THESTREET COM
DEF 14A, 2000-05-01
COMPUTER PROCESSING & DATA PREPARATION
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<PAGE>
MAY 30, 2000

                                    SCHEDULE 14A
                                 (RULE 14A-101)
                            SCHEDULE 14A INFORMATION
          Proxy Statement Pursuant to Section 14(a) of the Securities
                              Exchange Act of 1934

<TABLE>
      <S>        <C>
      Filed by the Registrant /X/

      Filed by a Party other than the Registrant / /

      Check the appropriate box:
      / /        Preliminary Proxy Statement
      / /        Confidential, for Use of the Commission Only (as permitted
                 by Rule 14a-6(e)(2))
      /X/        Definitive Proxy Statement
      / /        Definitive Additional Materials
      / /        Soliciting Material Pursuant to Rule 14a-11(c) or Rule
                 14a-12

                                 THESTREET.COM, INC.
      -----------------------------------------------------------------------
                 (Name of Registrant as Specified In Its Charter)
</TABLE>

Payment of Filing Fee (Check the appropriate box):

<TABLE>
<S>        <C>  <C>
/X/        No fee required.
/ /        Fee computed on table below per Exchange Act Rules 14a-6(i)(1)
           and 0-11.
           (1)  Title of each class of securities to which transaction
                applies:
                ------------------------------------------------------------
           (2)  Aggregate number of securities to which transaction applies:
                ------------------------------------------------------------
           (3)  Per unit price or other underlying value of transaction
                computed pursuant to Exchange Act Rule 0-11 (set forth the
                amount on which the filing fee is calculated and state how
                it was determined):
                ------------------------------------------------------------
           (4)  Proposed maximum aggregate value of transaction:
                ------------------------------------------------------------
           (5)  Total fee paid:
                ------------------------------------------------------------

/ /        Fee paid previously with preliminary materials.

           Check box if any part of the fee is offset as provided by
/ /        Exchange Act Rule 0-11(a)(2) and identify the filing for which
           the offsetting fee was paid previously. Identify the previous
           filing by registration statement number, or the form or schedule
           and the date of its filing.

           (1)  Amount Previously Paid:
                ------------------------------------------------------------
           (2)  Form, Schedule or Registration Statement No.:
                ------------------------------------------------------------
           (3)  Filing Party:
                ------------------------------------------------------------
           (4)  Date Filed:
                ------------------------------------------------------------
</TABLE>
<PAGE>
                                 THE STREET.COM
                           14 WALL STREET, 14TH FLOOR
                               NEW YORK, NY 10005

                                          MAY 30, 2000

Dear Stockholder:

    You are cordially invited to attend the Annual Meeting of Stockholders (the
"Meeting") of TheStreet.com, Inc. (the "Company") to be held at the TriBeCa
Grand Hotel, Two Avenue of the Americas, New York, New York 10013, on Wednesday,
July 12, 2000, commencing at 10:00 a.m., New York City time. All stockholders of
record as of May 16, 2000 are entitled to vote at the Meeting. I urge you to be
present in person or represented by proxy at the Meeting.

    The enclosed Notice of Annual Meeting and Proxy Statement fully describe the
business to be transacted at the Meeting, which includes (i) the election of
three directors of the Company, (ii) the approval of an amendment to the
Company's Amended and Restated 1998 Stock Incentive Plan (the "Plan") to
increase the number of shares of common stock available for grant pursuant to
awards under the Plan from 4,400,000 to 6,900,000 shares, and (iii) the
ratification of the appointment of Arthur Andersen LLP as the Company's
independent certified public accountants for the fiscal year ending
December 31, 2000.

    The Company's Board of Directors believes that increasing the number of
shares available under the Plan is in the best interests of the Company and its
stockholders because it would permit the Company to continue to award
stock-based compensation to attract and retain qualified employees.

    The Company's Board of Directors believes that a favorable vote on each of
the matters to be considered at the Meeting is in the best interests of the
Company and its stockholders and unanimously recommends a vote "FOR" each such
matter. Accordingly, we urge you to review the accompanying material carefully
and to return the enclosed proxy promptly.

    Directors and officers of the Company will be present to help host the
Meeting and to respond to any questions that our stockholders may have. I hope
you will be able to attend. Even if you expect to attend the Meeting, please
sign, date and return the enclosed proxy card without delay. If you attend the
Meeting, you may vote in person even if you have previously mailed a proxy.

                                          Sincerely,
                                          /s/ Fred Wilson
                               -------------------------------------------------
                                          Fred Wilson
                                          Chairman of the Board

                                       i
<PAGE>
                                 THE STREET.COM
                           14 WALL STREET, 14TH FLOOR
                               NEW YORK, NY 10005

                    NOTICE OF ANNUAL MEETING OF STOCKHOLDERS
                            TO BE HELD JULY 12, 2000

    NOTICE IS HEREBY GIVEN that the Annual Meeting of Stockholders (the
"Meeting") of TheStreet.com, Inc. (the "Company") will be held at the TriBeCa
Grand Hotel, Two Avenue of the Americas, New York, New York 10013, on Wednesday,
July 12, 2000, commencing at 10:00 a.m., New York City time. A proxy card and a
Proxy Statement for the Meeting are enclosed.

   The Meeting is for the purpose of considering and acting upon:

1.  The election of three Class I directors for three-year terms expiring at the
    Company's Annual Meeting of Stockholders in 2003;

2.  A proposal to amend the Company's Amended and Restated 1998 Stock Incentive
    Plan (the "Plan") to increase the number of shares of Common Stock available
    for grant pursuant to awards under the Plan from 4,400,00 shares to
    6,900,000 shares;

3.  The ratification of the appointment of Arthur Andersen LLP as the Company's
    independent certified public accountants for the fiscal year ending
    December 31, 2000; and

4.  Such other matters as may properly come before the Meeting or any
    adjournment or postponement thereof.

    The close of business on May 16, 2000 has been fixed as the record date for
determining stockholders entitled to notice of and to vote at the Meeting or any
adjournment or postponement thereof. For a period of at least 10 days prior to
the Meeting, a complete list of stockholders entitled to vote at the Meeting
shall be open to examination by any stockholder during ordinary business hours
at the offices of the Company at 14 Wall Street, 14(th) Floor, New York, NY
10005.

    Information concerning the matters to be acted upon at the Meeting is set
forth in the accompanying Proxy Statement.

    YOUR VOTE IS IMPORTANT. STOCKHOLDERS WHO DO NOT EXPECT TO BE PRESENT AT THE
MEETING IN PERSON ARE URGED TO COMPLETE, DATE, SIGN AND RETURN THE ENCLOSED
PROXY CARD IN THE ACCOMPANYING ENVELOPE, WHICH REQUIRES NO POSTAGE IF MAILED IN
THE UNITED STATES.

                                          By Order of the Board of Directors
                                          /s/ Jordan Goldstein
                               -------------------------------------------------
                                          Jordan Goldstein
                                          Secretary

New York, New York
May 30, 2000

                                       ii
<PAGE>
                                PROXY STATEMENT
                                      FOR
                         ANNUAL MEETING OF STOCKHOLDERS
                            TO BE HELD JULY 12, 2000
                            ------------------------

                       SOLICITATION AND VOTING OF PROXIES

    This Proxy Statement is being first mailed on or about May 30, 2000 to
stockholders of TheStreet.com, Inc. (the "Company or The Street.com") at the
direction of the Board of Directors of the Company (the "Board of Directors") to
solicit proxies in connection with the 2000 Annual Meeting of Stockholders (the
"Meeting"). The Meeting will be held at the TriBeca Grand Hotel, Two Avenue of
the Americas, New York, New York 10013, on Wednesday, July 12, 2000, commencing
at 10:00 a.m., New York City time, or at such other time and place to which the
Meeting may be adjourned or postponed.

    All shares represented by valid proxies at the Meeting, unless the
stockholder otherwise specifies, will be voted (i) FOR the election of the three
persons named under "Proposal I--Election of Directors" as nominees for election
as Class I directors of the Company for three-year terms expiring at the
Company's Annual Meeting of Stockholders in 2003, (ii) FOR the proposal to amend
the Company's Amended and Restated 1998 Stock Incentive Plan (the "Plan") to
increase the number of shares of Common Stock available for grant pursuant to
awards under the Plan from 4,400,000 to 6,900,000 shares, (iii) FOR the
ratification of the appointment of Arthur Andersen LLP as independent certified
accountants of the Company for the year ending December 31, 2000, and (iv) at
the discretion of the proxy holders, with regard to any matter not known to the
Board of Directors on the date of mailing this Proxy Statement that may properly
come before the Meeting or any adjournment or postponement thereof. Where a
stockholder has appropriately specified how a proxy is to be voted, it will be
voted accordingly.

    Any person giving a proxy pursuant to this solicitation has the power to
revoke it at any time before it is voted. It may be revoked by filing with the
Secretary of the Company at the Company's principal executive office, 14 Wall
Street, 14(th) Floor, New York, New York 10005, a written notice of revocation
or a duly executed proxy bearing a later date, or it may be revoked by attending
the meeting and voting in person. Attendance at the meeting will not, by itself,
revoke a proxy.

                       RECORD DATE AND VOTING SECURITIES

    The close of business on May 16, 2000 is the record date (the "Record Date")
for determining the stockholders entitled to notice of and to vote at the
Meeting. As of April 28, 2000, the Company had issued and outstanding
approximately 25,366,313 shares of Common Stock held by approximately 292
holders of record. The Common Stock constitutes the only outstanding class of
voting securities of the Company entitled to be voted at the Meeting.

                               QUORUM AND VOTING

    The presence at the Meeting, in person or by proxy relating to any matter,
of the holders of a majority of the outstanding shares of Common Stock is
necessary to constitute a quorum. For purposes of the quorum and the discussion
below regarding the vote necessary to take stockholder action, stockholders of
record who are present at the Meeting in person or by proxy and who abstain,
including brokers holding customers' shares of record who cause abstentions to
be recorded at the Meeting, are considered stockholders who are present and
entitled to vote at the Meeting, and thus, shares of Common Stock held by such
stockholders will count toward the attainment of a quorum. If a quorum should
not be present, the Meeting may be adjourned from time to time until a quorum is

                                       1
<PAGE>
obtained. Each share of Common Stock is entitled to one vote with respect to
each proposal to be voted on at the Meeting. Cumulative voting is not permitted
with respect to the election of directors.

