Document:

EX-10.20

 

Exhibit 10.20

Synacor, Inc.

2007 Employee Stock Purchase Plan

(As Adopted September 17, 2007)

 

 

TABLE OF CONTENTS

	 	 	 	 	 
	 	 	Page	 
	SECTION 1. PURPOSE OF THE PLAN
	 	 	1	 
	 
	 	 	 	 
	SECTION 2. ADMINISTRATION OF THE PLAN
	 	 	1	 
	(a) Committee Composition
	 	 	1	 
	(b) Committee Responsibilities
	 	 	1	 
	 
	 	 	 	 
	SECTION 3. STOCK OFFERED UNDER THE PLAN
	 	 	1	 
	(a) Authorized Shares
	 	 	1	 
	(b) Anti-Dilution Adjustments
	 	 	1	 
	(c) Reorganizations
	 	 	1	 
	 
	 	 	 	 
	SECTION 4. ENROLLMENT AND PARTICIPATION
	 	 	2	 
	(a) Offering Periods
	 	 	2	 
	(c) Enrollment at IPO
	 	 	2	 
	(c) Enrollment After IPO
	 	 	2	 
	(d) Duration of Participation
	 	 	2	 
	 
	 	 	 	 
	SECTION 5. EMPLOYEE CONTRIBUTIONS
	 	 	3	 
	(a) Commencement of Payroll Deductions
	 	 	3	 
	(b) Amount of Payroll Deductions
	 	 	3	 
	(c) Reducing Withholding Rate or Discontinuing Payroll Deductions
	 	 	3	 
	(d) Increasing Withholding Rate
	 	 	3	 
	 
	 	 	 	 
	SECTION 6. WITHDRAWAL FROM THE PLAN
	 	 	3	 
	(a) Withdrawal
	 	 	3	 
	(b) Re-Enrollment After Withdrawal
	 	 	3	 
	 
	 	 	 	 
	SECTION 7. CHANGE IN EMPLOYMENT STATUS
	 	 	4	 
	(a) Termination of Employment
	 	 	4	 
	(b) Leave of Absence
	 	 	4	 
	(c) Death
	 	 	4	 
	 
	 	 	 	 
	SECTION 8. PLAN ACCOUNTS AND PURCHASE OF SHARES
	 	 	4	 
	(a) Plan Accounts
	 	 	4	 
	(b) Purchase Price
	 	 	4	 
	(c) Number of Shares Purchased
	 	 	4	 
	(d) Available Shares Insufficient
	 	 	5	 
	(e) Issuance of Stock
	 	 	5	 
	(f) Tax Withholding
	 	 	5	 
	(g) Unused Cash Balances
	 	 	5	 
	(h) Stockholder Approval
	 	 	5	 

i

 

	 	 	 	 	 
	 	 	 	Page	 
	SECTION 9. LIMITATIONS ON STOCK OWNERSHIP
	 	 	5	 
	(a) Five Percent Limit
	 	 	5	 
	(b) Dollar Limit
	 	 	6	 
	 
	 	 	 	 
	SECTION 10. RIGHTS NOT TRANSFERABLE
	 	 	6	 
	 
	 	 	 	 
	SECTION 11. NO RIGHTS AS AN EMPLOYEE
	 	 	7	 
	 
	 	 	 	 
	SECTION 12. NO RIGHTS AS A STOCKHOLDER
	 	 	7	 
	 
	 	 	 	 
	SECTION 13. MANDATORY HOLDING PERIOD
	 	 	7	 
	 
	 	 	 	 
	SECTION 14. SECURITIES LAW REQUIREMENTS
	 	 	7	 
	 
	 	 	 	 
	SECTION 15. AMENDMENT OR DISCONTINUANCE
	 	 	7	 
	(b) General Rule
	 	 	7	 
	(b) Impact on Purchase Price
	 	 	7	 
	 
	 	 	 	 
	SECTION 16. DEFINITIONS
	 	 	8	 
	(a) Board
	 	 	8	 
	(b) Code
	 	 	8	 
	(c) Committee
	 	 	8	 
	(d) Company
	 	 	8	 
	(e) Compensation
	 	 	8	 
	(f) Corporate Reorganization
	 	 	8	 
	(g) Eligible Employee
	 	 	8	 
	(h) Exchange Act
	 	 	9	 
	(i) Fair Market Value
	 	 	9	 
	(j) IPO
	 	 	9	 
	(k) IPO Date
	 	 	9	 
	(l) Offering Period
	 	 	9	 
	(m) Participant
	 	 	9	 
	(n) Participating Company
	 	 	9	 
	(o) Plan
	 	 	9	 
	(p) Plan Account
	 	 	9	 
	(q) Purchase Price
	 	 	9	 
	(r) Stock
	 	 	9	 
	(s) Subsidiary
	 	 	9	 
	 
	 	 	 	 
	SECTION 16. EXECUTION
	 	 	10	 

ii

 

Synacor, Inc.

2007 Employee Stock Purchase Plan

SECTION 1. PURPOSE OF THE PLAN.

          The Board adopted the Plan effective as of the IPO Date. The purpose of the Plan is to
provide Eligible Employees with an opportunity to increase their proprietary interest in the
success of the Company by purchasing Stock from the Company on favorable terms and to pay for such
purchases through payroll deductions. The Plan is intended to qualify for favorable tax treatment
under section 423 of the Code.

SECTION 2. ADMINISTRATION OF THE PLAN.

          (a) Committee Composition. The Committee shall administer the Plan. The Committee shall
consist exclusively of one or more members of the Board, who shall be appointed by the Board.

          (b) Committee Responsibilities. The Committee shall interpret the Plan and make all other
policy decisions relating to the operation of the Plan. The Committee may adopt such rules,
guidelines and forms as it deems appropriate to implement the Plan. The Committee’s determinations
under the Plan shall be final and binding on all persons.

SECTION 3. STOCK OFFERED UNDER THE PLAN.

          (a) Authorized Shares. The number of shares of Stock available for purchase under the Plan
shall be 250,000 (subject to adjustment pursuant to Subsection (b) below).

          (b) Anti-Dilution Adjustments. The aggregate number of shares of Stock offered under the
Plan, the 1,000-share limitation described in Section 8(c) and the price of shares that any
Participant has elected to purchase shall be adjusted proportionately for any increase or decrease
in the number of outstanding shares of Stock resulting from a subdivision or consolidation of
shares or the payment of a stock dividend, any other increase or decrease in such shares effected
without receipt or payment of consideration by the Company, the distribution of the shares of a
Subsidiary to the Company’s stockholders, or a similar event.

          (c) Reorganizations. Any other provision of the Plan notwithstanding, immediately prior to
the effective time of a Corporate
Reorganization, the Offering Period then in progress shall terminate and shares shall be
purchased pursuant to Section 8, unless the Plan is continued or assumed by the surviving
corporation or its parent corporation. The Plan shall in no event be construed to restrict in any
way the Company’s right to undertake a dissolution, liquidation, merger, consolidation or other
reorganization.

 

 

SECTION 4. ENROLLMENT AND PARTICIPATION.

          (a) Offering Periods. While the Plan is in effect, two Offering Periods shall commence in
each calendar year. The Offering Periods shall consist of the six-month periods commencing on each
May 1 and November 1, except that:

          (i) The first Offering Period under the Plan shall commence on the IPO Date and
shall end on April 30, 2008; and

          (ii) The Committee may determine that the first Offering Period applicable to
the Eligible Employees of a new Participating Company shall commence on any date
specified by the Committee, provided that an Offering Period shall in no event be
longer than 27 months.

          (b) Enrollment at IPO. Each individual who, on the IPO Date, qualifies as an Eligible
Employee shall automatically become a Participant on such day. Each Participant who was
automatically enrolled on the IPO Date shall file the prescribed enrollment form with the Company.
The enrollment form shall be filed at the prescribed location within 10 business days after the
Company filed a registration statement on Form S-8 for the shares of Stock offered under the Plan.
If a Participant who was automatically enrolled on the IPO Date fails to file such form in a timely
manner, then such Participant shall be deemed to have withdrawn from the Plan under Section 6(a).
A former Participant who is deemed to have withdrawn from the Plan shall not be a Participant until
he or she re-enrolls in the Plan under Subsection (c) below. Re-enrollment may be effective only
at the commencement of an Offering Period.

          (c) Enrollment After IPO. In the case of any individual who qualifies as an Eligible Employee
on the first day of any Offering Period other than the first Offering Period, he or she may elect
to become a Participant on such day by filing the prescribed enrollment form with the Company. The
enrollment form shall be filed at the prescribed location at least five business days prior to such
day.

