HEALTHEXTRAS INC
SC 13D, 1999-12-27
HEALTH SERVICES
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<PAGE> 1

                                  UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549
                                                           OMB APPROVAL
                                                      --------------------------
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                                                      Expires:August 31, 1999
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                                                      hours per response...14.90
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                                  SCHEDULE 13D
                    UNDER THE SECURITIES EXCHANGE ACT OF 1934
                                (AMENDMENT NO. __)*

                               HealthExtras, Inc.
- --------------------------------------------------------------------------------
                                (Name of Issuer)

                    Common Stock (par value, $.01 per share)
- --------------------------------------------------------------------------------
                         (Title of Class of Securities)

                                    422211102
- --------------------------------------------------------------------------------
                                 (CUSIP Number)

Highland Investments, LLC, c/o Thomas L. Blair, 2275 Research Blvd., Sixth
- --------------------------------------------------------------------------------
Floor, Rockville, MD 20850 [301-548-1000]
- --------------------------------------------------------------------------------
           (Name, Address and Telephone Number of Person Authorized to
                       Receive Notices and Communications)

                                December 17, 1999
- --------------------------------------------------------------------------------
             (Date of Event which Requires Filing of this Statement)

      If the filing person has  previously  filed a statement on Schedule 13G to
      report the  acquisition  that is the subject of this  Schedule 13D, and is
      filing  this  schedule  because  of  ss.ss.240.13d-1(e),  240.13d-1(f)  or
      240.13d-1(g), check the following box. |_|

      NOTE:  Schedules filed in paper format shall include a signed original and
      five copies of the schedule,  including all exhibits.  See ss.240.13d-7(b)
      for other parties to whom copies are to be sent.

      *The  remainder  of this cover  page  shall be filled out for a  reporting
      person's  initial filing on this form with respect to the subject class of
      securities,  and for any subsequent amendment containing information which
      would alter disclosures provided in a prior cover page.

      The information  required on the remainder of this cover page shall not be
      deemed to be "filed"  for the  purpose  of  Section  18 of the  Securities
      Exchange Act of 1934 ("Act") or otherwise  subject to the  liabilities  of
      that  section of the Act but shall be subject to all other  provisions  of
      the Act (however, see the Notes).



      POTENTIAL  PERSONS  WHO ARE TO RESPOND TO THE  COLLECTION  OF  INFORMATION
      CONTAINED  IN THIS  FORM  ARE NOT  REQUIRED  TO  RESPOND  UNLESS  THE FORM
      DISPLAYS A CURRENTLY VALID OMB CONTROL NUMBER.

SEC 1746 (2-98)

<PAGE> 2



CUSIP No.   422211102
- --------------------------------------------------------------------------------
      1.    Names of Reporting Persons
            I.R.S. Identification Nos. of Above Persons (entities only).

            Highland Investments, LLC                 IRS Id. No. 52-2171747
- --------------------------------------------------------------------------------
      2.    Check the Appropriate Box if a Member of a Group (See  Instructions)
            (a) |_|
            (b) |X|
- --------------------------------------------------------------------------------
      3.    SEC Use Only
- --------------------------------------------------------------------------------
      4.    Source of Funds (See Instructions)    00
- --------------------------------------------------------------------------------
      5.    Check if Disclosure of Legal Proceedings Is Required Pursuant to
            Items 2(d) or 2(e)   |_|
- --------------------------------------------------------------------------------
      6.    Citizenship or Place of Reorganization:     Maryland
- --------------------------------------------------------------------------------

Number of       7.    Sole Voting Power     17,680,000 shares
Shares Bene-          ----------------------------------------------------------
ficially Owned  8.    Shared Voting Power
by Each               ----------------------------------------------------------
Reporting       9.    Sole Dispositive Power     17,680,000 shares
Person With           ----------------------------------------------------------
               10.    Shared Dispositive Power
- --------------------------------------------------------------------------------
      11.   Aggregate Amount Beneficially Owned by Each Reporting Person
            17,680,000 shares
- --------------------------------------------------------------------------------
      12.   Check if the Aggregate Amount in Row (11) Excludes Certain Shares
            (See Instructions)   |_|
- --------------------------------------------------------------------------------
      13.   Percent of Class Represented by Amount in Row (11)     64.1%
- --------------------------------------------------------------------------------
      14.   Type of Reporting Person (See Instructions)
            00
- --------------------------------------------------------------------------------





<PAGE> 3


CUSIP No.   422211102
- --------------------------------------------------------------------------------
      1.    Names of Reporting Persons
            I.R.S. Identification Nos. of Above Persons (entities only).