    The accompanying proxy card is designed to permit each holder of Common
Stock as of the close of business on the Record Date to vote on each of the
matters to be considered at the Meeting. A stockholder is permitted to vote in
favor of, or to withhold authority to vote for, any or all nominees for election
to the Board of Directors, to vote in favor of or against or to abstain from
voting with respect to the proposal to amend the Company's Amended and Restated
1998 Stock Incentive Plan and to vote in favor of or against or to abstain from
voting with respect to the proposal to ratify the appointment of Arthur Andersen
LLP as the Company's independent certified public accountants for the fiscal
year ending December 31, 2000.

    Brokers holding shares of record for customers generally are not entitled to
vote on certain matters unless they receive voting instructions from their
customers. As used herein, "uninstructed shares" means shares held by a broker
who has not received instructions from its customers on such matters, if the
broker has so notified the Company on a proxy form in accordance with industry
practice or has otherwise advised the Company that it lacks voting authority. As
used herein, "broker non-votes" means the votes that could have been cast on the
matter in question by brokers with respect to uninstructed shares if the brokers
had received their customers' instructions. Although there are no controlling
precedents under Delaware law regarding the treatment of broker non-votes in
certain circumstances, the Company intends to treat broker non-votes in the
manner described in the next two paragraphs.

    Under Delaware law, directors are elected by a plurality of the outstanding
shares of Common Stock, and thus, the three nominees for election as Class I
directors who receive the most votes cast will be elected. Instructions
withholding authority and broker non-votes will not be taken into account in
determining the outcome of the election of directors.

    Approval of the proposal to amend the Plan requires the affirmative vote of
holders of a majority of shares present at the Meeting, provided a quorum is
present.

    Stockholder ratification of the selection of Arthur Andersen LLP as the
Company's independent auditors is not required by the Company's Bylaws or
otherwise. However, the Board of Directors is submitting the selection of Arthur
Andersen LLP to the stockholders for ratification as a matter of good corporate
practice. If the stockholders fail to ratify the selection, the Audit Committee
and the Board of Directors will reconsider whether or not to retain that firm.
Even if the selection is ratified, the Audit Committee and the Board of
Directors in their discretion may direct the appointment of different
independent auditors at any time during the year if they determine that such a
change would be in the best interests of the Company and its stockholders.
Approval of the proposal to ratify the selection of Arthur Andersen LLP as the
Company's independent auditors requires the affirmative vote of holders of a
majority of shares present at the Meeting, provided a quorum is present.

                                       2
<PAGE>
                                   PROPOSAL I
                             ELECTION OF DIRECTORS

    In accordance with our Certificate of Incorporation, our Board of Directors
has been divided into three classes, denominated Class I, Class II and
Class III, with members of each class holding office for staggered three-year
terms. At each annual meeting of our stockholders, the successors to the
directors whose terms expire are elected to serve from the time of their
election and qualification until the third annual meeting of stockholders
following their election until a successor has been duly elected and qualified.

NOMINEES FOR DIRECTOR

    Each of Michael Golden, James J. Cramer and Martin Peretz has been nominated
for election at the Meeting to serve as a director for a three-year term
expiring at our annual meeting of stockholders in 2003 or until his respective
successor has been duly elected and qualified. It is intended that the persons
named in the proxy will vote for the election of each of the three nominees.
Each of the nominees has indicated his willingness to continue to serve as a
member of the Board of Directors if elected; however, in case any nominee should
become unavailable for election to the Board of Directors for any reason not
presently known or contemplated, the proxy holders will have discretionary
authority in that instance to vote for a substitute nominee.

    The nominees for election at the Meeting as Class I directors are as
follows:

    MICHAEL GOLDEN, age 50. Mr. Golden has served as a director of
TheStreet.com. since March 1999. Mr. Golden has worked for The New York Times
Company since 1984. Since October 1997, he has served as its vice chairman and
senior vice president. From January 1996 to October 1997, he was the New York
Times' vice president for operations development. From October 1994 to
January 1996, Mr. Golden was the executive vice president and publisher of
Tennis Magazine, a New York Times publication. From September 1991 to
October 1994, he was the executive vice president and general manager of the New
York Times' women's publishing division.

    JAMES J. CRAMER, age 45. Mr. Cramer is a co-founder of and outside
contributor to TheStreet.com. Mr. Cramer has served as a director of
TheStreet.com since May 1998, and served as co-chairman from June 1996 to
December 1998. Mr. Cramer founded and has served as president and a director of
Cramer, Berkowitz & Co., a hedge fund, since its inception in 1987.

    MARTIN PERETZ, age 60. Dr. Peretz is a co-founder of TheStreet.com.
Dr. Peretz has served as a director of TheStreet.com since May 1998. He served
as co-chairman of TheStreet.com from June 1996 to December 1998. Since 1974,
Dr. Peretz has served as the editor-in-chief and chairman of The New Republic.
He has been a member of the faculty of Harvard University since 1966.
Dr. Peretz also serves as a director of 11 mutual funds managed by the
Dreyfus-Mellon Bank Group, and as chairman of the board of The Electronic
Newstand, Inc., a web site specializing in the sale of magazine subscriptions,
and of the Digital Learning Group, a web-based textbook publisher.

CURRENT DIRECTORS

    The current Class II directors of the Company, who are not standing for re-
election at the Meeting and whose terms will expire at our annual meeting of
stockholders in 2001, are as follows:

    JERRY COLONNA, age 36. Mr. Colonna has served as a director of TheStreet.com
since May 1998. In 1996, Mr. Colonna co-founded Flatiron Partners, an
Internet-focused, early-stage venture capital firm, and has served as a managing
partner since its inception. In February 1995, Mr. Colonna joined CMG@Ventures,
an Internet-focused venture capital firm, as a founding partner. Prior to
joining CMG@Ventures, Mr. Colonna worked for nearly 10 years at CMP
Publications, a technology publishing firm. Mr. Colonna also serves as a
director of iXL, Inc.

                                       3
<PAGE>
    EDWARD F. GLASSMEYER, age 58. Mr. Glassmeyer has served as a director of
TheStreet.com since December 1998. Mr. Glassmeyer co-founded Oak Investment
Partners, a venture capital firm with $1.6 billion of committed capital, in
November 1978. Mr. Glassmeyer serves as a director of Mobius Management
Systems, Inc., a software infrastructure provider for Internet-based bill
presentment and payment and is a director of several privately held Oak
portfolio companies in the information technology sector.

    DAVE KANSAS, age 33. Mr. Kansas has served as a director of TheStreet.com
since May 1998. In addition, Mr. Kansas has served as editor-in-chief of
TheStreet.com since April 1997 and as Executive Vice President, Chief Strategic
Officer, since March 2000. He served as our executive editor from
September 1996 to April 1997. From October 1992 to September 1996, Mr. Kansas
held a variety of positions at The Wall Street Journal, most recently as a
financial markets reporter.

    The current Class III directors of the Company, who are not standing for
re-election at the Meeting and whose terms will expire at our annual meeting of
stockholders in 2002, are as follows:

    THOMAS J. CLARKE, JR., age 43. Mr. Clarke joined TheStreet.com in
October 1999 as president and chief operating officer and was appointed chief
executive officer and made a director of the Company in November 1999. From 1984
through 1998, Mr. Clarke served in several capacities at Technimetrics Inc. (now
known as Thomson Financial Investor Relations), most recently as chief
executive. During his tenure, he significantly enhanced the value of the
company, culminating in its sale to Thomson Corp. in 1998. Mr. Clarke is a
business information adviser for Plum Holdings L.P., a venture capital fund
based in Philadelphia that focuses on early-stage media companies.

    FRED WILSON, age 38. Mr. Wilson has served as a director of TheStreet.com
since May 1998 and as Chairman of our Board of Directors since November 1999. In
1996, Mr. Wilson co-founded Flatiron Partners, an Internet-focused, early-stage
venture capital firm, and has served as a managing partner since its inception.
Prior to Flatiron Partners, Mr. Wilson worked at Euclid Partners, an early stage
venture capital firm, for 10 years where he served as general partner from 1991
to 1996.

    LINDA SRERE, age 44. Ms. Srere has served as a director of the TheStreet.com
since July 1999. Ms. Srere, who has been vice chairman and chief client officer
of Young & Rubicam Inc. ("Y&R"), a diversified global marketing and
communications company, since September 1998, has worked for Y&R since
September 1994, when she first joined the company as executive vice president
and director of business development. Ms. Srere became group managing director
in 1996, where she was responsible for directing Y&R's Advertising global new
business efforts, and in 1997, was named chief executive officer of Y&R's New
York office, becoming the first female CEO in the Company's 75-year history.

    THE BOARD OF DIRECTORS RECOMMENDS THAT STOCKHOLDERS VOTE FOR EACH NAMED
NOMINEE.

BOARD OF DIRECTORS AND COMMITTEES

    GENERAL.  The Company's business is managed under the direction of the Board
of Directors. The Board of Directors meets on a regularly scheduled basis during
the year to review significant developments affecting the Company and to act on
matters requiring Board of Directors approval of the Board of Directors. It also
holds special meetings when an important matter requires action of the Board of
Directors between scheduled meetings. The Board of Directors met or acted by
written consent nine times during the year ended December 31, 1999. During 1999,
each member of the Board of Directors participated in at least 75% of all board
and applicable committee meetings held during the period for which he or she was
a director.

    The Board of Directors has established an Audit Committee and a Compensation
Committee (the "Compensation Committee") to devote attention to specific
subjects and to assist the Board of Directors in the discharge of its
responsibilities. The functions of those committees, their current members and
the number of meetings held during 1999 are set forth below.

                                       4
<PAGE>
    AUDIT COMMITTEE.  The Audit Committee reviews the Company's internal
accounting procedures and considers and reports to the Board Of Directors with
respect to other auditing and accounting matters, including the selection of the
Company's independent auditors, the scope of annual audits, fees to be paid to
the Company's independent auditors and the performance of the Company's
independent auditors. The Audit Committee currently consists of Mr. Glassmeyer
and Mr. Wilson. The Audit Committee met twice during 1999.

    COMPENSATION COMMITTEE.  The Compensation Committee reviews and recommends
to the Board of Directors the salaries, benefits and stock option grants of all
employees, consultants, directors and other individuals compensated by the
Company. The Compensation Committee also administers the Company's stock option
and other employee benefits plans. The Compensation Committee currently consists
of Mr. Glassmeyer and Mr. Colonna. The Compensation Committee met six times
during 1999.

    OTHER.  The Company does not have a nominating committee. The functions
customarily attributable to such a committee are performed by the Board of
Directors as a whole.

