Document:

EX-4.15 Letter dated October 17, 2008

Exhibit 4.15

LADENBURG THALMANN & CO. INC.

4400 Biscayne Blvd., 14th Floor

Miami, Florida 33137

Liberator Medical Holdings, Inc.

2979 South East Gran Park Way

Stuart, Florida 34997

Attention: Mark A. Libratore, President

October 17, 2008

Re:     Waiver and Amendment under May 2008 Warrants

Dear Mark:

     Reference is hereby made to the Warrant to Purchase Common Stock (the “May 2008
Warrants”) issued by Liberator Medical Holdings, Inc. (the “Company”) on May 22, 2008
to Ladenburg Thalmann & Co. Inc. (“Ladenburg”) as compensation under the Investment Banking
Agreement, dated as of March 10, 2008, as supplemented by the letter agreement dated May 22, 2008,
between the Company and Ladenburg, in connection with the transactions consummated under the
Securities Purchase Agreement, dated as of May 22, 2008 (the “May 2008 SPA”), by and among
the Company, Liberator Medical Supply, Inc., as guarantor (“Liberator Supply”), and
Millennium Partners, L.P. (“Investor”), as purchaser, of the securities issued under the
May 2008 SPA.

     In connection with the Securities Purchase Agreement to be entered into on the date hereof by
and among the Company, as issuer, Liberator Supply and Liberator Health and Education Services,
Inc., as guarantors, and one or more purchasers, including the Investor (collectively, the
“Purchasers”), for the sale and issuance by the Company and the purchase by the Purchasers
of 3% Senior Convertible Notes due 2010 (the “New Notes”) and warrants to purchase common
stock of the Company (including warrants that may be issued as compensation to Ladenburg as
placement agent for the Company in connection with said transaction, the “New Warrants”),
Ladenburg hereby confirms and agrees, solely for the benefit of the Company, as follows:

	 	1.	 	Ladenburg directly and beneficially
holds all of the May 2008 Warrants; and
	 
	 	2.	 	Ladenburg hereby, in its capacity as
holder of the May 2008 Warrants, (i) waives any right it
may have to have the Exercise Price (as defined in the May
2008 Warrants) adjusted in connection with the issuance,
conversion or exercise of the New Notes (including any
replacements thereof), the New Warrants (including any
replacements thereof) or the 3% Senior Convertible Note due
2010 of the
Company (including any replacements thereof) originally
issued to Millennium pursuant to the May 2008 SPA, as
amended and restated on the date hereof, and (ii)
irrevocably and permanently waives its rights under Section
4(b) of the May 2008 Warrants and agrees that the May 2008
Warrants (and any replacements thereof) shall be amended so
as to delete Section 4(b) therefrom in its entirety.

     This letter shall be governed by the laws of the State of New York.
Yours truly,

	 	 	 	 	 
	 	LADENBURG THALMANN & CO. INC.

 	 
	 	By:  	/s/ Barry E. Steiner
 	 
	 	 	Name:  	Barry E. Steiner 	 
	 	 	Title:  	Managing DirectorEX-4.16 Letter dated October 17, 2008

Exhibit 4.16

MILLENNIUM PARTNERS, L.P.

c/o Millennium Management LLC

666 Fifth Avenue, 8th Floor

New York, New York 10103

Liberator Medical Holdings, Inc.

2979 South East Gran Park Way

Stuart, Florida 34997

Attention: Mark A. Libratore, President

October 17, 2008

Re:     Waivers, Amendment and Restatement under May 2008 Warrants and Notes

Dear Mark:

     Reference is hereby made to the 3% Senior Convertible Notes due 2010 (the “May 2008
Notes”) and the Warrant to Purchase Common Stock (the “May 2008 Warrants”) issued by
Liberator Medical Holdings, Inc. (the “Company”) on May 22, 2008 pursuant to the Securities
Purchase Agreement, dated as of May 22, 2008 (the “May 2008 SPA”), by and among the
Company, Liberator Medical Supply, Inc., as guarantor (“Liberator Supply”), and Millennium
Partners, L.P. (“Investor”), as sole purchaser of the May 2008 Notes and the May 2008
Warrants.

