MDIA / MediaCo Holding Inc. - Pemfailan SEC, Laporan Tahunan, Penyata Proksi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): August 08, 2025 MediaCo Holding I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): August 08, 2025 MediaCo Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): August 11, 2025 MediaCo Holding I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): August 11, 2025 MediaCo Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incor

MEDIACO REPORTS SECOND QUARTER NET REVENUE OF $31.2 MILLION AND FIRST HALF OF 2025 NET REVENUE OF $59.3 MILLION MediaCo's Growth Strategy Delivers: Higher Revenues, Stronger Margins Momentum Builds in 2025 as MediaCo Achieves Record First Half Revenu

Exhibit 99.1 SECOND QUARTER 2025 EARNINGS RELEASE August 11, 2025 MEDIACO REPORTS SECOND QUARTER NET REVENUE OF $31.2 MILLION AND FIRST HALF OF 2025 NET REVENUE OF $59.3 MILLION MediaCo's Growth Strategy Delivers: Higher Revenues, Stronger Margins Momentum Builds in 2025 as MediaCo Achieves Record First Half Revenues MediaCo First Half Digital Revenue hits Milestone 33.0% of Total Revenue Financia

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant  ☐ Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission only (as permitted by Rule

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-3

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING OMB APPROVAL OMB Number: 3235-0058 Expires: May 31, 2025 Estimated average burden hours per response ............ 2.50 SEC File Number: 001-39029 CUSIP Number: 58450D104 (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended: M

Financial Statements and Exhibits, Changes in Registrant's Certifying Accountant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): May 5, 2025 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpora

Letter from Ernst & Young LLP to the Securities and Exchange Commission regarding change in certifying accountants.

May 7, 2025 Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549 Commissioners: We have read Item 4.01 of Form 8-K dated May 5, 2025, of MediaCo Holding Inc. and are in agreement with the statements contained in paragraphs (a), (b), (d) and (e) on page 2 therein. We have no basis to agree or disagree with other statements of the registrant contained therein. /s/ Ernst & Young

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): May 5, 2025 (May 1, 2025) MediaCo Holding Inc. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or other jurisdiction of incorporation) (Comm

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) ☒ Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended December 31, 2024 ☐ Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 For the transition period from to Commission File Number 001-3902

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended December 31, 2024 o Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 For the transition period from to Commission File Number 001-39029 MEDIACO HOLDING IN

Amended and Restated Securities Trading Policy

Subsidiaries of MediaCo Holding Inc.

Exhibit 21 INFORMATION REGARDING SUBSIDIARIES AND VARIABLE INTEREST ENTITIES OF THE REGISTRANT Name Under Which Subsidiary Does Business Jurisdiction of Organization MediaCo Holding Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING OMB APPROVAL OMB Number: 3235-0058 Expires: April 30, 2025 Estimated average burden hours per response ............ 2.50 SEC File Number: 001-39029 CUSIP Number: 58450D104 (Check one): ☒ Form 10-K ☐ Form 20-F ☐ Form 11-K ☐ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended:

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): March 10, 2025 MediaCo Holding Inc. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or other jurisdiction of incorporation) (Commission File

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934         Filed by the Registrant     ☒ Filed by a party other than the Registrant      ☐         Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission only (as permitted

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934         Filed by the Registrant     ☒ Filed by a party other than the Registrant      ☐         Check the appropriate box: ☒ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission only (as permitted b

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 13, 2024 (December 12, 2024) MediaCo Holding Inc. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or other jurisdiction of incorpor

At-The-Market Sales Agreement, dated December 12, 2024, by and among MediaCo Holding, Inc., BTIG, LLC and Moelis & Company LLC

Exhibit 1.1 MEDIACO HOLDING INC. UP TO $2,031,019 OF CLASS A COMMON STOCK ($0.01 par value per share) AT-THE-MARKET SALES AGREEMENT December 12, 2024 BTIG, LLC 65 East 55th Street New York, New York 10022 Moelis & Company LLC 399 Park Avenue, 5th Floor New York, New York 10022 Ladies and Gentlemen: MediaCo Holding Inc., an Indiana corporation (the “Company”), confirms its agreement (this “Agreemen

MEDIACO HOLDING INC. Up to $2,031,019 Of Shares of Class A Common Stock

TABLE OF CONTENTS Filed Pursuant to Rule 424(b)(5) Registration No. 333-281481 PROSPECTUS SUPPLEMENT (To Prospectus dated December 6, 2024) MEDIACO HOLDING INC. Up to $2,031,019 Of Shares of Class A Common Stock This prospectus supplement and the accompanying base prospectus dated December 6, 2024 relate to the offering of up to $2.031 million of shares of our Class A common stock, par value $0.01

As filed with the Securities and Exchange Commission on December 3, 2024.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on December 3, 2024.

MEDIACO COMPLETES FULL REPAYMENT OF $7.3 MILLION CONVERTIBLE PROMISSORY NOTE

Exhibit 99.1 MEDIACO COMPLETES FULL REPAYMENT OF $7.3 MILLION CONVERTIBLE PROMISSORY NOTE November 26, 2024 – NEW YORK. MediaCo Holding Inc. (Nasdaq: MDIA) (“MediaCo”) a leading multicultural media company, announced today that it has fully repaid in cash the $7.3 million convertible promissory note (the “Convertible Note”) held by Emmis Communications Corporation. In connection with the satisfact

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): November 25, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inc

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL STATEMENTS

Exhibit 99.5 UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL STATEMENTS Asset Purchase Agreement On April 17, 2024, MediaCo Holding Inc., an Indiana corporation (“MediaCo” or “the Company”), and its wholly-owned subsidiary MediaCo Operations LLC, a Delaware limited liability company (“Purchaser”), entered into an asset purchase agreement (the “Asset Purchase Agreement”) with Estrella Broadcasting

As filed with the Securities and Exchange Commission on November 22, 2024.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on November 22, 2024.

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 2) Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): November 22, 2024 (April 16, 2024) Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-242777

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 0

Employee Leasing Agreement.

Exhibit 10.1 EMPLOYEE LEASING AGREEMENT THIS EMPLOYEE LEASING AGREEMENT (“Agreement”), dated as of October 1, 2024 (the “Effective Date”), is entered into by and between Standard Media Group LLC, a Delaware limited liability company (hereinafter “SMG”), and MediaCo Holding Inc., an Indiana corporation (hereinafter “MDIA”). BACKGROUND WHEREAS, from the Effective Date until terminated as set forth h

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): October 24, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inco

OUR MISSION MediaCo is a brand and content company reflecting, informing, and amplifying communities through culture, news, and entertainment.

Exhibit 99.1 OUR MISSION MediaCo is a brand and content company reflecting, informing, and amplifying communities through culture, news, and entertainment. OUR VISION To be the leading multicultural media company for the New America. OUR VALUES Represent: We reflect our community through diverse- owned, diverse-created, content that is uniquely connected to the New America. Influence: We drive inf

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 25, 2024 Mediaco Hold

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 25, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of

SEPARATION AND GENERAL RELEASE AGREEMENT

Exhibit 99.1 SEPARATION AND GENERAL RELEASE AGREEMENT This Separation and General Release Agreement (“Agreement”) is made by and between Ann Beemish (“you”) and MediaCo Holding Inc. (“MediaCo” or the “Company”). 1. Notification Date. On September 20, 2024, you resigned as the Company's Chief Financial Officer, and from any and all other officer positions with the Company and any subsidiaries there

INDEPENDENT CONTRACTOR CONSULTING AGREEMENT

Exhibit 99.2 INDEPENDENT CONTRACTOR CONSULTING AGREEMENT This Independent Contractor Consulting Agreement (“Agreement”) is made as of October 1, 2024, between MediaCo Holding Inc. (“MDIA”), 48 W 25th Street, Floor 3, New York, NY 10010 and Ann Beemish (”Consultant”), 201 E. 21st St., #15N, New York, NY 10010. In consideration of the mutual promises contained herein and other good and valuable cons

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 25, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of In

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 17, 2024 Mediaco Holdin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 17, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of In

Network Affiliation Agreement by and among MediaCo Operations LLC and Estrella Media, Inc., dated April 17, 2024.

Execution Version NETWORK AFFILIATION PROGRAM AGREEMENT This Network Affiliation Agreement (this “Agreement”), dated as of April 17, 2024, is made by and among MediaCo Operations LLC, a Delaware limited liability company (“Network”), Estrella Media, Inc.

Network Program Supply Agreement by and among MediaCo Operations LLC and Estrella Media, Inc., dated April 17, 2024.

NETWORK PROGRAM SUPPLY AGREEMENT This Network Program Supply Agreement (this “Agreement”), dated as of April 17, 2024, is made by and among MediaCo Operations LLC, a Delaware limited liability company (“Network”), Estrella Media, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39

Option Agreement by and among MediaCo Operations LLC, MediaCo Holding Inc., Estrella Broadcasting, Inc., Estrella Media, Inc., and the other parties named therein, dated April 17, 2024.

Execution Version OPTION AGREEMENT THIS OPTION AGREEMENT (this “Agreement”) is made and entered into as of April 17, 2024 by and among (i) MediaCo Operations LLC, a Delaware limited liability company (together with its successors and assigns, “Option Holder”), (ii) solely for purposes of Section 5(a) and Section 32(b) hereof, MediaCo Holding Inc.

First Amendment and Limited Consent to Credit Agreement dated as of September 10, 2024, by and between MediaCo Holding Inc., as Borrower, the financial institutions party thereto as lenders and WhiteHawk Capital Partners LP as Term Agent.