COMPENSATION COMMITTEE INTERLOCKS AND INSIDER PARTICIPATION

    The Compensation Committee makes all compensation decisions. Prior to the
formation of the Compensation Committee in June 1998, the Company's Board of
Directors made decisions relating to compensation of the Company's executive
officers. None of the Company's executive officers serves as a member of the
Board Of Directors or compensation committee of any entity that has one or more
of its executive officers serving as a member of the Company's Board of
Directors or Compensation Committee. The Company's Compensation Committee
currently consists of Mr. Colonna and Mr. Glassmeyer, neither of whom has ever
been an officer or employee of the Company, Mr. Cramer served as a member of the
Compensation Committee from June 1998 to February 1999, when Mr. Glassmeyer was
appointed to the Compensation Committee. During his tenure on the Compensation
Committee, Mr. Cramer, an outside contributor to the Company, participated in
all decisions relating to compensation of the Company's executive officers, but
was excluded from discussions by the Board of Directors regarding his own
compensation.

COMPENSATION OF DIRECTORS

    In 1999, one of our directors, Linda Srere, received cash compensation in
the amount of $2,500 per fiscal quarter for an aggregate of $5,000 for serving
on the Board of Directors. All directors are reimbursed for reasonable travel
expenses incurred in connection with attending Board of Directors and committee
meetings. In addition, in June of 1999, each of our non-employee directors were
granted options to purchase 7,500 shares of the Company's Common Stock. The
exercise price of these options is $25.81 per share, which was the fair market
value of the Common Stock on the date of grant. These options, which have a term
of five years, become exercisable in their entirety on May 11, 2000, the first
anniversary of the Company's initial public offering. Ms. Srere, who became a
director on July 20, 1999, received options to purchase 15,000 of Common Stock
on that date, at an exercise price of $33.94 per share.

    See "Certain Relationships and Related Transactions" for a discussion of
certain agreements between the Company and certain directors of the Company.

                                  PROPOSAL II
                      PROPOSED AMENDMENT TO THE COMPANY'S
                 AMENDED AND RESTATED 1998 STOCK INCENTIVE PLAN

    On May 6, 1998, the stockholders of the Company approved the adoption of the
Company's 1998 Stock Incentive Plan, which was amended and restated on
November 1, 1999. On November 5, 1999, the Company filed a registration
statement on Form S-8 to register the shares of Common Stock that

                                       5
<PAGE>
had then been issued pursuant to option awards made under the Plan as well as
the shares of Common Stock that were then available for grant pursuant to awards
under the Plan. Since then, of the 4,400,000 shares of Common Stock authorized
for issuance under the Plan, 4,006,373 shares have been issued upon the exercise
of options, or are reserved for issuance with respect to future awards. In order
to support the Company's long-term incentive compensation programs and to
attract and retain employees, consultants and directors, additional shares are
required. Accordingly, the Board of Directors has approved and recommends to
stockholders the reservation of an additional 2,500,000 shares of Common Stock
for issuance under the Plan.

    The following is a description of the material terms of the Plan, and as
such is qualified by the actual terms of the Plan, the full text of which, as
proposed to be amended, is set forth in Exhibit A attached hereto. In
Exhibit A, the materials that would be deleted from the Plan pursuant to the
proposed amendment are stricken through, and the material that would be added by
such amendment are double underlined. If the amendment is not approved by the
stockholders, the Plan will continue in effect under the present terms. The Plan
is administered by the Compensation Committee. Employees, consultants and
directors of the Company and its related entities are eligible to participate in
the Plan, with the Compensation Committee having the discretion to make all
determinations with respect to the Plan's administration. The Plan may be
amended by the Board of Directors, with stockholder approval where necessary to
satisfy regulatory requirements.

OPTIONS

    Options granted under the Plan will either be incentive stock options, as
defined under Section 422 of the Code, or nonstatutory stock options. The
purchase price of an option will be determined in the discretion of the
Compensation Committee. Options will be exercisable at such times and pursuant
to such conditions as are established by the Compensation Committee. Payment of
the purchase price will be made using such methods as the Compensation Committee
may determine. Following the termination of an optionee's employment with the
Company or a related company, the option will be exercisable to the extent
determined by the Compensation Committee.

RESTRICTED STOCK AWARDS

    Each restricted stock award will specify the number of shares of restricted
stock to be awarded, the price, if any, to be paid by the recipient of the
restricted stock and the date or dates on which, or the conditions upon the
satisfaction of which, the restricted stock will vest. The grant and/or the
vesting of restricted stock may be conditioned upon the completion of a
specified period of service, upon the attainment of specified performance
objectives or upon such other criteria as the Compensation Committee may
determine. The Compensation Committee may provide that the employee will have
the right to vote or receive dividends on restricted stock. Unless the
Compensation Committee provides otherwise, stock received as a dividend on, or
in connection with a stock split of, restricted stock will be subject to the
same restrictions as the restricted stock.

TAX OFFSET PAYMENTS

    The Compensation Committee may provide for a tax offset payment by the
Company to an employee with respect to one or more awards granted under the
Plan. The tax offset payment will be in an amount specified by the Compensation
Committee, which will not exceed the amount necessary to pay the federal, state,
local and other taxes payable with respect to the applicable award and the
receipt of the tax offset payment, assuming that the employee is taxed at the
maximum tax rate applicable to such income. The tax offset payment will be paid
solely in cash.

                                       6
<PAGE>
NEW PLAN BENEFITS

    Since Awards under the Plan are made in the discretion of the Compensation
Committee, neither the awards that will be made in 2000 nor the awards that
would have been made in 1999 had the amendment been in effect are reasonably
ascertainable.

FEDERAL INCOME TAX TREATMENT

    The following discussion of certain relevant income tax effects applicable
to options and restricted stock granted under the Plan is a brief summary only,
and reference is made to the Code and the regulations and interpretations issued
thereunder for a complete statement of all relevant federal tax consequences.
This summary is not intended to be exhaustive and does not describe state, local
or foreign tax consequences.

    A participant generally will not be taxed upon the grant of a nonstatutory
stock option. Rather, at the time of exercise of such option, the optionee will
recognize ordinary income for federal income tax purposes in an amount equal to
the excess of the fair market value of the shares purchased over the option
price. The Company will generally be entitled to a tax deduction at such time
and in the same amount that the optionee recognizes ordinary income.

    An optionee will not be in receipt of taxable income upon the grant or
timely exercise of an incentive stock option. Exercise of an incentive stock
option will be timely if made during its term and if the optionee remains an
employee of the Company or a subsidiary at all times during the period beginning
on the date of grant of the option and ending on the date three months before
the date of exercise (or one year before the date of exercise in the case of a
disabled optionee). The tax consequences of an untimely exercise of an incentive
stock option will be determined in accordance with the rules applicable to
nonstatutory stock options. The Company is not entitled to any tax deduction in
connection with the grant or exercise of an incentive stock option. However, if
the optionee disposes of stock within the holding periods described above, the
Company may be entitled to a tax deduction for the amount of ordinary income, if
any, realized by the optionee.

    An awardee generally will not be taxed upon the grant of a restricted stock
award, but rather will recognize ordinary income in an amount equal to the fair
market value of the Company's common stock at the time the shares are no longer
subject to a substantial risk of forfeiture. The Company will be entitled to a
deduction at the time when, and in the amount that, the awardee recognizes
ordinary income.

    On April 28, 2000, the closing price of the Company's stock as reported on
the Nasdaq National Market was $6.3125 per share.

    THE BOARD OF DIRECTORS RECOMMENDS THAT STOCKHOLDERS VOTE FOR THE PROPOSED
AMENDMENT TO THE PLAN.

                                  PROPOSAL III
                              INDEPENDENT AUDITORS

    The Board of Directors has selected Arthur Andersen LLP as independent
auditors to examine the Company's accounts for the fiscal year ending
December 31, 2000 and has further directed that management submit the selection
of independent auditors for ratification by the stockholders at the Meeting.
Representatives of Arthur Andersen LLP are expected to be present at the
Meeting, will have the opportunity to make a statement if they desire to do so
and will be available to respond to appropriate questions.

    THE BOARD OF DIRECTORS RECOMMENDS THAT STOCKHOLDERS VOTE FOR THE PROPOSED
RATIFICATION OF ARTHUR ANDERSEN LLP AS THE COMPANY'S INDEPENDENT AUDITORS.

                                       7
<PAGE>
                             EXECUTIVE COMPENSATION

SUMMARY COMPENSATION TABLE

    The following table sets forth the compensation earned for all services
rendered to the Company in all capacities during 1999 by (i) the two individuals
who served as our chief executive officer, (ii) our three most highly
compensated executive officers, other than our chief executive officers, who
earned more than $100,000 in 1999 and who were serving as executive officers at
the end of 1999, and (iii) one individual, Mr. Simon Clark, who ceased to be an
executive officer of the Company in February 1999 (collectively, the "Named
Executive Officers"). As of March 2000, Mr. Michael Zuckert ceased to be an
executive officer of the Company and as of April 2000, Mr. Kothari ceased to be
an executive officer of the Company.

<TABLE>
<CAPTION>
                                                                                          LONG-TERM
                                                                  ANNUAL                COMPENSATION
                                                               COMPENSATION                AWARDS
                                                            -------------------   -------------------------
                                                                                                 SECURITIES
                                                  FISCAL                          OTHER ANNUAL   UNDERLYING
NAME AND PRINCIPAL POSITION                        YEAR      SALARY     BONUS     COMPENSATION   OPTIONS(#)
- ---------------------------                      --------   --------   --------   ------------   ----------
<S>                                              <C>        <C>        <C>        <C>            <C>
Kevin W. English...............................    1999     $372,808   $110,000      $56,632(2)   345,350
  Chairman of the Board,                           1998     $ 71,791   $ 25,000                   521,316
  Chief Executive Officer and President(1)

Thomas J. Clarke...............................    1999     $ 67,250   $ 25,000                   500,000
  Chief Executive Officer and Director(3)          1998           --         --                        --

Dave Kansas....................................    1999     $193,000   $ 40,500                    50,000
  Editor-in-Chief and Director                     1998     $130,000   $ 78,769                   105,758

Paul Kothari...................................    1999     $222,423   $ 40,000                   133,333
  Chief Financial Officer and Vice President(5)    1998           --         --                        --

Michael Zuckert................................    1999     $204,875   $ 40,000                   133,333
  Vice President and General Counsel(6)            1998           --         --                        --

Simon Clark....................................    1999     $111,667   $ 10,000                    16,666
  Chief Financial Officer and                      1998     $150,000   $ 25,944                    30,303
  Vice President--Operations(7)
</TABLE>

- ------------------------

(1) Mr. English's employment with TheStreet.com ended in November 1999.

