<Page>

                                                                    EXHIBIT 10.4

                             TAILWIND FINANCIAL INC.

               SECOND AMENDED AND RESTATED SUBSCRIPTION AGREEMENT

     THIS SECOND AMENDED AND RESTATED SUBSCRIPTION AGREEMENT (the "AGREEMENT")
is made as of the 20th day of September, 2006, by and between TAILWIND FINANCIAL
INC., a Delaware corporation (the "COMPANY"), and TFC Holdings Ltd., an Ontario
CORPORATION ("PURCHASER").

     This Agreement amends, restates, supersedes and replaces in its entirety
that certain Subscription Agreement, dated August 29, 2006 ("FIRST AMENDED AND
RESTATED AGREEMENT"), by and between the Company and Purchaser, which amended,
restated, superceded and replaced in its entirety that certain Subscription
Agreement, dated July 12, 2006, by and between the Company and Purchaser and
which First Amended and Restated Agreement is hereby deemed terminated and of no
further force and effect.

     WHEREAS, the Company desires to issue and sell and Purchaser desires to
purchase and acquire Stock (as herein described) on the terms and conditions
hereinafter set forth;

     NOW, THEREFORE, IT IS AGREED between the parties as follows:

     1.   PURCHASE AND SALE OF STOCK. Purchaser hereby agrees to subscribe for
and purchase from the Company, and the Company hereby agrees to issue and sell
to Purchaser an aggregate of 3,125,000 shares of the common stock of the
Company, par value $0.01 per share (the "STOCK") at a purchase price of $0.01
per share on the terms and conditions set forth herein. The closing of the
purchase and sale of the Stock hereunder, including payment for and delivery of
the Stock shall occur at the offices of the Company immediately following the
execution of this Agreement, or at such other time and place as the parties may
mutually agree.

     2.   PAYMENT OF PURCHASE PRICE. The purchase price for the Stock shall be
tendered in full at the appropriate closing by one or a combination of the
following means:

     (a)  wiring of immediately available United States funds to an account for
the benefit of the Company, pursuant to wire instructions provided by the
Company in advance; or

     (b)  by delivery of a cashiers check to the Company of immediately
available United States funds.

     3.   LIMITATIONS ON TRANSFER. Purchaser shall not assign, hypothecate,
donate, encumber or otherwise dispose of any interest in the Stock during the
"ESCROW SHARE PERIOD" (as defined in the securities escrow agreement, dated on
or about the effective date of the Company's initial public offering by and
between the Company and American Stock Transfer & Trust Company (the "SECURITIES
ESCROW AGREEMENT")); except (i) as permitted by Section 4.3 of the Securities
Escrow Agreement and (ii) in compliance with applicable securities laws.

     4.   RESTRICTIVE LEGENDS. All certificates representing the Stock shall
have endorsed thereon legends in substantially the following forms (in addition
to any other legend which may be required by other agreements between the
parties hereto):

          (a)  "THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED. THE SECURITIES

<Page>

MAY NOT BE SOLD, OFFERED FOR SALE, PLEDGED OR HYPOTHECATED IN THE ABSENCE OF AN
EFFECTIVE REGISTRATION STATEMENT AS TO THE SECURITIES UNDER SAID ACT OR AN
OPINION OF COUNSEL SATISFACTORY TO THE COMPANY THAT SUCH REGISTRATION IS NOT
REQUIRED."

          (b)  "THE SECURITIES REPRESENTED BY THIS CERTIFICATE MAY NOT BE
ASSIGNED, HYPOTHECATED, DONATED, ENCUMBERED, SOLD, TRANSFERRED OR OTHERWISE
DISPOSED OF EXCEPT IN ACCORDANCE WITH THAT CERTAIN SECURITIES ESCROW AGREEMENT
DATED AS OF _________, 2006, A COPY OF WHICH IS AVAILABLE FOR INSPECTION AT THE
OFFICES OF THE COMPANY."

          (c)  Any legend required by appropriate blue sky officials.

     5.   INVESTMENT REPRESENTATIONS. In connection with the purchase of the
Stock, Purchaser represents to the Company the following:

          (a)  Purchaser is aware of the Company's business affairs and
financial condition and has acquired sufficient information about the Company to
reach an informed and knowledgeable decision to acquire the Stock. Purchaser is
purchasing the Stock for investment for Purchaser's own account only and not
with a view to, or for resale in connection with, any "distribution" thereof
within the meaning of the Securities Act of 1933, as amended (the "ACT").
Purchaser understands that the Company is a blank check development stage
company recently formed for the purpose of consummating an initial business
combination (an "INITIAL ACQUISITION") and understands that there is no
assurance as to the future performance of the Company and that the Company may
never effectuate an Initial Acquisition.

          (b)  Purchaser understands that the Stock has not been registered
under the Act by reason of a specific exemption therefrom, which exemption
depends upon, among other things, the bona fide nature of Purchaser's investment
intent as expressed herein.

