1 Exhibit 10.16 REVOLVING WARRANT THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS, AND ACCORDINGLY, SUCH SECURITIES MAY NOT BE TRANSFERRED, SOLD OR OTHERWISE DISPOSED OF EXCEPT IN COMPLIANCE WITH THE REGISTRATION OR QUALIFICATION PROVISIONS OF APPLICABLE FEDERAL AND STATE SECURITIES LAWS OR UNLESS AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE COMPANY IS OBTAINED TO THE EFFECT THAT SUCH REGISTRATION AND QUALIFICATION IS NOT REQUIRED. Warrant No. R-12 WARRANT to Purchase Shares of Common Stock of STUDENT ADVANTAGE, INC. THIS IS TO CERTIFY THAT RESERVOIR CAPITAL ASSOCIATES L.P., or its registered assigns, is entitled to purchase in whole or in part from STUDENT ADVANTAGE, INC., a Delaware corporation (the "Company"), at any time and from time to time, but not later than 5:00 p.m., New York City time, on June 25, 2005 (the "Expiration Date"), the number of Stock Units (as defined in the Warrant Agreement referred to below) specified below at a purchase price of $0.01 per Stock Unit (the "Exercise Price"); provided, that such purchase price shall not be less than the aggregate par value of the capital stock contained in a Stock Unit, subject to the terms and conditions set forth herein and in the Warrant Agreement, each such purchase of a Stock Unit to be made, and to be deemed effective for the purpose of determining the date of exercise, only upon surrender of this Warrant to the Company at its office referred to in Section 15.03 of the Warrant Agreement, with the Form of Exercise attached hereto (or a reasonable facsimile thereof) duly completed and signed, and upon payment in full to the Company of the Exercise Price (i) in cash or (ii) by certified or official bank check or (iii) by any combination of the foregoing, all as provided in the Warrant Agreement and upon compliance with and subject to the conditions set forth herein and in the Warrant Agreement. The number of Stock Units for which this Warrant is exercisable shall initially be zero but shall be adjusted on the 25th day of each month following the date hereof to equal (i) the number of Stock Units for which it was previously exercisable plus (ii) (A) 43.75 times (B) a fraction (x) the numerator of which is the average daily outstanding balance during such month of the Revolving Loans (as defined under the Loan Agreement) (including accrued interest) and (y) the denominator of which is $5,000,000. The number of Stock Units for which this Warrant 2 -2- shall be exercisable shall not be adjusted from and after the date of termination of the Revolving Loan Commitments (as defined in the Loan Agreement). On or prior to the Expiration Date, this Warrant may be converted, in whole or in part, at the Holder's option, into the number of shares of Common Stock for each Stock Unit evidenced hereby which is being so converted, equal to (a)(i) the product of (x) the number of shares of Common Stock comprising a Stock Unit at the time of such conversion and (y) the Current Market Price per share of Common Stock at the time of such conversion minus (ii) the Exercise Price per Stock Unit at the time of such conversion, divided by (b) the Current Market Price per share of Common Stock at the time of such conversion, all as provided in the Warrant Agreement and upon compliance with and subject to the conditions set forth herein and in the Warrant Agreement. This Warrant is issued under and in accordance with the Warrant Agreement dated as of June 25, 2001 between the Company and certain holders (as the same may be modified and supplemented in accordance with its terms and as in effect from time to time, the "Warrant Agreement"), and is subject to the terms and provisions of the Warrant Agreement, which terms and provisions are hereby incorporated by reference herein and made a part hereof. Every Holder of this Warrant consents to all of the terms contained in the Warrant Agreement by acceptance hereof. The number of shares of Common Stock or other securities of the Company constituting one "Stock Unit" are subject to adjustment in certain events as provided in the Warrant Agreement. The Company shall not be required to issue a fractional share of Common Stock upon exercise of this Warrant. As to any fraction of a share which the Holder hereof would otherwise be entitled to purchase upon such exercise, the Company may pay a cash adjustment in respect of such final fraction in an amount equal to the same fraction of the Current Market Price per share of Common Stock on the date of exercise or may be round up to the next whole number of shares. This Warrant may be exchanged either separately or in combination with other Warrants at the office of the Company