Document:

exv4w2

Exhibit 4.2

IRONPLANET.COM, INC.

THIRD AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT

August 28, 2008

 

 

TABLE OF CONTENTS

	 	 	 	 	 
	 	 	Page	 
	1. Registration Rights
	 	 	2	 
	 
	 	 	 	 
	1.1 Definitions
	 	 	2	 
	1.2 Request for Registration
	 	 	3	 
	1.3 Company Registration
	 	 	4	 
	1.4 Form S-3 Registration
	 	 	5	 
	1.5 Obligations of the Company
	 	 	5	 
	1.6 Furnish Information
	 	 	7	 
	1.7 Expenses of Registration
	 	 	7	 
	1.8 Underwriting Requirements
	 	 	8	 
	1.9 Delay of Registration
	 	 	8	 
	1.10 Indemnification
	 	 	9	 
	1.11 Reports Under Securities Exchange Act of 1934
	 	 	11	 
	1.12 Assignment of Registration Rights
	 	 	11	 
	1.13 Limitations on Subsequent Registration Rights
	 	 	12	 
	1.14 Market Stand-Off Agreement
	 	 	12	 
	1.15 Termination of Registration Rights
	 	 	13	 
	 
	 	 	 	 
	2. Covenants of the Company
	 	 	13	 
	 
	 	 	 	 
	2.1 Delivery of Financial Statements
	 	 	13	 
	2.2 Inspection
	 	 	14	 
	2.3 Right of First Offer
	 	 	14	 
	2.4 Termination of Covenants
	 	 	15	 
	 
	 	 	 	 
	3. Miscellaneous
	 	 	16	 
	 
	 	 	 	 
	3.1 Termination of Entire Agreement Upon Change of Control
	 	 	16	 
	3.2 Successors and Assigns
	 	 	16	 
	3.3 Amendments and Waivers
	 	 	16	 
	3.4 Notices
	 	 	16	 
	3.5 Severability
	 	 	17	 
	3.6 Governing Law
	 	 	17	 
	3.7 Counterparts
	 	 	17	 
	3.8 Titles and Subtitles
	 	 	17	 
	3.9 Aggregation of Stock
	 	 	17	 
	3.10 Observer Rights
	 	 	17	 

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IRONPLANET.COM, INC.

THIRD AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT

     This Third Amended and Restated Investors’ Rights Agreement (the “Agreement”) is made
as of the 28th day of August, 2008, by and among IronPlanet.com, Inc., a Delaware corporation (the
“Company”), the holders of the Company’s Series A Preferred Stock set forth on Exhibit
A attached hereto (the “Series A Holders”), the holders of the Company’s Series B
Preferred Stock set forth on Exhibit A attached hereto (the “Series B Holders”) and
the holders of the Company’s Series C Preferred Stock listed on Exhibit A attached hereto
(the “Series C Holders” and together with the Series A Holders and Series B Holders, the
“Investors”), and Reza Bundy Saadlou, herein referred to as the “Founder.”

RECITALS

     A. The Company, the Founder, the Series A Holders and the Series B Holders have previously
entered into the Second Amended and Restated Investors’ Rights Agreement dated July 19, 2000, and
Amendment No. 1 to the Second Amended and Restated Investors’ Rights Agreements dated May 3, 2007,
pursuant to which the Company granted the Founder, the Series A Holders and Series B Holders
certain rights (the “Prior Rights Agreements”).

     B. The Company has entered of even date herewith and may enter into Series C Preferred Stock
and Preferred Stock Warrant Purchase Agreements (the “Purchase Agreements”) of even date
herewith pursuant to which the Company desires to sell to the Series C Holders and the Series C
Holders desire to purchase from the Company shares of the Company’s Series C Preferred Stock. A
condition to the Series C Holders’ obligations under the Purchase Agreements is that the Company,
the Founder and the Investors enter into this Agreement in order to provide the Series C Holders
with (i) certain rights to register shares of the Company’s Common Stock issuable upon conversion
of the Series C Preferred Stock held by the Series C Holders, (ii) certain rights to receive or
inspect information pertaining to the Company, and (iii) a right of first offer with respect to
certain issuances by the Company of its securities. The Company desires to induce the Series C
Holders to purchase shares of Series C Preferred Stock pursuant to the Purchase Agreements by
agreeing to the terms and conditions set forth herein.

     C. The Company, the Founder, the Series A Holders, and the Series B Holders each desire to
amend and restate the Prior Rights Agreement, which shall be superseded in its entirety by this
Agreement.

AGREEMENT

     The parties hereby agree as follows:

     A. Amendments of Prior Rights Agreement; Waiver of Right of First Offer. Effective and
contingent upon execution of this Agreement by the Company and the holders of a

 

 

majority of the Registrable Securities, as that term is defined in the Prior Rights Agreement,
not including the Founders Stock, as that term is defined in the Prior Rights Agreement, and upon
closing of the transactions contemplated by the Purchase Agreements, the Prior Rights Agreement is
hereby amended and restated in its entirety to read as set forth in this Agreement, and the
Company, the Founder, and the Investors hereby agree to be bound by the provisions hereof as the
sole agreement of the Company, the Founder and the Investors with respect to registration rights of
the Company’s securities and certain other rights, as set forth herein. The Series A Holders and
the Series B Holders hereby waive the Right of First Offer, including the notice requirements, set
forth in the Prior Rights Agreement with respect to the issuance of Series C Preferred Stock
pursuant to the Purchase Agreements and with respect to the issuance of warrants to purchase shares
of the Company’s capital stock being issued to Ring Power Corporation.

     1. Registration Rights. The Company and the Investors covenant and agree as follows:

          1.1 Definitions. For purposes of this Section 1:

               (a) The terms “register,” “registered,” and “registration” refer to a
registration effected by preparing and filing a registration statement or similar document in
compliance with the Securities Act of 1933, as amended (the “Securities Act”), and the
declaration or ordering of effectiveness of such registration statement or document;

               (b) The term “Registrable Securities” means (i) the shares of Common Stock issuable or
issued upon conversion of the Company’s Series A Preferred Stock, (ii) the shares of Common Stock
issuable or issued upon conversion of the Company’s Series B Preferred Stock, (iii) the shares of
Common Stock issuable or issued upon conversion of the Company’s Series C Preferred Stock, and (iv)
the shares of Common Stock issuable or issued upon conversion of the shares of the Company’s
Series A-1 Preferred Stock issued to the Founder (the “Founder’s Stock”), provided,
however, that for the purposes of Section 1.2, 1.4 or 1.13 the Founder’s Stock shall not be
deemed Registrable Securities and the Founder shall not be deemed a Holder, and (v) any other
shares of Common Stock of the Company issued as (or issuable upon the conversion or exercise of any
warrant, right or other security which is issued as) a dividend or other distribution with respect
to, or in exchange for or in replacement of, the shares listed in (i), (ii), (iii), and (iv);
provided, however, that the foregoing definition shall exclude in all cases any
Registrable Securities sold by a person in a transaction in which his or her rights under this
Agreement are not assigned. Notwithstanding the foregoing, Common Stock or other securities shall
only be treated as Registrable Securities if and so long as they have not been (A) sold to or
through a broker or dealer or underwriter in a public distribution or a public securities
transaction, or (B) sold in a transaction exempt from the registration and prospectus delivery
requirements of the Securities Act under Section 4(1) thereof so that all transfer restrictions,
and restrictive legends with respect thereto, if any, are removed upon the consummation of such
sale;

               (c) The number of shares of “Registrable Securities then outstanding” shall be
determined by the number of shares of Common Stock outstanding which are, and the

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number of shares of Common Stock issuable pursuant to then exercisable or convertible securities which are,
Registrable Securities;

               (d) The term “Holder” means any person owning or having the right to acquire
Registrable Securities or any assignee thereof in accordance with Section 1.12 of this Agreement;

               (e) The term “Form S-3” means such form under the Securities Act as in effect on the
date hereof or any successor form under the Securities Act that permits significant incorporation
by reference of the Company’s subsequent public filings under the Securities Exchange Act of 1934;

               (f) The term “SEC” means the Securities and Exchange Commission; and

               (g) The term “Qualified IPO” means a firm commitment underwritten public offering by
the Company of shares of its Common Stock pursuant to a registration statement under the Securities
Act, the public offering price of which is not less than $6.00 per share (appropriately adjusted
for any stock split, dividend, combination or other recapitalization) and which results in
aggregate cash proceeds to the Company of $20,000,000 (net of underwriting discounts and
commissions).