            Principal Mutual Holding Company                IRS Id. No.
- --------------------------------------------------------------------------------
      2.    Check the Appropriate Box if a Member of a Group (See  Instructions)
            (a) |_|
            (b) |X|
- --------------------------------------------------------------------------------
      3.    SEC Use Only
- --------------------------------------------------------------------------------
      4.    Source of Funds (See Instructions)    00
- --------------------------------------------------------------------------------
      5.    Check if Disclosure of Legal Proceedings Is Required Pursuant to
            Items 2(d) or 2(e)   |_|
- --------------------------------------------------------------------------------
      6.    Citizenship or Place of Reorganization:     Iowa
- --------------------------------------------------------------------------------

Number of       7.    Sole Voting Power
Shares Bene-          ----------------------------------------------------------
ficially Owned  8.    Shared Voting Power    17,680,000 shares
by Each               ----------------------------------------------------------
Reporting       9.    Sole Dispositive Power
Person With           ----------------------------------------------------------
               10.    Shared Dispositive Power  17,680,000 shares
- --------------------------------------------------------------------------------
      11.   Aggregate Amount Beneficially Owned by Each Reporting Person
            17,680,000 shares
- --------------------------------------------------------------------------------
      12.   Check if the Aggregate Amount in Row (11) Excludes Certain Shares
            (See Instructions)   |_|
- --------------------------------------------------------------------------------
      13.   Percent of Class Represented by Amount in Row (11)     64.1%
- --------------------------------------------------------------------------------
      14.   Type of Reporting Person (See Instructions)
            CO; HC
- --------------------------------------------------------------------------------




<PAGE> 4


CUSIP No.   422211102
- --------------------------------------------------------------------------------
      1.    Names of Reporting Persons
            I.R.S. Identification Nos. of Above Persons (entities only).

            Thomas L. Blair                          IRS Id. No.  ###-##-####
- --------------------------------------------------------------------------------
      2.    Check the Appropriate Box if a Member of a Group (See  Instructions)
            (a) |_|
            (b) |X|
- --------------------------------------------------------------------------------
      3.    SEC Use Only
- --------------------------------------------------------------------------------
      4.    Source of Funds (See Instructions)    00
- --------------------------------------------------------------------------------
      5.    Check if Disclosure of Legal Proceedings Is Required Pursuant to
            Items 2(d) or 2(e)   |_|
- --------------------------------------------------------------------------------
      6.    Citizenship or Place of Reorganization:   USA
- --------------------------------------------------------------------------------

Number of       7.    Sole Voting Power
Shares Bene-          ----------------------------------------------------------
ficially Owned  8.    Shared Voting Power    17,680,000 shares
by Each               ----------------------------------------------------------
Reporting       9.    Sole Dispositive Power
Person With           ----------------------------------------------------------
               10.    Shared Dispositive Power  17,680,000 shares
- --------------------------------------------------------------------------------
      11.   Aggregate Amount Beneficially Owned by Each Reporting Person
            17,680,000 shares
- --------------------------------------------------------------------------------
      12.   Check if the Aggregate Amount in Row (11) Excludes Certain Shares
            (See Instructions)   |_|
- --------------------------------------------------------------------------------
      13.   Percent of Class Represented by Amount in Row (11)     64.1%
- --------------------------------------------------------------------------------
      14.   Type of Reporting Person (See Instructions)
            IN
- --------------------------------------------------------------------------------




<PAGE> 5



ITEM 1. SECURITY AND ISSUER

      This Schedule 13D (this "Schedule")  relates to the shares of common stock
(the  "Common  Stock"),  par value  $.01 per share,  of  HealthExtras,  Inc.,  a
corporation  organized under the laws of the State of Delaware (the  "Company").
The  principal  executive  offices of the Company  are located at 2275  Research
Boulevard, Seventh Floor, Rockville, Maryland 20850.


ITEM 2. IDENTITY AND BACKGROUND

(a)  Name - This  statement  is being  filed by  Highland  Investments,  LLC,  a
Maryland limited liability company ("Highland").

(b)  Residence  or  business   address  -  The  business   address  of  Highland
Investments,  LLC, which also serves as its principal  office,  is 2275 Research
Boulevard, Sixth Floor, Rockville, Maryland 20850.

(c)  Present occupation or employment:

(d)   Whether or not, during the last five years, such person has been convicted
      in  a  criminal  proceeding   (excluding  traffic  violations  or  similar
      misdemeanors) and, if so, give the dates,  nature of conviction,  name and
      location of court, any penalty imposed,  or other disposition of the case:
      No.

(e)   Whether or not,  during the last five years,  such person was a party to a
      civil  proceeding  of a  judicial  or  administrative  body  of  competent
      jurisdiction  and as a result of such  proceeding  was or is  subject to a
      judgment,  decree  or final  order  enjoining  future  violations  of,  or
      prohibiting  or  mandating   activities   subject  to,  federal  or  state
      securities  laws or finding any violation with respect to such laws;  and,
      if so,  identify and describe such  proceedings and summarize the terms of
      such judgment, decree or final order: No.

(f)   Citizenship - Maryland.

