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EXHIBIT 10.14

WIRELESS RONIN® TECHNOLOGIES, INC.

CONVERTIBLE DEBENTURE PURCHASE AGREEMENT

JANUARY 5, 2005

SPIRIT LAKE TRIBE

Spirit Lake Tribal Council Office

P.O. Box 359

Main Street

Fort Totten, ND 58335

Ladies and Gentlemen:

     In consideration of the agreement of the Spirit Lake Tribe (the “Purchaser”) to purchase the
$2,000,000 10% fixed rate Convertible Debentures due 2009 as provided for herein, the undersigned
WIRELESS RONIN® TECHNOLOGIES, INC., a Minnesota corporation (the “Company”), hereby agrees with the
Purchaser as follows:

     1. Authorization of Securities. The Company proposes to authorize, issue and sell an
aggregate of $2,000,000 principal amount of its convertible debentures, to be in substantially the
form set forth in Exhibit A to this Agreement (the “Form of Debenture”). The term Debenture as
used herein shall mean the Convertible Debenture attached hereto as Exhibit A and all of the rights
to convert the Debenture.

     The Convertible Debenture is convertible into fully paid and nonassessable shares of Common
Stock of the Company in whole or in part at any time prior to its payment at the option of the
Holder on the terms set forth in the Debenture.

     The Convertible Debenture is convertible in whole at any time prior to its payment at the
option of the Purchaser into fully paid and nonassessable shares of Common Stock of the Company
constituting twenty percent (20%) of all classes of the Common Stock of the Company on a fully
diluted basis, as further explained in paragraph 3(b) of the Convertible Debenture. In addition,
as further explained in paragraph 3(b) of the Convertible Debenture, the Convertible Debenture is
convertible in part at any time prior to its payment at the option of the Purchaser into fully paid
and nonassessable shares of Common Stock of the Company constituting a proportionate percentage of
twenty percent (20%) of all classes of the Common Stock of the Company on a fully diluted basis in
the ratio that the amount of the Convertible Debenture being converted bears to the total amount of
the Convertible Debenture acquired by the Purchaser. Under no circumstances shall paragraph 3(b)
of the Convertible Debenture be read to entitle the Purchaser to shares of Common Stock of the
Company constituting less than 20% of all classes

 

 

of the Common Stock of the Company on a fully diluted basis upon conversion in full of the
Convertible Debenture.

     2. Sale and Purchase of Securities. Subject to the terms and conditions hereof, the
Company agrees to sell to the Purchaser, and the Purchaser agrees to purchase from the Company, the
Convertible Debenture in the aggregate principal amount of $2,000,000.

     3. Closing. The closing of the sale to, and purchase by, the Purchaser of the
Debenture (the “Closing’) shall occur at the offices of the Marshall Group, Inc. at the hour of
                     P.M., Central Standard Time, on January 5, 2005 or on such other day or at such other time or
place as the Purchaser and the Company shall agree upon (the “Closing Date”).

     At the Closing, the Company will deliver to the Purchaser the Debenture being purchased by the
Purchaser, registered in its name, against delivery to the Company of its funds in the amount of
$2,000,000 in payment of the total purchase price of the Debenture being purchased by the
Purchaser.

     4. Restriction on Transfer of Securities.

          4.1 Restrictions. The Debenture is transferable only pursuant to (a) a
public offering registered under the Securities Act of 1933, as amended (the
“Securities Act”), (b) Rule 144 (or any similar rule then in effect) adopted under the
Securities Act, if such rule is available, and (c) subject to the conditions elsewhere
specified in this Section 4, any other legally available means of transfer.

          4.2 (a) Legend. The Debenture shall be endorsed with the following legend:

     THIS CONVERTIBLE DEBENTURE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF
1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. NO SALE OR DISPOSITION MAY
BE EFFECTED EXCEPT IN COMPLIANCE WITH AN EFFECTIVE REGISTRATION STATEMENT RELATED
THERETO OR AN OPINION OF COUNSEL FOR THE HOLDER, SATISFACTORY TO PAYOR, THAT SUCH
REGISTRATION IS NOT REQUIRED UNDER THE ACT.

     Upon the conversion of the Debenture, unless the Company receives an opinion of counsel from
the holder of such a security satisfactory to the Company to the effect that a sale, transfer,
assignment, pledge or distribution of the Conversion Stock issuable upon such conversion may be
made without registration, or unless such Conversion Stock is being disposed of pursuant to
registration under the Securities Act and any applicable state act, the same legend shall be
endorsed on the certificate evidencing such Conversion Stock.

     The aforesaid legend shall be removed with respect to securities held for at least three years
(including, with respect to the Conversion Stock, the period during which the related converted
Debenture had been held) by a person who has not been an affiliate of the Company (as defined in
Rule 144 under the Securities Act) during the three months preceding the request

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for removal of
such legend. The foregoing legend removal requirement is based on Rule 144(k)
under the Securities Act as currently in force, and assumes that such Rule (or a successor
thereto) in substantially its current form shall be in effect at the time of any such request for
legend removal.

          (b) Stop Transfer Order. A stop transfer order shall be
placed with the Company’s transfer agent preventing transfer of any of the
securities referred to in paragraph (a) above pending compliance with the
conditions set forth in any such legend (except as otherwise provided in
paragraph (a) above).

          4.3 Removal of Legend. Any legend endorsed on a certificate or instrument
evidencing a security pursuant to Section 4.2 hereof shall be removed, and the Company
shall issue a certificate or instrument without such legend to the holder of such
security, (a) in accordance with Section 4.2(a) hereof, (b) if such security is being
disposed of pursuant to registration under the Securities Act and any applicable state
acts or pursuant to Rule 144 or any similar rule then in effect, or (c) if such holder
provides the Company with an opinion of counsel satisfactory to the Company to the
effect that a sale, transfer, assignment, offer, pledge or distribution for value of
such security may be made without registration and that such legend is not required to
satisfy the applicable exemption from registration.

          4.4 Register of Securities. The Company or its duly appointed agent shall
maintain a separate register for the Debenture in which it shall register the issuance
and transfer of the Debenture. All transfers of the Debenture shall be recorded on the
register maintained by the Company or its agent, and the Company shall be entitled to
regard the registered holder of such securities as the actual owner of the securities
so registered until the Company or its agent is required to record a transfer of such
securities on its register. The Company or its agent shall be required to record any
such transfer when it receives (a) the security to be transferred duly and properly
endorsed by the registered holder thereof or by its attorney duly authorized in
writing, and (b) the opinion of counsel referred to in Sections 4.2 and 4.3 hereof or
evidence of compliance with the registration provisions referred to in those Sections.

     5. Representations and Warranties by Company. Except as disclosed in Exhibit C
hereto, the Company represents and warrants to the Purchaser that:

          5.1 Organization, Standing, etc. The Company is a corporation duly
organized, validly existing and in good standing under the laws of the State of
Minnesota, and has the requisite corporate power and authority to own its properties
and to carry on its business in all material respects as it is now being conducted.
The Company has the requisite corporate power and authority to issue the Debenture and
the Conversion Stock, and to otherwise perform its obligations under this Agreement and
the Debenture. The copies of the Articles of Incorporation and Bylaws (as such Bylaws
were amended on May 28, 2004) of the Company delivered to the Purchaser or their agents
prior to the execution of this Agreement are true and complete copies of the duly and
legally adopted Articles of Incorporation and Bylaws of the Company in effect as of the
date of
this Agreement. The Company does not have any direct or indirect equity interest in
any other firm, corporation, partnership, joint venture association or other
business organization.

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          5.2 Qualification. The Company is duly qualified or licensed as a foreign
corporation in good standing in each jurisdiction wherein the nature of its activities
or of its properties owned or leased makes such qualification or licensing necessary
and failure to be so qualified or licensed would have a material adverse impact on its
business.

          5.3 Financial Statements. Attached hereto as Exhibit B are unaudited
balance sheets at March 31, 2004 and September 30, 2004 (the “Balance Sheet Date”),
together with the related statements of operations, stockholders’ equity and cash flow
for the fiscal year ended March 31, 2004 and the related statements of operations and
stockholders’ equity for the six months ended September 30, 2004, prepared by the
Company. Such financial statements (i) are in accordance with the books and records of
the Company, (ii) present fairly the financial condition of the Company at the balance
sheet dates and the results of its operations for the periods therein specified, and
(iii) have, in all material respects, been prepared in accordance with generally
accepted accounting principles applied on a basis consistent with prior accounting
periods (except, with respect to the interim financial statements, the absence of
footnotes). Specifically, but not by way of limitation, the respective balance sheets
disclose all of the debts, liabilities and obligations of any nature (whether absolute,
accrued or contingent and whether due or to become due) of the Company at March 31,
2004 and September 30, 2004, which, individually or in the aggregate, are material and
which, in accordance with generally accepted accounting principles, would be required
to be disclosed in such balance sheets, and the omission of which would, in the
aggregate, have a material adverse impact on the Company. The balance sheets include
appropriate reserves for all taxes and other liabilities accrued at such date but not
yet payable.

          5.4 Tax Returns and Audits. All required federal, state and local tax
returns or appropriate extension requests of the Company have been filed, and all
federal, state and local taxes required to be paid with respect to such returns have
been paid or due provision for the payment thereof has been made. The Company is not
delinquent in the payment of any such tax or in the payment of any assessment or
governmental charge. The Company has not received notice of any tax deficiency
proposed or assessed against it, and has not executed any waiver of any statute of
limitations on the assessment or collection of any tax. None of the Company’s tax
returns have been audited by governmental authorities. in a manner to bring such
audits to the Company’s attention. The Company does not have any tax liabilities
except those incurred in the ordinary course of business since the Balance Sheet Date.

          5.5 Changes, Dividends, etc. Except for the transactions contemplated by
this Agreement, since the Balance Sheet Date the Company has not: (a) incurred any
debts, obligations or liabilities, absolute, accrued or contingent and whether due
or to become due, except current liabilities incurred in the ordinary course of
business, which (individually or in the aggregate) will not materially and adversely
affect the business, properties or prospects of the Company; (b) paid any obligation
or liability other than, or discharged or satisfied any liens or encumbrances other
than those securing, current liabilities, in each case in the ordinary course of
business; (c) declared or made any payment or distribution to its stockholders as
such, or purchased or redeemed any of its shares of capital stock or other
securities, or obligated itself to do so; (d) mortgaged, pledged or subjected to
lien, charge, security interest or other encumbrance any of its assets, tangible or
intangible, except in the ordinary course of business; (e) sold, transferred or
leased any of its assets except in the ordinary course of business; (f) cancelled or

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compromised any debt or claim, or waived or released any right of material value;
(g) suffered any physical damage, destruction or loss (whether or not covered by
insurance) materially and adversely affecting the properties, business or prospects
of the Company; (h) entered into any transaction other than in the ordinary course
of business; (i) encountered any labor difficulties or labor union organizing
activities; (j) issued or sold any shares of capital stock or other securities or
granted any options, warrants or other purchase rights with respect thereto other
than as contemplated by this Agreement; (k) made any acquisition or disposition of
any material assets or become involved in any other material transaction, other than
for fair value in the ordinary course of business; (l) increased the compensation
payable, or to become payable, to any of its directors or employees, or made any
bonus payment or similar arrangement with any directors or employees or increased
the scope or nature of any fringe benefits provided for its employees or directors;
or (m) agreed to do any of the foregoing other than pursuant hereto. There has been
no material adverse change in the financial condition, operations, results of
operations or business of the Company since the Balance Sheet Date.

          5.6 Title to Properties and Encumbrances. The Company has good and
marketable title to all of its owned properties and assets, and the properties and
assets used in the conduct of its business, except for property disposed of in the
ordinary course of business since the Balance Sheet Date, which properties and assets
are not subject to any mortgage, pledge, lease, lien, charge, security interest,
encumbrance or restriction, except Permitted Liens (as hereinafter defined). The
plant, offices and equipment owned and leased by the Company have been kept in good
condition and repair in the ordinary course of business, and the Company has not been
threatened with any action or proceeding under any building or zoning ordinance, law or
regulation.

          5.7 Litigation; Governmental Proceedings. There are no legal actions,
suits, arbitrations or other legal, administrative or governmental proceedings or
investigations pending or, to the knowledge of the Company, threatened against the
Company, its properties, assets or business, and the Company is not aware of any facts
which are likely to result in or form the basis for any such action, suit or other
proceeding. The Company is not in default with respect to any judgment, order or
decree of any court or any governmental agency or instrumentality. The
Company has not been threatened with any action or proceeding under any business or
zoning ordinance, law or regulation.

          5.8 Compliance with Applicable Laws and Other Instruments. The business
and operations of the Company have been and are being conducted in accordance with all
applicable laws, rules and regulations of all governmental authorities. Neither the
execution nor delivery of, nor the performance of or compliance with, this Agreement or
the Debenture nor the consummation of the transactions contemplated hereby or thereby
will conflict with, or, with or without the giving of notice or passage of time, result
in any breach of, or constitute a default under, or result in the imposition of any
lien or encumbrance upon any asset or property of the Company pursuant to, any
applicable law, administrative regulation or judgment, order or decree of any court or
governmental body, any agreement or other instrument to which the Company is a party or
by which it or any of its properties, assets or rights is bound or affected, and will
not violate the Articles of Incorporation or Bylaws of the Company. The Company is not
in violation of its Articles of Incorporation or its Bylaws nor in violation of, or in
default under, any

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lien, indenture, mortgage, lease, agreement, instrument, commitment
or arrangement in any material respect.

          5.9 Conversion Stock. The shares of Conversion Stock issuable upon
conversion of the Debenture have been reserved for issuance and when issued upon
conversion will be duly authorized, validly issued and outstanding, fully paid,
nonassessable and free and clear of all pledges, liens, encumbrances and restrictions,
except as set forth in Section 4 hereof. The certificates representing the Conversion
Stock to be delivered upon the conversion of the Debenture will be genuine, and the
Company has no knowledge of any fact which would impair the validity thereof.

          5.10 Securities Laws. Based in part upon the representations and warranties
contained in Section 6 hereof, no consent, authorization, approval, permit or order of
or filing with any governmental or regulatory authority is required under current laws
and regulations in connection with the execution and delivery of this Agreement or the
Debenture or the offer, issuance, sale or delivery of the Debenture or the offer of the
Conversion Stock other than the qualification thereof, if required, under applicable
state securities laws, which qualification has been or will be effected as a condition
of these sales. The Company has not, directly or through an agent, offered the
Debenture or the Conversion Stock or any similar securities for sale to, or solicited
any offers to acquire such securities from, persons other than the Purchaser and other
accredited investors. Under the circumstances contemplated hereby, the offer,
issuance, sale and delivery of the Debenture and the offer of the Conversion Stock will
not under current laws and regulations require compliance with the prospectus delivery
or registration requirements of the Securities Act.

