Adams                          By: /s/ Matthew Moog
---------------------------------------       ----------------------------------
Print Name: John J. Adams                  Name: /s/ Matthew Moog
                                                --------------------------------
                                           Title: President
                                                 -------------------------------

                                       5
<PAGE>

                                                                       EXHIBIT B
                                                                       ---------

                                  DEFINITIONS
                                  -----------

     As herein used, the following terms have the following meanings or are
defined in the section of the within Agreement so indicated:

     "Account Debtor": has the meaning given that term in the UCC (as defined
          below).

     "Accounts" and "Accounts Receivable" include, without limitation,
          "accounts" as defined in the UCC, and also all: accounts, accounts
          receivable, credit card receivables, notes, drafts, acceptances, and
          other forms of obligations and receivables and rights to payment for
          credit extended and for goods sold or leased, or services rendered,
          whether or not yet earned by performance.

     "Advance": has the meaning set forth in Section 1.1(a).

     "Affiliate": means, with respect to any two Persons, a relationship in
          which (a) one holds, directly or indirectly, not less than Twenty Five
          Percent (25%) of the capital stock, beneficial interests, partnership
          interest, or other equity interests of the other; or (b) one has,
          directly or indirectly, Control of the other; or (c) not less than
          Twenty Five Percent (25%) of their respective ownership is directly or
          indirectly held by the same third Person.

     "Agreement": is defined in the Preamble.

     "ANB": is defined in Section 2.1(o).

     "ANB Forbearance Agreement": is defined in Section 2.1(o).

     "Assignee": is defined in Section 9.2(b).

     "Balance Sheet": has the meaning given such term under the Purchase
          Agreement.

     "Bankruptcy Code": Title 11, U.S.C., as amended from time to time.

     "Borrower": is defined in the Preamble.

     "Business Day": any day other than (a) a Saturday, Sunday; or (b) a day
          which shall be in the State of New York a legal holiday or day on
          which banking institutions are required or authorized to close.

     "Capital Lease": any lease which may be capitalized in accordance with
          GAAP.

     "Change of Control": shall mean (i) the sale, lease or transfer of all or
          substantially all of the assets of the Company to any "Person" or
          "group" (within the meaning of Sections 13(d)(3) and 14(d)(2) of the
          Exchange Act, or any successor provision to either of the foregoing,
          including any group acting for the purpose of acquiring, holding or
          disposing of securities within the meaning of Rule 13d-5(b)(1) under
          the Exchange Act), (ii) the approval by the requisite stockholders of
          the Company of a plan of liquidation or dissolution of the Company,
          (iii) any "Person" or "group" (within the meaning of Sections 13(d)
          and 14(d)(2) of the Exchange Act, or any successor provision to either
          of the foregoing, including any group acting for the purpose of
          acquiring, holding or disposing of securities within the meaning

                                       1
<PAGE>

          of Rule 13d- 5(b)(1) under the Exchange Act) becomes the "beneficial
          owner" (as defined in Rule 13d-3 under the Exchange Act) of more than
          50% of the total voting power of all classes of the voting stock of
          the Company and/or warrants or options to acquire such voting stock,
          calculated on a fully diluted basis, unless, as a result of such
          transaction, the ultimate direct or indirect ownership of the Company
          is substantially the same immediately after such transaction as it was
          immediately prior to such transaction, or (iv) any consolidation or
          merger of the Company pursuant to which the Company Common Stock would
          be converted into cash, securities or other property, in each case
          other than a consolidation or merger of the Company in which the
          holders of Company Common Stock and other capital stock of the Company
          entitled to vote in the election of directors of the Company,
          immediately prior to the consolidation or merger have, directly or
          indirectly, at least a majority of the total voting power in the
          aggregate of capital stock entitled to vote in the election of
          directors of the continuing or surviving corporation immediately after
          the consolidation or merger. Notwithstanding the foregoing, the
          transactions contemplated by the Purchase Agreement shall not
          constitute a Change of Control.

     "Charter": shall mean the Articles of Incorporation of the Borrower, as
          amended or the Certificate of Incorporation of the Borrower's wholly
          owned subsidiary, Newco, after the consummation of the Merger (as such
          term is defined in the Purchase Agreement).

     "Chattel Paper": has the meaning given that term in the UCC.

     "Collateral": is defined in Section 2.1.

     "Compounding Date": is defined in Section 1.2(b).

     "Conservative Forecast": is defined in Section 4.12(a).