(2) Mr. English received a total of $56,632 in compensation not properly
    categorized as salary or bonus. This figure is primarily comprised of
    $43,000 for the use of a Company apartment from January through
    October 1999 at a fair market rental value of $4,300 per month.

(3) Mr. Clarke joined TheStreet.com in October 1999 as President and Chief
    Operating Officer and was appointed Chief Executive Officer and made a
    director of the Company in November 1999.

(4) Mr. Clark served as our chief financial officer and vice
    president--operations until February 1999, when he became vice president and
    general manager--international markets of TheStreet.com. Mr. Clark's
    employment with TheStreet.com ended in August 1999.

(5) Mr. Kothari joined TheStreet.com in February 1999 as Chief Financial
    Officer. His employment with TheStreet.com ended at the end of April 2000.

(6) Mr. Zuckert joined TheStreet.com in February 1999 as Vice President and
    General Counsel. His employment with TheStreet.com ended as of March 2000.

(7) Mr. Clark's employment with TheStreet.com ended in February 1999.

                                       8
<PAGE>
                       OPTION GRANTS IN FISCAL YEAR 1999

    The following table sets forth information regarding stock options granted
to our Named Executive Officers in 1999. We have never granted any stock
appreciation rights.

<TABLE>
<CAPTION>
                                                        INDIVIDUAL GRANTS(1)
                                                       ----------------------
                                                       PERCENT OF                            POTENTIAL REALIZABLE
                                                         TOTAL                                 VALUE AT ASSUMED
                                                        OPTIONS                                 ANNUAL RATES OF
                                          NUMBER OF     GRANTED                                   STOCK PRICE
                                          SECURITIES       TO       EXERCISE                     APPRECIATION
                                          UNDERLYING   EMPLOYEES      PRICE                   FOR OPTION TERM(3)
                                           OPTIONS     IN FISCAL       PER      EXPIRATION   ---------------------
NAME                                      GRANTED(#)   YEAR(%)(2)     SHARE        DATE         5%          10%
- ----                                      ----------   ----------   ---------   ----------   ---------   ---------
<S>                                       <C>          <C>          <C>         <C>          <C>         <C>
Kevin W. English(4).....................   262,017        9.80         3.00       3/24/04    4,614,630   6,028,942
                                            83,333        3.12         3.00       3/24/04    1,467,656   1,917,470

Thomas J. Clarke........................    19,940        0.75        20.06      10/17/04      110,512     244,202
                                           230,060        8.60        20.06      10/17/04    1,275,040   2,817,506
                                           250,000        9.35        14.75      12/07/04    1,018,788   2,251,256

Dave Kansas.............................    50,000        1.87         3.00      12/31/03       41,442      91,577

Paul Kothari............................   133,333        4.99         3.00       2/16/04    1,642,046   2,176,811

Michael Zuckert.........................   133,333        4.99         3.00       2/15/04    1,642,046   2,176,811

Simon Clark.............................    16,666        0.62         3.00      12/31/03       13,814      30,524
</TABLE>

- ------------------------

(1) All options were granted under the Plan. The options shown in this table,
    except as otherwise indicated below, become exercisable at a rate of 25%
    annually over four years from the date of grant.

(2) In 1999, we granted options to employees to purchase an aggregate of
    2,673,875 shares of common stock.

(3) Potential realizable value is based on the assumption that our common stock
    appreciates at the annual rate shown, compounded annually, from the date of
    grant until the expiration of the five or ten-year term as applicable. These
    numbers are calculated based on Securities and Exchange Commission
    requirements and do not reflect our projection or estimate of future stock
    price growth. Potential realizable values are computed by multiplying the
    number of shares of common stock subject to a given option by the fair
    market value on the date of grant, as determined by our Board of Directors,
    assuming that the aggregate stock value derived from that calculation
    compounds at the annual 5% or 10% rate shown in the table for the entire
    five or ten-year term of the option and subtracting from that result the
    aggregate option exercise price.

(4) Pursuant to agreements by and between Mr. English and the Company, 75% of
    the shares underlying the remaining unvested options held by Mr. English
    vested fully and were exercised by Mr. English. The remaining 216,665
    options held by Mr. English were terminated.

                                       9
<PAGE>
              AGGREGATED OPTION EXERCISES IN LAST FISCAL YEAR AND
                         FISCAL YEAR-END OPTION VALUES

    The following table sets forth information concerning the exercise of stock
options during the fiscal year ended December 31, 1999 by our Named Executive
Officers and the fiscal year-end value of unexercised options.

<TABLE>
<CAPTION>
                                                                       NUMBER OF SECURITIES
                                                                      UNDERLYING UNEXERCISED         VALUE OF UNEXERCISED
                                                                            OPTIONS AT              IN THE-MONEY OPTIONS AT
                                           SHARES                        DECEMBER 31, 1999             DECEMBER 31, 1999
                                         ACQUIRED ON     VALUE      ---------------------------   ---------------------------
NAME                                     EXERCISE #     REALIZED    EXERCISABLE   UNEXERCISABLE   EXERCISABLE   UNEXERCISABLE
- ----                                     -----------   ----------   -----------   -------------   -----------   -------------
<S>                                      <C>           <C>          <C>           <C>             <C>           <C>
Kevin W. English(1)....................    650,000     11,615,541         --              --             --              --

Thomas Clarke..........................         --             --         --         500,000             --       $1,109,375

Dave Kansas............................         --             --      7,500          72,500        $143,681      $1,240,419

Simon Clark............................         --             --         --              --             --              --

Paul Kothari...........................         --             --         --         133,333             --       $2,158,328

Michael Zuckert........................         --             --         --         133,333             --       $2,158,328
</TABLE>

- --------------------------

(1) Pursuant to agreements by and between Mr. English and the Company, 75% of
    the shares underlying the remaining unvested options held by Mr. English
    vested fully and were exercised by Mr. English. The remaining 216,665
    options held by Mr. English were terminated.

REPORT OF THE COMPENSATION COMMITTEE ON EXECUTIVE COMPENSATION

    The Compensation Committee sets the salaries and other compensation of the
Company's executive officers and other key employees, and is responsible for the
administration of the Company's stock option plan.

    OVERVIEW AND PHILOSOPHY.  The Company is engaged in an industry in which
executives and key employees are the principal productive assets. The Company
faces an intensely competitive market for such persons. In order to succeed, the
Company believes that it must be able to attract and retain qualified
executives. The Company's compensation philosophy for executive officers is to
provide them with competitive compensation opportunities based upon their
contribution to the Company's growth and financial success as well as their own
level of personal performance. A portion of each executive officer's
compensation, therefore, is contingent upon the Company's performance.
Accordingly, the compensation package for each executive officer is comprised of
the following two elements:

    - cash compensation, comprised principally of annual base salary and bonuses
      tied to the achievement of performance goals, financial and otherwise; and

    - equity compensation, comprised principally of stock option awards that
      provide rewards for increases in the value of the Company's Common Stock.

    The Board of Directors believes that as a long-term matter, the Company's
executive compensation policies should attempt to ensure that the Company's
executives and other key employees are compensated at levels that, through a
combination of generous cash and equity-based compensation components,
effectively preempt competitive outside offers. The Compensation Committee is
charged with the responsibility for carrying out this executive compensation
philosophy in individual compensation decisions.

                                       10
<PAGE>
    During 1999, the Compensation Committee had primary responsibility for
determining executive cash compensation levels. The Compensation Committee, as
part of its review and consideration of executive cash compensation, took into
account, among other things, the following goals:

    - providing incentives and rewards to attract and retain highly qualified
      and productive people;

    - motivating employees to high levels of performance, differentiating
      individual executives' pay based on performance;

    - preempting external competitive offers; and

    - ensuring internal equity.

    To achieve these goals, the Company's executive compensation policies
integrate annual base compensation with cash bonuses based on operating
performance with a particular emphasis on attainment of planned objectives, and
on individual initiatives and performance.

    The Compensation Committee has primary responsibility for determining awards
of stock options as part of executive compensation. The Compensation Committee
believes that the grant of stock options aligns executive and stockholder
long-term interests by creating a strong and direct link between executive
compensation and stockholder returns and enables executives to develop and
maintain a significant interest in the long-term growth and profitability of the
Company.

    COMPENSATION OF EXECUTIVE OFFICERS.  Compensation of the Company's executive
officers is comprised of base salary, annual cash incentive compensation,
long-term incentive compensation in the form of stock options and various other
benefits. Each element has a somewhat different purpose and all of the
determinations of the Compensation Committee regarding the appropriate form and
level of executive compensation are ultimately judgments based on the
Compensation Committee's ongoing assessment of the internet content industry,
the Company and the Company's executive officers.

    Base salaries for executive officers in 1999 were generally determined on an
individual basis by evaluating each executive's scope of responsibility,
performance, prior experience and salary history, as well as the salaries for
similar positions at comparable companies. Bonuses were generally established
based on a percentage of base salary as well as the attainment of personal and
company-wide financial and strategic objectives. The Compensation Committee has
not established formulas or assigned specific weights to any of these factors
when making their determinations.

    In 1999, stock options were granted to certain executive officers as hiring
incentives and to aid in the retention of executive officers. The Compensation
Committee may also grant additional stock options to executive officers for
other reasons. In 1999 as part of its annual review and consideration of awards
of stock options, the Compensation Committee considered, among other things, the
same goals as those used in awarding cash compensation and the additional goal
of aligning the interests of executives with the interests of the Company and
its stockholders by ensuring that executives have a direct and continuing stake
in the long-term success of the Company. Stock options generally become
exercisable over a four-year period and are granted at a price that is equal to
the fair market value of the Company's Common Stock on the date of grant. Stock
options to purchase 1,178,682 shares were granted to executive officers in 1999.

    COMPENSATION OF CHIEF EXECUTIVE OFFICER.  The 1999 compensation of Kevin W.
English, who was the Company's chairman of the Board of Directors, chief
executive officer and president until November 1999, was determined by the
Compensation Committee in a manner consistent with the factors considered in
determining the compensation of executive officers, as described above. Pursuant
to an employment agreement entered into by Mr. English with the Company in
October 1998, Mr. English received an annual base salary of $350,000 in 1999 and
a bonus of $110,000. Mr. English also received stock options pursuant to his
employment agreement with the Company.