Exhibit 10.1 Execution Version FIRST AMENDMENT AND LIMITED CONSENT TO CREDIT AGREEMENT THIS FIRST AMENDMENT AND LIMITED CONSENT TO CREDIT AGREEMENT, dated as of September 10, 2024 (this “Amendment”), is by and among the Term Lenders identified on the signature pages hereof (each of such Term Lenders together with its successors and permitted assigns, a “Required Lender” and, collectively, the “Req

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 16, 2024 (September 10,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): September 16, 2024 (September 10, 2024) Mediaco Holding Inc. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or other jurisdiction of incorp

Limited Consent to Credit Agreement dated as of September 10, 2024, between MediaCo Holding Inc., as Borrower, the financial institutions party thereto as lenders and HPS Investment Partners, LLC, as Term Agent.

Exhibit 10.2 Execution Version LIMITED CONSENT TO CREDIT AGREEMENT THIS LIMITED CONSENT TO CREDIT AGREEMENT, dated as of September 10, 2024 (this “Limited Consent”), is by and among the Term Lenders identified on the signature pages hereof (each of such Term Lenders together with its successors and permitted assigns, a “Required Lender” and, collectively, the “Required Lenders”), HPS INVESTMENT PA

MediaCo Holding Inc. Receives Notification of Deficiency from Nasdaq Related to Delayed Filing of Quarterly Report on Form 10-Q

Exhibit 99.1 MediaCo Holding Inc. Receives Notification of Deficiency from Nasdaq Related to Delayed Filing of Quarterly Report on Form 10-Q AUGUST 20, 2024 – NEW YORK / LOS ANGELES – MediaCo Holding Inc. (Nasdaq: MDIA) (“MediaCo”) today announced that it received an expected deficiency notification letter from the Listing Qualifications Staff of The Nasdaq Stock Market LLC (“Nasdaq”) on August 20

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): August 20, 2024 Mediaco Holding I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): August 20, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING OMB APPROVAL OMB Number: 3235-0058 Expires: April 30, 2025 Estimated average burden hours per response ............ 2.50 SEC File Number: 001-39029 CUSIP Number: 58450D104 (Check one): ☐ Form 10-K ☐ Form 20-F ☐ Form 11-K ☒ Form 10-Q ☐ Form 10-D ☐ Form N-CEN ☐ Form N-CSR For Period Ended:

As filed with the Securities and Exchange Commission on August 12, 2024.

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on August 12, 2024.

Filing fee table.

Exhibit 107 Calculation of Filing Fee Tables FORM S-3 (Form Type) MEDIACO HOLDING INC.

MediaCo Holding Inc. 48 West 25th Street, Third Floor New York, New York 10010

MediaCo Holding Inc. 48 West 25th Street, Third Floor New York, New York 10010 July 23, 2024 VIA EDGAR TRANSMISSION Securities and Exchange Commission Division of Corporation Finance Office of Technology 100 F Street, N.E. Washington, D.C. 20549 Attention: Mitchell Austin, Esq. Re: MediaCo Holding Inc. Registration Statement on Form S-3 Filed July 12, 2024 (amended July 22, 2024) File No. 333-2807

As filed with the Securities and Exchange Commission on July 19, 2024.

As filed with the Securities and Exchange Commission on July 19, 2024. Registration No. 333‑280779 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to FORM S‑3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 MEDIACO HOLDING INC. (Exact Name of Registrant as Specified in Its Charter) Indiana (State or Other Jurisdiction of Incorporation or Organization

Exhibit 99.1 to Amendment No. 1 to the Registrant’s Current Report on Form 8-K filed with the Securities and Exchange Commission on July 3, 2024.

Exhibit 99.1 ESTRELLA MEDIACO BUSINESS GENERAL On April 17, 2024, MediaCo, through its wholly-owned subsidiary MediaCo Operations LLC, a Delaware limited liability company (“MediaCo Operations”), purchased substantially all of the assets of Estrella Broadcasting, Inc., a Delaware corporation (“Estrella Broadcasting”) and its subsidiaries (other than certain broadcasting assets owned by Estrella Br

As filed with the Securities and Exchange Commission on July 12, 2024.

As filed with the Securities and Exchange Commission on July 12, 2024. Registration No. 333‑ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S‑3 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 MEDIACO HOLDING INC. (Exact Name of Registrant as Specified in Its Charter) Indiana (State or Other Jurisdiction of Incorporation or Organization) 84-2427771 (I.R.S. Empl

Filing fee table.

Exhibit 107 CALCULATION OF FILING FEE TABLES Form S-3 (Form Type) MediaCo Holding Inc.

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): July 9, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 18, 2024 (April 16, 2024) Mediaco Holding Inc. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or other jurisdicti

Business Description

Exhibit 99.1 Business Description MEDIACO HOLDING INC. The business description of MediaCo Holding Inc., an Indiana corporation (“MediaCo”) is contained in MediaCo’s Annual Report on Form 10-K for the year ended December 31, 2023, which was filed with the Securities and Exchange Commission on April 1, 2024, and is incorporated herein by reference. ESTRELLA MEDIACO BUSINESS GENERAL On April 17, 202

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL STATEMENTS

Exhibit 99.4 UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL STATEMENTS Asset Purchase Agreement On April 17, 2024, MediaCo Holding Inc., an Indiana corporation (“MediaCo” or “the Company”), and its wholly-owned subsidiary MediaCo Operations LLC, a Delaware limited liability company (“Purchaser”), entered into an asset purchase agreement (the “Asset Purchase Agreement”) with Estrella Broadcasting

Estrella Broadcasting, Inc.

Exhibit 99.2 Estrella Broadcasting, Inc. Consolidated Financial Statements Years Ended December 31, 2023 and 2022 Estrella Broadcasting, Inc. Contents Independent Auditor’s Report 3-4 Consolidated Financial Statements Consolidated Balance Sheets 6-7 Consolidated Statements of Operations 8 Consolidated Statements of Changes in Shareholders’ Deficit 9 Consolidated Statements of Cash Flows 10 Notes t

Estrella Broadcasting, Inc. Condensed Consolidated Financial Statements As of March 31, 2024, and for the Three Months Ended March 31, 2024 and 2023 Estrella Broadcasting, Inc.

Exhibit 99.3 Estrella Broadcasting, Inc. Condensed Consolidated Financial Statements As of March 31, 2024, and for the Three Months Ended March 31, 2024 and 2023 Estrella Broadcasting, Inc. Contents Consolidated Financial Statements Consolidated Balance Sheets (Unaudited) 4-5 Consolidated Statements of Operations (Unaudited) 6 Consolidated Statements of Changes in Shareholders’ Deficit (Unaudited)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant  ☐ Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission only (as permitted by Rule

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-3

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K/A (Amendment No. 1) (Mark One) ☒ Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended December 31, 2023 ☐ Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name

Option Agreement, dated as of April 17, 2024, among MediaCo Operations LLC, solely for purposes of Section 5(a), MediaCo Holding Inc., Estrella Broadcasting, Inc., Estrella Media, Inc. and the grantor parties thereto.

EX-99.4 2 eh240473342ex04.htm EXHIBIT 99.4 EXHIBIT 4 Execution Version OPTION AGREEMENT THIS OPTION AGREEMENT (this “Agreement”) is made and entered into as of April 17, 2024 by and among (i) MediaCo Operations LLC, a Delaware limited liability company (together with its successors and assigns, “Option Holder”), (ii) solely for purposes of Section 5(a) and Section 32(b) hereof, MediaCo Holding Inc

Stockholders Agreement, dated as of April 17, 2024, among MediaCo Holding Inc., SLF LBI Aggregator, LLC and SG Broadcasting LLC

EX-99.5 3 eh240473342ex05.htm EXHIBIT 99.5 EXHIBIT 5 Corrected Execution Version MEDIACO HOLDINGS INC. STOCKHOLDERS AGREEMENT Dated as of April 17, 2024 Table of Contents Page Article I DEFINITIONS 1 Section 1.1 Definitions 1 Section 1.2 General Interpretive Principles 5 Article II REPRESENTATIONS AND WARRANTIES 5 Section 2.1 Representations and Warranties of the Investors 5 Section 2.2 Representa

MDIA / MediaCo Holding Inc. / Kapnick Scott - SCHEDULE 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 MediaCo Holding Inc. (Name of Issuer) Class A Common Stock, par value $0.01 per share (Title of Class of Securities) 58450D104 (CUSIP Number) Scott Kapnick HPS Group GP, LLC 40 West 57th Street, 33rd Floor New York, New York 10019 (212) 287-6767 (Name, Address and Telephon

Stockholders Agreement, by and among the Company, Aggregator, and SG Broadcasting, dated April 17, 2024

EX-99.2 2 ff3288018ex992-mediaco.htm Corrected Execution Version MEDIACO HOLDINGS INC. STOCKHOLDERS AGREEMENT Dated as of April 17, 2024 TABLE OF CONTENTS Article I DEFINITIONS 1 Section 1.1 Definitions 1 Section 1.2 General Interpretive Principles 5 Article II REPRESENTATIONS AND WARRANTIES 5 Section 2.1 Representations and Warranties of the Investors 5 Section 2.2 Representations and Warranties

MDIA / MediaCo Holding Inc. / Standard General L.P. Activist Investment

SC 13D/A 1 ff328801813da17-mediaco.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 17)* MediaCo Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-25

Articles of Amendment to Amended & Restated Articles of Incorporation of MediaCo Holding Inc., dated April 17, 2024; incorporated by reference to Exhibit 3.1 to the Registrant’s Current Report on Form 8-K filed with the Securities and Exchange Commission on April 18, 2024.

