Document:

exv10w52

Exhibit 10.52

SIXTH AMENDMENT TO INVESTOR RIGHTS AGREEMENT

     THIS SIXTH AMENDMENT TO INVESTOR RIGHTS AGREEMENT (this “Sixth Amendment”) is
entered into as of August __, 2011 (the “Sixth Amendment Date”), by and among TrustWave
Holdings, Inc., a Delaware corporation (the “Company”), and the persons signatory hereto
(the “Signatories”).

RECITALS

     WHEREAS, the Company and its stockholders are parties to that certain Investor Rights
Agreement, dated as of March 14, 2005, as amended through the date hereof (as so amended, the
“Original Agreement”); and

     WHEREAS, all capitalized terms used in this Sixth Amendment which are not defined herein shall
have the respective meanings assigned to them in the Original Agreement; and

     WHEREAS, the Signatories constitute the holders of at least a majority of the Registrable
Securities; and

     WHEREAS, the parties hereto desire to amend the Original Agreement as provided in this Sixth
Amendment.

     NOW, THEREFORE, in consideration of the foregoing recitals and the mutual promises,
representations, warranties, covenants and conditions contained in this Sixth Amendment and for
other good and valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the parties hereto, intending to be legally bound, agree as follows:

     1. Addition of Common Stockholders. For all purposes of the Original Agreement, as
amended by this Sixth Amendment, each stockholder listed on the attached Schedule 1 is
hereby constituted as a Common Stockholder and, so long as on the date of determination such
stockholder holds Registrable Securities representing at least 100,000 shares of Common Stock, a
Major Common Stockholder.

     2. Information and Reporting. Without limiting the foregoing, each stockholder listed
on the attached Schedule 1 shall be entitled to the benefits of Sections 3.1 and 3.2 of the
Original Agreement, subject to the limitations contained in Sections 3.3 and 3.7 of the Original
Agreement, so long as such stockholder is a Major Investor and continues to hold at least ten
percent (10%) of the total number of shares of capital stock (as adjusted for stock splits and on
an as-converted basis) held by such stockholder on the Sixth Amendment Date.

     3. Joinder. By executing this Sixth Amendment, each stockholder listed on the
attached Schedule 1 agrees that it shall succeed to all of the obligations of a Common
Stockholder, Major Common Stockholder and/or Major Investor as contemplated by the Original
Agreement, as amended by this Sixth Amendment.

     4. No Other Amendments. Except as expressly amended by this Sixth Amendment, all of
the terms and provisions of the Original Agreement shall remain in full force and effect.

 

 

     5. Counterparts. This Sixth Amendment may be executed by facsimile and in
counterparts, each of which shall be an original, but all of which together shall constitute one
instrument.

(SIGNATURES ON NEXT PAGES)

 

 

     IN WITNESS WHEREOF, the parties hereto have caused this Sixth Amendment to be executed as of
the Sixth Amendment Date.

	 	 	 	 	 	 	 

	 	 	COMPANY:	 	 
	 
	 	 	 	 	 	 
	 	 	TRUSTWAVE HOLDINGS, INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name: Robert McCullen
	 	 
	 

	 	 	 	Title: Chief Executive Officer	 	 

	 	 	 	 	 	 	 

	 	 	STOCKHOLDERS:	 	 
	 
	 	 	 	 	 	 
	 	 	Financial Technology Ventures II (Q), L.P.	 	 
	 	 	Financial Technology Ventures II, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	Financial Technology Management, II, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	Richard Kiphart	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	David Valentine	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	DBRC Investments, LLC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	Phillip J. Smith	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	MBK Ventures, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name: Robert McCullen
	 	 
	 

	 	 	 	Title: Manager	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	Caledonia Investments, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name: Tim Nicholson
	 	 
	 

	 	 	 	Title: Managing Director	 	 
	 
	 	 	 	 	 	 
	 	 	Nicholson Acquisitions LP	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name: Tim Nicholson
	 	 
	 

	 	 	 	Title: General Partner	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	THE PRODUCTIVITY FUND IV, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	First Analysis Management Company IV,	 	 
	 

