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                                                                    Exhibit 10.4

            AMENDED AND RESTATED RESTRICTED STOCK AGREEMENT

         THIS AMENDED AND RESTATED RESTRICTED STOCK AGREEMENT (this
 "AGREEMENT"), dated as of January 15, 2004, is entered into by and among
 optionsXpress, Inc., a Delaware corporation (the "CORPORATION"), James Gray, as
 trustee of the AVRUM GRAY DELTA TRUST FOR JIM U/A/D JUNE 7, 2002 (the "TRUST"),
 and James Gray individually ("EXECUTIVE").

         WHEREAS, Executive and the Corporation are parties to that certain
 Restricted Stock Agreement dated as of November 13, 2000 (the "PRIOR
 AGREEMENT");

         WHEREAS, as permitted by the terms of the Prior Agreement, on or about
 June 10, 2002, Executive transferred 700,000 shares (the "SHARES") of common
 stock ("COMMON STOCK") of the Corporation to the Trust;

         WHEREAS, the Shares are subject to certain contractual restrictions set
forth in the Prior Agreement;

         WHEREAS, pursuant to the terms of the Prior Agreement, substantially
all of the Shares have vested; and

         WHEREAS, in connection with the consummation of the transactions
 contemplated by that certain Stock Purchase and Recapitalization Agreement,
 dated as of December 17, 2003 (the "RECAPITALIZATION AGREEMENT"), among the
 Corporation, the purchasers identified therein (collectively referred to herein
 as the "INVESTORS"), the Trust and the other stockholders of the Corporation
 identified therein, the Corporation, Executive and the Trust wish to amend and
 restate the Prior Agreement in its entirety in accordance with the terms
 contained herein.

         NOW, THEREFORE, in consideration of the premises and the mutual
 covenants set forth in this Agreement and for other good and valuable
 consideration, the receipt and sufficiency of which are hereby acknowledged,
 the parties hereto have agreed, and do hereby agree, as follows:

         1.    RESTRICTED SHARES. Executive and the Trust hereby acknowledge the
restrictions on the Shares pursuant to the terms and conditions herein set
forth. Such Shares, along with any shares of the Corporation's capital stock
issued with respect to such Shares by way of a stock-split, stock dividend or
other recapitalization affecting Common Stock subsequent to the date hereof,
shall be referred to herein as the "RESTRICTED SHARES."

         2.    VESTING. The Corporation, Executive and the Trust acknowledge and
agree that, as of the date hereof, all of the Restricted Shares are vested in
favor of Executive and the Trust (the "VESTED RESTRICTED SHARES").

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         3.    RESTRICTIONS ON RESTRICTED SHARES.

               (a)  VESTED RESTRICTED SHARES.

                    (i) The Vested Restricted Shares may not be sold, assigned,
         transferred, pledged, gifted, encumbered, alienated, hypothecated or
         otherwise disposed of and any attempt to do so shall be void and of no
         legal force or effect whatsoever.

                    (ii) Notwithstanding the foregoing, Vested Restricted Shares
         may be transferred (A) if the majority of the Corporation's board of
         directors approves such transfer, (B) in connection with a Change in
         Control (as defined below), (C) to the Corporation or the Other
         Stockholders as provided in this SECTION 3 or SECTION 4, or (D) to a
         Permitted Transferee (as defined below); PROVIDED that the Permitted
         Transferee thereof has agreed in a writing (in a form approved by the
         Corporation) delivered to the Corporation to be bound by the terms of
         this Agreement with all of the rights and obligations of Executive as
         if such Permitted Transferee was Executive; PROVIDED FURTHER, that all
         references to Executive's employment shall remain in reference to
         Executive and shall not refer to such Permitted Transferee.

               (b)  For purposes hereof, "CHANGE IN CONTROL" means a merger,
consolidation, sale or conveyance of all or substantially all of the
Corporation's assets or shares pursuant to which the holders of the voting
securities of the Corporation immediately before the transaction own immediately
after the transaction less than a majority of the outstanding voting securities
of the surviving entity (or its parent) or the purchasing entity (or its
parent), as the case may be.

               (c)  For purposes hereof, "PERMITTED TRANSFEREE" with respect to
Executive or the Trust means (i) James Gray; (ii) a transferee receiving Vested
Restricted Shares pursuant to applicable laws of descent and distribution; (iii)
a trust whose beneficiary(ies) is Executive, Executive's spouse or a member of
Executive's immediate family; PROVIDED that Executive is the trustee of such
trust and the trust instrument governing said trust provides that Executive, as
trustee, retains sole and exclusive control over the voting and disposition of
said Vested Restricted Shares until the termination of this Agreement; (iv) a
partnership whose owners are Executive, his spouse and/or his immediate family;
PROVIDED that the partnership agreement governing said partnership provides that
Executive retains sole and exclusive control over the voting and disposition of
said Vested Restricted Shares until the termination of this Agreement; (v) a
limited liability company whose owners are Executive, his spouse and/or his
immediate family; PROVIDED that the limited liability company agreement
governing such limited liability company provides that Executive retains sole
and exclusive control over the voting and disposition of said Vested Restricted
Shares until the termination of this Agreement; (vi) the Corporation; (vii) a
transferee receiving Vested Restricted Shares pursuant to a Change in Control;
(viii) any pledgee of up to 30% of the value of such Vested Restricted Shares
(as determined by the Corporation's board of directors at the time of such loan
transaction) in support of a bona fide loan transaction for Executive's benefit
(E.G., the holder of Vested Restricted Shares valued at $10,000,000 at the time
of such loan transaction may pledge all of such shares as collateral security
for a loan of up to $3,000,000) so long as, as a condition to any such pledge,
the third party lender agrees to grant the Corporation and the Other
Stockholders the

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right to repurchase any such Vested Restricted Shares upon any default or
foreclosure in respect thereof by the applicable lender on terms and conditions
satisfactory to the board of directors of the Corporation (including the
"Investor Director", as such term is defined in the Stockholders Agreement); and
(ix) a not-for-profit charitable entity. For purposes of this Agreement,
"STOCKHOLDERS AGREEMENT" shall have the meaning assigned to such term in the
Recapitalization Agreement.

               (d)  TRANSFERS BY OPERATION OF LAW. In the event that a transfer
of Restricted Shares to a person or entity (a "TRANSFEREE") is effected by
operation of law (including, but not limited to, bankruptcy, or divorce and
dissolution of marriage) other than by reason of the death of Executive and
excluding transfers to a Permitted Transferee (an "OPERATION OF LAW TRANSFER"),
the following shall apply:

                    (i)   The Corporation shall have the right, but not the
         obligation, to purchase from the Transferee any or all of the
         Restricted Shares transferred or proposed to be transferred pursuant to
         the Operation of Law Transfer.

                    (ii)  If the Corporation does not exercise its right under
         clause (i) above to purchase from the Transferee any or all of the
         Restricted Shares transferred or proposed to be transferred pursuant to
         the Operation of Law Transfer (the "REMAINING INVOLUNTARY SHARES")
         within six (6) months following the later of (A) the effective date of
         the Operation of Law Transfer and (B) the date upon which the
         Corporation's board of directors acquires actual notice of the
         Operation of Law Transfer, then the Corporation shall promptly notify
         in writing the Other Stockholders (as defined below), and the Other
         Stockholders shall have the right to purchase all or any portion of
         their pro rata portion of the Remaining Involuntary Shares (as such pro
         rata portion is determined pursuant to the terms of the Stockholders
         Agreement) on the terms set forth in this SECTION 3 and SECTION 5.
         Notwithstanding anything to the contrary contained herein, the
         restrictions contained in this Agreement shall not be applicable to
         any Other Stockholders who exercise their rights to purchase any
         Restricted Shares pursuant to this SECTION 3.