Exhibit 3.1 ARTICLES OF AMENDMENT TO AMENDED & RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. April 17, 2024 MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), does hereby certify that, pursuant to authority conferred upon the Board of Directors of the Corporation (the “Board of Directors”) by Article VIII of the Amend

MEDIACO ACQUIRES ESTRELLA MEDIA’S CONTENT AND DIGITAL OPERATIONS Transaction Will Create One of the Largest Multicultural Media Platforms in the Country.

Exhibit 99.1 MEDIACO ACQUIRES ESTRELLA MEDIA’S CONTENT AND DIGITAL OPERATIONS Transaction Will Create One of the Largest Multicultural Media Platforms in the Country. APRIL 18, 2024 – NEW YORK / LOS ANGELES – MediaCo Holding Inc. (Nasdaq: MDIA) (“MediaCo”) today announced that it has acquired all of Estrella Media’s network, content, digital, and commercial operations. Among the Estrella Media bra

holders Agreement by and among MediaCo Holding Inc., SLF LBI Aggregator, LLC, and SG Broadcasting LLC, dated April 17, 2024.

Exhibit 10.4 Execution Version MEDIACO HOLDING INC. STOCKHOLDERS AGREEMENT Dated as of April 17, 2024 TABLE OF CONTENTS Page Article I DEFINITIONS 1 Section 1.1 Definitions 1 Section 1.2 General Interpretive Principles 5 Article II REPRESENTATIONS AND WARRANTIES 5 Section 2.1 Representations and Warranties of the Investors 5 Section 2.2 Representations and Warranties of the Company 6 Article III H

Second Lien Term Loan Agreement dated as of April 17, 2024, between MediaCo Holding Inc., as Borrower, the financial institutions party thereto as lenders and HPS Investment Partners, LLC as Term Agent.

Exhibit 10.3 EXECUTION VERSION **************************************** SECOND LIEN TERM LOAN AGREEMENT Dated as of April 17, 2024 by and among MEDIACO HOLDING INC., THE OTHER PERSONS PARTY HERETO THAT ARE DESIGNATED AS BORROWERS, THE FINANCIAL INSTITUTIONS PARTY HERETO, as Term Lenders, and HPS INVESTMENT PARTNERS, LLC as Term Agent **************************************** TABLE OF CONTENTS ARTIC

Asset Purchase Agreement by and among MediaCo Holding Inc., MediaCo Operations LLC, Estrella Broadcasting, Inc., and SLF LBI Aggregator, LLC, dated April 17, 2024.

Exhibit 2.1 EXECUTION VERSION ASSET PURCHASE AGREEMENT DATED AS OF APRIL 17, 2024 BY AND AMONG MEDIACO HOLDING INC., AS PARENT, MEDIACO OPERATIONS LLC, AS THE PURCHASER, ESTRELLA BROADCASTING, INC., AS THE COMPANY, AND SOLELY FOR PURPOSES OF SECTIONS 3.3(c), 8.1, 8.2, 8.8 AND 8.14 HEREIN SLF LBI AGGREGATOR, LLC THE COMPANY AGGREGATOR TABLE OF CONTENTS Page ARTICLE 1. DEFINITIONS 2 1.1 Definitions

Registration Rights Agreement by and among MediaCo Holding Inc., SG Broadcasting LLC, and SLF LBI Aggregator, LLC, dated April 17, 2024.

Exhibit 10.5 Execution Version REGISTRATION RIGHTS AGREEMENT by and among MEDIACO HOLDING INC. and THE HOLDERS PARTY HERETO Dated as of April 17, 2024 TABLE OF CONTENTS ARTICLE I RESALE SHELF REGISTRATION Section 1.1 Resale Shelf Registration Statement 1 Section 1.2 Effectiveness Period 2 Section 1.3 Subsequent Shelf Registration Statement 2 Section 1.4 Supplements and Amendments 2 Section 1.5 Sub

Class A common stock Purchase Warrant issued by MediaCo Holding Inc. to SLF LBI Aggregator, LLC, dated April 17, 2024.

Exhibit 4.1 EXECUTION VERSION THIS WARRANT AND THE SECURITIES ISSUABLE UPON EXERCISE OF THIS WARRANT HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933 (THE “SECURITIES ACT”) AND MAY NOT UNDER ANY CIRCUMSTANCES BE SOLD, TRANSFERRED OR OTHERWISE DISPOSED OF WITHOUT AN EFFECTIVE REGISTRATION STATEMENT FOR SUCH SECURITIES UNDER THE SECURITIES ACT AND ANY OTHER APPLICABLE LAWS OR AN OPINION OF

Voting and Support Agreement, by and among Estrella Broadcasting, Inc., MediaCo Holding, Inc., and SG Broadcasting LLC, dated April 17, 2024.

Exhibit 10.1 Execution Version VOTING AND SUPPORT AGREEMENT This VOTING AND SUPPORT AGREEMENT (this “Agreement”) is entered into as of April 17, 2024, by and among Estrella Broadcasting, Inc., a Delaware corporation (the “Company”), MediaCo Holding Inc., an Indiana corporation (“Parent”), and SG Broadcasting LLC, a Delaware limited liability company (the “SG Stockholder”). W I T N E S S E T H: WHE

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 18, 2024 (April 16, 2024) M

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 18, 2024 (April 16, 2024) Mediaco Holding Inc. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or other jurisdiction of incorporation)

Term Loan Agreement dated as of April 17, 2024, between MediaCo Holding Inc., as Borrower, the financial institutions party thereto as lenders and WhiteHawk Capital Partners LP as Term Agent.

Exhibit 10.2 Execution Version **************************************** TERM LOAN AGREEMENT Dated as of April 17, 2024 by and among MEDIACO HOLDING INC. THE OTHER PERSONS PARTY HERETO THAT ARE DESIGNATED AS BORROWERS, THE FINANCIAL INSTITUTIONS PARTY HERETO, as Term Lenders, and WHITEHAWK CAPITAL PARTNERS LP as Term Agent **************************************** TABLE OF CONTENTS ARTICLE I. THE TE

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): April 8, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpo

MDIA / MediaCo Holding Inc. / Standard General L.P. - AMENDMENT NO. 16 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 16)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Num

Subsidiaries of MediaCo Holding Inc.

Exhibit 21 INFORMATION REGARDING SUBSIDIARIES OF THE REGISTRANT Name Under Which Subsidiary Does Business Jurisdiction of Organization MediaCo Holding Inc. IN MediaCo WQHT License LLC IN MediaCo WBLS License LLC IN

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended December 31, 2023 o Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as sp

MediaCo Holding Inc. Compensation Recoupment Policy

Exhibit 97 MEDIACO HOLDING, INC. COMPENSATION RECOUPMENT POLICY The Compensation Committee (the “Committee”) of the Board of Directors (the “Board”) of MediaCo Holding Inc. (the “Company”) has adopted this Compensation Recoupment Policy (this “Policy”) in order to implement a mandatory clawback policy in the event of a Restatement in compliance with the Applicable Rules (each, as defined below), a

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): March 14, 2024 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorp

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 0

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): October 11, 2023 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inco

Separation Agreement

Exhibit 99.1 Separation Agreement October 11, 2023 Rahsan-Rahsan Lindsay 412 Sterling Place Brooklyn, NY 11238 Dear Rahsan: This letter agreement (the “Agreement”) will confirm the following terms in connection with your separation of employment from MediaCo Holding Inc. (the “Company”). You must sign this Agreement today, October 11, 2023, to obtain the benefits described herein. 1. Separation an

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): September 15, 2023 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of In

MDIA / MediaCo Holding Inc - Class A / Standard General L.P. - AMENDMENT NO. 15 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 15)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Num

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): August 9, 2023 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorp

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39

Separation and Release Agreement

Exhibit 99.1 Separation and Release Agreement July 11, 2023 Bradford Tobin 10 Nevins Street Apartment 25i Brooklyn, NY 11217 Dear Brad: This letter agreement (the “Agreement”) will confirm the following terms in connection with your separation of employment from MediaCo Holding Inc. (the “Company”): 1. Separation, Transition, and Consulting Period – If you sign, return, and do not revoke this Agre

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): July 11, 2023 Mediaco Holding Inc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): July 11, 2023 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpo

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): June 20, 2023 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-3

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant  ☐ Check the appropriate box:  ☐ Preliminary Proxy Statement  ☐ Confidential, for Use of the Commission only (as permitted by Rule

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) x Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended December 31, 2022 o Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as sp

Subsidiaries of MediaCo Holding Inc.

Exhibit 21 INFORMATION REGARDING SUBSIDIARIES OF THE REGISTRANT Name Under Which Subsidiary Does Business Jurisdiction of Organization MediaCo Holding Inc. IN MediaCo WQHT License LLC IN MediaCo WBLS License LLC IN FMG Kentucky, LLC DE FMG Valdosta, LLC DE Fairway Outdoor LLC DE

Articles of Amendment to Amended & Restated Articles of Incorporation of MediaCo Holding Inc., dated March 23, 2023; incorporated by reference to Exhibit 3.1 to the Registrant’s Current Report on Form 8-K filed with the Securities and Exchange Commission on March 27, 2023.