     "Contingent Obligation": shall mean, as applied to any Person, any direct
          or indirect liability, contingent or otherwise, of that Person with
          respect to (i) any indebtedness, lease, dividend, letter of credit or
          other obligation of another, including, without limitation, any such
          obligation directly or indirectly guaranteed, endorsed, co-made or
          discounted or sold with recourse by that Person, or in respect of
          which that Person is otherwise directly or indirectly liable; (ii) any
          obligations with respect to undrawn letters of credit issued for the
          account of that Person; and (iii) all obligations arising under any
          interest rate, currency or commodity swap agreement, interest rate cap
          agreement, interest rate collar agreement, or other agreement or
          arrangement designated to protect a Person against fluctuation in
          interest rates, currency exchange rates or commodity prices; provided,
          however, that the term "Contingent Obligation" shall not include
          endorsements for collection or deposit in the ordinary course of
          business. The amount of any Contingent Obligation shall be deemed to
          be an amount equal to the stated or determined amount of the primary
          obligation in respect of which such Contingent Obligation is made or,
          if not stated or determinable, the maximum reasonably anticipated
          liability in respect thereof as determined by such Person in good
          faith; provided, however, that such amount shall not in any event

                                       2
<PAGE>

          exceed the maximum amount of the obligations under the guarantee or
          other support arrangement.

     "Contract Rights": includes, without limitation, "contract rights" as now
          or formerly defined in the UCC and also any right to payment under a
          contract not yet earned by performance and not evidenced by an
          instrument or Chattel Paper.

     "Control": Person(s) shall be deemed to Control another Person if such
          Person(s) directly or indirectly possess the power to direct or cause
          the direction of the management and policies of such other Person,
          whether through ownership of voting securities, by contract, or
          otherwise.

     "Cost Threshold": is defined in Section 4.12(a)(ii).

     "Costs of Collection" includes, without limitation, all attorneys'
          reasonable fees and reasonable out-of-pocket expenses incurred by
          Lender's attorneys, and all reasonable costs incurred by Lender in the
          administration of the Liabilities and/or the Loan Documents,
          including, without limitation, reasonable costs and expenses
          associated with travel on behalf of Lender, which costs and expenses
          are directly or indirectly related to or in respect of Lender's:
          administration and management of the Liabilities; negotiation,
          documentation, and amendment of any Loan Document; or efforts to
          preserve, protect, collect, or enforce the Collateral, the
          Liabilities, and/or Lender's Rights and Remedies and/or any of
          Lender's rights and remedies against or in respect of any guarantor or
          other person liable in respect to the Liabilities (whether or not suit
          is instituted in connection with such efforts). The Costs of
          Collection are Liabilities, and at Lender's option may bear interest
          at the highest post-default rate which Lender may charge Borrower
          hereunder as if such had been lent, advanced, and credited by Lender
          to, or for the benefit of, Borrower.

     "Current Assets":  shall mean, as of any applicable date, all amounts that
          should, in accordance with GAAP, be included as current assets on the
          consolidated balance sheet of Borrower and its Subsidiaries as at such
          date less all inventory and non-recurring items including without
          limitation tax credits.

     "Current Liabilities": means, as of any applicable date, all amounts that
          should, in accordance with GAAP, be included as current liabilities on
          the consolidated balance sheet of Borrower and its Subsidiaries, as at
          such date, plus, to the extent not already included therein, all
          Advances made under this Agreement or by Lender for Borrower's benefit
          under the Forbearance Agreements, including all Indebtedness that is
          payable upon demand or within one year from the date of determination
          thereof unless such Indebtedness is renewable or extendable at the
          option of Borrower or any Subsidiary to a date more than one year from
          the date of determination, including all current maturities of long
          term debt.

     "Default Date": is defined in Section 1.4.

     "Default Interest Rate": is defined in Section 1.2(b).

     "Demand Interest Rate": is defined in Section 1.3(b).

     "Documents": has the meaning given that term in the UCC.

                                       3
<PAGE>

     "Documents of Title": has the meaning given that term in the UCC.

     "Earned Cash Billings": means, with respect to an applicable monthly or
          quarterly measurement pursuant to Section 4.12(a), the sum of:

          (i) the aggregate amount of all of Borrower's billed and unpaid
               invoices to Eligible Debtors for services rendered during the
               month or quarter;

          minus (ii) the aggregate amount of all credit memos and other negative
          -----
               adjustments with respect to such period;

          minus (iii) the aggregate amount of all advanced billings (e.g.,
          -----
               unearned revenue) included in such invoices;

          plus (iv) all deferred revenue from prior periods that is earned in
          ----
               the period being measured (to the extent not included in (i)
               above);

          plus (v) all royalties earned from Eligible Debtors (to the extent not
          ----
               included in (i) above);

          minus (vi) all amounts relating to barter; and
          -----

          minus (vii) all positive adjustments and invoices relating to prior
          -----
               periods.