          (d) Duration of Participation. Once enrolled in the Plan, a Participant shall continue to
participate in the Plan until he or she:

          (i) Reaches the end of the Offering Period in which his or her employee
contributions were discontinued under Section 5(c) or 9(b);

          (ii) Is deemed to withdraw from the Plan under Subsection (b) above;

          (iii) Withdraws from the Plan under Section 6(a); or

          (iv) Ceases to be an Eligible Employee.

A Participant whose employee contributions were discontinued automatically under Section 9(b) shall
automatically resume participation at the beginning of the earliest Offering Period ending in the
next calendar year, if he or she then is an Eligible Employee. In all other cases, a former

2

 

Participant may again become a Participant, if he or she then is an Eligible Employee, by following
the procedure described in Subsection (c) above.

SECTION 5. EMPLOYEE CONTRIBUTIONS.

          (a) Commencement of Payroll Deductions. A Participant may purchase shares of Stock under the
Plan solely by means of payroll deductions. Payroll deductions shall commence as soon as
reasonably practicable after the Company has received the prescribed enrollment form.

          (b) Amount of Payroll Deductions. An Eligible Employee shall designate on the prescribed
enrollment form the portion of his or her Compensation that he or she elects to have withheld for
the purchase of Stock. Such portion shall be a whole percentage of the Eligible Employee’s
Compensation, but not less than 1% nor more than 15%.

          (c) Reducing Withholding Rate or Discontinuing Payroll Deductions. If a Participant wishes to
reduce his or her rate of payroll withholding, such Participant may do so by filing a new
enrollment form with the Company at the prescribed location at any time. The new withholding rate
shall be effective as soon as reasonably practicable after the Company has received such form. The
new withholding rate may be 0% or any whole percentage of the Participant’s Compensation, but not
more than his or her old withholding rate. No Participant shall make more than two elections under
this Subsection (c) during any Offering Period. (In addition, employee contributions may be
discontinued automatically pursuant to Section 9(b).)

          (d) Increasing Withholding Rate. If a Participant wishes to increase his or her rate of
payroll withholding, such Participant may do so by filing a new enrollment form with the Company at
the prescribed location at any time. The new withholding rate may be effective on the first day of
any Offering Period, provided that the Participant has filed the enrollment form with the Company
at the prescribed location at least five business days prior to the first day of such Offering
Period. The new withholding rate may be any whole percentage of the Participant’s Compensation,
but not less than 1% nor more than 15%. An increase in a Participant’s rate of payroll withholding
may not take effect during an Offering Period.

SECTION 6. WITHDRAWAL FROM THE PLAN.

          (a) Withdrawal. A Participant may elect to withdraw from the Plan by filing the prescribed
form with the Company at the prescribed location at any time before the last day of an Offering
Period. As soon as reasonably practicable thereafter, payroll deductions shall cease and the
entire amount credited to the Participant’s Plan Account shall be refunded to him or her in cash,
without interest. No partial withdrawals shall be permitted.

          (b) Re-Enrollment After Withdrawal. A former Participant who has withdrawn from the Plan
shall not be a Participant until he or she re-enrolls in the Plan under Section 4(c).
Re-enrollment may be effective only at the commencement of an Offering Period.

3

 

SECTION 7. CHANGE IN EMPLOYMENT STATUS.

          (a) Termination of Employment. Termination of employment as an Eligible Employee for any
reason, including death, shall be treated as an automatic withdrawal from the Plan under
Section 6(a). (A transfer from one Participating Company to another shall not be treated as a
termination of employment.)

          (b) Leave of Absence. For purposes of the Plan, employment shall not be deemed to terminate
when the Participant goes on a military leave, a sick leave or another bona fide leave of absence,
if the leave was approved by the Company in writing. Employment, however, shall be deemed to
terminate 90 days after the Participant goes on a leave, unless a contract or statute guarantees
his or her right to return to work. Employment shall be deemed to terminate in any event when the
approved leave ends, unless the Participant immediately returns to work.

          (c) Death. In the event of the Participant’s death, the amount credited to his or her Plan
Account shall be paid to a beneficiary designated by him or her for this purpose on the prescribed
form or, if none, to the Participant’s estate. Such form shall be valid only if it was filed with
the Company at the prescribed location before the Participant’s death.

SECTION 8. PLAN ACCOUNTS AND PURCHASE OF SHARES.

          (a) Plan Accounts. The Company shall maintain a Plan Account on its books in the name of each
Participant. Whenever an amount is deducted from the Participant’s Compensation under the Plan,
such amount shall be credited to the Participant’s Plan Account. Amounts credited to Plan Accounts
shall not be trust funds and may be commingled with the Company’s general assets and applied to
general corporate purposes. No interest shall be credited to Plan Accounts.

          (b) Purchase Price. The Purchase Price for each share of Stock purchased at the close of an
Offering Period shall be the lower of:

          (i) 85% of the Fair Market Value of such share on the last trading day before
the commencement of such Offering Period or, in the case of the first Offering
Period under the Plan, 85% of the price at which one share of Stock is offered to
the public in the IPO; or

          (ii) 85% of the Fair Market Value of such share on the last trading day in such
Offering Period.

          (c) Number of Shares Purchased. As of the last day of each Offering Period, each Participant
shall be deemed to have elected to purchase the number of shares of Stock calculated in accordance
with this Subsection (c), unless the Participant has previously elected to withdraw from the Plan
in accordance with Section 6(a). The amount then in the Participant’s Plan Account shall be
divided by the Purchase Price, and the number of shares that results shall be purchased from the
Company with the funds in the Participant’s Plan Account. The foregoing notwithstanding, no
Participant shall purchase more than 1,000 shares of Stock

4

 

with respect to any Offering Period nor
more than the amounts of Stock set forth in Sections 3(a) and 9(b). The Committee may determine
with respect to all Participants that any fractional share, as calculated under this
Subsection (c), shall be (i) rounded down to the next lower whole share or (ii) credited as a
fractional share.

          (d) Available Shares Insufficient. In the event that the aggregate number of shares that all
Participants elect to purchase during an Offering Period exceeds the maximum number of shares
remaining available for issuance under Section 3, then the number of shares to which each
Participant is entitled shall be determined by multiplying the number of shares available for
issuance by a fraction. The numerator of such fraction is the number of shares that such
Participant has elected to purchase, and the denominator of such fraction is the number of shares
that all Participants have elected to purchase.

          (e) Issuance of Stock. The shares of Stock purchased by a Participant under the Plan may be
registered in the name of such Participant, or jointly in the name of such Participant and his or
her spouse as joint tenants with the right of survivorship or as community property (with or
without the right of survivorship). The Committee may require that such shares must be held for
the Participant’s benefit by a broker designated by the Committee until the expiration of the
holding period described in section 423(a)(1) of the Code. (The preceding sentence shall apply
whether or not the Participant is required to pay income tax in the United States.)

          (f) Tax Withholding. To the extent required by applicable federal, state, local or foreign
law, a Participant shall make arrangements satisfactory to the Company for the satisfaction of any
withholding tax obligations that arise in connection with the Plan. The Company shall not be
required to issue any shares of Stock under the Plan until such obligations are satisfied.

          (g) Unused Cash Balances. An amount remaining in the Participant’s Plan Account that
represents the Purchase Price for any fractional share shall be carried over in the Participant’s
Plan Account to the next Offering Period. Any amount remaining in the Participant’s Plan Account
that represents the Purchase Price for whole shares that could not be purchased by reason of
Subsection (c) above, Section 3 or Section 9(b) shall be refunded to the Participant in cash,
without interest.

          (h) Stockholder Approval. Any other provision of the Plan notwithstanding, no shares of Stock
shall be purchased under the Plan unless and until the Company’s stockholders have approved the
adoption of the Plan.

SECTION 9. LIMITATIONS ON STOCK OWNERSHIP.

          (a) Five Percent Limit. Any other provision of the Plan notwithstanding, no Participant shall
be granted a right to purchase Stock under the Plan if such Participant, immediately after his or
her election to purchase such Stock, would own stock possessing more than 5% of the total combined
voting power or value of all classes of stock of the Company or any parent or Subsidiary of the
Company. For purposes of this Subsection (a), the following rules shall apply:

5

 

          (i) Ownership of stock shall be determined after applying the attribution rules
of section 424(d) of the Code;

          (ii) Each Participant shall be deemed to own any stock that he or she has a
right or option to purchase under this or any other plan; and

          (iii) Each Participant shall be deemed to have the right to purchase 1,000
shares of Stock under this Plan with respect to each Offering Period.

