Document:

exv10w21

Exhibit 10.21

SECOND AMENDMENT TO STOCKHOLDERS’ AGREEMENT

     THIS SECOND AMENDMENT TO STOCKHOLDERS’ AGREEMENT (this “Amendment”) is
entered into as of June 3, 2008 (the “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 Stockholders’ 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 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 issued and
outstanding shares of Common Stock (on an as-converted basis); and

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

     NOW, THEREFORE, in consideration of the foregoing recitals and the mutual promises,
representations, warranties, covenants and conditions contained in this 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. Exhibit C. Exhibit C attached to the Original Agreement is hereby amended to read,
in its entirety, as set forth on Exhibit C attached to this Amendment.

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

     3. Counterparts. This 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.

[Signature Page Follows]

 

 

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

	 	 	 	 	 
	 	COMPANY:

TRUSTWAVE HOLDINGS, INC.

 	 
	 	By:  	/s/ Robert McCullen
 	 
	 	 	Name:  	Robert McCullen 	 
	 	 	Title:  	Chief Executive Officer 	 

	 	 	 	 	 
	 	STOCKHOLDERS:

Financial Technology Ventures II (Q), L.P.
 	 
	 	By:  	     Financial Technology Management, II, LLC
 	 

	 	 	 	 	 
	 	 	 
	 	By:  	                         /s/ Richard Garman
 	 
	 	 	Name:  	Richard Garman 	 
	 	 	Title:  	 	 

	 	 	 	 	 
	 	Financial Technology Ventures II, L.P.
 	 
	 	By:  	Financial Technology Management, II, LLC
 	 

	 	 	 	 	 
	 	 	 
	 	By:  	                          /s/ Richard Garman
 	 
	 	 	Name:  	 	 
	 	 	Title:  	 	 

	 	 	 	 	 
	 	 	 
	 	     /s/ Richard Kiphart
 	 
	 	Richard Kiphart 	 

	 	 	 	 	 
	 	 	 
	 	   /s/ David Valentine
 	 
	 	David Valentine 	 

2

 

	 	 	 	 	 
	 	DBRC Investments, LLC.

 	 
	 	By:  	/s/
 	 
	 	 	Name:  	 	 
	 	 	Title:  	 	 

	 	 	 	 	 
	 	     /s/ Joseph Patanella
 	 
	 	Joseph L. Patanella 	 

	 	 	 	 	 
	 	      /s/ Phillip J. Smith
 	 
	 	Phillip J. Smith 	 

	 	 	 	 	 
	 	Caledonia Investments, L.P.

 	 
	 	By:  	/s/ Tim Nicholson
 	 
	 	 	Name:  	Tim Nicholson 	 
	 	 	Title:  	 	 

	 	 	 	 	 
	 	The Nicholson Family Limited Partnership

 	 
	 	By:  	/s/ Tim Nicholson
 	 
	 	 	Name:  	Tim Nicholson 	 
	 	 	Title:  	 	 

	 	 	 	 	 
	 	MBK Ventures, LLC

 	 
	 	By:  	/s/ Robert McCullen
 	 
	 	 	Name:  	Robert McCullen 	 
	 	 	Title:  	Manager 	 

	 	 	 	 	 
	  	 	 
	 	Erik Schetina 	 
	 	 	 	 

3

 

	 	 	 	 	 	 	 

	 	 	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:  	          /s/ Howard S. Smith
 	 
	 	 	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:  	         /s/ Howard S. Smith
 	 
	 	 	Howard S. Smith, Managing Director 	 
	 	 	 	 

4

 

	 	 	 	 	 

EXHIBIT C

List of Investors

Name and Address

Series A-1 Preferred

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

c/o Financial Technology Management II, LLC

601 California Street, Suite 2200

San Francisco, California 94108

Attention: David Haynes

Facsimile: 415.229.3005

Financial Technology Ventures II, L.P.

c/o Financial Technology Management II, LLC

601 California Street, Suite 2200

San Francisco, California 94108

Attention: David Haynes

Facsimile: 415.229.3005

Series A-2 Preferred

Julia Gluck

530 Longwood

Glencoe, IL 60022

Rebecca Kiphart

c/o William Blair and Company

222 W. Adams

Chicago, IL 60606

Richard Kiphart

c/o William Blair and Company

222 W. Adams

Chicago, IL 60606

David Valentine

348 Sterling Road

Kenilworth, IL 60043

Series B Preferred

DBRC Investments, LLC.