     "EBITDA": means earnings before income taxes, depreciation and
          amortization.

     "Eligible Debtors": means those invoiced customers of Borrower that as of
          the applicable measurement date are not indebted to Borrower with
          respect to an account receivable that is more than ninety (90) days
          past due, are not subject to any pending or threatened bankruptcy or
          insolvency proceeding, are not subject to any event or circumstance
          that gives Borrower reason to believe that the collectability of their
          account may be impaired, and have not asserted a claim against
          Borrower or disputed any amount that is then due and owing.

     "Encumbrance": each of the following:

               (a)    security interest, mortgage, pledge, hypothecation, lien,
          attachment, or charge of any kind (including any agreement to give any
          of the foregoing); conditional sale or other title retention
          agreement; sale of accounts receivable or chattel paper; or other
          arrangement pursuant to which any Person is entitled to any preference
          or priority with respect to the property or assets of another Person
          or the income or profits of such other Person or which constitutes an
          interest in property to secure an obligation; each of the foregoing
          whether consensual or non-consensual and whether arising by way of
          agreement, operation of law, legal process or otherwise.

                                       4
<PAGE>

               (b)    The filing of any financing statement under the UCC or
          comparable law of any jurisdiction.

     "Equipment" includes, without limitation, "equipment" as defined in the
          UCC, and also all motor vehicles, rolling stock, machinery, office
          equipment, plant equipment, tools, dies, molds, store fixtures,
          furniture, and other goods, property, and assets which are used and/or
          were purchased for use in the operation or furtherance of Borrower's
          business, and any and all accessions, additions thereto, and
          substitutions therefore.

     "Events of Default": is defined in Article 6.

     "Exchange Act": is the Securities Exchange Act of 1934, as amended, and the
          rules and regulations promulgated thereunder.

     "Fixtures": has the meaning given that term in the UCC.

     "Forbearance Agreements": is defined in Section 5.8.

     "GAAP" or "Generally Accepted Accounting Principles": principles which are
          consistent with those promulgated or adopted by the Financial
          Accounting Standards Board and its predecessors (or successors) in
          effect and applicable to that accounting period in respect of which
          reference to GAAP or Generally Accepted Accounting Principles is being
          made.

     "General Intangibles" includes, without limitation, "general intangibles"
          as defined in the UCC; and also all: rights to payment for credit
          extended; deposits; amounts due to Borrower; credit memoranda in favor
          of Borrower; warranty claims; tax refunds and abatements; insurance
          refunds and premium rebates; all means and vehicles of investment or
          hedging, including, without limitation, options, warrants, and futures
          contracts; records; customer lists; telephone numbers; goodwill;
          causes of action; judgments; payments under any settlement or other
          agreement; literary rights; rights to performance; royalties; license
          and/or franchise fees; rights of admission; licenses; franchises;
          license agreements, including all rights of Borrower to enforce same;
          permits, certificates of convenience and necessity, and similar rights
          granted by any governmental authority; patents, patent applications,
          patents pending, and other intellectual property; developmental ideas
          and concepts; proprietary processes; blueprints, drawings, designs,
          diagrams, plans, reports, and charts; catalogs; manuals; technical
          data; computer software programs (including the source and object
          codes therefor), computer records, computer software, rights of access
          to computer record service bureaus, service bureau computer contracts,
          and computer data; tapes, disks, semi-conductors chips and printouts;
          trade secrets rights, copyrights, mask work rights and interests, and
          derivative works and interests; user, technical reference, and other
          manuals and materials; trade names, trademarks, service marks, and all
          goodwill relating thereto; applications for registration of the
          foregoing; and all other general intangible property of Borrower in
          the nature of intellectual property; proposals; cost estimates, and
          reproductions on paper, or otherwise, of any and all concepts or
          ideas, and any matter related to, or connected with, the design,
          development, manufacture, sale, marketing,

                                       5
<PAGE>

          leasing, or use of any or all property produced, sold, or leased, by
          Borrower or credit extended or services performed, by Borrower,
          whether intended for an individual customer or the general business of
          Borrower, or used or useful in connection with research by Borrower.

     "Goods": has the meaning given that term in the UCC.

     "Grid Note": is defined in Section 1.1(a).

