Exhibit 10.1

AMENDMENT NO. 2 TO LOAN DOCUMENTS

THIS AMENDMENT NO. 2 TO LOAN DOCUMENTS (“Amendment”) is dated as of December 31, 2025 (“Effective Date”), by and between SIMPLIFY INVENTIONS, LLC, a Delaware limited liability company (“Lender”), and THE ARENA GROUP HOLDINGS, INC., a Delaware corporation (“Borrower”), and is acknowledged, agreed and affirmed by each of the undersigned guarantors that are a party to the Guaranty (defined below) (each, a “Guarantor” and collectively, the “Guarantors”).

RECITALS

A. LOAN AGREEMENT. Borrower is indebted to Lender under that certain Loan Agreement dated as of March 13, 2024, as amended by that certain Amendment No. 1 to Loan Documents dated as of August 19, 2024 (collectively, the “Loan Agreement”), with respect to a certain demand revolving loan made by Lender to Borrower in the maximum principal amount of Fifty Million and 00/100 Dollars ($50,000,000.00) (the “Loan”). The Loan is supported and/or secured by certain other loan documents executed in connection with the Loan. All capitalized terms used but not defined in this Amendment have the meanings ascribed to them in the Loan Agreement or in the Loan Documents being amended.

B. EVIDENCE OF DEBT. The Loan is evidenced by a certain Amended and Restated Promissory Note in the maximum principal amount of Fifty Million and 00/100 Dollars ($50,000,000.00) dated as of August 19, 2024 (the “Note”).

C. COLLATERAL. The Loan is supported and/or secured by the following loan documents:

(The above documents are collectively referred to as the “Related Documents”).

(The Related Documents together with the Loan Agreement and the Note are collectively, the “Loan Documents”).

D. AMENDMENT REQUEST. Borrower, Guarantors and Lender desire to amend certain of the terms and conditions of the Loan Agreement and certain of the Loan Documents described above and all of the parties are willing to execute this Amendment.

AGREEMENT

In consideration of the above recitals, which are incorporated into and deemed a part hereof, and for other good and valuable consideration, the receipt and adequacy of which are hereby acknowledged, the parties agree as follows:

1. AMENDMENTS. The Loan Agreement and Loan Documents are amended as follows:

A. AMENDMENT OF LOAN AGREEMENT. The Loan Agreement is amended as follows:

(i) The definition of “Loan Amount” in Section 1.1 of the Loan Agreement amended and restated in its entirety and shall state as follows:

“‘Loan Amount’ shall mean maximum principal amount of Twenty-Five Million and 00/100 Dollars ($25,000,000.00).”

(ii) The definition of “Maturity Date” is in Section 1.1 of the Loan Agreement amended and restated in its entirety and shall state as follows:

“‘Maturity Date’ shall mean December 1, 2027.”

B. AMENDMENT OF AMENDED AND RESTATED PROMISSORY NOTE. The Note is amended as follows:

(i) The Note is amended to reduce the maximum principal amount of the Note from Fifty Million and 00/100 Dollars ($50,000,000.00) to Twenty-Five Million and 00/100 Dollars ($25,000,000.00). Any reference in the Note to the principal amount of the Note as “$50,000,000.00” or “Fifty Million and 00/100 Dollars ($50,000,000.00)” is amended to be “$25,000,000.00” or “Twenty-Five Million and 00/100 Dollars ($25,000,000.00),” as appropriate.

C. AMENDMENT OF TENNESSEE AFFIDAVIT. Upon request of Lender, Borrower agrees to promptly execute, or cause to be executed, and return to Lender an original notarized Tennessee Indebtedness Tax Affidavit – Allocation of Collateral (Debtor) in form required by the taxing authority of the State of Tennessee and acceptable to Lender.

AMENDMENT NO. 2 TO LOAN DOCUMENTS

2. CONDITIONS PRECEDENT. The terms and conditions of this Amendment shall be subject to Lender’s receipt and review (as applicable) of and/or Borrower’s compliance with the following, each of which shall be to the satisfaction of Lender:

A. this Amendment executed by Borrower;

B. Officer’s/Member’s Certificates executed by Borrower and each Guarantor;

C. such other documentation that Lender may request from Borrower from time to time in connection with this Amendment or the Loan;

D. payment by Borrower to Lender of fees and out of pocket costs incurred by Lender in connection with the transactions contemplated by this Amendment, including, without limitation, Lender’s attorneys’ fees and costs in connection with this Amendment; and

E. no Event of Default, or condition or event that, with the giving of notice or the running of time, or both, would constitute an Event of Default under the Loan Agreement or the Loan Documents shall have occurred and be continuing as of the date hereof.