          (b) Dollar Limit. Any other provision of the Plan notwithstanding, no Participant shall
purchase Stock with a Fair Market Value in excess of the following limit:

          (i) In the case of Stock purchased during an Offering Period that commenced in
the current calendar year, the limit shall be equal to (A) $25,000 minus (B) the
Fair Market Value of the Stock that the Participant previously purchased in the
current calendar year (under this Plan and all other employee stock purchase plans
of the Company or any parent or Subsidiary of the Company).

          (ii) In the case of Stock purchased during an Offering Period that commenced in
the immediately preceding calendar year, the limit shall be equal to (A) $50,000
minus (B) the Fair Market Value of the Stock that the Participant previously
purchased (under this Plan and all other employee stock
purchase plans of the Company or any parent or Subsidiary of the Company) in
the current calendar year and in the immediately preceding calendar year.

For purposes of this Subsection (b), the Fair Market Value of Stock shall be determined in each
case as of the beginning of the Offering Period in which such Stock is purchased. Employee stock
purchase plans not described in section 423 of the Code shall be disregarded. If a Participant is
precluded by this Subsection (b) from purchasing additional Stock under the Plan, then his or her
employee contributions shall automatically be discontinued and shall automatically resume at the
beginning of the earliest Offering Period ending in the next calendar year (if he or she then is an
Eligible Employee).

SECTION 10. RIGHTS NOT TRANSFERABLE.

          The rights of any Participant under the Plan, or any Participant’s interest in any Stock or
moneys to which he or she may be entitled under the Plan, shall not be transferable by voluntary or
involuntary assignment or by operation of law, or in any other manner other than by beneficiary
designation or the laws of descent and distribution. If a Participant in any manner attempts to
transfer, assign or otherwise encumber his or her rights or interest under the Plan, other than by
beneficiary designation or the laws of descent and distribution, then such act shall be treated as
an election by the Participant to withdraw from the Plan under Section 6(a).

6

 

SECTION 11. NO RIGHTS AS AN EMPLOYEE.

          Nothing in the Plan or in any right granted under the Plan shall confer upon the Participant
any right to continue in the employ of a Participating Company for any period of specific duration
or interfere with or otherwise restrict in any way the rights of the Participating Companies or of
the Participant, which rights are hereby expressly reserved by each, to terminate his or her
employment at any time and for any reason, with or without cause.

SECTION 12. NO RIGHTS AS A STOCKHOLDER.

          A Participant shall have no rights as a stockholder with respect to any shares of Stock that
he or she may have a right to purchase under the Plan until such shares have been purchased on the
last day of the applicable Offering Period.

SECTION 13. MANDATORY HOLDING PERIOD

          Any shares of Stock purchased under the Plan may not be sold until the date that is at least
six (6) months following the date on which such shares were purchased.

SECTION 14. SECURITIES LAW REQUIREMENTS.

          Shares of Stock shall not be issued under the Plan unless the issuance and delivery of such
shares comply with (or are exempt from) all applicable requirements of law, including (without
limitation) the Securities Act of 1933, as amended, the rules and regulations promulgated
thereunder, state securities laws and regulations, and the regulations of any stock exchange or
other securities market on which the Company’s securities may then be traded.

SECTION 15. AMENDMENT OR DISCONTINUANCE.

          (a) General Rule. The Board shall have the right to amend, suspend or terminate the Plan at
any time and without notice. Except as provided in Section 3, any increase in the aggregate number
of shares of Stock that may be issued under the Plan shall be subject to the approval of the
Company’s stockholders. In addition, any other amendment of the Plan shall be subject to the
approval of the Company’s stockholders to the extent required by any applicable law or regulation.
The Plan shall terminate automatically 20 years after its adoption by the Board, unless (a) the
Plan is extended by the Board and (b) the extension is approved within 12 months by a vote of the
stockholders of the Company.

          (b) Impact on Purchase Price. This Subsection (b) shall apply in the event that (i) the
Company’s stockholders during an Offering Period approve an increase in the number of shares of
Stock that may be issued under Section 3 and (ii) the aggregate number of shares to be purchased at
the close of such Offering Period exceeds the number of shares that remained available under
Section 3 before such increase. In such event, the Purchase Price for each share of Stock
purchased at the close of such Offering Period shall be the lower of:

7

 

          (i) The higher of (A) 85% of the Fair Market Value of such share on the last
trading day before the commencement of the applicable Offering Period or, in the
case of the first Offering Period under the Plan, 85% of the price at which one
share of Stock is offered to the public in the IPO or (B) 85% of the Fair Market
Value of such share on the last trading day before the date when the Company’s
stockholders approve such increase; or

          (ii) 85% of the Fair Market Value of such share on the last trading day in such
Offering Period.

SECTION 16. DEFINITIONS.

          (a) “Board” means the Board of Directors of the Company, as constituted from time to time.

          (b) “Code” means the Internal Revenue Code of 1986, as amended.

          (c) “Committee” means a committee of the Board, as described in Section 2.

          (d) “Company” means Synacor, Inc., a Delaware corporation.

          (e) “Compensation” means (i) the total compensation paid in cash to a Participant by a
Participating Company, including salaries, wages, bonuses, incentive compensation, commissions,
overtime pay and shift premiums, plus (ii) any pre-tax contributions made by the Participant under
section 401(k) or 125 of the Code. “Compensation” shall exclude all non-cash items, moving or
relocation allowances, cost-of-living equalization payments, car allowances, tuition
reimbursements, imputed income attributable to cars or life insurance, severance pay, fringe
benefits, contributions or benefits received under employee benefit plans, income attributable to
the exercise of stock options, and similar items. The Committee shall determine whether a
particular item is included in Compensation.

          (f) “Corporate Reorganization” means:

          (i) The consummation of a merger or consolidation of the Company with or into
another entity or any other corporate reorganization; or

          (ii) The sale, transfer or other disposition of all or substantially all of the
Company’s assets or the complete liquidation or dissolution of the Company.

          (g) “Eligible Employee” means any employee of a Participating Company who meets both of the
following requirements:

          (i) His or her customary employment is for more than five months per calendar
year and for more than 20 hours per week; and

          (ii) He or she has been an employee of a Participating Company for not less
than one month, or such other period not in excess of 24

8

 

months as the Committee may
determine before the beginning of the applicable Offering Period.

The foregoing notwithstanding, an individual shall not be considered an Eligible Employee if his or
her participation in the Plan is prohibited by the law of any country that has jurisdiction over
him or her or if he or she is subject to a collective bargaining agreement that does not provide
for participation in the Plan.

          (h) “Exchange Act” means the Securities Exchange Act of 1934, as amended.

          (i) “Fair Market Value” means the price at which Stock was last sold in the principal U.S.
market for Stock on the applicable date
or, if the applicable date was not a trading day, on the last trading day prior to the
applicable date. If Stock is no longer traded on a public U.S. securities market, the Fair Market
Value shall be determined by the Committee in good faith on such basis as it deems appropriate.
The Committee’s determination shall be conclusive and binding on all persons.

          (j) “IPO” means the Company’s initial offering of Stock to the public.

          (k) “IPO Date” means the effective date of the registration statement filed by the Company
with the Securities and Exchange Commission for its initial offering of Stock to the public.

          (l) “Offering Period” means a period with respect to which the right to purchase Stock may be
granted under the Plan, as determined pursuant to Section 4(a).

          (m) “Participant” means an Eligible Employee who participates in the Plan, as provided in
Section 4.

          (n) “Participating Company” means (i) the Company and (ii) each present or future Subsidiary
designated by the Committee as a Participating Company.

          (o) “Plan” means this Synacor, Inc. 2007 Employee Stock Purchase Plan, as it may be amended
from time to time.

          (p) “Plan Account” means the account established for each Participant pursuant to
Section 8(a).

          (q) “Purchase Price” means the price at which Participants may purchase Stock under the Plan,
as determined pursuant to Section 8(b).

          (r) “Stock” means the Common Stock of the Company.

          (s) “Subsidiary” means any corporation (other than the Company) in an unbroken chain of
corporations beginning with the Company, if each of the corporations other than the last
corporation in the unbroken chain owns stock possessing 50% or more of the total combined voting
power of all classes of stock in one of the other corporations in such chain.

9

 

SECTION 17. EXECUTION.

          To record the adoption of the Plan by the Board on September 17, 2007, the Company has caused
its duly authorized officer to execute this document in the name of the Company.

	 	 	 	 	 
	 	 	Synacor, Inc.
	 