          (c)  Purchaser further acknowledges and understands that the Stock
must be held indefinitely unless the Stock is subsequently registered under the
Act or an exemption from such registration is available. Purchaser understands
that the certificate evidencing the Stock will be imprinted with a legend which
prohibits the transfer of the Stock unless the Stock is registered or such
registration is not required in the opinion of counsel for the Company.

          (d)  Purchaser is familiar with the provisions of Rule 144 under the
Act, as in effect from time to time ("RULE 144"), which, in substance, permit
limited public resale of "restricted securities" acquired, directly or
indirectly, from the issuer thereof (or from an affiliate of such issuer), in a
non-public offering subject to the satisfaction of certain conditions. Unless
the Company registers the Stock under the Act, the Stock may be resold by
Purchaser only in certain limited circumstances subject to the provisions of
Rule 144, which requires, among other things: (i) the availability of certain
public information about the Company and (ii) the resale occurring following the
required holding period under Rule 144 after the Purchaser has purchased, and
made full payment of (within the meaning of Rule 144), the securities to be
sold.

          (e)  Purchaser further understands that at the time Purchaser wishes
to sell the Stock there may be no public market upon which to make such a sale,
and that, even if such a public market then exists, the Company may not be
satisfying the current public information requirements of Rule 144, and that, in
such event, Purchaser would be precluded from selling the Stock under Rule 144
even if the minimum holding period requirement had been satisfied.
Notwithstanding Sections 4(d) and (e) hereof, Purchaser understands that he may
be considered a promoter of the Company and understands that it is

<Page>

the position of the Securities and Exchange Commission (the "SEC") that
promoters or affiliates of a blank check company and their transferees, both
before and after a business combination, would act as an "underwriter" under the
Act when reselling the securities of a blank check company. Accordingly, the SEC
believes that those securities can be resold only through a registered offering
and that Rule 144 would not be available for those resale transactions despite
technical compliance with the requirements of Rule 144.

          (f)  Purchaser represents that Purchaser is an "accredited investor"
as that term is defined in Rule 501 of Regulation D promulgated by the SEC under
the Act.

          (g)  The Purchaser has all necessary corporate power and authority to
enter into this Agreement and to consummate the transactions contemplated
hereby. All corporate action necessary to be taken by the Purchaser to authorize
the execution, delivery and performance of this Agreement and all other
agreements and instruments delivered by the Purchaser in connection with the
transactions contemplated hereby has been duly and validly taken and this
Agreement has been duly executed and delivered by the Purchaser. Subject to the
terms and conditions of this Agreement, this Agreement constitutes the valid,
binding and enforceable obligation of the Purchaser, enforceable in accordance
with its terms, except as enforceability may be limited by (i) applicable
bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer or
similar laws of general application now or hereafter in effect affecting the
rights and remedies of creditors and by general principles of equity (regardless
of whether enforcement is sought in a proceeding at law or in equity); and (ii)
the applicability of the federal and state securities laws and public policy as
to the enforceability of the indemnification provisions of this Agreement. The
purchase by the Purchaser of the Stock does not conflict with the organizational
documents of the Purchaser or with any material contract by which the Purchaser
or its property is bound, or any laws or regulations or decree, ruling or
judgment of any court applicable to the Purchaser or its property. The principal
place of business and executive offices of Purchaser are as set forth on the
signature page hereto.

     6.   COMPANY REPRESENTATIONS AND WARRANTIES. The Company hereby represents
and warrants to the Purchaser that the Company has all necessary corporate power
and authority to enter into this Agreement and to consummate the transactions
contemplated hereby. All corporate action necessary to be taken by the Company
to authorize the execution, delivery and performance of this Agreement and all
other agreements and instruments delivered by the Company in connection with the
transactions contemplated hereby has been duly and validly taken and this
Agreement has been duly executed and delivered by the Company. Subject to the
terms and conditions of this Agreement, this Agreement constitutes the valid,
binding and enforceable obligation of the Company, enforceable in accordance
with its terms, except as enforceability may be limited by (i) applicable
bankruptcy, insolvency, reorganization, moratorium, fraudulent transfer or
similar laws of general application now or hereafter in effect affecting the
rights and remedies of creditors and by general principles of equity (regardless
of whether enforcement is sought in a proceeding at law or in equity); and (ii)
the applicability of the federal and state securities laws and public policy as
to the enforceability of the indemnification provisions of this Agreement. The
sale by the Company of the Stock does not conflict with the certificate of
incorporation or by-laws of the Company or any material contract by which the
Company or its property is bound, or any federal or state laws or regulations or
decree, ruling or judgment of any United States or state court applicable to the
Company or its property.