                    (iii) The purchase price for the Restricted Shares purchased
         by the Corporation and/or the Other Stockholders pursuant to this
         SECTION 3 shall be equal to eighty percent (80%) of the Fair Market
         Value (as defined below) of the transferred Restricted Shares as of the
         effective date of the Operation of Law Transfer.

                    (iv)  The purchase options contained in clauses (i) and (ii)
         above shall be exercisable by written notice to the Transferee provided
         by the Corporation and, if applicable, the Other Stockholders within
         one (1) year following the later of (A) the effective date of the
         Operation of Law Transfer and (B) the date upon which the Corporation's
         board of directors acquires actual notice of the Operation of Law
         Transfer.

                    (v)   If the purchase price to be paid to the Transferee is
         in excess of five thousand dollars ($5,000), the Corporation may, in
         its sole option, pay all or any portion of such purchase price by
         delivering to the transferee a promissory note which: (A) shall be
         payable in installments payable on the first three (3) anniversaries
         of the date of purchase, each installment consisting of one-third
         (1/3) of the principal amount of the

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         note plus interest from the date of the note at a rate of interest
         equal to the "APPLICABLE FEDERAL RATE" (as defined in the United States
         Internal Revenue Code of 1986, as amended) in effect at the time of
         purchase; (B) shall permit pre-payment in whole or part at any time,
         without penalty; (C) shall be secured by a pledge of the purchased
         Restricted Shares; (D) shall provide for forgiveness of all outstanding
         principal and interest in the event of the liquidation of the
         Corporation, in which event the Corporation will be deemed to have
         purchased only that portion of the Restricted Shares that is equal in
         proportion to the proportion of the purchase price actually paid by the
         Corporation up to the date of such liquidation; and (E) shall contain
         other details customary for notes of this type.

                    (vi)  If the purchase price to be paid to the Transferee is
         less than or equal to five thousand dollars ($5,000), the Corporation
         shall pay such purchase price within sixty (60) calendar days of the
         exercise of the option set forth in SECTION 3(c)(i).

         4.    REPURCHASE OF VESTED RESTRICTED SHARES.

               (a)  TERMINATION BY THE CORPORATION FOR CAUSE.

                    (i)   If the Corporation terminates Executive's employment
         with the Corporation for Cause (as defined below) (other than by reason
         of the commission of fraud, theft or embezzlement by Executive in
         connection with his duties to the Corporation or any of its customers
         or other material business relations), then the Corporation shall have
         the right, but not the obligation, at any time thereafter, to
         repurchase, in accordance with this SECTION 4 and SECTION 5, all of the
         Vested Restricted Shares at a price per share equal to seventy percent
         (70%) of the Fair Market Value per share as of the effective date of
         such termination.

                    (ii)  If the Corporation terminates Executive's employment
         for Cause by reason of the commission of fraud, theft or embezzlement
         by Executive in connection with his duties to the Corporation or any of
         its customers or other material business relations, then the
         Corporation shall have the right, but not the obligation, at any time
         thereafter, to repurchase all of the Vested Restricted Shares for
         $0.0002 per share in accordance with SECTION 5.

               (b)  TERMINATIONS OTHER THAN FOR CAUSE OR WITH GOOD REASON.

                    (i)   If, on or prior to the third anniversary of the date
         of this Agreement, (A) the Corporation terminates Executive's
         employment with the Corporation for any reason other than for Cause
         (including termination by reason of death or disability under SECTION
         5(a)(iii) of the Employment Letter (as defined below)), or (B)
         Executive resigns with Good Reason, then the Corporation shall have
         the obligation, within one-hundred eighty (180) days (the "PUT
         PURCHASE DATE") following its receipt of a written request of
         Executive (a "PUT REQUEST"), which Put Request must be delivered (if
         at all) within sixty (60) days following any such termination of
         employment described in clauses (A) or (B) above, to repurchase in
         accordance with this SECTION 4 and SECTION 5 all of the Vested
         Restricted Shares at a purchase price equal to

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         seventy-five percent (75%) of the Fair Market Value per share as of the
         effective date of such termination.

                    (ii)  If (A) the circumstances enabling Executive to make a
         Put Request occur but Executive does not make a Put Request, (B)
         Executive's employment is terminated by the Corporation for any reason
         other than for Cause subsequent to the third anniversary date of this
         Agreement, or (C) Executive resigns for Good Reason subsequent to the
         third anniversary date of this Agreement, the Corporation shall have
         the right, but not the obligation, at any time thereafter, to
         repurchase in accordance with this SECTION 4 and SECTION 5 all or any
         portion of the Vested Restricted Shares at a price equal to the Fair
         Market Value per share as of the effective date of such termination.

                    (iii) If Executive resigns without Good Reason, the
         Corporation shall have the right, but not the obligation, at any time
         thereafter, to repurchase in accordance with this SECTION 4 and
         SECTION 5 all or any portion of the Vested Restricted Shares at a
         price equal to seventy-five percent (75%) of the Fair Market Value per
         share as of the effective date of such termination.

         If the funds of the Corporation legally available for repurchase of
         Vested Restricted Shares upon a Put Request are insufficient to
         repurchase the total number of Vested Restricted Shares to be
         repurchased on such date, those funds which are legally available
         (subject to regulatory capital requirements) will be used to purchase
         the maximum possible number of Vested Restricted Shares. Thereafter,
         when additional funds of the Corporation are legally available for the
         repurchase of such shares, such funds (subject to regulatory capital
         requirements) will be promptly used to repurchase the balance of the
         Vested Restricted Shares which the Corporation became obligated to
         repurchase upon the Put Request but which it has not repurchased.

               (c)  OTHER STOCKHOLDER OPTION. If the Corporation does not
 exercise its purchase option under SECTION 4(a)(i) or SECTION 4(b), if
 applicable, within ninety (90) days after the effective date of the termination
 of Executive's employment with the Corporation, then the Corporation shall
 promptly so notify the Other Stockholders in writing (the "CORPORATION
 NOTICE"), and the Other Stockholders shall have the right to purchase all or
 any portion of their pro rata portion of the Vested Restricted Shares (as such
 pro rata portion is determined pursuant to the terms of the Stockholders
 Agreement) on the terms set forth in this SECTION 4 and SECTION 5 by giving the
 Corporation and Executive written notice of the exercise of such right within
 ten (10) days after delivery of the Corporation Notice. Notwithstanding
 anything to the contrary contained herein, the restrictions contained in this
 Agreement shall not be applicable to any Other Stockholders who exercise their
 rights to purchase any Vested Restricted Shares pursuant to this SECTION 4.

               (d)  CERTAIN DEFINED TERMS.   For purposes hereof, the following
terms shall have the meanings set forth below:

                    (i)   "CAUSE" shall have the definition given to such term
         in that certain Employment Letter Agreement dated as of January 15,
         2004, between the Corporation

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         and Executive, as amended, restated or otherwise modified from time to
         time (the "EMPLOYMENT LETTER").