	 	 	 	 
	 

	 	By:	 	/s/ Ron Frankel
	 

	 	 	 	 
	 

	 	Title:	 	Chief Executive Officer
	 

	 	 	 	 

10EX-4.3

 

Exhibit 4.3

NEITHER THESE SECURITIES NOR THE SECURITIES ISSUABLE UPON EXERCISE OF THESE SECURITIES HAVE BEEN
REGISTERED WITH THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF ANY STATE IN
RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE
“SECURITIES ACT”) AND APPLICABLE STATE SECURITIES LAWS AND, ACCORDINGLY, MAY NOT BE OFFERED OR SOLD
EXCEPT PURSUANT TO (I) AN EFFECTIVE REGISTRATION STATEMENT UNDER THE SECURITIES ACT OR (II) AN
AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE
SECURITIES ACT AND IN ACCORDANCE WITH APPLICABLE STATE SECURITIES LAWS OR BLUE SKY LAWS. THESE
SECURITIES AND THE SECURITIES ISSUABLE UPON EXERCISE OF THESE SECURITIES MAY BE PLEDGED IN
CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN SECURED BY SUCH SECURITIES.

INTERNATIONAL FIGHT LEAGUE, INC.

WARRANT TO PURCHASE COMMON STOCK

	 	 	 	 	 
	Warrant No. 22

	 	 	 	Original Issue Date: August 6, 2007

     INTERNATIONAL FIGHT LEAGUE, INC., a Delaware corporation (the “Company”), hereby certifies
that, for value received, PIPER JAFFRAY & CO. or its permitted registered assigns (the “Holder”),
is entitled to purchase from the Company up to a total of 729,900 shares of common stock, $0.01 par
value per share (the “Common Stock”), of the Company (each such share, a “Warrant Share” and all
such shares, the “Warrant Shares”) at an exercise price per share equal to $1.05 (as adjusted from
time to time as provided in Section 9 herein, the “Exercise Price”), at any time and from
time to time from and after the Original Issue Date (the “Issuance Date”) and through and including
5:00 P.M., New York City time, on August 6, 2012 (the “Expiration Date”), and subject to the
following terms and conditions:

     This Warrant (this “Warrant”) is one of a series of similar warrants issued pursuant to that
certain Securities Purchase Agreement, dated as of August 1, 2007, by and among the Company and the
Purchasers identified therein (the “Purchase Agreement”). All such warrants are referred to
herein, collectively, as the “Warrants.”

1. Definitions. In addition to the terms defined elsewhere in this Warrant, capitalized
terms that are not otherwise defined herein have the meanings ascribed to such terms in the
Purchase Agreement.

2. Registration of Warrants. The Company shall register this Warrant, upon records to be
maintained by the Company for that purpose (the “Warrant Register”), in the name of the record
Holder (which shall include the initial Holder or, as the case may be, any registered assignee to
which this Warrant is permissibly assigned hereunder) from time to time. The Company may deem and
treat the registered Holder of this Warrant as the absolute owner hereof for the purpose of any
exercise hereof or any distribution to the Holder, and for all other purposes, absent actual notice
to the contrary.

3. Registration of Transfers. Subject to the restrictions on transfer set forth in Section
4.1 of the Purchase Agreement and Section 15(b) hereof and compliance with all applicable
securities

1

 

laws, the Company shall register the transfer of all or any portion of this Warrant to an Affiliate
of the Holder in the Warrant Register, upon (i) surrender of this Warrant with a completed Form of
Assignment attached as Schedule 1 duly completed and signed by the transferee, to the
Company at its address specified herein; (ii) if the Registration Statement is not effective,
delivery by or on behalf of the transferring Holder (at its expense), at the request of the
Company, of an opinion of counsel reasonably satisfactory to the Company to the effect that the
transfer of such portion of this Warrant may be made pursuant to an available exemption from the
registration requirements of the Securities Act and all applicable state securities or blue sky
laws; and (iii) accurate completion, execution and by the transferee of the Certification attached
hereto as Appendix A to Schedule 1. Upon any such registration or transfer
(including, to the extent applicable, receipt of the items set forth in clauses (i), (ii) and (iii)
immediately preceding), a new warrant to purchase Common Stock in substantially the form of this
Warrant (any such new warrant, a “New Warrant”) evidencing the portion of this Warrant so
transferred shall be issued to the transferee, and a New Warrant evidencing the remaining portion
of this Warrant not so transferred, if any, shall be issued to the transferring Holder. The
acceptance of the New Warrant by the transferee thereof shall be deemed the acceptance by such
transferee of all of the rights and obligations of a Holder of a Warrant.

4. Exercise and Duration of Warrant.

     (a) All or any part of this Warrant shall be exercisable by the registered Holder at any time
and from time to time on or after the Issuance Date and through and including 5:00 P.M. New York
City time on the Expiration Date. At 5:00 P.M., New York City time, on the Expiration Date, the
portion of this Warrant not exercised prior thereto shall be and become void and of no value and
this Warrant shall be terminated and no longer outstanding;

     (b) The Holder may exercise this Warrant by delivering to the Company (i) an exercise notice,
in the form attached as Schedule 2 hereto (the “Exercise Notice”), appropriately completed
and duly signed, and (ii) payment of the Exercise Price for the number of Warrant Shares as to
which this Warrant is being exercised (which may take the form of a “cashless exercise” if so
indicated in the Exercise Notice and if a “cashless exercise” may occur at such time pursuant to
Section 10 below), and the date such items are delivered to the Company (as determined in
accordance with the notice provisions hereof) is an “Exercise Date.” The delivery by (or on behalf
of) the Holder of the Exercise Notice and the applicable Exercise Price as provided above shall
constitute the Holder’s certification to the Company that its representations contained in the
Purchase Agreement are true and correct as of the Exercise Date as if remade in their entirety (or,
in the case of any transferee Holder, such transferee Holder’s duly executed certification to the
Company that such representations are true and correct as to such transferee Holder as of the
Exercise Date). Execution and delivery of the Exercise Notice shall have the same effect as
cancellation of the original Warrant and issuance of a New Warrant evidencing the right to purchase
the remaining number of Warrant Shares.

5. Delivery of Warrant Shares.

     (a) Upon exercise of this Warrant, the Company shall promptly (but in no event later than
three (3) Trading Days after the Exercise Date) issue or cause to be issued and cause to be
delivered to or upon the written order of the Holder and in such name or names as the Holder may
designate (provided that, if the Registration Statement is not effective and the Holder directs the
Company to deliver a certificate for the Warrant Shares in a name other than that of the Holder or
an Affiliate of the Holder, it shall deliver to the Company on the Exercise Date an opinion of
counsel reasonably satisfactory to the Company to the effect that the issuance of such Warrant

2

 

Shares in such other name may be made pursuant to an available exemption from the registration
requirements of the Securities Act and all applicable state securities or blue sky laws), a
certificate for the Warrant Shares issuable upon such exercise, free of restrictive legends, unless
a registration statement covering the resale of the Warrant Shares and naming the Holder as a
selling stockholder thereunder is not then effective or the Warrant Shares are not freely
transferable without volume restrictions pursuant to Rule 144(k) under the Securities Act. The
Holder, or any Person permissibly so designated by the Holder to receive Warrant Shares, shall be
deemed to have become the holder of record of such Warrant Shares as of the Exercise Date.

     (b) If by the close of the third (3) Trading Day after delivery of an Exercise Notice, the
Company fails to deliver to the Holder a certificate representing the required number of Warrant
Shares in the manner required pursuant to Section 5(a), and if after such third Trading Day and
prior to the receipt of such Warrant Shares, the Holder purchases (in an open market transaction or
otherwise) shares of Common Stock to deliver in satisfaction of a sale by the Holder of the Warrant
Shares which the Holder anticipated receiving upon such exercise (a “Buy-In”), then the Company
shall, within three Trading Days after the Holder’s request and in the Holder’s sole discretion,
either (1) pay in cash to the Holder an amount equal to the Holder’s total purchase price
(including brokerage commissions, if any) for the shares of Common Stock so purchased (the “Buy-In
Price”), at which point the Company’s obligation to deliver such certificate (and to issue such
Warrant Shares) shall terminate or (2) promptly honor its obligation to deliver to the Holder a
certificate or certificates representing such Warrant Shares and pay cash to the Holder in an
amount equal to the excess (if any) of the Buy-In Price over the product of (A) such number of
Warrant Shares, times (B) the closing bid price of a share of Common Stock on the date of exercise.