Exhibit 3.1 ARTICLES OF AMENDMENT TO ARTICLES OF AMENDMENT OF AMENDED & RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. March 23, 2023 MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), does hereby certify that, pursuant to authority conferred upon the Board of Directors (the “Board”) by Article VIII of the Amended and

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): March 23, 2023 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorp

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): December 28, 2022 Mediaco Holding

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): December 28, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inc

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. - AMENDMENT NO. 14 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 14)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Num

MDIA / Mediaco Holding Inc. Class A / EMMIS COMMUNICATIONS CORP - SC 13D/A Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 1) MEDIACO HOLDING, INC. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) J. Scott Enright Emmis Corporation One Emmis Plaza 40 Monument Circle, Suite 700 Indianapolis, Indiana 46204 (317) 266-0100 (Name, Address and Telephon

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): December 14, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inc

ASSET PURCHASE AGREEMENT BY AND AMONG THE LAMAR COMPANY, L.L.C., FAIRWAY OUTDOOR LLC FMG KENTUCKY, LLC FMG VALDOSTA, LLC DATED AS OF DECEMBER 9, 2022 TABLE OF CONTENTS

Exhibit 2.1 ASSET PURCHASE AGREEMENT BY AND AMONG THE LAMAR COMPANY, L.L.C., FAIRWAY OUTDOOR LLC FMG KENTUCKY, LLC AND FMG VALDOSTA, LLC DATED AS OF DECEMBER 9, 2022 TABLE OF CONTENTS PAGE ARTICLE I PURCHASE AND SALE 1 1.1 Purchase and Sale of Purchased Assets 1 1.2 Excluded Assets 3 1.3 Assumed Liabilities 4 1.4 Excluded Liabilities 4 1.5 Purchase Price 5 1.6 Closing Payments 5 1.7 Adjustment of

UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL STATEMENTS

Exhibit 99.2 UNAUDITED PRO FORMA CONDENSED CONSOLIDATED FINANCIAL STATEMENTS On December 9, 2022, Fairway Outdoor LLC, FMG Kentucky, LLC and FMG Valdosta, LLC (collectively, the “Sellers”), all of which are wholly owned direct and indirect subsidiaries of MediaCo Holding Inc. (the “Company”), entered into an Asset Purchase Agreement (the “Purchase Agreement”), with The Lamar Company, L.L.C., a Lou

MediaCo Holding Inc. Divests Fairway Outdoor to Lamar

Exhibit 99.1 MediaCo Holding Inc. Divests Fairway Outdoor to Lamar For Immediate Release December 12, 2022 New York, NY – MediaCo Holding Inc. (“MediaCo”) (NASDAQ: MDIA) announced today that it has divested the assets of Fairway Outdoor LLC, its out-of-home advertising division located across the eastern United States, to Lamar Advertising Company (“Lamar”) (NASDAQ: LAMR) for $78.6 million. The sa

Asset Purchase Agreement, dated as of December 9, 2022, by and among Fairway Outdoor LLC, FMG Kentucky, LLC and FMG Valdosta, LLC and The Lamar Company, L.L.C., a Louisiana limited liability company.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): December 9, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inco

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): December 2, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inco

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): November 15, 2022 Mediaco Holding

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): November 15, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inc

, 2022, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.

Exhibit 10.1 Proposed Execution Version AMENDMENT NO. 5 TO AMENDED AND RESTATED TERM LOAN AGREEMENT AMENDMENT NO. 5 TO AMENDED AND RESTATED TERM LOAN AGREEMENT, dated as of November 12, 2022 (this ?Amendment No. 5?), is by and among MEDIACO HOLDING INC., an Indiana corporation (?MediaCo?), MEDIACO WQHT LICENSE LLC, an Indiana limited liability company (?MediaCo WQHT?) and MEDIACO WBLS LICENSE LLC,

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 0

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. - AMENDMENT NO. 13 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 13)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Num

Unregistered Sales of Equity Securities, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): July 26, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No.   )

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ??) Filed by the Registrant ? Filed by a party other than the Registrant ?? Check the appropriate box: ?? Preliminary Proxy Statement ?? Confidential, for Use of the Commission only (as permitted by Ru

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. - AMENDMENT NO. 12 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 12)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Num

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of

Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): June 2, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39029 MEDIACO HOLDI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEFA14A 1 defa14a.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Co

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934

DEF 14A 1 def14a.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Con

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): April 1, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Incorpo

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. - AMENDMENT NO. 11 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 11)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Num

Amendment No. 1 to Unsecured Convertible Promissory Note, dated as of March 18, 2022, by and between MediaCo Holding Inc., and SG Broadcasting LLC.

Exhibit 10.12 AMENDMENT NO. 1 TO UNSECURED CONVERTIBLE PROMISSORY NOTE THIS AMENDMENT NO. 1 TO UNSECURED CONVERTIBLE PROMISSORY NOTE (this ?Amendment?), dated as of March [?], 2022, is by and between MediaCo Holding Inc., an Indiana corporation (the ?Company?), and SG Broadcasting LLC, a Delaware limited liability company (the ?Holder?). BACKGROUND WHEREAS, the Company issued to the Holder that ce

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended December 31, 2021 ? Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as sp

Subsidiaries of MediaCo Holding Inc.

Exhibit 21 INFORMATION REGARDING SUBSIDIARIES OF THE REGISTRANT Name Under Which Subsidiary Does Business Jurisdiction of Organization MediaCo Holding Inc. IN MediaCo WQHT License LLC IN MediaCo WBLS License LLC IN FMG Kentucky, LLC DE FMG Valdosta, LLC DE Fairway Outdoor LLC DE

Amended and Restated Code of Bylaws of MediaCo Holding Inc.

Exhibit 3.2 AMENDED AND RESTATED CODE OF BY-LAWS OF MEDIACO HOLDING INC. ARTICLE 1 Identification And Offices Section 1.1 Name. The name of the Corporation is MediaCo Holding Incorporated (hereinafter referred to as the "Corporation"). Section 1.2 Registered Office. The registered office and registered agent of the Corporation is as provided and designated in the Corporation?s Amended and Restated

EMPLOYMENT AGREEMENT

Exhibit 99.1 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (the ?Agreement?) is made and entered into effective February 9, 2022 (the ?Effective Date?), by and between MEDIACO HOLDING INC., an Indiana corporation, (?Employer? or ?MediaCo?), and ANN BEEMISH, a New York resident (?Executive?). RECITALS WHEREAS, Employer and its subsidiaries and affiliates are engaged in the ownership and operation

EMPLOYMENT AGREEMENT

Exhibit 99.2 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (the ?Agreement?) is made and entered into effective February 9, 2022 (the ?Effective Date?), by and between MEDIACO HOLDING INC., an Indiana corporation, (?Employer? or ?MediaCo?), and BRADFORD TOBIN, a New York resident (?Executive?). RECITALS WHEREAS, Employer and its subsidiaries and affiliates are engaged in the ownership and operati

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K Current Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of Earliest Event Reported): February 9, 2022 Mediaco Holding Inc. (Exact Name of Registrant as Specified in Its Charter) 001-39029 (Commission File Number) Indiana 84-2427771 (State or Other Jurisdiction of Inco

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. - AMENDMENT NO. 10 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 10)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Num

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. - AMENDMENT NO. 9 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 9)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. - AMENDMENT NO. 8 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 8)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): November 12, 2021 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission F

MEDIACO APPOINTS ANN BEEMISH AS CHIEF FINANCIAL OFFICER Ann C. Beemish Joins Executive Leadership Team to Continue MediaCo’s Growth and Expansion as a National Media Company and a Voice of Black Culture

EXHIBIT 99.1 MEDIACO APPOINTS ANN BEEMISH AS CHIEF FINANCIAL OFFICER Ann C. Beemish Joins Executive Leadership Team to Continue MediaCo?s Growth and Expansion as a National Media Company and a Voice of Black Culture New York, NY - Thursday, November 18, 2021 - MediaCo Holding Inc. (NASDAQ: MDIA), owner of HOT 97, WBLS, and Fairway Outdoor, announced today the appointment of Ann C. Beemish to the r

Employment Agreement, effective as of July 1, 2021, by and between MediaCo Holding Inc. and Rahsan-Rahsan Lindsay

Exhibit 10.1 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (the ?Agreement?) is made and entered into effective July 1, 2021 (the ?Effective Date?), by and between MEDIACO HOLDING INC., an Indiana corporation, (?Employer? or ?MediaCo?), and RAHSAN-RAHSAN LINDSAY, a New York resident (?Executive?). RECITALS WHEREAS, Employer and its subsidiaries and affiliates are engaged in the ownership and oper

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2021 ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39029 MEDIACO H

MEDIACO HOLDING INC. Up to $12,475,000 Class A Common Stock

Table of Contents Filed Pursuant to Rule 424(b)(5) Registration No. 333-258593 PROSPECTUS SUPPLEMENT (To Prospectus dated August 13, 2021) MEDIACO HOLDING INC. Up to $12,475,000 Class A Common Stock On August 20, 2021, we entered into an At Market Issuance Sales Agreement, or the sales agreement, with B. Riley Securities, Inc., or the Agent, relating to the offering of up to $12.475 million of sha

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 20, 2021 MediaCo Holding I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): August 20, 2021 MediaCo Holding Inc. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or other jurisdiction of incorporation) (Commission Fil

MEDIACO HOLDING INC. Class A Common Stock (par value $0.01 per share) At Market Issuance Sales Agreement

Exhibit 99.1 MEDIACO HOLDING INC. Class A Common Stock (par value $0.01 per share) At Market Issuance Sales Agreement August 20, 2021 B. Riley Securities, Inc. 299 Park Avenue, 21st Floor New York, NY 10171 Ladies and Gentlemen: MediaCo Holding Inc., an Indiana corporation (the ?Company?), confirms its agreement (this ?Agreement?) with B. Riley Securities, Inc. (the ?Agent?) as follows: 1. Issuanc

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2021 ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number 001-39029 MEDIACO HOLDIN

LETTER

United States securities and exchange commission logo August 11, 2021 Rahsan-Rahsan Lindsay Chief Executive Officer Mediaco Holding Inc.