                    (ii)  "FAIR MARKET VALUE" shall mean the average of the
         closing prices of the Common Stock's sales on all securities exchanges
         on which such security may at the time be listed, or, if there has been
         no sales on any such exchange on any day, the average of the highest
         bid and lowest asked prices on all such exchanges at the end of such
         day, or, if on any day such security is not so listed, the average of
         the representative bid and asked prices quoted in the NASDAQ System as
         of 4:00 P.M., New York time, or, if on any day such security is not
         quoted in the NASDAQ System, the average of the highest bid and lowest
         asked prices on such day in the domestic over-the-counter market as
         reported by the National Quotation Bureau, Incorporated, or any similar
         successor organization, in each such case averaged over a period of
         twenty-one (21) days consisting of the day as of which "FAIR MARKET
         VALUE" is being determined and the twenty (20) consecutive business
         days prior to such day. If at any time such security is not listed on
         any securities exchange or quoted in the NASDAQ System or the
         over-the-counter market, the "FAIR MARKET VALUE" shall be the fair
         value thereof determined jointly by the Corporation and Executive. If
         such parties are unable to reach agreement within a reasonable period
         of time, not to exceed thirty (30) days, the "FAIR MARKET VALUE" shall
         be determined by an independent appraiser experienced in valuing
         securities jointly selected by the Corporation and Executive in good
         faith and within five (5) days of the expiration of such thirty-day
         period. The determination of such appraiser shall be final and binding
         upon the parties, and the fees and expenses of such appraiser shall be
         borne equally by the Corporation and Executive. The date on which the
         Fair Market Value is finally determined (as opposed to the effective
         date as of which the Fair Market Value is calculated for purposes of
         this Agreement) in accordance with the foregoing provisions shall be
         referred to herein as the "VALUATION DATE."

                    (iii) "GOOD REASON" shall have the definition given to such
         term in the Employment Letter.

                    (iv)  "OTHER STOCKHOLDERS" shall mean, collectively, the
         Investors, G-Bar Limited Partnership, David Kalt and Ned Bennett.

         5.    CLOSING AND TERMS.

               (a)  PAYMENT TERMS. If the purchase price for the Restricted
Shares purchased in accordance with SECTION 4 is less than $500,000, it shall be
paid in one installment. If the purchase price is greater than $2,500,000, it
shall be paid in five equal annual installments. If the purchase price is
greater than $500,000 but less than $2,500,000, the purchase price will be paid
in consecutive annual installments of $500,000 until the unpaid balance of the
purchase price is less than $500,000, and a final annual installment shall be
payable thereafter equal to the unpaid balance of the purchase price. The first
installment of the purchase price shall be paid at the Closing (as defined
below), and subsequent annual installments, if any, shall be due on the
successive anniversary dates of the Closing. Interest shall accrue from the date
of the Closing on the balance of the purchase price remaining unpaid from time
to time at the prime rate published in the Midwest edition of THE WALL STREET
JOURNAL on the date of the Closing, and accrued interest

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shall be payable together with each annual installment of the purchase price.
All or part of the purchase price may be prepaid without penalty or premium.
Notwithstanding the foregoing or any other provision contained herein, the
purchase price for any Restricted Shares (i) purchased by any Other Stockholders
upon the exercise of any rights under SECTION 3 or 4 hereof shall be paid in
cash at the Closing (as defined below), and (ii) shall accelerate and become
immediately due and payable upon a Change in Control.

               (b)  CLOSING.

                    (i)   Except as otherwise provided herein, the Restricted
         Shares shall be purchased and sold in accordance with these provisions
         at the offices of the Corporation or its legal counsel at 10:00 a.m. on
         the date set forth in this SECTION 5 (the "CLOSING").

                    (ii)  The Closing of any purchase of Restricted Shares by
         the Corporation or the Other Stockholders pursuant to SECTION 4 shall
         take place on the following dates, as applicable:

                          (A) If the purchase is pursuant to SECTION 4(a)(i),
               SECTION 4(b)(ii) or SECTION 4(b)(iii), the Corporation (or the
               Other Stockholders, if applicable) shall give the holder of
               Restricted Shares written notice of the exercise of such purchase
               option and the Closing shall occur on the later of (A) the tenth
               (l0th) day following the Valuation Date and (B) the sixtieth
               (60th) day following delivery of such notice.

                          (B) If the purchase is pursuant to SECTION 4(b)(i),
               the Closing shall occur on the later of (A) the tenth (10th) day
               following the Valuation Date and (B) the Put Purchase Date, but
               in no event later than forty-five (45) days after the Put
               Purchase Date; PROVIDED, HOWEVER, that the timing of the
               Corporation's payment of the purchase price shall, if applicable,
               be subject to the last paragraph of Section 4(b).

                    (iii) The Corporation shall give Executive, his Permitted
         Transferees, or his heirs or personal representative, as the case may
         be (the "SELLING STOCKHOLDER"), at least twenty (20) days' prior
         written notice of the time, date and place of the Closing of any
         purchase under SECTION 4(a)(ii).

               (c)  TRANSFER DOCUMENTS. At the Closing, the Selling Stockholder
shall deliver to the Corporation stock certificates duly endorsed for transfer,
or accompanied by duly endorsed stock powers, representing all of the Restricted
Shares being sold, free and clear of all claims, liens, or encumbrances,
together with such other documentation as the Corporation's legal counsel may
reasonably require, and the Corporation shall act as agent for the Other
Shareholders with respect to any sale under SECTION 3.

               (d)  FAILURE TO TRANSFER RESTRICTED SHARES. If the Selling
Stockholder fails, for any reason, to tender any certificates representing
Restricted Shares in accordance with SECTION 3, 4 or 5, the Corporation may, at
its option, in addition to all other remedies it may have, send to the Selling
Stockholder the purchase price for such Restricted Shares as is herein
specified. Thereupon, the Corporation shall cancel on its books the certificate
or certificates

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representing the Restricted Shares to be repurchased and all of the Selling
Stockholder's rights in and to such Restricted Shares shall terminate. If the
Corporation and the Other Stockholders do not repurchase all of the shares
represented by such certificate, the Corporation will issue a new certificate to
the Selling Stockholder representing the Restricted Shares which were not
repurchased by the Corporation and the Other Stockholders.

         6.    ADDITIONAL RESTRICTIONS ON TRANSFER OF RESTRICTED SHARES.

               (a)  LEGEND.  The certificates representing Restricted Shares
will bear the following legend:

         "THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN
         REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, AND MAY NOT BE
         SOLD OR OFFERED FOR SALE IN THE ABSENCE OF A REGISTRATION STATEMENT
         WHICH IS EFFECTIVE UNDER THAT ACT AS TO SUCH SECURITIES OR AN OPINION,
         IN FORM AND SUBSTANCE SATISFACTORY TO THE CORPORATION AND GIVEN BY
         COUNSEL SATISFACTORY TO THE CORPORATION, TO THE EFFECT THAT SUCH
         REGISTRATION IS NOT REQUIRED."

         "THE SECURITIES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO
         ADDITIONAL RESTRICTIONS ON TRANSFER SET FORTH IN AN AMENDED AND
         RESTATED RESTRICTED STOCK AGREEMENT (THE "AGREEMENT") BETWEEN THE
         CORPORATION AND THE HOLDER HEREOF, DATED AS OF JANUARY 15, 2004, A COPY
         OF WHICH MAY BE OBTAINED AT THE PRINCIPAL EXECUTIVE OFFICE OF THE
         CORPORATION. ANY TRANSFER OR PLEDGE IN CONFLICT WITH, OR IN DEROGATION
         OF, THE AGREEMENT IS VOID AND OF NO LEGAL FORCE, EFFECT OR VALIDITY
         WHATSOEVER."

               (b)  SECURITIES ACT. In addition to any other restriction set
forth herein, no holder of Restricted Shares may sell, transfer, or dispose of
any Restricted Shares (except pursuant to an effective registration statement
under the Securities Act of 1933, as amended, and the rules and regulations
promulgated thereunder (the "SECURITIES ACT")) without first delivering to the
Corporation an opinion of counsel reasonably acceptable in form and substance to
the Corporation that registration under the Securities Act is not required in
connection with such transfer; provided, however, that such requirement may be
waived by the Corporation's Board of Directors in its sole discretion.

