Additional Proxy Soliciting Materials (definitive) (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

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☐	Preliminary Proxy Statement

☐	Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

☐	Definitive Proxy Statement

☒	Definitive Additional Materials

☐	Soliciting Material Under § 240.14a-12

MEDIACO HOLDING INC

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than Registrant)

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*** Exercise Your Right to Vote *** Important Notice Regarding the Availability of Proxy Materials for the Shareholder Meeting to Be Held on May 14, 2020. Meeting Information MEDIACO HOLDING INC. Meeting Type: Annual Meeting For holders as of: March 9, 2020 Date: May 14, 2020* Time: 9:00 a.m., local time Location: Pillsbury Winthrop Shaw Pittman LLP 31 W. 52nd Street New York, NY 10019 You are receiving this communication because you hold shares in the company named above. This is not a ballot. You cannot use this notice to vote these shares. This communication presents only an overview of the more complete proxy materials that are available to you on the Internet. You may view the proxy materials online at www.proxyvote.com or easily request a paper copy (see reverse side). * Due to concerns relating to the evolving coronavirus (COVID-19) situation, we may decide to hold the meeting in a different location or solely by means of remote communication (i.e., a virtual-only meeting). We plan to announce any such updates on our website (www.MediaCoHolding.com) under the Investors heading, and we encourage you to check this page of our website prior to the meeting if you plan to attend. We encourage you to access and review all of the important information contained in the proxy materials before voting. MEDIACO HOLDING INC. 40 MONUMENT CIRCLE INDIANAPOLIS, IN 46204 D03548-P34173 See the reverse side of this notice to obtain proxy materials and voting instructions.

Before You Vote How to Access the Proxy Materials Proxy Materials Available to VIEW or RECEIVE: NOTICE AND PROXY STATEMENT FORM 10-K How to View Online: Have the information that is printed in the box marked by the arrow XXXX XXXX XXXX XXXX (located on the following page) and visit: www.proxyvote.com. How to Request and Receive a PAPER or E-MAIL Copy: If you want to receive a paper or e-mail copy of these documents, you must request one. There is NO charge for requesting a copy. Please choose one of the following methods to make your request: 1) BY INTERNET: www.proxyvote.com 2) BY TELEPHONE: 1-800-579-1639 3) BY E-MAIL*: sendmaterial@proxyvote.com * If requesting materials by e-mail, please send a blank e-mail with the information that is printed in the box marked by the arrow XXXX XXXX XXXX XXXX (located on the following page) in the subject line. Requests, instructions and other inquiries sent to this e-mail address will NOT be forwarded to your investment advisor. Please make the request as instructed above on or before April 30, 2020 to facilitate timely delivery. How To Vote D03549-P34173 Please Choose One of the Following Voting Methods Vote In Person: Many shareholder meetings have attendance requirements including, but not limited to, the possession of an attendance ticket issued by the entity holding the meeting. Please check the meeting materials for any special requirements for meeting attendance. At the meeting, you will need to request a ballot to vote these shares. Vote By Internet: To vote now by Internet, go to www.proxyvote.com. Have the information that is printed in the box marked by the arrow XXXX XXXX XXXX XXXX (located on the following page) available and follow the instructions. Vote By Mail: You can vote by mail by requesting a paper copy of the materials, which will include a proxy card.

PROPOSALS TO BE VOTED ON AT THE 2020 ANNUAL MEETING OF SHAREHOLDERS BY THE HOLDERS OF CLASS A COMMON STOCK The Board of Directors recommends you vote FOR the following: 1. Election of Director Nominee: 1a. J. Scott Enright The Board of Directors recommends voting FOR proposals 2, 3 and 4. 2. Approval of the 2020 Equity Compensation Plan as disclosed in the proxy statement. 3. Approval of the potential issuance of additional Class A Shares. 4. Ratification of the selection of Ernst & Young LLP as MediaCo Holding Inc.’s independent registered public accountants for the year ending December 31, 2020. NOTE: Transaction of any other business that may properly come before the meeting and any adjournments or postponements of the meeting. D03550-P34173

PROPOSALS TO BE VOTED ON AT THE 2020 ANNUAL MEETING OF SHAREHOLDERS BY THE HOLDERS OF CLASS B COMMON STOCK The Board of Directors recommends you vote FOR the following: 1. Election of Director Nominee: 1a. Mary Beth McAdaragh The Board of Directors recommends voting FOR proposals 2, 3 and 4. 2. Approval of the 2020 Equity Compensation Plan as disclosed in the proxy statement. 3. Approval of the potential issuance of additional Class A Shares. 4. Ratification of the selection of Ernst & Young LLP as MediaCo Holding Inc.’s independent registered public accountants for the year ending December 31, 2020. NOTE: Transaction of any other business that may properly come before the meeting and any adjournments or postponements of the meeting. D03551-P34173