          5.11 Patents and Other Intangible Rights. The Company (a) owns or has the
exclusive right to use, free and clear of all material liens, claims and restrictions,
all patents, trademarks, service marks, trade names, copyrights, licenses and rights
with respect to the foregoing, used in the conduct of its business as now conducted,
(b) is not obligated or under any liability whatsoever to make any payments of a
material nature by way of royalties, fees or otherwise to any owner of, licensor of,
or other claimant to, any patent, trademark, trade name, copyright or other
intangible asset, with respect to the use thereof or in connection with the conduct
of its business or otherwise (c) owns or has the unrestricted right to use all trade
secrets, including know-how, inventions, designs, processes, computer programs and
technical data necessary to the development, operation and sale of all products and
services sold or proposed to be sold by it, free and clear of any rights, liens or
claims of others, and (d) is not using any confidential information or trade secrets
of others. The Company is not, nor has it received notice with respect to,
infringing upon or otherwise acting adversely to any known right or claimed right of
any person under or with respect to any patents, trademarks, service marks, trade
names, copyrights, licenses or rights with respect to the foregoing.

          5.12 Capital Stock. The authorized capital stock of the Company consists of
75,000,000 common shares, of which 5,207,007 shares are issued and outstanding and
25,000,000 shares of preferred stock, none of which shares have ever been issued and
outstanding. All of the outstanding shares of capital stock of the Company were duly
authorized and validly issued and are fully paid and nonassessable. There are no
outstanding subscriptions, options, warrants, calls, contracts, demands, commitments,
Convertible Securities (as hereinafter

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defined) or other agreements or arrangements of
any character or nature whatever, except as otherwise disclosed in the Private
Placement Memorandum attached hereto as Exhibit D hereto or as contemplated by this
Agreement, under which the Company is or may be obligated to issue capital stock or
other securities of any kind representing an ownership interest or contingent ownership
interest in the Company. Neither the offer nor the issuance or sale of the Debenture
or the Conversion Stock constitutes an event, under any anti-dilution provisions of any
securities issued or issuable by the Company or any agreements with respect to the
issuance of securities by the Company, which will either increase the number of shares
issuable pursuant to such provisions or decrease the consideration per share to be
received by the Company pursuant to such provisions. No holder of any security of the
Company is entitled to any preemptive or similar rights to purchase securities from the
Company, provided, however, that nothing in this Section 5.12 shall affect, alter or
diminish any right granted to the Purchaser in this Agreement. All outstanding
securities of the Company have been issued in full compliance with an exemption or
exemptions from the registration and prospectus delivery requirements of the Securities
Act and from the registration and qualification requirements of all applicable state
securities laws.

          5.13 Outstanding Debt. The Company has no Indebtedness for Borrowed Money
(as hereinafter defined) except as otherwise set forth in the financial statements
attached hereto as Exhibit B. The Company is not in default in the payment of the
principal of or interest or premium on any such Indebtedness for Borrowed Money, and no
event has occurred or is continuing under the provisions of any instrument, document or
agreement evidencing or relating to any such
Indebtedness for Borrowed Money which with the lapse of time or the giving of
notice, or both, would constitute an event of default thereunder.

          5.14 Schedule of Assets and Contracts. Attached hereto as Exhibit E is a
Schedule of Assets and Contracts containing:

          (a) Annex A: a listing of all real properties owned by the
Company;

          (b) Annex B: a listing of each indenture, lease, sublease, license
or other instrument under which the Company claims or holds a leasehold
interest in real property;

          (c) Annex C: a listing of all written and oral contracts,
agreements, subcontracts, purchase orders, commitments and arrangements
involving payments remaining to or from the Company in excess of Twenty Five
Thousand and 00/100ths Dollars ($25,000.00) and other agreements material to
the Company’s business to which the Company is a party or by which it is bound,
under which full performance (including payment) has not been rendered by any
party thereto;

          (d) Annex D: a listing of all employment agreements, consulting
agreements, noncompetition agreements, executive compensation plans, profit
sharing plans, bonus plans, deferred compensation agreements, employee pension
retirement plans and employee benefit stock option or stock purchase plans and
other employee benefit plans, entered into or adopted by the Company;

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          (e) Annex E: a listing of all deeds of trust, mortgages, security
agreements, pledge agreements and other agreements or arrangements whereby any
of the assets or properties of the Company are subject to any lien,
encumbrance, security interest or charge;

          (f) Annex F: a listing of all leases of personal property
involving payment remaining to or from the Company in excess of Five Thousand
and 00/100ths Dollars ($5,000.00);

          (g) Annex G: a listing of all bank accounts (or accounts with
other financial institutions) maintained by the Company, together with the
persons authorized to make withdrawals from such accounts;

          (h) Annex H: the name of each employee of the Company whose annual
compensation is in excess of Fifty Thousand and 00/100ths Dollars ($50,000.00)
and the remuneration currently payable to each such employee;

          (i) Annex I: the name of each stockholder of the Company and the
number of shares owned by such stockholder;

          (j) Annex J: a listing of all insurance policies in force and
referred to in Section 5.19 hereof; and

          (k) Annex K: a listing of all patents (including applications
therefor), royalty and license agreements, trademarks, trade names, service
marks and copyrights relating to Company products.

     Prior to the Closing Date, the Company shall provide legal counsel for the Purchaser with a
true and complete copy of each document referred to above which such counsel requests to examine.
The Company shall also provide legal counsel for the Purchaser with a true and complete copy of the
Company’s current form of nondisclosure agreement.

     The Company has in all material respects substantially performed all obligations required to
be performed by it to date and is not in default in any material respect under any of the
contracts, agreements, leases, documents, commitments or other arrangements to which it is a party
or by which it is otherwise bound. All instruments referred to above are in effect and enforceable
according to their respective terms (except as the enforceability thereof may be limited by
bankruptcy, insolvency, moratorium, reorganization or similar laws affecting the enforcement of
creditors’ rights generally, and except for judicial limitations on the enforcement of the remedy
of specific performance and other equitable remedies), and there is not under any of such
instruments any existing material default or event of default or event which, with notice or lapse
of time or both, would constitute an event of default thereunder. All parties having material
contractual arrangements with the Company are in substantial compliance therewith and none are in
material default in any respect thereunder. All plans or arrangements listed pursuant to clause
(d) above are fully funded to the extent that such funding is required by generally accepted
accounting principles.

          5.15 Corporate Acts and Proceedings. This Agreement has been duly
authorized by all necessary corporate action on behalf of the Company, and has been
duly

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executed and delivered by authorized officers of the Company. All corporate
action necessary to the authorization, creation, issuance and delivery of the Debenture
and the Conversion Stock has been taken on the part of the Company, or will be taken by
the Company on or prior to the Closing Date. This Agreement is, and the Debenture when
issued pursuant to the terms of this Agreement will be, when executed and delivered
pursuant to the terms of this Agreement, a valid and binding agreement of the Company
enforceable in accordance with its terms, except as the enforceability thereof may be
limited by bankruptcy, insolvency, moratorium, reorganization or other similar laws
affecting the enforcement of creditors’ rights generally, and except for judicial
limitations on the enforcement of the remedy of specific enforcement and other
equitable remedies.

          5.16 Accounts Receivable. To the extent that they exceed the reserves for
doubtful accounts set forth in the financial statements attached hereto as Exhibit B
hereto, the accounts receivable of the Company which are reflected therein and all of
its accounts receivable which have arisen since the Balance Sheet Date (except such
accounts receivable as have been collected since the Balance Sheet Date) are valid and
enforceable claims, and the goods and services sold and delivered which
gave rise to such accounts were sold and delivered in conformity with the applicable
purchase orders, agreements and specifications. Such accounts receivable are
subject to no valid defense or offsets except routine customer complaints or
warranty demands of an immaterial nature. The reserve for doubtful accounts that is
included in Exhibit B hereto is adequate.

          5.17 Inventories. The inventories of the Company which are reflected in
Exhibit B hereto and all inventory items which have been acquired since the Balance
Sheet Date consist of raw materials, supplies, work-in-process and finished goods of
such quality and in such quantities as are currently useable or saleable in the
ordinary course of its business.

          5.18 Purchase Commitments and Outstanding Bids. No purchase commitment of
the Company is in excess of normal, ordinary and usual requirements of its business, or
was made at any price in excess of the then current market price, or contains terms and
conditions more onerous than those usual and customary in the industry. There is no
outstanding material bid, sales proposal, contract or unfilled order of the Company
which (a) will, or could if accepted, require the Company to supply goods or services
at a cost to the Company in excess of the revenues to be received therefrom, or (b)
quotes prices which do not include a mark-up over reasonably estimated costs consistent
with past mark-ups on similar business or market conditions current at the time.

          5.19 Insurance Coverage. There are in full force policies of insurance
issued by insurers of recognized responsibility insuring the Company, its properties
and business against such losses and risks, and in such amounts, as in the Company’s
best judgment, after advice from its insurance broker, are acceptable for the nature
and extent of its business and the Company’s resources.

          5.20 No Brokers or Finders. No person, firm or corporation has or will
have, as a result of any act or omission of the Company, any right, interest or valid
claim against or upon the Company or any Purchaser for any commission, fee or other
compensation as a finder or broker, or in any similar capacity, in connection with the
transactions contemplated by this

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Agreement except for the fees agreed to be paid by
the Company to Marshall Investments Corporation. The Company will indemnify and hold
the Purchaser harmless against any and all liability with respect to any such
commission, fee or other compensation which may be payable or determined to be payable
in connection with the transactions contemplated by this Agreement.

          5.21 Conflicts of Interest. No officer, director or stockholder of the
Company or any affiliate (as such term is defined in Rule 405 under the Securities Act)
of any such person has any direct or indirect interest (a) in any entity which does
business with the Company, or (b) in any property, asset or right which is used by the
Company in the conduct of its business, or (c) in any contractual relationship with the
Company other than as an employee. For the purpose of this Section 5.21, there shall
be disregarded any interest which arises solely from the ownership of less than a 1%
equity interest in a corporation whose stock is
regularly traded on any national securities exchange or in the over-the-counter
market.

          5.22 Licenses. The Company possesses from the appropriate agency,
commission, board and government body and authority, whether state, local or federal,
all licenses, permits, authorizations, approvals, franchises and rights which (a) are
necessary for it to engage in the business currently conducted by it, and (b) if not
possessed by the Company would have an adverse impact on the Company’s business. The
Company has no knowledge that would lead it to believe that it will not be able to
obtain all licenses, permits, authorizations, approvals, franchises and rights that may
be required for any business the Company proposes to conduct.

          5.23 Registration Rights. The Company has not agreed to register any of its
authorized or outstanding securities under the Securities Act.

          5.24 Retirement Plans. The Company does not have any retirement plans in
which any employees of the Company participate that is subject to any provisions of the
Employee Retirement Income Security Act of 1974 and of the regulations adopted pursuant
thereto (“ERISA”).

          5.25 Environmental and Safety Laws. To the best of its knowledge, the
Company is not in violation of any applicable statute, law or regulation relating to
the environment or occupational health and safety, and no material expenditures are or
will be required in order to comply with any such existing statute, law or regulation.

     The operations of the Company do not involve any asbestos, urea-formaldehyde foamed-in-place
insulation, polyclorinated biphenyls (“PCBs”) or any other hazardous substances or materials
including, but not limited to, hazardous substances or materials under the Comprehensive
Environmental Response, Compensation and Liability Act, as amended by the Superfund Amendments and
Reauthorization Act, the Resource Conservation and Recovery Act, the Minnesota Environmental
Response and Liability Act, or any other federal, state or local statute, regulation, code or
ordinance.

          5.26 Employees. To the best of the Company’s knowledge, no officer of the
Company or employee of the Company whose annual compensation is in excess of $50,000.00
has any plans to terminate his or her employment with the Company. The Company has
complied in all material respects with all laws relating to the employment of labor,
including

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provisions relating to wages, hours, equal opportunity, collective bargaining
and payment of Social Security and other taxes, and the Company has not encountered any
material labor difficulties. The Company does not have any worker’s compensation
liabilities, except those reflected in Exhibit B hereto.

          5.27 Absence of Restrictive Agreements. To the best of the Company’s
knowledge, no employee of the Company is subject to any secrecy or non-competition
agreement or any agreement or restriction of any kind that would
impede in any way the ability of such employee to carry out fully all activities of
such employee in furtherance of the business of the Company. To the best of the
Company’s knowledge, no employer or former employer of any employee of the Company
has any claim of any kind whatsoever in respect of any of the rights described in
Section 5.11 hereof.

          5.28 Disclosure. The Company has not knowingly withheld from the Purchaser
any material facts relating to the assets, business, operations, financial condition or
prospects of the Company. No representation or warranty in this Agreement or in any
certificate, schedule, statement or other document furnished or to be furnished to any
Purchaser pursuant hereto or in connection with the transactions contemplated hereby
contains or will contain any untrue statement of a material fact or omits or will omit
to state any material fact required to be stated herein or therein or necessary to make
the statements herein or therein not misleading.

     6. Representations and Warranties of Purchaser. The Purchaser represents and warrants
that:

          6.1 Purchaser. Purchaser is a federally recognized Native American Indian
Tribe.

          6.2 Investment Intent. The Debenture being acquired by the Purchaser
hereunder is being purchased and the Conversion Stock acquired by the Purchaser upon
conversion of such Debentures will be acquired, for such Purchaser’s own account and
not with the view to, or for resale in connection with, any distribution or public
offering thereof within the meaning of the Securities Act. The Purchaser understands
that the Debenture and the Conversion Stock have not been registered under the
Securities Act or any applicable state laws by reason of their issuance or contemplated
issuance in a transaction exempt from the registration and prospectus delivery
requirements of the Securities Act and such laws, and that the reliance of the Company
and others upon this exemption is predicated in part upon this representation and
warranty. The Purchaser further understands that the Debenture and Conversion Stock
may not be transferred or resold without (a) registration under the Securities Act and
any applicable state securities laws, or (b) an exemption from the requirements of the
Securities Act and applicable state securities laws.

     The Purchaser understands that an exemption from such registration is not presently available
pursuant to Rule 144 promulgated under the Securities Act by the Securities and Exchange Commission
(the “Commission”) and that in any event the Purchaser may not sell any securities pursuant to Rule
144 prior to the expiration of a two-year period after the Purchaser has acquired the securities.
The Purchaser understands that any sales pursuant to Rule 144 may only be made in full compliance
with the provisions of Rule 144.