70 West Madison, Suite 5500

Chicago, Il 60602

 

 

Class A Common

Barry Patrick Smith

11816 Hunting Ridge Court

Potomac, Maryland 20854

Frank R. Sourbeer

100 Cumberland Road

Lemoyne, PA 17403

Caledonian Investments, L.P.

c/o Timothy F. Nicholson

304 Gilbert Road

Dillsburg, PA 17019

The Nicholson Family Limited Partnership

c/o Timothy F. Nicholson

304 Gilbert Road

Dillsburg, PA 17019

Joseph L. Patanella

3405 Hidden River View Rd

Annapolis, Maryland 21403

Erik S. Schetina

82-40 Austin Sr

Kew Gardens NY 11415

Ronald Waranowski

2914 Constellation Way

Finksburg, MD 21048

Phillip J. Smith

12127 Long Ridge Lane

Bowie, Maryland 20715

Jacob Carlson

444 16th St

Brooklyn, NY 11215

Daniel Muldoon

5228 Waugh Point Rd

King George, VA 22485

Jaime Romero

442 W 22nd St #14

New York, NY 10011

 

 

The Patanella Family Trust

c/o James S. Patanella

920 Sunset Valley Drive

Sykesville, MD 21784

Jack Troia

2987 Fort Matanaza Terrace

Henderson, NV 89052

MBK Ventures, LLC

566 West Adams, Suite 401

Chicago, Illinois 60661

Attn: Andrew Bokor and Robert McCullen, Managers

Productivity Fund IV, LP

Productivity Fund IV Advisors Fund, LP

FA Private Equity Fund IV, LP

FA Private Equity Fund IV GMBH

1 South Wacker Suite 3900

Chicago, IL 60606

Prism Opportunity Fund SBIC, LP

444 N. Michigan Ave

Chicago, IL 60611

Argentum Capital Partners II, LP

60 Madison Ave

New York, NY 10010

VM Funding, LLC

310 Redgate Farm

Troy VA 22974exv10w22

Exhibit 10.22

THIRD AMENDMENT TO STOCKHOLDERS’ AGREEMENT

     THIS THIRD AMENDMENT TO STOCKHOLDERS’ AGREEMENT (this “Amendment”) is entered
into as of August 26, 2009 (the “Third 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 Stockholders’ 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 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 issued and
outstanding shares of Common Stock (on an as-converted basis); and

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

     NOW, THEREFORE, in consideration of the foregoing recitals and the mutual promises,
representations, warranties, covenants and conditions contained in this 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 Stockholders. The stockholders listed on the attached Schedule
1 are hereby constituted as Other Stockholders and Stockholders for all purposes of the
Original Agreement, as amended by this Amendment.

     2. Exhibit C. Exhibit C attached to the Original Agreement is hereby amended by
adding thereto the stockholders listed on the attached Schedule 1.

     3. Eligible Stockholders. The stockholders listed on the attached Schedule 1
are hereby constituted as Eligible Stockholders so long as they hold at least 100,000 Shares (as
adjusted for stock splits and on an as-converted basis) as of the Third Amendment Date and as of
the date of the Offer.

     4. Permitted Transfer. The second sentence of Section 3.5 of the Original Agreement
is amended to read, in its entirety, as follows:

For purposes of this Agreement, “Permitted Transfer” means any
Transfer by a Stockholder of any shares of capital stock (a) between any two
Stockholders listed on Exhibit C, (b) to or for the benefit of any
immediate

 

 

family member of the Stockholder, to a trust for the benefit of the
Stockholder or any immediate family member, or to a family partnership, (c)
any Affiliate of a Stockholder (including a distribution to a partner or a
liquidation to the benefit of the partners of the Stockholder), or (d) any
transferee approved by a majority of the Board (collectively, “Permitted
Transferees”); provided, that (i) the limitations contained in
Section 3.4 shall still apply to any Permitted Transfer and shall
apply to a Permitted Transferee upon subsequent transfer, and (ii) clause
(d) shall not be available for transfers of more than 10% of the Common
Stock (after giving effect to the conversion, exchange or exercise as the
case may be of all securities convertible into, or exercisable or
exchangeable for, Common Stock, including all unexpired and unexercised
options, warrants or other rights to acquire Common Stock) in any
transaction or series of related transactions.

     5. Joinder. By executing this Amendment, each stockholder listed on the attached
Schedule 1 agrees that he, she or it shall succeed to all of the obligations of an Other
Stockholder, Stockholder and/or Eligible Stockholder as contemplated by the Original Agreement, as
amended by this Amendment.

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

     7. Counterparts. This 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.

[Signature Page Follows]

2

 

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

	 	 	 	 	 
	 	COMPANY:

TRUSTWAVE HOLDINGS, INC.

 	 
	 	By:  	              /s/ Robert McCullen
 	 
	 	 	Name:  	Robert McCullen 	 
	 	 	Title:  	Chief Executive Officer 	 
	 
	 	STOCKHOLDERS:

Financial Technology Ventures II (Q), L.P.
By: Financial Technology Management, II, LLC

 	 
	 	By:  	/s/ Richard N. Garman
 	 
	 	 	Name:  	Richard N. Garman 	 
	 	 	Title:  	Managing Member 	 
	 
	 	Financial Technology Ventures II, L.P.
By: Financial Technology Management, II, LLC

 	 
	 	By:  	/s/ Richard Garman
 	 
	 	 	Name:  	Richard N. Garman 	 
	 	 	Title:  	Managing Member 	 
	 
	 	                               /s/ Richard Kiphart
 	 
	 	Richard Kiphart 	 
	 	 	 
	 	     /s/ David Valentine
 	 
	 	David Valentine 	 
	 

3

 

	 	 	 	 	 
	 	DBRC Investments, LLC.