     In connection with the Securities Purchase Agreement to be entered into on the date hereof by
and among the Company, as issuer, Liberator Supply and Liberator Health and Education Services,
Inc., as guarantors, and one or more purchasers, including the Investor (collectively, the
“Purchasers”), for the sale and issuance by the Company and the purchase by the Purchasers
of 3% Senior Convertible Notes due 2010 (the “New Notes”) and warrants to purchase common
stock of the Company (including warrants that may be issued as compensation to the placement agent
for the Company in connection with said transaction, the “New Warrants”), Investor hereby
confirms and agrees, solely for the benefit of the Company, as follows:

	 	1.	 	Investor directly and beneficially holds all of the May
2008 Notes and the May 2008 Warrants issued pursuant to the May 2008 SPA;
	 
	 	2.	 	Investor hereby, in its capacity as holder of the May
2008 Notes (as the same may be amended and restated pursuant to paragraph 5
below), waives any right it may have to have the Conversion Price (as
defined in the May 2008 Notes) adjusted in connection with the issuance,
conversion or exercise of the New Notes (including any replacements thereof
issued in accordance with the terms of Section 18 thereof as in effect on
the date hereof) or the New Warrants (including any replacements thereof
issued in accordance with the terms of Section 7 thereof as in effect on
the date hereof);

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	 	3.	 	Investor hereby, in its capacity as holder of the May
2008 Warrants, waives any right it may have to have the Exercise Price (as
defined in the May 2008 Warrants) adjusted in connection with the issuance,
conversion or exercise of the New Notes (including any replacements thereof
issued in accordance with the terms of Section 18 thereof as in effect on
the date hereof) or the New Warrants (including any replacements thereof
issued in accordance with the terms of Section 7 thereof as in effect on
the date hereof);
	 
	 	4.	 	Investor hereby, in its capacity as holder of the May
2008 Warrants, irrevocably and permanently waives its rights under Section
4(b) of the May 2008 Warrants and agrees that the May 2008 Warrants (and
any replacements thereof) shall be amended so as to delete Section 4(b)
therefrom in its entirety; and
	 
	 	5.	 	Investor is surrendering the May 2008 Notes issued to
it on May 22, 2008 for cancellation in exchange for the issuance by the
Company to Investor of a amended and restated 3% Senior Convertible Note
due 2010 in the form attached hereto as Exhibit A.

     This letter shall be governed by the laws of the State of New York.

	 	 	 	 	 
	 	Yours truly,

MILLENNIUM PARTNERS, L.P.

 	 
	 	By:  	Millennium Management LLC, its Managing Partner
 	 
	 	 	 
	 
	 	By:  	/s/ Terry Feeney
 	 
	 	 	Name:  	Terry Feeney 	 
	 	 	Title:  	Chief Operating Officer 	 
	 

ACKNOWLEDGED AND AGREED TO:

LIBERATOR MEDICAL HOLDINGS, INC.

	 	 	 	 	 
	 	 
	By:  	/s/ Mark A. Libratore
 	 
	 	 	Name:  	Mark A. Libratore 	 
	 	 	Title:  	President 	 
	 

      

      

      

Signature Page to

Letter re: Waivers, Amendment and Restatement under May 2008 Warrants and Notes

2EX-4.17 Subordination Agreement

Exhibit 4.17

EXECUTION COPY

SUBORDINATION AGREEMENT

     SUBORDINATION AGREEMENT, dated as of October 17, 2008 (this “Agreement”), is made by Mark A.
Libratore (the “Subordinated Lender”), and acknowledged and agreed to by Liberator Medical
Holdings, Inc., a Nevada corporation (the “Borrower”), Liberator Medical Supply, Inc., a Florida
corporation and a wholly owned direct subsidiary of the Borrower (“Liberator Supply”), and
Liberator Health and Education Services, Inc., a Florida corporation and a wholly owned indirect
subsidiary of the Borrower (together with Liberator Supply, the “Guarantors”, and the Guarantors
and the Borrower, collectively, the “Obligors”), for the benefit of the holders (the “Noteholders”)
of the Notes (as defined below).