     "Indebtedness": all indebtedness and obligations (including without
          limitation any Contingent Obligations) of or assumed by any Person
          including, without limitation, any indebtedness or obligation: (i) in
          respect of money borrowed (including any indebtedness which is non-
          recourse to the credit of such Person but which is secured by an
          Encumbrance on any asset of such Person) or evidenced by a promissory
          note, bond, debenture or other written obligation to pay money; (ii)
          for the payment, deferred or other written obligation to pay money;
          (ii) for the payment, deferred for more than Thirty (30) days, of the
          purchase price of goods or services (other than current trade
          liabilities of such Person incurred in the ordinary course of business
          and payable in accordance with customary practices); (iii) in
          connection with any letters of credit or acceptance transaction
          (including, without limitation, the face amount of all letters of
          credit and acceptances issued for the account of such Person or
          reimbursement on account of which such Person would be obligated);
          (iv) in connection with the sale or discount of accounts receivable or
          chattel paper of Borrower; (v) on account of deposits or advances; and
          (vi) as lessee under Capital Leases. "Indebtedness" of any Person
          shall also include: (x) Indebtedness of others secured by an
          Encumbrance on any asset of such Person; (y) Any guaranty,
          endorsement, suretyship or other undertaking pursuant to which that
          Person may be liable on account of any obligation of any third party;
          and (z) the Indebtedness of a partnership or joint venture in which
          such Person is a general partner or joint venturer.

     "Indemnified Person": is defined in Section 9.10.

     "Initial Loan": is defined in Section 1.1(a).

     "Initial Warrants": is defined in Section 1.1(b).

     "Instruments": has the meaning given that term in the UCC.

     "Inventory" includes, without limitation, "inventory" as defined in the UCC
          and also all: packaging, advertising, and shipping materials related
          to any of the foregoing, and all names or marks affixed or to be
          affixed thereto for identifying or selling the same; Goods held for
          sale or lease or furnished or to be furnished under a contract or
          contracts of sale or service by Borrower, or used or consumed or to be
          used or consumed in Borrower's business; Goods of said description in
          transit: returned, repossessed and rejected Goods of said description;
          and all documents (whether or not negotiable) which represent any of
          the foregoing.

     "Investment Property": has the meaning given that term in the UCC.

     "Lender": is defined in Preamble.

     "Lender's Rights and Remedies": is defined in Section 7.7.

                                       6
<PAGE>

     "Liability" or "Liabilities" includes, without limitation, all and each of
          the following, whether now existing or hereafter arising:

               (a)     Any and all direct and indirect liabilities, debts, and
          obligations of Borrower to Lender, each of every kind, nature, and
          description.

               (b)     Each obligation to repay any loan, advance, indebtedness,
          note, obligation, overdraft, or amount now or hereafter owing by
          Borrower to Lender (including all future advances whether or not made
          pursuant to a commitment by Lender), whether or not any of such are
          liquidated, unliquidated, primary, secondary, secured, unsecured,
          direct, indirect, absolute, contingent, or of any other type, nature,
          or description, or by reason of any cause of action which Lender may
          hold against Borrower.

               (c)     All notes and other obligations of Borrower now or
          hereafter assigned to or held by Lender, each of every kind, nature,
          and description including, without limitation, the Note and Grid Note.

               (d)     All interest, fees, and charges and other amounts which
          may be charged by Lender to Borrower and/or which may be due from
          Borrower to Lender from time to time.

               (e)     All costs and expenses incurred or paid by Lender in
          respect of any agreement between Borrower and Lender or instruments
          furnished by Borrower to Lender (including, without limitation, Costs
          of Collection, attorneys' reasonable fees, and all court and
          litigation costs and expenses).

               (f)     Any and all covenants of Borrower to or with Lender and
          any and all obligations of Borrower to act or to refrain from acting
          in accordance with any agreement between Borrower and Lender or
          instruments furnished by Borrower to Lender.

     "Lien": any Encumbrance as defined herein.

     "Loan": is defined in Section 1.1(a).

     "Loan Account": the account maintained on Lender's books in which a record
          will be kept of all loans and advances hereunder and payments thereon,
          and all calculations of interest fees or other costs as provided
          hereunder.

     "Loan Documents": this Agreement, the Note, the Grid Note, and each
          instrument and document executed and/or delivered in connection with
          the arrangements contemplated hereby, as each may be amended from time
          to time.

     "Maturity Date": is defined in Section 1.4.

     "Monthly Compounding Date": is defined in Section 1.2(b).

     "Note": is defined in the Preamble.

     "Note PIK Payment": is defined in Section 1.2(d).

                                       7
<PAGE>

     "Original Agreement": is defined in the Preamble.

     "Original Principal Amount": is defined in 1.1(a).