 	 
	 	By:  	/s/ Robert McCullen
 	 
	 	 	Name:  	 	 
	 	 	Title:  	 	 
	 
	 	                          /s/ Joseph K. Patanella
 	 
	 	Joseph L. Patanella 	 
	 	 	 
	 	                          /s/ Phillip J. Smith
 	 
	 	Phillip J. Smith 	 
	 	 	 
	 	Caledonia Investments, L.P.

 	 
	 	By:  	/s/ Tim Nicholson
 	 
	 	 	Name:  	Tim Nicholson 	 
	 	 	Title:  	Managing Director 	 
	 
	 	The Nicholson Family Limited Partnership

 	 
	 	By:  	/s/ Tim Nicholson
 	 
	 	 	Name:  	Tim Nicholson 	 
	 	 	Title:  	General Partner 	 
	 
	 	MBK Ventures, LLC

 	 
	 	By:  	/s/ Robert McCullen
 	 
	 	 	Name:  	Robert McCullen 	 
	 	 	Title:  	Manager 	 
	 

4

 

	 	 	 	 	 	 	 

	 	 	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:
	 	/s/ Howard Smith	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	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:
	 	/s/ Howard Smith	 	 
	 

	 	 	 	 	 	 
	 

	 	 	 	Howard S. Smith, Managing Director	 	 

5

 

	 	 	 	 	 	 	 

	SIGMA PARTNERS 6, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ Robert Davoli	 	 
	 	 	 	 	 
	 	 	Its Managing Director	 	 
	 
	 	 	 	 	 	 
	SIGMA ASSOCIATES 6, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ Robert Davoli	 	 
	 	 	 	 	 
	 	 	Its Managing Director	 	 
	 
	 	 	 	 	 	 
	SIGMA INVESTORS 6, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ Robert Davoli	 	 
	 	 	 	 	 
	 	 	Its Managing Director	 	 
	 
	 	 	 	 	 	 
	WILLIAM BLAIR CAPITAL PARTNERS VII QP, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	Ellen Carnahan	 	 
	 	 	 	 	 
	 	 	Its Managing Director of its GP	 	 
	 
	 	 	 	 	 	 
	WILLIAM BLAIR CAPITAL PARTNERS VII, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	Ellen Carnahan	 	 
	 	 	 	 	 
	 	 	Its Managing Director of its GP	 	 
	 
	 	 	 	 	 	 
	GCP IV AFFILIATES, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ [illegible signature]	 	 
	 	 	 	 	 
	 

	 	Its	 	 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	GLOBESPAN CAPITAL PARTNERS IV GMBH & CO. KG	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ [illegible signature]	 	 
	 	 	Its
	 	 
	 	 	 	 
	 	 

6

 

	 	 	 	 	 	 	 

	JAFCO GLOBESPAN USIT IV, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ [illegible signature]	 	 
	 	 	 	 	 
	 

	 	Its	 	 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	GLOBESPAN CAPITAL PARTNERS (CAYMAN) IV, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ [illegible signature]	 	 
	 	 	 	 	 
	 

	 	Its	 	 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	GLOBESPAN CAPITAL PARTNERS IV, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ [illegible signature]	 	 
	 	 	 	 	 
	 

	 	Its	 	 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	SEQUEL LIMITED PARTNERSHIP III	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ [illegible signature]	 	 
	 	 	 	 	 
	 

	 	Its	 	 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	SEQUEL ENTREPRENEURS’ FUND III, L.P.	 	 
	 
	 	 	 	 	 	 
	By:	 	/s/ [illegible signature]	 	 
	 	 	 	 	 
	 

	 	Its	 	 	 	 
	 

	 	 	 	 	 	 
	 
	 	 	 	 	 	 
	/s/ David Parkinson	 	 
	 	 	 
	David Parkinson	 	 
	 
	 	 	 	 	 	 
	/s/ James M. Barker	 	 
	 	 	 
	James M. Barker	 	 

7

 

SCHEDULE 1

Viking Stockholders

Sigma Partners 6, L.P.

Sigma Associates 6, L.P.

Sigma Investors 6, L.P.

William Blair Capital Partners VII QP, L.P.

William Blair Capital Partners VII, L.P.

GCP IV Affiliates, L.P.

Globespan Capital Partners IV GmbH & Co. KG

JAFCO Globespan USIT IV, L.P.

Globespan Capital Partners (Cayman) IV, L.P.

Globespan Capital Partners IV, L.P.

Sequel Limited Partnership III

Sequel Entrepreneurs’ Fund III, L.P.

David Parkinson

James M. Barker

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