referred to in Section 15.03 of the Warrant Agreement for new Warrants representing the same aggregate number of Warrants evidenced by the Warrant or Warrants exchanged, upon surrender of this and any other Warrant being exchanged and upon compliance with and subject to the conditions set forth herein and in the Warrant Agreement. The Warrants and the Warrant Stock shall be transferable only upon compliance with the conditions specified in Sections 4 and 5 of the Warrant Agreement, which conditions are intended, among other things, to ensure compliance with the provisions of the Securities Act in respect of the transfer of any Warrant or any Warrant Stock, and any Holder hereof shall be bound by the provisions of (and entitled to the benefits of) said Sections 4 and 5. Upon any such transfer effected in compliance with said Sections 4 and 5, a new Warrant or new Warrants of different denominations, representing in the aggregate a like number of Warrants, will be issued to the transferee. Every Holder hereof, by accepting this Warrant, consents and 3 -3- agrees with the Company and with every subsequent Holder of this Warrant that until due presentation for the registration of transfer of this Warrant on the Warrant register maintained by the Company, the Company may deem and treat the Person in whose name this Warrant is registered as the absolute and lawful owner for all purposes whatsoever and the Company shall not be affected by any notice to the contrary. Nothing contained in the Warrant Agreement or in this Warrant shall be construed as conferring on the holder of any Warrants or his or her transferee any rights whatsoever as a stockholder of the Company. No provision hereof, in the absence of affirmative action by the Holder hereof to purchase shares of Common Stock, and no mere enumeration herein of the rights or privileges of such Holder, shall give rise to any liability of such Holder for the Exercise Price or as a Stockholder of the Company, whether such liability is asserted by the Company, by any creditor of the Company or any other Person. Any notices and other communications pursuant to the provisions hereof shall be sent in accordance with Section 15.02 of the Warrant Agreement. Each term used herein without definition shall have the meaning assigned thereto in the Warrant Agreement. 4 -4- IN WITNESS WHEREOF, the Company has duly executed this Warrant. Dated: June 25, 2001 STUDENT ADVANTAGE, INC. By: /s/ Raymond V. Sozzi, Jr. ------------------------- Name: Raymond V. Sozzi, Jr. Title: President and Chief Executive Officer 5 FORM OF EXERCISE (To be executed by the registered holder hereof) The undersigned registered owner of this Warrant hereby SELECT ONE OF THE FOLLOWING TWO CHOICES: [irrevocably exercises this Warrant for the purchase of Stock Units of STUDENT ADVANTAGE, INC., a Delaware corporation, and herewith makes payment therefor in the amount of $_____________, all at the price and on the terms and conditions specified in this Warrant,] OR [irrevocably converts this Warrant into shares of Common Stock of STUDENT ADVANTAGE, INC., a Delaware corporation, all in the manner and on the terms and conditions specified in this Warrant,] and requests that (i) certificates and/or other instruments covering such Stock Units be issued in accordance with the instructions given below and (ii) if such Stock Units shall not include all of the Stock Units to which the Holder is entitled under this Warrant, that a new Warrant of like tenor and date for the balance of the Stock Units issuable hereunder be delivered to the undersigned. Dated: ___________, ____ ________________________________ (Signature of Registered Holder) 6 -2- Instructions for issuance and registration of Stock Units: Name of Registered Holder:____________________________________________ (Please print) Social Security or Other Identifying Number:__________________________ Please deliver certificate to the following address: ________________________________ ________________________________ ________________________________ 7 FORM OF ASSIGNMENT FOR VALUE RECEIVED the undersigned registered owner of this Warrant hereby sells, assigns and transfers unto the assignee named below all the rights of the undersigned under this Warrant with respect to the number of Stock Units covered thereby set forth hereinbelow unto: Number of Name of Assignee Address Stock Units - ---------------- ------- ----------- Dated:__________________ _________________________________ Signature of Registered Holder _________________________________ Name of Registered Holder (Please Print) Witness: _______________________________________________________________________________