Convertible Secured Promissory Note between Renaissance Trading Technologies, LLC and NYFIX, Inc.

 Exhibit 10.14 RENAISSANCE TRADING TECHNOLOGIES, LLC CONVERTIBLE SECURED PROMISSORY NOTE NEITHER THIS NOTE NOR THE LIMITED LIABILITY COMPANY UNITS ISSUABLE UPON CONVERSION HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED ("ACT"), OR UNDER ANY STATE SECURITIES LAW AND SUCH SECURITIES MAY NOT BE PLEDGED, SOLD, ASSIGNED OR TRANSFERRED IN THE ABSENCE OF AN EFFECTIVE REGISTRATION STATEMENT WITH RESPECT THERETO UNDER THE ACT AND ANY APPLICABLE STATE SECURITIES LAW, OR UNLESS THE COMPANY RECEIVES AN OPINION OF COUNSEL, SATISFACTORY TO THE COMPANY, THAT SUCH REGISTRATION IS NOT REQUIRED. $1,500,000 As of October 2, 2002 FOR VALUE RECEIVED, RENAISSANCE TRADING TECHNOLOGIES, LLC, a Delaware limited liability company (the "Company"), promises to pay to the order of NYFIX, INC., a New York corporation (the "Holder"), on the earlier to occur of (i) the five year anniversary of the date hereof (the "Maturity Date"), or (ii) an Event of Default (as defined in Section 1 below), unless this Note is converted prior to such dates pursuant to Section 3 below, the principal amount of ONE MILLION FIVE HUNDRED THOUSAND DOLLARS ($1,500,000), in such coin or currency of the United States of America as at the time of payment shall be legal tender for the payment of public or private debts, together with interest on the unpaid balance of said principal amount from time to time outstanding at the rate of five and one-half percent (5 1/2%) per annum. If any payment hereunder becomes due and payable on a Saturday, Sunday or legal holiday under the laws of the United States of America or the State of New York, or both, the due date thereof shall be extended to the next business day. Payments of principal and interest are to be made at the address provided herein for the Holder (or at such other place as the Holder shall have notified the Company in writing at least five (5) days before such payment is due) or by wire transfer pursuant to the Holder's written instructions. 1. EVENTS OF DEFAULT. (a) Upon the occurrence of any of the following events (herein called "Events of Default"): (i) The Company shall fail to pay the principal of or interest on this Note on the Maturity Date; (ii) (A) The Company shall commence any proceeding or other action relating to it in bankruptcy or seek reorganization, arrangement, readjustment of its debts, receivership, dissolution, liquidation,  winding-up, composition or any other relief under any bankruptcy law, or under any other insolvency, reorganization, liquidation, dissolution, arrangement, composition, readjustment of debt or any other similar act or law, of any jurisdiction, domestic or foreign, now or hereafter existing; or (B) the Company shall admit the material allegations of any petition or pleading in connection with any such proceeding; or (C) the Company shall apply for, or consent or acquiesce to, the appointment of a receiver, conservator, trustee or similar officer for it or for all or a substantial part of its property; or (D) the Company shall make a general assignment for the benefit of creditors; (iii) (A) The commencement of any proceedings or the taking of any other action against the Company in bankruptcy or seeking reorganization, arrangement, readjustment of its debts, liquidation, dissolution, arrangement, composition, or any other relief under any bankruptcy law or any other similar act or law of any jurisdiction, domestic or foreign, now or hereafter existing; or (B) the appointment of a receiver, conservator, trustee or similar officer for the Company for any of its property; or (C) the issuance of a warrant of attachment, execution or similar process against any of the property of the Company; (iv) The Company shall fail to comply with any of its obligations under this Note, which failure shall continue uncured for five (5) business days after notice thereof to the Company; (v) The Company shall default with respect to any indebtedness for borrowed money (other than under this Note or otherwise related to payments due the Holder under any other agreement) with a principal amount in excess of $75,000 if either (a) the effect of such default is to accelerate the maturity of such indebtedness (giving effect to any applicable grace periods) or (b) the holder of such indebtedness declares the Company to be in default (giving effect to any applicable grace periods); or (vi) Any judgment or judgments against the Company or any attachment, levy or execution against any of its properties for any amount in excess of $75,000 in the aggregate shall remain unpaid, or shall not be released, discharged, dismissed, stayed or fully bonded for a period of thirty (30) days or more after its entry, issue or levy, as the case may be; then, and in any such event, the Holder, at the Holder's option and without written notice to the Company, may declare the entire principal amount of this Note then outstanding together with accrued unpaid interest thereon immediately due and payable, and the same shall forthwith become immediately due and payable without presentment, demand, protest, or