     WHEREAS, contemporaneously with the execution and delivery of this Agreement, pursuant to a
Securities Purchase Agreement, dated of as October 17, 2008 (the “Securities Purchase Agreement”),
among the Obligors, Millennium Partners, L.P. (“Millennium”), as a buyer, and the other buyers
party thereto (together with Millennium, the “Buyers”), each Buyer is purchasing 3% Senior
Convertible Notes due 2010 from the Borrower (the “New Notes”), and in connection with the
Securities Purchase Agreement, dated as of May 22, 2008, by and among the Borrower, Liberator
Supply and Millennium, as the sole purchaser, Millennium purchased 3% Senior Convertible Notes due
2010 from the Borrower (together with the New Notes, the “Notes”);

     WHEREAS, the Subordinated Lender is the President and Chief Executive Officer of each of the
Obligors and will derive substantial benefits from the Buyers entering into and performing their
obligations under the Securities Purchase Agreement and the transactions contemplated thereby;

     WHEREAS, Liberator Supply has issued promissory notes to the Subordinated Lender (the
“Subordinated Notes”), the obligations under which have been assumed by the Borrower, which
Subordinated Notes as of the date hereof represent $1,664,000 in aggregate principal amount of
indebtedness owned by the Obligors to the Subordinated Lender; and

     WHEREAS, the Obligors and the Subordinated Lender, as inducement for and as a condition to the
Buyers entering into and performing their obligations under the Securities Purchase Agreement, wish
to provide for the subordination of certain obligations of the Obligors to the Subordinated Lender
to the rights and obligations of the Noteholders under the Notes (“Senior Obligations”).

     NOW, THEREFORE, in consideration of the premises set forth herein, and for other good and
valuable consideration, the parties hereto agree as follows:

     1.     Subordination. Subject to the terms, conditions and limitations set forth herein,
payment by the Obligors of all or any part of the Subordinated Notes to the Subordinated Lender so
long as any Notes are outstanding, including interest, premium, if any, and any other obligations
of the Obligors to the Subordinated Lender with respect thereto or in connection with any other
loans made by the Subordinated Lender to the Obligors (collectively, the “Subordinated
Indebtedness”), is hereby subordinated in right of payment as provided herein
to the prior satisfaction in full of the of all Senior Obligations. Unless and until the
Senior

 

 

Obligations shall have been fully and indefeasibly paid and satisfied and/or all of the
Notes converted in accordance with the terms thereof and all other amounts, thereunder, if any,
paid, and except as otherwise provided in this Agreement, the Subordinated Lender will not, without
the prior written consent of the Noteholders holding at least seventy-five percent (75%) of the
principal amount of the Notes then outstanding (the “Required Holders”), take, demand or receive by
set-off, the pursuit of any legal action to enforce its right to receive or in any other manner,
directly or indirectly, and the Obligors will not make, give or permit, directly or indirectly, by
redemption, purchase or in any other manner, any payment of the whole or any part of the
Subordinated Indebtedness; provided, however, that notwithstanding the forgoing, the Obligors may
make, and the Subordinated Lender may receive, scheduled payments, if any, on account of accrued
interest on the Subordinated Indebtedness in accordance with the terms of the Subordinated Notes so
long as no Event of Default (as defined in the Notes) has occurred and is continuing.

     2.     Distribution. Upon any distribution of assets or readjustment of indebtedness of
an Obligor, whether by reason of liquidation, composition, bankruptcy, arrangement, receivership,
assignment for the benefit of creditors or any other action or proceeding involving the
readjustment of all or any of the indebtedness of such Obligor, the holders of Senior Obligations
shall be entitled to receive payment in full of any and all of the Senior Obligations (including
interest on unpaid principal and interest at the rate provided in the instruments creating the
relevant Senior Obligations accruing on or after the filing of any petition in bankruptcy or
reorganization relating to such Obligor whether or not a claim for post-filing interest is allowed
in such proceeding) prior to the payment of all or any part of the Subordinated Indebtedness. In
the event that, prior to payment in full of the Senior Obligations, any assets or sums are received
by the Subordinated Lender in any such action or proceeding, the Subordinated Lender will hold such
sums in trust for the Noteholders, as their interests may appear and, promptly after receipt
thereof, deliver such assets or sums to the Noteholders on a pro rata basis.