MEDIACO HOLDING INC.

MEDIACO HOLDING INC. August 11, 2021 VIA EDGAR TRANSMISSION Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549 Attention: Matthew Crispino, Esq. Re: MediaCo Holding Inc. Registration Statement on Form S-3 Filed August 6, 2021 File No. 333-258593 Ladies and Gentlemen: Pursuant to Rule 461 under the Securities Act of 1933, as amended, MediaCo

As filed with the Securities and Exchange Commission on August 6, 2021.

Table of Contents As filed with the Securities and Exchange Commission on August 6, 2021.

MEDIACO APPOINTS NEW EXECUTIVE TEAM TO LEAD STRATEGIC REALIGNMENT AND INNOVATION RAHSAN-RAHSAN LINDSAY NAMED CHIEF EXECUTIVE OFFICER OF MEDIACO: HOT 97, WBLS, AND FAIRWAY OUTDOOR; BRADFORD TOBIN NAMED PRESIDENT AND COO Company Appoints New Seasoned L

Exhibit 99.1 MEDIACO APPOINTS NEW EXECUTIVE TEAM TO LEAD STRATEGIC REALIGNMENT AND INNOVATION RAHSAN-RAHSAN LINDSAY NAMED CHIEF EXECUTIVE OFFICER OF MEDIACO: HOT 97, WBLS, AND FAIRWAY OUTDOOR; BRADFORD TOBIN NAMED PRESIDENT AND COO Company Appoints New Seasoned Leadership in Key Roles to Fuel Growth and Continued Service to Black Culture and the Hip Hop Community (New York, NY) - June 11, 2021 - M

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 21, 2021 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission File N

As filed with the Securities and Exchange Commission on May 24, 2021.

As filed with the Securities and Exchange Commission on May 24, 2021. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 MediaCo Holding Inc. (Exact Name of Registrant as Specified in Its Charter) Indiana (State or other Jurisdiction of Incorporation or organization) 84-2427771 (IRS Employer I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 Commission File Number 001-39029 M

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2021 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 84-2427771 (I.R.S. Employe

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 7)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 7)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

Unsecured Convertible Promissory Note, dated as of May 19, 2021, by MediaCo Holding Inc. in favor of SG Broadcasting LLC.

Exhibit 10.2 THIS INSTRUMENT AND THE RIGHTS AND OBLIGATIONS EVIDENCED HEREBY ARE SUBORDINATE IN THE MANNER AND TO THE EXTENT SET FORTH IN THAT CERTAIN THIRD AMENDED AND RESTATED SHAREHOLDER NOTE SUBORDINATION AGREEMENT (AS AMENDED, MODIFIED, RESTATED OR REPLACED FROM TIME TO TIME, THE ?SUBORDINATION AGREEMENT?), DATED AS OF MAY 19, 2021, BETWEEN SG BROADCASTING LLC AND GACP FINANCE CO., LLC, IN IT

Report of Independent Registered Public Accounting Firm

Exhibit 99.1 ITEM 1A. RISK FACTORS. The risk factors listed below, in addition to those set forth elsewhere in this report, could affect the business, financial condition and future results of the Company. Additional risks and uncertainties that are not currently known to the Company or that are not currently believed by the Company to be material may also harm the Company?s business, financial co

Amendment No. 4 and Waiver to Amended and Restated Term Loan Agreement, dated as of May 19, 2021, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.

Exhibit 10.1 EXECUTION VERSION AMENDMENT NO. 4 AND WAIVER TO AMENDED AND RESTATED TERM LOAN AGREEMENT AMENDMENT NO. 4 AND WAIVER TO AMENDED AND RESTATED TERM LOAN AGREEMENT, dated as of May 19, 2021, and effective March 31, 2021 (this ?Amendment No. 4?), is by and among MEDIACO HOLDING INC., an Indiana corporation (?MediaCo?), MEDIACO WQHT LICENSE LLC, an Indiana limited liability company (?MediaC

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 19, 2021 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission File N

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING OMB APPROVAL OMB Number: 3235-0058 Expires: February 28, 2022 Estimated average burden hours per response ............ 2.50 SEC File Number: 001-39029 CUSIP Number: 58450D104 (Check one): ? Form 10-K ? Form 20-F ? Form 11-K ? Form 10-Q ? Form 10-D ? Form N-CEN ? Form N-CSR For Period End

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 13, 2021 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission File N

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of

MediaCo Holding Inc. 2021 Equity Compensation Plan

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confid

Amended and Restated Code of Bylaws of MediaCo Holding Inc.

Exhibit 3.2 3-30-21 AMENDED AND RESTATED CODE OF BY-LAWS OF MEDIACO HOLDING INC. ARTICLE 1 Identification And Offices Section 1.1Name. The name of the Corporation is MediaCo Holding Incorporated (hereinafter referred to as the ?Corporation?). Section 1.2Registered Office. The registered office and registered agent of the Corporation is as provided and designated in the Corporation?s Amended and Re

Subsidiaries of MediaCo Holding Inc.

Exhibit 21 INFORMATION REGARDING SUBSIDIARIES OF THE REGISTRANT Name Under Which Subsidiary Does Business Jurisdiction of Organization MediaCo Holding Inc. IN MediaCo WQHT License LLC IN MediaCo WBLS License LLC IN FMG Kentucky, LLC DE FMG Valdosta, LLC DE Fairway Outdoor LLC DE

Annual Report - 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ? Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended December 31, 2020 ? Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as sp

Powers of Attorney

Exhibit 24 POWER OF ATTORNEY KNOW ALL MEN BY THESE PRESENTS, that the person whose signature appears below, hereby constitutes and appoints Jeffrey H.

- PRE 14A

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confid

- 8-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): January 1, 2021 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission Fil

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2020 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 84-2427771 (I.R.S. Emp

58450D104 / Mediaco Holding Inc / Standard General L.P. - AMENDMENT NO. 6 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 6)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

58450D104 / Mediaco Holding Inc / Standard General L.P. - AMENDMENT NO. 5 Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 5)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant - MEDIACO 8-K AUGUST 31, 2020

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): August 28, 2020 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission Fil

Amendment No. 3 to Amended and Restated Term Loan Agreement, dated as of August 28, 2020, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.

Exhibit 10.1 AMENDMENT NO. 3 TO AMENDED AND RESTATED TERM LOAN AGREEMENT AMENDMENT NO. 3 TO AMENDED AND RESTATED TERM LOAN AGREEMENT, dated as of August 28, 2020 (this “Amendment No. 3”), is by and among MEDIACO HOLDING INC., an Indiana corporation (“MediaCo”), MEDIACO WQHT LICENSE LLC, an Indiana limited liability company (“MediaCo WQHT”) and MEDIACO WBLS LICENSE LLC, an Indiana limited liability

- S-8 AUGUST 14, 2020

As filed with the Securities and Exchange Commission on August 14, 2020. Registration No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM S-8 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 MediaCo Holding Inc. (Exact Name of Registrant as Specified in Its Charter) Indiana (State or other Jurisdiction of Incorporation or organization) 84-2427771 (IRS Employe

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2020 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 84-2427771 (I.R.S. Employer

Form of Restricted Stock Agreement under 2020 Equity Compensation Plan.

Exhibit 10.2 RESTRICTED STOCK AGREEMENT Shares of Restricted Stock are awarded, effective as of the Date of Grant (as defined below), by MediaCo Holding Inc. (the “Company”) to the person named below (the “Grantee”) upon the following terms and conditions. The Grantee will be deemed to have accepted the Restricted Stock unless the Grantee delivers a written notice of rejection to the Company withi

Management Agreement, effective August 1, 2020, between Fairway Outdoor LLC and Billboards LLC.

Exhibit 10.3 MANAGEMENT AGREEMENT MANAGEMENT AGREEMENT (the “Agreement”) effective August 1, 2020 (the “Agreement Date”) by and between Billboards LLC, a Delaware limited liability company (the “Billboards LLC”), and Fairway Outdoor LLC, a Delaware limited liability company (“Manager”). BACKGROUND Billboards LLC wishes to retain and engage Manager to provide management services to Billboards LLC a

58450D104 / Mediaco Holding Inc / Francis Capital Management, Llc Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* MediaCo Holding, Inc. (Name of Issuer) Common Stock, par value $0.01 (Title of Class of Securities) 58450D104 (CUSIP Number) June 17, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant

Joint Filing Agreement

Exhibit 99.1 JOINT FILING AGREEMENT Emmis Communications Corporation and Jeffrey H. Smulyan (collectively, the "Filers") agree as of June 5, 2020 as follows: Each of the Filers may be required to file with the United States Securities and Exchange Commission a statement on Schedule 13D and/or 13G with respect to shares of Class A Common Stock, $0.01 par value per share, of Medico Holding Inc. that

58450D104 / Mediaco Holding Inc / EMMIS COMMUNICATIONS CORP - SC 13D Activist Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 MEDIACO HOLDING, INC. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) J. Scott Enright Emmis Communications Corporation One Emmis Plaza 40 Monument Circle, Suite 700 Indianapolis, Indiana 46204 (317) 266-0100 (Name, Address and Telephone Num

58450D104 / Mediaco Holding Inc / Standard General L.P. Activist Investment

SC 13D/A 1 sch13d.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 4)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Addr

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): May 14, 2020 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission File N

Quarterly Report - 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2020 Commission File Number 001-39029 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 84-2427771 (I.R.S. Employe

- DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of

Entry into a Material Definitive Agreement, Termination of a Material Definitive Agreement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): April 22, 2020 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) Indiana 001-39029 84-2427771 (State or Other Jurisdiction of Incorporation) (Commission File

Loan Proceeds Participation Agreement, dated April 22, 2020, between MediaCo Holding Inc. and Emmis Operating Company.

