<PAGE>
                                                                    Exhibit 10.8


                                SUPPORT AGREEMENT


                  THIS SUPPORT AGREEMENT (the "Agreement") dated as of November
12, 1999, between EChapman.com, Inc., a Maryland corporation ("EChapman"), and
Nathan A. Chapman, Jr. (the "Stockholder").

                  WHEREAS, the Stockholder individually possesses the right to
vote, or direct the voting of, an aggregate of 1,828,115 shares of common stock,
$0.001 par value ("Shares"), of Chapman Insurance Holdings, Inc., a Maryland
corporation ("CIH"), which constitute approximately 91.9% of the outstanding
capital stock of CIH, no other shares of any other class of capital stock of CIH
being issued or outstanding; and

                  WHEREAS, the Stockholder individually possesses the power to
dispose of, or to direct the disposition of, an aggregate of 1,828,115 Shares,
which constitute approximately 91.9% of the outstanding capital stock of CIH;
and

                  WHEREAS, EChapman has entered into an Agreement of Merger
with CIH, dated as of the date hereof (the "Merger Agreement"), pursuant to
which EChapman would acquire CIH and The Chapman Insurance Agency
Incorporated, CIH's wholly-owned subsidiary, through the conversion of each
outstanding Share into shares of common stock of EChapman and cash in lieu of
fractional shares pursuant to a merger of CIH into a subsidiary of EChapman
(the "Merger"); and

                  WHEREAS, as a condition to entering into the Merger Agreement,
EChapman has requested that the Stockholder agree, and the Stockholder has
agreed, to support the Merger.

                  NOW, THEREFORE, to induce EChapman to enter into the Merger
Agreement and in consideration of the mutual covenants and agreements set forth
herein and in the Merger Agreement, and intending to be legally bound hereby,
the parties hereto agree as follows:

                  1. REPRESENTATIONS OF STOCKHOLDER. The Stockholder represents
that:

                     (a) (1) he possesses the sole right to vote, or direct the
voting of, all of the Shares, (2) such number of Shares constitutes all of the
Shares with respect to which the Stockholder possesses the sole right to vote,
or direct the voting of, as the case may be, and (3) he has good and
merchantable title to all of the Shares, free of all restrictions and
encumbrances of every kind and character.

                     (b) (1) he possesses the sole power to dispose of, or
direct the disposition of, the Shares, (2) such number of Shares constitutes all
of the Shares with respect to which the Stockholder possesses or will possess
the sole power to dispose of or direct the


<PAGE>


disposition of, and (3) he has good and merchantable title to all of the Shares
free of all restrictions and encumbrances of any kind or character.

                     (c) he does not own, of record or beneficially, any other
shares of CIH's capital stock. For the purposes of this Agreement, beneficial
ownership has the meaning set forth in Rule 13d-3 of the Securities Exchange Act
of 1934, as amended.

                     (d) he has full right, power and authority to enter into,
deliver and perform this Agreement; this Agreement has been duly executed and
delivered by such stockholder; and this Agreement constitutes the legal, valid
and binding obligation of the Stockholder, and is enforceable in accordance with
its terms.

                  2. COVENANTS OF STOCKHOLDER. The Stockholder covenants as
follows:

                     (a) RESTRICTIONS ON TRANSFER. During the term of this
Agreement, the Stockholder shall not pledge, hypothecate, grant a security
interest in, sell, transfer or otherwise dispose of or encumber any of the
Shares and will not enter into any agreement, arrangement or understanding or
grant a proxy (other than a proxy for the purpose of voting his Shares in
accordance with Subparagraph 2(b) hereof) which would, during the term of this
Agreement (i) restrict, (ii) establish a right of first refusal to, or (iii)
otherwise relate to the transfer or voting of such Shares.

                     (b) MERGER. The Stockholder shall vote the Shares in favor
of the Merger Agreement, and the Merger and the transactions contemplated
thereby. The Stockholder agrees not to vote his Shares in favor of any merger,
consolidation, share exchange or sale of assets or other business combination
involving CIH other than the Merger during the term of this Agreement.

                     (c) ADDITIONAL SHARES. The provisions of subparagraphs (a)
and (b) above shall apply to all Shares currently owned and hereafter acquired,
of record or beneficially, by each of the Stockholder.

                  3. TERMINATION. This Agreement shall terminate upon the
termination of the Merger Agreement.

                  4. GOVERNING LAW. This Agreement shall in all respects be
governed by and construed under the laws of Maryland, all rights and remedies
being governed by such laws, without regard to conflict of law principles.

                  5. BENEFIT OF AGREEMENT. This Agreement shall be binding upon
and inure to the benefit of, and shall be enforceable by, the parties hereto and
their respective personal representatives, successors and assigns, except that
neither party may transfer or assign any of its respective rights or obligations
hereunder without the prior written consent of the other party or, if by
EChapman, in accordance with the Merger Agreement.


                                      -2-
<PAGE>

                  6. COUNTERPARTS. For convenience of the parties hereto, this
Agreement may be executed in several counterparts, each of which shall be deemed
an original, all of which together shall constitute one and the same instrument.

                  IN WITNESS WHEREOF, EChapman and the Stockholder has caused
this Agreement to be duly executed as of the day and year first above written.


                                 ECHAPMAN.COM, INC.


                                 By:/s/ NATHAN A. CHAPMAN, JR.
                                    -----------------------------------
                                     Nathan A. Chapman, Jr., President,
                                     Chief Executive Officer and
                                     Chairman of the Board


                                 STOCKHOLDER

                                 /s/ NATHAN A. CHAPMAN, JR.
                                 --------------------------------------
                                 Nathan A. Chapman, Jr.