<PAGE>

                                                                    Exhibit 10.5

CONFIDENTIAL
June 5, 2000


Dear Ron:

                  This letter (the "Agreement and Release") confirms your
election to retire and resign from employment with Wit Capital Group, Inc. (the
"Company") effective January 2, 2001. We express our gratitude for your services
during the early stages of the evolution of the Company and wish you happiness
and success in your retirement. Our mutual understanding and agreement with
respect to the transition of your duties as Vice-Chairman, Co-CEO and President
of the Company and the termination of your employment is as follows:

                  1. You hereby confirm that your employment with the Company
and its subsidaries will be terminated effective at the close of business on
January 2, 2001 (your "Termination Date"). Your resignation as President and
Co-CEO of the Company and each of its subsidiaries is effective immediately. You
will continue to serve as Vice-Chairman and a director of the Company until the
October, 2000 regularly scheduled Board of Directors meeting. The Agreement
represents your resignation from the Board effective immediately following the
October Board of Directors meeting, or if that meeting is not held for any
reason, effective on October 30, 2000 and from the Boards of the Company's
subsidiaries, effective immediately.

                   2. You understand and agree that from this date until your
Termination Date, you will cooperate with the Company in efficiently and
effectively transitioning your job duties. During this period, you shall be a
Senior Advisor to the Company. You will report directly to Robert Lessin, the
Chief Executive Officer of the Company or his successor, and you agree to
provide such transitional services as you may be requested to provide, including
continuation of your services as a designated director for such companies as Wit
Capital Europe Group, Inc., Wit Capital Japan, Inc. and enba, plc. After the
Termination Date, you agree to make yourself reasonably available to assist the
Company with regard to any matters that arose during the course of your
employment with the Company about which you have knowledge.

                  3. If you have not revoked this agreement within the time
period set forth in Section 15, your total and final compensation, payments and
benefits from the Company (including payment for accrued vacation, severance,
etc.) shall be as follows (in each case less applicable statutory deductions and
withholdings):
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 2


                           (a) You will receive your regular base salary and
Guaranteed Bonus through your Termination Date, plus reimbursement for expenses
in accordance with Company policy.

                           (b) You will receive a bonus for the year 2000 as if
you had been the Co-CEO for the entire year, applying the same measurements,
objective and subjective, that are utilized for the other Co-CEO, subject to the
provisions of this Section 3.(b). The bonus will be as determined by the
Compensation Committee of the Board of Directors in its sole and absolute
discretion and shall be paid at such time as the bonus payments for the year
2000 are paid to the senior executives of the Company. For purposes of
evaluating your performance as part of the subjective evaluation that the
Compensation Committee uses as one measure of determining the Co-CEO's bonus,
the Compensation Committee shall consider your performance for the first six (6)
months of 2000 to have been your performance for the entire year.

                           (c) You will have the right for ninety (90) days
following the Termination Date to exercise your vested stock options as of the
Termination Date. If you have not revoked this Agreement within the time periods
set forth in Section 15, the Company hereby (i) accelerates the vesting of the
options granted to you on June 5, 1998 that are currently scheduled to vest on
June 30, 2000, September 30, 2000 and December 31, 2000 so that each of those
options is vested as of the next business day following the expiration of the
periods set forth in Section 15 of this Agreement and (ii) accelerates the
vesting of the options granted to you on June 5, 1998 that are currently
scheduled to vest on March 31, 2001, June 30, 2001 and September 30, 2001 so
that each of those options shall now be vested on January 2, 2001. In addition,
if you have not revoked this Agreement within the time periods set forth in
Section 15 of this Agreement, the Restricted Stock Agreement dated as of April
30, 1999 between you and the Company is hereby amended so that the Shares (as
defined in the Restricted Stock Agreement) that are scheduled to vest thereunder
shall be vested on the next business day following the expiration of the periods
set forth in Section 15. In all other respects, the Restricted Stock Agreement
shall continue in effect. Section 1 of the Partial Recourse Note of April 30,
1999 relating to the purchase of the Shares is amended to provide that
Subsections (ii) and (iii) are hereby deleted.