                                       11
<PAGE>
    In determining the compensation for Thomas Clarke, who replaced Mr. English
as the Company's chief executive officer in November 1999, the Compensation
Committee used the factors described above for the compensation of executive
officers. Mr. Clarke's compensation is described in detail in the section below
entitled "Certain Relationships and Related Transactions--Employment
Agreements."

    INTERNAL REVENUE CODE SECTION 162(M) LIMITATION.  As a result of
Section 162(m) of the Internal Revenue Code, which was enacted into law in 1993,
the Company will not be allowed a federal income tax deduction for compensation
paid to certain executive officers to the extent that compensation exceeds
$1 million per officer in any one year. This limitation will apply to all
compensation paid to the covered executive officers that is not considered to be
performance-based. Compensation which does qualify as performance-based
compensation will not have to be taken into account for purposes of this
limitation. Historically, the combined salary and bonus of each executive
officer has been below the $1.0 million limit.

    This report is submitted by the members of the Compensation Committee:

                                    Ed Glassmeyer
                                    Jerry Colonna

                                       12
<PAGE>
           SECURITY OWNERSHIP OF MANAGEMENT AND CERTAIN STOCKHOLDERS

    The following table sets forth, as of April 28, 2000, the beneficial
ownership of our common stock by (i) each person known by us to own beneficially
more than 5% of our common stock, (ii) each of our directors and nominees for
director, (iii) the Named Executive Officers; and (iv) all of our executive
officers and directors as a group.

<TABLE>
<CAPTION>
                                                               AMOUNT AND NATURE OF
                                                                    BENEFICIAL
NAME AND ADDRESS OF BENEFICIAL OWNER(1)                            OWNERSHIP(2)           PERCENT OF CLASS(2)
- ---------------------------------------                     ---------------------------   -------------------
<S>                                                         <C>                           <C>
Kevin English.............................................                        --                    --

Thomas J. Clarke..........................................                        --                    --

Dave Kansas(3)............................................                   171,515                     *

Simon Clark...............................................                        --                    --

Paul Kothari..............................................                    53,333                     *

Michael Zuckert(4)........................................                    33,333                     *

James J. Cramer(5)........................................                 3,300,951                  13.0%

Cramer Partners, L.L.C. ..................................                 1,306,205                   5.1%

Martin Peretz(6)..........................................                 2,988,482                  11.8%

Peretz Partners, L.L.C. ..................................                 2,430,508                   9.6%

Fred Wilson(7)............................................                   384,975                   1.5%

Jerry Colonna(8)..........................................                   341,292                   1.3%

Edward F. Glassmeyer(9)...................................                 1,682,144                   6.6%

Michael Golden(10)........................................                     7,500                     *

Linda Srere(11)...........................................                    15,000                     *

Oak Investment Partners VIII, L.P. and
  Oak VIII Affiliates Fund, L.P. (9)......................                 1,674,644                   6.6%

Chase Venture Capital Associates, L.P.....................                 1,474,780                   5.8%

Softbank Technology Ventures IV L.P. and
  Softbank Technology Advisors Fund L.P. (12).............                 1,451,499                   5.7%

The New York Times Company(13)............................                 1,560,055                   6.2%

All executive officers and directors as a group (13
  persons)................................................                 8,734,157                  34.4%
</TABLE>

- ------------------------

*   Represents beneficial ownership of less than 1%.

(1) The address for each stockholder, other than Oak Investment Partners VIII,
    L.P., Oak VIII Affiliates Fund, L.P., Chase Venture Capital Associates,
    L.P., Softbank Technology Ventures IV L.P., Softbank Technology Advisors
    Fund L.P. and The New York Times Company, is c/o TheStreet.com, Inc., 14
    Wall Street, 14(th) Floor, New York, NY 10005. The address for Oak
    Investment Partners VIII, L.P. and Oak VIII Affiliates Fund, L.P. is One
    Gorham Island, Wesport, CT 06880. The address for Chase Venture Capital
    Associates, L.P. is 380 Madison Avenue, 12(th) Floor, New York, NY 10017.
    The address for Softbank Technology Ventures IV L.P. and Softbank

                                       13
<PAGE>
    Technology Advisors Fund L.P. is 200 West Evelyn Ave., Suite 200 Mountain
    View, CA 94043. The address for The New York Times Company is 229 West
    43(rd) Street, New York, NY 10036.

(2) Beneficial ownership is determined in accordance with the rules of the
    Securities and Exchange Commission. Percentage ownership is based on
    25,366,313 shares outstanding as of April 28, 2000. Shares of common stock
    subject to options currently exercisable or exercisable within 60 days of
    April 28, 2000 are deemed outstanding for the purpose of computing the
    percentage ownership of the person holding such options but are not deemed
    outstanding for computing the percentage ownership of any other person.
    Except as noted, the persons and entities named in the table have sole
    voting and sole investment power with respect to all shares beneficially
    owned, subject to community property laws where applicable.

(3) Consists of 151,515 shares owned directly by Mr. Kansas, 7,500 shares
    underlying stock options that became exercisable in July 1999 and 12,500
    shares underlying stock options that became exercisable in January 2000.

(4) Consists of 33,333 shares underlying stock options that became exercisable
    in February 2000.

(5) Consists of 1,306,205 shares owned by Cramer Partners, L.L.C., 232,071
    shares owned by a trust for the benefit of Mr. Cramer, of which he acts as
    trustee, 1,213,415 shares owned by a second trust for the benefit of
    Mr. Cramer, of which he also acts as trustee, 125,000 shares owned by Cramer
    Partners, L.P., 83,333 shares underlying stock options that became
    exercisable in February 2000 and 7,500 shares underlying stock options that
    will become exercisable in May 2000.

(6) Consists of 152,474 shares owned directly by Dr. Peretz, 7,500 shares
    underlying stock options held by Dr. Peretz that will become exercisable in
    May 2000, 2,430,508 shares owned by Peretz Partners, L.L.C., 224,129 shares
    owned by the family of Dr. Peretz, including his spouse and children, 13,174
    shares held by each of two trusts, for each of which Dr. Peretz is a
    co-trustee, 68,618 shares held by a trust for the benefit of Dr. Peretz,
    74,089 shares held by a trust for the benefit of Dr. Peretz's spouse and
    1,000 shares held by each of four other family trusts, for each of which
    Dr. Peretz is a co-trustee. Dr. Peretz disclaims beneficial ownership of
    shares owned by Peretz Partners, L.L.C.

(7) Consists of 92,866 shares owned directly by Mr. Wilson, 7,500 shares
    underlying stock options held by Mr. Wilson that will become exercisable in
    May 2000, 130,000 shares owned by The Flatiron Fund, L.L.C., 114,368 shares
    owned by The Flatiron Fund 1998/99, L.L.C., of each of which Mr. Wilson and
    Mr. Colonna are general partners and 40,241 shares owned by a family trust.

(8) Consists of 130,000 shares owned by The Flatiron Fund, L.L.C. and 114,368
    shares owned by The Flatiron Fund 1998/99, L.L.C., of each of which
    Mr. Colonna and Mr. Wilson are general partners, and 89,424 shares owned by
    a family investment company and 7,500 shares underlying stock options held
    by Mr. Colonna that will become exercisable in May 2000.

(9) Consists of 1,642,827 shares owned by Oak Investment Partners VIII, L.P. and
    31,817 shares owned by Oak VIII Affiliates Fund, L.P., 7,358 shares
    underlying stock options held by Oak Investment Partners VIII, L.P. and
    142 shares underlying stock options held by Oak VII Affiliates Fund, L.P.,
    all of which will become exercisable in May 2000. Mr. Glassmeyer is a
    managing member of Oak Associates VIII, L.L.C., which is the general partner
    of Oak Investment Partners VIII, L.P. and of Oak VIII Affiliates, L.L.C.,
    which is the general partner of Oak VIII Affiliates Fund, L.P.
    Mr. Glassmeyer disclaims beneficial ownership of these shares.

(10) Consists of 7,500 shares underlying options granted to Mr. Golden, which
    will become exercisable in May 2000. Mr. Golden serves as vice chairman and
    senior vice president of The New York Times Company and sits as a director
    of TheStreet.com at the request of The New York Times Company in connection
    with its investment in TheStreet.com. Pursuant to The New York Times

                                       14
<PAGE>
    Company's policy, Mr. Golden has agreed that he will turn over to The New
    York Times Company any net profits he realizes as a result of the exercise
    of such options.

(11) Consists of 15,000 shares underlying options granted to Ms. Srere, which
    will become exercisable in May 2000.

(12) Consists of 1,423,025 shares owned by Softbank Technology Ventures IV L.P.
    and 28,474 owned by Softbank Technology Advisors Fund L.P. Mr. Charles R.
    Lax is the managing member of STV IV LLC which is the general partner of
    each of Softbank Technology Ventures IV L.P. and Softbank Technology
    Advisors Fund L.P. Both Mr. Lax and STV IV LLC disclaim beneficial ownership
    of these shares.

(13) Consists of 1,552,555 shares owned by The New York Times Company and 7,500
    shares underlying options granted to Michael Golden, which will become
    exercisable in May 2000. Mr. Golden serves as vice chairman and senior vice
    president of The New York Times Company and sits as a director of
    TheStreet.com at the request of The New York Times Company in connection
    with its investment in TheStreet.com. Pursuant to The New York Times
    Company's policy, Mr. Golden has agreed that he will turn over to The New
    York Times Company any net profits he realizes as a result of the exercise
    of such options.

            SECTION 16(A) BENEFICIAL OWNERSHIP REPORTING COMPLIANCE

    Section 16(a) of the Securities Exchange Act of 1934, as amended (the
"Exchange Act"), requires the Company's directors and executive officers, and
persons who own more than 10% of the Company's outstanding Common Stock, to file
initial reports of ownership and reports of changes in ownership of Common Stock
with the SEC and Nasdaq. Such persons are required by SEC regulations to furnish
the Company with copies of all Section 16(a) reports they file.

    Based solely on its review of such reports received by the Company with
respect to fiscal 1999 and written representations from such reporting persons,
the Company believes that all reports required to be filed under Section 16(a)
have been filed by such persons.