3. NOT A NOVATION. This Amendment is not an agreement to substitute a new obligation or to extinguish Borrower’s existing obligation under the Loan Agreement and Loan Documents and shall not constitute a novation as to the obligations of any of the parties.

4. REAFFIRMATION OF GUARANTY. As a specific inducement to Lender, and in consideration of the Lender’s reliance hereon, the undersigned Guarantors have each executed the Guaranty dated March 13, 2024, and each Guarantor hereby acknowledges and agrees to the amendments, modifications, and waivers set forth in this Amendment and the Note and reaffirms its Guaranty with respect to all liabilities, obligations and the Indebtedness therein guaranteed as herein amended and modified, and Guarantors further acknowledge that they remain liable in accordance with the terms of the Guaranty, notwithstanding the modifications and amendments herein made.

5. REPRESENTATIONS AND WARRANTIES. Borrower hereby represents and warrants that, after giving effect to the amendments contained herein:

A. execution, delivery and performance of this Amendment, the Loan Documents and any other documents and instruments required under this Amendment, the Note, the Loan Agreement or the Loan Documents are within Borrower’s corporate powers, have been duly authorized, are not in contravention of law or the terms of Borrower’s Articles of Incorporation or Bylaws, and do not require the consent or approval of any governmental body, agency or authority; and this Amendment and any other documents and instruments required under this Amendment or the Loan Agreement will be valid and binding in accordance with their terms;

B. the continuing representations and warranties of Borrower set forth in the Loan Documents are true and correct on and as of the date hereof, with the same force and effect as if made on and as of the date hereof; and

C. no Event of Default, or condition or event that, with the giving of notice or the running of time, or both, would constitute an Event of Default under the Loan Documents, has occurred and is continuing as of the date hereof.

AMENDMENT NO. 2 TO LOAN DOCUMENTS

6. EFFECTIVE DATE. This Amendment will be effective as of the Effective Date.

7. COUNTERPARTS. This Amendment may be executed and acknowledged in counterparts, each of which shall constitute an original and all of which shall together constitute one and the same Amendment.

8. COSTS AND EXPENSES. Borrower is responsible for all costs incurred by Lender, including, without limitation, reasonable attorney fees, with regard to the preparation and execution of this Amendment and all other documents and instruments required under this Amendment. Failure by Borrower to pay those fees will be a default of this Amendment.

9. NON-WAIVER OF DEFAULT. The execution of this Amendment will not be deemed to be a waiver of any default or Event of Default that is either (a) existing and not known by Lender at the Effective Date, or (b) occurs at any time following the Effective Date.

10. RELEASE. Borrower and each Guarantor waives, discharges, and forever releases Lender, Lender’s employees, officers, directors, attorneys, stockholders, and their successors and assigns, from and of any and all claims, causes of action, allegations or assertions that Borrower or any Guarantor has or may have had at any time up through and including the Effective Date, against any or all of the foregoing, regardless of whether any such claims, causes of action, allegations or assertions are known to Borrower or any Guarantor or whether any such claims, causes of action, allegations or assertions arose as a result of Lender’s actions or omissions in connection with the Loan Documents, or any amendments, extensions or modifications thereto, or Lender’s administration of the indebtedness under the Loan Documents or otherwise.

11. FURTHER AMENDMENT. This Amendment is not an agreement to any further or other amendment of the Loan Agreement or the Loan Documents.

12. SURVIVAL AND REAFFIRMATION. Each signatory hereto, by execution hereof, respectively agrees for itself, in all capacities in which each signatory has executed the Loan Agreement or any of the Loan Documents as follows:

A. That, except as herein modified or amended, all terms, conditions, covenants, representations and warranties contained in the Loan Agreement, the Note and/or Loan Documents shall remain in full force and effect, and that the undersigned hereby consent to and acknowledge the foregoing Amendment.

B. That the liability of the undersigned howsoever arising or provided for in the Loan Agreement, the Note and the Loan Documents, as hereby modified or amended, is hereby reaffirmed.