                                    Section 2 of the Partial Recourse Note of
April 30, 1999 is amended to include the following new sentences: "In the event
that the Borrower, whether alone or as an individual proprietor, partner,
officer, director, consultant, agent, employee or stockholder of any company or
other commercial enterprise, directly or indirectly, directly or indirectly
engages in any business activity that competes with the Company or any of its
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 3


subsidiaries, or with any business planned to be engaged in by the Company or
any of its subsidiaries during the term of the Borrower's employment by the
Company, the entire unpaid outstanding principal amount and all accrued and
unpaid interest thereon shall be immediately due and payable, without
presentment, demand, protest or further notice of any kind, all of which are
expressly waived by the Borrower. Notwithstanding anything to the contrary in
this Section 2, the Borrower shall be entitled to make passive investments not
exceeding five percent (5%) as a shareholder and you may continue serving as a
director of companies for which you are currently serving in such capacity and
may in the future serve as a director of other companies that may be deemed to
be in competition with the Company with the prior written consent of the Board
of Directors of the Company." You agree that your option grant of December 20,
1999 for two hundred thousand (200,000) options to purchase shares of the
Company is hereby cancelled.

                           (d) You will continue to actively participate in all
the Company's benefit plans and programs as of your Termination Date at which
time you will cease to be a participant thereunder in accordance with the terms
thereof. You retain your right to benefits you have earned and are entitled to
under specific terms of these plans through your Termination Date, and you may
have conversion privileges under some of these plans. Specific information
concerning these plans and your entitlements thereunder will be forwarded to you
separately.

                           (e) You may continue to be covered under the
Company's group medical insurance program for a period of 18 months from your
Termination Date (or such longer period as may be required by law) or until you
experience a "COBRA" disqualifying event" (such as becoming covered by any other
group health plan), whichever occurs first. This continued coverage shall be
available at your own expense. Specific information on this program, including
the rate structure, will be sent to you separately. Your coverage and cost
levels are governed by and subject to adjustment in accordance with the terms of
the documents governing the program.

                           (f) You will continue to occupy your current office
until the date of your resignation from the Board of Directors of the Company.
The Company will provide you with secretarial assistance from your current
secretary as long as she is employed by the Company as needed until the
Termination Date.

                           (g) The Company will pay for the reasonable moving
expenses for the contents of your New York apartment to your home in Maryland.
As of January 1, 2001, the Company shall be responsible for the lease on your
New York apartment if the lease on the
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 4


apartment has not been cancelled or a sublease has not been entered into with
respect to the remaining six (6) months of the term.

                           (h) As part of this Agreement, you shall be entitled
to retain through the Termination Date and thereafter the IBM laptop PC and Palm
V that you are currently using.

                           (i) Your inability to perform your duties hereunder
due to your death or disability shall not forfeit your rights and entitlement to
the payments and other benefits due under and in accordance with this Section 3.

                  4. Other than as set forth herein, you will not receive any
compensation, payments or benefits of any kind from the Company or Releasees (as
that term is defined below), and you expressly acknowledge and agree that you
are not entitled to and will not receive any additional compensation, payments
or benefits of any kind from the Company or Releasees, and that no
representations or promises have been made to you to the contrary.

                  5. You understand and agree that you are receiving
compensation, payments and/or benefits under this Agreement and Release that are
in excess of those to which you are now or in the future may be entitled from
the Company or Releasees, and that such compensation, payments and benefits are
being provided to you in consideration for your acceptance and execution of, and
in reliance upon your representations in, this Agreement and Release, and you
acknowledge that such consideration is adequate and satisfactory to you.