          1.2 Request for Registration.

               (a) If the Company shall receive at any time after the earlier of (i) August 28, 2010, or
(ii) six (6) months after the effective date of a Qualified IPO, a written request from the Holders
of a majority of the Registrable Securities then outstanding that the Company file a registration
statement under the Securities Act covering the registration of Registrable Securities then the
Company shall, within ten (10) days of the receipt thereof, give written notice of such request to
all Holders and shall, subject to the limitations of subsection 1.2(b), use its best efforts to
effect as soon as practicable, and in any event within 60 days of the receipt of such request, the
registration under the Securities Act of all Registrable Securities which the Holders request to be
registered within twenty (20) days of the mailing of such notice by the Company in accordance with
Section 3.4.

               (b) If the Holders initiating the registration request hereunder (“Initiating
Holders”) intend to distribute the Registrable Securities covered by their request by means of
an underwriting, they shall so advise the Company as a part of their request made pursuant to this
Section 1.2 and the Company shall include such information in the written notice referred to in
subsection 1.2(a). The underwriter will be selected by a majority in interest of the Initiating
Holders and shall be reasonably acceptable to the Company. In such event, the right of any Holder
to include his Registrable Securities in such registration shall be conditioned upon such Holder’s
participation in such underwriting and the inclusion of such Holder’s Registrable Securities in the
underwriting (unless otherwise mutually agreed by a majority in interest of the
Initiating Holders and such Holder) to the extent provided herein. All Holders proposing to
distribute their securities through such underwriting shall (together with the Company as provided
in subsection 1.5(e)) enter into an underwriting agreement in customary form with the

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underwriter or underwriters selected for such underwriting. Notwithstanding any other provision of this
Section 1.2, if the underwriter advises the Initiating Holders in writing that marketing factors
require a limitation of the number of shares to be underwritten, then the Initiating Holders shall
so advise all Holders of Registrable Securities which would otherwise be underwritten pursuant
hereto, and the number of shares of Registrable Securities that may be included in the underwriting
shall be allocated among all Holders thereof, including the Initiating Holders, in proportion (as
nearly as practicable) to the amount of Registrable Securities of the Company owned by each Holder;
provided, however, that the number of shares of Registrable Securities to be
included in such underwriting shall not be reduced unless all other securities are first entirely
excluded from the underwriting.

               (c) Notwithstanding the foregoing, if the Company shall furnish to Holders requesting a
registration statement pursuant to this Section 1.2, a certificate signed by the President of the
Company stating that in the good faith judgment of the Board of Directors of the Company, it would
be seriously detrimental to the Company and its stockholders for such registration statement to be
filed and it is therefore essential to defer the filing of such registration statement, the Company
shall have the right to defer such filing for a period of not more than 120 days after receipt of
the request of the Initiating Holders; provided, however, that the Company may not
utilize this right more than once in any twelve-month period.

               (d) In addition, the Company shall not be obligated to effect, or to take any action to
effect, any registration pursuant to this Section 1.2:

                    (i) After the Company has effected two (2) registrations pursuant to this Section 1.2 and such
registrations have been declared or ordered effective;

                    (ii) During the period starting with the date sixty (60) days prior to the Company’s good
faith estimate of the date of filing of, and ending on a date one hundred eighty (180) days after
the effective date of, a registration subject to Section 1.3 hereof; provided that the Company is
actively employing in good faith all reasonable efforts to cause such registration statement to
become effective; or

                    (iii) If the Initiating Holders propose to dispose of shares of Registrable Securities that
may be immediately registered on Form S-3 pursuant to a request made pursuant to Section 1.4 below.

          1.3 Company Registration. If (but without any obligation to do so) the Company
proposes to register (including for this purpose a registration effected by the Company for
stockholders other than the Holders) any of its stock under the Securities Act in connection with
the public offering of such securities solely for cash (other than a registration relating solely
to the sale of securities to participants in a Company stock plan or a transaction covered by
Rule 145 under the Securities Act, a registration in which the only stock being registered is
Common Stock issuable upon conversion of debt
securities which are also being registered, or any registration on any form which does not
include substantially the same information as would be required to be included in a registration
statement covering the sale of the Registrable Securities), the Company shall, at such time,
promptly give each Holder written notice of such registration. Upon the written request of each
Holder given within twenty (20) days after

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mailing of such notice by the Company in accordance with
Section 3.4, the Company shall, subject to the provisions of Section 1.8, cause to be registered
under the Securities Act all of the Registrable Securities that each such Holder has requested to
be registered.

          1.4 Form S-3 Registration. In case the Company shall receive from any Holder or
Holders of not less than thirty percent (30%) of the Registrable Securities then outstanding a
written request or requests that the Company effect a registration on Form S-3 and any related
qualification or compliance with respect to all or a part of the Registrable Securities owned by
such Holder or Holders, the Company will:

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

               (b) as soon as practicable, effect such registration and all such qualifications and
compliances as may be so requested and as would permit or facilitate the sale and distribution of
all or such portion of such Holder’s or Holders’ Registrable Securities as are specified in such
request, together with all or such portion of the Registrable Securities of any other Holder or
Holders joining in such request as are specified in a written request given within 15 days after
receipt of such written notice from the Company; provided, however, that the
Company shall not be obligated to effect any such registration, qualification or compliance,
pursuant to this Section 1.4: (i) if Form S-3 is not available for such offering by the Holders;
(ii) if the Holders, together with the holders of any other securities of the Company entitled to
inclusion in such registration, propose to sell Registrable Securities and such other securities
(if any) at an aggregate price to the public (net of any underwriters’ discounts or commissions) of
less than $500,000; (iii) if the Company shall furnish to the Holders a certificate signed by the
President of the Company stating that in the good faith judgment of the Board of Directors of the
Company, it would be seriously detrimental to the Company and its stockholders for such Form S-3
Registration to be effected at such time, in which event the Company shall have the right to defer
the filing of the Form S-3 registration statement for a period of not more than 120 days after
receipt of the request of the Holder or Holders under this Section 1.4; provided,
however, that the Company shall not utilize this right more than once in any twelve month
period; (iv) if the Company has, within the twelve (12) month period preceding the date of such
request, already effected two registrations on Form S-3 for the Holders pursuant to this
Section 1.4; (v) in any particular jurisdiction in which the Company would be required to qualify
to do business or to execute a general consent to service of process in effecting such
registration, qualification or compliance; or (vi) during the period ending one hundred eighty
(180) days after the effective date of a registration statement subject to Section 1.3.

               (c) Subject to the foregoing, the Company shall file a registration statement covering the
Registrable Securities and other securities so requested to be registered as soon as practicable
after receipt of the request or requests of the Holders. Registrations effected
pursuant to this Section 1.4 shall not be counted as demands for registration or registrations
effected pursuant to Sections 1.2 or 1.3, respectively.