Exhibit 10.1 LOAN PROCEEDS PARTICIPATION AGREEMENT This Loan Proceeds Participation Agreement (this “Agreement”) is entered into by and between Emmis Operating Company, an Indiana corporation (“Emmis”), and MediaCo Holding Inc., an Indiana corporation (“MediaCo”), effective as of April 22, 2020. Emmis and MediaCo shall sometimes be referred to individually as a “Party” and together as “Parties”. W

Loan Proceeds Participation Agreement, dated April 22, 2020, between MediaCo Holding Inc. and Emmis Operating Company.

Exhibit 10.1 LOAN PROCEEDS PARTICIPATION AGREEMENT This Loan Proceeds Participation Agreement (this “Agreement”) is entered into by and between Emmis Operating Company, an Indiana corporation (“Emmis”), and MediaCo Holding Inc., an Indiana corporation (“MediaCo”), effective as of April 22, 2020. Emmis and MediaCo shall sometimes be referred to individually as a “Party” and together as “Parties”. W

58450D104 / Mediaco Holding Inc / Standard General L.P. Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

58450D104 / Mediaco Holding Inc / Francis Capital Management, Llc Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* MediaCo Holding, Inc. (Name of Issuer) Common Stock, par value $0.01 (Title of Class of Securities) 58450D104 (CUSIP Number) March 18, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant

MDIA / Mediaco Holding Inc. Class A DEFA14A - - DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of

MediaCo Holding Inc. 2020 Equity Compensation Plan (incorporated by reference to Exhibit A to the Registrant’s Definitive Proxy Statement for its 2020 Annual Meeting of Shareholders, filed with the Securities and Exchange Commission on April 3, 2020).

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confid

58450D104 / Mediaco Holding Inc / Standard General L.P. Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

Form 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☐ Annual Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Fiscal Year Ended ☒ Transition Report Pursuant to Section 13 or 15(d) of The Securities Exchange Act of 1934 for the Transition Period from March 1, 2019 to December 31, 2019. Commission File Number 001-39029 MED

Amended and Restated Articles of Incorporation of MediaCo Holding Inc., as amended.

Exhibit 3.1 AMENDED AND RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. These Amended and Restated Articles of Incorporation (the “Articles”) of MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), which was duly incorporated as of June 27, 2019, hereby amend, restate and replace the previously existing Articles of Incorp

Amended and Restated Articles of Incorporation of MediaCo Holding Inc., as amended.

Exhibit 3.1 AMENDED AND RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. These Amended and Restated Articles of Incorporation (the “Articles”) of MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), which was duly incorporated as of June 27, 2019, hereby amend, restate and replace the previously existing Articles of Incorp

Amended and Restated Articles of Incorporation of MediaCo Holding Inc., as amended.

Exhibit 3.1 AMENDED AND RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. These Amended and Restated Articles of Incorporation (the “Articles”) of MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), which was duly incorporated as of June 27, 2019, hereby amend, restate and replace the previously existing Articles of Incorp

Description of Capital Stock

Exhibit 4.1 DESCRIPTION OF CAPITAL STOCK Common Stock General. Our authorized common stock consists of 170,000,000 shares of Class A Common Stock, $.01 par value per share, 50,000,000 shares of Class B Common Stock, $.01 par value per share, and 30,000,000 shares of Class C Common Stock, $.01 par value per share. Under Indiana law, shareholders are generally not liable for our debts or obligations

Subsidiaries of MediaCo Holding Inc.

EX-21 6 ck0001784254-ex217.htm EX-21 SUBSIDIARIES OF MEDIACO Exhibit 21 INFORMATION REGARDING SUBSIDIARIES OF THE REGISTRANT Name Under Which Subsidiary Does Business Jurisdiction of Organization MediaCo Holding Inc. IN MediaCo WQHT License LLC IN MediaCo WBLS License LLC IN FMG Kentucky, LLC DE FMG Valdosta, LLC DE Fairway Outdoor LLC DE

Amended and Restated Promissory Note, dated as of March 27, 2020, by MediaCo Holding Inc. in favor of SG Broadcasting LLC.

Exhibit 10.19 This instrument and the rights and obligations evidenced hereby are subordinate in the manner and to the extent set forth in that certain Second Amended and Restated Shareholder Note Subordination Agreement (as amended, modified, restated or replaced from time to time, the “Subordination Agreement”), dated as of March 27, 2020, between SG BROADCASTING LLC and GACP FINANCE CO., LLC, i

Powers of Attorney

Exhibit 24 POWER OF ATTORNEY KNOW ALL MEN BY THESE PRESENTS, that the person whose signature appears below, hereby constitutes and appoints Jeffrey H.

Subsidiaries of MediaCo Holding Inc.

EX-21 6 ck0001784254-ex217.htm EX-21 SUBSIDIARIES OF MEDIACO Exhibit 21 INFORMATION REGARDING SUBSIDIARIES OF THE REGISTRANT Name Under Which Subsidiary Does Business Jurisdiction of Organization MediaCo Holding Inc. IN MediaCo WQHT License LLC IN MediaCo WBLS License LLC IN FMG Kentucky, LLC DE FMG Valdosta, LLC DE Fairway Outdoor LLC DE

Amendment No. 2 to Amended and Restated Term Loan Agreement, dated as of March 27, 2020, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.

Exhibit 10.20 AMENDMENT NO. 2 TO AMENDED AND RESTATED TERM LOAN AGREEMENT AMENDMENT NO. 2 TO AMENDED AND RESTATED TERM LOAN AGREEMENT, dated as of March 27, 2020 (this “Amendment No. 2”), is by and among MEDIACO HOLDING INC., an Indiana corporation (“MediaCo”), MEDIACO WQHT LICENSE LLC, an Indiana limited liability company (“MediaCo WQHT”) and MEDIACO WBLS LICENSE LLC, an Indiana limited liability

Description of Capital Stock

Exhibit 4.1 DESCRIPTION OF CAPITAL STOCK Common Stock General. Our authorized common stock consists of 170,000,000 shares of Class A Common Stock, $.01 par value per share, 50,000,000 shares of Class B Common Stock, $.01 par value per share, and 30,000,000 shares of Class C Common Stock, $.01 par value per share. Under Indiana law, shareholders are generally not liable for our debts or obligations

Amended and Restated Promissory Note, dated as of March 27, 2020, by MediaCo Holding Inc. in favor of SG Broadcasting LLC.

Exhibit 10.19 This instrument and the rights and obligations evidenced hereby are subordinate in the manner and to the extent set forth in that certain Second Amended and Restated Shareholder Note Subordination Agreement (as amended, modified, restated or replaced from time to time, the “Subordination Agreement”), dated as of March 27, 2020, between SG BROADCASTING LLC and GACP FINANCE CO., LLC, i

Powers of Attorney

Exhibit 24 POWER OF ATTORNEY KNOW ALL MEN BY THESE PRESENTS, that the person whose signature appears below, hereby constitutes and appoints Jeffrey H.

MDIA / Mediaco Holding Inc. Class A PRE 14A - - PRE 14A

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (Rule 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION PROXY STATEMENT PURSUANT TO SECTION 14(a) OF THE SECURITIES EXCHANGE ACT OF 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confid

Amended and Restated Promissory Note, dated as of February 28, 2020, by MediaCo Holding Inc. in favor of SG Broadcasting LLC.

Exhibit 10.1 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY COMPARABLE STATE SECURITIES LAW. EXCEPT AS EXPRESSLY PROVIDED HEREIN, NEITHER THIS NOTE NOR ANY PORTION HEREOF OR INTEREST HEREIN MAY BE SOLD, ASSIGNED, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED OF UNLESS THE SAME IS REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAWS OR UNLESS AN EXEMPT

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): February 28, 2020 MediaCo Holding Inc. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 001-39029 (Commission file number) 84-24

Amendment No. 1 to Amended and Restated Term Loan Agreement, dated as of February 28, 2020, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.

Exhibit 10.2 AMENDMENT NO 1. AND WAIVER TO AMENDED AND RESTATED CREDIT AND SECURITY AGREEMENT AMENDMENT NO. 1 AND WAIVER TO AMENDED AND RESTATED TERM LOAN AGREEMENT, dated as of February 28, 2020 (this “Amendment No. 1”), is by and among MEDIACO HOLDING INC., an Indiana corporation (“MediaCo”), MEDIACO WQHT LICENSE LLC, an Indiana limited liability company (“MediaCo WQHT”) and MEDIACO WBLS LICENSE

Amendment No. 1 to Amended and Restated Term Loan Agreement, dated as of February 28, 2020, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.

Exhibit 10.2 AMENDMENT NO 1. AND WAIVER TO AMENDED AND RESTATED CREDIT AND SECURITY AGREEMENT AMENDMENT NO. 1 AND WAIVER TO AMENDED AND RESTATED TERM LOAN AGREEMENT, dated as of February 28, 2020 (this “Amendment No. 1”), is by and among MEDIACO HOLDING INC., an Indiana corporation (“MediaCo”), MEDIACO WQHT LICENSE LLC, an Indiana limited liability company (“MediaCo WQHT”) and MEDIACO WBLS LICENSE

Amended and Restated Promissory Note, dated as of February 28, 2020, by MediaCo Holding Inc. in favor of SG Broadcasting LLC.