                  6. In exchange for the compensation, payments, benefits and
other consideration provided to you pursuant to this Agreement and Release, you
agree as follows:

                           (a) You agree to accept the compensation, payments,
benefits and other consideration provided for in this Agreement and Release in
full resolution and satisfaction of, and hereby IRREVOCABLY AND UNCONDITIONALLY
RELEASE, REMISE AND FOREVER DISCHARGE the Company and Releasees from any and all
agreements, promises, rights, liabilities, claims and demands of any kind
whatsoever, in law or equity, whether known or unknown, asserted or unasserted,
fixed or contingent, apparent or concealed, which you, your heirs, executors,
administrators, successors or assigns ever had, now have or hereafter can, shall
or may have for, upon, or by reason of any matter, cause or thing whatsoever
existing, accruing, arising or occurring at any time on or prior to the date you
execute this Agreement and Release, including, without limitation, any and all
rights and claims arising out of or relating to your employment, compensation
and benefits with the Company and/or the termination thereof, and
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 5


any and all contract claims, benefit claims, tort claims, fraud claims, claims
for bonuses, defamation, disparagement and other personal injury claims, claims
under any federal, state or municipal wage payment, discrimination or fair
employment practices law, statute or regulation and claims for costs, expenses
and attorneys' fees with respect thereto, except that the Company's obligations
under this Agreement and Release shall continue in full force and effect in
accordance with their terms. You further agree that this Agreement and Release
shall act as a complete bar to any claim, demand or action of any kind,
whatsoever which could be brought by you against the Company and Releasees. THIS
RELEASE AND WAIVER INCLUDES, WITHOUT LIMITATION, ANY AND ALL RIGHTS AND CLAIMS
UNDER TITLE VII OF THE CIVIL RIGHTS ACT OF 1964, AS AMENDED, THE CIVIL RIGHTS
ACT OF 1991, THE CIVIL RIGHTS ACT OF 1866 (42 U.S.C. SS. 1981), THE EMPLOYEE
RETIREMENT INCOME SECURITY ACT, AS AMENDED, THE AMERICANS WITH DISABILITIES ACT,
THE AGE DISCRIMINATION IN EMPLOYMENT ACT, THE FAIR LABOR STANDARDS ACT, THE
FAMILY AND MEDICAL LEAVE ACT, THE NEW YORK HUMAN RIGHTS LAW, AND ALL OTHER
FEDERAL, STATE OR LOCAL STATUTES, ORDINANCES, REGULATIONS OR CONSTITUTIONAL
PROVISIONS.

                           (b) By signing this Agreement and Release and by
acceptance of the compensation, payments, benefits and other consideration
provided for herein, you WAIVE, RELEASE AND COVENANT NOT TO SUE the Company and
Releasees with respect to any matter relating to or arising out of your
employment, compensation and benefits with the Company and/or the termination
thereof, and you agree that you will not file, charge, claim, sue or permit to
be filed on your behalf any civil action, suit or legal proceeding against the
Company or Releasees seeking personal equitable or mandatory relief for you in
connection with any matter occurring at any time in the past concerning your
employment relationship with the Company or on the basis of any claim arising
out of or relating to your employment, compensation and benefits with the
Company and/or the termination thereof, up to and including the date of this
Agreement and Release, or involving any continuing effects of any acts or
practices which may have arisen or occurred on or prior to the date of this
Agreement and Release. You further agree and covenant that should any person,
organization, or other entity file, charge, claim, sue, or cause or permit to be
filed any civil action, suit or legal proceeding on your behalf against the
Company or Releasees involving any matter occurring at any time in the past, you
will not seek or accept any personal relief in such civil action, suit or legal
proceeding, provided, however, that this waiver, release and covenant not to sue
contained in this paragraph 6(b) shall not prohibit you from enforcing against
the Company your rights under this Agreement and Release. You represent and
affirm (i) that you have not filed any claim or demand for relief
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 6


against the Company or Releasees, (ii) that to the best of your knowledge and
belief, there are no outstanding claims or demands for relief within the meaning
of this paragraph 6(b), and (iii) that in the event any such claim or demand is
or has been filed or comes to your attention you will immediately and without
further notice take all actions within your control necessary to have such claim
or demand withdrawn or dismissed with prejudice.

                           (c) For purposes of this Agreement and Release, the
terms "the Company and Releasees" includes the Company and their past, present
and future direct and indirect parents, subsidiaries, affiliates, divisions,
predecessors, successors, and assigns, and their respective past, present and
future stockholders, officers, directors, representatives, agents and employees,
in their official capacities, and all other related individuals and entities,
jointly and individually, and this Agreement and Release shall inure to the
benefit of and shall be binding and enforceable by all such entities and
individuals.

