Amendment to Stock Purchase Agreement, dated as of February 4, 2023

Exhibit 2.1

FIRST AMENDMENT TO

STOCK PURCHASE AGREEMENT

between

LIFEMD, INC.,

and

CLEARED TECHNOLOGIES, PBC,

and

THE SELLERS LISTED ON SCHEDULE 1 OF THE AGREEMENT

This FIRST AMENDMENT TO STOCK PURCHASE AGREEMENT (the “Amendment”) is made effective as of February 4, 2023 (the “Effective Date”), between the Sellers identified on Schedule 1 of the Agreement (as defined below) (the “Sellers”) and LifeMD, Inc., a Delaware corporation (“Buyer”). Capitalized terms not otherwise defined herein shall have the meanings ascribed to them in the Stock Purchase Agreement, dated January 11, 2022, by and among the Sellers and the Buyer therein (the “Agreement”).

RECITALS

WHEREAS, Sellers and Buyer (together, the “Parties”, and each, a “Party”) entered into a certain Agreement pursuant to which Sellers sold to Buyer, and Buyer purchased from Sellers, the Shares, subject to the terms and conditions set forth therein;

WHEREAS, Sellers and Buyer believe it to be in their respective best interest to amend the Agreement; and

WHEREAS, Sellers and Buyer desire to amend the Agreement as set forth herein;

AGREEMENT

NOW, THEREFORE, in consideration of the mutual covenants and agreements hereinafter set forth and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Parties hereto agree as follows:

a. Section 2 of the Agreement, Purchase and Sale, is hereby amended and restated in its entirety to read:

“Section 2.01 Purchase and Sale. Subject to the terms and conditions set forth herein and the Amendment, at the Closing, Sellers shall sell to Buyer, and Buyer shall purchase from Sellers, the Shares.

Section 2.02 Purchase Price. The aggregate purchase price for the Shares shall be $3,670,000, (the “Purchase Price”), consisting of (a) $460,000 to be paid at Closing (the “Initial Payment”), (b) $3,210,000 payable in quarterly installments in accordance with the schedule below:

Section 2.03 Satisfaction of the Purchase Price. All payments made by Buyer to Sellers hereunder shall be made either by:

To the extent any of the above payments are made by issuing Buyer Shares, the timing requirement associated with such payment shall be satisfied by the Buyer issuing an instruction to Buyer’s transfer agent to issue the applicable number of Buyer Shares to the Seller Representative, understanding that the transfer agent will require information from the Seller Representative, including, by way of example, address and tax identification number, before such shares are actually issued. Sellers hereby acknowledge and agree that any issuance of Buyer Shares pursuant to this Section 2.03 shall be issued by Buyer to the Seller Representative, and not to the Sellers, and such issuance to the Seller Representative shall fulfill the payment obligations of Buyer herein.

Section 2.04 Acceleration. Upon default in the payment or performance of any portion of the Purchase Price of Buyer to Sellers resulting from Buyer’s negligence or intentional misconduct, or upon the occurrence of any other material default by Buyer under this Amendment, all or any portion of the Purchase Price of Buyer to Sellers, whether due or not, that remains unpaid, shall at Sellers’ option expressed in writing by Sellers’ Representative become immediately due and payable. Notwithstanding the foregoing, Sellers shall not be entitled to acceleration as a result of any delay or failure to perform hereunder, which delay or failure is due to a failure by Sellers to cooperate, including by failing to provide information necessary to facilitate payment, whether in the form of cash or Buyer Shares.

Section 2.05 Withholding Tax. Buyer and the Company shall be entitled to deduct and withhold from the Purchase Price all Taxes that Buyer and the Company may be required to deduct and withhold under any provision of Tax Law. All such withheld amounts shall be treated as delivered to Sellers hereunder.

b. Section 8.02 of the Agreement, Indemnification By Sellers, is hereby amended and restated in its entirety to read:

“Section 8.02 Indemnification By Sellers. Subject to the other terms and conditions of this ARTICLE VIII, each Seller shall, jointly and severally, indemnify and defend each of Buyer and its Affiliates (including the Company) and their respective Representatives (collectively, the “Buyer Indemnitees”) against, and shall hold each of them harmless from and against, and shall pay and reimburse each of them for, any and all Losses incurred or sustained by, or imposed upon, the Buyer Indemnitees based upon, arising out of, with respect to or by reason of:

(a) any inaccuracy in or breach of the representations or warranties of any Seller contained in Section 3.01 and 3.03 as of the date such representation or warranty was made or as if such representation or warranty was made on and as of the Closing Date.”

c. Section 3 of the Agreement, Representations and Warranties of the Seller, other than Sections 3.01 and 3.03 is hereby removed in its entirety.

d. Section 4 of the Agreement, Representations and Warranties of Buyer, other than Sections 4.01 and 4.04 is hereby removed in its entirety.