      The persons controlling Highland Investments, LLC are Thomas L. Blair, who
controls 49.5% of Highland  Investments  and Principal  Mutual Holding  Company,
which controls through an indirect  wholly-owned  subsidiary,  Principal Holding
Company,  50% of Highland  Investments.  The following  information  pertains to
Thomas L. Blair:

            (a)   This statement is also being filed by Thomas L. Blair.
            (b)   The  business  address  of  Thomas  L.  Blair is 2275 Research
                  Boulevard, Sixth Floor, Rockville, Maryland  20850
            (c)   Chairman  and Co-Chief  Executive  Officer of United  Payors &
                  United  Providers,  Inc.  (d) Whether or not,  during the last
                  five  years,  such  person  has been  convicted  in a criminal
                  proceeding    (excluding   traffic   violations   or   similar
                  misdemeanors)   and,  if  so,   give  the  dates,   nature  of
                  conviction,  name and location of court,  any penalty imposed,
                  or other disposition of the case: No.
            (e)   Whether or not, during the last five years,  such person was a
                  party to a civil  proceeding  of a judicial or  administrative
                  body  of  competent  jurisdiction  and  as a  result  of  such
                  proceeding  was or is subject to a  judgment,  decree or final
                  order  enjoining  future  violations  of,  or  prohibiting  or
                  mandating  activities  subject to, federal or state securities
                  laws or finding any violation with respect to such laws;  and,
                  if so,  identify and describe such  proceedings  and summarize
                  the terms of such judgment, decree or final order: No.
            (f)   USA.

      The following information pertains to Principal Mutual Holding Company:

            (a)   This statement is also being filed by Principal Mutual Holding
                  Company.
            (b)   The  business   address  of  Principal   Holding  Company  and
                  Principal  Mutual's  principal  business  address  is 711 High
                  Street, Des Moines, Iowa 50392.
            (c)   Insurance holding company.
            (d)   Whether or not,  during the last five  years,  such person has
                  been  convicted in a criminal  proceeding  (excluding  traffic
                  violations  or  similar  misdemeanors)  and,  if so,  give the
                  dates,

                                       -1-

<PAGE> 6



                  nature of conviction,  name and location of court, any penalty
                  imposed, or other disposition of the case: No.
            (e)   Whether or not, during the last five years,  such person was a
                  party to a civil  proceeding  of a judicial or  administrative
                  body  of  competent  jurisdiction  and  as a  result  of  such
                  proceeding  was or is subject to a  judgment,  decree or final
                  order  enjoining  future  violations  of,  or  prohibiting  or
                  mandating  activities  subject to, federal or state securities
                  laws or finding any violation with respect to such laws;  and,
                  if so,  identify and describe such  proceedings  and summarize
                  the terms of such judgment, decree or final order: No.
            (f)   Iowa.


      The following  information pertains to each executive officer and director
of Principal Mutual Holding Company:

            The  information  pertaining  to such  persons  is  incorporated  by
reference from Exhibit 99.1 attached.

ITEM 3. SOURCE AND AMOUNT OF FUNDS OR OTHER CONSIDERATION

      On May 27, 1999, Highland Investments,  LLC contributed  substantially all
of its assets to  HealthExtras,  LLC, a Delaware  limited  liability  company in
exchange for a 100% ownership interest in HealthExtras, LLC. Thomas L. Blair and
Principal  Mutual  Holding  Company  each had  invested  $5 million in  Highland
Investments, LLC.

      On December  17,  HealthExtras,  LLC merged  into  HealthExtras,  Inc.,  a
corporation  it had  formed in order to change  its  corporate  identity  from a
Delaware  limited  liability  company to a Delaware  corporation and to effect a
public  offering  of the Common  Stock.  In such  merger,  Highland  Investments
received  17,680,000  shares of HealthExtras,  Inc. Common Stock in exchange for
its membership  interest in  HealthExtras,  LLC., which at that time represented
ownership of 80% of HealthExtras, LLC.

ITEM 4. PURPOSE OF TRANSACTION

      State the purpose or  purposes of the  acquisition  of  securities  of the
issuer.  Describe any plans or proposals  which the  reporting  persons may have
which relate to or would result in:

(a)   The acquisition  by any  person of additional securities of the issuer, or
      the disposition of securities of the issuer:

(b)   An extraordinary corporate transaction,  such as a merger,  reorganization
      or liquidation, involving the issuer or any of its subsidiaries;

(c)   A sale or transfer of a material  amount of assets of the issuer or any of
      its subsidiaries;

(d)   Any change in the present  board of directors or management of the issuer,
      including any plans or proposals to change the number or term of directors
      or to fill any existing vacancies on the board;

(e)   Any material  change in  the present  capitalization or dividend policy of
      the issuer;

(f)   Any other material change in the issuer's business or corporate  structure
      including  but not  limited to, if the issuer is a  registered  closed-end
      investment  company,  any plans or  proposals  to make any  changes in its
      investment  policy  for  which a vote is  required  by  Section  13 of the
      Investment Company Act of 1940;

(g)   Changes  in the  issuer's  charter,  bylaws or  instruments  corresponding
      thereto or other  actions which may impede the  acquisition  of control of
      the issuer by any person;

(h)   Causing a class of securities of the issuer to be delisted from a national
      securities  exchange  or to  cease to be  authorized  to be  quoted  in an
      inter-dealer   quotation  system  of  a  registered   national  securities
      association;

(i)   A  class  of  equity  securities  of  the  issuer  becoming  eligible  for
      termination of registration pursuant to Section 12(g)(4) of the Act; or


                                       -2-

<PAGE> 7



(j)   Any action similar to any of those enumerated above.