          1.5 Obligations of the Company. Whenever required under this Section 1 to effect the
registration of any Registrable Securities, the Company shall, as expeditiously as reasonably
possible:

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               (a) Prepare and file with the SEC a registration statement with respect to such Registrable
Securities and use its best efforts to cause such registration statement to become effective, and,
upon the request of the Holders of a majority of the Registrable Securities registered thereunder,
keep such registration statement effective for up to one hundred twenty (120) days.

               (b) Prepare and file with the SEC such amendments and supplements to such registration
statement and the prospectus used in connection with such registration statement as may be
necessary to comply with the provisions of the Securities Act with respect to the disposition of
all securities covered by such registration statement for up to one hundred eighty (180) days.

               (c) Furnish to the Holders such numbers of copies of a prospectus, including a preliminary
prospectus, in conformity with the requirements of the Securities Act, and such other documents as
they may reasonably request in order to facilitate the disposition of Registrable Securities owned
by them.

               (d) Use its best efforts to register and qualify the securities covered by such registration
statement under such other securities or Blue Sky laws of such jurisdictions as shall be reasonably
requested by the Holders, provided that the Company shall not be required in connection
therewith or as a condition thereto to qualify to do business or to file a general consent to
service of process in any such states or jurisdictions.

               (e) In the event of any underwritten public offering, enter into and perform its obligations
under an underwriting agreement, in usual and customary form, with the managing underwriter of such
offering. Each Holder participating in such underwriting shall also enter into and perform its
obligations under such an agreement.

               (f) Notify each Holder of Registrable Securities covered by such registration statement at any
time when a prospectus relating thereto is required to be delivered under the Securities Act of the
happening of any event as a result of which the prospectus included in such registration statement,
as then in effect, includes an untrue statement of a material fact or omits to state a material
fact required to be stated therein or necessary to make the statements therein not misleading in
the light of the circumstances then existing, such obligation to continue for one hundred twenty
(120) days.

               (g) Cause all such Registrable Securities registered pursuant hereunder to be listed on each
securities exchange on which similar securities issued by the Company are then listed.

               (h) Provide a transfer agent and registrar for all Registrable Securities registered pursuant
hereunder and a CUSIP number for all such Registrable Securities, in each case not later than the
effective date of such registration.

               (i) Use its best efforts to furnish, at the request of any Holder requesting registration of
Registrable Securities pursuant to this Section 1, on the date that such Registrable Securities are
delivered to the underwriters for sale in connection with a registration

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pursuant to this Section 1, if such securities are being sold through underwriters, or, if such securities are not
being sold through underwriters, on the date that the registration statement with respect to such
securities becomes effective, (i) an opinion, dated such date, of the counsel representing the
Company for the purposes of such registration, in form and substance as is customarily given to
underwriters in an underwritten public offering, addressed to the underwriters, if any, and to the
Holders requesting registration of Registrable Securities and (ii) a letter dated such date, from
the independent certified public accountants of the Company, in form and substance as is
customarily given by independent certified public accountants to underwriters in an underwritten
public offering, addressed to the underwriters, if any, and to the Holders requesting registration
of Registrable Securities.

          1.6 Furnish Information. It shall be a condition precedent to the obligations of the
Company to take any action pursuant to this Section 1 with respect to the Registrable Securities of
any selling Holder that such Holder shall furnish to the Company such information regarding itself,
the Registrable Securities held by it, and the intended method of disposition of such securities as
shall be required to effect the registration of such Holder’s Registrable Securities. The Company
shall have no obligation with respect to any registration requested pursuant to Section 1.2 or
Section 1.4 of this Agreement if, as a result of the application of the preceding sentence, the
number of shares or the anticipated aggregate offering price of the Registrable Securities to be
included in the registration does not equal or exceed the number of shares or the anticipated
aggregate offering price required to originally trigger the Company’s obligation to initiate such
registration as specified in subsection 1.2(a) or subsection 1.4(b)(ii), whichever is applicable.

          1.7 Expenses of Registration.

               (a) Demand Registration. All expenses other than underwriting discounts and
commissions incurred in connection with registrations, filings or qualifications pursuant to
Section 1.2, including (without limitation) all registration, filing and qualification fees,
printers’ and accounting fees, fees and disbursements of counsel for the Company, and the
reasonable fees and disbursements (not to exceed $15,000) of one counsel for the selling Holders
selected by them with the approval of the Company, which approval shall not be unreasonably
withheld, shall be borne by the Company; provided, however, that the Company shall
not be required to pay for any expenses of any registration proceeding begun pursuant to
Section 1.2 if the registration request is subsequently withdrawn at the request of the Holders of
a majority of the Registrable Securities to be registered (in which case all participating Holders
shall bear such expenses), unless the Holders of a majority of the Registrable Securities agree to
forfeit their right to one demand registration pursuant to Section 1.2.

               (b) Company Registration. All expenses other than underwriting discounts and
commissions incurred in connection with registrations, filings or qualifications of Registrable
Securities pursuant to Section 1.3 for each Holder (which right may be assigned as provided in
Section 1.12), including (without limitation) all registration, filing, and qualification fees,
printers’ and accounting fees, fees and disbursements of counsel for the Company and the reasonable
fees and disbursements (not to exceed $15,000) of one counsel for the selling Holder

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or Holders selected by them with the approval of the Company, which approval shall not be unreasonably
withheld, shall be borne by the Company.

               (c) Registration on Form S-3. All expenses incurred in connection with a registration
requested pursuant to Section 1.4, including (without limitation) all registration, filing,
qualification, printers’ and accounting fees and the reasonable fees and disbursements (not to
exceed $15,000) of one counsel for the selling Holder or Holders selected by them with the approval
of the Company, which approval shall not be unreasonably withheld, and counsel for the Company, and
any underwriters’ discounts or commissions associated with Registrable Securities, shall be borne
by the Company.

          1.8 Underwriting Requirements. In connection with any offering involving an
underwriting of shares of the Company’s capital stock, the Company shall not be required under
Section 1.3 to include any of the Holders’ securities in such underwriting unless they accept the
terms of the underwriting as agreed upon between the Company and the underwriters selected by it
(or by other persons entitled to select the underwriters), and then only in such quantity as the
underwriters determine in their sole discretion will not jeopardize the success of the offering by
the Company. If the total amount of securities, including Registrable Securities, requested by
stockholders to be included in such offering exceeds the amount of securities sold other than by
the Company that the underwriters determine in their sole discretion is compatible with the success
of the offering, then the Company shall be required to include in the offering only that number of
such securities, including Registrable Securities, which the underwriters determine in their sole
discretion will not jeopardize the success of the offering (the securities so included to be
apportioned pro rata among the selling stockholders according to the total amount of securities
entitled to be included therein owned by each selling stockholder or in such other proportions as
shall mutually be agreed to by such selling stockholders) but in no event shall (i) the amount of
securities of the selling Holders included in the offering be reduced below twenty-five percent
(25%) of the total amount of securities included in such offering, unless such offering is the
initial public offering of the Company’s securities, in which case, the selling stockholders may be
excluded if the underwriters make the determination described above and no other stockholder’s
securities are included or (ii) any securities held by a Founder be included if any securities held
by any selling Holder are excluded. For purposes of the preceding parenthetical concerning
apportionment, for any selling stockholder which is a holder of Registrable Securities and which is
a partnership or corporation, the partners, retired partners and stockholders of such holder, or
the estates and family members of any such partners and retired partners and any trusts for the
benefit of any of the foregoing persons shall be deemed to be a single “selling
stockholder,” and any pro-rata reduction with respect to such “selling stockholder” shall be
based upon the aggregate amount of shares carrying registration rights owned by all entities and
individuals included in such “selling stockholder,” as defined in this sentence.

          1.9 Delay of Registration. No Holder shall have any right to obtain or seek an
injunction restraining or otherwise delaying any such registration as the result of any controversy
that might arise with respect to the interpretation or implementation of this Section 1.