         7.    TAX CONSEQUENCES. The Corporation shall not be liable or
responsible in any way for the tax consequences to the holder of the Restricted
Shares relating to the Restricted Shares or the lapse of the restrictions
hereunder. Executive agrees to determine and be responsible for any and all tax
consequences to himself relating to the Restricted Shares. If as a result of
this Agreement or otherwise, the Corporation is obligated to withhold an amount
on account of any tax imposed in connection with the termination of any
restrictions or limitations in respect of Restricted Shares, Executive shall be
required to pay such amount to the Corporation.

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         8.    VOTING. Executive shall continue to have the right to vote all of
the Restricted Shares on all matters submitted to holders of Common Stock.

         9.    DISTRIBUTIONS. The holder of the Restricted Shares shall have the
right to receive all cash dividends or other distributions with respect to all
of the Restricted Shares.

         10.   NO EMPLOYMENT RIGHTS. No provision of this Agreement shall give
Executive any right to continue in the employ of the Corporation, create any
inference as to the length or term of Executive's employment, affect the right
of the Corporation to terminate Executive's employment, with or without Cause,
or give Executive any right to participate in any employee welfare or benefit
plan or other program of the Corporation.

         11.   TERMINATION. Upon the consummation of a Qualified IPO, this
Agreement and, particularly, the provisions of SECTIONS 3, 4 and 5 hereof, shall
automatically terminate. At the request of Executive, the Trust or other
Permitted Transferee, the second legend referenced in SECTION 6(a) shall be
removed from each certificate representing any of the Restricted Shares upon the
consummation of a Qualified IPO. For purposes hereof, "QUALIFIED IPO" means an
underwritten public offering of Common Stock or of equity securities of a
successor to the Corporation pursuant to the Securities Act with gross proceeds
in excess of $20,000,000.

         12.   NO DISCLOSURE RIGHTS. The Corporation shall have no duty or
obligation to affirmatively disclose to Executive, the Trust or his or its
representatives, and no such person or entity shall have the right to be advised
of, any material information regarding the Corporation at any time prior to,
upon or in connection with the termination of Executive's employment with the
Corporation, either by Executive or by the Corporation, or in connection with
the Corporation's repurchase of Restricted Shares in accordance with the terms
of this Agreement.

         13.   NOTICES. Any notice, consents or other communications required to
be sent or given hereunder by any of the parties shall in every case be in
writing and shall be deemed properly served if (a) delivered personally, (b)
sent by registered or certified mail, in all such cases with first class postage
paid, return receipt requested, (c) delivered by a recognized overnight courier
service, or (d) sent by facsimile transmission (with written or facsimile
confirmation of receipt) to the parties at the addresses or facsimile number, as
the case may be, as set forth below or at such other addresses or facsimile
number as may be furnished in writing pursuant to this SECTION 13.

               To the Corporation or
               the Other Shareholders:   optionsXpress, Inc,
                                         39 S. LaSalle St., Suite 220
                                         Chicago, Illinois 60603
                                         Attention: President
                                         Facsimile: (312)629-5256

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               With a copy to:           Katten Muchin Zavis Rosenman
                                         525 West Monroe Street Suite 1600
                                         Chicago, Illinois 60661-3693
                                         Attention: Brian F. Richards, Esq.
                                         Facsimile: (312)902-1061

               To Executive and/or
               the Trust:                Mr. James Gray
                                         440 South LaSalle Street, Suite 650
                                         Chicago, Illinois 60605
                                         Facsimile: (312)362-4208

               With a copy to:           Vedder, Price, Kaufman & Kammholz, P.C.
                                         222 North LaSalle Street
                                         Chicago, Illinois 60601
                                         Attention: Michael A. Nemeroff, Esq.
                                         Facsimile: (312)609-5005

Any notice under this Agreement will be deemed to have been given (a) on the
date such notice is personally delivered, (b) three (3) days after the date of
mailing if sent by certified or registered mail, (c) one (1) day after the date
such notice is delivered to the overnight courier service if sent by overnight
courier or (d) if by facsimile transmission, on the date of transmission.

         14.   SEVERABILITY. Whenever possible, each provision of this Agreement
will be interpreted in such a manner as to be effective and valid under
applicable law, but if any provision of this Agreement is held to be invalid,
illegal or unenforceable in any respect under any applicable law or rule in any
jurisdiction, such invalidity, illegality or unenforceability will not affect
any other provision or any other jurisdiction, but this Agreement will be
reformed, construed and enforced in such jurisdiction as if such invalid,
illegal or unenforceable provision had never been contained herein.

         15.   COMPLETE AGREEMENT. This Agreement embodies the complete
agreement and understanding among the parties and supersedes and preempts any
prior understandings, agreements or representations by or among the parties,
written or oral, which may have related to the subject matter hereof in any way.

         16.   REMEDIES. Each of the parties to this Agreement will be entitled
to enforce its rights under this Agreement specifically, to recover damages by
reason of any breach of any provision of this Agreement and to exercise all
other rights existing in its favor. Each of Executive and the Trust agrees and
acknowledges that money damages will not be an adequate remedy for any breach of
the provisions of this Agreement and that the Corporation shall be entitled to
specific performance and/or injunctive relief in order to enforce or prevent any
violations of the provisions of this Agreement.

         17.   AMENDMENTS AND WAIVERS. Any provision of this Agreement may be
amended or waived only with the prior written consent of the Corporation,
Executive and the Trust.

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         18.   GOVERNING LAW. This Agreement shall be construed and enforced in
accordance with, and all questions concerning the construction, validity,
interpretation and performance of this Agreement shall be governed by, the laws
of the State of Delaware, without giving effect to provisions thereof regarding
conflict of laws.

         19.   WAIVER; CUMULATIVE RIGHTS. The failure or delay of either party
hereto to require performance by the other party of any provision hereof shall
not affect its right to require performance of such provision unless and until
such performance has been waived in writing. Each and every right hereunder is
cumulative and may be exercised in part or in whole from time to time.

         20.   SUCCESSORS AND ASSIGNS. This Agreement shall inure to the benefit
of and be binding upon each successor and assign of the Corporation. All
obligations imposed upon Executive and the Trust or his or its representatives,
and all rights granted to the Corporation hereunder, shall be binding upon
Executive and his heirs and legal representatives, and on the Trust or its
successors.

         21.   HEADINGS. The captions set forth in this Agreement are for
convenience only and shall not be considered as part of this Agreement or as in
any way limiting the terms and provisions hereof.

         22.   COUNTERPARTS. This Agreement may be executed on separate
counterparts, each of which is deemed to be an original and all of which taken
together constitute one and the same agreement.

         23.   NO STRICT CONSTRUCTION. The language used in this Agreement will
be deemed to be the language chosen by the parties hereto to express their
mutual intent, and no rule of strict construction will be applied against any
party hereto.

                  [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]

                                       11

<Page>

       (SIGNATURE PAGE TO AMENDED AND RESTATED RESTRICTED STOCK AGREEMENT)

         IN WITNESS WHEREOF, the undersigned have each caused this Amended and
Restated Restricted Stock Agreement to be duly executed, individually or by a
duly authorized representative as applicable, all as of the day and year first
above written.