      The Reporting  Persons made  investments in predecessors to the Company as
discussed in Item 3 above.  As the owner of 64.1% of the  Company's  outstanding
Common  Stock,  the  Reporting  Person may be considered to control the Company.
Except as set forth in this Item 4  (including  the matters  described in Item 6
below which are incorporated in this Item 4 by reference), the Reporting Persons
have no present plans or proposals that relate to or that would result in any of
the actions  specified  in clauses (a) through (j) of Item 4 of Schedule  13D of
the Exchange Act.  However,  the Reporting Persons reserve the right to take any
action  regarding  the  management  of the  affairs of the  Company as they deem
appropriate, consistent with their legal obligations. In addition, the Reporting
Persons may review, as appropriate,  their investment in the Company.  Depending
upon future  evaluations of the business prospects of the Company and upon other
developments,  including,  but not limited to,  general  economic  and  business
conditions and stock market conditions, the Reporting Persons may retain or from
time to time  increase  their  holdings  or dispose of all or a portion of their
holdings,  subject to any applicable legal and contractual restrictions on their
ability to do so.


ITEM 5. INTEREST IN SECURITIES OF THE ISSUER

(a)   Highland Investments, LLC is the record and beneficial owner of 17,680,000
      shares of Common  Stock,  which based on  calculations  made in accordance
      with Rule 13d-3(d) of the Exchange Act represents 64.1% of the outstanding
      shares of Common Stock.

      In  addition,  by virtue of their  controlling  relationship  to  Highland
      Investments, as described in Item 2, each of Thomas L. Blair and Principal
      Mutual Holding  Company may be deemed to  beneficially  own the 17,680,000
      shares of Common Stock owned by Highland Investments, 64.1% of outstanding
      shares of Common Stock.

(b)   Highland Investments has sole power to vote or direct the vote with regard
      to 17,680,000 shares of Common Stock. Thomas L. Blair and Principal Mutual
      Holding Company as the  controlling  persons able to direct the actions of
      Highland  Investments  may be  deemed to share the power to vote or direct
      the vote with regard to the shares.

(c)   Except as set forth  herein,  none of the  persons  named in  response  to
      paragraph  (a) have  affected any  transactions  in shares of Common Stock
      during the past sixty (60) days.

(d)   Each of the  Reporting  Persons  affirms  that no  person  other  than the
      Reporting  Persons  has the right to  receive  or the power to direct  the
      receipt of dividends from, or the proceeds from the sale of, the shares of
      Common Stock, owned by the Reporting Persons.

(e)   Not applicable.


ITEM 6. CONTRACTS, ARRANGEMENTS, UNDERSTANDINGS OR RELATIONSHIPS WITH RESPECT TO
        SECURITIES OF THE ISSUER.

      Describe any  contracts,  arrangements,  understandings  or  relationships
(legal or otherwise)  among the persons named in Item 2 and between such persons
and any person with respect to any  securities of the issuer,  including but not
limited to transfer or voting of any of the  securities,  finder's  fees,  joint
ventures,  loan or option  arrangements,  put or calls,  guarantees  of profits,
division of profits or loss, or the giving or withholding of proxies, naming the
persons with whom such contracts, arrangements,  understandings or relationships
have been entered into.  Include such information for any of the securities that
are pledged or otherwise  subject to a contingency the occurrence of which would
give another person voting power or investment power over such securities except
that  disclosure of standard  default and similar  provisions  contained in loan
agreements need not be included.

      The  matters  set  forth  in Item 2 are  incorporated  in  this  Item 6 by
reference as if fully set forth herein.

      In connection with the Company's public offering of common stock, Highland
Investments has agreed pursuant to a "lock-up" agreement that it will not offer,
sell,  contract to sell, pledge,  grant any option to sell, or otherwise dispose
of, directly or indirectly, any shares of common stock or securities convertible
into or exercisable or exchangeable for

                                       -3-

<PAGE> 8



common stock for a period of 180 days after  December 17, 1999.  Warburg  Dillon
Read LLC may release the shares subject to this lock-up agreement in whole or in
part at anytime.

      On May 27, 1999, HealthExtras, which was then a Maryland limited liability
company,  contributed  substantially  all of its assets to HealthExtras,  LLC, a
Delaware limited liability company, in exchange for a 100% ownership interest in
HealthExtras,  LLC. Immediately  thereafter,  Capital Z Healthcare Holding Corp.
("CZHH")  invested  $5 million  in  HealthExtras,  Inc.  in  exchange  for a 20%
ownership interest. In connection with this transaction,  HealthExtras agreed to
indemnify  CZHH  for  any  losses  arising  from  any  breach  of  HealthExtras'
representations or warranties or its failure to give effect to the restructuring
as contemplated by its Amended and Restated Limited Liability Company Agreement.
CZHH serves  only as a vehicle for its sole  stockholder,  Health  Partners,  to
invest in HealthExtras and does not conduct any other operations.