	 	 	 	L.L.C., its General Partner	 	 
	 

	 	By:
	 	First Analysis Venture Operations and	 	 
	 

	 	 	 	Research, L.L.C., its Member	 	 
	 

	 	By:
	 	First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 
	 
	 	 	 	 	 	 
	 	 	THE PRODUCTIVITY FUND IV ADVISORS
FUND, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	First Analysis Management Company IV,	 	 
	 

	 	 	 	L.L.C., its General Partner	 	 
	 

	 	By:
	 	First Analysis Venture Operations and	 	 
	 

	 	 	 	Research, L.L.C., its Member	 	 
	 

	 	By:
	 	First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 
	 
	 	 	 	 	 	 
	 	 	FA PRIVATE EQUITY FUND IV, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	FA Private Equity Management IV, L.C.C.,	 	 
	 

	 	 	 	its General Partner	 	 
	 

	 	By:
	 	First Analysis Private Equity Management	 	 
	 

	 	 	 	Company IV, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Venture Operations and	 	 
	 

	 	 	 	Research, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	FA PRIVATE EQUITY FUND IV GMBH & CO. BETEILIGUNGS KG	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	FA Private Equity Management IV, L.C.C.,	 	 
	 

	 	 	 	its Managing Limited Partner	 	 
	 

	 	By:
	 	First Analysis Private Equity Management 	 	 
	 

	 	 	 	Company IV, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Venture Operations and	 	 
	 

	 	 	 	Research, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	SRBA #5, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	Hallman Management Trust, its General Partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Trustee
	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	Bullseye Securities, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	Venture Lending & Leasing IV, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 

	 

	 	 

William Bertrand, Jr.
	 	 
	 
	 	 	 	 
	 

	 	 

Stuart Harvey
	 	 
	 
	 	 	 	 
	 

	 	 

Walter Hosp
	 	 
	 
	 	 	 	 
	 

	 	 

L. Neil Hunn
	 	 
	 
	 	 	 	 
	 

	 	 

Zachary Nelson
	 	 
	 
	 	 	 	 
	 

	 	 

Ruth Ann Marshall
	 	 
	 
	 	 	 	 
	 

	 	 

Kevin Bradford
	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	FTVentures III, L.P.	 	 
	 	 	FTVentures III-N, L.P.	 	 
	 	 	FTVentures III-T, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	FTVentures Management III, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 

Signature Page to Sixth Amendment to Investor Rights Agreement

 

 

SCHEDULE 1

Bullseye Securities, LLC

Venture Lending & Leasing IV, LLC

William Bertrand, Jr.

Stuart Harvey

Walter Hosp

L. Neil Hunn

Zachary Nelson

Ruth Ann Marshall

Kevin Bradford

FTVentures III, L.P.

FTVentures III-N, L.P.

FTVentures III-T, L.P.exv10w53

Exhibit 10.53

SEVENTH AMENDMENT TO INVESTOR RIGHTS AGREEMENT

     THIS SEVENTH AMENDMENT TO INVESTOR RIGHTS AGREEMENT (this “Seventh
Amendment”) is entered into as of 

August __, 2011 (the “Seventh Amendment Date”), by
and among TrustWave Holdings, Inc., a Delaware corporation (the “Company”), and the persons
signatory hereto (the “Signatories”).

RECITALS

     WHEREAS, the Company and its stockholders are parties to that certain Investor Rights
Agreement, dated as of March 14, 2005, as amended through the date hereof (as so amended, the
“Original Agreement”); and

     WHEREAS, all capitalized terms used in this Seventh Amendment which are not defined herein
shall have the respective meanings assigned to them in the Original Agreement; and

     WHEREAS, the Signatories constitute the holders of at least a majority of the Registrable
Securities; and

     WHEREAS, the parties hereto desire to amend the Original Agreement as provided in this Seventh
Amendment.

     NOW, THEREFORE, in consideration of the foregoing recitals and the mutual promises,
representations, warranties, covenants and conditions contained in this Seventh Amendment and for
other good and valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the parties hereto, intending to be legally bound, agree as follows:

     1. Certain Definitions. The following definition contained in Section 1.1 of
the Original Agreement is hereby amended to read, in its entirety, as follows:

“Qualified Public Offering” means either (i) a Qualified Public Offering, as such
term is defined in the Company’s Certificate of Incorporation, or (ii) the initial public
offering of the Company’s common stock pursuant to the Company’s Registration Statement on
Form S-1 (SEC No. 333-173661), regardless of the initial public offering price.