                 CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS

THE NEW YORK TIMES INVESTMENT

    In February 1999, the Company sold 37,728 shares of our Series B 9 1/2%
Cumulative Preferred Stock and 1,320,901 shares of our Common Stock to The New
York Times Company for an aggregate consideration of $15 million in cash and
services. In connection with this sale, the Company entered into an advertising
credit agreement with The New York Times Company under which The New York Times
Company has agreed to provide the Company with an advertising credit for
advertising on The New York Times and other media controlled by it.
Additionally, as part of this transaction, Mr. Michael Golden, the vice chairman
and senior vice president of The New York Times Company, became a director of
TheStreet.com. In March 1999, the Company entered into a memorandum of
understanding with The New York Times Electronic Media Company under which the
Company agreed to the following proposals, a majority of which were implemented
by December 31, 1999:

    - Promotion of our web site by The New York Times to registered users of its
      web site;

    - Indexing of our headlines on the Business section of The New York Times
      web site and indexing of headlines from the Business section of The New
      York Times web site on our web site;

    - Licensing our investment tools to The New York Times; and

    - Creating a jointly owned newsroom to provide continuous coverage of
      business news.

                                       15
<PAGE>
THE STREET.COM (EUROPE) LIMITED INVESTMENT

    In September 1999, the Company and a syndicate of investors (the
"Syndicate") invested a total of $17 million in TheStreet.com (Europe) Limited.
Members of the Syndicate include, among others, Chase Capital Partners, Barclays
Private Equity, ETF Group, 3i, and Intel Corporation. Chase Capital Partners is
an affiliate of The Flatiron Fund, L.L.C. of which two of our directors, Fred
Wilson and Jerry Colonna, are general partners. The principal terms of the
investment are as follows:

    - A preferred dividend of $5 million (plus interest) payable to the
      Syndicate, which will convert into shares upon a public offering of shares
      or a sale of TheStreet.com (Europe) Limited;

    - The license of certain intellectual property of the Company (including,
      without limitation, use of the name "TheStreet.com") to TheStreet.com
      (Europe) Limited for $1 million;

    - The transfer of certain software in from the Company to TheStreet.com
      (Europe) Limited for $9 million; and

    - The subscription by the Company for a $10 million loan note, the principal
      of and interest upon which will accrue and convert into shares upon a
      public offering of shares or sale of TheStreet.com (Europe) Limited.

DIRECTOR LOAN AGREEMENT

    On April 18, 2000, the Company entered into a loan agreement with David
Kansas, a Class II director of the Company, whereby the Company agreed to loan
to Mr. Kansas the sum of $100,000 at the prime rate on such date plus one
percentage point. The full amount of the loan is payable upon its maturity date
on April 17, 2001. Mr. Kansas may prepay the loan in whole, or in part, at any
time, without penalty.

EMPLOYMENT AGREEMENTS

    In February 1999, the Company entered into an employment agreement with
James Cramer, an outside contributor, which superseded an earlier employment
agreement. The agreement provides for an annual salary of $250,000, which
increases annually by 10%. Pursuant to such agreement, the Company granted
Mr. Cramer an option to purchase 333,333 shares of Common Stock at an exercise
price of $3.00 per share. The option becomes exercisable at a rate of 25%
annually commencing in February 2000. This agreement terminates in
February 2003. In December 1999 the Company entered into an agreement with
Mr. Cramer to amend Mr. Cramer's employment agreement of February 1999. Pursuant
to such agreement Mr. Cramer agreed to forego his annual base salary of $275,000
for the calendar year 2000 in exchange for the grant of an option to purchase
30,000 shares of the Company's Common Stock at an exercise price of $19.00 per
share, the price at which the Company's shares were offered to the public in the
Company's initial public offering in May 1999. The shares of Common Stock
underlying the options will fully vest on December 31, 2000 and the option will
expire on March 31, 2001. We maintain a "key person" life insurance policy for
Mr. Cramer.

    In February 1999, the Company entered into a two-year employment agreement
with Paul K. Kothari, as vice-president and chief financial officer. The
agreement provides for an annual salary of $225,000 and a guaranteed annual
bonus of $25,000. The annual salary may be increased during the term of the
agreement in the sole discretion of the Compensation Committee. In addition,
Mr. Kothari is bound by a non-compete clause from the commencement date of the
employment agreement through the first twelve months after the cessation of
Mr. Kothari's employment. The employment agreement terminates in February 2001.
Mr. Kothari's employment with the Company ended at the end of April 2000.

    In February 1999, the Company entered into a two-year employment agreement
with Michael S. Zuckert, as vice-president, secretary and general counsel. The
agreement provides for an annual salary of $225,000 and a guaranteed annual
bonus of no less than $25,000. The annual salary may be

                                       16
<PAGE>
increased during the term of the agreement in the sole discretion of the
Compensation Committee. In addition, Mr. Zuckert is bound by a non-compete
clause from the commencement date of the employment agreement through the first
twelve months after the cessation of Mr. Zuckert's employment. The employment
agreement terminates in February 2001. Mr. Zuckert's employment with the Company
ended in March 2000.

    In December 1999, the Company entered into a two-year employment agreement
with Thomas J. Clarke, Jr., as President and Chief Executive Officer. The
agreement provides for an annual salary of $350,000 and a guaranteed annual
bonus of no less than $50,000. The annual salary may be increased during the
term of the agreement in the sole discretion of the Compensation Committee.
Under the agreement, the Company granted Mr. Clarke an option to purchase
250,000 shares of Common Stock at an exercise price of $20.06. In addition,
Mr. Clarke is bound by a non-compete clause from the commencement date of the
employment agreement through the first twelve months after the cessation of
Mr. Clarke's employment. The employment agreement terminates in December 2001.

                       COMMON STOCK PERFORMANCE GRAPH(1)

    Set forth below is a graph comparing the seven-month percentage change in
the cumulative total stockholder return on the Company's Common Stock from
May 11, 1999 (the date of the Company's initial public offering) through
December 31, 1999 with the cumulative total return on the S&P 500 Index and a
self-constructed peer group index. The comparison assumes $100 was invested on
May 11, 1999 in the Company's Common Stock and in each of the foregoing indices
and assumes reinvestment of dividends. The initial public offering price of The
Street.com's common stock was $19.00 per share.

                      COMPARISON OF SEVEN-MONTH CUMULATIVE
                  TOTAL RETURN AMONG THESTREET.COM, INC., THE
              S&P 500 INDEX AND AN INDUSTRY SPECIFIC PEER GROUP(2)

EDGAR REPRESENTATION OF DATA POINTS USED IN PRINTED GRAPHIC

<TABLE>
<CAPTION>
          THE STREET.COM, INC.  S & P 500 INDEX  PEER GROUP
<S>       <C>                   <C>              <C>
5/11/99                $100.00          $100.00     $100.00
12/31/99                $31.98          $109.26      $72.60
</TABLE>

                                                   (FOOTNOTES ON FOLLOWING PAGE)

                                       17
<PAGE>
- ------------------------

(1) This section entitled "Common Stock Performance Chart" shall not be
    incorporated by reference into any future filings by the TheStreet.com, Inc.
    under the Securities Act or Exchange Act, and shall not be deemed to be
    soliciting material or to be filed under the Securities Act or Exchange Act.

(2) The peer group consists of the following companies:

    (i) Cnet, Inc.,

    (ii) ilife.com, Inc.,

    (iii) iVillage, Inc.,

    (iv) Marketwatch.com, Inc. and

    (V) Multex.com, Inc.

                             STOCKHOLDER PROPOSALS

    Stockholders may submit proposals on matters appropriate for stockholder
action at subsequent annual meetings of the Company consistent with Rule 14a-8
promulgated under the Exchange Act, which in certain circumstances may require
the inclusion of qualifying proposals in the Company's Proxy Statement. For such
proposals to be considered for inclusion in the Proxy Statement and proxy
relating to the Company's 2001 Annual Meeting of Stockholders, all applicable
requirements of Rule 14a-8 must be satisfied and such proposals must be received
by the Company no later than January 31, 2001. Such proposals should be directed
to The Street.com, Inc., Attention: Secretary, at 14 Wall Street 14(th) Floor,
New York, New York 10005.

    Except in the case of proposals made in accordance with Rule 14a-8, the
Company's Bylaws require that stockholders desiring to bring any business before
the Company's 2001 Annual Meeting of Stockholders deliver written notice thereof
to the Company not less than 60 days nor more than 90 days prior to the
anniversary date of the immediately preceding annual meeting of stockholders and
comply with all other applicable requirements of the Bylaws. However, in the
event that the 2001 annual meeting is called for a date that is not within
30 days before or after the anniversary date of the 2000 Annual Meeting of
Stockholders, notice by the stockholder in order to be timely must be received
not later than the close of business on the 10(th) day following the date on
which notice of the date of the annual meeting was mailed to stockholders or
made public, whichever first occurs. In order for a proposal made outside of the
requirements of Rule 14a-8 to be "timely" within the meaning of Rule 14a-4(c),
such proposal must be received by the Company in accordance with the time limits
set forth in the foregoing advance notice Bylaw provision.

                                 OTHER MATTERS

    The Board of Directors knows of no matters other than those described herein
that will be presented for consideration at the Meeting. However, should any
other matters properly come before the Meeting or any adjournment or
postponement thereof, it is the intention of the persons named in the
accompanying proxy card to vote in accordance with their best judgment in the
interests of the Company.

                                 MISCELLANEOUS

    All costs incurred in the solicitation of proxies will be borne by the
Company. In addition to the solicitation by mail, officers and employees of the
Company may solicit proxies by mail, facsimile, telephone or in person, without
additional compensation. The Company may also make arrangements with brokerage
houses and other custodians, nominees and fiduciaries for the forwarding of
solicitation materials to the beneficial owners of Common Stock held of record
by such persons, and the Company

                                       18
<PAGE>
may reimburse such brokerage houses and other custodians, nominees and
fiduciaries for their out-of-pocket expenses incurred in connection therewith.

    The Company's Annual Report on Form 10-K with respect to the fiscal year
ended December 31, 1999, which includes the Company's audited financial
statements, accompanies this Proxy Statement.

    ADDITIONAL COPIES OF THE COMPANY'S ANNUAL REPORT ON FORM 10-K WILL BE
FURNISHED AT NO CHARGE TO EACH PERSON TO WHOM A PROXY STATEMENT IS DELIVERED
UPON RECEIPT OF A WRITTEN OR ORAL REQUEST OF SUCH PERSON ADDRESSED TO THE
STREET.COM, INC., ATTN: SECRETARY, 14 WALL STREET 14(TH) FLOOR, NEW YORK, NEW
YORK 10005 (TELEPHONE: (212) 321-5000).