13. COUNTERPARTS. This Agreement may be executed in any number of counterparts with the same effect as if all signatories had signed the same document. All counterparts must be construed together to constitute one instrument. Facsimile or scanned copies of signatures are treated as original signatures for all purposes.

AMENDMENT NO. 2 TO LOAN DOCUMENTS

IN WITNESS WHEREOF, the parties hereto have executed this Amendment No. 1 to Loan Documents as of the Effective Date.

AMENDMENT NO. 2 TO LOAN DOCUMENTS

AGREEMENT AND AFFIRMATION OF GUARANTORS

By executing this Agreement and Affirmation of Guarantors (“Agreement and Affirmation”), each Guarantor: (1) acknowledges and agrees that such Guarantor has completely read and understands the Amendment No. 2 to Loan Documents dated December 31, 2025 (the “Amendment”) and corresponding documents executed in connection therewith (“Amendment Documents”); (2) consents to all of the provisions of the Amendment Documents relating to Borrower; (3) acknowledges receipt of good and lawful consideration for this Agreement and Affirmation of its Guaranty in favor of Lender; (4) agrees promptly to furnish such financial statements to Lender concerning such Guarantor as Lender shall request; (5) agrees to all of those portions of the Amendment Documents which apply to such Guarantor; (6) affirms its respective obligations to Lender under the Guaranty and acknowledges that the Guaranty remains in full force and effect in accordance with its terms, as the same may have been amended and/or restated in connection with the Amendment, subject to no setoff, defense or counterclaim, (7) acknowledges and agrees that the Amendment Documents and this Agreement and Affirmation has been freely executed without duress and after an opportunity was provided to Guarantor for review of such agreements by competent legal counsel of Guarantor’s choice; and (8) acknowledges that Lender has provided Guarantor with a copy of the Amendment Documents and this Agreement and Affirmation and such other Loan Documents, as Guarantor has reasonably requested.

ACKNOWLEDGEMENT AND AGREEMENT OF GUARANTORS

Exhibit 10.2

AMENDMENT NO. 4 TO

THIRD AMENDED AND RESTATED NOTE PURCHASE AGREEMENT

THIS AMENDMENT NO. 4 TO THIRD AMENDED AND RESTATED NOTE PURCHASE AGREEMENT (this “Amendment”) is made and entered into as of December 31, 2025, by and among The Arena Group Holdings, Inc., a Delaware corporation (the “Borrower”), the Guarantors from time to time party to the Note Purchase Agreement (as defined below), each of the Purchasers from time to time named on Schedule I to the Note Purchase Agreement, and Renew Group Private Limited, in its capacity as agent for the Purchasers (in such capacity, “Agent”). Capitalized terms used but not defined herein shall have the respective meanings assigned to such terms in the Note Purchase Agreement, as amended hereby.

WHEREAS, pursuant to the Third Amended and Restated Note Purchase Agreement dated as of December 15, 2022 (as amended by that certain Amendment No. 1 to Third Amended and Restated Note Purchase Agreement, dated as of August 14, 2023, that certain Amendment No. 2 to Third Amended and Restated Note Purchase Agreement, dated as of December 1, 2023, and Amendment No. 3 to Third Amended and Restated Note Purchase Agreement, dated as of July 12, 2024, by and among the Borrower, the Guarantors party thereto, the Purchasers party thereto and the Agent, and as further as amended, restated, supplemented or otherwise modified from time to time, collectively, the “Note Purchase Agreement”), by and among the Borrower, the Guarantors from time to time party thereto, the Purchasers from time to time party thereto and the Agent, the Purchasers have purchased certain Notes from the Borrower, and the Guarantors have guaranteed the payment of the Obligations, all upon the terms and subject to the conditions set forth therein; and

WHEREAS, the Borrower has requested that the Purchasers and the Agent make certain amendments to the Note Purchase Agreement, in each case, contingent upon the conditions set forth in Section II hereof.

NOW, THEREFORE, in consideration of the foregoing, and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereby agree as follows:

Effective as of the Amendment No. 4 Effective Date, the definition of “Maturity Date” in Section 1.1 of the Note Purchase Agreement is amended and restated in its entirety as follows:

“Maturity Date” means the earlier of (i) December 31, 2027, or (ii) the date that the Obligations have been accelerated pursuant to and in accordance with the terms of this Agreement.