                           (d) It is expressly understood and agreed that this
Agreement and Release shall act as a complete bar to any claim, demand or action
of any kind whatsoever brought by you or on your behalf against the Company and
Releasees including, without limitation, any claim, demand or action before a
federal, state or municipal court or any arbitration tribunal, except for
claims, demands or actions to enforce this Agreement and Release.

                  7. Nothing contained in this Agreement and Release shall be
deemed to constitute an admission or evidence of any wrongdoing or liability on
the part of the Company or Releasees, nor of any violation of any federal, state
or municipal statute, regulation or principle of common law or equity. The
Company expressly denies any wrongdoing of any kind in regard to your
employment, or your termination.

                  8. As further consideration for the compensation, payments,
benefits and other consideration provided to you pursuant to this Agreement and
Release, you agree as follows:

                           (a) Except as provided in Section 3(h) and this
Section 8(a), you agree that on the Termination Date you will return to the
Company all the Company property which includes, but is not limited to any keys,
credit cards, I.D. cards, laptop computers, etc., and any and all original and
duplicate copies of your work product and of files, calendars, books, records,
notes, notebooks, manuals, computer disks, diskettes and any other magnetic and
other media
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 7


materials you have in your possession or under your control belonging to the
Company or Releasees or containing confidential or proprietary information
concerning the Company or Releasees or their officers, directors, employees,
consultants, customers or operations. You shall be entitled to retain all of
your electronic files (including, without limitation, e-mails, calendars,
contact lists) so long as the Company is provided with copies thereof.

                           (b) You agree that during the course of your
employment with the Company, you have had substantial access to trade secrets,
copyrighted materials, proprietary computer software and programs, and other
confidential and proprietary information and materials of or about the Company
or Releasees or their legal and business affairs, operations, officers,
directors, employees, consultants, vendors or customers (the "Confidential and
Proprietary Information and Materials"). Such Confidential and Proprietary
Information and Materials includes, without limitation, (i) marketing,
promotional, advertising and business plans, studies, data, programs and
strategies; (ii) existing and new or envisioned products; (iii) computer aided
systems, software, strategies, designs, programs and plans; (iv) information and
materials concerning past, present and prospective officers, directors,
employees, consultants, customers, vendors, suppliers and business partners; (v)
information and materials regarding past, present and prospective employment
policies and procedures and employee benefits plans, policies and programs; (vi)
studies and analyses, research and development projects and test data; (vii)
marketing, sales, pricing, costs, and other business and financial data and
projections; and (viii) information and materials developed from the foregoing
information and materials, the disclosure of which to competitors of the Company
or others would cause the Company to suffer substantial and irreparable damage.
You recognize, therefore, that it is in the Company's legitimate business
interest to restrict your disclosure or use of such Confidential and Proprietary
Information and Materials for any purposes other than as agreed to in writing by
the Company and to prohibit any potential appropriation of such Confidential and
Proprietary Information and Materials by you for the benefit of the Company's
competitors or to the detriment of the Company.

                           (c) Unless you shall first secure the Company's
written consent, you shall not directly or indirectly publish, disclose, market
or use, or authorize, advise, hire, counsel or otherwise procure any other
person or entity, directly or indirectly, to publish, disclose, market or use,
any Confidential and Proprietary Information and Materials, including any
Confidential and Proprietary Information and Materials of which you became aware
or informed during your employment with the Company, whether such information is
in your memory or embodied in writing or other form, unless such information
becomes available to the public other than as a result of the disclosure thereof
by you. Such Confidential and Proprietary Information and
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 8


Materials are and shall continue to be the exclusive proprietary property of the
Company and Releasees, whether or not they were disclosed to or developed in
whole or in part by you. Notwithstanding the foregoing, in the event you are
requested pursuant to or required by applicable law or regulation or by legal
process (including, but not limited to, oral questions, interrogatories,
requests for information or documents, subpoena, civil investigative demand or
similar process) to disclose any Confidential and Proprietary Information and
Materials, you must immediately notify the Company of such request or
requirement so that the Company may seek an appropriate protective order or
waive compliance with the provisions of this paragraph 8. You agree to cooperate
with the Company in seeking any such protective order.