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          6.3 Qualification as Accredited Investor. The Purchaser qualifies as an
accredited investor within the meaning of Rule 501 under the Securities Act. The
Purchaser has such knowledge and experience in financial and business matters that the
Purchaser is capable of evaluating the merits and risks of the investment
to be made hereunder by such Purchaser. The Purchaser has and has had access to all
of the Company’s material books and records and access to the Company’s executive
officers has been provided to the Purchaser or to the Purchaser’s qualified agents.
The state in which the Purchaser’s principal office is located is set forth in the
Purchaser’s address in Section 18(a) of this Agreement. The Purchaser’s principal
office is located within the Spirit Lake Reservation, which is located in the State
of North Dakota.

          6.4 Acts and Proceedings. This Agreement has been duly authorized by all
necessary action on the part of the Purchaser, has been duly executed and delivered by
the Purchaser, and is a valid and binding agreement upon the part of the Purchaser.

          6.5 No Brokers or Finders. No person, firm or corporation has or will
have, as a result of any act or omission by such Purchaser, any right, interest or
valid claim against the Company for any commission, fee or other compensation as a
finder or broker, or in any similar capacity, in connection with the transactions
contemplated by this Agreement. Such Purchaser will indemnify and hold the Company
harmless against any and all liability with respect to any such commission, fee or
other compensation which may be payable or determined to be payable as a result of the
actions of such Purchaser in connection with the transactions contemplated by this
Agreement.

          6.6 Sovereign Immunity. The Spirit Lake Tribe as Purchaser, being an
American Indian Tribe, is possessed with sovereign immunity. The Tribe hereby
proclaims its sovereign immunity, but does agree to a limited waiver of sovereign
immunity pursuant to the terms set forth herein and no expansion thereof. Purchaser
agrees to be subject to suit in United States District Court for the District of North
Dakota for injunctive relief in respect to any claim, crossclaim, or counterclaim
associated with any responsibility set forth herein or associated with its status as
purchaser and/or holder of the Convertible Debentures of the Company. Should the
United States District Court, District of North Dakota not have jurisdiction, then
Purchaser agrees to suit in the North Dakota District Court for the County of Benson.
No waiver of sovereign immunity is made as to Tribal assets beyond those committed for
the purchase of the Convertible Debenture of the Company. Specification of
jurisdiction wherein the Purchaser agrees to be sued as specified above does not limit
the jurisdictions in which Purchaser may initiate suit against the Company, should
Purchaser believe that such legal action may be warranted.

     7. Conditions of the Purchaser’s Obligation. The obligation to purchase and pay for
the Debenture which the Purchaser has agreed to purchase on the Closing Date is subject to the
fulfillment prior to or on the Closing Date of the following conditions.

          7.1 No Errors, etc. The representations and warranties of the Company
under this Agreement shall be true in all material respects as of the Closing Date with
the same effect as though made on and as of the Closing Date.

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          7.2 Compliance with Agreement. The Company shall have performed and
complied with all agreements or conditions required by this Agreement to be performed
and complied with by it prior to or as of the Closing Date.

          7.3 Certificate of Officers. The Company shall have delivered to the
Purchaser a certificate, dated the Closing Date, executed by the President and the
senior financial officer of the Company and certifying to the satisfaction of the
conditions specified in Sections 7.1, 7.2 and 7.5 hereof.

          7.4 Opinion of Company’s Counsel. (a) The Company shall have delivered to
the Purchaser an opinion or opinions of Faegre & Benson, counsel for the Company, dated
the Closing Date, to the effect that:

     (i) The Company is a duly and validly organized and existing corporation in good standing
under the laws of the State of Minnesota; has the corporate power and authority to enter into this
Agreement and the Debenture, to issue and sell the Debenture and the Conversion Stock as
contemplated by this Agreement, and to carry out the provisions of this Agreement and the
Debenture, has the corporate power and authority to own and hold its properties owned and leased
and to carry on the business in which it is engaged.

     (ii) This Agreement and the Debenture have been duly authorized, executed and delivered by the
Company, and are legal, valid and binding agreements of the Company enforceable in accordance with
their respective terms, except as the enforceability thereof may be limited by bankruptcy,
insolvency, moratorium, reorganization or similar laws affecting the enforcement of creditors’
rights generally, and except for judicial limitations on the enforcement of the remedy of specific
performance and other equitable remedies.

     (iii) The Conversion Stock has been duly authorized and reserved for issuance upon conversion
of the Debenture based upon the initial Conversion calculations and when issued upon such
conversion in accordance with the terms and conditions of the Debenture, the Conversion Stock will
be duly authorized and issued and will be fully paid and nonassessable.

     (iv) All corporate proceedings required by law or by the provisions of this Agreement to be
taken by the Board of Directors and the stockholders of the Company on or prior to the Closing Date
in connection with the execution and delivery of this Agreement and the Debenture, the offer,
issuance and sale of the Debenture and in connection with the consummation of the transactions
contemplated by this Agreement, have been duly and validly taken.

     (v) The Company is authorized by its Articles of Incorporation to issue 75,000,000 common
shares and 25,000,000 preferred shares.

     (vi) No security holder of the Company is entitled to preemptive or similar rights to
subscribe for or to purchase any shares of capital stock of the Company pursuant to the Company’s
Articles of Incorporation, nor will any security holder of the Company

13

 

be entitled to any such
rights pursuant to the Company’s Articles of Incorporation as a result of the execution or delivery
of this Agreement or the issuance of the Debenture or the Conversion Stock.

     (vii) Assuming the accuracy of the representations of the Purchaser set forth in Section 6
hereof, the Company has obtained the approval or consent of all governmental agencies or bodies
required to be obtained by it for the legal and valid execution and delivery of this Agreement and
the Debenture and the legal and valid offer, issuance and sale of the Debenture and the offer of
the Conversion Stock to the Purchaser through conversion and for the performance of the obligations
of the Company under any provisions of this Agreement or the Debenture. The Company is not in
violation of any term, provision or condition of its Articles of Incorporation or Bylaws, and the
consummation of the transactions contemplated by this Agreement will not result in any breach or
violation of the terms or provisions of, or constitute a default under, the Articles of
Incorporation or the Bylaws of the Company or to the best of such counsel’s knowledge any statute,
rule or regulation known to such counsel to be applicable to the Company.

     (viii) Upon due and diligent inquiry, the primary lawyers have no actual knowledge of any
litigation, proceeding or governmental investigation pending or threatened against the Company, its
key management employees, properties or business which, if determined adversely to the Company;
would have a material adverse effect upon the financial condition, operations, results of
operations or business of the Company.

          (b) The Company shall have delivered to the Purchaser an opinion
Thor Christensen, Executive Vice President and Chief Legal Counsel for the
Company, dated the Closing Date, to the effect that:

     (i) The Company is a duly and validly organized and existing corporation in good standing
under the laws of the State of Minnesota; has the corporate power and authority to enter into this
Agreement and the Debenture, to issue and sell the Debenture and the Conversion Stock as
contemplated by this Agreement, and to carry out the provisions of this Agreement and the
Debenture, has the corporate power and authority to own and hold its properties owned and leased
and to carry on the business in which it is engaged; and has not failed to qualify to do business
as a foreign corporation in good standing in any state or jurisdiction wherein the nature of its
activities or of its properties owned or leased makes such qualification necessary and failure to
be so qualified would have a material adverse effect upon the Company.

     (ii) This Agreement and the Debenture have been duly authorized, executed and delivered by the
Company, and are legal, valid and binding agreements of the Company enforceable in accordance with
their respective terms, except as the enforceability thereof may be limited by bankruptcy,
insolvency, moratorium, reorganization or similar laws affecting the enforcement of creditors’
rights generally, and except for judicial limitations on the enforcement of the remedy of specific
performance and other equitable remedies.

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     (iii) The Conversion Stock has been duly authorized and reserved for issuance upon conversion
of the Debenture based upon the initial Conversion calculations and when issued upon such
conversion in accordance with the terms and conditions of the Debenture and those of this Agreement
the Conversion Stock will be duly authorized and issued and will be fully paid and nonassessable.

     (iv) All corporate proceedings required by law or by the provisions of this Agreement to be
taken by the Board of Directors and the stockholders of the Company on or prior to the Closing Date
in connection with the execution and delivery of this Agreement and the Debenture, the offer,
issuance and sale of the Debenture and in connection with the consummation of the transactions
contemplated by this Agreement, have been duly and validly taken.

     (v) The Company is authorized by its Articles of Incorporation to issue 75,000,000 common
shares and 25,000,000 preferred shares. There are 5,207,007 common shares duly issued and
outstanding, all of which are fully paid and nonassessable. None of the preferred shares have ever
been issued and outstanding. The issuance and sale of such outstanding shares were exempt from
registration under the Securities Act and such shares were issued in conformity with the permit or
qualification requirements of all applicable state securities laws. Except for such common shares,
the Company has no other authorized or outstanding series or class of capital stock, and, to the
knowledge of such counsel, there are no outstanding securities convertible into common shares of
the Company or outstanding options, warrants or other rights to acquire securities of the Company,
other than the convertible notes, options and warrants disclosed in the Private Placement
Memorandum attached to this Agreement as Exhibit D or set forth in the schedules attached to this
Agreement as Exhibit C. To the knowledge of such counsel, there are no obligations on the part of
the Company to purchase or redeem any outstanding shares of capital stock of the Company.

     (vi) No security holder of the Company is entitled to preemptive or similar rights to
subscribe for or to purchase any shares of capital stock of the Company, nor will any security
holder of the Company be entitled to any such rights as a result of the execution or delivery of
this Agreement or the issuance of the Debenture or the Conversion Stock.

     (vii) Assuming the accuracy of the representations of the Purchaser set forth in Section 6
hereof, the Company has obtained the approval or consent of all governmental agencies or bodies
required to be obtained by it for the legal and valid execution and delivery of this Agreement and
the Debenture and the legal and valid offer, issuance and sale of the Debenture and the offer of
the Conversion Stock to the Purchaser through conversion and for the performance of the obligations
of the Company under any provisions of this Agreement or the Debenture. The Company is not in
violation of any term, provision or condition of its Articles of Incorporation or Bylaws, or, to
the best of such counsel’s knowledge, in violation of any agreement or other instrument known to
such counsel to which the Company is a party or by which it is bound or to which any of its
properties, assets or business is subject or any judgment, decree or order known to such counsel or
to the best of such counsel’s knowledge any statute, rule or regulation;

15

 

and the execution,
delivery and performance of this Agreement and the Debenture, the offer, issuance and sale of the
Debenture and the Conversion Stock, and the consummation of the transactions contemplated by this
Agreement will not result in any breach or violation of the terms or provisions of, or constitute a
default under, the Articles of Incorporation or the Bylaws of the Company or, to the best of such
counsel’s knowledge, in violation of any agreement or other instrument known to such counsel to
which the Company is a party or by which it is bound or to which any of its properties, assets or
business is subject or any judgment, decree or order known to such counsel or to the best of such
counsel’s knowledge any statute, rule or regulation.

     (viii) Assuming the accuracy of the representations of the Purchaser set forth in Section 6
hereof, the offer, sale, issuance and delivery of the Debenture and the offer of the Conversion
Stock to the Purchaser through conversion of the Debenture under the circumstances contemplated by
this Agreement and the Debenture are exempt from the registration and prospectus delivery
requirements of the Securities Act, and all registrations, qualifications, permits and approvals
required under applicable state securities laws for the lawful offer, sale, issuance and delivery
of the Debenture and the Conversion Stock have been obtained.

     (ix) Upon due and diligent inquiry, such counsel has no knowledge of any litigation,
proceeding or governmental investigation pending or threatened against the Company, its key
management employees, properties or business which, if determined adversely to the Company, would
have a material adverse effect upon the financial condition, operations, results of operations or
business of the Company.

          7.5 No Event of Default. There shall exist at the time of Closing no
condition or event which would constitute an Event of Default (as hereinafter defined)
or which, after notice or lapse of time or both, would constitute an Event of Default.

          7.6 Qualification Under State Securities Laws. All registrations,
qualifications, permits and approvals required under applicable state securities laws
for the lawful execution and delivery of this Agreement and the offer, sale, issuance
and delivery of the Debenture and the offer of the Conversion Stock shall have been
obtained.

          7.7 Proceedings and Documents. All corporate and other proceedings and
actions taken in connection with the transactions contemplated hereby and all
certificates, opinions, agreements, instruments and documents mentioned herein or
incident to any such transaction shall be satisfactory in form and substance to the
Purchaser and their special counsel.

     8. Affirmative Covenants. Subject to the provisions of Section 14 hereof, the Company
covenants and agrees that:

          8.1 Corporate Existence. The Company will maintain its corporate existence
in good standing and comply with all applicable laws and regulations of the United
States or of any state or states thereof or of any political subdivision thereof and of
any governmental authority where failure to so comply would have a material adverse
impact on the Company or its business or operations.

16

 

          8.2 Books of Account and Reserves. The Company will keep books of record
and accounts in which full, true and correct entries are made of all of its dealings,
business and affairs, in accordance with generally accepted accounting principles. The
Company will employ certified public accountants selected by the Board of Directors of
the Company who are “independent” within the meaning of the accounting regulations of
the Commission and have annual audits made by such independent public accountants in
the course of which such accountants shall make such examinations, in accordance with
generally accepted auditing
standards, as will enable them to give such reports or opinions with respect to the
financial statements of the Company as will satisfy the requirements of the
Commission in effect at such time with respect to certificates and opinions of
accountants.