other notice of any kind, all of which are expressly waived. The Events of Default listed herein are solely for the purpose of protecting the interests of the Holder of this Note. If the Note is not paid in full upon acceleration, as required above, interest shall accrue on the outstanding principal of and interest on this Note from the date of the 2  Event of Default up to and including the date of payment at a rate equal to the lesser of twelve percent (12.0%) per annum or the maximum interest rate permitted by applicable law. (b) NON-WAIVER AND OTHER REMEDIES. No course of dealing or delay on the part of the Holder of this Note in exercising any right hereunder shall operate as a waiver or otherwise prejudice the right of the Holder of this Note. No remedy conferred hereby shall be exclusive of any other remedy referred to herein or now or hereafter available at law, in equity, by statute or otherwise. (c) COLLECTION COSTS; ATTORNEY'S FEES. In the case of an Event of Default, if this Note is turned over to an attorney for collection, the Company agrees to pay all reasonable costs of collection, including reasonable attorney's fees and expenses and all out-of-pocket expenses incurred by the Holder in connection with such collection efforts, which amounts may, at the Holder's option, be added to the principal hereof. 2. CANCELLATION. Upon full satisfaction of the Company's obligations hereunder, the Holder shall promptly deliver or cause to be delivered to the Company this Note for cancellation. 3. CONVERSION. (a) Following the twelve month anniversary of the date of this Note, the Holder has the right, at the Holder's option, at any time prior to payment in full of the principal and accrued interest due under this Note, to convert the outstanding principal amount of this Note, into 6,400,000 fully paid and non-assessable units of membership interests of the Company (the "Units"), subject to adjustment for all splits, combinations, dividends, recapitalizations and the like on the Company's Units. Upon conversion, the Company shall pay to the Holder a cash amount equal to all accrued and unpaid interest on this Note as of such date. (b) Upon conversion of this Note under Section 3(a), the Holder shall surrender this Note to the Company. As promptly as practicable after the conversion of this Note, the Company at its expense will issue and deliver to the Holder a certificate or certificates for the number of full shares of Units issuable upon such conversion. Such conversion shall be deemed to have been made immediately prior to the close of business on the date of the surrender of this Note, and the person or persons entitled to receive the Units issuable upon such conversion shall be treated for all purposes as the record holder or holders of such Units as of such date. 3  4. PURCHASE OPTION. As additional consideration for making this loan to the Company, the Holder is hereby granted the option to purchase the number of Units equal to the amount of the Units repurchased by the Company from the Company's members pursuant to Section 14.3 of the Amended and Restated Limited Liability Operating Agreement of the Company of even date herewith, in exchange for a payment by the Holder to the Company equal to such Units' book value (defined as the Company's members equity as determined in accordance with accounting principles generally accepted in the United States of America divided by the number of Units outstanding at the time) as of the end of the Company's most recent quarter-end. 5. GRANT OF SECURITY INTEREST. (a) The Company hereby grants to the Holder a first priority security interest in all of the intellectual property rights transferred from the Holder to the Company set forth on Schedule I hereto (the "Intellectual Property"), in order to secure the payment and performance in full of all obligations of the Company now or hereafter existing under this Note. The security interest granted herein will terminate (and all rights to the Intellectual Property will revert to the Company) upon the payment and performance in full of all such obligations or the exercise by the Holder of the conversion option set forth in Section 3(a) above. (b) At any time and from time to time, the Company (at the Company's expense) will promptly execute and deliver all further instruments, and will take all further action, that may be necessary or desirable, or that the Holder may reasonably request, in order to perfect and protect any security interest granted or purported to be granted hereby or to enable the Holder to exercise and endorse its rights and remedies hereunder with respect to the Intellectual Property. 6. PREPAYMENTS. The Company shall not prepay any portion of the principal of this Note without the prior written consent of the Holder. 7. REQUIRED CONSENT. The Company may not modify any of the terms of this Note without the prior written consent of the Holder. 