                                          By Order of the Board of Directors
                                          /s/ Jordan Goldstein
                               -------------------------------------------------
                                          Jordan Goldstein
                                          SECRETARY
                                          New York, New York
                                          May 30, 2000

                                       19
<PAGE>
                                                                       EXHIBIT A

                              THESTREET.COM, INC.
                           1998 STOCK INCENTIVE PLAN
                 AS AMENDED AND RESTATED AS OF NOVEMBER 1, 1999

SECTION 1  PURPOSES

    The purpose of TheStreet.com, Inc. 1998 Stock Incentive Plan, as amended and
restated as of November 1, 1999 (the "Plan") is to enable TheStreet.com, Inc.
(the "Company") and its Related Companies (as defined below) to attract, retain
and reward employees, directors and consultants and strengthen the existing
mutuality of interests between such persons and the Company's stockholders by
offering such persons an equity interest in the Company. For purposes of the
Plan, a "Related Company" means any corporation, partnership, joint venture or
other entity in which the Company owns, directly or indirectly, at least a 20%
beneficial ownership interest.

SECTION 2  TYPES OF AWARDS

    Awards under the Plan may be in the form of (i) Stock Options;
(ii) Restricted Stock; and/or (iii) Tax Offset Payments.

SECTION 3  ADMINISTRATION

    3.1  The Plan shall be administered by the Compensation Committee of the
Company's Board of Directors (the "Board") or such other committee of directors
as the Board shall designate (the "Committee"), which shall consist of not less
than two directors. The members of the Committee shall serve at the pleasure of
the Board.

    3.2  The Committee shall have the following authority with respect to awards
under the Plan: to grant awards; to adopt, alter and repeal such administrative
rules, guidelines and practices governing the Plan as it shall deem advisable;
to interpret the terms and provisions of the Plan and any award granted under
the Plan; and to otherwise supervise the administration of the Plan. In
particular, and without limiting its authority and powers, the Committee shall
have the authority:

        (1) to determine whether and to what extent any award or combination of
    awards will be granted hereunder;

        (2) to select the employees, directors or consultants to whom awards
    will be granted;

        (3) to determine the number of shares of the common stock of the Company
    (the "Stock") to be covered by each award granted hereunder subject to the
    limitations contained herein;

        (4) to determine the terms and conditions of any award granted
    hereunder, including, but not limited to, any vesting or other restrictions
    based on such performance objectives (the "Performance Objectives") and such
    other factors as the Committee may establish, and to determine whether the
    Performance Objectives and other terms and conditions of the award are
    satisfied;

        (5) to determine the treatment of awards upon an award holder's
    retirement, disability, death, termination for cause or other termination of
    employment or service;

        (6) to determine that amounts equal to the amount of any dividends
    declared with respect to the number of shares covered by an award (i) will
    be paid to the employee currently or (ii) will be deferred and deemed to be
    reinvested or (iii) will otherwise be credited to the employee, or that the
    employee has no rights with respect to such dividends;

                                      A-1
<PAGE>
        (7) to amend the terms of any award, prospectively or retroactively;
    provided, however, that no amendment shall impair the rights of the award
    holder without his or her written consent; and

        (8) to substitute new Stock Options for previously granted Stock
    Options, or for options granted under other plans or agreements, in each
    case including previously granted options having higher option prices.

    3.3  The Committee shall have the right to designate awards as "Performance
Awards." The grant or vesting of a Performance Award shall be subject to the
achievement of Performance Objectives established by the Committee based on one
or more of the following criteria, in each case applied to the Company on a
consolidated basis and/or to a business unit and which the Committee may use as
an absolute measure, as a measure of improvement relative to prior performance,
or as a measure of comparable performance relative to a peer group of companies:
sales, operating profits, operating profits before interest expense and taxes,
net earnings, earnings per share, return on equity, return on assets, return on
invested capital, total shareholder return, cash flow, debt to equity ratio,
market share, stock price, economic value added, and market value added.

    3.4  All determinations made by the Committee pursuant to the provisions of
the Plan shall be final and binding on all persons, including the Company and
Plan participants.

SECTION 4  STOCK SUBJECT TO PLAN

    4.1  The total number of shares of Stock which may be issued under the Plan
shall be 6,900,000. Such shares may consist of authorized but unissued shares or
treasury shares.

    4.2  To the extent a Stock Option terminates without having been exercised,
or shares awarded are forfeited, the shares subject to such award shall again be
available for distribution in connection with future awards under the Plan.
Shares of Stock equal in number to the shares surrendered in payment of the
option price, and shares of Stock which are withheld in order to satisfy
federal, state or local tax liability, shall not count against the above limit,
and shall again be available for grants under the Plan.

    4.3  No employee shall be granted Stock Options, Restricted Stock, or any
combination thereof with respect to more than 1,000,000 shares of Stock in any
fiscal year (subject to adjustment as provided in Section 4.4). No employee
shall be granted a Tax Offset Payment in any fiscal year with respect to more
than the number of shares of Stock covered by awards granted to such employee in
such fiscal year.

    4.4  In the event of any merger, reorganization, consolidation, sale of
substantially all assets, recapitalization, Stock dividend, Stock split,
spin-off, split-up, split-off, distribution of assets or other change in
corporate structure affecting the Stock, a substitution or adjustment, as may be
determined to be appropriate by the Committee or the Board in its sole
discretion, shall be made in the aggregate number of shares reserved for
issuance under the Plan, the number of shares as to which awards may be granted
to any individual in any fiscal year, the number of shares subject to
outstanding awards and the amounts to be paid by award holders or the Company,
as the case may be, with respect to outstanding awards; provided, however, that
no such adjustment shall increase the aggregate value of any outstanding award.

SECTION 5  ELIGIBILITY

    Employees, directors, and consultants of the Company or a Related Company
are eligible to be granted awards under the Plan. Only employees are eligible to
be granted Incentive Stock Options. The participants under the Plan shall be
selected from time to time by the Committee, in its sole discretion, from among
those eligible.

                                      A-2
<PAGE>
SECTION 6  STOCK OPTIONS

    6.1  The Stock Options awarded to employees under the Plan may be of two
types: (i) Incentive Stock Options within the meaning of Section 422 of the Code
or any successor provision thereto; and (ii) Non-Qualified Stock Options. To the
extent that any Stock Option does not qualify as an Incentive Stock Option, it
shall constitute a Non-Qualified Stock Option.

    6.2  Subject to the following provisions, Stock Options awarded under the
Plan shall be in such form and shall have such terms and conditions as the
Committee may determine:

        (1) OPTION PRICE. The option price per share of Stock purchasable under
    a Stock Option shall be determined by the Committee, and may be less than
    the fair market value of the Stock on the date of the award of the Stock
    Option. For purposes of the Plan, "fair market value" shall mean the closing
    price of a share of Stock on the NASDAQ National Market on the trading day
    immediately preceding the date of grant.

        (2) OPTION TERM. The term of each Stock Option shall be fixed by the
    Committee.

        (3) EXERCISABILITY. Stock Options shall be exercisable at such time or
    times and subject to such terms and conditions as shall be determined by the
    Committee. The Committee may waive such exercise provisions or accelerate
    the exercisability of the Stock Option at any time in whole or in part.

        (4) METHOD OF EXERCISE. Stock Options may be exercised in whole or in
    part at any time during the option period by giving written notice of
    exercise, in such manner as may be determined by the Company, specifying the
    number of shares to be purchased, accompanied by payment of the purchase
    price. Payment of the purchase price shall be made in such manner as the
    Committee may provide in the award, which may include cash (including cash
    equivalents), delivery of shares of Stock already owned by the optionee or
    subject to awards hereunder, "cashless exercise", any other manner permitted
    by law determined by the Committee, or any combination of the foregoing. If
    the Committee determines that a Stock Option may be exercised using shares
    of Restricted Stock, then unless the Committee provides otherwise, the
    shares received upon the exercise of a Stock Option which are paid for using
    Restricted Stock shall be restricted in accordance with the original terms
    of the Restricted Stock award.

        (5) NO STOCKHOLDER RIGHTS. An optionee shall have neither rights to
    dividends or other rights of a stockholder with respect to shares subject to
    a Stock Option until the optionee has given written notice of exercise and
    has paid for such shares.

        (6) SURRENDER RIGHTS. The Committee may provide that options may be
    surrendered for cash upon any terms and conditions set by the Committee.

        (7) NON-TRANSFERABILITY. Unless otherwise provided by the Committee,
    (i) Stock Options shall not be transferable by the optionee other than by
    will or by the laws of descent and distribution, and (ii) during the
    optionee's lifetime, all Stock Options shall be exercisable only by the
    optionee or by his or her guardian or legal representative.

        (8) TERMINATION OF EMPLOYMENT. Following the termination of an
    optionee's employment with the Company or a Related Company, the Stock
    Option shall be exercisable to the extent determined by the Committee. The
    Committee may provide different post-termination exercise provisions with
    respect to termination of employment for different reasons. The Committee
    may provide that, notwithstanding the option term fixed pursuant to
    Section 6.2(b), a Stock Option which is outstanding on the date of an
    optionee's death shall remain outstanding for an additional period after the
    date of such death.

                                      A-3
<PAGE>
    6.3  Notwithstanding the provisions of Section 6.2, no Incentive Stock
Option shall (i) have an option price which is less than 100% of the fair market
value of the Stock on the date of the award of the Incentive Stock Option,
(ii) be exercisable more than ten years after the date such Incentive Stock
Option is awarded, or (iii) be awarded more than ten years after May 6, 1998,
the original effective date of the Plan. No Incentive Stock Option granted to an
employee who owns more than 10% of the total combined voting power of all
classes of stock of the Company or any of its parent or subsidiary corporations,
as defined in Section 424 of the Code, shall (A) have an option price which is
less than 110% of the fair market value of the Stock on the date of award of the
Incentive Stock Option or (B) be exercisable more than five years after the date
such Incentive Stock Option is awarded.

SECTION 7  RESTRICTED STOCK

    Subject to the following provisions, all awards of Restricted Stock to
employees shall be in such form and shall have such terms and conditions as the
Committee may determine:

        (1) The Restricted Stock award shall specify the number of shares of
    Restricted Stock to be awarded, the price, if any, to be paid by the
    recipient of the Restricted Stock and the date or dates on which, or the
    conditions upon the satisfaction of which, the Restricted Stock will vest.
    The grant and/or the vesting of Restricted Stock may be conditioned upon the
    completion of a specified period of service with the Company or a Related
    Company, upon the attainment of specified Performance Objectives or upon
    such other criteria as the Committee may determine.