      HealthExtras,   Inc.,   HealthExtras,   LLC  and  CZHH   entered   into  a
Reorganization  Agreement  dated as of December  9, 1999  pursuant to which CZHH
merged into  HealthExtras,  Inc. on December  17, 1999.  Immediately  after that
merger,  HealthExtras,  LCC merged into HealthExtras,  Inc. As a result of these
mergers, Health Partners, the sole stockholder of CZHH, received Common Stock in
HealthExtras,  Inc. representing the same proportionate ownership position which
CZHH had in HealthExtras,  LLC and Highland Investments received Common Stock in
HealthExtras,  Inc. representing the same proportionate ownership position which
it  had  in  HealthExtras,  LLC.  We  refer  to  the  matters  covered  by  this
Reorganization Agreement as the reorganization.

      In  connection  with  the  reorganization,  HealthExtras,  Inc.,  Highland
Investments, LLC and Health Partners entered into a Stockholders Agreement dated
as  of  December  9,  1999.  This  Stockholders  Agreement  contains  provisions
regarding  registration  rights, the composition of the Board of Directors,  and
tag-along  rights,  rights of first offer and preemptive  rights with respect to
certain sales of Common Stock.


REGISTRATION RIGHTS

      Health  Partners  and  Highland  Investments  have  been  granted  certain
registration rights with respect to shares of HealthExtras' Common Stock held by
them and their assigns. The Stockholders  Agreement provides for an aggregate of
four demand  registration  statements under the Securities Act of 1933 beginning
180 days after December 13, 1999.  Health Partners or Highland  Investments each
may require that HealthExtras file two of those demand registration  statements,
subject  to certain  conditions.  If Health  Partners  or  Highland  Investments
exercises a demand  registration  right,  the other also can  participate in the
offering on a proportionate basis to their respective ownership positions. These
stockholders are also entitled to require  HealthExtras to register their shares
of  HealthExtras'  Common  Stock on a  registration  statement  on Form S-3 once
HealthExtras   is  eligible  to  use  a  Form  S-3  in   connection   with  such
registrations.   In  addition,   these  stockholders  are  entitled  to  require
HealthExtras  to include  their shares of  HealthExtras'  Common Stock in future
registration  statements  HealthExtras  files under the  Securities  Act,  often
referred  to as  "piggyback"  registration  rights.  However,  holders  of these
registration  rights will be restricted from  exercising  those rights until 180
days after the date of this  prospectus  and, under certain  circumstances,  for
agreed-upon  periods  after the filing of  subsequent  registration  statements.
Also,  the shares  required  to be  included  in a  registration  relating to an
underwritten  offering generally are subject to underwriter cut back provisions.
Registration  of shares of  Common  Stock  pursuant  to the  exercise  of demand
registration  rights,  piggyback  registration  rights or Form S-3  registration
rights would result in the shares covered by those registrations becoming freely
tradable  without  restriction  under the  Securities Act  immediately  upon the
effectiveness   of  the   registration,   subject  to  any  lock-up   agreements
HealthExtras  has with these  stockholders.  HealthExtras  is  required  to bear
substantially all registration  expenses in connection with the  above-described
registrations,  except for underwriting discounts, income and transfer taxes, if
any,  selling  expenses  and the fees and expenses of counsel  representing  the
holders  of  the  registrable   securities.   These   registration   rights  are
transferable in certain circumstances and may be amended or waived only with the
consent of the affected party.

DIRECTORS

      Under  the  Stockholders   Agreement,   Highland  Investments  and  Health
Partners, the sole stockholder of CZHH, were granted certain rights to designate
persons for election as  HealthExtras'  Directors.  The  Stockholders  Agreement
provides that:


                                       -4-

<PAGE> 9



      Highland   Investments   may   designate   five  people  for  election  as
HealthExtras'   Directors  if  Highland   Investments   owns  at  least  40%  of
HealthExtras'   outstanding   Common   Stock;   three  people  for  election  as
HealthExtras'   Directors  if  Highland   Investments   owns  at  least  25%  of
HealthExtras' outstanding Common Stock; two people for election as HealthExtras'
Directors if Highland Investments owns at least 10% of HealthExtras' outstanding
Common Stock; and one person for election as HealthExtras'  Director if Highland
Investments owns at least 5% of HealthExtras' outstanding Common Stock.

      Health  Partners may  designate  two people for election as  HealthExtras'
Directors  if Health  Partners  owns at least 10% of  HealthExtras'  outstanding
Common Stock;  and one person for election as  HealthExtras'  Director if Health
Partners owns at least 5% of HealthExtras' outstanding Common Stock.