 

     (c) To the extent permitted by law, the Company’s obligations to issue and deliver Warrant
Shares in accordance with the terms hereof are absolute and unconditional, irrespective of any
action or inaction by the Holder to enforce the same, any waiver or consent with respect to any
provision hereof, the recovery of any judgment against any Person or any action to enforce the
same, or any setoff, counterclaim, recoupment, limitation or termination, or any breach or alleged
breach by the Holder or any other Person of any obligation to the Company or any violation or
alleged violation of law by the Holder or any other Person, and irrespective of any other
circumstance which might otherwise limit such obligation of the Company to the Holder in connection
with the issuance of Warrant Shares. Nothing herein shall limit the Holder’s right to pursue any
other remedies available to it hereunder, at law or in equity including, without limitation, a
decree of specific performance and/or injunctive relief with respect to the Company’s failure to
timely deliver certificates representing shares of Common Stock upon exercise of this Warrant as
required pursuant to the terms hereof.

6. Charges, Taxes and Expenses. Issuance and delivery of certificates for shares of Common
Stock upon exercise of this Warrant shall be made without charge to the Holder for any issue or
transfer tax, withholding tax, transfer agent fee or other incidental tax or expense in respect of
the issuance of such certificates, all of which taxes and expenses shall be paid by the Company;
provided, however, that the Company shall not be required to pay any tax which may be payable in
respect of any transfer involved in the registration of any certificates for Warrant Shares or
Warrants in a name other than that of the Holder or an Affiliate thereof. The Holder shall be
responsible for all other tax liability that may arise as a result of holding or transferring this
Warrant or receiving Warrant Shares upon exercise hereof.

7. Replacement of Warrant. If this Warrant is mutilated, lost, stolen or destroyed, the
Company shall issue or cause to be issued in exchange and substitution for and upon cancellation

3

 

hereof, or in lieu of and substitution for this Warrant, a New Warrant, but only upon receipt of
evidence reasonably satisfactory to the Company of such loss, theft or destruction (in such case)
and, in each case, a customary and reasonable indemnity, if requested. Applicants for a New Warrant
under such circumstances shall also comply with such other reasonable regulations and procedures
and pay such other reasonable third-party costs as the Company may prescribe. If a New Warrant is
requested as a result of a mutilation of this Warrant, then the Holder shall deliver such mutilated
Warrant to the Company as a condition precedent to the Company’s obligation to issue the New
Warrant.

8. Reservation of Warrant Shares. The Company covenants that it will initially reserve and
keep available out of the aggregate of its authorized but unissued and otherwise unreserved Common
Stock, solely for the purpose of enabling it to issue Warrant Shares upon exercise of this Warrant
as herein provided, the number of Warrant Shares which are initially issuable and deliverable upon
the exercise of this entire Warrant, free from preemptive rights or any other contingent purchase
rights of persons other than the Holder. The Company further covenants that it will at all times
reserve and keep available out of the aggregate of its authorized but unissued and otherwise
unreserved Common Stock, solely for the purpose of enabling it to issue Warrant Shares upon
exercise of this Warrant as herein provided, the number of Warrant Shares which are then issuable
and deliverable upon the exercise of this entire Warrant, free from preemptive rights or any other
contingent purchase rights of persons other than the Holder (taking into account the adjustments
and restrictions of Section 9). The Company covenants that all Warrant Shares so issuable
and deliverable shall, upon issuance and the payment of the applicable Exercise Price in accordance
with the terms hereof, be duly and validly authorized, issued and fully paid and nonassessable. The
Company will take all such action as may be reasonably necessary to assure that such shares of
Common Stock may be issued as provided herein without violation of any applicable law or
regulation, or of any requirements of any securities exchange or automated quotation system upon
which the Common Shares may be listed.

9. Certain Adjustments. The Exercise Price and number of Warrant Shares issuable upon
exercise of this Warrant are subject to adjustment from time to time as set forth in this
Section 9.

     (a) Stock Dividends and Splits. If the Company, at any time while this Warrant is
outstanding, (i) pays a stock dividend on its Common Stock or otherwise makes a distribution on any
class of capital stock that is payable in shares of Common Stock, (ii) subdivides its outstanding
shares of Common Stock into a larger number of shares, or (iii) combines its outstanding shares of
Common Stock into a smaller number of shares, then in each such case the Exercise Price shall be
multiplied by a fraction, the numerator of which shall be the number of shares of Common Stock
outstanding immediately before such event and the denominator of which shall be the number of
shares of Common Stock outstanding immediately after such event. Any adjustment made pursuant to
clause (i) of this paragraph shall become effective immediately after the record date for the
determination of stockholders entitled to receive such dividend or distribution, and any adjustment
pursuant to clause (ii) or (iii) of this paragraph shall become effective immediately after the
effective date of such subdivision or combination.

     (b) Pro Rata Distributions. If the Company, at any time while this Warrant is
outstanding, distributes to all holders of Common Stock (i) evidences of its indebtedness, (ii) any
security (other than a distribution of Common Stock covered by the preceding paragraph), (iii)
rights or warrants to subscribe for or purchase any security, or (iv) any other asset (in each
case, “Distributed Property”), then, upon any exercise of this Warrant that occurs after the record
date fixed for determination of stockholders entitled to receive such distribution, the Holder
shall be entitled to receive, in addition to the Warrant Shares otherwise issuable upon such
exercise (if

4

 

applicable), the Distributed Property that such Holder would have been entitled to receive in
respect of such number of Warrant Shares had the Holder been the record holder of such Warrant
Shares immediately prior to such record date.

     (c) Fundamental Transactions. If, at any time while this Warrant is outstanding (i)
the Company effects any merger or consolidation of the Company with or into another Person, in
which the Company is not the survivor, (ii) the Company effects any sale of all or substantially
all of its assets or a majority of its Common Stock is acquired by a third party, in each case, in
one or a series of related transactions, (iii) any tender offer or exchange offer (whether by the
Company or another Person) is completed pursuant to which all or substantially all of the holders
of Common Stock are permitted to tender or exchange their shares for other securities, cash or
property, or (iv) the Company effects any reclassification of the Common Stock or any compulsory
share exchange pursuant to which the Common Stock is effectively converted into or exchanged for
other securities, cash or property (other than as a result of a subdivision or combination of
shares of Common Stock covered by Section 9(a) above) (in any such case, a “Fundamental
Transaction”), then the Holder shall have the right thereafter to receive, upon exercise of this
Warrant, the same amount and kind of securities, cash or property as it would have been entitled to
receive upon the occurrence of such Fundamental Transaction if it had been, immediately prior to
such Fundamental Transaction, the holder of the number of Warrant Shares then issuable upon
exercise in full of this Warrant without regard to any limitations on exercise contained herein
(the “Alternate Consideration”). Notwithstanding the foregoing, in the event of a Fundamental
Transaction that, is (1) a transaction where the consideration paid to the holders of the Common
Stock consists solely of cash, (2) a “Rule 13e-3 transaction” as defined in Rule 13e-3 under the
Securities Exchange Act of 1934, as amended, or (3) a Fundamental Transaction involving a person or
entity not traded on a Trading Market (other than the OTC Bulletin Board), at the request of the
Holder delivered before the 90th day after such Fundamental Transaction, the Company (or the
successor entity to the Company) shall purchase this Warrant from the Holder by paying to the
Holder, within five (5) Business Days after such request (or, if later, on the effective date of
the Fundamental Transaction), cash in an amount equal to the value of the remaining unexercised
portion of this Warrant on the date of such Fundamental Transaction, which value shall be
determined by use of the Black Scholes Option Pricing Model obtained from the “OV” function on
Bloomberg determined as of the day immediately following the public announcement of the applicable
Fundamental Transaction and reflecting (i) a risk-free interest rate corresponding to the U.S.
Treasury rate for a period equal to the remaining term of this Warrant as of such date of request
and (ii) an expected volatility equal to the greater of (A) 40% and (B) the 100 day volatility
obtained from the HVT function on Bloomberg determined as of the Trading Day immediately prior to
the announcement of the Fundamental Transaction. The provisions of this paragraph (c) shall
similarly apply to subsequent transactions analogous to a Fundamental Transaction.

     (d) Number of Warrant Shares. Simultaneously with any adjustment to the Exercise Price
pursuant to this Section 9, the number of Warrant Shares that may be purchased upon
exercise of this Warrant shall be increased or decreased proportionately, so that after such
adjustment the aggregate Exercise Price payable hereunder for the increased or decreased number of
Warrant Shares shall be the same as the aggregate Exercise Price in effect immediately prior to
such adjustment.