This Amendment shall become effective as of the first date upon which each of the following conditions is satisfied (the “Amendment No. 4 Effective Date”):

(1) Amendment Documents. The Borrower and Guarantors shall have delivered or caused to be delivered to the Agent an executed version of this Amendment.

(2) Officer’s/Members Certificates. The Borrower and Guarantors shall have delivered, or caused to be delivered to the Agent, Officer’s/Member’s Certificates, in form reasonably acceptable to Agent, executed by Borrower and each Guarantor. 

(3) Curtailment Payment. The Borrower shall have paid to Agent in readily available funds by wire transfer a curtailment payment in the amount of Thirteen Million and 00/100 Dollars ($13,000,000.00), which curtailment payment will be applied to reduce the outstanding principal balance of the Notes.

(4) Representations and Warranties. The representations and warranties set forth in the Note Purchase Agreement and the other Note Documents shall be true and correct in all material respects (or in all respects with respect to any representation or warranty which by its terms is limited as to materiality, in each case, after giving effect to such qualification) on and as of the Amendment No. 4 Effective Date. 

(5) No Default. After giving effect to Amendment and the transactions contemplated thereby, no event shall have occurred or be continuing or would result from the amendments contemplated hereby that would constitute an Event of Default or a Default. 

(6) No Prohibition. No order, judgment or decree of any court, arbitrator or Governmental Authority shall purport to enjoin or restrain Agent or any Purchaser from entering into this Amendment or consummating the transactions contemplated hereby. 

(7) Fees and Expenses. The Agent and Purchasers shall have received all fees and other amounts due or payable on the Amendment No. 4 Effective Date, including, reimbursement or payment of all reasonable and documented out-of-pocket expenses required to be reimbursed or paid by the Note Parties hereunder or under the Note Documents.

(1) Ratification, Etc.. Except as expressly amended hereby, the Note Purchase Agreement and the other Note Documents and all documents, instruments and agreements related thereto are hereby ratified and confirmed in all respects and shall continue in full force and effect. This Amendment and the Note Purchase Agreement shall hereafter be read and construed together as a single document, and all references in the Note Purchase Agreement, any other Note Document or any agreement or instrument related to the Note Purchase Agreement shall hereafter refer to the Note Purchase Agreement as amended by this Amendment. This Amendment shall constitute a Note Document for all purposes of the Note Purchase Agreement and the other Note Documents.

(2) Reaffirmation. Each of the Note Parties as borrower, debtor, grantor, chargor, pledgor, assignor, guarantor, or in other any other capacity in which such Note Party grants Liens or security interests in its property, assets or undertakings or acts as a guarantor or co-obligor, as the case may be, hereby (a) ratifies and reaffirms all of its payment and performance obligations, contingent or otherwise, under each of the Note Documents to which it is a party and (b) to the extent such Note Party granted Liens on or security interests in any of its property, assets or undertakings pursuant to any such Note Document as security for or otherwise guaranteed the Obligations, ratifies and reaffirms such guarantee and grant of security interests and Liens and confirms and agrees that such security interests and Liens shall continue in full force and effect and ranks as continuing security for the payment and discharge of the liabilities and obligations secured or guaranteed thereunder (as the case may be), including, without limitation, all of the Obligations as amended hereby.

(3) No Waiver. Nothing contained in this Amendment shall be deemed to (a) constitute a waiver of any Default or Event of Default that may hereafter occur or heretofore have occurred and be continuing, (b) except as a result of the amendments expressly set forth in Section I of this Amendment, otherwise modify any provision of the Note Purchase Agreement or any other Note Document, or (c) give rise to any defenses or counterclaims to the Agent’s or any Purchaser’s right to compel payment of the Obligations when due or to otherwise enforce their respective rights and remedies under the Note Purchase Agreement and the other Note Documents.