      Highland  Investments and Health Partners also may be entitled to increase
the number of Directors that they may designate for election if the total number
of directors is increased.  This would maintain Highland Investments' and Health
Partners' control of HealthExtras' Board of Directors,  even if the total number
of directors increases.

      Under  the  Stockholders  Agreement,   five  representatives  of  Highland
Investments, initially Thomas L. Blair, David T. Blair, Thomas J. Graf, Julia M.
Lawler, and Karen E. Shaff, and two  representatives of Health Partners,  Julian
A.L. Allen and Paul H. Warren, are HealthExtras, Inc.'s Directors.

RIGHTS OF FIRST OFFER AND TAG-ALONG RIGHTS

      The Stockholders  Agreement provides that Highland  Investments and Health
Partners must give notice to  HealthExtras  and to each other if either proposes
to transfer Common Stock  aggregating more than 10% of HealthExtras  outstanding
Common  Stock  to a single  person  or group  who is not a family  member  (if a
natural  person),  an  affiliate  (if an  entity),  or an employee or manager of
HealthExtras.

      Upon receipt of notice, the non-transferring  stockholder (either Highland
Investments  or Health  Partners)  may elect to  participate  in the transfer by
delivering  written  notice  to the  transferring  stockholder.  This  right  to
participate  in the  transfer is called  "tag-along"  rights.  If a  stockholder
elects to  participate  in the transfer,  the aggregate  sales proceeds shall be
divided   proportionally   according  to  the  electing  stockholder's  and  the
transferring  stockholder's  respective shares of the proceeds of a hypothetical
liquidation.  In order to calculate the proceeds of a hypothetical  liquidation,
the value of  HealthExtras  will be  implied by the  transferring  stockholder's
proposed sales price.

      Alternately,  upon receipt of notice,  HealthExtras  may elect to purchase
all of the  shares  that the  transferring  shareholder  proposes  to  sell.  If
HealthExtras  does not  elect  to  purchase  the  shares,  the  non-transferring
shareholder  (either  Highland  Investments  or  Health  Partners)  may elect to
purchase all of the shares offered.  This right to preempt a sale, and therefore
a possible change in control,  by purchasing the shares offered is called "first
offer right." If  HealthExtras  exercises  its first offer rights,  HealthExtras
must  purchase all of the shares  offered upon the same terms and  conditions as
originally  offered.  If the  non-transferring  shareholder  exercises its first
offer rights,  it may purchase a pro rata portion of the shares offered upon the
same terms and conditions as originally offered.

      These tag-along and first offer rights and obligations would apply also to
controlling persons of Health Partners and Highland  Investments,  to whom those
entities might distribute shares of HealthExtras' Common Stock.

PREEMPTIVE RIGHTS

      The Stockholders Agreement prohibits HealthExtras from offering its Common
Stock  for  sale  other  than  in a  public  offering,  in  connection  with  an
acquisition  or  pursuant  to  employee  benefit  plan  or  arrangement,  unless
HealthExtras  first  offers  such  shares to  Highland  Investments  and  Health
Partners.  The  preemptive  offer  must be in  writing,  on the same  terms  and
conditions as the offering and at the equivalent price, and must enable Highland
Investments  and Health Partners to retain the same  proportionate  ownership of
Common Stock that it holds prior to the offering. This provision allows Highland
Investments  and  Health  Partners  to retain  control of  HealthExtras  even if
HealthExtras decides to privately issue additional Common Stock at a later date.


                                       -5-

<PAGE> 10


AFFILIATE TRANSACTIONS

      The Stockholders Agreement also provides that HealthExtras will not engage
in transactions with affiliates other than on terms no less favorable than could
be  obtained  on an  arms-length  basis or which are  approved  by a majority of
directors  who are  independent  of the  affiliate.  Further,  the  Stockholders
Agreement  requires  that  prior  to any  merger  or  purchase  or sale of stock
transaction with an affiliate,  where the value of such  transaction  exceeds $1
million,   HealthExtras  must  obtain  a  fairness  opinion  from  a  nationally
recognized investment bank.


ITEM 7. MATERIAL TO BE FILED AS EXHIBITS

      The  following  shall be filed as exhibits:  copies of written  agreements
relating to the filing of joint  acquisition  statements  as required by Section
240.13d-1(k)  and copies of all  written  agreements,  contracts,  arrangements,
understandings,  plans or  proposals  relating to (1) the  borrowing of funds to
finance the  acquisition  as disclosed in Item 3; (2) the  acquisition of issuer
control, liquidation, sale of assets, merger, or change in business or corporate
structure  or any other  matter as  disclosed in Item 4; and (3) the transfer or
voting of the securities,  finder's fees, joint ventures,  options, puts, calls,
guarantees  of loans,  guarantees  against  loss or of profit,  or the giving or
withholding of any Proxy as disclosed in Item 6.

Exhibits.