          8.3 Furnishing of Financial Statements and Corporate Information. The
Company will deliver to the Purchaser:

          (a) as soon as practicable, but in any event within 30 days after
the close of each month, unaudited balance sheets of the Company as of the end
of such month, together with the related statements of operations and a
statement of sources and uses of cash for such month, setting forth the
budgeted figures for such month prepared and submitted in connection with the
Company’s annual plan as required under Section 8.5 hereof and in comparative
form figures for the corresponding month of the previous fiscal year, all in
reasonable detail and certified by the Chief Financial Officer of the Company,
subject to year-end adjustments;

          (b) as soon as practicable, but in any event within 120 days after
the end of each fiscal year, a balance sheet of the Company, as of the end of
such fiscal year, together with the related statements of operations,
stockholders’ equity and a statement of sources and uses of cash for such
fiscal year, setting forth in comparative form figures for the previous fiscal
year, all in reasonable detail and duly certified by the Company’s independent
Certified Public Accountants, which accountants shall have given the Company an
opinion, unqualified as to the scope of the audit, regarding such financial
statements;

          (c) concurrently with the delivery of any financial statements
referred to in paragraphs (a) and (b) of this Section 8.3, current schedules of
Indebtedness for Borrowed Money and Senior Indebtedness, as these terms are
hereinafter defined, together with a certificate of the Chief Executive Officer
and Chief Financial Officer of the Company to the effect that such schedules
are accurate and correct and that there exists no condition or event which
constitutes an event of default with respect to any indebtedness of the
Company, or, if any such condition or event exists, specify the nature and
period of existence thereof and what action the Company is taking or proposes
to take with respect thereto;

          (d) within 90 days after the end of each fiscal year, and promptly
upon request of the Purchaser at any time during the fiscal year up to four
times per fiscal year, written notice of the current number of shares that
would be issued to the Purchaser if the Purchaser elected at the last business
day of the fiscal year or as of the date of the request, as the case may be, to
convert the entire Convertible Debenture into fully paid and nonassessable
shares of Common Stock of the Company that represent twenty percent (20%) of
the Fully Diluted Outstanding Shares of Common Stock of the Company After
Conversion as that term is defined in the Debenture;

17

 

          (e) concurrently with the delivery in each year of the financial
statements referred to in paragraph (b) of this Section 8.3, a statement and
report signed by the independent Certified Public Accountants who certified
such financial statements to the effect that they have read this Agreement and
that in the course of the audit upon which their certificate was based they
became aware of no condition or event which constituted an Event of Default or
which, after notice or lapse of time or both, would constitute an Event of
Default or if such accountants did become aware of any such condition or event,
specifying the nature and period of existence thereof;

          (f) promptly after the submission thereof to the Company, copies of
all reports and recommendations submitted by independent Certified Public
Accountants in connection with any annual or interim audit of the accounts of
the Company made by such accountants;

          (g) promptly upon transmission thereof, copies of all reports,
proxy statements, registration statements and notifications filed by the
Company with the Commission pursuant to any act administered by the Commission
or furnished to stockholders of the Company or to any national securities
exchange;

          (h) with reasonable promptness, such other financial data relating
to the business, affairs and financial condition of the Company as is available
to the Company and as from time to time the Purchaser may reasonably request;

          (i) at least 30 days prior to the earlier of (i) the execution of
any agreement relating to any merger or consolidation of the Company with
another corporation, or a plan of exchange involving the outstanding capital
stock of the Company, or the sale, transfer or other disposition of all or
substantially all of the property, assets or business of the Company to another
corporation, or (ii) the holding of any meeting of the stockholders of the
Company for the purpose of approving such action, written notice of the terms
and conditions of such proposed merger, consolidation, plan of exchange, sale,
transfer or other disposition;

          (j) within 15 days after the Company learns in writing of the
commencement or threatened commencement of any material suit, legal or
equitable, or of any material administrative, arbitration or other proceeding
against the Company or its businesses, assets or properties, written notice of
the nature and extent of such suit or proceeding; and

          (k) with reasonable promptness, copies of all minutes of meetings
of the Company’s Shareholders and/or its Board of Directors, along with
documentation of all Corporate actions of the Company.

          8.4 Inspection. The Company will permit the Purchaser and any of its
partners, officers or employees, or any outside representatives designated by the
Purchaser and reasonably satisfactory to the Company, to visit and inspect at the
Purchaser’s expense the business offices of the Company and any of the properties of
the Company, including their books and records (and to make photocopies thereof or
make extracts therefrom), and to discuss their affairs, finances, and accounts with
their officers, lawyers and accountants, except with respect to trade secrets and
similar confidential information, all to such reasonable extent and at such

18

 

reasonable times and intervals as such Purchaser may reasonably request during
normal business hours. Except as otherwise required by laws or regulations
applicable to a Purchaser, the Purchaser shall maintain, and shall require its
representatives to maintain, all information obtained pursuant to Section 8.3
hereof, this Section 8.4 and Section 8.5 hereof on a confidential basis.

          8.5 Preparation of Budgets. Whenever the Company shall prepare and submit
to its Board of Directors for review and approval any budget, such as a .capital or
operating expense budget, the Company will, simultaneously with the submission thereof
to the Board of Directors, deliver a copy of each such budget and any modification
thereof that is provided to the Board of Directors to the Purchaser.

          8.6 Payment of Taxes and Maintenance of :Properties. The Company will:

          (a) pay and discharge promptly, or cause to be paid and discharged
promptly when due and payable, all taxes, assessments and governmental charges
or levies imposed upon it or upon its income or upon any of its properties, as
well as all material claims of any kind (including claims for labor, material
and supplies) which, if unpaid, might by law become a lien or charge upon its
property; provided, however, that the Company shall not be required to pay any
such tax, assessment, charge, levy or claim if the amount, applicability or
validity thereof shall currently be contested in good faith by appropriate
proceedings and if the Company shall have set aside on its books reserves
(segregated to the extent required by generally accepted accounting principles)
deemed adequate by it with respect thereto; and

          (b) maintain and keep, or cause to be maintained and kept, its
properties in good repair, working order and condition, and from time to time
make, or cause to be made, all repairs and renewals and replacements which in
the opinion of the Company are necessary and proper so that the business
carried on in connection therewith may be properly and advantageously conducted
at all times; the Company will maintain or cause to be maintained back-up
copies of all valuable papers and software.

          8.7 Insurance. The Company will obtain and maintain in force such property
damage, public liability, business interruption, worker’s compensation, indemnity bonds
and other types of insurance as the Company’s executive officers, after consultation
with an accredited insurance broker, shall determine to be necessary or appropriate to
protect the Company from the insurable hazards or risks associated with the conduct of
the Company’s business. The Company’s executive officers shall periodically report to
the Board of Directors on the status of such insurance coverage.

     All insurance shall be maintained in at least such amounts and to such extent as shall be
determined to be reasonable by the Board of Directors; and all such insurance shall be effected and
maintained in force under a policy or policies issued by insurers of recognized responsibility,
except that the Company may effect worker’s compensation or similar insurance in respect of
operations in any state or other jurisdiction either through an insurance fund operated by such
state or other jurisdiction or by causing to be maintained a system or systems of self-insurance
which is in accord with applicable laws.

19

 

          8.8 Payment of Indebtedness and Discharge of Obligations. The Company will
pay or cause to be paid the principal of and interest and premium, if any, on all
Indebtedness for Borrowed Money heretofore or hereafter incurred or assumed by it when
and as the same shall become due and payable, unless such Indebtedness for Borrowed
Money is renewed or extended. The Company will faithfully observe, perform and
discharge all of the material. covenants, conditions and obligations which are imposed
on it by any and all indentures and other agreements securing or evidencing such
Indebtedness for Borrowed Money or pursuant to which such Indebtedness for Borrowed
Money is issued, and will not permit the continuance of any act or omission which is or
under the provisions thereof may be declared to be a material default thereunder,
unless such default is waived pursuant to the provisions thereof. The Company shall
not be required to make any payment or to take any other action by reason of this
Section 8.8 at any time while it shall be currently contesting in good faith by
appropriate proceedings its obligations to make such payment or to take such action
provided that the Company shall have set aside on its books reserves (segregated to the
extent required by generally accepted accounting principles) deemed adequate by it with
respect thereto.

          8.9 Directors’ and Stockholders’ Meetings. The Company agrees, as a
general practice, to hold a meeting of its Board of Directors at least once a year, and
during each year to hold its annual meeting of stockholders on or approximately on the
date provided in its Bylaws.

          8.10 Replacement of Debenture or Certificates Representing Conversion Stock.
Upon receipt of evidence reasonably satisfactory to the Company of the loss, theft,
destruction or mutilation of the Debenture or certificates representing Conversion
Stock, and, in the case of any such loss, theft or destruction, upon delivery of a bond
of indemnity satisfactory to the Company, or, in the case of any such mutilation, upon
surrender and cancellation of the Debenture or certificates representing Conversion
Stock, as the case may be, the Company will issue a new Debenture or certificates
representing Conversion Stock, as the case may be, of like tenor, in lieu of such lost,
stolen, destroyed or mutilated Debenture or certificates representing Conversion Stock,
as the case may be.

          8.11 Application of Proceeds. Unless otherwise approved by the Purchaser,
the net proceeds received by the Company from the sale of the Debenture shall be used
substantially for working capital purposes. Upon proper invoice, the Company shall pay
Closing expenses and attorney fees of Purchaser in a sum not to exceed seven thousand
five hundred and no/100 dollars ($7,500.00).

          8.12 Retirement Plans. The Company will cause each retirement plan of the
Company in which any employees of the Company participate that is subject to the
provisions of ERISA and the documents and instruments governing each such plan to be
conformed to when necessary, and to be administered in a manner consistent with, those
provisions of ERISA which may, from time to time, become effective and operative with
respect to such plans; if requested by the Purchaser in writing from time to time,
furnish to the Purchaser a copy of any annual report with respect to each such plan
that the Company files with the Secretary of Labor pursuant to ERISA; and at such time
as such insurance shall be available at rates deemed commercially reasonable by the
Company, maintain insurance against the contingent liability against the net worth of
the Company imposed in respect of each such plan by the provisions of ERISA.

20

 

          8.13 Filing of Reports. The Company will, from and after such time as it
has securities registered pursuant to Section 12 of the Securities Exchange Act of
1934, as amended, or has securities registered pursuant to the Securities Act, make
timely filing of such reports as are required to be filed by it with the Commission so
that Rule 144 under the Securities Act or any successor provision thereto will be
available to the security holders of the Company who are otherwise able to take
advantage of the provisions of such Rule.

          8.14 Patents and Other Intangible Rights. The Company will apply for, or
obtain assignments of, or licenses to use, all patents, trademarks, trademark rights,
trade names, trade name rights and copyrights which in the opinion of a prudent and
experienced businessman operating in the industry in which the Company is operating;
are desirable or necessary for the conduct and protection of the business of the
Company.

          8.15 Exchange of Debenture. The Company will at any time, at the Company’s
expense (except for any transfer tax payable), at the written request of the Holder of
the Debenture and upon surrender of such Debenture for such purpose, issue new
Debentures in exchange therefor in the denomination of $5,000, or any multiple thereof
specified by the Purchaser, in an aggregate principal amount equal to the then unpaid
principal amount of the Debenture surrendered and substantially in the form of Exhibit
A to this Agreement with appropriate insertions and variations.

     9. Negative Covenants. The Company will be limited and restricted as follows:

          9.1 Dividends on or Redemption of Capital Stock. Without the prior
approval of the Holder of the Debenture, the Company will not declare or pay any
dividend or make any other distribution on any shares of capital stock or purchase,
redeem or otherwise acquire for any consideration, or set aside a sinking fund or other
fund for the redemption or repurchase of any shares of capital stock or any warrants,
rights or options to purchase shares of capital stock.

          9.2 Other Restrictions. The Company will not without the prior approval of
the Holder of the Debenture:

          (a) guarantee, endorse or otherwise be or become contingently
liable in connection with the obligations, securities or dividends of any
person, firm, association or corporation, other than the Company, except that
the Company may endorse negotiable instruments for collection in the ordinary
course of business; or

          (b) make loans or advances to any person (including without
limitation to any officer, director or stockholder of the Company), firm,
association or corporation in excess of $10,000, except advances to suppliers
and employees made in the ordinary course of business; or

          (c) purchase or invest in the stock or obligations of any other
person, firm or corporation; or

          (d) make any material change in the nature of its business as
carried on at the date of this Agreement.

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          9.3 Limitations Upon Capital Reorganization of Common Stock, Consolidation, or
Merger. No merger or acquisition of the Company, or substantially all of its
assets, or capital reorganization or reclassification of the capital stock of the
Company or voluntary dissolution, liquidation, or in bankruptcy filing shall occur
absent the written concurrence of the Purchaser.

     10. The Debenture.

          10.1 Conversion of Debenture. The Holder of the Debenture may, at its
option, at any dale and from time to time, convert such Debenture, or any part thereof,
into Conversion Stock upon the terms and conditions set forth in the Form of Debenture.

          10.2 Stock Fully Paid; Reservation of Shares. The Company covenants and
agrees that all Conversion Stock that may be issued upon conversion of the Debenture
will, upon issuance in accordance with the terms of the Debenture, be fully paid and
nonassessable, and shall, at the time of issuance, not be diluted, and that the
issuance thereof shall not give rise to any preemptive rights on the part of any
person. The Company further covenants and agrees that the Company will at all times
have authorized and reserved a sufficient number of shares of its Common Stock for the
purpose of issue upon the conversion of the Debenture.

     The Convertible Debenture is convertible in whole at any time prior to its payment at the
option of the Purchaser into fully paid and nonassessable shares of Common Stock of the Company
constituting twenty percent (20%) of all classes of the Common Stock of the Company on a fully
diluted basis, as further explained in paragraph 3(b) of the Convertible Debenture. In addition,
as further explained in paragraph 3(b) of the Convertible Debenture, the Convertible Debenture is
convertible in part at any time prior to its payment at the option of the Purchaser into fully paid
and nonassessable shares of Common Stock of the Company constituting a proportionate percentage of
twenty percent (20%) of all classes of the Common Stock of the Company on a fully diluted basis in
the ratio that the amount of the Convertible Debenture being converted bears to the total amount of
the Convertible Debenture acquired by the Purchaser.
Under no circumstances shall paragraph 3(b) of the Convertible Debenture be read to entitle
the Purchaser to shares of Common Stock of the Company constituting less than 20% of all classes of
the Common Stock of the Company on a fully diluted basis upon conversion in full of the Convertible
Debenture.

          10.3 Number of Shares to be Issued Upon Conversion. The number of shares of
Common Stock issuable upon full conversion of the Debenture will be as set forth in the
Form of Debenture, which is equal to twenty percent (20%) of all classes of the Common
Stock of the Company on a fully diluted basis. The number of shares of the Common
Stock of the Company issuable upon partial conversion shall be equivalent to the ratio
that the amount of the Convertible Debenture being converted bears to the total amount
of the Convertible Debenture originally acquired by the Purchaser.

