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                                                                    EXHIBIT 4.16

The Warrant and the securities issuable upon exercise of this Warrant (the
"Securities") have not been registered under the Securities Act of 1933 (the
"Securities Act") or under any state securities or Blue Sky laws ("B1ue Sky
Laws"). No transfer, sale, assignment, pledge, hypothecation or other
disposition of this Warrant or the Securities or any interest therein may be
made except (a) pursuant to an effective registration statement under the
Securities Act and any applicable Blue Sky Laws or (b) if the Company has been
furnished with both an opinion of counsel for the holder, which opinion and
counsel shall be reasonably satisfactory to the Company, to the effect that no
registration is required because of the availability of an exemption from
registration under the Securities Act and applicable Blue, Sky Laws, and
assurances that the transfer, sale, assignment, pledge, hypothecation or other
disposition will be made only in compliance with the conditions of any such
registration or exemption.

                   WARRANT TO PURCHASE SHARES OF COMMON STOCK

                                       OF

                                POPMAIL.COM, INC.

Warrant No.        December 1, 1999                       Bloomington, Minnesota

This certifies that, for value received, THE, HILLSTREET FUND, L.P., or its
successors or assigns ("Holder") is entitled to purchase from Popmail.com, Inc.,
a Minnesota corporation, (tile "Company") Two Hundred Thousand ($200,000) fully
paid and nonassessable shares (the "Shares") of the Company's Common Stock, $.01
par value (the "Common Stock"), at any time after the date hereof and prior to
December 1, 2004 (the "Warrant Exercise Period"), at an exercise price of $1.34
per share (tile "Exercise Price"), subject to adjustment as herein provided.

This Warrant is subject to the following provisions, terms and conditions:

         1. Exercise of Warrant. The rights represented by this Warrant may be
exercised by the Holder, in whole or in part (but not as to a fractional share
of Common Stock), by the surrender of this Warrant (properly endorsed, if
required, at the Company's principal office in Bloomington, Minnesota, or such
other office or agency of the Company as the Company may designate by notice in
writing to the Holder at the address of such Holder appearing on the books of
the Company at any time within the period above named), and upon payment to it
by certified check, bank draft or cash of the purchase price for such Shares.
The Company agrees that the Shares so purchased shall have and are deemed to be
issued to the Holder as the record owner of such Shares as of the close of
business on the date on which this Warrant shall leave been surrendered and
payment for such Shares as aforesaid. Certificates for the Shares of Common
Stock so purchased shall be delivered to the Holder within a reasonable time,
not exceeding ten (10) days, after the rights represented by this Warrant shall
have been so exercised, and, unless this Warrant has expired, a new Warrant
representing the number of Shares, if any, with respect to which this Warrant
shall not then have been exercised shall also be delivered to the Holder within
such time. The Company may require





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that any such new Warrant or any certificate for Shares purchased upon the
exercise hereof bear a legend substantially similar to that which is contained
on the face of this Warrant.

         2. Transferability of this Warrant. This Warrant is issued upon the
following terms, to which each Holder, consents and agrees:

                  (a) Until this Warrant is transferred on the books of the
Company, the Company will treat the Holder of this Warrant registered as such on
the books of the Company as the absolute owner hereof for all purposes without
being affected by any notice to the contrary.

                  (b) This Warrant may not be exercised and this Warrant and the
Shares underlying this Warrant shall not be transferable, except in compliance
with all applicable state and federal securities laws, regulations and orders,
and with all other applicable laws, regulations and orders.

                  (c) The Warrant may not be transferred, and the Shares may not
be transferred, without the Holder obtaining an opinion of counsel satisfactory
in form and substance to the Company's counsel stating that the proposed
transaction will not result in a prohibited transaction under the Securities Act
of 1933, as amended ("Securities Act"), and applicable Blue Sky laws. By
accepting this Warrant, the Holder agrees to act in accordance with any
conditions reasonably imposed on such transfer by such opinion of counsel.

                  (d) Neither this issuance of this Warrant nor the issuance of
the Shares underlying this Warrant have been registered under the Securities
Act.

         3. Certain Covenants of the Company. The Company covenants and agrees
that all Shares which may be issued upon the exercise of the rights represented
by this Warrant, upon issuance and full payment for the Shares so purchased,
will be duly authorized and issued, fully paid and nonassessable and free from
all taxes, liens and charges with respect to the issue hereof, except those that
may be created by or imposed upon the Holder or its property, and without
limiting the generality of the foregoing, the Company covenants and agrees that
it will from time to time take all such actions as may be requisite to assure
that the par value per share of the Common Stock is at all times equal to or
less than the effective purchase price per share of the Common Stock issuable
pursuant to this Warrant. The Company further covenants and agrees that during
the period within which the rights represented by this Warrant may be exercised,
the Company will at all times have authorized and reserved free of preemptive or
other rights for the exclusive purpose of issue upon exercise of the purchase
rights evidenced by this Warrant, a sufficient number of shares of its Common
Stock to provide for the exercise of the rights represented by this Warrant.