8. LOST DOCUMENTS. Upon receipt by the Company of evidence satisfactory to it of the loss, theft, destruction or mutilation of this Note or any Note exchanged for it, and (in the case of loss, theft or destruction) of indemnity satisfactory to it, and upon reimbursement to the Company of all reasonable expenses incidental thereto, and upon surrender and cancellation of such Note, if mutilated, the Company will make and deliver in lieu of such Note a new Note of like tenor and unpaid principal amount and dated as of the original date of the Note. 9. MISCELLANEOUS. 9.1 SEVERABILITY. In case any one or more of the provisions contained in this Note should be invalid, illegal or unenforceable in any respect, the validity, legality and enforceability of the remaining provisions contained herein shall not in any way be affected or impaired thereby. 4  9.2 NOTICES AND ADDRESSES. All notices, offers, acceptances and any other acts under this Note (except payment) shall be in writing, and shall be sufficiently given if delivered to the addressee in person, by Federal Express or similar receipted delivery, by facsimile delivery or, if mailed, postage prepaid, by certified mail, return receipt requested, as follows: To Holder: NYFIX, Inc. Stamford Harbor Park 333 Ludlow Street Stamford, Connecticut 06902 Attn: Peter K. Hansen, CEO Fax: (203) 425-8100 With a copy to: Olshan Grundman Frome Rosenzweig & Wolosky LLP 505 Park Avenue New York, New York 10002 Attn: Benjamin S. Reichel, Esq. Fax: (212) 935-1787 To the Company : Renaissance Trading Technologies, LLC 44 Wall Street New York, New York 10005 Attn: Edward Brandman, CEO Fax: (212) ______________ With a copy to: Hogan & Hartson LLP 555 13th Street, NW Washington, DC 20004 Attn: John Beckman, Esq. Fax: (202) 637-5464 or to such other address as any of them, by notice to the others may designate from time to time. Time shall be counted to, or from, as the case may be, the delivery in person or five (5) business days after mailing. 9.3 GOVERNING LAW. This Note and any dispute, disagreement, or issue of construction or interpretation arising hereunder, whether relating to its execution, its validity, the obligations provided therein or performance, shall be governed and interpreted according to the law of the State of New York. 9.4 BINDING EFFECT; ASSIGNMENT. This Note and the various rights and obligations arising hereunder shall inure to the benefit of and be binding upon the parties hereto and their respective successors and permitted assigns. Neither this Note nor any of the rights, interests or obligations hereunder shall be transferred or assigned (by operation of law or otherwise) by the Company without the prior written consent of the Holder. 5  Neither this Note nor any of the rights, interests or obligations hereunder shall be transferred or assigned (by operation of law or otherwise) by the Holder without the prior written consent of the Company, except that this Note may be assigned by the Holder to any entity in which NYFIX, Inc. owns at least an 80% direct or indirect equity interest. Any transfer or assignment of any of the rights, interests or obligations hereunder in violation of the terms hereof shall be void and of no force or effect. 9.5 JURISDICTION AND VENUE. Each of the Holder and the Company (i) agree that any legal suit, action or proceeding arising out of or relating to this Note shall be instituted exclusively in the courts of the State of New York, (ii) waive any objection to the venue of any such suit, action or proceeding and the right to assert that such forum is not a convenient forum, and (iii) irrevocably consent to the jurisdiction of the courts of the State of New York in any such suit, action or proceeding, and further agree to accept and acknowledge service of any and all process which may be served in any such suit, action or proceeding and agree that service of process upon them mailed by certified mail to their respective addresses shall be deemed in every respect effective service of process upon them in any such suit, action or proceeding. 9.6 SECTION HEADINGS. Section headings herein have been inserted for reference only and shall not be deemed to limit or otherwise affect, in any matter, or be deemed to interpret in whole or in part any of the terms or provisions of this Note. IN WITNESS WHEREOF, the Company has caused this Note to be made and issued in its name on the date specified above by the duly authorized representative of the Company. RENAISSANCE TRADING TECHNOLOGIES, LLC By: /s/ Daniel J. Ryan ---------------------------------- Name: Daniel J. Ryan Title: EVP and CFO 6  SCHEDULE I List of Intellectual Property "Renaissance" is the Nasdaq Market Making /Trading system that was developed at Robertson Stephens as an alternative to the existing vendor supplied system. The basic scope of the Renaissance system can be summarized as follows: * Order Management and Routing * Execution Management/AutoEx * Position Management * Real-time P&L * Quote Management * Nasdaq Compliance Rules The Source Code and Supporting Documentation consists of the following: * All software versions for all platforms and operating environments * All specifications, technical or programmers' notes, source code annotations, user guides, manuals, files, instructions, software architecture designs, flowcharts, plans, drawings, diagrams, and documentation that are exclusively related to the Software 7