     (e) Calculations. All calculations under this Section 9 shall be made to the
nearest cent or the nearest 1/100th of a share, as applicable. The number of shares of
Common Stock outstanding at any given time shall not include shares owned or held by or for the
account of the

5

 

Company, and the sale or issuance of any such shares shall be considered an issue or sale of
Common Stock.

     (f) Notice of Adjustments. Upon the occurrence of each adjustment pursuant to this
Section 9, the Company at its expense will, at the written request of the Holder, promptly
compute such adjustment, in good faith, in accordance with the terms of this Warrant and prepare a
certificate setting forth such adjustment, including a statement of the adjusted Exercise Price and
adjusted number or type of Warrant Shares or other securities issuable upon exercise of this
Warrant (as applicable), describing the transactions giving rise to such adjustments and showing in
detail the facts upon which such adjustment is based. Upon written request, the Company will
promptly deliver a copy of each such certificate to the Holder and to the Company’s transfer agent.

10. Payment of Exercise Price. The Holder shall pay the Exercise Price in immediately
available funds; provided, however, that, notwithstanding anything contained herein
to the contrary, at any time after the Original Issuance Date, the Holder may, in its sole
discretion, satisfy its obligation to pay the Exercise Price through a “cashless exercise”, in
which event the Company shall issue to the Holder the number of Warrant Shares determined as
follows:

 

X = Y [(A-B)/A]

     where:

X = the number of Warrant Shares to be issued to the Holder.

Y = the total number of Warrant Shares with respect to which this Warrant is
being exercised.

A = the average of the Closing Sale Prices of the shares of Common Stock (as
reported by Bloomberg Financial Markets) for the five Trading Days ending on the
date immediately preceding the Exercise Date.

B = the Exercise Price then in effect for the applicable Warrant Shares at the
time of such exercise.

For purposes of this Warrant, “Closing Sale Price” means, for any security as of any date, the last
trade price for such security on the principal securities exchange or trading market for such
security, as reported by Bloomberg Financial Markets, or, if such exchange or trading market begins
to operate on an extended hours basis and does not designate the last trade price, then the last
trade price of such security prior to 4:00 P.M., New York City time, as reported by Bloomberg
Financial Markets, or if the foregoing do not apply, the last trade price of such security in the
over-the-counter market on the electronic bulletin board for such security as reported by Bloomberg
Financial Markets, or, if no last trade price is reported for such security by Bloomberg Financial
Markets, the average of the bid prices, or the ask prices, respectively, of any market makers for
such security as reported in the “pink sheets” by Pink Sheets LLC. If the Closing Sale Price
cannot be calculated for a security on a particular date on any of the foregoing bases, the Closing
Sale Price of such security on such date shall be the fair market value as determined in good faith
by the Company. If the Holder disputes the fair market value of such security by written notice to
the Company and the Company and the Holder are unable to agree upon the fair market value of such
securities, then the Company shall, within two business days

6

 

submit via facsimile (a) the disputed determination of the Exercise Price to an independent,
reputable investment bank selected by the Company and approved by the Holder or (b) the disputed
arithmetic calculation of the Warrant Shares to the Company’s independent, outside accountant. The
Company shall cause the investment bank or the accountant, as the case may be, to perform the
determinations or calculations and notify the Company and the Holder of the results no later than
ten business days from the time it receives the disputed determinations or calculations. Such
investment bank’s or accountant’s determination or calculation, as the case may be, shall be
binding upon all parties absent demonstrable error. All such determinations shall be appropriately
adjusted for any stock dividend, stock split, stock combination or other similar transaction during
the applicable calculation period. The party whose determination of fair market value is further
from the fair market value, as determined by the investment bank or the accountant, shall pay the
fees of such investment bank or accountant.

For purposes of Rule 144 promulgated under the Securities Act, it is intended, understood and
acknowledged that the Warrant Shares issued in a cashless exercise transaction shall be deemed to
have been acquired by the Holder, and the holding period for the Warrant Shares shall be deemed to
have commenced, on the date this Warrant was originally issued pursuant to the Purchase Agreement
(provided that the Commission continues to take the position that such treatment is proper at the
time of such exercise).

11. No Fractional Shares. No fractional Warrant Shares will be issued in connection with
any exercise of this Warrant. In lieu of any fractional shares which would otherwise be issuable,
the number of shares of Warrant Shares to be issued shall be rounded up to the nearest whole
number.

12. Notices. Any and all notices or other communications or deliveries hereunder
(including, without limitation, any Exercise Notice) shall be in writing and shall be deemed given
and effective on the earliest of (i) the date of transmission, if such notice or communication is
delivered via facsimile or e-mail at the facsimile number or e-mail address specified in the
Purchase Agreement prior to 5:00 p.m. (New York City time) on a Trading Day, (ii) the next Trading
Day after the date of transmission, if such notice or communication is delivered via facsimile at
the facsimile number specified in the Purchase Agreement on a day that is not a Trading Day or
later than 5:00 p.m. (New York City time) on any Trading Day, (iii) the Trading Day following the
date of mailing, if sent by nationally recognized overnight courier service specifying next Trading
Day delivery, or (iv) upon actual receipt by the party to whom such notice is required to be given,
if by hand delivery. The address and facsimile number of a party for such notices or communications
shall be as set forth below unless changed by such party by two (2) Trading Days’ prior notice to
the other party in accordance with this Section 12:

	 	 	 	 	 
	 

	 	If to the Company:
	 	International Fight League, Inc.
	 

	 	 	 	424 West 33rd Street, Suite 650
	 

	 	 	 	New York, New York 10001
	 

	 	 	 	Telephone No.: (212) 356-4000
	 

	 	 	 	Facsimile No.: (212) 564-6546
	 

	 	 	 	Attention: Michael Keefe

7

 

	 	 	 	 	 
	 

	 	With a copy to:
	 	Lowenstein Sandler PC
	 

	 	 	 	1251 Avenue of the Americas
	 

	 	 	 	New York, New York 10020
	 

	 	 	 	Telephone No.: (212) 262-6700
	 

	 	 	 	Facsimile No.: (973) 597-2507
	 

	 	 	 	Attention: Steven E. Siesser, Esq.
	 
	 	 	 	 
	 

	 	If to the original Holder:
	 	Piper Jaffray & Co.
	 

	 	 	 	800 Nicollet Mall — Suite 800
	 

	 	 	 	Minneapolis, MN 55402-7020
	 

	 	 	 	Telephone No.: 612-303-6000
	 

	 	 	 	Facsimile No.: 612-303-1410
	 

	 	 	 	Attention: Mr. James Martin
	 
	 	 	 	 
	 

	 	With a copy to:
	 	Nelson Mullins Riley & Scarborough LLP
	 

	 	 	 	101 Constitution Avenue, N.W. — Suite 900
	 

	 	 	 	Washington, D.C. 20001
	 

	 	 	 	Telephone No.: 202-712-2806
	 

	 	 	 	Facsimile No.: 202-712-2860
	 

	 	 	 	Attn: Jon Talcott, Esq.

13. Warrant Agent. The Company shall serve as warrant agent under this Warrant. Upon
thirty (30) days’ notice to the Holder, the Company may appoint a new warrant agent. Any
corporation into which the Company or any new warrant agent may be merged or any corporation
resulting from any consolidation to which the Company or any new warrant agent shall be a party or
any corporation to which the Company or any new warrant agent transfers substantially all of its
corporate trust or shareholders services business shall be a successor warrant agent under this
Warrant without any further act. Any such successor warrant agent shall promptly cause notice of
its succession as warrant agent to be mailed (by first class mail, postage prepaid) to the Holder
at the Holder’s last address as shown on the Warrant Register.