Exhibit 10.1 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY COMPARABLE STATE SECURITIES LAW. EXCEPT AS EXPRESSLY PROVIDED HEREIN, NEITHER THIS NOTE NOR ANY PORTION HEREOF OR INTEREST HEREIN MAY BE SOLD, ASSIGNED, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED OF UNLESS THE SAME IS REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAWS OR UNLESS AN EXEMPT

Report of Independent Registered Public Accounting Firm

Exhibit 99.1 FMG Kentucky, LLC and FMG Valdosta, LLC Combined Carve-out Financial Statements For the Years Ended December 31, 2018 and 2017 FMG Kentucky, LLC and FMG Valdosta, LLC Combined Carve-out Financial Statements For the Years Ended December 31, 2018 and 2017 Page(s) Report of Independent Registered Public Accounting Firm 3 Combined Carve-out Financial Statements Combined Carve-out Balance

See accompanying notes to the condensed combined carve-out financial statements (unaudited).

Exhibit 99.2 FMG Kentucky, LLC and FMG Valdosta, LLC Condensed Combined Carve-out Financial Statements For the Nine Months Ended September 30, 2019 and 2018 (Unaudited) 1 FMG Kentucky, LLC and FMG Valdosta, LLC Condensed Combined Carve-out Financial Statements For the Nine Months Ended September 30, 2019 and 2018 (Unaudited) Page(s) Condensed Combined Carve-out Financial Statements Condensed Combi

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL STATEMENTS

Exhibit 99.3 UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL STATEMENTS Our unaudited pro forma condensed combined financial statements consist of an unaudited pro forma condensed combined balance sheet as of September 30, 2019, and unaudited pro forma condensed combined statement of operations for the nine months ended September 30, 2019, and the year ended February 28, 2019. On October 25, 2019

Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A (Amendment No. 1) CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): December 13, 2019 MediaCo Holding Inc. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 001-39029 (Commissio

MDIA / Mediaco Holding Inc. Class A / Francis Capital Management, Llc Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* MediaCo Holding, Inc. (Name of Issuer) Common Stock, par value $0.01 (Title of Class of Securities) 58450D104 (CUSIP Number) January 21, 2020 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to designate the rule pursuant

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numb

MDIA / Mediaco Holding Inc. Class A / Standard General L.P. Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. )* Mediaco Holding Inc. (Name of Issuer) Class A Common Stock (Title of Class of Securities) 58450D104 (CUSIP Number) Joseph Mause Standard General L.P. 767 Fifth Avenue, 12th Floor New York, NY 10153 Tel. No.: 212-257-4701 (Name, Address and Telephone Numbe

JOINT FILING AGREEMENT

Exhibit 99.1 JOINT FILING AGREEMENT This Joint Filing Agreement, dated as of January 28, 2020, is by and among Standard General L.P. and Soohyung Kim (collectively, the "Filers"). Each of the Filers may be required to file with the United States Securities and Exchange Commission a statement on Schedule 13G and/or 13D with respect to shares of Class A Common Stock, $0.01 par value per share, of Me

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (date of earliest event reported): January 21, 2020 MediaCo Holding Inc. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 001-39029 (Commission file number) 84-242

MediaCo Holding Inc. Investor Presentation January 2020

MediaCo Holding Inc. Investor Presentation January 2020 Safe Harbor / Forward-Looking Statements Certain statements included in this presentation which are not statements of historical fact, including but not limited to the preliminary full year pro forma financial information for 2019 and the budgeted financial information for 2020, as well as those identified with the words “expect,” “should,” “

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 MEDIACO HOLDING INC. (Exact na

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2019 MEDIACO HOLDING INC. (Exact name of registrant as specified in its charter) INDIANA (State of incorporation or organization) 001-39029 (Commission file number) 84-2427771 (I.R.S. E

Amended and Restated Articles of Incorporation of MediaCo Holding Inc.

Exhibit 3.1 AMENDED AND RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. These Amended and Restated Articles of Incorporation (the “Articles”) of MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), which was duly incorporated as of June 27, 2019, hereby amend, restate and replace the previously existing Articles of Incorp

Amended and Restated Articles of Incorporation of MediaCo Holding Inc.

Exhibit 3.1 AMENDED AND RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. These Amended and Restated Articles of Incorporation (the “Articles”) of MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), which was duly incorporated as of June 27, 2019, hereby amend, restate and replace the previously existing Articles of Incorp

Amended and Restated Articles of Incorporation of MediaCo Holding Inc.

Exhibit 3.1 AMENDED AND RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. These Amended and Restated Articles of Incorporation (the “Articles”) of MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), which was duly incorporated as of June 27, 2019, hereby amend, restate and replace the previously existing Articles of Incorp

Articles of Amendment to Amended and Restated Articles of Incorporation of MediaCo Holding Inc., as adopted December 13, 2019.

EX-3.1 2 tm1926389d1ex3-1.htm EXHIBIT 3.1 Exhibit 3.1 ARTICLES OF AMENDMENT TO AMENDED & RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. December 13, 2019 MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), does hereby certify that, pursuant to authority conferred upon the Board of Directors by Article VIII of the Amende

Assignment and Assumption of Purchase Agreement, dated as of December 13, 2019, by and between Billboards LLC and MediaCo Holding Inc.*

EX-10.1 3 tm1926389d1ex10-1.htm EXHIBIT 10.1 Exhibit 10.1 Assignment and Assumption of Purchase Agreement This Assignment and Assumption of Purchase Agreement (this “Assignment”), dated as of December 13, 2019 (the “Effective Date”), is by and between Billboards LLC, a Delaware limited liability company (“Assignor”), and MediaCo Holding Inc., an Indiana corporation (“Assignee”). WHEREAS, Assignor,

Amended and Restated Term Loan Agreement, dated as of December 13, 2019, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.*

Exhibit 10.5 EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT This EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT, dated as of December 13, 2019 (this ?Agreement?), is executed by FMG Valdosta, LLC, a Delaware limited liability company (?Assignee?), and Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Assignor?). Capitalized terms used but not defined herein have the respec

Amended and Restated Term Loan Agreement, dated as of December 13, 2019, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.*

Exhibit 10.5 EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT This EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT, dated as of December 13, 2019 (this ?Agreement?), is executed by FMG Valdosta, LLC, a Delaware limited liability company (?Assignee?), and Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Assignor?). Capitalized terms used but not defined herein have the respec

Transitional Services Agreement, dated as of December 13, 2019, by and between, FMG Kentucky, LLC, FMG Valdosta, LLC, and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.3 TRANSITIONAL SERVICES AGREEMENT THIS TRANSITIONAL SERVICES AGREEMENT (this ?Agreement?) is made and entered into as of December 13, 2019 (the ?Effective Date?) by and between (i) FMG Kentucky, LLC and FMG Valdosta, LLC, each a Delaware limited liability company (collectively, ?Recipient?), and (ii) Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Provider

Transitional Services Agreement, dated as of December 13, 2019, by and between, FMG Kentucky, LLC, FMG Valdosta, LLC, and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.3 TRANSITIONAL SERVICES AGREEMENT THIS TRANSITIONAL SERVICES AGREEMENT (this ?Agreement?) is made and entered into as of December 13, 2019 (the ?Effective Date?) by and between (i) FMG Kentucky, LLC and FMG Valdosta, LLC, each a Delaware limited liability company (collectively, ?Recipient?), and (ii) Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Provider

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Completion of Acquisition or Disposition of Assets, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): December 13, 2019 MediaCo Holding Inc. (Exact name of registrant as specified in its charter) Indiana (State or other jurisdiction of incorporation) 001-39029 (Commission File Number)

Equity Purchase Agreement, dated as of October 16, 2019, by and among Billboards LLC, FMG Kentucky, LLC, FMG Valdosta, LLC, and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.2 EQUITY PURCHASE AGREEMENT BY AND AMONG BILLBOARDS LLC, FAIRWAY OUTDOOR ADVERTISING GROUP, LLC, FMG KENTUCKY, LLC AND FMG VALDOSTA, LLC DATED AS OF OCTOBER 16, 2019 TABLE OF CONTENTS Page ARTICLE I PURCHASE AND SALE OF ACQUIRED SECURITIES 1 1.1 Purchase and Sale of Acquired Securities 1 1.2 Closing Payments 2 1.3 Adjustment of the Purchase Price 2 1.4 Escrow Amount 5 ARTICLE II CLOSING

Amended and Restated Term Loan Agreement, dated as of December 13, 2019, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.*

Exhibit 10.5 EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT This EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT, dated as of December 13, 2019 (this ?Agreement?), is executed by FMG Valdosta, LLC, a Delaware limited liability company (?Assignee?), and Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Assignor?). Capitalized terms used but not defined herein have the respec

Transitional Services Agreement, dated as of December 13, 2019, by and between, FMG Kentucky, LLC, FMG Valdosta, LLC, and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.3 TRANSITIONAL SERVICES AGREEMENT THIS TRANSITIONAL SERVICES AGREEMENT (this ?Agreement?) is made and entered into as of December 13, 2019 (the ?Effective Date?) by and between (i) FMG Kentucky, LLC and FMG Valdosta, LLC, each a Delaware limited liability company (collectively, ?Recipient?), and (ii) Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Provider

Assignment and Assumption of Purchase Agreement, dated as of December 13, 2019, by and between Billboards LLC and MediaCo Holding Inc.*

EX-10.1 3 tm1926389d1ex10-1.htm EXHIBIT 10.1 Exhibit 10.1 Assignment and Assumption of Purchase Agreement This Assignment and Assumption of Purchase Agreement (this “Assignment”), dated as of December 13, 2019 (the “Effective Date”), is by and between Billboards LLC, a Delaware limited liability company (“Assignor”), and MediaCo Holding Inc., an Indiana corporation (“Assignee”). WHEREAS, Assignor,

Articles of Amendment to Amended and Restated Articles of Incorporation of MediaCo Holding Inc., as adopted December 13, 2019.