      2.1   Form of Reorganization  Agreement by and among  HealthExtras,  Inc.,
            HealthExtras,  LLC, and CZHH is incorporated by reference as Exhibit
            2.1 to Registration  Statement on Form S-1, No. 333-83761,  filed on
            September 21, 1999.

      4.2   Form of  Stockholders  Agreement by and among Highland  Investments,
            LLC, HealthExtras, LLC, HealthExtras, Inc., Principal Mutual Holding
            Company,  Thomas L.  Blair,  Health  Partners,  Capital Z  Financial
            Services Fund, II, L.P.,  Capital Z Financial Services Private Fund,
            II, L.P., Capital Z Partners,  Ltd., and Capital Z Management,  LLC.
            is   incorporated  by  reference  as  Exhibit  4.2  to  Registration
            Statement on Form S-1, No. 333-83761, filed on September 21, 1999.

      10.10 Form of Registration  Rights Agreement by and among Health Partners,
            Highland Investments, LLC and HealthExtras,  Inc. is incorporated by
            reference as Exhibit  10.10 to  Registration  Statement on Form S-1,
            No. 333-83761, filed on September 21, 1999.

      99.1  Information regarding  executive officers and directors of Principal
            Mutual Holding Company.

      99.2  Lock-up  Agreement by  Highland Investments, LLC with Warburg Dillon
            Read LLC.


                                       -6-

<PAGE> 11



SIGNATURE

      After  reasonable  inquiry and to the best of my knowledge  and belief,  I
certify that the information  set forth in this statement is true,  complete and
correct.


HIGHLAND INVESTMENTS, LLC


By: /s/ Thomas L. Blair
    -----------------------------------------
Thomas L. Blair, Administrative Member



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



/s/ Thomas L. Blair
- ---------------------------------------
Thomas L. Blair, Individually





PRINCIPAL MUTUAL HOLDING COMPANY


By:/s/ Thomas J. Graf
   -------------------------------------
Thomas J. Graf, Senior Vice President



December 27, 1999
- ----------------------------------------
Date



      The original  statement shall be signed by each person on whose behalf the
statement is filed or his authorized representative.  If the statement is signed
on behalf of a person by his authorized  representative (other than an executive
officer  or  general   partner  of  this   filing   person),   evidence  of  the
representative's  authority to sign on behalf of such person shall be filed with
the  statement,  provided,  however,  that a power of attorney  for this purpose
which is already on file with the Commission may be  incorporated  by reference.
The name and any title of each person who signs the statement  shall be typed or
printed beneath his signature.


ATTENTION: INTENTIONAL  MISSTATEMENTS  OR  OMISSIONS  OF FACT CONSTITUTE FEDERAL
CRIMINAL VIOLATIONS (SEE 18 U.S.C. 1001)

                                       -7-

<PAGE> 1



                                  EXHIBIT 99.1
                                  ------------

            DIRECTORS AND EXECUTIVE OFFICERS OF THE REPORTING PERSONS
            ---------------------------------------------------------

                        PRINCIPAL MUTUAL HOLDING COMPANY,
                        ---------------------------------
                        PRINCIPAL FINANCIAL GROUP, INC.,
                        --------------------------------
                       PRINCIPAL FINANCIAL SERVICES, INC.,
                       -----------------------------------
                                       AND
                                       ---
                        PRINCIPAL LIFE INSURANCE COMPANY
                        --------------------------------



DIRECTORS:


Betsy J. Bernard
Executive Vice President - Retail Markets
U S WEST
1801 California Street, 52nd Floor
Denver, CO  80202

Jocelyn Carter-Miller
Corporate Vice President and
Chief Marketing Officer
Motorola, Inc.
1000 Corporate Drive, Suite 700
Fort Lauderdale, FL  33334

David J. Drury
Chairman and Chief Executive Officer
Principal Financial Group
711 High Street
Des Moines, IA  50392-0100

Daniel Gelatt
President
NMT Corporation
Post Office Box 2287
La Crosse, WI  54602-2287

J. Barry Griswell
President
Principal Financial Group
711 High Street
Des Moines, IA 50392-0100

G. David Hurd
Principal Financial Group
711 High Street
Des Moines, IA  50392-0100

Charles S. Johnson
Executive Vice President
DuPont
400 Locust
Suite 700 Capital Square
Des Moines, IA  50309


<PAGE> 2



William T. Kerr                              Elizabeth E. Tallett
Chairman and Chief Executive Officer         President and Chief Executive
Meredith Corporation                          Officer
1716 Locust Street                           Dioscor Inc.
Des Moines, IA  50309-3023                   48 Federal Twist Road
                                             Stockton, NJ  08559

Lee Liu
Chairman of the Board
Alliant Energy Corporation
Post Office Box 351
Cedar Rapids, IA  52406

Victor H. Loewenstein
Partner and Member of the Board
Egon Zehnder International
Cours de Rive #10
CH-1204 Geneva, Switzerland

Ronald D. Pearson
Chairman, President and Chief Executive Officer
Hy-Vee, Inc.
5820 Westown Parkway
West Des Moines, IA  50266

Federico F. Pena
Senior Advisor
Vestar Capital Partners
1225 17th Street, Suite 1660
Denver, CO  80202

John R. Price
Managing Director
The Chase Manhattan Corporation
270 Park Avenue - 44th Floor
New York, NY  10017

Donald M. Stewart
Senior Program Officer and
Special Advisor to the President
Carnegie Corporation of New York
437 Madison Avenue
New York, NY  10022


<PAGE> 3


Fred W. Weitz
President and Chief Executive Officer
Essex Meadows, Inc.
800 Second Avenue, Suite 150
Des Moines, IA  50309


The principal business address for all Executive Officers is 711 High Street,
Des Moines, Iowa 50392.

