This Amendment No. 8 to Schedule 13D (the “Amendment”) relates to Class A Common Stock (“Class A Common Stock”) of Mediaco Holding Inc., an Indiana corporation (the “Issuer” or the “Company”). This Amendment is being filed to amend the
Schedule 13D that was originally filed on January 28, 2020, as amended on February 5, 2020, March 30, 2020, April 24, 2020, May 22, 2020, September 2, 2020, September 23, 2020 and May 21, 2021 (as amended, the “Schedule 13D”). Unless otherwise
indicated in this Amendment, all capitalized terms have the meanings indicated to them in the Schedule 13D.
This Amendment is being filed to amend Item 5 of the Schedule 13D.
Item 5. Interest in Securities of the Issuer
Items 5 is hereby supplemented as set forth below.
(a) and (b) See Items 7-13 of the cover pages and Item 2 above.
(c) The Reporting Persons did not effect any transactions in shares of the Issuer’s Class A Common Stock during the sixty day period prior to the filing of this Schedule 13D.
As previously reported, the Reporting Persons beneficially own 184,201 shares of the Company’s Class A Common Stock and 5,413,197 shares of the Company’s Class B Common Stock, which is convertible into Class A Common Stock on a one-for-one basis.
As previously disclosed, the Reporting Persons beneficially own 220,000 shares of Series A Convertible Preferred Stock of the Company (“Series A Preferred Stock”), each share of which is convertible into such number of shares of Class A Common
Stock as is determined by dividing: (i) the purchase price of the Series A Preferred Stock plus any accrued dividends by (ii) the average volume-weighted average prices of the Class A Common Stock for the last 30 days prior to the date of
determination (the “30-Day VWAP”), determined as of the fifth business day after the date on which notice of conversion is given. As of November 26, 2021, the shares of Series A Preferred beneficially owned by the Reporting Persons would have
been convertible into 3,313,126 shares of Class A Common Stock under the formula described above.
As previously disclosed, the Reporting Persons also hold two secured convertible promissory notes of the Company (the “Second Amended and Restated Promissory Note” and the “2021 Note”). All or a portion of the outstanding principal and any
accrued interest under each such note is convertible, at the option of the Reporting Persons, into shares of Class A common Stock at a conversion price equal to the 30-Day VWAP, determined as of the fifth business days after the date on which
the notice of conversion is given; provided, in the case of the 2021 Note, that the conversion price shall not be less than $0.50 per share. As of November 26, 2021, the amounts of principal and accrued interest under the Second Amended and
Restated Promissory Note and the 2021 Note were approximately $23.5 million and $4.2 million, respectively. As of such date, the Second Amended and Restated Promissory Note and the 2021 Note were convertible into 2,922,605 and 523,504 shares
of Class A Common Stock, respectively.
The percentages reported herein are based on a statement in the Company’s Quarterly Report for the quarter ended September 30, 2021, as filed with the Securities and Exchange Commission on November 12, 2021, that, as of November 8, 2021, there
were 3,085,909 shares of the Issuer’s Common Stock outstanding.
(d) Not applicable.
(e) Not applicable.