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                                                                    Exhibit 10.6

                 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 Ned W. Bennett ("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
have 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

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     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 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

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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.

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               (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 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, (13) 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.

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               (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

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     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 David
     Kalt.

     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").

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               (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 (10th) 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

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     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.

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     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: President
                                       Facsimile: (312)629-5256

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

          To Executive:                Mr. Ned W. Bennett
                                       200 Granada Avenue
                                       El Paso, Texas 79912
                                       Facsimile: (915)585-2239

          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

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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 be 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
<Page>

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

                                    EXECUTIVE:

                                    /s/ Ned W. Bennett
                                    --------------------------------------------
                                    Ned W. Bennett<Page>

                                                                    Exhibit 10.7

                           RESTRICTED STOCK AGREEMENT

     THIS RESTRICTED STOCK AGREEMENT (this "AGREEMENT"), dated as of July 15,
2004, is entered into between optionsXpress Holdings, Inc., a Delaware
corporation (the "CORPORATION"), and David Fisher ("EXECUTIVE"). Terms
capitalized and not otherwise defined herein have the meanings assigned to such
terms in SECTION 4(c) below.

     WHEREAS, as an inducement to Executive's acceptance of the Corporation's
offer of employment, the Corporation promised to grant Executive 8,125 shares
(the "SHARES") of common stock ("COMMON STOCK") of the Corporation, subject to
certain contractual restrictions and other terms as set 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 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 such transfer, (B) in connection with a Change in
     Control, (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, "PERMITTED TRANSFEREE" with respect to
Executive means (i) a transferee receiving Vested Restricted Shares pursuant to
applicable laws of descent

<Page>

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 Stock Purchase and Recapitalization Agreement,
dated as of December 17, 2003, among the Corporation, the purchasers identified
therein (collectively referred to herein as the "INVESTORS") and the
stockholders of the Corporation identified therein.

          (c)  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

                                        2
<Page>

     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 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)  VESTED RESTRICTED SHARES.

               (i)   TERMINATION BY THE CORPORATION FOR CAUSE.

                     (A) If the Corporation terminates Executive's employment
          with the Corporation for Cause (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, for a period of one hundred eighty (180) days
          after the effective date of such termination, to repurchase, in
          accordance with this SECTION 4 AND SECTION 5, all of the Vested
          Restricted Shares

                                        3
<Page>

          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.

                     (B) 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, for a period
          of one hundred eighty (180) days after the effective date of such
          termination, to repurchase all of the Vested Restricted Shares for
          $0.0002 per share in accordance with SECTION 5.

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

                     (A) If, on or prior to the third anniversary of the date of
          this Agreement, (I) 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 6(a)(iii)
          of the Employment Letter (as defined below)), or (II) Executive
          resigns with Good Reason (as defined below), then the Corporation
          shall have the right, but not the obligation, for a period of one
          hundred eighty (180) days after the effective date of such
          termination, to repurchase in accordance with this SECTION 4 AND
          SECTION 5 all or any portion of the Vested Restricted Shares at a
          purchase price equal to the Fair Market Value per share as of the
          effective date of such termination.

                     (B) If Executive resigns without Good Reason, the
          Corporation shall have the right, but not the obligation, for a period
          of one hundred eighty (180) days after the effective date of such
          termination, 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 are insufficient to repurchase the total number of Vested
     Restricted Shares the Corporation desires to repurchase 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 elected to repurchase but which it has not repurchased.

          (b)  OTHER STOCKHOLDER OPTION. If the Corporation does not exercise
its purchase option under SECTION 4(A)(I)(A) or SECTION 4(a)(ii), 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

                                        4
<Page>

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.

          (c)  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 July 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 have 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 (30)-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)  "IPO" shall have the definition given to such term in the
     Employment Letter.

                                        5
<Page>

               (v)   "OTHER STOCKHOLDERS" shall mean, collectively, the
     Investors, G-Bar Limited Partnership, Avrum Gray Delta Trust, 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 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,
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 as follows. If the purchase is pursuant to SECTION 4(a)(i)(A),
     SECTION 4(a)(ii)(A), SECTION 4(a)(ii)(B) or SECTION 4(b), 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
     (10th) day following the Valuation Date and (B) the sixtieth (60th) day
     following delivery of such notice; 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(a).

               (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)(i)(B).

          (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,

                                        6
<Page>

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 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 A RESTRICTED STOCK AGREEMENT (THE
     "AGREEMENT") BETWEEN THE CORPORATION AND THE HOLDER HEREOF, DATED AS OF
     JULY 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 and given by counsel satisfactory 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
<Page>

     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 him 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 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.

     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

                                        8
<Page>

          the Other Shareholders:       optionsXpress Holdings, Inc.
                                        39 S. LaSalle St., Suite 220
                                        Chicago, Illinois  60603
                                        Attention:  Chairman of the Board
                                        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

          To Executive:                 Mr. David Fisher
                                        c/o optionsXpress Holdings, Inc.
                                        39 S. LaSalle St., Suite 220
                                        Chicago, Illinois  60603
                                        Facsimile:  (312) 629-5256

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 (I.E., the
Restricted Shares) 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 be amended
or waived only with the prior written consent of the Corporation and Executive.

                                        9
<Page>

     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.

     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]

                                       10
<Page>

                 (SIGNATURE PAGE TO RESTRICTED STOCK AGREEMENT)

     IN WITNESS WHEREOF, the Corporation has caused this 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 HOLDINGS, INC., a Delaware
                                        corporation

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

                                        EXECUTIVE:

                                        /s/ David Fisher
                                        ----------------------------------------
                                        David Fisher

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