     3.     Priority of Claims. The priorities of the Subordinated Lender’s claims, on the one
hand, and the Noteholders as holders of the Senior Obligations, on the other hand, shall be
effective, and distributions shall be made, in accordance with these provisions regardless of
whether one or more of their claims against an Obligor are invalid or unenforceable or the security
interests or liens securing such claims shall have been perfected.

     4.     Effect of Demand, Waiver, etc. The Subordinated Lender agrees that (i) any demand
for payment of any of the Senior Obligations made by a Noteholder may be rescinded in whole or in
part and any such obligation may be continued, and the liability of each Obligor or any other party
with respect to any such obligation, or any collateral security or guaranty therefor or right of
offset with respect thereto, may, from time to time, in whole or in part, be renewed, extended,
modified, accelerated, compromised, waived, surrendered or released and (ii) the Notes and any
other document or instrument evidencing or governing the terms of any of the Senior Obligations or
the Security Agreement and any other Security Documents (in each case, as defined in the Securities
Purchase Agreement) may be amended, modified, supplemented or terminated, in whole or in part, as
any Buyer or Noteholder may deem advisable from time to time, and any collateral security at any
time held for the payment of
any of the Senior Obligations may be sold, exchanged, waived, surrendered or released, in each

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case without impairing, abridging, releasing or affecting the subordination provided for herein,
notwithstanding any such renewal, extension, modification, acceleration, compromise, amendment,
supplement, termination, sale, exchange, waiver, surrender or release. If at any time payment of
any of the Senior Obligations is rescinded or must otherwise be returned upon the insolvency,
bankruptcy or reorganization of an Obligor or otherwise, the provisions of this Agreement shall
continue to be effective or be reinstated, as the case may be, all as though such payment had not
been made.

     5.     Representations and Warranties of the Subordinated Lender. The Subordinated Lender
hereby represents and warrants to each Buyer as follows:

          (i)     This Agreement has been duly executed and delivered by the Subordinated Lender.

          (ii)     The Subordinated Lender has the capacity to enter into and perform his obligations under
this Agreement.

          (iii)     This Agreement constitutes the valid and legally binding obligation of the Subordinated
Lender.

     6.     Miscellaneous.

          6.1     Survival; Severability. In the event that any provision of this Agreement becomes
or is declared by a court of competent jurisdiction to be illegal, unenforceable or void, this
Agreement shall continue in full force and effect without said provision; provided that in such
case the parties and the Noteholders shall negotiate in good faith to replace such provision with a
new provision which is not illegal, unenforceable or void, as long as such new provision does not
materially change the economic benefits of this Agreement to the parties and the Noteholders.

          6.2     Third Party Beneficiaries. Each Noteholder shall be a third party beneficiary of
this Agreement. Except as specifically set forth in the immediately preceding sentence, nothing in
this Agreement, express or implied, is intended to confer upon any party other than the parties
hereto or their respective successors and permitted assigns any rights, remedies, obligations or
liabilities under or by reason of this Agreement.

          6.3     Successors. The terms and conditions of this Agreement shall inure to the benefit
of and be binding upon the respective successors and assigns of the parties and the Noteholders.
Upon a transfer of a Note or part thereof by a Noteholder, the transferee shall be deemed for all
purposes under this Agreement to be a “Noteholder”.

          6.4     Governing Law; Jurisdiction. This Agreement shall be governed by and construed
under the laws of the State of New York applicable to contracts made and to be performed entirely
within the State of New York. The parties hereby irrevocably submit to the non-exclusive
jurisdiction of the state and federal courts sitting in The City and the County of New York for the
adjudication of any dispute hereunder or in connection herewith or with any transaction
contemplated hereby and hereby irrevocably waives, and agrees not to assert in any
suit, action or proceeding, any claim that it is not personally subject to the jurisdiction of
any

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such court, that such suit, action or proceeding is brought in an inconvenient forum or that
the venue of such suit, action or proceeding is improper. Each party hereto hereby irrevocably
waives personal service of process and consents to process being served in any such suit, action or
proceeding by mailing a copy thereof to it at the address in effect for notices to it under this
Agreement and agrees that such service shall constitute good and sufficient service of process and
notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve
process in any manner permitted by law.