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          1.10 Indemnification. In the event any Registrable Securities are included in a
registration statement under this Section 1:

               (a) To the extent permitted by law, the Company will indemnify and hold harmless each Holder,
any underwriter (as defined in the Securities Act) for such Holder and each person, if any, who
controls such Holder or underwriter within the meaning of the Securities Act or the Securities
Exchange Act of 1934, as amended (the “Exchange Act”), against any losses, claims, damages,
or liabilities (joint or several) to which they may become subject under the Securities Act, the
Exchange Act or other federal or state law, insofar as such losses, claims, damages, or liabilities
(or actions in respect thereof) arise out of or are based upon any of the following statements,
omissions or violations (collectively a “Violation”): (i) any untrue statement or alleged
untrue statement of a material fact contained in such registration statement, including any
preliminary prospectus or final prospectus contained therein or any amendments or supplements
thereto, (ii) the omission or alleged omission to state therein a material fact required to be
stated therein, or necessary to make the statements therein not misleading, or (iii) any violation
or alleged violation by the Company of the Securities Act, the Exchange Act, any state securities
law or any rule or regulation promulgated under the Securities Act, the Exchange Act or any state
securities law; and the Company will pay to each such Holder, underwriter or controlling person, as
incurred, any legal or other expenses reasonably incurred by them in connection with investigating
or defending any such loss, claim, damage, liability, or action; provided, however,
that the indemnity agreement contained in this subsection 1.10(a) shall not apply to amounts paid
in settlement of any such loss, claim, damage, liability, or action if such settlement is effected
without the consent of the Company (which consent shall not be unreasonably withheld), nor shall
the Company be liable to any Holder, underwriter or controlling person for any such loss, claim,
damage, liability, or action to the extent that it arises out of or is based upon a Violation which
occurs in reliance upon and in conformity with written information furnished expressly for use in
connection with such registration by any such Holder, underwriter or controlling person.

               (b) To the extent permitted by law, each selling Holder will indemnify and hold harmless the
Company, each of its directors, each of its officers who has signed the registration statement,
each person, if any, who controls the Company within the meaning of the Securities Act, any
underwriter, any other Holder selling securities in such registration statement and any controlling
person of any such underwriter or other Holder, against any losses, claims, damages, or liabilities
(joint or several) to which any of the foregoing persons may become subject, under the Securities
Act, the Exchange Act or other federal or state law, insofar as such losses, claims, damages, or
liabilities (or actions in respect thereto) arise out of or are based upon any Violation, in each
case to the extent (and only to the extent) that such Violation occurs in reliance upon and in
conformity with written information furnished by such Holder expressly for use in connection with
such registration; and each such Holder will pay, as incurred, any legal or other expenses
reasonably incurred by any person intended to be indemnified pursuant to this
subsection 1.10(b), in connection with investigating or defending any such loss, claim,
damage, liability, or action; provided, however, that the indemnity agreement
contained in this subsection 1.10(b) shall not apply to amounts paid in settlement of any such
loss, claim, damage, liability or action if such settlement is effected without the consent of the
Holder, which consent shall not be unreasonably withheld; provided, that in no event shall
any indemnity under this

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subsection 1.10(b) exceed the net proceeds from the offering received by
such Holder, except in the case of willful fraud by such Holder.

               (c) Promptly after receipt by an indemnified party under this Section 1.10 of notice of the
commencement of any action (including any governmental action), such indemnified party will, if a
claim in respect thereof is to be made against any indemnifying party under this Section 1.10,
deliver to the indemnifying party a written notice of the commencement thereof and the indemnifying
party shall have the right to participate in, and, to the extent the indemnifying party so desires,
jointly with any other indemnifying party similarly noticed, to assume the defense thereof with
counsel mutually satisfactory to the parties; provided, however, that an
indemnified party (together with all other indemnified parties which may be represented without
conflict by one counsel) shall have the right to retain one separate counsel, with the reasonable
fees and expenses to be paid by the indemnifying party, if representation of such indemnified party
by the counsel retained by the indemnifying party would be inappropriate due to actual or potential
differing interests between such indemnified party and any other party represented by such counsel
in such proceeding. The failure to deliver written notice to the indemnifying party within a
reasonable time of the commencement of any such action, if prejudicial to its ability to defend
such action, shall relieve such indemnifying party of any liability to the indemnified party under
this Section 1.10, but the omission so to deliver written notice to the indemnifying party will not
relieve it of any liability that it may have to any indemnified party otherwise than under this
Section 1.10.

               (d) If the indemnification provided for in this Section 1.10 is held by a court of competent
jurisdiction to be unavailable to an indemnified party with respect to any loss, liability, claim,
damage or expense referred to therein, then the indemnifying party, in lieu of indemnifying such
indemnified party hereunder, shall contribute to the amount paid or payable by such indemnified
party as a result of such loss, liability, claim, damage, or expense in such proportion as is
appropriate to reflect the relative fault of the indemnifying party on the one hand and of the
indemnified party on the other in connection with the statements or omissions that resulted in such
loss, liability, claim, damage or expense as well as any other relevant equitable considerations;
provided, that in no event shall any contribution by a Holder under this Subsection 1.10(d)
exceed the net proceeds from the offering received by such Holder, except in the case of willful
fraud by such Holder. The relative fault of the indemnifying party and of the indemnified party
shall be determined by reference to, among other things, whether the untrue or alleged untrue
statement of a material fact or the omission to state a material fact relates to information
supplied by the indemnifying party or by the indemnified party and the parties’ relative intent,
knowledge, access to information, and opportunity to correct or prevent such statement or omission.

               (e) Notwithstanding the foregoing, to the extent that the provisions on indemnification and
contribution contained in the underwriting agreement entered into in
connection with the underwritten public offering are in conflict with the foregoing
provisions, the provisions in the underwriting agreement shall control.

-10-

 

               (f) The obligations of the Company and Holders under this Section 1.10 shall survive the
completion of any offering of Registrable Securities in a registration statement under this
Section 1, and otherwise.

          1.11 Reports Under Securities Exchange Act of 1934. With a view to making available
to the Holders the benefits of Rule 144 promulgated under the Securities Act and any other rule or
regulation of the SEC that may at any time permit a Holder to sell securities of the Company to the
public without registration or pursuant to a registration on Form S-3, the Company agrees to:

               (a) make and keep public information available, as those terms are understood and defined in
SEC Rule 144, at all times after ninety (90) days after the effective date of the first
registration statement filed by the Company for the offering of its securities to the general
public so long as the Company remains subject to the periodic reporting requirements under
Sections 13 or 15(d) of the Exchange Act;

               (b) take such action, including the voluntary registration of its Common Stock under
Section 12 of the Exchange Act, as is necessary to enable the Holders to utilize Form S-3 for the
sale of their Registrable Securities, such action to be taken as soon as practicable after the end
of the fiscal year in which the first registration statement filed by the Company for the offering
of its securities to the general public is declared effective;

               (c) file with the SEC in a timely manner all reports and other documents required of the
Company under the Securities Act and the Exchange Act; and

               (d) furnish to any Holder, so long as the Holder owns any Registrable Securities, forthwith
upon request (i) a written statement by the Company that it has complied with the reporting
requirements of SEC Rule 144 (at any time after ninety (90) days after the effective date of the
first registration statement filed by the Company), the Securities Act and the Exchange Act (at any
time after it has become subject to such reporting requirements), or that it qualifies as a
registrant whose securities may be resold pursuant to Form S-3 (at any time after it so qualifies),
(ii) a copy of the most recent annual or quarterly report of the Company and such other reports and
documents so filed by the Company, and (iii) such other information as may be reasonably requested
in availing any Holder of any rule or regulation of the SEC which permits the selling of any such
securities without registration or pursuant to such form.