                                     OPTIONSXPRESS, INC., a Delaware corporation

                                       /s/ David Kalt
                                     -------------------------------------------
                                     David Kalt, President

                                       /s/ James Gray
                                     -------------------------------------------
                                     James Gray

                                     AVRUM GRAY DELTA TRUST FOR
                                     JIM U/A/D JUNE 7, 2002

                                     By:  /s/ James Gray
                                        -----------------------------------
                                        James Gray, Trustee<Page>

                                                                    Exhibit 10.5

                 AMENDED AND RESTATED RESTRICTED STOCK AGREEMENT

         THIS AMENDED AND RESTATED RESTRICTED STOCK AGREEMENT (this
"AGREEMENT"), dated as of January 15, 2004, is entered into between
optionsXpress. Inc., a Delaware corporation (the "CORPORATION"), and David Kalt
("EXECUTIVE").

         WHEREAS, Executive and the Corporation are parties to that certain
Restricted Stock Agreement dated as of November 13, 2000 (the "PRIOR
AGREEMENT");

         WHEREAS, Executive currently owns 650,000 shares (the "SHARES") of
common stock ("COMMON STOCK") of the Corporation which are subject to certain
contractual restrictions set forth in the Prior Agreement;

         WHEREAS, pursuant to the terms of the Prior Agreement, substantially
all of the Shares have vested; and

         WHEREAS, in connection with the consummation of the transactions
contemplated by that certain Stock Purchase and Recapitalization Agreement,
dated as of December 17, 2003 (the "RECAPITALIZATION AGREEMENT"), among the
Corporation, the purchasers identified therein (collectively referred to herein
as the "INVESTORS") and the stockholders of the Corporation identified therein,
the Corporation and Executive wish to amend and restate the Prior Agreement in
its entirety in accordance with the terms contained herein.

         NOW, THEREFORE, in consideration of the premises and the mutual
covenants set forth in this Agreement and for other good and valuable
consideration, the receipt and sufficiency of which are hereby acknowledged, the
parties hereto hove agreed, and do hereby agree, as follows:

         1.    RESTRICTED SHARES. Executive hereby acknowledges the restrictions
on the Shares pursuant to the terms and conditions herein set forth. Such
Shares, along with any shares of the Corporation's capital stock issued with
respect to such Shares by way of a stock-split, stock dividend or other
recapitalization affecting Common Stock subsequent to the date hereof, shall be
referred to herein as the "RESTRICTED SHARES."

         2.    VESTING. The Corporation and Executive acknowledge and agree
that, as of the date hereof, all of the Restricted Shares are vested in favor of
Executive (the "VESTED RESTRICTED SHARES").

         3.    RESTRICTIONS ON RESTRICTED SHARES.

               (a)  VESTED RESTRICTED SHARES.

                    (i)     The Vested Restricted Shares may not be sold,
         assigned, transferred, pledged, gifted, encumbered, alienated,
         hypothecated or otherwise disposed of and any attempt to do so shall be
         void and of no legal force or effect whatsoever.

                    (ii)    Notwithstanding the foregoing, Executive may
         transfer Vested Restricted Shares (A) if the majority of the
         Corporation's board of directors approves

<Page>

         such transfer, (B) in connection with a Change in Control (as defined
         below), (C) to the Corporation or the Other Stockholders as provided in
         this SECTION 3 or SECTION 4, or (D) to a Permitted Transferee (as
         defined below); PROVIDED that the Permitted Transferee thereof has
         agreed in a writing (in a form approved by the Corporation) delivered
         to the Corporation to be bound by the terms of this Agreement with all
         of the rights and obligations of Executive as if such Permitted
         Transferee was Executive; PROVIDED FURTHER, that all references to
         Executive's employment shall remain in reference to Executive and shall
         not refer to such Permitted Transferee.

               (b)  For purposes hereof, "CHANGE IN CONTROL" means a merger,
consolidation, sale or conveyance of all or substantially all of the
Corporation's assets or shares pursuant to which the holders of the voting
securities of the Corporation immediately before the transaction own immediately
after the transaction less than a majority of the outstanding voting securities
of the surviving entity (or its parent) or the purchasing entity (or its
parent), as the case may be.

               (c)  For purposes hereof, "PERMITTED TRANSFEREE" with respect to
Executive means (i) a transferee receiving Vested Restricted Shares pursuant to
applicable laws of descent and distribution; (ii) a trust whose beneficiary(ies)
is Executive, Executive's spouse or a member of Executive's immediate family;
PROVIDED that Executive is the trustee of such trust and the trust instrument
governing said trust provides that Executive, as trustee, retains sole and
exclusive control over the voting and disposition of said Vested Restricted
Shares until the termination of this Agreement; (iii) a partnership whose owners
are Executive, his spouse and/or his immediate family; PROVIDED that the
partnership agreement governing said partnership provides that Executive retains
sole and exclusive control over the voting and disposition of said Vested
Restricted Shares until the termination of this Agreement; (iv) a limited
liability company whose owners are Executive, his spouse and/or his immediate
family; PROVIDED that the limited liability company agreement governing such
limited liability company provides that Executive retains sole and exclusive
control over the voting and disposition of said Vested Restricted Shares until
the termination of this Agreement; (v) the Corporation; (vi) a transferee
receiving Vested Restricted Shares pursuant to a Change in Control; (vii) any
pledgee of up to 30% of the value of such Restricted Shares (as determined by
the Corporation's board of directors at the time of such loan transaction) in
support of a bona fide loan transaction for Executive's benefit (E.G., Executive
with Vested Restricted Shares valued at $10,000,000 at the time of such loan
transaction may pledge all of such shares as collateral security for a loan of
up to $3,000,000) so long as, as a condition to any such pledge, the third party
lender agrees to grant the Corporation and the Other Stockholders the right to
repurchase any such Vested Restricted Shares upon any default or foreclosure in
respect thereof by the applicable lender on terms and conditions satisfactory to
the board of directors of the Corporation (including the "Investor Director", as
such term is defined in the Stockholders Agreement); and (viii) a not-for-profit
charitable entity. For purposes of this Agreement, "STOCKHOLDERS AGREEMENT"
shall have the meaning assigned to such term in the Recapitalization Agreement.

               (d)  TRANSFERS BV OPERATION OF LAW. In the event that a transfer
of Restricted Shares to a person or entity (a "TRANSFEREE") is effected by
operation of law (including, but not limited to, bankruptcy, or divorce and
dissolution of marriage) other than by reason of the death

                                        2
<Page>

of Executive and excluding transfers to a Permitted Transferee (an "OPERATION OF
LAW TRANSFER"), the following shall apply:

                    (i)     The Corporation shall have the right, but not the
         obligation, to purchase from the Transferee any or all of the
         Restricted Shares transferred or proposed to be transferred pursuant to
         the Operation of Law Transfer.

                    (ii)    If the Corporation does not exercise its right under
         clause (i) above to purchase from the Transferee any or all of the
         Restricted Shares transferred or proposed to be transferred pursuant to
         the Operation of Law Transfer (the "REMAINING INVOLUNTARY SHARES")
         within six (6) months following the later of (A) the effective date of
         the Operation of Law Transfer and (B) the date upon which the
         Corporation's board of directors acquires actual notice of the
         Operation of Law Transfer, then the Corporation shall promptly notify
         in writing the Other Stockholders (as defined below), and the Other
         Stockholders shall have the right to purchase all or any portion of
         their pro rata portion of the Remaining Involuntary Shares (as such pro
         rata portion is determined pursuant to the terms of the Stockholders
         Agreement) on the terms set forth in this SECTION 3 and SECTION 5.
         Notwithstanding anything to the contrary contained herein, the
         restrictions contained in this Agreement shall not be applicable to any
         Other Stockholders who exercise their rights to purchase any Restricted
         Shares pursuant to this SECTION 3.