14. Limitations on Exercise. The Company shall not effect the exercise of this Warrant,
and the Holder shall not have the right to exercise this Warrant, to the extent that after giving
effect to such exercise, such Person (together with such Person’s affiliates) would beneficially
own in excess of 4.99% (the “Maximum Percentage”) of the shares of Common Stock outstanding
immediately after giving effect to such exercise. For purposes of the foregoing sentence, the
aggregate number of shares of Common Stock beneficially owned by such Person and its affiliates
shall include the number of shares of Common Stock issuable upon exercise of this Warrant with
respect to which the determination of such sentence is being made, but shall exclude shares of
Common Stock which would be issuable upon (i) exercise of the remaining, unexercised portion of
this Warrant beneficially owned by such Person and its affiliates and (ii) exercise or conversion
of the unexercised or unconverted portion of any other securities of the Company beneficially owned
by such Person and its affiliates (including, without limitation, any convertible notes or
convertible preferred stock or warrants) subject to a limitation on conversion or exercise
analogous to the limitation contained herein. Except as set forth in the preceding sentence, for
purposes of this paragraph, beneficial ownership shall be calculated in accordance with Section
13(d) of the Securities Exchange Act of 1934, as amended. For purposes of this Warrant, in
determining the number of outstanding shares of Common Stock, the Holder may rely on the number of
outstanding shares of Common Stock as reflected in (1) the Company’s most recent Form 10-K, Form
10-KSB, Form 10-Q, Form 10-QSB, Current Report on Form 8-K or

8

 

other public filing with the Securities and Exchange Commission, as the case may be, (2) a more
recent public announcement by the Company or (3) any other notice by the Company or the Transfer
Agent setting forth the number of shares of Common Stock outstanding. For any reason at any time,
upon the written or oral request of the Holder, the Company shall within one Business Day confirm
orally and in writing to the Holder the number of shares of Common Stock then outstanding. In any
case, the number of outstanding shares of Common Stock shall be determined after giving effect to
the conversion or exercise of securities of the Company, including the warrants issued pursuant to
the Purchase Agreement, by the Holder and its affiliates since the date as of which such number of
outstanding shares of Common Stock was reported. By written notice to the Company, the Holder may
from time to time increase or decrease the Maximum Percentage to any other percentage not in excess
of 9.99% specified in such notice; provided that (I) any such increase will not be effective until
the sixty-first (61st) day after such notice is delivered to the Company, and (II) any such
increase or decrease will apply only to the Holder and not to any other holder of warrants issued
pursuant to the Purchase Agreement.

15. Miscellaneous.

     (a) The Holder, solely in such Person’s capacity as a holder of this Warrant, shall not be
entitled to vote or receive dividends or be deemed the holder of share capital of the Company for
any purpose, nor shall anything contained in this Warrant be construed to confer upon the Holder,
solely in such Person’s capacity as the Holder of this Warrant, any of the rights of a stockholder
of the Company or any right to vote, give or withhold consent to any corporate action (whether any
reorganization, issue of stock, reclassification of stock, consolidation, merger, amalgamation,
conveyance or otherwise), receive notice of meetings, receive dividends or subscription rights, or
otherwise, prior to the issuance to the Holder of the Warrant Shares which such Person is then
entitled to receive upon the due exercise of this Warrant. In addition, nothing contained in this
Warrant shall be construed as imposing any liabilities on the Holder to purchase any securities
(upon exercise of this Warrant or otherwise) or as a stockholder of the Company, whether such
liabilities are asserted by the Company or by creditors of the Company.

     (b) Subject to compliance with applicable securities laws, this Warrant shall not be assigned
by the Holder, unless the Holder shall, together with such assignment, provide written notice
thereof to the Company, in the form of Schedule 1 annexed hereto and made a part hereof.
This Warrant shall not be assigned by the Company except to a successor in the event of a
Fundamental Transaction.

     (c) This Warrant shall be binding on and inure to the benefit of the parties hereto and their
respective permitted successors and assigns. Subject to the preceding sentence, nothing in this
Warrant shall be construed to give to any Person other than the Company and the Holder any legal or
equitable right, remedy or cause of action under this Warrant. This Warrant shall be amended only
in writing signed by the Company and the Holder, or their permitted successors and assigns.

     (d) GOVERNING LAW; VENUE; WAIVER OF JURY TRIAL. ALL QUESTIONS CONCERNING THE CONSTRUCTION,
VALIDITY, ENFORCEMENT AND INTERPRETATION OF THIS WARRANT SHALL BE GOVERNED BY AND CONSTRUED AND
ENFORCED EXCLUSIVELY IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW YORK WITHOUT REGARD TO THE
PRINCIPLES OF CONFLICTS OF LAW THEREOF (OTHER THAN SECTIONS 5-1401 AND 5-1402 OF THE NEW YORK
GENERAL OBLIGATIONS LAW). EACH PARTY HEREBY IRREVOCABLY SUBMITS TO THE EXCLUSIVE JURISDICTION OF
THE STATE AND FEDERAL COURTS SITTING IN

9

 

THE CITY OF NEW YORK, BOROUGH OF MANHATTAN, FOR THE ADJUDICATION OF ANY DISPUTE HEREUNDER OR
IN CONNECTION HEREWITH OR WITH ANY TRANSACTION CONTEMPLATED HEREBY OR DISCUSSED HEREIN (INCLUDING
WITH RESPECT TO THE ENFORCEMENT OF ANY OF THE TRANSACTION DOCUMENTS), AND HEREBY IRREVOCABLY
WAIVES, AND AGREES NOT TO ASSERT IN ANY SUIT, ACTION OR PROCEEDING, ANY CLAIM THAT IT IS NOT
PERSONALLY SUBJECT TO THE JURISDICTION OF ANY SUCH COURT, THAT SUCH SUIT, ACTION OR PROCEEDING IS
IMPROPER. EACH PARTY HEREBY IRREVOCABLY WAIVES PERSONAL SERVICE OF PROCESS AND CONSENTS TO PROCESS
BEING SERVED IN ANY SUCH SUIT, ACTION OR PROCEEDING BY MAILING A COPY THEREOF VIA REGISTERED OR
CERTIFIED MAIL OR OVERNIGHT DELIVERY (WITH EVIDENCE OF DELIVERY) TO SUCH PARTY AT THE ADDRESS IN
EFFECT FOR NOTICES TO IT UNDER THIS AGREEMENT AND AGREES THAT SUCH SERVICE SHALL CONSTITUTE GOOD
AND SUFFICIENT SERVICE OF PROCESS AND NOTICE THEREOF. NOTHING CONTAINED HEREIN SHALL BE DEEMED TO
LIMIT IN ANY WAY ANY RIGHT TO SERVE PROCESS IN ANY MANNER PERMITTED BY LAW. THE COMPANY HEREBY
WAIVES ALL RIGHTS TO A TRIAL BY JURY. 

     (e) The headings herein are for convenience only, do not constitute a part of this Warrant and
shall not be deemed to limit or affect any of the provisions hereof.

     (f) In case any one or more of the provisions of this Warrant shall be invalid or
unenforceable in any respect, the validity and enforceability of the remaining terms and provisions
of this Warrant shall not in any way be affected or impaired thereby, and the parties will attempt
in good faith to agree upon a valid and enforceable provision which shall be a commercially
reasonable substitute therefor, and upon so agreeing, shall incorporate such substitute provision
in this Warrant.

     (g) Prior to exercise of this Warrant, the Holder hereof shall not, by reason of by being a
Holder, be entitled to any rights of a stockholder with respect to the Warrant Shares.

16. Registration Rights. This Warrant has been issued in connection with the transactions
contemplated by (a) the Purchase Agreement, and (b) that certain Registration Rights Agreement of
even date therewith. The Holder of this Warrant is entitled to have the Warrant Shares included as
Registrable Securities and registered for resale under the Securities Act, subject to and in
accordance with the Registration Rights Agreement.

17. Definitions.

     “Affiliate” of any specified Person means any other person or entity directly or indirectly
controlling, controlled by or under direct or indirect common control with such specified Person.
For purposes of this definition, “control” means the power to direct the management and policies of
such Person or firm, directly or indirectly, whether through the ownership of voting securities, by
contract or otherwise.

     “Eligible Market” means whichever of the New York Stock Exchange, the American Stock Exchange,
the NASDAQ Global Select Market, the NASDAQ Global Market, the NASDAQ Capital Market, or the OTC
Bulletin Board on which the Common Stock is listed or quoted for trading on the date in question.

10

 

     “Person” means any court or other federal, state, local or other governmental authority or
other individual or corporation, partnership, trust, incorporated or unincorporated association,
joint venture, limited liability company, joint stock company, government (or an agency or
subdivision thereof) or other entity of any kind.

     “Trading Day” shall mean any day on which the Common Stock is listed or quoted on any Eligible
Market.

[Signature Page Follows.]

11

 

     IN WITNESS WHEREOF, each of the undersigned has caused this Warrant to be duly executed by its
authorized officer as of the date first indicated above.

	 	 	 	 	 
	 	 	INTERNATIONAL FIGHT LEAGUE, INC.
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	Name:
	 	Gareb Shamus
	 

	 	Title:
	 	Chief Executive Officer

[Signature Page to Warrant]

 

 

SCHEDULE 1

INTERNATIONAL FIGHT LEAGUE, INC.