          1.12 Assignment of Registration Rights. The rights to cause the Company to register
Registrable Securities pursuant to this Section 1 may be assigned (but only with all related
obligations) by a Holder to a transferee or assignee of at least 200,000 shares (appropriately
adjusted for any stock split, dividend, combination or other recapitalization) of such securities,
provided the Company is, within a reasonable time after such transfer, furnished with
written notice of the name and address of such transferee or assignee and the securities with
respect to which such registration
rights are being assigned; and provided, further, that such assignment shall
be effective only if immediately following such transfer the further disposition of such securities
by the transferee or assignee is restricted under the Securities Act. For the purposes of
determining the number of shares of Registrable Securities held by a transferee or assignee, the
holdings of transferees and assignees of a partnership who are partners or retired

-11-

 

partners of such
partnership (including spouses and ancestors, lineal descendants and siblings of such partners or
spouses who acquire Registrable Securities by gift, will or intestate succession) shall be
aggregated together and with the partnership; provided that all assignees and transferees who would
not qualify individually for assignment of registration rights shall have a single attorney-in-fact
for the purpose of exercising any rights, receiving notices or taking any action under Section 1.

          1.13 Limitations on Subsequent Registration Rights. From and after the date of this
Agreement, the Company shall not, without the prior written consent of the Holders of a majority of
the outstanding Registrable Securities, enter into any agreement with any holder or prospective
holder of any securities of the Company which would allow such holder or prospective holder (a) to
include such securities in any registration filed under Section 1.2 hereof, unless under the terms
of such agreement, such holder or prospective holder may include such securities in any such
registration only to the extent that the inclusion of his securities will not reduce the amount of
the Registrable Securities of the Holders which is included or (b) to make a demand registration
which could result in such registration statement being declared effective prior to the earlier of
either of the dates set forth in subsection 1.2(a) or within one hundred twenty (120) days of the
effective date of any registration effected pursuant to Section 1.2.

          1.14 “Market Stand-Off” Agreement.

               (a) Market-Standoff Period; Agreement. In connection with the initial public offering
of the Company’s securities and upon request of the Company or the underwriters managing such
offering of the Company’s securities, each Holder agrees not to sell, make any short sale of, loan,
grant any option for the purchase of, or otherwise dispose of any securities of the Company (other
than those included in the registration) without the prior written consent of the Company or such
underwriters, as the case may be, for such period of time (not to exceed 180 days) from the
effective date of such registration as may be requested by the Company or such managing
underwriters and to execute an agreement reflecting the foregoing as may be requested by the
underwriters at the time of the Company’s initial public offering, provided all then current
officers, directors and holders of more than 1% of the Company’s voting stock agree to be bound by
similar restrictions.

               (b) Limitations. The obligations described in Section 1.14(a) shall apply only if all
officers and directors of the Company enter into similar agreements, and shall not apply to a
registration relating solely to employee benefit plans, or to a registration relating solely to a
transaction pursuant to Rule 145 under the Securities Act.

               (c) Stop-Transfer Instructions. In order to enforce the foregoing covenants, the
Company may impose stop-transfer instructions with respect to the securities of
each Holder (and the securities of every other person subject to the restrictions in Section
1.14(a)).

               (d) Transferees Bound. Each Holder agrees that it will not transfer securities of the
Company unless each transferee agrees in writing to be bound by all of the provisions of this
Section 1.14, provided that this Section 1.14(d) shall not apply to transfers

-12-

 

pursuant to a registration statement or transfers after the twelve-month anniversary of the effective date of the
Company’s initial registration statement subject to this Section 1.14.

          1.15 Termination of Registration Rights. No Holder shall be entitled to exercise any
right provided for in this Section 1 after the earlier of (i) three (3) years following the
consummation of a Qualified IPO, (ii) such time as Rule 144 or another similar exemption under the
Securities Act is available for the sale of all of such Holder’s shares during a three (3)-month
period without registration, or (iii) at such time as such Holder (excluding Randall) holds
Registrable Securities constituting less than two percent (2%) of the outstanding voting stock of
the Company.

     2. Covenants of the Company.

          2.1 Delivery of Financial Statements. The Company shall deliver to Randall, so long
as Randall owns any shares, and each other Holder of at least 200,000 shares (appropriately
adjusted for any stock split, dividend, combination or other recapitalization) of Registrable
Securities (excluding for purposes of subsections (c) and (d) below any Common Stock issued to
Randall):

               (a) as soon as practicable, but in any event within ninety (90) days after the end of each
fiscal year of the Company, an income statement for such fiscal year, a balance sheet of the
Company and statement of stockholder’s equity as of the end of such year, and a statement of cash
flows for such year, such year-end financial reports to be in reasonable detail, prepared in
accordance with generally accepted accounting principles (“GAAP”), and audited and
certified by an independent public accounting firm of nationally recognized standing selected by
the Company;

               (b) as soon as practicable, but in any event within thirty (30) days after the end of each of
the first three (3) quarters of each fiscal year of the Company, an unaudited profit or loss
statement, a statement of cash flows for such fiscal quarter and an unaudited balance sheet as of
the end of such fiscal quarter;

               (c) within thirty (30) days of the end of each month, an unaudited income statement and a
statement of cash flows and balance sheet for and as of the end of such month, in reasonable
detail;

               (d) as soon as practicable, but in any event thirty (30) days prior to the end of each fiscal
year, a budget and business plan for the next fiscal year, prepared on a monthly basis, and, as
soon as prepared, any other budgets or revised budgets prepared by the Company; and

               (e) with respect to the financial statements called for in subsections (b) and (c) of this
Section 2.1, an instrument executed by the Chief Financial Officer or President of the Company and
certifying that such financials were prepared in accordance with GAAP consistently applied with
prior practice for earlier periods (with the exception of footnotes that may be required by GAAP)
and fairly present the financial condition of the Company and its results of operation for the
period specified, subject to year-end audit adjustment, provided that

-13-

 

the foregoing shall not restrict the right of the Company to change its accounting principles consistent with GAAP, if the
Board of Directors determines that it is in the best interest of the Company to do so.

          2.2 Inspection. The Company shall permit each Holder of at least 200,000 shares
(appropriately adjusted for any stock split, dividend, combination or other recapitalization) of
Registrable Securities (excluding for purposes of this Section 2.2 Common Stock issued to Randall)
at such Holder’s expense, to visit and inspect the Company’s properties, to examine its books of
account and records and to discuss the Company’s affairs, finances and accounts with its officers,
all at such reasonable times as may be requested by the Investor; provided,
however, that the Company shall not be obligated pursuant to this Section 2.2 to provide
access to any information which it reasonably considers to be a trade secret or similar
confidential information; provided further, however, that nothing in this Section 2.2 shall
be construed to limit the rights of any Holder under Section 220 of the Delaware Corporation Law to
inspect the Company’s books and records for a proper purpose as contemplated by that statute.

          2.3 Right of First Offer. Subject to the terms and conditions specified in this
Section 2.3, the Company hereby grants to each Major Investor (as hereinafter defined) a right of
first offer with respect to future sales by the Company of its Shares (as hereinafter defined).
For purposes of this Section 2.3, a “Major Investor” shall mean any person who holds at
least 200,000 shares of the Series A Preferred Stock, Series B Preferred Stock, and/or Series C
Preferred Stock (or the Common Stock issued upon conversion thereof) (appropriately adjusted for
any stock split, dividend, combination or other recapitalization). For purposes of this
Section 2.3, Major Investor includes any general partners and affiliates of a Major Investor. A
Major Investor who chooses to exercise the right of first offer may designate as purchasers under
such right itself or its partners or affiliates in such proportions as it deems appropriate.