                           (d) You will not make any statement or issue any
communication, written or otherwise, that disparages, criticizes or otherwise
reflects adversely or encourages any adverse action against the Company or
Releasees, except if testifying truthfully under oath pursuant to any lawful
court order or subpoena or otherwise responding to or providing disclosures
required by law.

                           (e) You acknowledge and agree that the Company and
Releasees will suffer immediate, substantial damages not readily ascertainable
or compensable in terms of money in the event of the breach of any of your
obligations under this paragraph 8 of this Agreement and Release, and that the
Company and Releasees shall therefore be entitled (without limitation of any
other rights or remedies otherwise available to the Company and Releasees) to
obtain temporary, preliminary and other appropriate injunctive relief from any
court of competent jurisdiction prohibiting the continuance or recurrence of any
such breach.

                  9. This Agreement and Release may not be changed orally, and
no modification, amendment or waiver of any of the provisions contained in this
Agreement and Release, nor any future representation, promise or condition in
connection with the subject matter of this Agreement and Release, shall be
binding upon any party hereto unless made in writing and signed by such party.

                  10. This Agreement and Release shall be subject to and
governed by and interpreted in accordance with the laws of the State of New York
without regard to conflicts of law principles.

                  11. This Agreement and Release shall inure to the benefit of
and shall be binding upon (i) the Company, its successors and assigns, and any
company with which the
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 9


Company may merge or consolidate or to which the Company may sell all or
substantially all its assets, and (ii) you and your executors, administrators,
heirs and legal representatives. You may not sell or otherwise assign your
rights, obligations or benefits under this Agreement and Release and any attempt
to do so shall be void.

                    12. This Agreement and Release, together with the Restricted
Stock Agreement dated as of April 30, 1999 and the Partial Recourse Note dated
April 30, 1999 that are amended in Section 3 hereof, contain the entire
agreement between us and supersedes and terminates any and all previous
agreements between us, whether written or oral, except for (i) the
Indemnification Agreement dated May 17, 1999 between us; (ii) the Restricted
Stock Agreement, Partial Recourse Note and Pledge Agreement dated April 30,
1999; (iii) the outstanding stock option grants dated June 5, 1998; and (iv)
those agreements relating to confidential and proprietary information,
inventions, copyrights and the like which shall remain in force and effect in
accordance with their terms. Specifically, your employment agreement of January
1, 1999 is terminated and your stock option grant of December 20, 1999 is
cancelled. All prior and contemporaneous discussions and negotiations have been
and are merged and integrated into, and are superseded by, this Agreement and
Release. No waiver by either party of any provision or condition of this
Agreement and Release at any time shall be deemed a waiver of such provision or
condition at any prior or subsequent time or of any other provision or condition
at the same or any prior or subsequent time. All defined terms in this Agreement
and Release apply equally to the singular and plural forms thereof.

                  13. The parties agree that this Agreement and Release may be
specifically enforced in court and may be used as evidence in a subsequent
proceeding in which any of the parties allege a breach of this Agreement and
Release. In the event any action, suit or other proceeding is brought to
interpret, enforce or obtain relief from a breach of this Agreement and Release,
the prevailing party shall recover all such party's costs, expenses and
attorneys' fees incurred in each and every such action, suit or other
proceeding, including any and all appeals or petitions therefrom.

                  14. In the event any provision of this Agreement and Release
shall be held to be void, voidable, unlawful or, for any reason, unenforceable,
the remaining portions shall remain in full force and effect. The
unenforceability or invalidity of a provision of this Agreement and Release in
one jurisdiction shall not invalidate or render that provision unenforceable in
any other jurisdiction.
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 10