     11. {Intentionally Omitted}

     12. {Intentionally Omitted}

22

 

     13. Default.

          13.1 Events of Default. Each of the following events shall be an event of
default (an “Event of Default”) for purposes of this Agreement:

          (a) if default shall be made in the punctual payment of interest on
the Debenture, and such default shall have continued for a period of 15 days
after written notice thereof to the Company by the Holder of the Debenture; or

          (b) if default shall be made in the punctual payment of the
principal of the Debenture; or

          (c) if the Company becomes insolvent or bankrupt, or admits in
writing its inability to pay its debts as they mature, or makes an assignment
for the benefit of creditors, or ceases doing business as a going concern, or
the Company applies for or consents to the appointment of a trustee or receiver
for the Company, or for the major part of its property; or

          (d) if a trustee or receiver is appointed for the: Company or for
the major part of its property and the order of such appointment is not
discharged, vacated or stayed within 30 days after such appointment; or

          (e) if any judgment, writ or warrant of attachment or of any
similar process in an amount in excess of $50,000 shall be entered or tiled
against the Company or against any of the property or assets of the Company and
remains unpaid, unvacated, unbonded or unstayed for a period of 120 days; or

          (f) if an order for relief shall be entered in any Federal
bankruptcy proceeding in which the Company is the debtor; or if bankruptcy,
reorganization,
arrangement, insolvency, or liquidation proceedings, or other proceedings
for relief under any bankruptcy or similar law or laws for the relief of
debtors, are instituted by or against the Company and, if instituted against
the Company, are consented to or, if contested by the Company, are not
dismissed by the adverse parties or by an order, decree or judgment within
120 days after such institution; or

          (g) if the Company shall default in any material respect in the due
and punctual performance of any covenant or agreement in any debenture
(including without limitation the Debenture which is the subject of this
Agreement), bond, indenture, loan agreement, debenture agreement, mortgage,
security agreement or other instrument evidencing or related to Indebtedness
for Borrowed Money, and such default shall continue for more than the period of
notice and/or grace, if any, therein specified and shall not have been waived
(any default in any material respect in the due and punctual performance of any
covenant or agreement in this Agreement or the Debenture shall not constitute
an Event of Default unless such default continues for a period of 15 days after
written notice thereof to the Company); or

          (h) if any representation or warranty made by or on behalf of the
Company in this Agreement or in any certificate, report or other instrument
delivered under or pursuant to any term hereof or thereof shall prove to have
been untrue or incorrect in any material respect as of the date of this
Agreement or as of the Closing Date, or (ii) if any report, certificate,
financial statement or financial schedule or other instrument prepared or
purported to be prepared by the

23

 

Company or any officer of the Company furnished
or delivered under or pursuant to this Agreement after the Closing Date shall
prove to be untrue or incorrect in any material respect as of the date it was
made, furnished or delivered; or

          (i) if the Company undertakes any action designed to diminish the
conversion rights of Purchaser in the absence of advance written permission of
Purchaser; or

          (j) if default shall be made in the due and punctual performance or
observance of any other term contained in this Agreement, and such default
shall have continued for a period of 15 days after written notice thereof to
the Company by the Holder of the Debenture.

          13.2 Remedies Upon Events of Default. Upon the occurrence of an Event of
Default as herein defined, and so long as such Event of Default continues unremedied,
then, unless such Event of Default shall have been waived by the Holder of the
Debenture, then the Holder of the Debenture shall be entitled by notice to declare the
principal of and any accrued interest on the Debenture to be immediately due and
payable, and thereupon the Debenture, including both principal and interest shall
become immediately due and payable provided, however, that when any Event of Default
described in Section 13.1(f) hereof has
occurred, the Debenture shall immediately become due and payable without
presentment, demand or notice of any kind and (b) the Purchaser of the Debenture
shall be entitled to designate such number of members to the Board of Directors of
the Company as constitutes 20% of the total number of members of the Board of
Directors as provided herein.

          13.3 Designation of Directors. In the event the Purchaser of the Debenture
is entitled to designate members constituting 20% of the total number of members of the
Board of Directors of the Company pursuant to Section 13.2 hereof, the Company shall,
immediately upon receiving written notice from the Holder of the Debenture, call a
special stockholders’ meeting to be held as soon as possible, but in any event within
fifteen days of the date of the notice of such meeting. At such special stockholders’
meeting, 20% of the directors of the Company, shall be elected from designees nominated
by the Holder of the Debenture. Any right of the Holder of the Debenture to continue
to designate 20% of the Board of Directors of the Company shall expire, and a
stockholders’ meeting to elect new directors shall be called, six months after the
later of (a) the curing of the Event Default upon which the right was exercised, or (b)
the curing of any Event of Default occurring after the Event of Default upon which such
right was exercised.

          13.4 Notice of Defaults. When, to its knowledge, any Event of Default has
occurred or exists, the Company agrees to give written notice within three business
days of such Event of Default to the Holder of the Debenture.

          13.5 Suits for Enforcement. In case any one or more Events of Default shall
have occurred and be continuing, unless such Events of Default shall have been waived
in the manner provided in Section 13.2 hereof, the Holder of the Debenture may proceed
to protect and enforce its rights under this Section 13 by suit in equity or action at
law. It is agreed that in the event of such action the Holder of the Debenture shall
be entitled to receive all reasonable fees, costs and expenses incurred, including
without limitation such reasonable fees and expenses of

24

 

attorneys (whether or not
litigation is commenced) and reasonable fees, costs and expenses of appeals.

          13.6 Remedies Cumulative. No right, power or remedy conferred upon the
Holder of the Debenture shall be exclusive, and each such right; power or remedy shall
be cumulative and in addition to every other right, power or remedy, whether conferred
hereby or by any such security or now or hereafter available at law or in equity or by
statute or otherwise.

          13.7 Remedies not Waived. No course of dealing between the Company and the
Holder of the Debenture, and no delay in exercising any right, power or remedy
conferred hereby or by any such security or now or hereafter existing at law or in
equity or by statute or otherwise, shall operate as a waiver of or otherwise prejudice
any such right, power or remedy; provided, however, that this Section 13.7 shall not be
construed or applied so as to negate the provisions and intent of any statute which is
otherwise applicable.

     14. Definitions. Unless the context otherwise requires, the terms defined in this
Section 14 shall have the meanings herein specified for all purposes of this Agreement, applicable
to both the singular and plural forms of any of the terms herein defined. All accounting terms
defined below shall, except as otherwise expressly provided, be determined by reference to the
Company’s books of account and in conformity with generally accepted accounting principles as
applied to such books of account in the opinion of the independent Certified Public Accountants
selected by the Board of Directors of the Company as required under the provisions of Section 8.3
hereof.

          14.1 “Common Stock” shall mean the Company’s authorized common shares, any
additional common shares which may be authorized in the future by the Company, and any
stock into which such common shares may hereafter be changed, and shall also include
stock of the Company of any other class which is not preferred as to dividends or as to
distributions of assets on liquidation, dissolution or winding up of the Company over
any other class of stock of the Company, and which is not subject to redemption.

          14.2 “Convertible Securities” shall mean evidences of indebtedness, shares of stock
or other securities which are at any time directly or indirectly convertible into or
exchangeable for shares of Common Stock.

          14.3 “Indebtedness for Borrowed Money” shall include only indebtedness of the
Company incurred as the result of a direct borrowing of money and shall not include any
other indebtedness including, but not limited to, indebtedness incurred with respect to
trade accounts.

          14.4 “Permitted Liens” shall mean (a) liens for taxes and assessments or
governmental charges or levies not at the time due or in respect of which the validity
thereof shall currently be contested in good faith by appropriate proceedings; (b)
liens existing as of the date of this Agreement, (c) liens arising in connection with
purchase money security interests; and (d) liens in respect of pledges or deposits
under worker’s compensation laws or similar legislation, carriers’, warehousemen’s,
mechanics’, laborers’ and materialmen’s, landlord’s and statutory and similar liens, if
the obligations secured by such liens are not then delinquent or are

25

 

being contested in
good faith, and liens and encumbrances incidental to the conduct of the business of the
Company which were not incurred in connection with the borrowing of money or the
obtaining of advances or credits and which do not in the aggregate materially detract
from the value of its property or materially impair the use thereof in the operation of
its business.

          14.5 “Senior Indebtedness” shall mean (a) the principal of all Indebtedness for
Borrowed Money of the Company to banks, insurance companies or other financial
institutions, (b) the present value of net minimum lease payments of all leases under
which the Company is the lessee and which are required to be capitalized under
generally accepted accounting principles, (c) the principal of all indebtedness of the
Company under installment purchase agreements, and (d) the principal of all
indebtedness of the Company to the owners of any real property leased by the Company
for leasehold improvements financed by such owners.

     15. Consents; Waivers and Amendments. Except as otherwise specifically provided
herein, in each case in which approval of the Holder of the Debenture is required by the terms of
this Agreement, such requirement shall be satisfied by the written consent of the Holder of the
Debenture. With the written consent of the Holder of the Debenture, the obligations of the Company
under this Agreement may be waived (either generally or in a particular instance and either
retroactively or prospectively), and with the same approval the Company may enter into a
supplementary agreement for the purpose of adding any provisions to or changing in any manner or
eliminating any of the provisions of this Agreement or of any supplemental agreement or modifying
in any manner the rights and obligations of the Holder of the Debenture. The Holder of Debenture
shall respond promptly to any request by the Company with respect to a proposed amendment, consent
or waiver and will not unreasonably withhold its approval or consent thereto.

     16. Changes, Waivers, etc. Neither this Agreement nor any provision hereof may be
changed, waived, discharged or terminated orally, but only by a statement in writing signed by the
party against which enforcement of the change, waiver, discharge or termination is sought, except
to the extent provided in Section 15 hereof.

     17. Payment of Fees and Expenses of Purchaser. The Company will pay all fees and
expenses incurred by the Purchaser with respect to the enforcement of the rights granted under this
Agreement or the agreements contemplated hereby.

     18. Notices. All notices, requests, consents and other communications required or
permitted hereunder shall be in writing and shall be delivered, or mailed first-class postage
prepaid, registered or certified mail,

26

 

	 	 	 	 	 	 	 
	 	 	(a)	 	if to the Holder of the Debenture:
	 
	 	 	 	 	 	 
	 

	 	 	 	To:
	 	Honorable Valentino White
	 

	 	 	 	 	 	Chairman
	 

	 	 	 	 	 	Spirit Lake Sioux Tribe
	 

	 	 	 	 	 	Spirit Lake Tribal Council Office
	 

	 	 	 	 	 	P.O. Box 359
	 

	 	 	 	 	 	Main Street
	 

	 	 	 	 	 	Fort Totten, ND 58335
	 
	 	 	 	 	 	 
	 

	 	 	 	With Copy To:
	 	Larry B. Leventhal, Esq.
	 

	 	 	 	 	 	Larry Leventhal & Associates
	 

	 	 	 	 	 	Suite 420
	 

	 	 	 	 	 	Sexton Building
	 

	 	 	 	 	 	529 South 7th Street
	 

	 	 	 	 	 	Minneapolis, Minnesota 55415
	 
	 	 	 	 	 	 
	 

	 	(b)
	 	if to the Company:	 	 
	 
	 	 	 	 	 	 
	 

	 	 	 	To:
	 	Mr. Jeffrey Mack
	 

	 	 	 	 	 	President & CEO
	 

	 	 	 	 	 	Wireless Ronin® Technologies, Inc.
	 

	 	 	 	 	 	14700 Martin Drive
	 

	 	 	 	 	 	Eden Prairie, Minnesota 55344
	 
	 	 	 	 	 	 
	 

	 	 	 	With Copy To:
	 	Thor Christensen, Esq.
	 

	 	 	 	 	 	Vice President Corporate Counsel
	 

	 	 	 	 	 	Wireless Ronin® Technologies, Inc.
	 

	 	 	 	 	 	14700 Martin Drive
	 

	 	 	 	 	 	Eden Prairie, Minnesota 55344

and such notices and other communications shall for all purposes of this Agreement be treated as
being effective or having been given if delivered personally, or, if sent by mail, when received.

     19. Survival of Representations and Warranties, etc. All representations and
warranties contained herein shall survive the execution and delivery of this Agreement, any
investigation at any time made by the Purchaser or on its behalf, and the sale and purchase of the
Debenture and payment therefor and shall terminate upon payment or conversion in full of all
amounts due under the Debenture. All statements contained in any certificate, instrument or other
writing delivered by or on behalf of the Company pursuant hereto or in connection with or
contemplation of the transactions herein contemplated (other than legal opinions) shall constitute
representations and warranties by the Company hereunder.

     20. Parties in Interest. All the terms and provisions of this Agreement shall be
binding upon and inure to the benefit of and be enforceable by the respective successors and
assigns of the parties hereto, whether so expressed or not, and, in particular, shall inure to the
benefit of and be enforceable by the Holder of the Debenture.

27

 

     21. Headings. The headings of the Sections and paragraphs of this Agreement have been
inserted for convenience of reference only and do not constitute a part of this Agreement.

     22. Choice of Law. It is the intention of the parties that the laws of Minnesota
shall govern the validity of this Agreement, the construction of its terms and the interpretation
of the rights and duties of the parties.

     23. Counterparts. This Agreement may be executed concurrently in two or more
counterparts, each of which shall be deemed an original, but all of which together shall constitute
one and the same instrument.

     If you are in agreement with the foregoing, please sign the form of acceptance on the enclosed
counterpart of this letter and return the same to the undersigned, whereupon this letter shall
become a binding contract between you and the undersigned.

	 	 	 	 	 
	 	Very truly yours,

WIRELESS RONIN® TECHNOLOGIES, INC.

 	 
	 	By:  	  /s/  Jeffrey C. Mack
 	 
	 	 	Jeffrey C. Mack 	 
	 	 	President & CEO 	 
	 
	 	 	 
	 	By:  	                                                    /s/ Stephen E. Jacobs
 	 
	 	 	Stephen E. Jacobs 	 
	 	 	Executive Vice President & CFO 	 
	 

The foregoing Agreement is hereby accepted as

of the date first above written.

SPIRIT LAKE SIOUX TRIBE

	 	 	 	 	 	 	 
	By:

	 	  /s/ Valentino White Sr.
 

	 
	 
	 	 	 	 
	 

	 	Print Name:	Valentino White Sr. 

	 
	 	 	 	 
	 

	 	Its:     	Chairman 

28exv10w15

 

EXHIBIT 10.15

THIS CONVERTIBLE DEBENTURE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS
AMENDED, OR APPLICABLE STATE SECURITIES LAWS. NO SALE OR DISPOSITION MAY BE EFFECTED EXCEPT IN
COMPLIANCE WITH AN EFFECTIVE REGISTRATION STATEMENT RELATED THERETO OR AN OPINION OF COUNSEL FOR
THE HOLDER, SATISFACTORY TO PAYOR, THAT SUCH REGISTRATION IS NOT REQUIRED UNDER THE ACT.