          Each time the Company proposes to offer any shares of, or securities convertible into or
exercisable for any shares of, any class of its capital stock (“Shares”), the Company shall
first make an offering of such Shares to each Major Investor in accordance with the following
provisions:

               (a) The Company shall deliver a notice by certified mail (“Notice”) to the Major
Investors stating (i) its bona fide intention to offer such Shares, (ii) the number of such Shares
to be offered, and (iii) the price and terms, if any, upon which it proposes to offer such Shares.

               (b) Within 15 calendar days after delivery of the Notice, the Major Investor may elect to
purchase or obtain, at the price and on the terms specified in the Notice, up to that portion of
such Shares which equals the proportion that the number of shares of Common Stock issued and held,
or issuable upon conversion and exercise of all convertible or exercisable securities then held, by
such Major Investor bears to the total number of shares of Common Stock outstanding as of the date
hereof (assuming full conversion and exercise of all convertible or exercisable securities). Such
purchase shall be completed at the same closing as that of any third party purchasers or at an
additional closing thereunder. The Company shall promptly, in writing, inform each Major Investor
that purchases all the shares available to it (each, a “Fully-Exercising Investor”) of any
other Major Investor’s failure to do likewise. During the ten

-14-

 

(10)-day period commencing after receipt of such information, each Fully-Exercising Investor shall be entitled to obtain that
portion of the Shares for which Major Investors were entitled to subscribe but which were not
subscribed for by the Major Investors that is equal to the proportion that the number of shares of
Common Stock issued and held, or issuable upon conversion and exercise of all convertible or
exercisable securities then held, by such Fully-Exercising Investor bears to the total number of
shares of Common Stock then outstanding (assuming full conversion and exercise of all convertible
or exercisable securities).

               (c) The Company may, during the 45-day period following the expiration of the period provided
in subsection 2.3(b) hereof, offer the remaining unsubscribed portion of the Shares to any person
or persons at a price not less than, and upon terms no more favorable to the offeree than those
specified in the Notice. If the Company does not enter into an agreement for the sale of the
Shares within such period, or if such agreement is not consummated within 60 days of the execution
thereof, the right provided hereunder shall be deemed to be revived and such Shares shall not be
offered unless first reoffered to the Major Investors in accordance herewith.

               (d) The right of first offer in this paragraph 2.3 shall not be applicable (i) to the issuance
or sale of Common Stock (or options therefor) to employees, consultants and directors, pursuant to
plans or agreements approved by the Board of Directors, (ii) to or after consummation of a
Qualified IPO, (iii) to the issuance of securities pursuant to the conversion or exercise of
convertible or exercisable securities, (iv) to the issuance of securities in connection with a bona
fide business acquisition of or by the Company, whether by merger, consolidation, sale of assets,
sale or exchange of stock or otherwise, (v) to the issuance of securities to financial institutions
or lessors in connection with commercial credit arrangements, equipment financings, or similar
transactions approved by the board of Directors, (vi) to the issuance or sale of the Series A
Preferred Stock, (vii) to the issuance of securities pursuant to stock splits, stock dividends or
like transactions, (viii) to the issuance of securities pursuant to currently outstanding options,
warrants, notes or other rights to acquire securities of the Company, or (ix) to the issuance of
securities that, with unanimous approval of the Board of Directors of the Company, are not offered
to any existing stockholder of the Company. In addition to the foregoing, the right of first offer
in this paragraph 2.3 shall not be applicable with respect to any Major Investor and any subsequent
securities issuance, if (i) at the time of such subsequent securities issuance, the Major Investor
is not an “accredited investor,” as that term is then defined in Rule 501(a) under the Securities
Act, and (ii) such subsequent securities issuance is otherwise being offered only to accredited
investors.

          2.4 Termination of Covenants.

               (a) The covenants set forth in Sections 2.1 through Section 2.3 shall terminate as to each
Holder and be of no further force or effect (i) immediately prior to the consummation of a
Qualified IPO, or (ii) upon termination of the entire Agreement upon a change in control of the
Company, as provided in Section 3.1.

               (b) The covenants set forth in Sections 2.1 and 2.2 shall terminate as to each Holder and be
of no further force or effect when the Company first becomes subject to

-15-

 

the periodic reporting requirements of Sections 13 or 15(d) of the Exchange Act, if this occurs earlier than the events
described in Section 2.5(a) above.

     3. Miscellaneous.

          3.1 Termination of Entire Agreement Upon Change of Control. This Agreement shall
terminate, and have no further force and effect, when the Company shall sell, convey, or otherwise
dispose of all or substantially all of its property or business or merge into or consolidate with
any other corporation (other than a wholly-owned subsidiary corporation) or effect any other
transaction or series of related transactions in which more than 50% of the voting power of the
Company is disposed of, provided that this Agreement shall not be terminated following a
merger effected solely for the purpose of changing the domicile of the Company.

          3.2 Successors and Assigns. Except as otherwise provided in this Agreement, the terms
and conditions of this Agreement shall inure to the benefit of and be binding upon the respective
permitted successors and assigns of the parties (including transferees of any of the Series A,
Series B, or Series C Preferred Stock or any Common Stock issued upon conversion thereof). Nothing
in this Agreement, express or implied, is intended to confer upon any party other than the parties
hereto or their respective successors and assigns any rights, remedies, obligations, or liabilities
under or by reason of this Agreement, except as expressly provided in this Agreement.

          3.3 Amendments and Waivers. Any term of this Agreement may be amended or waived only
with the written consent of the Company and the holders of at least two-thirds (2/3rds) of the
Registrable Securities then outstanding, not including the Founder’s Stock; provided that if such
amendment has the effect of affecting a series of Preferred Stock in a manner different than
another series of Preferred Stock, then such amendment shall require the consent of the holder or
holders of at least a majority of the shares of the series of Preferred Stock so affected or in the
case of a particular Investor if the rights of such Investor are changed under this Agreement in a
manner different from that of the other Investors, then such amendment shall require the consent of
such Investor; and, provided further that if such amendment has the effect of affecting the
Founder’s Stock (i) in a manner different than securities issued to the Investors and (ii) in a
manner adverse to the interests of the holders of the Founder’s Stock, then such amendment shall
require the consent of the holder or holders of a majority of the Founder’s Stock. Notwithstanding
the foregoing, this
Agreement may be amended with only the written consent of the Company for the sole purpose of
including additional purchasers of Series C Preferred Stock as “Investors” and “Holders.” Any
amendment or waiver effected in accordance with this paragraph shall be binding upon each party to
the Agreement, whether or not such party has signed such amendment or waiver, each future holder of
all such Registrable Securities, and the Company.

          3.4 Notices. Unless otherwise provided, any notice required or permitted by this
Agreement shall be in writing and shall be deemed sufficient upon delivery, (i) upon delivery when
delivered personally or (ii) two (2) business days following deposit for delivery

-16-

 

by overnight courier with Federal Express or another internationally recognized courier or (iii) upon confirmed
facsimile on a business day (or if the day in question is not a business day, then at local time
the start of the following business day), and addressed to the party to be notified at such party’s
address or fax number as set forth on Exhibit A hereto or as subsequently modified by written
notice. A “business day” shall be a day on which banks are open for business in the location on
record of both the sender and the receiver of the notice.

          3.5 Severability. If one or more provisions of this Agreement are held to be
unenforceable under applicable law, the parties agree to renegotiate such provision in good faith.
In the event that the parties cannot reach a mutually agreeable and enforceable replacement for
such provision, then (a) such provision shall be excluded from this Agreement, (b) the balance of
the Agreement shall be interpreted as if such provision were so excluded and (c) the balance of the
Agreement shall be enforceable in accordance with its terms.

          3.6 Governing Law. This Agreement and all acts and transactions pursuant hereto shall
be governed, construed and interpreted in accordance with the laws of the State of California,
without giving effect to principles of conflicts of laws.