                    (iii)   The purchase price for the Restricted Shares
         purchased by the Corporation and/or the Other Stockholders pursuant to
         this SECTION 3 shall be equal to eighty percent (80%) of the Fair
         Market Value (as defined below) of the transferred Restricted Shares as
         of the effective date of the Operation of Law Transfer.

                    (iv)    The purchase options contained in clauses (i) and
         (ii) above shall be exercisable by written notice to the Transferee
         provided by the Corporation and, if applicable, the Other Stockholders
         within one (1) year following the later of (A) the effective date of
         the Operation of Law Transfer and (B) the date upon which the
         Corporation's board of directors acquires actual notice of the
         Operation of Law Transfer.

                    (v)     If the purchase price to be paid to the Transferee
         is in excess of five thousand dollars ($5,000), the Corporation may, in
         its sole option, pay all or any portion of such purchase price by
         delivering to the transferee a promissory note which: (A) shall be
         payable in installments payable on the first three (3) anniversaries of
         the date of purchase, each installment consisting of one-third (1/3) of
         the principal amount of the note plus interest from the date of the
         note at a rate of interest equal to the "APPLICABLE FEDERAL RATE" (as
         defined in the United States Internal Revenue Code of 1986, as amended)
         in effect at the time of purchase; (B) shall permit pre-payment in
         whole or part at any time, without penalty; (C) shall be secured by a
         pledge of the purchased Restricted Shares; (D) shall provide for
         forgiveness of all outstanding principal and interest in the event of
         the liquidation of the Corporation, in which event the Corporation
         will be deemed to have purchased only that portion of the Restricted
         Shares that is equal in proportion to the proportion of the purchase
         price actually paid by the Corporation up to the date of such
         liquidation; and (E) shall contain other details customary for notes
         of this type.

                                       3
<Page>

                    (vi)    If the purchase price to be paid to the Transferee
         is less than or equal to five thousand dollars ($5,000), the
         Corporation shall pay such purchase price within sixty (60) calendar
         days of the exercise of the option set forth in SECTION 3(c)(i).

         4.    REPURCHASE OF VESTED RESTRICTED SHARES.

               (a)  TERMINATION BY THE CORPORATION FOR CAUSE.

                    (i)     If the Corporation terminates Executive's employment
         with the Corporation for Cause (as defined below) (other than by reason
         of the commission of fraud, theft or embezzlement by Executive in
         connection with his duties to the Corporation or any of its customers
         or other material business relations), then the Corporation shall have
         the right, but not the obligation, at any time thereafter, to
         repurchase, in accordance with this SECTION 4 and SECTION 5, all of the
         Vested Restricted Shares at a price per share equal to seventy percent
         (70%) of the Fair Market Value per share as of the effective date of
         such termination.

                    (ii)    If the Corporation terminates Executive's employment
         for Cause by reason of the commission of fraud, theft or embezzlement
         by Executive in connection with his duties to the Corporation or any of
         its customers or other material business relations, then the
         Corporation shall have the right, but not the obligation, at any time
         thereafter, to repurchase all of the Vested Restricted Shares for
         $O.0002 per share in accordance with SECTION 5.

               (b)  TERMINATIONS OTHER THAN FOR CAUSE OR WITH GOOD REASON.

                    (i)     If, on or prior to the third anniversary of the date
         of this Agreement, (A) the Corporation terminates Executive's
         employment with the Corporation for any reason other than for Cause
         (including termination by reason of death or disability under
         Section 5(a)(iii) of the Employment Letter (as defined below)), or (B)
         Executive resigns with Good Reason, then the Corporation shall have the
         obligation, within one-hundred eighty (180) days (the "PUT PURCHASE
         DATE") following its receipt of a written request of Executive (a "PUT
         REQUEST"), which Put Request must be delivered (if at all) within sixty
         (60) days following any such termination of employment described in
         clauses (A) or (B) above, to repurchase in accordance with this
         SECTION 4 AND SECTION 5 all of the Vested Restricted Shares at a
         purchase price equal to seventy-five percent (75%) of the Fair Market
         Value per share as of the effective date of such termination.

                    (ii)    If (A) the circumstances enabling Executive to make
         a Put Request occur but Executive does not make a Put Request, (B)
         Executive's employment is terminated by the Corporation for any reason
         other than for Cause subsequent to the third anniversary date of this
         Agreement, or (C) Executive resigns for Good Reason subsequent to the
         third anniversary date of this Agreement, the Corporation shall have
         the right, but not the obligation, at any time thereafter, to
         repurchase in accordance with this SECTION 4 AND SECTION 5 all or any
         portion of the Vested Restricted Shares at a price equal to the Fair
         Market Value per share as of the effective date of such termination.

                                        4
<Page>

                    (iii)   If Executive resigns without Good Reason, the
         Corporation shall have the right, but not the obligation, at any time
         thereafter, to repurchase in accordance with this SECTION 4 AND
         SECTION 5 all or any portion of the Vested Restricted Shares at a price
         equal to seventy-five percent (75%) of the Fair Market Value per share
         as of the effective date of such termination.

         If the funds of the Corporation legally available for repurchase of
         Vested Restricted Shares upon a Put Request are insufficient to
         repurchase the total number of Vested Restricted Shares to be
         repurchased on such date, those funds which are legally available
         (subject to regulatory capital requirements) will be used to purchase
         the maximum possible number of Vested Restricted Shares. Thereafter,
         when additional funds of the Corporation are legally available for the
         repurchase of such shares, such funds (subject to regulatory capital
         requirements) will be promptly used to repurchase the balance of the
         Vested Restricted Shares which the Corporation became obligated to
         repurchase upon the Put Request but which it has not repurchased.

               (c)  OTHER STOCKHOLDER OPTION. If the Corporation does not
 exercise its purchase option under SECTION 4(a)(i) or SECTION 4(b), if
 applicable, within ninety (90) days after the effective date of the termination
 of Executive's employment with the Corporation, then the Corporation shall
 promptly so notify the Other Stockholders in writing (the "CORPORATION
 NOTICE"), and the Other Stockholders shall have the right to purchase all or
 any portion of their pro rata portion of the Vested Restricted Shares (as such
 pro rata portion is determined pursuant to the terms of the Stockholders
 Agreement) on the terms set forth in this SECTION 4 and SECTION 5 by giving the
 Corporation and Executive written notice of the exercise of such right within
 ten (10) days after delivery of the Corporation Notice. Notwithstanding
 anything to the contrary contained herein, the restrictions contained in this
 Agreement shall not be applicable to any Other Stockholders who exercise their
 rights to purchase any Vested Restricted Shares pursuant to this SECTION 4.

               (d)  CERTAIN DEFINED TERMS.  For purposes hereof, the following
terms shall have the meanings set forth below:

                    (i)     "CAUSE" shall have the definition given to such term
         in that certain Employment Letter Agreement dated as of January 15,
         2004, between the Corporation and Executive, as amended, restated or
         otherwise modified from time to time (the "EMPLOYMENT LETTER").