         4. Adjustment of Exercise Price and Number of Shares. The Exercise
Price and number of Shares are subject to the following adjustments:

                  (a) Adjustment of Exercise Price for Stock Dividend, Stock
Split or Stock Combination. In the event that (i) any dividends on any class of
stock of the Company payable in Common Stock or securities convertible into or
exercisable for Common Stock ("Common Stock



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Equivalents") shall be paid by the Company, (ii) the Company shall subdivide its
then outstanding shares of Common Stock into a greater number of shares, or
(iii) the Company shall combine its outstanding shares of Common Stock, by
reclassification or otherwise, then, in any such event, the Exercise Price in
effect immediately prior to such event shall (until adjusted again pursuant
hereto) be adjusted immediately after such event to a price (calculated to the
nearest full cent) determined by dividing (a) the number of shares of Common
Stock outstanding immediately prior to such event, multiplied by the then
existing Exercise Price, by (b) the total number of shares of Common Stock
outstanding immediately after such event, and the resulting quotient shall be
the adjusted Exercise Price per share. No adjustment of the Exercise Price shall
be made if the amount of such adjustment shall be less than $.05 per share, but
in such case any adjustment that would otherwise be required then to be made
shall be carried forward and shall be made at the time and together with the
next subsequent adjustment which, together with any adjustment or adjustments so
carried forward, shall amount to not less than $.05 per share.

                  (b) Adjustment of Number of Shares Purchasable on Exercise of
Warrants. Upon each adjustment of the Exercise Price pursuant to this Section,
the Holder shall thereafter (until another such adjustment) be entitled to
purchase at the adjusted Exercise Price the number of shares, calculated to the
nearest full share, obtained by multiplying the number of shares specified in
such Warrant (as adjusted as a result of all adjustments in the Exercise Price
in effect prior to such adjustment) by the Exercise Price in effect prior to
such adjustment and dividing the product so obtained by the adjusted Exercise
Price.

                  (c) Notice as to Adjustment. Upon any adjustment of the
Exercise Price and any increase or decrease in the number of shares of Common
Stock purchasable upon the exercise of the Warrant, then, and in each such case,
the Company within thirty (30) days there after shall give written notice
thereof, by first class mail, postage prepaid, addressed to each Holder as shown
on the books of the Company, which notice shall state the adjusted Exercise
Price and the increased or decreased number of shares purchasable upon the
exercise of the Warrants, and shall set forth in reasonable detail the method of
calculation and the facts upon which such calculation is based.

                  (d) Effect of Reorganization, Reclassification, Merger, etc.
If at any time while any Warrant is outstanding there should be any capital
reorganization of the capital stock of the Company (other than the issuance of
any shares of Common Stock in subdivision of outstanding shares of Common Stock
by reclassification or otherwise and other than a combination of shares provided
for in Section 4(a) hereof), or any consolidation or merger of the Company with
another corporation, or any sale, conveyance, lease or other transfer by the
Company of all or substantially all of its property to any other corporation,
which is effected in such a manner that the holders of Common Stock be entitled
to receive cash, stock, securities, or assets with respect to or in exchange for
Common Stock, then, as a part of such transaction, lawful provision shall be
made so that each Holder shall have the right thereafter to receive, upon the
exercise hereof, the number of shares of stock or other securities or property
of the Company, or of the successor corporation resulting from such
consolidation or merger, or of the corporation to which the property of the
Company has been sold, conveyed, leased or otherwise transferred, as the case
may be, which the Holder would have been entitled to receive upon such capital
reorganization, reclassification of capital stock, consolidation, merger, sale,
conveyance, lease or other transfer, if such Warrant had been exercised


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immediately prior to such capital reorganization reclassification of capital
stock, consolidation, merger, sale, conveyance, lease or other transfer. In any
such case, appropriate adjustments (as determined by the Board of Directors of
the Company) shall be made in the application of the provisions set forth in
this Warrant (including the adjustment of the Exercise Price and the number of
Shares issuable upon the exercise of the Warrants) to the end that the
provisions set forth herein shall herein shall thereafter be applicable, as near
as reasonably may be, in relation to any shares or other property thereafter
deliverable upon the exercise of the Warrants as if the Warrants had been
exercised immediately prior to such capital reorganization, reclassification of
capital stock, such consolidate on, merger, sale, conveyance, lease or other
transfer and the Warrant Holders had carried out the terms of the exchange as
provided for by such capital reorganization, consolidation or merger. The
Company shall not effect any such capital reorganization, consolidation merger
or transfer unless, upon or prior to the consummation thereof, the successor
corporation or the corporation to which the property of the Company has been
sold, conveyed, leased or otherwise transferred shall assume by written
instrument the obligation to deliver to each Holder such shares of stock,
securities, cash oi- property as in accordance with the foregoing provisions
such Holder shall be entitled to purchase.