	 	 	 
	$3,000,000
	 	September 7, 2005

Eden Prairie, Minnesota

CONVERTIBLE DEBENTURE

10% INTEREST ONLY

DUE DECEMBER 31, 2009

     For
value received, WIRELESS RONIN® TECHNOLOGIES, INC.
(“Payor” or “Company”) promises to pay
to the Spirit Lake Tribe, a federally recognized Native American
Indian Tribe (“Holder”), at such
place as the Holder may from time to time designate to Payor, the principal sum of THREE MILLION
DOLLARS ($3,000,000), together with all accrued and unpaid interest thereon as set forth below.

     Interest on the unpaid principal balance of this Convertible Debenture (the “Principal
Balance”) will accrue at the rate of ten percent (10%) per annum commencing, with respect to
$2,000,000 of the Principal Balance on January 5, 2005 and with respect to $1,000,000 of the
Principal Balance on the date hereof, and continuing until this Convertible Debenture is fully paid
(computed on the basis of a 360 day year, 30 day month), and will be payable in quarterly
installments in arrears as set forth below. If not sooner converted as provided below, the entire
unpaid balance of principal and all accrued and unpaid interest will be due and payable on December
31, 2009 (the “Maturity Date”). Payment of the accrued interest on $2,000,000 of the Principal
Balance of this Convertible Debenture shall be made by Payor in quarterly installments in the
amount of $50,000 on the last day of March, June, September and December in each year, commencing
on March 31, 2005, until the principal hereof shall have been paid in full. Payment of the accrued
interest on $1,000,000 of the Principal Balance of this Convertible Debenture shall be made by
Payor in quarterly installments of $25,000 on the last day of March, June, September and December
in each year, commencing on September 30, 2005 (such interest amount for the quarter ending
September 30, 2005 shall be prorated for the period from the issuance of this Convertible
Debenture). Except as provided in paragraph 9 hereof, the principal of and interest on this
Convertible Debenture shall be paid in lawful money of the United States. The Principal Balance of
this Convertible Debenture includes the $2,000,000 principal amount of the convertible debenture
issued by Payor to Holder on January 5, 2005, and this Convertible Debenture amends, restates and
supersedes such prior Convertible Debenture.

     This Convertible Debenture is convertible in whole or in part into fully paid and
nonassessable shares of Common Stock of the Company that represent up to thirty percent (30%) of
the Fully Diluted Outstanding Shares of Common Stock of the Company After Conversion, as that term
is hereinafter defined, at any time prior to its payment at the option of the Holder hereof.

 

 

     The Holder of this Convertible Debenture is only required to forego the right to receive
repayment of each dollar of the original principal amount of the Convertible Debenture that the
Holder elects to convert into fully paid and nonassessable shares of Common Stock of the Company
and is not required to pay any additional monies or consideration as a condition precedent to
exercising the right to convert.

     This Convertible Debenture has been issued under the terms and provisions of the Convertible
Debenture Purchase Agreement, dated January 5, 2005, as amended by the Amended and Restated
Convertible Debenture Purchase Agreement, dated September 7, 2005 (the “Agreement”), between the
Payor Wireless Ronin® Technologies, Inc. and the Holder Spirit Lake Tribe. This Convertible
Debenture amends, restates and supersedes that certain Convertible Debenture in the principal
amount of $2,000,000 dated January 5, 2005.

     Upon the occurrence of any one or more of the Events of Default specified in the Agreement,
all amounts then remaining unpaid on this Convertible Debenture, including accrued interest, may be
declared to be or shall become immediately due and payable as provided in the Agreement.

     This Convertible Debenture is subject to the following terms and conditions.

     1. Prepayment — Payor Option.

          (a) This Convertible Debenture may be prepaid at the option of the Payor as set forth below.
Any such call for prepayment of this Convertible Debenture shall be made by giving written notice
to the Holder hereof not less than sixty (60) days prior to the date fixed by the Payor for
prepayment of this Convertible Debenture (the “Prepayment Date”). Notice of call for prepayment
having been given as aforesaid, the outstanding principal amount of this Convertible Debenture
together with unpaid interest accrued thereon to the Prepayment Date, shall become due and payable
on the Prepayment Date. From and after the Prepayment Date, unless the Payor shall default in such
prepayment, interest shall cease to accrue on the principal amount to be prepaid. Nothing in this
paragraph 1 shall affect in any way the right of the Holder of this Convertible Debenture to covert
this Convertible Debenture into fully paid and nonassessable shares of Common Stock of Wireless
Ronin® Technologies, Inc. at any time and from time to time in accordance with paragraph 3 hereof.

          (b) Payor may prepay such portion of the $3,000,000 Principal Balance as Payor may desire in
accordance with the notice and other requirements of paragraph 1(a); however, Payor shall be
required to pay a prepayment penalty equal to (A) 20% of such amount of Principal Balance to be
prepaid if the Prepayment Date is on or before January 5, 2008 or (B) 10% of such amount of
Principal Balance to be prepaid if the Prepayment Date is after January 5, 2008; provided, however,
that the prepayment penalty shall be limited to 10% on the prepayment of up to $1,000,000 of the
Principal Balance if sixty (60) days advance notice is given by December l, 2005 for prepayment to
occur no later than March 1, 2006.

     2. Prepayment — Convertible Debenture Holder Option.

          (a) The Holder of this Convertible Debenture may require that this Convertible Debenture be
prepaid by the Payor in whole (but not in part) upon (i) the sale, lease,

2

 

license or other disposition of all or substantially all of the Company’s assets (other than
in the ordinary course of the Company’s business), (ii) the merger or consolidation of the Company
into or with another corporation or the merger or consolidation of any other corporation into or
with the Company or a plan of exchange between the Company and any other corporation (in which
consolidation or merger or plan of exchange any stockholders of the Company receive distributions
of cash or securities or other property). The Company shall give the Holder of this Convertible
Debenture written notice of such impending transaction not later than 60 days prior to the
stockholders’ meeting of the Company called to approve such transaction, or 60 days prior to the
closing of such transaction, whichever is earlier, and shall also notify such Holder in writing of
the final approval of such transaction. The first of such notices shall give the proposed
effective date of the transaction (the “Effective Date”) and shall describe the material terms and
conditions of the transaction and of this paragraph 2(a) (including, without limiting the
generality of the foregoing, a description of the value of the consideration, if any, being offered
to the holders of the outstanding securities of the Company), and the Company shall thereafter give
such Holder prompt notice of any material changes to such terms and conditions. The transaction
shall in no event take place sooner than 60 days after the mailing by the Company of the first
notice provided for herein or sooner than 20 days after the mailing by the Company of any notice of
material changes provided for herein, whichever is later in time. Any election for prepayment of
this Convertible Debenture shall be made by the Holder of this Convertible Debenture giving written
notice thereof to the Company at least two days before the Effective Date. If no such notice is
given, the provisions of paragraph 4(b)(i) shall apply. Notice of election of prepayment by the
Holder of this Convertible Debenture having been given as aforesaid, the outstanding principal
amount to be prepaid together with unpaid interest accrued thereon to the Effective Date, shall
become due and payable on the Effective Date. From and after the Effective Date, unless the
Company shall default in such prepayment, interest shall cease to accrue on the principal amount to
be prepaid.

          (b) Nothing hereinabove set forth shall affect in any way the right of the Holder of this
Convertible Debenture to covert this Convertible Debenture into fully paid and nonassessable shares
of Common Stock of Wireless Ronin® Technologies, Inc. at any time and from time to time in
accordance with paragraph 3 hereof.

     3. Conversion Rights.

          (a) This Convertible Debenture is convertible in whole at any time prior to its payment at the
option of the Holder into fully paid and nonassessable shares of Common Stock of the Company
constituting thirty percent (30%) of all classes of the Common Stock of the Company on a fully
diluted basis, as further explained below in paragraph 3(b). In addition, as further explained
below in paragraph 3(b), this Convertible Debenture is convertible in part at any time prior to its
payment at the option of the Holder into fully paid and nonassessable shares of Common Stock of the
Company constituting a proportionate percentage of thirty percent (30%) of all classes of the
Common Stock of the Company on a fully diluted basis in the ratio that the amount of the
Convertible Debenture being converted bears to the total amount of the Convertible Debenture
acquired by the Holder. Under no circumstances shall paragraph 3(b) of this Convertible Debenture
be read to entitle the Holders to shares of Common Stock of the Company constituting less than 30%
of all classes of the Common Stock of the Company on a fully diluted basis upon conversion in full
of this Convertible Debenture.

3

 

          (b) The following definitions shall apply for purposes of determining the number of fully paid
and nonassessable shares of Common Stock of the Company that this Convertible Debenture is
convertible into in whole or in part at any time prior to its payment at the option of the Holder
hereof:

	 	(i)	 	Definitions

	 	(A)	 	Conversion Dollar Amount. The
“Conversion Dollar Amount” shall be the amount of par value
dollars measured by the original principal amount of the
Convertible Debenture that the Holder elects to convert into
fully paid and nonassessable shares of Common Stock of the
Company.
	 
	 	(B)	 	Percentage of the Par Value of
Convertible Debenture Converted. The “Percentage of the Par
Value of Convertible Debenture Converted” shall be equal to the
percentage resulting from dividing the Conversion Dollar Amount
by the original principal amount of the Convertible Debenture.
	 
	 	(C)	 	Maximum Percentage of Outstanding
Shares That Can Be Acquired. The “Maximum Percentage of
Outstanding Shares That Can Be Acquired” is 30%.
	 
	 	(D)	 	Conversion Ratio. The
“Conversion Ratio” shall be equal to Percentage of the Par Value
of Convertible Debenture Converted times the Maximum Percentage
of Outstanding Shares That Can Be Acquired.
	 
	 	(E)	 	Fully Diluted Outstanding Shares
of Common Stock of the Company. The “Fully Diluted Outstanding
Shares of Common Stock of the Company” shall be the aggregate as
of the date of conversion of (i) the total Outstanding Shares of
Common Stock, (ii) all shares of Common Stock of the Company
issuable upon conversion or exercise in full of all outstanding
options, warrants or other convertible securities or other
rights of any nature to acquire shares of Common Stock or
securities convertible into shares of Common Stock and (iii) all
shares of Common Stock that can be acquired as per the terms of
warrants and options that are issued to employees pursuant to
existing employment contracts (to the extent such shares were
not included in (ii)).
	 
	 	(F)	 	Fully Diluted Outstanding Shares
of Common Stock of the Company After Conversion. The “Fully
Diluted

4

 

	 	 	 	Outstanding Shares of Common Stock of the Company After
Conversion” shall be determined as of the date of conversion
by dividing the Fully Diluted Outstanding Shares of Common
Stock of the Company by (1-Conversion Ratio).
	 
	 	(G)	 	Outstanding Shares of Common
Stock. The “Outstanding Shares of Common Stock” shall include
all issued and outstanding shares of Common Stock of the
Company.

          (c) Each dollar of the original principal amount of the Convertible Debenture is convertible
into fully paid and nonassessable shares of Common Stock of the Company in whole or in part at any
time prior to its payment at the option of the Holder. The number of fully paid and nonassessable
shares of Common Stock of the Company issuable upon full or partial conversion of this Convertible
Debenture is determined as of the date of conversion by first computing the number of the Fully
Diluted Outstanding Shares of Common Stock of the Company. The Conversion Ratio is then determined
by reference to the percentage that the total Conversion Dollar Amount represents of the total
$3,000,000 original principal amount of the Convertible Debenture. The number of fully paid and
nonassessable shares of Common Stock of the Company issuable upon full or partial conversion of
this Convertible Debenture is then determined as of the date of conversion by subtracting the Fully
Diluted Outstanding Shares of Common Stock of the Company from the Fully Diluted Outstanding Shares
of Common Stock of the Company After Conversion. Under no circumstances shall the number of shares
of Common Stock of the Company issued to the Holder upon conversion of this Convertible Debenture,
when added to any shares of Common Stock of the Company issued to the Holder upon prior partial
conversions of this Convertible Debenture, represent more than 30% of the Fully Diluted Shares of
Common Stock of the Company After Conversion (when calculated after each conversion).

          (d) The foregoing computation of the number of shares of fully paid and nonassessable shares
of Common Stock of the Company that this Convertible Debenture can be converted into can be
illustrated as follows. Assuming at the date of conversion there are 12,000,000 Fully Diluted
Outstanding Shares of Common Stock of the Company and the Holder elects to convert the entire
$3,000,000 of the Convertible Debenture into Common Stock, the Conversion Ratio would then be 30%
(100% x 30%-Percentage of the Par Value of Convertible Debenture Converted times the Maximum
Percentage of Outstanding Shares That Can Be Acquired), the Fully Diluted Outstanding Shares of
Common Stock of the Company After Conversion would be 17,142,857 (12,000,000 / (1-30%)) and the
number of shares of Common Stock to be issued upon conversion would be 5,142,958
(17,142,857-12,000,000) which represents 30% of Fully Diluted Outstanding Shares of Common Stock of
the Company After Conversion.

          (e) In order to exercise the conversion privilege, the Holder hereof shall surrender this
Convertible Debenture to the Company at its principal office, accompanied by written notice to the
Company that the Holder elects to convert this Convertible Debenture or a part hereof. This
Convertible Debenture or the part hereof to be converted shall be deemed to have been converted on
the day of surrender of this Convertible Debenture for conversion in

5

 

accordance with the foregoing provisions, and at such time the rights of the Holder of this
Convertible Debenture or the part hereof to be converted, as to such Holder, shall cease and such
Holder shall be treated for all purposes as the record holder of the Common Stock of the Company
issuable upon conversion. As promptly as practicable on or after the conversion date the Company
shall issue a certificate or certificates for the number of full shares of Common Stock issuable
upon conversion, together with, in the event this Convertible Debenture is being converted in part
only, a new Convertible Debenture representing the principal amount hereof which shall not have
been converted.

          (f) If this Convertible Debenture is designated for payment or prepayment by either the Payor
(and the Holder does not elect to convert) or the Holder (and payment hereof is made or provided
for on the proposed payment or prepayment date), any amount designated for payment or prepayment
under the Convertible Debenture shall not be convertible as to such amount so to be paid or prepaid
on or after the proposed payment or prepayment date.

          (g) No fractional shares of Common Stock shall be issued upon conversion of this Convertible
Debenture, but, instead of any fraction of a share that would otherwise be issuable, Payor shall
pay a cash adjustment in respect of such fraction in amount equal to the same fraction of the cash
value as of the date of conversion determined on the basis of the conversion price. At the option
of the Holder, Holder can elect to acquire whole shares instead of any fraction of a share that
would otherwise be issuable by paying Payor a cash adjustment in respect of such fraction in amount
equal to conversion price less the same fraction of the cash value as of the date of conversion
determined on the basis of the conversion price.