     7.   INDEMNIFICATION. The Purchaser hereby agrees to indemnify and hold
harmless the Company, its respective officers, directors, stockholders,
employees, agents, and attorneys against any and all losses, claims, demands,
liabilities, and expenses (including reasonable legal or other expenses

<Page>

incurred by each such person in connection with defending or investigating any
such claims or liabilities, whether or not resulting in any liability to such
person or whether incurred by the indemnified party in any action or proceeding
between the indemnitor and indemnified party or between the indemnified party
and any third party) to which any such indemnified party may become subject,
insofar as such losses, claims, demands, liabilities and expenses (a) arise out
of or are based upon any untrue statement or alleged untrue statement of a
material fact made by the Purchaser and contained herein, or (b) arise out of or
are based upon any breach by the Purchaser of any representation, warranty, or
agreement made by the Purchaser contained herein.

     8.   MISCELLANEOUS.

          (a)  NOTICES. All notices required or permitted hereunder shall be in
writing and shall be deemed effectively given: (i) upon personal delivery to the
party to be notified, (ii) when sent by confirmed facsimile if sent during
normal business hours of the recipient, and if not during normal business hours
of the recipient, then on the next business day, (iii) five (5) calendar days
after having been sent by registered or certified mail, return receipt
requested, postage prepaid, or (iv) one (1) business day after deposit with a
nationally recognized overnight courier, specifying next day delivery, with
written verification of receipt. All communications shall be sent to the other
party hereto at such party's address hereinafter set forth on the signature page
hereof, or at such other address as such party may designate by ten (10) days
advance written notice to the other party hereto.

          (b)  SUCCESSORS AND ASSIGNS. This Agreement shall inure to the benefit
of the successors and assigns of the Company and, subject to the restrictions on
transfer herein set forth, be binding upon Purchaser, Purchaser's successors,
and assigns.

          (c)  ATTORNEYS' FEES; SPECIFIC PERFORMANCE. Purchaser shall reimburse
the Company for all costs incurred by the Company in enforcing the performance
of, or protecting its rights under, any part of this Agreement, including
reasonable costs of investigation and attorneys' fees.

          (d)  GOVERNING LAW; VENUE. This Agreement shall be governed by and
construed in accordance with the laws of the State of Delaware without regard to
conflicts of law thereof . The parties agree that any action brought by either
party to interpret or enforce any provision of this Agreement shall be brought
in, and each party agrees to, and does hereby, submit to the jurisdiction and
venue of, the appropriate state or federal court for the district encompassing
the Company's principal place of business.

          (e)  FURTHER EXECUTION. The parties agree to take all such further
action(s) as may reasonably be necessary to carry out and consummate this
Agreement as soon as practicable, and to take whatever steps may be necessary to
obtain any governmental approval in connection with or otherwise qualify the
issuance of the securities that are the subject of this Agreement.

          (f)  INDEPENDENT COUNSEL. Purchaser acknowledges that this Agreement
has been prepared on behalf of the Company by Bingham McCutchen LLP, counsel to
the Company and that Bingham McCutchen LLP does not represent, and is not acting
on behalf of, Purchaser. Purchaser has been provided with an opportunity to
consult with Purchaser's own counsel with respect to this Agreement.

          (g)  ENTIRE AGREEMENT; AMENDMENT. This Agreement constitutes the
entire agreement between the parties with respect to the subject matter hereof
and supersedes and merges all prior agreements or understandings, whether
written or oral. This Agreement may not be amended, modified or revoked, in
whole or in part, except by an agreement in writing signed by each of the
parties hereto.

<Page>

          (h)  SEVERABILITY. If one or more provisions of this Agreement are
held to be unenforceable under applicable law, the parties agree to renegotiate
such provision in good faith. In the event that the parties cannot reach a
mutually agreeable and enforceable replacement for such provision, then (i) such
provision shall be excluded from this Agreement, (ii) the balance of the
Agreement shall be interpreted as if such provision were so excluded and (iii)
the balance of the Agreement shall be enforceable in accordance with its terms.

          (i)  COUNTERPARTS. This Agreement may be executed in two or more
counterparts, each of which shall be deemed an original and all of which
together shall constitute one instrument.

          (j)  SURVIVAL. The representations and warranties contained herein
will survive the delivery of, and the payment for, the Stock.

<Page>

     IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of
the day and year first above written.

                               COMPANY:

                               TAILWIND FINANCIAL INC.


                               By:  /s/ Andrew A. McKay
                                    --------------------------------
                                    Name: Andrew A. McKay

                                    Title: President and Chief Executive Officer

                                    Address:
                                            BCE Place, 181 Bay Street
                                            Suite 4400
                                            Toronto, Ontario, Canada M5J 2T3


                               PURCHASER:

                                    TFC HOLDINGS LTD.

                               By:  /s/ Andrew A. McKay
                                    --------------------------------
                                    Name:  Andrew A. McKay
                                    Title: Chief Executive Officer
                                    Address:
                                            BCE Place, 181 Bay Street
                                            Suite 4400
                                            Toronto, Ontario, Canada M5J 2T3