         5. No Rights as Stockholders. This Warrant shall not entitle the Holder
as such to any voting rights or other rights as a stockholder of the Company.

         6.       Registration Rights.

                  (a) Piggyback Registration Rights. Provided that the Shares
are not then included in a Current registration statement of the Company, if the
Company, at any time before the fifth anniversary of the issuance of this
Warrant, shall file a registration statement with the Securities and Exchange
Commission ("SEC") under the Securities Act of 1933, as amended, for the purpose
of registering shares of Common stock for sale to the public, the Company shall
give to the Holder at least twenty (20) days advance written notice of its
intention to file such registration statement and Holder shall have the right to
have included in such registration statement such number of the Shares as it
shall designate to the Company within ten (10) days after the date of such
notice, provided that the number of Shares to be included in such registration
statement, when added to all the other shares to be included therein, does not
exceed the number of shares which the Company and its underwriters, if any,
reasonably fix for inclusion. If the number of Shares to be included in such
registration statement is less than the total number of Shares which the Holder
has requested to be included, then the Holder and other holders of shares of
Common Stock or other securities of the Company entitled to include shares of
Common Stock in such registration shall participate in the underwriting pro rata
based upon the total number of shares of Common Stock requested to be registered
by all of such holders. The Holder shall furnish the Company with such
information as may be required in connection with such registration statement
and will cooperate to cause such registration to become effective at the
earliest practicable time. If the shares to which such registration relates are
to be sold in an underwritten offering, the Holder, as a condition to the
inclusion of the shares in the registration statement, shall agree that its
Shares will be sold only as a part of such underwritten offering at the price
and upon the terms fixed by the Company and its underwriters, subject to the
right of the Holder to withdraw the Shares therefrom.



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         (b) Demand Registration Rights. On a one-time basis only, during the
three year period commencing two years after the date of this Warrant, upon
request by the Holder or Holders of a majority in interest of this Warrant, and
any Shares, the Company will promptly take all necessary steps to register or
qualify, under the 1933 Act and the securities laws of such states as the holder
may reasonably request, such number of Shares issued and to be issued upon
conversion of the Warrants and shares of common stock of the Company owned at
such time by such holders pursuant to the conversion of that certain $2,000.000
Senior Convertible Note issued as of the date of this Warrant requested by such
holders in their request to the Company. The Company shall keep effective and
maintain any registration, qualification, notification, or approval specified in
this section for such period as may be reasonably necessary for such Holder or
Holders of this Warrant and/or such Shares to dispose thereof and from time to
time shall amend or supplement the prospectus used in connection therewith to
the extent necessary in order to comply with applicable law.

         7. Governing Law. This Warrant shall be governed by and construed in
accordance with the laws of the State of Minnesota.

         8. Amendments and Waivers. The provisions of this Warrant may not be
amended, modified or supplemented, and waiver or consents to departures from the
provisions hereof may not be given, unless the (Company agrees in writing and
has obtained the written consent of the Holders.

         9. Notices. All notices or communications hereunder, except as herein
otherwise specifically provided, shall be in writing and if sent to the Holder
shall be mailed, delivered, or telefaxed and confirmed to the Holder at its
address set forth on the records of the Company; or if sent to the Company shall
be mailed, delivered, or telefaxed and confirmed to PopMail.com, Inc., 4801
West 81st Street, Suite 112, Bloomington, MN 55437 or to such other address as
the Company or the Holder shall notify the other as provided in this Section.

         IN WITNESS WHEREOF, Popmail.com, Inc. has caused this Warrant to be
signed by its duly authorized officer in the date set forth above.

                                         Popmail.com, Inc.


                                         /s/ Stephen D. King
                                         Stephen D. King
                                         Chairman of the Board








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                                SUBSCRIPTION FORM

         To be signed only upon exercise of Warrant.

         The undersigned, the holder of the within Warrant, hereby irrevocably
elects to exercise the purchase right represented by such Warrant for, and to
purchase thereunder,                 of the shares of Common Stock of
Popmail.com, Inc. (the "Shares") to which such Warrant relates and herewith
makes payment of $           therefor in cash, certified check or bank draft and
requests that a certificate evidencing the Shares be delivered to
                           , the address for whom is set forth below the
signature of the undersigned:

Dated:




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                                          (Signature)


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                                          (Address)













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                                 ASSIGNMENT FORM

         To be signed only upon authorized transfer of Warrant.

         FOR VALUE RECEIVED, the undersigned hereby sells, assigns, and
transfers unto                                      the right to purchase shares
of Common Stock of Popmail.com, Inc. to which the within Warrant relates and
appoints                         attorneys, to transfer said right on the books
of                     with full power of substitution in the premises.


Dated:
      -------------------------



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                                          (Signature)


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                                          (Address)