          (h) In case any time:

     (1) the Company shall declare any cash dividend on its Common Stock at a rate
in excess of the rate of the last cash dividend theretofore paid;

     (2) the Company shall pay any dividend payable in stock upon its Common Stock
or make any distribution (other than regular cash dividends) to the holders of its
Common Stock;

     (3) the Company shall offer for subscription pro rata to the holders of its
Common Stock any additional shares of stock of any class or other rights;

     (4) there shall be any capital reorganization, or reclassification of the
capital stock of the Company, or consolidation or merger of the Company with, or
sale of all or substantially all of its assets to, another corporation; or

     (5) there shall be a voluntary or involuntary dissolution, liquidation or
winding up of the Company;

then, in any one or more of said cases, the Company shall give written notice, by
first-class mail, postage prepaid, addressed to the registered Holder of this
Convertible Debenture at the address of such Holder as shown on the books of the
Company, of the date on which (aa) the books of the Company shall close or a record
shall be taken for such dividend, distribution or subscription rights, or (bb)

6

 

such reorganization, reclassification, consolidation, merger, sale, dissolution,
liquidation or winding up shall take place, as the case may be. Such notice shall
also specify the date as of which the holders of Common Stock of record shall
participate in such dividend, distribution or subscription rights, or shall be
entitled to exchange their Common Stock for securities or other property deliverable
upon such reorganization, reclassification, consolidation, merger, sale,
dissolution, liquidation or winding up, as the case may be. Such written notice
shall be given at least 30 days prior to the action in question and not less than 30
days prior to the record date or the date on which the Company’s transfer books are
closed in respect thereto.

               (i) As used herein, the term “Common Stock” shall mean and include the Company’s presently
authorized Common Stock and shall also include any capital stock of any class of the Company
hereafter authorized which shall not be limited to a fixed sum or percentage in respect of the
rights of the holders thereof to participate in dividends or in the distribution of assets upon the
voluntary or involuntary liquidation, dissolution or winding up of the Company; provided that the
shares issuable upon conversion of this Convertible Debenture shall include shares designated as
Common Stock of the Company on the date of original issue of this Convertible Debenture.

	 	4.	 	Limitations Upon Capital Reorganization of Common Stock, Consolidation or
Merger.

               (a) No merger or acquisition of the Company or sale of substantially all of its assets, or a
capital reorganization or reclassification of the capital stock of the Company or a voluntary
dissolution, liquidation or bankruptcy filing shall occur absent the written concurrence of Holder.

               (b) In the event that the Holder consents in writing to a merger or acquisition of the Company
or sale of substantially all of its assets, or a capital reorganization or reclassification of the
capital stock of the Company, the following shall then apply:

	 	(i)	 	Right to Receive Additional Shares

If any capital reorganization or reclassification of the capital
stock of the Company, or consolidation or merger of the Company with
another corporation, or the sale of all or substantially all of its
assets to another corporation shall be effected in such a way that
holders of Common Stock shall be entitled to receive stock,
securities or assets with respect to or in exchange for Common Stock,
then, as a condition of such reorganization, reclassification,
consolidation, merger or sale, lawful and adequate provision shall be
made whereby the Holder hereof shall thereafter have the right to
purchase and receive, upon the basis and upon the terms and
conditions specified in this Convertible Debenture and in lieu of the shares of the Common Stock of the Company immediately theretofore
receivable upon conversion hereof, such shares of

7

 

stock, securities or assets as may be issued or payable with respect
to or in exchange for a number of outstanding shares of such Common
Stock equal to the number of shares of such stock immediately
theretofore receivable upon conversion hereof had such
reorganization, reclassification, consolidation, merger or sale not
taken place, and in any such case appropriate provision shall be made
with respect to the rights and interests of the holder of this
Convertible Debenture to the end that the provisions hereof
(including without limitation provisions for adjustments of the
conversion price and of the number of shares issuable upon the
conversion of this Convertible Debenture) shall thereafter be
applicable, as nearly as may be, in relation to any shares of stock,
securities or assets thereafter deliverable upon the conversion
hereof. The Company shall not effect any such consolidation, merger
or sale, unless prior to the consummation thereof the successor
corporation (if other than the Company) resulting from such
consolidation or merger or the corporation purchasing such assets
shall assume, by written instrument executed and mailed to the
registered Holder hereof at the last address of such Holder appearing
on the books of the Company, the obligation to deliver to such Holder
such shares of stock, securities or assets as, in accordance with the
foregoing provisions, such Holder may be entitled to receive.

     5. Reporting Obligations of the Payor.

     As long as all or any portion of the unpaid balance of principal and all accrued and unpaid
interest on this Convertible Debenture remains outstanding, the Company shall deliver to Holder all
unaudited quarterly and annual financial reports and all audited annual financial reports
reflecting the financial results of the Company and copies of the minutes of all Board of Directors
and Shareholders’ meetings together with the written resolutions and other documentation evidencing
all corporate actions. Holder shall have the right to examine all records of the Company, except
with respect to trade secrets and similar confidential information, with reasonable notice, at any
time during normal business hours, and, upon written request of Holder, the Company shall promptly
provide to Holder a written summary describing the contents of any trade secret or other similar
confidential information not made available to the Holder in sufficient detail as to facilitate
informed decision-making. Except as otherwise required by laws or regulations applicable to the
Holder, the Holder shall maintain, and shall require its representatives to maintain, all
information obtained pursuant to this paragraph 5 on a confidential basis.

     6. Costs of Collection.

     If the principal and interest on this Convertible Debenture is not paid when due, and this
Convertible Debenture has not converted pursuant to the terms contained herein, whether or not
collection is initiated by the prosecution of any suit, or by any other judicial proceeding, or
this Convertible Debenture is placed in the hands of an attorney for collection, Payor will pay, in

8

 

addition to all other amounts owing hereunder, all court costs and reasonable attorney’s fees
incurred by the Holder in connection therewith.

     7. Insolvency or Bankruptcy.

     The entire unpaid principal sum of this Convertible Debenture, together with accrued and
unpaid interest thereon, will become immediately due and payable upon the insolvency of the Payor,
the execution by the Payor of a general assignment for the benefit of creditors, the filing by or
against the Payor of a petition in bankruptcy or any petition for relief under the federal
bankruptcy act or the continuation of such petition without dismissal for a period of ninety (90)
days or more, or the appointment of a receiver or trustee to take possession of the property or
assets of Payor.

     8. Waiver of Presentment.

     Payor hereby waives presentment for payment, notice of nonpayment, protest, notice of protest
and all other notices, filing of suit and diligence in collecting the amounts due under this
Convertible Debenture and agrees that the Holder shall not be required first to initiate any suit
or exhaust its remedies against any other person or parties in order to enforce payment of this
Convertible Debenture.

     9. Method and Application of Payments.

     Unless converted pursuant to the terms contained herein, payment of the Principal Balance,
together with any accrued and unpaid interest will be made by check delivered to the Holder at the
address furnished to Payor for that purpose or by wire transfer pursuant to instructions by the
Holder; provided, however, that, at Payor’s option, Payor may make payments of quarterly
installments of accrued interest in shares of Payor’s Common Stock, which shall be valued at $1.00
per share of Common Stock for such purposes. All payments will be applied first to costs of
collection, if any, then to accrued and unpaid interest, and thereafter to principal.

     10. Applicable Law.

     This Convertible Debenture be governed by and construed in accordance with the laws of the
State of Minnesota.

     11. Assignment.

     This Convertible Debenture may only be assigned or transferred by the Holder upon the consent
of Payor.

	 	 	 	 	 	 	 
	     Dated: September 7, 2005	 	WIRELESS RONIN® TECHNOLOGIES, INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Jeffrey Mack
 

Jeffrey Mack
	 	 
	 

	 	 	 	Chief Executive Officer	 	 

9

 

THIS CONVERTIBLE DEBENTURE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR
APPLICABLE STATE SECURITIES LAWS. NO SALE OR DISPOSITION MAY BE EFFECTED EXCEPT IN COMPLIANCE WITH
AN EFFECTIVE REGISTRATION STATEMENT RELATED THERETO OR AN OPINION OF COUNSEL FOR THE HOLDER,
SATISFACTORY TO PAYOR, THAT SUCH REGISTRATION IS NOT REQUIRED UNDER THE ACT.

	 	 	 
	$2,000,000
	 	January 5, 2005

Eden Prairie, Minnesota

CONVERTIBLE DEBENTURE

10% INTEREST ONLY

FIVE YEAR TERM

     For value received, WIRELESS RONIN® TECHNOLOGIES, INC. (“Payor” or “Company”) promises to pay
to the Spirit Lake Tribe, a federally recognized Native American Indian Tribe (“Holder”), at such
place as the Holder may from time to time designate to Payor, the principal sum of TWO MILLION
DOLLARS ($2,000,000), together with all accrued and unpaid interest thereon as set forth below.

     Interest on the unpaid principal balance of this Convertible Debenture (the “Principal
Balance”) will accrue at the rate of ten percent (10%) per annum commencing on the date hereof and
continuing until this Convertible Debenture is fully paid (computed on the basis of a 360 day year,
30 day month), and will be payable in quarterly installments in arrears as set forth below. If not
sooner converted as provided below, the entire unpaid balance of principal and all accrued and
unpaid interest will be due and payable on December 31, 2009
(the “Maturity Date”). Payment of the
accrued interest shall be made by Payor in quarterly installments in the amount of $50,000 on the
last day of March, June, September and December in each year, commencing on March 31, 2005, until
the principal hereof shall have been paid in full. The principal of and interest on this
Convertible Debenture shall be paid in lawful money of the United States.

     This Convertible Debenture is convertible in whole or in part into fully paid and
nonassessable shares of Common Stock of the Company that represent up to twenty percent (20%) of
the Fully Diluted Outstanding Shares of Common Stock of the Company After Conversion, as that term
is hereinafter defined, at any time prior to its payment at the option of the Holder hereof.

     The Holder of this Convertible Debenture is only required to forego the right to receive
repayment of each dollar of the original principal amount of the Convertible Debenture that the
Holder elects to convert into fully paid and nonassessable shares of Common Stock of the Company
and is not required to pay any additional monies or consideration as a condition precedent to
exercising the right to convert.

     This Convertible Debenture has been issued under the terms and provisions of the Convertible
Debenture Purchase Agreement, dated January 5, 2005 (the “Agreement”) between the Payor Wireless
Ronin® Technologies, Inc. and the Holder Spirit Lake Tribe.

 

 

     Upon the occurrence of any one or more of the Events of Default specified in the Agreement,
all amounts then remaining unpaid on this Convertible Debenture, including accrued interest, may be
declared to be or shall become immediately due and payable as provided in the Agreement.

     This Convertible Debenture is subject to the following terms and conditions.

	 	1.	 	Prepayment — Payor Option.

     (a) This Convertible Debenture may be prepaid in whole (but not in part) at any time after
December 31, 2005 at the option of the Payor. Any call for prepayment of this Convertible Debenture
shall be made by giving written notice to the Holder hereof not less than six (6) months prior to
the date fixed by the Payor for prepayment of this Convertible Debenture (the “Prepayment Date”).
Notice of call for prepayment having been given as aforesaid, the outstanding principal amount of
this Convertible Debenture together with unpaid interest accrued thereon to the Prepayment Date,
shall become due and payable on the Prepayment Date. From and after the Prepayment Date, unless the
Payor shall default in such prepayment, interest shall cease to accrue on the principal amount to
be prepaid.

     (b) Nothing hereinabove set forth shall affect in any way the right of the Holder of this
Convertible Debenture to covert this Convertible Debenture into fully paid and nonassessable shares
of Common Stock of Wireless Ronin® Technologies, Inc. at any time and from time to time in
accordance with paragraph 3 hereof.

	 	2.	 	Prepayment— Convertible Debenture Holder Option.

     (a) The Holder of this Convertible Debenture may require that this Convertible Debenture be
prepaid by the Payor in whole (but not in part) upon (i) the sale, lease, license or other
disposition of all or substantially all of the Company’s assets (other than in the ordinary course
of the Company’s business), (ii) the merger or consolidation of the Company into or with another
corporation or the merger or consolidation of any other corporation into or with the Company or a
plan of exchange between the Company and any other corporation (in which consolidation or merger or
plan of exchange any stockholders of the Company receive distributions of cash or securities or
other property). The Company shall give the Holder of this Convertible Debenture written notice of
such impending transaction not later than 60 days prior to the stockholders’ meeting of the Company
called to approve such transaction, or 60 days prior to the closing of such transaction, whichever
is earlier, and shall also notify such Holder in writing of the final approval of such transaction.
The first of such notices shall give the proposed effective date of the transaction (the “Effective
Date”) and shall describe the material terms and conditions of the transaction and of this
paragraph 2(a) (including, without limiting the generality of the foregoing, a description of the
value of the consideration, if any, being offered to the holders of the outstanding securities of
the Company), and the Company shall thereafter give such Holder prompt notice of any material
changes to such terms and conditions. The transaction shall in no event take place sooner than 60
days after the mailing by the Company of the first notice provided for herein or sooner than 20
days after the mailing by the Company of any notice of material changes provided for herein,
whichever is later in time. Any election for prepayment of this Convertible Debenture shall be made
by the Holder of this Convertible Debenture giving

2

 

written notice thereof to the Company at least two days before the Effective Date. If no such
notice is given, the provisions of paragraph 4(b)(i) shall apply. Notice of election of prepayment
by the Holder of this Convertible Debenture having been given as aforesaid, the outstanding
principal amount to be prepaid together with unpaid interest accrued thereon to the Effective Date,
shall become due and payable on the Effective Date. From and after the Effective Date, unless the
Company shall default in such prepayment, interest shall cease to accrue on the principal amount to
be prepaid.

     (b) Nothing hereinabove set forth shall affect in any way the right of the Holder of this
Convertible Debenture to convert this Convertible Debenture into fully paid and nonassessable
shares of Common Stock of Wireless Ronin® Technologies, Inc. at any time and from time to time in
accordance with paragraph 3 hereof.