FORM OF ASSIGNMENT

[To be completed and signed only upon transfer of Warrant]

FOR VALUE RECEIVED, the undersigned hereby sells, assigns and transfers unto
                    
(the “Transferee” the right represented by the within Warrant to purchase                      shares of Common Stock of International Fight League, Inc., a
Delaware corporation (the “Company”) to which the within Warrant relates and appoints
                     attorney to transfer said right on the books of the Company
with full power of substitution in the premises. In connection therewith, the undersigned
represents, warrants, covenants and agrees to and with the Company that:

	 	(a)	 	the offer and sale of the Warrant contemplated hereby is being made in
compliance with Section 4(1) of the United States Securities Act of 1933, as amended
(the “Securities Act”) or another valid exemption from the registration requirements
of Section 5 of the Securities Act and in compliance with all applicable securities
laws of the states of the United States;
	 
	 	(b)	 	the undersigned has not offered to sell the Warrant by any form of general
solicitation or general advertising, including, but not limited to, any advertisement,
article, notice or other communication published in any newspaper, magazine or similar
media or broadcast over television or radio, and any seminar or meeting whose
attendees have been invited by any general solicitation or general advertising;
	 
	 	(c)	 	the undersigned has read the Transferee’s completed Appendix A to
Schedule 1 included herewith, and to its actual knowledge, the statements made
therein are true and correct; and
	 
	 	(d)	 	the undersigned understands that the Company may condition the transfer of
the Warrant contemplated hereby upon the delivery to the Company by the undersigned or
the Transferee, as the case may be, of a written opinion of counsel (which opinion
shall be in form, substance and scope customary for opinions of counsel in comparable
transactions) to the effect that such transfer may be made without registration under
the Securities Act and under applicable securities laws of the states of the United
States.

 

 

	 	 	 	 	 	 	 	 	 
	Dated: ___, ___    

	 	 	 	By: 	 	 	 	 
	 

	 	 	 	 	 	 	 	 
	 

	 	 	 	Name: 
	 	[                    ]	 	 
	 

	 	 	 	Title:
	 	 [                    ]	 	 
	 	 	 	 	(Signature must conform in all respects to name
of holder as specified on the face of the
Warrant)
	 

	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 
	 	 	 	 	Address of Transferee
	 

	 	 	 	 	 	 	 	 
	 

	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	In the presence of:
	 	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 	 	 
	 

 

	 	 	 	 	 	 	 	 
	 

	 	 	 	 	 	 	 	 

 

 

Appendix A

to

Schedule 1

Warrant Holder Certification

     In connection with the issuance, transfer and/or exercise of the Warrant to which this
Schedule 1 is attached, as the case may be, the undersigned, as a transferee of the Warrant, hereby
certifies, knowing and intending that the International Fight League, Inc., a Delaware corporation
(the “Company”) is relying hereon in issuing, transferring and/or exercising such Warrant, as the
case may be, that the following representations and warranties are true, accurate and complete as
of the date of such issuance, transfer and/or exercise:

     1. Investment Intent. The undersigned understands that this Warrant and the Warrant
Shares are “restricted securities” and have not been registered under the Securities Act or any
applicable state securities law and is acquiring this Warrant and the Warrant Shares, as the case
may be, as principal for its own account and not with a view to, or for distributing or reselling
this Warrant and such Warrant Shares, as the case may be, or any part thereof in violation of the
Securities Act or any applicable state securities laws, without prejudice, however, to the
undersigned’s right, subject to the provisions of the Warrant, at all times to sell or otherwise
dispose of all or any part of such Warrant Shares pursuant to an effective registration statement
under the Securities Act or under an exemption from such registration and in compliance with
applicable federal and state securities laws. The undersigned is acquiring this Warrant and the
Warrant Shares hereunder, as the case may be, in the ordinary course of its business. The
undersigned does not presently have any agreement, plan or understanding, directly or indirectly,
with any Person to distribute or effect any distribution of this Warrant or any of the Warrant
Shares (or any securities which are derivatives thereof) to or through any person or entity;
provided, however, that by making the representations herein, the undersigned does not agree to
hold this Warrant or any of the Warrant Shares, as the case may be, for any minimum period of time.

     2. Purchaser Status. The undersigned is an “accredited investor” as defined in Rule
501(a) under the Securities Act.

     3. General Solicitation. The undersigned is not acquiring this Warrant or the Warrant
Shares, as the case may be, as a result of any advertisement, article, notice or other
communication regarding this Warrant or the Warrant Shares, published in any newspaper, magazine or
similar media or broadcast over television or radio or presented at any seminar or any other
general advertisement.

     4. Experience of Such Purchaser. The undersigned, either alone or together with its
representatives, has such knowledge, sophistication and experience in business and financial
matters so as to be capable of evaluating the merits and risks of the prospective investment in
this Warrant and the Warrant Shares, and has so evaluated the merits and risks of such investment.
The undersigned is able to bear the economic risk of an investment in this Warrant and the Warrant
Shares and, at the present time, is able to afford a complete loss of such investment.

     5. Access to Information. The undersigned acknowledges that it has been afforded (i) the
opportunity to ask such questions as it has deemed necessary of, and to receive answers from,
representatives of the Company concerning the terms and conditions of the offering of this Warrant
and the Warrant Shares and the merits and risks of investing in this Warrant and the

 

 

Warrant Shares; (ii) access to information (other than material non-public information) about the
Company and the subsidiaries and their respective financial condition, results of operations,
business, properties, management and prospects sufficient to enable it to evaluate its investment;
and (iii) the opportunity to obtain such additional information that the Company possesses or can
acquire without unreasonable effort or expense that is necessary to make an informed investment
decision with respect to the investment.

     6. Independent Investment Decision. The undersigned has independently evaluated the
merits of its decision to acquire this Warrant and the Warrant Shares. The undersigned understands
that nothing in this Warrant or any other materials presented by or on behalf of the Company to the
undersigned in connection with its acquisition of this Warrant and the Warrant Shares or this
Warrant constitutes legal, tax or investment advice. The undersigned has consulted such legal, tax
and investment advisors as it, in its sole discretion, has deemed necessary or appropriate in
connection with its acquisition of this Warrant and the Warrant Shares.

     7. Reliance on Exemptions. The undersigned understands that the Warrant and the
Warrant Shares are being offered and issued to it in reliance on specific exemptions from the
registration requirements of United States federal and state securities laws and that the Company
is relying in part upon the truth and accuracy of, and the undersigned’s compliance with, the
representations, warranties, agreements, acknowledgements and understandings of the undersigned set
forth herein in order to determine the availability of such exemptions and the eligibility of the
undersigned to acquire the Warrant and the Warrant Shares.

     IN WITNESS WHEREOF, the undersigned has caused this Appendix to be duly executed by its
authorized officer as of the date first indicated above.

	 	 	 	 	 
	 
	 	 	 	 
	 	 	NAME OF ENTITY
	 
	 	 	 	 
	 	 	 
	 
	 	 	 	 
	 	 	AUTHORIZED SIGNATORY
	 
	 	 	 	 
	 

	 	By:	 	 
	 

	 	 	 	 
	 

	 	 	 	Name:
	 

	 	 	 	Title:
	 
	 	 	 	 
	 	 	ADDRESS FOR NOTICE
	 
	 	 	 	 
	 

	 	c/o:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Street:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	City/State/Zip:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Attention:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Tel:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Fax:	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Email:	 	 
	 

	 	 	 	 

 

 

SCHEDULE 2

FORM OF EXERCISE NOTICE

(To be executed by the Holder to exercise the right to purchase shares of Common Stock under the
foregoing Warrant)

Ladies and Gentlemen:

(1) The undersigned is the Holder of Warrant No.                      (the “Warrant”) issued by International
Fight League, Inc., a Delaware corporation (the “Company”). Capitalized terms used herein and not
otherwise defined herein have the respective meanings set forth in the Warrant.

(2) The undersigned hereby exercises its right to purchase                      Warrant Shares pursuant to
the Warrant.

(3) The Holder intends that payment of the Exercise Price shall be made as (check one):

	 	 	 	 	 
	 

	 	o
	 	Cash Exercise
	 
	 	 	 	 
	 

	 	o
	 	“Cashless Exercise” under Section 10

(4) Pursuant to this Exercise Notice, the Company shall deliver to the Holder                      Warrant
Shares in accordance with the terms of the Warrant.
 
 

Dated:_______________, _____

	 	 	 	 	 
	Name of Holder:

	 	 

	 	 

	 	 	 	 	 
	By:
	 	 	 	 
	 

	 	 	 	 
	Name:
	 	 	 	 
	 

	 	 	 	 
	Title:
	 	 	 	 
	 

	 	 	 	 

(Signature must conform in all respects to name of Holder as specified on the face of the Warrant)

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