          3.7 Counterparts. This Agreement may be executed 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.

          3.8 Titles and Subtitles. The titles and subtitles used in this Agreement are used
for convenience only and are not to be considered in construing or interpreting this Agreement.

          3.9 Aggregation of Stock. All shares of the Preferred Stock held or acquired by
affiliated entities or persons shall be aggregated together for the purpose of determining the
availability of any rights under this Agreement.

          3.10 Observer Rights. So long as European Founders Fund GmbH or one of its
affiliates (collectively, “EFF”) holds at least 100,000 shares of Registrable
Securities (as adjusted for stock splits, recapitalizations, dividends and the like), the
Company shall allow one (1) representative designated by EFF (the “EFF Observer”)
to attend all meetings of the Company’s Board of Directors in a nonvoting capacity, and in
connection therewith, the Company shall give
the EFF Observer copies of all notices, minutes, consents and other materials,
financial or otherwise, which the Company provides to its Board of Directors; provided,
however, that the Company reserves the right to exclude the EFF Observer from access to any
material or meeting or portion thereof if the Company believes upon advice of counsel that
such exclusion is reasonably necessary to preserve the attorney-client privilege, to
protect highly confidential information or for other similar reasons. The decision of the
Company’s Board of Directors with respect to the privileged or confidential nature of such
information shall be final and binding.

-17-

 

[Signature Page Follows]

-18-

 

     The parties have executed this Third Amended and Restated Investors’ Rights Agreement as of
the date first above written.

	 	 	 	 	 	 	 
	 	 	COMPANY:	 	 
	 
	 	 	 	 	 	 
	 	 	IRONPLANET.COM, INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:  /s/ Gregory J. Owens
 

        Gregory J. Owens, President	 	 
	 
	 	 	 	 	 	 
	 

	 	Address:
	 	4695 Chabot Drive, Suite 102	 	 
	 

	 	 	 	Pleasanton, CA 94588	 	 
	 
	 	 	 	 	 	 
	 	 	FOUNDER:	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	 	 	 
	 	 	Reza Bundy Saadlou	 	 
	 
	 	 	 	 	 	 
	 

	 	Address:	 	 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	KPCB Holdings, Inc., as nominee	 	 
	 
	 	 	 	 	 	 
	 

	 	By:  /s/ Ted Schlein 

                  (Signature)	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 		 	 
	 
	 	Name:	 	Ted Schlein	 	 
	 
	 	 	 	 	 	 
	 
	 	 	 	    (print)	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	          	 	 
	 
	 	Title:	 	/s/ Senior Vice President	 	 
	 
	 	 	 	 	 	 
	 

	 	 	 	 	 	 
	 	 	Address:	 	 
	 	 	2750 Sand Hill Road	 	 
	 	 	Menlo Park, CA 94025	 	 

SIGNATURE PAGE TO IRONPLANET.COM, INC. THIRD AMENDED AND

RESTATED INVESTORS’ RIGHTS AGREEMENT

 

 

     The parties have executed this Third Amended and Restated Investors’ Rights Agreement as of
the date first above written.

	 	 	 	 	 	 	 
	 	 	ACCEL VII L.P.	 	 
	 	 	By: Accel VII Associates L.L.C.	 	 
	 	 	Its General Partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Tracy L. Sedlock
 

Attorney-in-Fact
	 	 
	 
	 	 	 	 	 	 
	 

	 	Name: Tracy Sedlock
	 	 
	 
	 	 	 	 	 	 
	 	 	ACCEL INTERNET FUND III L.P.	 	 
	 	 	By: Accel Internet Fund III Associates L.L.C.	 	 
	 	 	Its General Partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Tracy L. Sedlock	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Attorney-in-Fact	 	 
	 
	 	 	 	 	 	 
	 

	 	Name: Tracy Sedlock	 	 
	 
	 	 	 	 	 	 
	 	 	ACCEL INVESTORS ’99 L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Tracy L. Sedlock	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Attorney-in-Fact	 	 
	 
	 	 	 	 	 	 
	 

	 	Name: Tracy Sedlock
	 	 
	 
	 	 	 	 	 	 
	 	 	ACP FAMILY PARTNERSHIP L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Tracy L. Sedlock	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Agent	 	 
	 
	 	 	 	 	 	 
	 

	 	Name: Tracy Sedlock
	 	 

SIGNATURE PAGE TO IRONPLANET.COM, INC. THIRD AMENDED AND

RESTATED INVESTORS’ RIGHTS AGREEMENT

 

 

     The parties have executed this Third Amended and Restated Investors’ Rights Agreement as of
the date first above written.

	 	 	 	 	 	 	 
	 	 	CATERPILLAR INC.	 	 
	 
	 	 	 	 	 	 
	 
	 	By:	/s/ Tom Frautschy	 	 
	 
	 	 	 	 	 
	 
	 	 	 	 	 	 
	 
	 	Name:	 	Tom Frautschy	 	 
	 
	 	 	 	 	 	 
	 

	 	 	 	(Print)	 	 
	 
	 	 	 	 	 	 
	 
	 	Address:	 	2120 West End Ave.	 	 
	 
	 	 	 	 	 	 
	 

	 	 	 	Nashville, Tennessee 37203 	 	 
	 
	 	 	 	 	 	 
	 
	 	 	 	 
 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	KOMATSU AMERICA CORP.	 	 
	 
	 	 	 	 	 	 
	 
	 	By:	/s/ Gary Kasbeer	 	 
	 
	 	 	 	 	 
	 
	 	 	 	 	 	 
	 

	 	Name:
	 	Gary Kasbeer	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	(Print)	 	 
	 
	 	 	 	 	 	 
	 
	 	Address:	 	1701 E. Golf Rd.	 	 
	 
	 	 	 	 	 	 
	 
	 	 	 	Rolling Meadows, IL 60008	 	 
	 
	 	 	 	 	 	 
	 
	 	 	 	      
	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 	 	VOLVO CONSTRUCTION	 	 
	 	 	EQUIPMENT NORTH AMERICA, INC.	 	 
	 
	 	 	 	 	 	 
	 
	 	By:	/s/ Martha P. Boyd	 	 
	 
	 	 	 	 	 
	 
	 	 	 	 	 	 
	 

	 	Name:
	 	Martha P. Boyd	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	(Print)	 	 
	 
	 	 	 	 	 	 
	 
	 	Address:	 	One Volvo Drive	 	 
	 
	 	 	 	 	 	 
	 
	 	 	 	Asheville, NC 28803	 	 
	 
	 	 	 	 	 	 
	 

	 	 	 	 	 	 

SIGNATURE PAGE TO IRONPLANET.COM, INC. THIRD AMENDED AND

RESTATED INVESTORS’ RIGHTS AGREEMENT

 

 

     The parties have executed this Third Amended and Restated Investors’ Rights Agreement as of
the date first above written.

	 	 	 	 	 	 	 
	 	 	RING POWER CORPORATION	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Randal L. Ringhaver
 

	 	 
	 	 	Name: Randal L. Ringhaver	 	 
	 	 	Title: President	 	 
	 
	 	 	 	 	 	 
	 

	 	Address:	 	500 World Commerce Pancway 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	St. Augustine, FL 32092 	 	 
	 	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 

	 	Phone:	 	(904) 201 – 7464 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 

	 	Fax:	 	(904) 281 – 0155 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	 

	 	E-mail:	 	 	 	 
	 

	 	 	 	 	 	 

SIGNATURE PAGE TO IRONPLANET.COM, INC. THIRD AMENDED AND

RESTATED INVESTORS’ RIGHTS AGREEMENT

 

 

EXHIBIT A

Series A Holders

Name and Address

Accel VII L.P.

Accel Internet Fund III L.P.