                  15. BY SIGNING THIS AGREEMENT AND RELEASE, YOU CERTIFY THAT
YOU HAVE READ THE TERMS OF THIS AGREEMENT AND RELEASE, AND THAT YOUR EXECUTION
OF THIS AGREEMENT AND RELEASE SHALL INDICATE THAT THIS AGREEMENT AND RELEASE
CONFORMS TO YOUR UNDERSTANDINGS AND IS ACCEPTABLE TO YOU AS A FINAL AGREEMENT.
YOU FURTHER ACKNOWLEDGES AND AGREES THAT, PURSUANT TO PARAGRAPH 6 ABOVE, BY
SIGNING THIS AGREEMENT AND RELEASE, YOU WAIVE AND RELEASE ANY AND ALL CLAIMS YOU
MAY HAVE OR HAD AGAINST THE COMPANY AND RELEASEES, INCLUDING, WITHOUT
LIMITATION, CLAIMS UNDER THE AGE DISCRIMINATION IN EMPLOYMENT ACT. YOU FURTHER
ACKNOWLEDGE AND AGREE THAT YOU HAVE BEEN ADVISED OF THE OPPORTUNITY TO CONSULT
WITH COUNSEL OF YOUR CHOICE AND THAT YOU HAVE BEEN GIVEN A REASONABLE AND
SUFFICIENT PERIOD OF TIME OF NOT LESS THAN TWENTY-ONE (21) DAYS IN WHICH TO
CONSIDER AND RETURN THIS AGREEMENT AND RELEASE. YOU FURTHER ACKNOWLEDGE AND
AGREE THAT UPON HIS EXECUTION AND RETURN OF THIS AGREEMENT AND RELEASE, YOU WILL
BE PERMITTED TO REVOKE THE AGREEMENT AND RELEASE AT ANY TIME DURING A PERIOD OF
SEVEN (7) CALENDAR DAYS FOLLOWING YOUR EXECUTION HEREOF. TO BE EFFECTIVE, THE
REVOCATION MUST BE IN WRITING AND MUST BE HAND-DELIVERED OR TELECOPIED TO THE
COMPANY WITHIN THE SEVEN (7) DAY PERIOD. THIS AGREEMENT AND RELEASE WILL NOT BE
EFFECTIVE UNTIL THE SEVEN (7) DAY PERIOD HAS EXPIRED. IF THE AGREEMENT AND
RELEASE IS REVOKED WITHIN THE AFOREMENTIONED SEVEN (7) DAY PERIOD, THIS
AGREEMENT AND RELEASE WILL BE OF NO FURTHER FORCE OR EFFECT, AND NEITHER YOU NOR
THE COMPANY WILL HAVE ANY RIGHTS OR OBLIGATIONS HEREUNDER.

                                                     Sincerely,

                                                     Wit Capital Group, Inc.


                                                     By:
                                                        ------------------------

BY SIGNING THIS AGREEMENT AND RELEASE, YOU ACKNOWLEDGE THAT YOU ARE COMPETENT,
THAT YOU HAVE BEEN AFFORDED A TIME PERIOD OF 21 DAYS TO REVIEW AND CONSIDER THIS
AGREEMENT AND RELEASE WITH AN ATTORNEY OF YOUR CHOICE, THAT SUCH TIME PERIOD IS
A
<PAGE>

Mr. Ronald W. Readmond
June 5, 2000
Page 11


REASONABLE AND SUFFICIENT TIME FOR SUCH REVIEW, THAT YOU HAVE READ, UNDERSTAND
AND ACCEPT THIS AGREEMENT AND RELEASE AS FULLY AND FINALLY WAIVING ANY AND ALL
CLAIMS, DEMANDS, DISPUTES AND DIFFERENCES OF ANY KIND WHATSOEVER WHICH YOU MAY
HAVE HAD OR NOW HAVE AGAINST THE COMPANY, THAT NO REPRESENTATIONS, PROMISES OR
INDUCEMENTS HAVE BEEN MADE TO YOU EXCEPT AS SET FORTH IN THIS AGREEMENT AND
RELEASE, AND THAT YOU HAVE SIGNED THIS AGREEMENT AND RELEASE FREELY AND
VOLUNTARILY, INTENDING TO BE LEGALLY BOUND BY ITS TERMS, AND WITH FULL
UNDERSTANDING OF ITS CONSEQUENCES.


__________________________________          Date:__________________
Ronald W. Readmond

I acknowledge that I have read
this Agreement and Release
and that I understand and
voluntarily accept its terms.


WITNESSED BY: ____________________