	 	3.	 	Conversion Rights.

     (a) This Convertible Debenture is convertible in whole at any time prior to its payment at the
option of the Holder into fully paid and nonassessable shares of Common Stock of the Company
constituting twenty percent (20%) of all classes of the Common Stock of the Company on a fully
diluted basis, as further explained below in paragraph 3(b). In addition, as further explained
below in paragraph 3(b), this Convertible Debenture is convertible in part at any time prior to its
payment at the option of the Holder into fully paid and nonassessable shares of Common Stock of the
Company constituting a proportionate percentage of twenty percent (20%) of all classes of the
Common Stock of the Company on a fully diluted basis in the ratio that the amount of the
Convertible Debenture being converted bears to the total amount of the Convertible Debenture
acquired by the Holder. Under no circumstances shall paragraph 3(b) of this Convertible Debenture
be read to entitle the Holders to shares of Common Stock of the Company constituting less than 20%
of all classes of the Common Stock of the Company on a fully diluted basis upon conversion in full
of this Convertible Debenture.

     (b) The following definitions shall apply for purposes of determining the number of fully paid
and nonassessable shares of Common Stock of the Company that this Convertible Debenture is
convertible into in whole or in part at any time prior to its payment at the option of the Holder
hereof.

	 	(i)	 	Definitions

	 	(A)	 	Conversion Dollar Amount. The “Conversion
Dollar Amount” shall be the amount of par value dollars measured by the
original principal amount of the Convertible Debenture that the Holder
elects to convert into fully paid and nonassessable shares of Common
Stock of the Company.
	 
	 	(B)	 	Percentage of the Par Value of Convertible
Debenture Converted. The “Percentage of the Par Value of Convertible
Debenture Converted” shall be equal to the percentage resulting from
dividing the Conversion Dollar Amount by the original principal amount
of the Convertible Debenture.

3

 

	 	(C)	 	Maximum Percentage of Outstanding Shares That
Can Be Acquired. The “Maximum Percentage of Outstanding Shares That Can
Be Acquired” is 20%.
	 
	 	(D)	 	Conversion Ratio. The “Conversion Ratio” shall
be equal to Percentage of the Par Value of Convertible Debenture
Converted times the Maximum Percentage of Outstanding Shares That Can
Be Acquired.
	 
	 	(E)	 	Fully Diluted Outstanding Shares of Common
Stock of the Company. The “Fully Diluted Outstanding Shares of Common
Stock of the Company” shall be the aggregate as of the date of
conversion of (i) the total Outstanding Shares of Common Stock, (ii)
all shares of Common Stock of the Company issuable upon conversion or
exercise in full of all outstanding options, warrants or other
convertible securities or other rights of any nature to acquire shares
of Common Stock or securities convertible into shares of Common Stock
and (iii) all shares of Common Stock that can be acquired as per the
terms of warrants and options that are issued to employees pursuant to
existing employment contracts (to the extent such shares were not
included in (ii)).
	 
	 	(F)	 	Fully Diluted Outstanding Shares of Common
Stock of the Company After Conversion. The “Fully Diluted Outstanding
Shares of Common Stock of the Company After Conversion” shall be
determined as of the date of conversion by dividing the Fully Diluted
Outstanding Shares of Common Stock of the Company by (1-Conversion
Ratio).
	 
	 	(G)	 	Outstanding Shares of Common Stock. The
“Outstanding Shares of Common Stock” shall include all issued and
outstanding shares of Common Stock of the Company.

     (c) Each dollar of the original principal amount of the Convertible Debenture is convertible
into fully paid and nonassessable shares of Common Stock of the Company in whole or in part at any
time prior to its payment at the option of the Holder. The number of fully paid and nonassessable
shares of Common Stock of the Company issuable upon full or partial conversion of this Convertible
Debenture is determined as of the date of conversion by first computing the number of the Fully
Diluted Outstanding Shares of Common Stock of the Company. The Conversion Ratio is then determined
by reference to the percentage that the total Conversion Dollar Amount represents of the total
$2,000,000 original principal amount of the Convertible Debenture. The number of fully paid and
nonassessable shares of Common Stock of the Company issuable upon full or partial conversion of
this Convertible Debenture is then determined as of the date of conversion by subtracting the Fully
Diluted Outstanding Shares of Common Stock of the Company from the Fully Diluted Outstanding Shares
of Common Stock of the Company After Conversion. Under no circumstances shall the number of shares
of Common Stock of the Company issued to the Holder upon conversion of this Convertible Debenture,
when

4

 

added to any shares of Common Stock of the Company issued to the Holder upon prior partial
conversions of this Convertible Debenture, represent more than 20% of the Fully Diluted Shares of
Common Stock of the Company After Conversion (when calculated after each conversion).

     (d) The foregoing computation of the number of shares of fully paid and nonassessable shares
of Common Stock of the Company that this Convertible Debenture can be converted into can be
illustrated as follows. Assuming at the date of conversion there are 12,000,000 and the Holder
elects to convert the entire $2,000,000 of the Convertible Debenture into Common Stock, the
Conversion Ratio would then be 20% (100% x 20%- Percentage of the Par Value of Convertible
Debenture Converted times the Maximum Percentage of Outstanding Shares That Can Be Acquired), the
Fully Diluted Outstanding Shares of Common Stock of the Company After Conversion would be
15,000,000 (12,000,000 / (1-20%)) and the number of shares of Common Stock to be issued upon
conversion would be 3,000,000 (15,000,000-12,000,000) which represents 20% of Fully Diluted
Outstanding Shares of Common Stock of the Company After Conversion.

     (e) In order to exercise the conversion privilege, the Holder hereof shall surrender this
Convertible Debenture to the Company at its principal office, accompanied by written notice to the
Company that the Holder elects to convert this Convertible Debenture or a part hereof. This
Convertible Debenture or the part hereof to be converted shall be deemed to have been converted on
the day of surrender of this Convertible Debenture for conversion in accordance with the foregoing
provisions, and at such time the rights of the Holder of this Convertible Debenture or the part
hereof to be converted, as to such Holder, shall cease and such Holder shall be treated for all
purposes as the record holder of the Common Stock of the Company issuable upon conversion. As
promptly as practicable on or after the conversion date the Company shall issue a certificate or
certificates for the number of full shares of Common Stock issuable upon conversion, together with,
in the event this Convertible Debenture is being converted in part only, a new Convertible
Debenture representing the principal amount hereof which shall not have been converted.

     (f) If this Convertible Debenture is designated for payment or prepayment by either the Payor
(and the Holder does not elect to convert) or the Holder (and payment hereof is made or provided
for on the proposed payment or prepayment date), any amount designated for payment or prepayment
under the Convertible Debenture shall not be convertible as to such amount so to be paid or prepaid
on or after the proposed payment or prepayment date.

     (g) No fractional shares of Common Stock shall be issued upon conversion of this Convertible
Debenture, but, instead of any fraction of a share that would otherwise be issuable, Payor shall
pay a cash adjustment in respect of such fraction in amount equal to the same fraction of the cash
value as of the date of conversion determined on the basis of the conversion price. At the option
of the Holder, Holder can elect to acquire whole shares instead of any fraction of a share that
would otherwise be issuable by paying Payor a cash adjustment in respect of such fraction in amount
equal to conversion price less the same fraction of the cash value as of the date of conversion
determined on the basis of the conversion price.

5

 

     (h) In case any time:

     (1) the Company shall declare any cash dividend on its Common Stock at a rate in excess
of the rate of the last cash dividend theretofore paid;

     (2) the Company shall pay any dividend payable in stock upon its Common Stock or make
any distribution (other than regular cash dividends) to the holders of its Common Stock;

     (3) the Company shall offer for subscription pro rata to the holders of its Common
Stock any additional shares of stock of any class or other rights;

     (4) there shall be any capital reorganization, or reclassification of the capital stock
of the Company, or consolidation or merger of the Company with, or sale of all or
substantially all of its assets to, another corporation; or

     (5) there shall be a voluntary or involuntary dissolution, liquidation or winding up of
the Company;

then, in any one or more of said cases, the Company shall give written notice, by
first-class mail, postage prepaid, addressed to the registered Holder of this Convertible
Debenture at the address of such Holder as shown on the books of the Company, of the date on
which (aa) the books of the Company shall close or a record shall be taken for such
dividend, distribution or subscription rights, or (bb) such reorganization,
reclassification, consolidation, merger, sale, dissolution, liquidation or winding up shall
take place, as the case may be. Such notice shall also specify the date as of which the
holders of Common Stock of record shall participate in such dividend, distribution or
subscription rights, or shall be entitled to exchange their Common Stock for securities or
other property deliverable upon such reorganization, reclassification, consolidation,
merger, sale, dissolution, liquidation or winding up, as the case may be. Such written
notice shall be given at least 30 days prior to the action in question and not less than 30
days prior to the record date or the date on which the Company’s transfer books are closed
in respect thereto.

     (i) As used herein, the term “Common Stock” shall mean and include the Company’s presently
authorized Common Stock and shall also include any capital stock of any class of the Company
hereafter authorized which shall not be limited to a fixed sum or percentage in respect of the
rights of the holders thereof to participate in dividends or in the distribution of assets upon the
voluntary or involuntary liquidation, dissolution or winding up of the Company; provided that the
shares issuable upon conversion of this Convertible Debenture shall include shares designated as
Common Stack of the Company on the date of original issue of this Convertible Debenture.

6

 

	 	4.	 	Limitations Upon Capital Reorganization of Common Stock, Consolidation or
Merger.

     (a) No merger or acquisition of the Company or sale of substantially all of its assets, or a
capital reorganization or reclassification of the capital stock of the Company or a voluntary
dissolution, liquidation or bankruptcy filing shall occur absent the written concurrence of Holder.

     (b) In the event that the Holder consents in writing to a merger or acquisition of the Company
or sale of substantially all of its assets, or a capital reorganization or reclassification of the
capital stock of the Company, the following shall then apply:

	 	(i)	 	Right to Receive Additional Shares

If any capital reorganization or reclassification of the capital stock of
the Company, or consolidation or merger of the Company with another
corporation, or the sale of all or substantially all of its assets to
another corporation shall be effected in such a way that holders of Common
Stock shall be entitled to receive stock, securities or assets with respect
to or in exchange for Common Stock, then, as a condition of such
reorganization, reclassification, consolidation, merger or sale, lawful and
adequate provision shall be made whereby the Holder hereof shall thereafter
have the right to purchase and receive, upon the basis and upon the terms
and conditions specified in this Convertible Debenture and in lieu of the shares of the Common Stock of the Company immediately theretofore receivable
upon conversion hereof, such shares of stock, securities or assets as may be
issued or payable with respect to or in exchange for a number of outstanding shares of such Common Stock equal to the number of shares of such stock
immediately theretofore receivable upon conversion hereof had such reorganization, reclassification, consolidation, merger or sale not taken
place, and in any such case appropriate provision shall be made with respect
to the rights and interests of the holder of this Convertible Debenture to
the end that the provisions hereof (including without limitation provisions
for adjustments of the conversion price and of the number of shares issuable
upon the conversion of this Convertible Debenture) shall thereafter be
applicable, as nearly as may be, in relation to any shares of stock,
securities or assets thereafter deliverable upon the conversion hereof. The
Company shall not effect any such consolidation, merger or sale, unless
prior to the consummation thereof the successor corporation (if other than
the Company) resulting from such consolidation or merger or the corporation
purchasing such assets shall assume, by written instrument executed and
mailed to the registered Holder hereof at the last address of such Holder
appearing on the books of the Company, the obligation to deliver to such
Holder such shares of stock, securities or assets as, in accordance with the
foregoing provisions, such Holder may be entitled to receive.

7

 

	 	5.	 	Reporting Obligations of the Payor.

     As long as all or any portion of the unpaid balance of principal and all accrued and unpaid
interest on this Convertible Debenture remains outstanding, the Company shall deliver to Holder all
unaudited quarterly and annual financial reports and all audited annual financial reports
reflecting the financial results of the Company and copies of the minutes of all Board of Directors
and Shareholders’ meetings together with the written resolutions and other documentation evidencing
all corporate actions. Holder shall have the right to examine all records of the Company, except
with respect to trade secrets and similar confidential information, with reasonable notice, at any
time during normal business hours, and, upon written request of Holder, the Company shall promptly
provide to Holder a written summary describing the contents of any trade secret or other similar
confidential information not made available to the Holder in sufficient detail as to facilitate
informed decision-making. Except as otherwise required by laws or regulations applicable to the
Holder, the Holder shall maintain, and shall require its representatives to maintain, all
information obtained pursuant to this paragraph 5 on a confidential basis.

	 	6.	 	Costs of Collection.

     If the principal and interest on this Convertible Debenture is not paid when due, and this
Convertible Debenture has not converted pursuant to the terms contained herein, whether or not
collection is initiated by the prosecution of any suit, or by any other judicial proceeding, or
this Convertible Debenture is placed in the hands of an attorney for collection, Payor will pay, in
addition to all other amounts owing hereunder, all court costs and reasonable attorney’s fees
incurred by the Holder in connection therewith.

	 	7.	 	Insolvency or Bankruptcy.

     The entire unpaid principal sum of this Convertible Debenture, together with accrued and
unpaid interest thereon, will become immediately due and payable upon the insolvency of the Payor,
the execution by the Payor of a general assignment for the benefit of creditors, the filing by or
against the Payor of a petition in bankruptcy or any petition for relief under the federal
bankruptcy act or the continuation of such petition without dismissal for a period of ninety (90)
days or more, or the appointment of a receiver or trustee to take possession of the property or
assets of Payor.

	 	8.	 	Waiver of Presentment.

     Payor hereby waives presentment for payment, notice of nonpayment, protest, notice of protest
and all other notices, filing of suit and diligence in collecting the amounts due under this
Convertible Debenture and agrees that the Holder shall not be required first to initiate any suit
or exhaust its remedies against any other person or parties in order to enforce payment of this
Convertible Debenture.

	 	9.	 	Method and Application of Payments.

     Unless converted pursuant to the terms contained herein, payment of the Principal Balance,
together with any accrued and unpaid interest will be made by check delivered to the

8

 

Holder at the address furnished to Payor for that purpose or by wire transfer pursuant to
instructions by the Holder. All payments will be applied first to costs of collection, if any, then
to accrued and unpaid interest, and thereafter to principal.

	 	10.	 	Applicable Law.

     This Convertible Debenture be governed by and construed in accordance with the laws of the
State of Minnesota.

	 	11.	 	Assignment.

     This Convertible Debenture may only be assigned or transferred by the Holder upon the consent
of Payor.

	 	 	 	 	 	 	 
	Dated: January 5, 2005

	 	 	 	   WIRELESS RONIN®	 	 
	 

	 	 	 	TECHNOLOGIES, INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	      /s/ Jeffrey Mack
 

Jeffrey Mack
	 	 
	 

	 	 	 	Chief Executive Officer	 	 

9

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