Accel Investors ’99 L.P.

          c/o Arthur C. Patterson

          428 University Ave.

          Palo Alto, CA 94301

Auchincloss Wadsworth & Co., L.P.

          11 Newbury Street, Suite 500

          Boston, MA 02116

Arthur C. Patterson

          c/o Accel Partners

          428 University Avenue

          Palo Alto, CA 94301

Copy To: G. Carter Sednaoui

          Accel Partners

          One Palmer Square

          Princeton, NJ 08542

KPCB Holdings, Inc.

          2750 Sand Hill Road

          Menlo Park, CA 94025

Dyncorp Technical Services, Inc.

          One Ridgemar Centre

          6500 West Freeway

          Fort Worth, TX 76116

Michael C. Jackson

          c/o Housatonic Partners

          11 Newbury Street, Suite 500

          Boston, MA 02116

Brandon L. Nixon

          c/o Housatonic Partners

          11 Newbury Street, Suite 500

          Boston, MA 02116

 

 

Name and Address

Barry Reynolds

          c/o Housatonic Partners

          11 Newbury Street, Suite 500

          Boston, MA 02116

William Thorndike

          c/o Housatonic Partners

          11 Newbury Street, Suite 500

          Boston, MA 02116

VLG Investments 1999

          2800 Sand Hill Road

          Menlo Park, CA 94025

John V. Bautista

          c/o Venture Law Group

          2775 Sand Hill Road

          Menlo Park, CA 94025

Edmund Ruffin

          c/o Venture Law Group

          2800 Sand Hill Road

          Menlo Park, CA 94025

Richard Hsu

          c/o Venture Law Group

          2775 Sand Hill Road

          Menlo Park, CA 94025

MRS Investors

          c/o Mark Winfield-Hansen

          Venture Law Group

          2800 Sand Hill Road

          Menlo Park, CA 94025

 

 

EXHIBIT A

Series B Holders

Name and Address

Caterpillar, Inc.

          100 N.E. Adams Street

          Peoria, IL 61629

Komatsu America Corp.

          440 North Fairway Drive

          P.O. Box 8112

          Vernon Hills, IL 60061-8112

Volvo Construction Equipment N. V.

          Chausee de la Hulpe 130

          Brussels, BE-1000, Belgium

KPCB Holdings, Inc.

          2750 Sand Hill Road

          Menlo Park, CA 94025

Accel VII L.P.

Accel Internet Fund III L.P.

Accel Investors ’99 L.P.

ACP Family Partnership L.P.

          c/o Arthur C. Patterson

          428 University Avenue

          Palo Alto, CA 94301

          Copy to:

          G. Carter Sednaoui, CFO

          One Palmer Square

          Princeton, NJ 08542

Marubeni Construction Machinery (America) Inc.

          200 E. Randolph Dr., Suite 4838

          Chicago, IL 60601

MAC Investment Co., Inc.

          450 Lexington Avenue

          New York, NY 10017

Marubeni America Corp., Information

Technology & Infrastructure Project

Group

          101 California Street, Suite 1150

          San Francisco, CA 94111

 

 

Name and Address

Marubeni America Corp., Machinery Group

          450 Lexington Avenue

          New York, NY 10017

Comdisco, Inc.

          Attn: Venture Group

          6111 North River Road

          Rosemont, IL 60018

Copy To: 100 Hamilton, Suite 104A

                Palo Alto, CA 94301

Ignite Ventures II, L.P.

          255 Shoreline Drive, Suite 510

          Redwood City, CA 94065

Ignite Entrepreneurs, L.P.

          255 Shoreline Drive, Suite 510

          Redwood City, CA 94065

Altec Ventures LLC

210 Inverness Center Drive

Birmingham, AL 35242

Robert B. Alleger, Jr.

Robert B. Alleger, Sr.

Patrick C. Fitzpatrick

Jay Gorman

Jay Ward

Kenneth D. Cramer

Charles Nardo

European Founders Fund GmbH

Attn: Marc Samwer

Lindenalle 45

50968 Koln

Germany

-26-

 

EXHIBIT A

Series C Holders

Name and Address

Ring Power Corporation

          500 World Commerce Parkway

          St. Augustine, FL 32092

-27-exv4w3

Exhibit 4.3

IRONPLANET.COM, INC.

AMENDMENT TO THIRD AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT

     This Amendment (the “Amendment”) to the Third Amended and Restated Investors’ Rights
Agreement dated August 28, 2008 (the “Rights Agreement”) is made and entered into as of
August 29, 2008 by and among IronPlanet.com, Inc., a Delaware corporation (the “Company”)
and Australian Capital Equity (USA), Inc. (“ACE USA”). All terms not defined herein shall
have the meaning given to them in the Rights Agreement.

RECITALS

     A. The Company, the Founder, and certain holders of the Company’s Preferred Stock (the
“Existing Preferred Holders”) have previously entered into the Rights Agreement, pursuant
to which the Company granted the Founder and the Existing Preferred Holders certain rights.

     B. The Company and ACE USA are parties to that certain Series C Preferred Stock Purchase
Agreement (“Purchase Agreement”) dated as of an even date herewith, whereby the Company
wishes to sell, and ACE USA wishes to purchase shares of the Company’s Series C Preferred Stock.

     C. A condition to ACE USA’s obligations under the Purchase Agreement is that the Company amend
the Rights Agreement in order to provide ACE USA with (i) certain rights to register shares of the
Company’s Common Stock issuable upon conversion of the Series C Preferred Stock held by ACE USA,
(ii) certain rights to receive or inspect information pertaining to the Company, and (iii) a right
of first offer with respect to certain issuances by the Company of its securities.

     D. The Company desires to amend the Rights Agreement to add ACE USA as a party thereto.

     F. Pursuant to Section 3.3 of the Rights Agreement, the Rights Agreement may be amended with
only the written consent of the Company for the sole purpose of including additional purchasers of
Series C Preferred Stock as “Investors” and “Holders.”

AGREEMENT

     The parties hereby agree as follows:

     1. Execution of Rights Agreement. The Company acknowledges and agrees that upon
execution of this Amendment, ACE USA shall become a party to the Rights Agreement and an “Investor”
and “Holder” as defined therein and shall be entitled to all rights and subject to all obligations
as a party thereto.

 

 

     2. Force and Effect. Except as amended and set forth above, the Rights Agreement
shall remain in full force and effect.

     3. Miscellaneous.

          3.1 Governing Law. This Amendment and all acts and transactions pursuant hereto shall
be governed, construed and interpreted in accordance with the laws of the State of California,
without giving effect to principles of conflicts of laws.

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

[Signature Pages Follow]

 

 

     The parties have executed this Amendment as of the date first written above.

	 	 	 	 	 	 	 
	 	 	COMPANY:	 	 
	 
	 	 	 	 	 	 
	 	 	IRONPLANET.COM, INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:

Name:
	 	/s/ Gregory J. Owens
 

Gregory J. Owens
	 	 
	 

	 	Title:
	 	President and Chief Executive Officer	 	 
	 
	 	 	 	 	 	 
	 	 	Address:	 	 
	 	 	4695 Chabot Drive, #102	 	 
	 	 	Pleasanton CA 94588	 	 
	 	 	Fax: (925) 225-8810	 	 
	 
	 	 	 	 	 	 
	 	 	AUSTRALIAN CAPITAL EQUITY (USA), INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ Jerry B. Daniel	 	 
	 

	 	 	 	 	 	 
	 

	 	Name:
	 	Jerry B. Daniel	 	 
	 

	 	Title:
	 	President	 	 

SIGNATURE PAGE TO AMENDMENT TO THIRD AMENDED AND RESTATED INVESTORS’

RIGHTS AGREEMENT OF IRONPLANET.COM, INC.

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