        (2) Stock certificates representing the Restricted Stock awarded to an
    employee shall be registered in the employee's name, but the Committee may
    direct that such certificates be held by the Company or its designee on
    behalf of the employee. Except as may be permitted by the Committee, no
    share of Restricted Stock may be sold, transferred, assigned, pledged or
    otherwise encumbered by the employee until such share has vested in
    accordance with the terms of the Restricted Stock award. At the time
    Restricted Stock vests, a certificate for such vested shares shall be
    delivered to the employee (or his or her designated beneficiary in the event
    of death), free of all restrictions.

        (3) The Committee may provide that the employee shall have the right to
    vote or receive dividends on Restricted Stock. Unless the Committee provides
    otherwise, Stock received as a dividend on, or in connection with a stock
    split of, Restricted Stock shall be subject to the same restrictions as the
    Restricted Stock.

        (4) Except as may be provided by the Committee, in the event of an
    employee's termination of employment before all of his or her Restricted
    Stock has vested, or in the event any conditions to the vesting of
    Restricted Stock have not been satisfied prior to any deadline for the
    satisfaction of such conditions set forth in the award, the shares of
    Restricted Stock which have not vested shall be forfeited, and the Committee
    may provide that (i) any purchase price paid by the employee shall be
    returned to the employee or (ii) a cash payment equal to the Restricted
    Stock's fair market value on the date of forfeiture, if lower, shall be paid
    to the employee.

        (5) The Committee may waive, in whole or in part, any or all of the
    conditions to receipt of, or restrictions with respect to, any or all of the
    employee's Restricted Stock.

SECTION 8  TAX OFFSET PAYMENTS

    The Committee may provide for a Tax Offset Payment by the Company to an
employee with respect to one or more awards granted under the Plan. The Tax
Offset Payment shall be in an amount specified by the Committee, which shall not
exceed the amount necessary to pay the federal, state, local and other taxes
payable with respect to the applicable award and the receipt of the Tax Offset
Payment,

                                      A-4
<PAGE>
assuming that the employee is taxed at the maximum tax rate applicable to such
income. The Tax Offset Payment shall be paid solely in cash.

SECTION 9  TAX WITHHOLDING

    Each award holder shall, no later than the date as of which the value of an
award first becomes includible in such person's gross income for applicable tax
purposes, pay, pursuant to such arrangements as the Company may establish from
time to time, any federal, state, local or other taxes of any kind required by
law to be withheld with respect to the award. The obligations of the Company
under the Plan shall be conditional on such payment, and the Company (and, where
applicable, any Related Company), shall, to the extent permitted by law, have
the right to deduct any such taxes from any payment of any kind otherwise due to
the employee.

SECTION 10  AMENDMENTS AND TERMINATION

    The Plan is of unlimited duration. The Board may discontinue the Plan at any
time and may amend it from time to time. No amendment or discontinuation of the
Plan shall adversely affect any award previously granted without the award
holder's written consent. Amendments may be made without stockholder approval
except as required to satisfy regulatory requirements.

SECTION 11  CHANGE OF CONTROL

    11.1  In the event of a Change of Control, if so determined by the Committee
and specifically documented in either a special form of agreement at the time of
grant or an amendment to an existing agreement, in each case on an
individual-by-individual basis:

        (1) all or a portion (as determined by the Committee) of outstanding
    Stock Options awarded to such individual under the Plan shall become fully
    exercisable and vested; and

        (2) the restrictions applicable to all or a portion (as determined by
    the Committee) of any outstanding Restricted Stock awards under the Plan
    held by such individual shall lapse and such shares shall be deemed fully
    vested.

    11.2  A "Change of Control" means the happening of any of the following:

        (1) the acquisition by any person or group deemed a person under
    Sections 3(a)(9) and 13(d)(3) of the Securities Exchange Act of 1934 (the
    "Exchange Act") (other than the Company and its subsidiaries as determined
    immediately prior to that date) of beneficial ownership, directly or
    indirectly (with beneficial ownership determined as provided in Rule 13d-3,
    or any successor rule, under the Exchange Act), of a majority of the total
    combined voting power of all classes of stock of the Company having the
    right under ordinary circumstances to vote at an election of the Board of
    Directors of the Company, if such person or group deemed a person prior to
    such acquisition was not a beneficial owner of at least five percent (5%) of
    such total combined voting power of the Company;

        (2) the election to the Board of Directors of the Company of members as
    a result of which a majority of the Board of Directors shall consist of
    persons who are not members of the Board of Directors as of the date of
    grant;

        (3) the date of approval by the stockholders of the Company of an
    agreement providing for the merger or consolidation of the Company with
    another corporation or other entity where (x) stockholders of the Company
    immediately prior to such merger or consolidation would not beneficially own
    following such merger or consolidation shares entitling such stockholders to
    a majority of all votes (without consolidation of the rights of any class of
    stock to elect directors by a separate class vote) to which all stockholders
    of the surviving corporation would be entitled in the

                                      A-5
<PAGE>
    election of directors, or (y) where the members of the Board of Directors,
    immediately prior to such merger or consolidation, would not, immediately
    after such merger or consolidation, constitute a majority of the board of
    directors of the surviving corporation; or

        (4) the sale of all or substantially all of the assets of the Company.

SECTION 12  GENERAL PROVISIONS

    12.1  If at any time the Committee determines that the delivery of Common
Stock under the Plan is or may be unlawful under the laws of any applicable
jurisdiction, the right to exercise any Stock Option or receive any Restricted
Stock shall be suspended until the Committee determines that such delivery is
lawful. The Company shall have no obligation to effect any registration of
qualification of the Common Stock under federal or state laws.

    12.2  Any person exercising a Stock Option or receiving Restricted Stock
shall make such representations (including representations to the effect that
such person will not dispose of the Common Stock so acquired in violation of
federal and state securities laws) and furnish such information as may, in the
opinion of counsel for the Company, be appropriate to permit the Company to
issue the Common Stock in compliance with applicable federal and state
securities laws. The Committee may refuse to permit the exercise of such Stock
Option or delivery of such Restricted Stock until such representations and
information have been provided.

    12.3  The Company may place an appropriate legend evidencing any transfer
restrictions on all shares of Common Stock issued under the Plan and may issue
stop transfer instructions in respect thereof.

    12.4  Nothing set forth in this Plan shall prevent the Board from adopting
other or additional compensation arrangements. Neither the adoption of the Plan
nor any award hereunder shall confer upon any employee of the Company, or of a
Related Company, any right to continued employment or service as a director or
consultant.

    12.5  Determinations by the Committee under the Plan relating to the form,
amount, and terms and conditions of awards need not be uniform, and may be made
selectively among persons who receive or are eligible to receive awards under
the Plan, whether or not such persons are similarly situated.

    12.6  No member of the Board or the Committee, nor any officer or employee
of the Company acting on behalf of the Board or the Committee, shall be
personally liable for any action, determination or interpretation taken or made
with respect to the Plan, and all members of the Board or the Committee and all
officers or employees of the Company acting on their behalf shall, to the extent
permitted by law, be fully indemnified and protected by the Company in respect
of any such action, determination or interpretation.

                                      A-6
<PAGE>

               v Please Detach and Mail in the Envelope Provided v

- --------------------------------------------------------------------------------

                              THE STREET.COM, INC.

   Proxy Solicited on Behalf of the Board of Directors For Annual Meeting of
                          Stockholders, July 12, 2000

The undersigned hereby appoints Thomas J. Clarke and Jordan Goldstein, each
with power to act without the other and with full power of substitution and
resubstitution, as Proxies to represent and to vote, as designated on the
reverse side, all shares of Common Stock, $.01 par value, of The Street.com,
Inc. (the "Company") owned by the undersigned, at the Annual Meeting of
Stockholders (the "Meeting") to be held at the TriBeCa Grand Hotel, Two
Avenue of the Americas, New York, New York 10013, on July 12, 2000,
commencing at 10:00 a.m., New York City time, upon such business as may
properly come before the Meeting or any adjournment or postponement thereof,
including the matters set forth on the reverse side. You are encouraged to
specify your choice by marking the appropriate box (SEE REVERSE SIDE) but you
need not mark any box if you wish to vote in accordance with the Board of
Directors' recommendations. The Proxies cannot vote your shares unless you
sign and return this card. Unless a contrary direction is indicated this
Proxy will be voted for all nominees and for Proposals 2 and 3, as more
specifically described in the Proxy Statement. If specific instructons are
indicated, this Proxy will be voted in accordance therewith.

                  (Continued and to be signed on reverse side)

- --------------------------------------------------------------------------------
<PAGE>

              v Please Detach and Mail in the Envelope Provided v
- --------------------------------------------------------------------------------

|X| Please mark your
    votes as indicated
    in this example


THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT STOCKHOLDERS VOTE:

FOR EACH OF THE PERSONS LISTED BELOW AS A NOMINEE TO SERVE AS A CLASS I DIRECTOR
    OF THE COMPANY;

FOR THE APPROVAL OF THE AMENDMENT TO THE COMPANY'S AMENDED AND RESTATED 1998
    STOCK INCENTIVE PLAN; AND

FOR THE APPROVAL OF THE RATIFICATION OF THE APPOINTMENT OF ARTHUR ANDERSEN LLP
    AS THE COMPANY'S INDEPENDENT CERTIFIED PUBLIC ACCOUNTANTS


    ----------------------------------------------

                                                FOR ALL  AGAINST ALL  EXCEPTIONS

1. Election of Class I Directors                  |_|        |_|         |_|

Nominees: James J. Cramer, Michael Golden and
          Martin Peretz

Exceptions:
           ----------------------------------

                                                  FOR      AGAINST     ABSTAIN

2. Approval of the amendment to the Company's     |_|        |_|         |_|
   Amended and Restated 1998 Stock Incentive
   Plan to increase the number of shares of
   Common Stock available fo grant pursuant
   to awards under the Plan from 4,400,000
   shares to 6,900,000 shares.

                                                  FOR      AGAINST     ABSTAIN

3. Approval of the ratification of the            |_|        |_|         |_|
   appointment of Arthur Andersen LLP as the
   Company's independent certified public
   accountants for the fiscal year ending
   December 31, 2000.


                                                                  Date:    ,2000
- -------------------------------  --------------------------------      ----
   Signature (title, if any)        Signature, if held jointly

Please sign name(s) exactly as appearing hereon. When signing as attorney,
executor, administrator or other fiduciary, please give your full title as such.
Joint owners should each sign personally. If a corporation, sign in full
corporate name, by authorized officer. If a partnership, please sign in
partnership name, by authorized person.


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