          6.5     Headings. The headings used in this Agreement are used for convenience only and
are not to be considered in construing or interpreting this Agreement.

          6.6     Notices. Any notice, demand or request required or permitted to be given by the
Subordinated Lender or any Obligor pursuant to the terms of this Agreement shall be in writing and
shall be deemed delivered (i) when delivered personally or by verifiable facsimile transmission,
unless such delivery is made on a day that is not a Business Day, in which case such delivery will
be deemed to be made on the next succeeding Business Day and (ii) on the next Business Day after
timely delivery to an overnight courier. Any notice, demand or request given to (x) any party,
shall be addressed to such party at the principal offices of the Borrower, (y) any Noteholder,
shall be addressed to such Noteholder at the address set forth in the Schedule of Buyers attached
to the Securities Purchase Agreement, or (z) at such other address as any party or Noteholder may
specify to the parties and the Noteholders by written notice.

          6.7     Entire Agreement; Amendments. This Agreement constitutes the entire agreement
between the parties with regard to the subject matter hereof, superseding all prior agreements or
understandings, whether written or oral, between or among the parties. Except as expressly
provided herein, neither this Agreement nor any term hereof may be amended or waived except
pursuant to a written instrument executed by the parties and Required Holders, and no provision
hereof may be waived other than by a written instrument signed by the Required Holders and the
parties. Any waiver or consent shall be effective only in the specific instance and for the
specific purpose for which given.

          6.8     No Waiver; Cumulative Remedies. No party hereto and none of the Noteholders shall
by any act, delay, omission or otherwise be deemed to have waived any of its rights or remedies
hereunder. No failure to exercise, nor any delay in exercising on the part of any party hereto or
any Noteholder, any right, power or privilege hereunder, shall operate as a waiver thereof, nor
shall any single or partial exercise of any right, power or privilege hereunder preclude any other
or future exercise thereof or the exercise of any other right, power or privilege. The rights and
remedies hereunder provided are cumulative and may be exercised singly or concurrently, and are not
exclusive of any rights and remedies provided by law.

          6.9     Counterparts. This Agreement may be executed in two or more identical
counterparts, all of which shall be considered one and the same agreement and shall become
effective when counterparts have been signed by each party and delivered to the other party;
provided that a facsimile signature shall be considered due execution and shall be binding
upon the signatory thereto with the same force and effect as if the signature were an
original, not a facsimile signature.

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          6.10     Limitation By Law. All rights, remedies and powers provided in this Agreement
may be exercised only to the extent that the exercise thereof does not violate any applicable
provision of law, and the provisions of this Agreement are intended to be subject to all applicable
mandatory provisions of law that may be controlling and to be limited to the extent necessary so
that they shall not render this Agreement invalid, unenforceable, in whole or in part, or not
entitled to be recorded, registered or filed under the provisions of any applicable law.

[Signature Page Follows.]

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

	 	 	 	 	 
	 	SUBORDINATED LENDER:

 	 
	 	/s/ Mark A. Libratore
 	 
	 	Mark A. Libratore 	 
	 	 	 
	 

ACKNOWLEDGED AND AGREED TO BY:

BORROWER:

LIBERATOR MEDICAL HOLDINGS, INC.

	 	 	 	 	 
	 	 
	By:  	/s/ Mark A. Libratore
 	 
	 	 	Name:  	Mark A. Libratore 	 
	 	 	Title:  	President 	 
	 

GUARANTORS:

LIBERATOR MEDICAL SUPPLY, INC.

	 	 	 	 	 
	 	 
	By:  	/s/ Mark A. Libratore
 	 
	 	 	Name:  	Mark A. Libratore 	 
	 	 	Title:  	President 	 
	 

LIBERATOR HEALTH AND EDUCATION SERVICES, INC.

	 	 	 	 	 
	 	 
	By:  	/s/ Mark A. Libratore
 	 
	 	 	Name:  	Mark A. Libratore 	 
	 	 	Title:  	President 	 
	 

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