| Item 1.01. | Entry into a Material Definitive Agreement. |
Securities Purchase Agreement
On May 13, 2022, PLBY Group, Inc., a Delaware corporation
(the “Company”), entered into a securities purchase agreement (the “Purchase Agreement”) with Drawbridge DSO Securities
LLC (the “Purchaser”). Pursuant to the Purchase Agreement, the Company will issue and sell an aggregate of up to 50,000 shares
of a newly created series of the Company’s preferred stock, par value $0.0001 per share, designated as “Series A Preferred
Stock” (the “Series A Preferred Stock”) at a purchase price of $1,000.00 per share, resulting in total gross proceeds
to the Company of up to $50.0 million. The Company has agreed to pay to the Purchaser a fee of 2.0% of the aggregate purchase price of
the Series A Preferred Stock purchased by the Purchaser, and a fee of 1.0% of the aggregate purchase price of the 50,000 shares of
Series A Preferred Stock. The Company expects to use the proceeds from the sale of the Series A Preferred Stock to repurchase
shares of its Common Stock (as defined below) and for general corporate purposes.
The initial consummation of the sale of 25,000 shares of Series A
Preferred Stock (the “Closing”) was completed on May 16, 2022. Any future consummation of the sale of additional shares
of Series A Preferred Stock as contemplated by the Purchase Agreement is conditioned on customary closing conditions, including the
accuracy of representations and warranties and the performance of all obligations contained in the Purchase Agreement (in each case subject
to customary materiality qualifiers).
The Purchase Agreement further provides that, subject to customary
exceptions, including exceptions in the case of transfers to certain permitted transferees, the Purchaser will be subject to customary
transfer restrictions with respect to the Series A Preferred Stock.
The foregoing descriptions of the transactions contemplated by the
Purchase Agreement does not purport to be complete and is subject to, and qualified in its entirety by, the full text of the Purchase
Agreement attached hereto as Exhibit 10.1, which is incorporated herein by reference.
Certificate of Designation
The powers, designations, preferences and other rights of the shares
of Series A Preferred Stock are set forth in the Certificate of Designation establishing the Series A Preferred Stock (the “Certificate
of Designations”), filed by the Company with the Delaware Secretary of State on May 16, 2022, in connection with the Closing.
The Series A Preferred Stock will rank senior and in priority
of payment to the Company’s common stock, par value $0.0001 per share (the “Common Stock”), with respect to distributions
on liquidation, winding-up and dissolution. Each share of Series A Preferred Stock will have an initial liquidation preference of
$1,000 per share (the “Liquidation Preference”).
Holders of shares of Series A Preferred Stock will be entitled
to cumulative dividends, which will be payable quarterly in arrears in cash or, subject to certain limitations, in shares of Common Stock
or any combination thereof, or by increasing the Liquidation Preference for each outstanding share of Series A Preferred Stock to
the extent not so paid. Dividends will initially accrue on each share of Series A Preferred Stock at the rate of 8.0% per annum from
the date of issuance until the fifth anniversary of the date of issuance, and thereafter such rate will increase quarterly by 1.0%.
At any time, the Company will have the right, at its option, to redeem
the Series A Preferred Stock, in whole or in part. The Company will also be required to redeem the Series A Preferred Stock
in full on September 30, 2027, or upon certain changes of control of the Company, subject to the terms of the Certificate of Designation.
The redemption price will be equal to the initial Liquidation Preference
of each share of Series A Preferred Stock to be redeemed multiplied by (i) if any applicable redemption date occurs on or prior
to the first anniversary of the Closing, 120%, (ii) if any applicable redemption date occurs after the first anniversary of the closing,
but prior to or on the second anniversary of the closing, 125%, (iii) if any applicable redemption date occurs after the second anniversary
of the closing, but prior to or on the third anniversary of the closing, 130%, (iv) if any applicable redemption date occurs after
the third anniversary of the closing, but prior to or on the fourth anniversary of the closing, 145%, and (v) if any applicable redemption
date occurs after the fourth anniversary of the closing, 160%, plus, in each case, a pro rata portion of the increase in the value of
the shares of Common Stock repurchased with the proceeds of the offering of the Series A Preferred Stock as of the applicable redemption
date, as set forth in the Certificate of Designation.
The redemption price will be payable in cash or, subject to certain
limitations, in shares of Common Stock or any combination of cash and shares of Common Stock, at the Company’s election.
Holders of the Series A Preferred Stock will generally not be
entitled to vote on any matter required or permitted to be voted upon by the shareholders of the Company. However, certain matters will
require the approval of the holders of not less than the majority of the aggregate Liquidation Preference of the outstanding Series A
Preferred Stock, voting as a separate class, including (1) the incurrence or issuance by the Company of certain indebtedness or shares
of senior equity securities, (2) certain restricted payments by the Company, (3) certain consolidations, amalgamations or merger
transactions involving the Company, (4) certain amendments to the organizational documents of the Company, (5) the incurrence
of indebtedness or preferred equity securities by certain subsidiaries of the Company and (6) certain business activities of the
Company.
The foregoing descriptions of the Certificate of Designation does not
purport to be complete and is subject to, and qualified in its entirety by, the full text of the Certificate of Designation attached hereto
as Exhibit 3.1, which is incorporated herein by reference.