EXECUTIVE OFFICERS:

David J. Drury                               Robb B. Hill
Chairman and Chief Executive Officer         Senior Vice President

J. Barry Griswell                            Ellen Z. Lamale
President                                    Senior Vice President and Chief
                                              Actuary

John E. Aschenbrenner                        Mary A. O'Keefe
Senior Vice President                        Senior Vice President

Paul F. Bognanno                             Richard L. Prey
Senior Vice President                        Senior Vice President

Gary M. Cain                                 Karen E. Shaff
Senior Vice President                        Senior Vice President and Deputy
                                              General Counsel

C. Robert Duncan                             Robert A. Slepicka
Senior Vice President                        Senior Vice President

Dennis P. Francis                            Norman R. Sorensen
Senior Vice President                        Senior Vice President

Michael H. Gersie                            Carl C. Williams
Senior Vice President                        Senior Vice President and Chief
                                              Information Officer

Thomas J. Graf                               Larry D. Zimpleman
Senior Vice President                        Senior Vice President

<PAGE> 4


                            PRINCIPAL HOLDING COMPANY
                            -------------------------


The principal  business  address for all  Directors  and  Executive  Officers of
Principal Holding Company is 711 High Street, Des Moines, Iowa 50392.

DIRECTORS:


David J. Drury
Chairman

John E. Aschenbrenner                        J. Barry Griswell

Dennis P. Francis                            Ellen Z. Lamale

Michael H. Gersie                            Julia M. Lawler

Thomas J. Graf                               Richard L. Prey


EXECUTIVE OFFICERS:


David J. Drury                               Mary A. O'Keefe
Chairman and Chief Executive Officer         Senior Vice President

J. Barry Griswell                            Richard L. Prey
President                                    Senior Vice President

John E. Aschenbrenner                        Robert A. Slepicka
Senior Vice President                        Senior Vice President

Paul F. Bognanno                             Norman R. Sorensen
Senior Vice President                        Senior Vice President

C. Robert Duncan                             Carl C. Williams
Senior Vice President                        Senior Vice President and Chief
                                             Information Officer

Dennis P. Francis                            Douglas C. Cunningham
Senior Vice President                        Vice President and Controller

Michael H. Gersie                            Joyce N. Hoffman
Senior Vice President                        Vice President and Corporate
                                             Secretary

Thomas J. Graf                               Craig L. Bassett
Senior Vice President                        Treasurer

Robb B. Hill
Senior Vice President


<PAGE> 1



                               HealthExtras, Inc.
                     Initial Public Offering of Common Stock
                     ---------------------------------------



                                         September 30, 1999




Warburg Dillon Read LLC
299 Park Avenue
New York, New York 10171

Ladies and Gentlemen:

            This  letter  is  being  delivered  to you in  connection  with  the
proposed  Underwriting   Agreement  (the  "Underwriting   Agreement"),   between
HealthExtras,  Inc., a Delaware corporation (the "Company"),  and each of you as
Underwriters  with respect to an  underwritten  public offering of Common Stock,
$0.01 par value (the "Common Stock"), of the Company.

            In order to induce you to enter into the Underwriting Agreement, the
undersigned  will not,  without the prior written consent of Warburg Dillon Read
LLC, offer, sell,  contract to sell, pledge or otherwise dispose of, or file (or
participate in the filing of) a  registration  statement with the Securities and
Exchange  Commission  in respect of, or establish  or increase a put  equivalent
position or liquidate or decrease a call equivalent  position within the meaning
of Section 16 of the Securities Exchange Act of 1934, as amended,  and the rules
and regulations of the Securities and Exchange Commission promulgated thereunder
with  respect to, any shares of capital  stock of the Company or any  securities
convertible  into or exercisable  or  exchangeable  for such capital  stock,  or
publicly announce an intention to effect any such  transaction,  for a period of
180 days after the date of execution of the Underwriting Agreement.

            If for any reason the  Underwriting  Agreement  shall be  terminated
prior to the  Closing  Date (as  defined  in the  Underwriting  Agreement),  the
agreement set forth above shall likewise be terminated.

                                    Yours very truly,


                                    /s/ Thomas L. Blair
                                    -------------------------------
                                    Name:  T. L. Blair
                                    Title: Administrative Member
                                           Highland Investments LLC



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