EX-3.1 2 tm1926389d1ex3-1.htm EXHIBIT 3.1 Exhibit 3.1 ARTICLES OF AMENDMENT TO AMENDED & RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. December 13, 2019 MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), does hereby certify that, pursuant to authority conferred upon the Board of Directors by Article VIII of the Amende

Articles of Amendment to Amended and Restated Articles of Incorporation of MediaCo Holding Inc., as adopted December 13, 2019.

EX-3.1 2 tm1926389d1ex3-1.htm EXHIBIT 3.1 Exhibit 3.1 ARTICLES OF AMENDMENT TO AMENDED & RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. December 13, 2019 MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), does hereby certify that, pursuant to authority conferred upon the Board of Directors by Article VIII of the Amende

Equity Purchase Agreement, dated as of October 16, 2019, by and among Billboards LLC, FMG Kentucky, LLC, FMG Valdosta, LLC, and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.2 EQUITY PURCHASE AGREEMENT BY AND AMONG BILLBOARDS LLC, FAIRWAY OUTDOOR ADVERTISING GROUP, LLC, FMG KENTUCKY, LLC AND FMG VALDOSTA, LLC DATED AS OF OCTOBER 16, 2019 TABLE OF CONTENTS Page ARTICLE I PURCHASE AND SALE OF ACQUIRED SECURITIES 1 1.1 Purchase and Sale of Acquired Securities 1 1.2 Closing Payments 2 1.3 Adjustment of the Purchase Price 2 1.4 Escrow Amount 5 ARTICLE II CLOSING

Amended and Restated Term Loan Agreement, dated as of December 13, 2019, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.*

EX-10.6 8 tm1926389d1ex10-6.htm EXHIBIT 10.6 Exhibit 10.6 **************************************** AMENDED AND RESTATED TERM LOAN AGREEMENT Dated as of December 13, 2019 by and among MEDIACO HOLDING INC. THE OTHER PERSONS PARTY HERETO THAT ARE DESIGNATED AS BORROWERS, THE FINANCIAL INSTITUTIONS PARTY HERETO, as Term Lenders, and GACP FINANCE CO., LLC, as Term Agent ********************************

Equity Purchase Agreement, dated as of October 16, 2019, by and among Billboards LLC, FMG Kentucky, LLC, FMG Valdosta, LLC, and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.2 EQUITY PURCHASE AGREEMENT BY AND AMONG BILLBOARDS LLC, FAIRWAY OUTDOOR ADVERTISING GROUP, LLC, FMG KENTUCKY, LLC AND FMG VALDOSTA, LLC DATED AS OF OCTOBER 16, 2019 TABLE OF CONTENTS Page ARTICLE I PURCHASE AND SALE OF ACQUIRED SECURITIES 1 1.1 Purchase and Sale of Acquired Securities 1 1.2 Closing Payments 2 1.3 Adjustment of the Purchase Price 2 1.4 Escrow Amount 5 ARTICLE II CLOSING

Amended and Restated Term Loan Agreement, dated as of December 13, 2019, by and among MediaCo Holding Inc., the other parties designated as borrowers thereto, the financial institutions from time to time party thereto, and GACP Finance Co., LLC, a Delaware limited liability company, as administrative agent and collateral agent.*

Exhibit 10.5 EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT This EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT, dated as of December 13, 2019 (this ?Agreement?), is executed by FMG Valdosta, LLC, a Delaware limited liability company (?Assignee?), and Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Assignor?). Capitalized terms used but not defined herein have the respec

Articles of Amendment to Amended and Restated Articles of Incorporation of MediaCo Holding Inc., as adopted December 13, 2019.

EX-3.1 2 tm1926389d1ex3-1.htm EXHIBIT 3.1 Exhibit 3.1 ARTICLES OF AMENDMENT TO AMENDED & RESTATED ARTICLES OF INCORPORATION OF MEDIACO HOLDING INC. December 13, 2019 MediaCo Holding Inc., a corporation organized and existing under the laws of the State of Indiana (the “Corporation”), does hereby certify that, pursuant to authority conferred upon the Board of Directors by Article VIII of the Amende

Employee Assignment and Assumption Agreement, by and between FMG Kentucky, LLC and FMG Valdosta, LLC and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.4 EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT This EMPLOYEE ASSIGNMENT AND ASSUMPTION AGREEMENT, dated as of December 13, 2019 (this ?Agreement?), is executed by FMG Kentucky, LLC, a Delaware limited liability company (?Assignee?), and Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Assignor?). Capitalized terms used but not defined herein have the respec

Transitional Services Agreement, dated as of December 13, 2019, by and between, FMG Kentucky, LLC, FMG Valdosta, LLC, and Fairway Outdoor Advertising Group, LLC.*

Exhibit 10.3 TRANSITIONAL SERVICES AGREEMENT THIS TRANSITIONAL SERVICES AGREEMENT (this ?Agreement?) is made and entered into as of December 13, 2019 (the ?Effective Date?) by and between (i) FMG Kentucky, LLC and FMG Valdosta, LLC, each a Delaware limited liability company (collectively, ?Recipient?), and (ii) Fairway Outdoor Advertising Group, LLC, a Delaware limited liability company (?Provider

Assignment and Assumption of Purchase Agreement, dated as of December 13, 2019, by and between Billboards LLC and MediaCo Holding Inc.*

EX-10.1 3 tm1926389d1ex10-1.htm EXHIBIT 10.1 Exhibit 10.1 Assignment and Assumption of Purchase Agreement This Assignment and Assumption of Purchase Agreement (this “Assignment”), dated as of December 13, 2019 (the “Effective Date”), is by and between Billboards LLC, a Delaware limited liability company (“Assignor”), and MediaCo Holding Inc., an Indiana corporation (“Assignee”). WHEREAS, Assignor,

Shared Services Agreement (WEPN), dated as of November 25, 2019, by and between Emmis Operating Company and MediaCo Holding Inc.#

EX-10.4 6 a2240178zex-104.htm EX-10.4 Exhibit 10.4 Information in this exhibit identified by [***] is confidential and has been excluded pursuant to Item 601(b)(10)(iv) of Regulation S-K because it is both (i) not material and (ii) would likely cause competitive harm to the registrant if publicly disclosed. SHARED SERVICES AGREEMENT (WEPN) This SHARED SERVICES AGREEMENT (the “Agreement”), effectiv

Local Programming and Marketing Agreement, dated as of November 25, 2019, by and between MediaCo Holding Inc. and WBLS-WLIB LLC.

EX-10.6 8 a2240178zex-106.htm EX-10.6 Exhibit 10.6 LOCAL PROGRAMMING AND MARKETING AGREEMENT (WQHT HD2) THIS LOCAL PROGRAMMING AND MARKETING AGREEMENT (this “Agreement”) is made as of November 25, 2019 by and between MediaCo Holding Inc., an Indiana corporation (the “Licensee”), and WBLS-WLIB LLC, an Indiana limited liability company (“Programmer”). Recitals A. Licensee owns and operates the follo

Promissory Note, dated as of November 25, 2019, by MediaCo Holding Inc. in favor of SG Broadcasting LLC.

Exhibit 10.9 THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY COMPARABLE STATE SECURITIES LAW. EXCEPT AS EXPRESSLY PROVIDED HEREIN, NEITHER THIS NOTE NOR ANY PORTION HEREOF OR INTEREST HEREIN MAY BE SOLD, ASSIGNED, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED OF UNLESS THE SAME IS REGISTERED UNDER SAID ACT AND APPLICABLE STATE SECURITIES LAWS OR UNLESS AN EXEMPT

Promissory Note, dated as of November 25, 2019, by MediaCo Holding Inc. in favor of Emmis Communications Corporation

Exhibit 10.8 THIS NOTE IS SUBJECT TO THE PROVISIONS OF A CONTRIBUTION AND DISTRIBUTION AGREEMENT, DATED THE DATE HEREOF, BY AND AMONG, MEDIACO HOLDING INC., THE HOLDER (AS DEFINED BELOW) AND THE OTHER PARTIES IDENTIFIED THEREIN. THIS NOTE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY COMPARABLE STATE SECURITIES LAW. EXCEPT AS EXPRESSLY PROVIDED HEREIN, NEITHER THIS N

Shared Services Agreement (WEPN), dated as of November 25, 2019, by and between Emmis Operating Company and MediaCo Holding Inc.#

EX-10.4 6 a2240178zex-104.htm EX-10.4 Exhibit 10.4 Information in this exhibit identified by [***] is confidential and has been excluded pursuant to Item 601(b)(10)(iv) of Regulation S-K because it is both (i) not material and (ii) would likely cause competitive harm to the registrant if publicly disclosed. SHARED SERVICES AGREEMENT (WEPN) This SHARED SERVICES AGREEMENT (the “Agreement”), effectiv

Contribution and Distribution Agreement, dated as of June 28, 2019, by and among Emmis Communications Corporation, MediaCo Holding Inc., and SG Broadcasting LLC.*

Exhibit 2.1 CONTRIBUTION AND DISTRIBUTION AGREEMENT by and among EMMIS COMMUNICATIONS CORPORATION, MEDIACO HOLDING INC. and SG BROADCASTING LLC DATED AS OF JUNE 28, 2019 TABLE OF CONTENTS ARTICLE I DEFINITIONS 2 Section 1.1 General 2 Section 1.2 Construction 13 Section 1.3 References to Time 14 ARTICLE II THE INITIAL CONTRIBUTION AND PURCHASER INVESTMENT 14 Section 2.1 Contribution and Transfer of