     2. No Other Amendments. Except as expressly amended by this Seventh Amendment, all of
the terms and provisions of the Original Agreement shall remain in full force and effect.

     3. Counterparts. This Seventh Amendment may be executed by facsimile and in
counterparts, each of which shall be an original, but all of which together shall constitute one
instrument.

(SIGNATURES ON NEXT PAGES)

 

 

     IN WITNESS WHEREOF, the parties hereto have caused this Seventh Amendment to be executed as of
the Seventh Amendment Date.

	 	 	 	 	 	 	 

	 	 	COMPANY:	 	 
	 
	 	 	 	 	 	 
	 	 	TRUSTWAVE HOLDINGS, INC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Name: Robert McCullen

Title: Chief Executive Officer	 	 
	 
	 	 	 	 	 	 
	 	 	STOCKHOLDERS:	 	 
	 
	 	 	 	 	 	 
	 	 	Financial Technology Ventures II (Q), L.P.	 	 
	 	 	Financial Technology Ventures II, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	Financial Technology Management, II, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 
	 
	 	 	 	 	 	 
	 	 	FTVentures III, L.P.	 	 
	 	 	FTVentures III-N, L.P.	 	 
	 	 	FTVentures III-T, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	FTVentures Management III, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	Richard Kiphart	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	David Valentine	 	 

Signature Page to Seventh Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	DBRC Investments, LLC.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name:
	 	 
	 

	 	 	 	Title:	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	Phillip J. Smith	 	 
	 
	 	 	 	 	 	 
	 	 	 	 	 
	 	 	Kevin Bradford	 	 
	 
	 	 	 	 	 	 
	 	 	MBK Ventures, LLC	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name: Robert McCullen
	 	 
	 

	 	 	 	Title: Manager	 	 

Signature Page to Seventh Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	Caledonia Investments, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name: Tim Nicholson
	 	 
	 

	 	 	 	Title: Managing Director	 	 
	 
	 	 	 	 	 	 
	 	 	Nicholson Acquisitions LP	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Name: Tim Nicholson
	 	 
	 

	 	 	 	Title: General Partner	 	 

Signature Page to Seventh Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	THE PRODUCTIVITY FUND IV, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	First Analysis Management Company IV,	 	 
	 

	 	 	 	L.L.C., its General Partner	 	 
	 

	 	By:
	 	First Analysis Venture Operations and	 	 
	 

	 	 	 	Research, L.L.C., its Member	 	 
	 

	 	By:
	 	First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 
	 
	 	 	 	 	 	 
	 	 	THE PRODUCTIVITY FUND IV ADVISORS FUND, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:

By:

By:
	 	First Analysis Management Company 

IV,
 L.L.C., its General Partner

First Analysis Venture Operations and

Research, L.L.C., its Member

First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 
	 
	 	 	 	 	 	 
	 	 	FA PRIVATE EQUITY FUND IV, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	FA Private Equity Management IV, L.C.C.,	 	 
	 

	 	 	 	its General Partner	 	 
	 

	 	By:
	 	First Analysis Private Equity Management 	 	 
	 

	 	 	 	Company IV, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Venture Operations and	 	 
	 

	 	 	 	Research, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 

Signature Page to Seventh Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	FA PRIVATE EQUITY FUND IV GMBH & CO. BETEILIGUNGS KG	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	FA Private Equity Management IV, L.C.C.,	 	 
	 

	 	 	 	its Managing Limited Partner	 	 
	 

	 	By:
	 	First Analysis Private Equity Management 	 	 
	 

	 	 	 	Company IV, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Venture Operations and	 	 
	 

	 	 	 	Research, L.L.C., its Managing Member	 	 
	 

	 	By:
	 	First Analysis Corporation, its Manager	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Howard S. Smith, Managing Director
	 	 

Signature Page to Seventh Amendment to Investor Rights Agreement

 

 

	 	 	 	 	 	 	 

	 	 	SRBA #5, L.P.	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	Hallman Management Trust, its General Partner	 	 
	 
	 	 	 	 	 	 
	 

	 	By:	 	 	 	 
	 

	 	 	 	 

Trustee
	 	 

Signature Page to Seventh Amendment to Investor Rights Agreement

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