                    (ii)    "FAIR MARKET VALUE" shall mean the average of the
         closing prices of the Common Stock's sales on all securities exchanges
         on which such security may at the time be listed, or, if there has been
         no sales on any such exchange on any day, the average of the highest
         bid and lowest asked prices on all such exchanges at the end of such
         day, or, if on any day such security is not so listed, the average of
         the representative bid and asked prices quoted in the NASDAQ System as
         of 4:00 P.M., New York time, or, if on any day such security is not
         quoted in the NASDAQ System, the average of the highest bid and lowest
         asked prices on such day in the domestic over-the-counter market as
         reported by the National Quotation Bureau, Incorporated, or any similar
         successor organization, in each such case averaged over a period of
         twenty-one (21) days consisting

                                       5
<Page>

         of the day as of which "FAIR MARKET VALUE" is being determined and the
         twenty (20) consecutive business days prior to such day. If at any time
         such security is not listed on any securities exchange or quoted in the
         NASDAQ System or the over-the-counter market, the "FAIR MARKET VALUE"
         shall be the fair value thereof determined jointly by the Corporation
         and Executive. If such parties are unable to reach agreement within a
         reasonable period of time, not to exceed thirty (30) days, the "FAIR
         MARKET VALUE" shall be determined by an independent appraiser
         experienced in valuing securities jointly selected by the Corporation
         and Executive in good faith and within five (5) days of the expiration
         of such thirty-day period. The determination of such appraiser shall be
         final and binding upon the parties, and the fees and expenses of such
         appraiser shall be borne equally by the Corporation and the Executive.
         The date on which the Fair Market Value is finally determined (as
         opposed to the effective date as of which the Fair Market Value is
         calculated for purposes of this Agreement) in accordance with the
         foregoing provisions shall be referred to herein as the "VALUATION
         DATE."

                    (iii)   "GOOD REASON" shall have the definition given to
         such term in the Employment Letter.

                    (iv)    "OTHER STOCKHOLDERS" shall mean, collectively, the
         Investors, G-Bar Limited Partnership, Avrum Gray Delta Trust and Ned
         Bennett.

         5.    CLOSING AND TERMS.

               (a)  PAYMENT TERMS. If the purchase price for the Restricted
Shares purchased in accordance with SECTION 4 is less than $500,000, it shall be
paid in one installment. If the purchase price is greater than $2,500,000, it
shall be paid in five equal annual installments. If the purchase price is
greater than $500,000 but less than $2,500,000, the purchase price will be paid
in consecutive annual installments of $500,000 until the unpaid balance of the
purchase price is less than $500,000, and a final annual installment shall be
payable thereafter equal to the unpaid balance of the purchase price. The first
installment of the purchase price shall be paid at the Closing (as defined
below), and subsequent annual installments, if any, shall be due on the
successive anniversary dates of the Closing. Interest shall accrue from the date
of the Closing on the balance of the purchase price remaining unpaid from time
to time at the prime rate published in the Midwest edition of THE WALL STREET
JOURNAL on the date of the Closing, and accrued interest shall be payable
together with each annual installment of the purchase price. All or part of the
purchase price may be prepaid without penalty or premium. Notwithstanding the
foregoing or any other provision contained herein, the purchase price for any
Restricted Shares (i) purchased by any Other Stockholders upon the exercise of
any rights under SECTIONS 3 or 4 hereof shall be paid in cash at the Closing (as
defined below), and (ii) shall accelerate and become immediately due and payable
upon a Change in Control.

               (b)  CLOSING.

                    (i)     Except as otherwise provided herein, the Restricted
         Shares shall be purchased and sold in accordance with these provisions
         at the offices of the Corporation or its legal counsel at 10:00 a.m. on
         the date set forth in this SECTION 5 (the "CLOSING").

                                       6
<Page>

                    (ii)    The Closing of any purchase of Restricted Shares by
         the Corporation or the Other Stockholders pursuant to SECTION 4 shall
         take place on the following dates, as applicable:

                            (A)  If the purchase is pursuant to SECTION 4(a)(i),
               SECTION 4(b)(ii) or SECTION 4(b)(iii), the Corporation (or the
               Other Stockholders, if applicable) shall give Executive or its
               representative, if applicable, written notice of the exercise of
               such purchase option and the Closing shall occur on the later of
               (A) the tenth (l0th) day following the Valuation Date and (B)
               the sixtieth (60th) day following delivery of such notice.

                            (B)  If the purchase is pursuant to SECTION 4(b)(i),
               the Closing shall occur on the later of (A) the tenth (10th) day
               following the Valuation Date and (B) the Put Purchase Date, but
               in no event later than forty-five (45) days after the Put
               Purchase Date; PROVIDED, HOWEVER, that the timing of the
               Corporation's payment of the purchase price shall, if applicable,
               be subject to the last paragraph of Section 4(b).

                    (iii)   The Corporation shall give Executive, his Permitted
         Transferees, or his heirs or personal representative, as the case may
         be (the "SELLING STOCKHOLDER"), at least twenty (20) days' prior
         written notice of the time, date and place of the Closing of any
         purchase under SECTION 4(a)(ii).

               (c)  TRANSFER DOCUMENTS. At the Closing, the Selling Stockholder
shall deliver to the Corporation stock certificates duly endorsed for transfer,
or accompanied by duly endorsed stock powers, representing all of Restricted
Shares being sold, free and clear of all claims, liens, or encumbrances,
together with such other documentation as the Corporation's legal counsel may
reasonably require, and the Corporation shall act as agent for the Other
Shareholders with respect to any sale under SECTION 3.

               (d)  FAILURE TO TRANSFER RESTRICTED SHARES. If the Selling
Stockholder fails, for any reason, to tender any certificates representing
Restricted Shares in accordance with SECTION 3, 4 or 5, the Corporation may, at
its option, in addition to all other remedies it may have, send to the Selling
Stockholder the purchase price for such Restricted Shares as is herein
specified. Thereupon, the Corporation shall cancel on its books the certificate
or certificates representing the Restricted Shares to be repurchased and all of
the Selling Stockholder's rights in and to such Restricted Shares shall
terminate. If the Corporation and the Other Stockholders do not repurchase all
of the shares represented by such certificate, the Corporation will issue a new
certificate to the Selling Stockholder representing the Restricted Shares which
were not repurchased by the Corporation and the Other Stockholders.

         6.    ADDITIONAL RESTRICTIONS ON TRANSFER OF RESTRICTED SHARES.

               (a)  LEGEND.  The certificates representing Restricted Shares
will bear the following legend:

         "THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN
         REGISTERED UNDER THE SECURITIES ACT OF 1933, AS

                                        7
<Page>

         AMENDED, AND MAY NOT BE SOLD OR OFFERED FOR SALE IN THE ABSENCE OF A
         REGISTRATION STATEMENT WHICH IS EFFECTIVE UNDER THAT ACT AS TO SUCH
         SECURITIES OR AN OPINION, IN FORM AND SUBSTANCE SATISFACTORY TO THE
         CORPORATION AND GIVEN BY COUNSEL SATISFACTORY TO THE CORPORATION, TO
         THE EFFECT THAT SUCH REGISTRATION IS NOT REQUIRED."

         "THE SECURITIES REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO
         ADDITIONAL RESTRICTIONS ON TRANSFER SET FORTH IN AN AMENDED AND
         RESTATED RESTRICTED STOCK AGREEMENT (THE "AGREEMENT") BETWEEN THE
         CORPORATION AND THE HOLDER HEREOF, DATED AS OF JANUARY 15, 2004, A COPY
         OF WHICH MAY BE OBTAINED AT THE PRINCIPAL EXECUTIVE OFFICE OF THE
         CORPORATION. ANY TRANSFER OR PLEDGE IN CONFLICT WITH, OR IN DEROGATION
         OF, THE AGREEMENT IS VOID AND OF NO LEGAL FORCE, EFFECT OR VALIDITY
         WHATSOEVER."

               (b)  SECURITIES ACT. In addition to any other restriction set
forth herein, no holder of Restricted Shares may sell, transfer, or dispose of
any Restricted Shares (except pursuant to an effective registration statement
under the Securities Act of 1933, as amended, and the rules and regulations
promulgated thereunder (the "SECURITIES ACT")) without first delivering to the
Corporation an opinion of counsel reasonably acceptable in form and substance to
the Corporation that registration under the Securities Act is not required in
connection with such transfer; provided, however, that such requirement may be
waived by the Corporation's Board of Directors in its sole discretion.