(a) In consideration of the covenants, agreements and undertakings of the Parties under this Amendment, each Party, on behalf of itself and its respective present and former parents, subsidiaries, affiliates, officers, directors, shareholders, members, successors, and assigns (collectively, “Releasors”) hereby releases, waives, and forever discharges the other Party and its respective present and former, direct and indirect, parents, subsidiaries, affiliates, employees, officers, directors, shareholders, members, agents, representatives, permitted successors, and permitted assigns (collectively, “Releasees”) of and from any and all actions, causes of action, suits, losses, liabilities, rights, debts, dues, sums of money, accounts, reckonings, obligations, costs, expenses, liens, bonds, bills, specialties, covenants, contracts, controversies, agreements, promises, variances, trespasses, damages, judgments, extents, executions, claims, and demands, of every kind and nature whatsoever, whether now known or unknown, foreseen or unforeseen, matured or unmatured, suspected or unsuspected, in law, admiralty, or equity, including any and all claims that may arise from the representations or warranties made under the Agreement, any assertions of breach of the Agreement, and any claims of indemnification under the Agreement (collectively, “Claims”), which any of such Releasors ever had, now have, or hereafter can, shall, or may have against any of such Releasees for, upon, or by reason of any matter, cause, or thing whatsoever from the beginning of time through the date of this Amendment arising out of or relating to the Indemnification Escrow Fund, the Escrow Agreement, any breaches (or alleged breaches) by Buyer on or before the date hereof relating to the Agreement or any breaches (or alleged breaches) by Sellers described in the Claim Letter attached hereto as Exhibit A (the “Claim Letter”) or arising out of or relating to the Agreement; provided, however, that such release shall not apply to any Claims related to the Sellers’ representations and warranties set forth in Section 3.01 and 3.03 of the Agreement or Buyer’s representations and warranties set forth in Section 4.01 and 4.04 of the Agreement.

(b) Each Releasor understands that it may later discover Claims or facts that may be different from, or in addition to, those that it or any other Releasor now knows or believes to exist regarding the subject matter of the release contained in this Section 2, and which, if known at the time of signing this Amendment, may have materially affected this Amendment and such Party’s decision to enter into it and grant the release contained in this Section 2. Nevertheless, the Releasors intend to fully, finally and forever settle and release all Claims that now exist, may exist, or previously existed, as set out in the release contained in this Section 2, whether known or unknown, foreseen or unforeseen, or suspected or unsuspected, and the release given herein is and will remain in effect as a complete release, notwithstanding the discovery or existence of such additional or different facts. The Releasors hereby waive any right or Claims that might arise as a result of such different or additional Claims or facts. The Releasors expressly, knowingly and intentionally waive any and all rights, benefits and protections of any state or federal statute or common law principle limiting the scope of a general release.

(c) Except for any Claims related to the Sellers’ representations and warranties set forth in Section 3.01 and 3.03 of the Agreement, Sellers shall not have any personal liability whatsoever to the Buyer under the Agreement, this Amendment, or any other document delivered in connection with the transaction and shall not be obligated to indemnify or hold harmless Buyer, or its affiliates, officers, directors, managers, employees, agents or other representatives from or against any cost, loss, expense, damage or liability.

3. Bankruptcy. In the event (a) Buyer files for bankruptcy, whether voluntary or involuntary, or (b) any court of competent jurisdiction or governmental or regulatory authority asserting jurisdiction over the subject matter hereof or the Parties hereto enters a final order, judgment, or other finding that the payment of all or any part of the payment constitutes a voidable or preferential transfer, such payment constitutes an improper or disproportionate payment, or the payment is otherwise in violation of law or subject to a claim of preference, then Sellers may in their sole discretion, but subject to any limits provided for in the Bankruptcy Code found in Title 11 of the United States Code, in addition to any other remedy provided by law, equity, statute or contract, enforce this Amendment according to its express terms and conditions.

4. Governing Document. In the case of any inconsistency between the provisions of the Agreement and this Amendment, the provisions of this Amendment shall govern and control. All terms and conditions of the Agreement not specifically amended, altered or deleted in this Amendment shall remain in full force and effect.

5. Time of the Essence. Time is of the essence of this Amendment and the provisions contained herein.

6. Expenses. Within five (5) business days of the Effective Date, Buyer shall reimburse Cleared Technologies Administrator, LLC ten thousand dollars (US$10,000.00) for its legal expenses associated with the administration of the purchase price.

[Remainder of page intentionally left blank; signature page follows]

IN WITNESS WHEREOF, the parties have executed this Amendment as of the date first above written.

[signatures continued on following pages]

[signatures continued on following pages]

Exhibit A

Claim Letter