     "Permitted Indebtedness": means:

          (a)  Indebtedness of Borrower in favor of Lender arising under this
               Agreement or any other Loan Document;

          (b)  Indebtedness to ANB and Midwest Guaranty Bank, provided such
               Indebtedness is limited to the Indebtedness described in the
               applicable Forbearance Agreement;

          (c)  Subordinated Debt; and

          (d)  Indebtedness of Borrower under capital leases, provided, the
               aggregate amount financed under all such capital leases
               (including capital leases existing on the date hereof) shall not
               exceed $3 million; and provided, further, Borrower shall not
               incur a capital lease obligation to the extent immediately after
               incurring such obligation Borrower would not be legally permitted
               to declare and pay dividends on its Series B Preferred Stock.

     "Person": any natural person, and any corporation, trust, partnership,
          joint venture, or other enterprise or entity.

     "Proceeds": include, without limitation, "Proceeds" as defined in the UCC,
          and each type of property described in Section 2.1, above.

     "Purchase Agreement":  is defined in Section 1.2(a).

     "Qualified Accounts Receivable": shall mean, as of any applicable date, all
          amounts that should, in accordance with GAAP, be included as an
          account receivable on the consolidated balance sheet of Borrower and
          its Subsidiaries as of such date, but shall specifically exclude any
          receivables that are unbilled (a) more than ninety (90) days past due
          (b) owed by an officer or director (c) owed to an obligor that has any
          accounts receivable with Borrower that are more than ninety (90) days
          past due, or (d) that are disputed or challenged (or for which such
          obligor has otherwise asserted a defense or right of offset with
          respect to collection).

     "Quarterly Payment Dates": is defined in Section 1.2(c).

     "Quick Assets": shall mean, as of any applicable date, the Borrower's
          consolidated cash, cash equivalents, investments with maturities of
          fewer than ninety (90) days determined in accordance with GAAP, and
          Qualified Accounts Receivable, but shall exclude all restricted and
          regulated cash.

     "Quick Ratio": shall mean the excess of Quick Assets over Current
          Liabilities.

     "Receivables Collateral": Borrower's Accounts, Accounts Receivable,
          Contract Rights, General Intangibles, Chattel Paper, Instruments,
          Documents of Title, Documents, Securities, letters of credit for the
          benefit of Borrower, and bankers' acceptances held by Borrower, and
          any rights to payment.

     "Related Entity": refers to (a) any Affiliate; and (b) any corporation,
          trust, partnership, joint venture, or other enterprise which: is a
          parent, brother-sister, Subsidiary, or

                                       8
<PAGE>

          Affiliate, of Borrower; could have such enterprise's tax returns or
          financial statements consolidated with Borrower's; could be a member
          of the same controlled Group of corporation (within the meaning of
          Section 1563(a)(1), (2) and (3) of the Internal Revenue Code of 1986,
          as amended from time to time) of which Borrower is a member; Controls
          or is Controlled by Borrower or any Affiliate of Borrower.

     "Securities": has the meaning given that term in the UCC.

     "Securities Act": is the Securities Act of 1933, as amended, and the rules
          and regulations promulgated thereunder.

     "Series B Preferred Stock": has the meaning given such term under the
          Purchase Agreement.

     "Statement Date": has the meaning given such term under the Purchase
          Agreement.

     "Subordinated Debt": means any debt incurred by Borrower that is
          subordinated to the debt owing by Borrower to Lender on terms
          reasonably acceptable to Lender (and identified as being such by
          Borrower and Lender).

     "Subsidiary" means with respect to any Person, corporation, partnership,
          company association, joint venture, or any other business entity of
          which more than fifty percent (50%) of the voting stock or other
          equity interests is owned or controlled, directly or indirectly, by
          such Person or one or more Affiliates of such Person.

     "Tangible Net Worth": shall mean (a) the aggregate amount of all assets of
          Borrower as may be properly classified as such, other than (i) all
          assets of Borrower which are properly classified as intangible assets
          including, without limitation, franchises, licenses, permits, patents,
          patent applications, copyrights, trademarks, trade names, goodwill,
          experimental or organizational expense and other like intangibles,
          including the excess paid for assets acquired over the respective book
          values on the books of the corporation from which acquired, and (ii)
          all investments in and loans to the shareholders, officers, directors,
          employees, subsidiaries and affiliates, less (b) the aggregate amount
          of all Indebtedness and Liabilities of Borrower, all determined in
          accordance with GAAP consistently applied.

     "Total Indebtedness" means all Indebtedness plus all Contingent
          Obligations.

     "Transfer" is defined in Section 5.1.

     "UCC": is Uniform Commercial Code as adopted and in effect in the State of
          Illinois, as amended from time to time.

     "Warrant PIK Payment": is defined in Section 1.2(d).

     "Working Capital" means the excess of Current Assets over Current
          Liabilities.

                                       9

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