         7.    TAX CONSEQUENCES. The Corporation shall not be liable or
responsible in any way for the tax consequences to Executive relating to the
Restricted Shares or the lapse of the restrictions hereunder. Executive agrees
to determine and be responsible for any and all tax consequences to himself
relating to the Restricted Shares. If as a result of this Agreement or
otherwise, the Corporation is obligated to withhold an amount on account of any
tax imposed in connection with the termination of any restrictions or
limitations in respect of Restricted Shares, Executive shall be required to pay
such amount to the Corporation.

         8.    VOTING. Executive shall continue to have the right to vote all of
the Restricted Shares on all matters submitted to holders of Common Stock.

         9.    DISTRIBUTIONS. Executive shall have the right to receive all cash
dividends or other distributions with respect to all of the Restricted Shares.

         10.   NO EMPLOYMENT RIGHTS. No provision of this Agreement shall give
Executive any right to continue in the employ of the Corporation, create any
inference as to the length or term of Executive's employment, affect the right
of the Corporation to terminate Executive's employment, with or without Cause,
or give Executive any right to participate in any employee welfare or benefit
plan or other program of the Corporation.

                                       8
<Page>

         11.   TERMINATION. Upon the consummation of a Qualified IPO, this
Agreement and, particularly, the provisions of SECTIONS 3, 4 and 5 hereof, shall
automatically terminate. At Executive's request, the second legend referenced in
SECTION 6(a) shall be removed from each certificate representing any of the
Restricted Shares upon the consummation of a Qualified IPO. For purposes hereof,
"QUALIFIED IPO" means an underwritten public offering of Common Stock or of
equity securities of a successor to the Corporation pursuant to the Securities
Act with gross proceeds in excess of $20,000,000.

         12.   NO DISCLOSURE RIGHTS. The Corporation shall have no duty or
obligation to affirmatively disclose to Executive or his representatives, and
Executive or his representatives shall have no right to be advised of, any
material information regarding the Corporation at any time prior to, upon or in
connection with the termination of Executive's employment with the Corporation,
either by Executive or by the Corporation, or in connection with the
Corporation's repurchase of Restricted Shares in accordance with the terms of
this Agreement.

         13.   NOTICES. Any notice, consents or other communications required to
be sent or given hereunder by any of the parties shall in every case be in
writing and shall be deemed properly served if (a) delivered personally, (b)
sent by registered or certified mail, in all such cases with first class postage
paid, return receipt requested, (c) delivered by a recognized overnight courier
service, or (d) sent by facsimile transmission (with written or facsimile
confirmation of receipt) to the parties at the addresses or facsimile number, as
the case may be, as set forth below or at such other addresses or facsimile
number as may be furnished in writing pursuant to this SECTION 13.

               To the Corporation or
               the Other Shareholders:   optionsXpress, Inc.
                                         39 S. LaSalle St., Suite 220
                                         Chicago, Illinois 60603
                                         Attention: Chairman of the Board
                                         Facsimile: (312)629-5256

               With a copy to:           Katten Muchin Zavis Rosenman
                                         525 West Monroe Street Suite 1600
                                         Chicago, Illinois 60661-3693
                                         Attention: Brian F. Richards, Esq.
                                         Facsimile: (312)902-1061

               To Executive:             Mr. David Kalt
                                         1424 West Berteau Avenue
                                         Chicago, Illinois 60613
                                         Facsimile: (312)629-5256

               With a copy to:           Vedder, Price, Kaufman & Kammholz, P.C.
                                         222 North LaSalle Street
                                         Chicago, Illinois 60601
                                         Attention: Michael A. Nemeroff, Esq.
                                         Facsimile: (312)609-5005

                                        9
<Page>

Any notice under this Agreement will be deemed to have been given (a) on the
date such notice is personally delivered, (b)three (3) days after the date of
mailing if sent by certified or registered mail, (c) one (1) day after the date
such notice is delivered to the overnight courier service if sent by overnight
courier or (d) if by facsimile transmission, on the date of transmission.

         14.   SEVERABILITY. Whenever possible, each provision of this Agreement
will be interpreted in such a manner as to be effective and valid under
applicable law, but if any provision of this Agreement is held to be invalid,
illegal or unenforceable in any respect under any applicable law or rule in any
jurisdiction, such invalidity, illegality or unenforceability will not affect
any other provision or any other jurisdiction, but this Agreement will be
reformed, construed and enforced in such jurisdiction as if such invalid,
illegal or unenforceable provision had never been contained herein.

         15.   COMPLETE AGREEMENT. This Agreement embodies the complete
agreement and understanding among the parties and supersedes and preempts any
prior understandings, agreements or representations by or among the parties,
written or oral, which may have related to the subject matter hereof in any way.

         16.   REMEDIES. Each of the parties to this Agreement will be entitled
to enforce its rights under this Agreement specifically, to recover damages by
reason of any breach of any provision of this Agreement and to exercise all
other rights existing in its favor. Executive agrees and acknowledges that money
damages will not be an adequate remedy for any breach of the provisions of this
Agreement and that the Corporation shall be entitled to specific performance
and/or injunctive relief in order to enforce or prevent any violations of the
provisions of this Agreement.

         17.   AMENDMENTS AND WAIVERS. Any provision of this Agreement may he
amended or waived only with the prior written consent of the Corporation and
Executive.

         18.   GOVERNING LAW. This Agreement shall be construed and enforced in
accordance with, and all questions concerning the construction, validity,
interpretation and performance of this Agreement shall be governed by, the laws
of the State of Delaware, without giving effect to provisions thereof regarding
conflict of laws.

         19.   WAIVER; CUMULATIVE RIGHTS. The failure or delay of either party
hereto to require performance by the other party of any provision hereof shall
not affect its right to require performance of such provision unless and until
such performance has been waived in writing. Each and every right hereunder is
cumulative and may be exercised in part or in whole from time to time.

         20.   SUCCESSORS AND ASSIGNS. This Agreement shall inure to the benefit
of and be binding upon each successor and assign of the Corporation. All
obligations imposed upon Executive or his representative, and all rights granted
to the Corporation hereunder, shall be binding upon Executive's or his
representative's heirs, legal representatives and successors.

                                       10
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         21.   HEADINGS. The captions set forth in this Agreement are for
convenience only and shall not be considered as part of this Agreement or as in
any way limiting the terms and provisions hereof.

         22.   COUNTERPARTS. This Agreement may be executed on separate
counterparts, each of which is deemed to be an original and all of which taken
together constitute one and the same agreement.

         23.   NO STRICT CONSTRUCTION. The language used in this Agreement will
be deemed to be the language chosen by the parties hereto to express their
mutual intent, and no rule of strict construction will be applied against any
party hereto.

                  [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]

                                       11
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       (SIGNATURE PAGE TO AMENDED AND RESTATED RESTRICTED STOCK AGREEMENT)

         IN WITNESS WHEREOF, the Corporation has caused this Amended and
Restated Restricted Stock Agreement to be duly executed by an officer thereunto
duly authorized, and Executive has hereunto set his hand, all as of the day and
year first above written.

                                   OPTIONSXPRESS, INC., a Delaware corporation

                                   By:    /s/ James Gray
                                         -----------------------------------
                                         James Gray, Chairman of the Board

                                   EXECUTIVE:

                                   /s/ David Kalt
                                   -----------------------------------------
                                   David Kalt

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