(4) Release. Each Note Party hereby remises, releases, acquits, satisfies and forever discharges the Agent and the Purchasers, their agents, employees, officers, directors, predecessors, attorneys and all others acting on behalf of or at the direction of the Agent or the Purchasers, of and from any and all manner of actions, causes of action, suit, debts, accounts, covenants, contracts, controversies, agreements, variances, damages, judgments, claims and demands whatsoever, in law or in equity, which any of such parties ever had, or now has, to the extent arising from or in connection with any act, omission or state of facts taken or existing on or prior to the Amendment No. 4 Effective Date, against the Agent and the Purchasers, their agents, employees, officers, directors, attorneys and all persons acting on behalf of or at the direction of the Agent or the Purchasers (“Releasees”), for, upon or by reason of any matter, cause or thing whatsoever arising under, or in connection with, or otherwise related to, the Note Documents through the Amendment No. 4 Effective Date. Without limiting the generality of the foregoing, each Note Party hereby waives and affirmatively agrees not to allege or otherwise pursue any defenses, affirmative defenses, counterclaims, claims, causes of action, setoffs or other rights they have or may have under, or in connection with, or otherwise related to, the Note Documents as of the Amendment No. 4 Effective Date, including, but not limited to, the rights to contest any conduct of the Agent, the Purchasers or other Releasees on or prior to the Amendment No. 4 Effective Date.

(5) Governing Law. THIS AMENDMENT SHALL BE GOVERNED BY, AND SHALL BE CONSTRUED AND ENFORCED IN ACCORDANCE WITH, THE INTERNAL LAWS OF THE STATE OF NEW YORK, EXCEPT TO THE EXTENT ANY SUCH OTHER NOTE DOCUMENT EXPRESSLY SELECTS THE LAW OF ANOTHER JURISDICTION AS GOVERNING LAW THEREOF, IN WHICH CASE THE LAW OF SUCH OTHER JURISDICTION SHALL GOVERN.

(6) Counterparts; Effectiveness. This Amendment may be executed via facsimile or other electronic method of transmission in any number of counterparts and by different parties hereto in separate counterparts, each of which when so executed and delivered shall be deemed an original, but all of which counterparts together shall constitute one and the same instrument.

[signature pages follow]

IN WITNESS WHEREOF, each of the undersigned has duly executed this Amendment to Note Purchase Agreement as of the date first set forth above.

[signature page – amendment no. 4 to third amended and restated note purchase agreement]

[signature page – amendment no. 4 to third amended and restated note purchase agreement]

[Signature Page – Amendment No. 4 to Third Amended and Restated Note Purchase Agreement]

Exhibit 99.1

The Arena Group Announces Debt Maturity Extensions, Supporting Refinancing Efforts

New York, NY – January 7, 2026 – The Arena Group Holdings, Inc. (NYSE: AREN) (“The Arena Group” or “the Company”), the brand, data and IP company home to iconic brands such as TheStreet, Parade, Men’s Journal, Athlon Sports, ShopHQ and more, today announced that it has entered into agreements with its lenders to extend the maturity dates of two existing debt facilities, providing additional flexibility as the Company continues to advance its refinancing plans.

Specifically, the Company has extended the maturity of its Term Loan with Renew Group Private Limited from Dec. 31, 2026 to Dec. 31, 2027, and the Company made a principal payment to retire $13 million of debt reducing outstanding principal to $97.7 million as of Dec. 31, 2025. Similarly, the Company extended the maturity of its Line of Credit with Simplify Inventions LLC from Dec. 1, 2026 to Dec. 1, 2027, and reduced the facility size from $50 million to $25 million. The facility remains undrawn at Dec. 31, 2025 and the company has adequate liquidity with cash on the balance sheet of over $9 million as of Dec. 31, 2025 after the paydown.

“The flexibility provided by these extensions validates our commitment to securing the most favorable long-term capital structure for the Company,” said Paul Edmondson, CEO of The Arena Group. “We remain focused on executing a disciplined refinancing process that prioritizes long-term value creation over speed.”

The Company believes these extensions provide the Company with sufficient runway to continue its pursuit of a permanent financing solution. This deliberate approach allows the Company adequate time to finalize a long-term facility on favorable terms.

About The Arena Group

The Arena Group Holdings, Inc (NYSE:AREN) is a brand, data and IP company that builds, acquires, and scales high-performing digital assets. We combine technology, storytelling, and entrepreneurship to create deep content verticals that engage passionate audiences across sports & leisure, lifestyle, and finance. Through our portfolio of owned and operated brands including TheStreet, Parade, Men’s Journal, Athlon Sports, the Adventure Network (Surfer, Powder, Bike, etc), ShopHQ and others, we deliver trusted content and meaningful experiences to millions of users each month. Visit us at thearenagroup.net to learn more.

Media Contact

Morgan Fitzgerald

[email protected]

Investor Relations Contact

Rob Fink, FNK IR

[email protected]

646.809.4048