Item 1.01 Entry into a Material Definitive
Agreement.
Exchange Offer and PIK Note Offer to Amend
On May 26, 2023, FOXO
Technologies Inc. (the “Company,” “we,” “us” or “our”) consummated (i) its issuer
tender offer to all holders of the Company’s Assumed Warrants (as defined below) to receive 4.83 shares of the Company’s Class
A common stock, par value $0.0001 per share (the “Class A Common Stock”), in exchange for each Assumed Warrant tendered pursuant
to the terms and subject to the conditions set forth in the Company’s issuer tender offer statement on Schedule TO and the related
exhibits included therein originally filed with the U.S. Securities and Exchange Commission (the “SEC”) on April 27, 2023,
and amended by Amendment No. 1 on May 5, 2023 and Amendment No. 2 on May 30, 2023 (the “Exchange Offer”), and (ii) its issuer
tender offer to all holders of the Company’s 15% Senior Promissory Notes (the “PIK Notes”) that were issued to accredited
investors in a private placement pursuant to a Senior Promissory Note Purchase Agreement, dated September 20, 2022, between the Company
and each purchaser thereof (the “PIK Note Purchase Agreement”), to receive 1.25 shares of Class A Common Stock for every $1.00
of the Original Principal Amount (as defined in the PIK Notes) of such holder’s PIK Notes, in exchange for the consent by such holder
of PIK Notes to amendments to the PIK Note Purchase Agreement, pursuant to the terms and subject to the conditions set forth in the Company’s
issuer tender offer statement on Schedule TO and the related exhibits included therein originally filed with the SEC on April 27, 2023,
and amended by Amendment No. 1 on May 5, 2023 and Amendment No. 2 on May 30, 2023 (the “PIK Note Offer to Amend”). The Exchange
Offer and the PIK Note Offer to Amend each expired at 11:59 p.m., Eastern Time, on May 26, 2023 (the “Exchange Offer Expiration
Date” or the “PIK Note Offer to Amend Expiration Date,” as applicable).
Warrants eligible to be tendered
pursuant to the Exchange Offer included all 1,905,853 of the Company’s outstanding warrants to purchase one share of Class A Common
Stock per warrant at an exercise price per share of $6.21, subject to adjustment, that were originally issued to accredited investors
by FOXO Technologies Operating Company (“Legacy FOXO”) in a private placement of convertible debentures (as amended, the “Original
Debentures”) and warrants to purchase shares of Class A common stock of Legacy FOXO (as amended, the “Original Warrants”
and together with the Original Debentures, the “Original Securities”) and assumed by us pursuant to the business combination
of our predecessor, Delwinds Insurance Acquisition Corp. and Legacy FOXO consummated on September 15, 2022 (the “Business Combination”)
(the “Assumed Warrants” and together with the Original Securities, the “Securities”).
As part of the Exchange Offer,
the Company also solicited consents from holders of the Assumed Warrants to amend and restate in its entirety the Securities Purchase
Agreement, dated as of January 25, 2021 (as amended, the “Original Securities Purchase Agreement”), by and between Legacy
FOXO (and assumed by the Company in connection with the Business Combination) and each purchaser of Original Securities identified on
the signature pages thereto, which governs all of the Securities, pursuant to the terms of an Amended and Restated Securities Purchase
Agreement (the “Amendment and Restatement”), to provide that the issuance of shares of Class A Common Stock and certain issuances
of Common Stock Equivalents (as defined in the Original Securities Purchase Agreement) in connection with the Exchange Offer, the PIK
Note Amendment (as defined below), the 2022 Debenture Release (as defined below), a Private Placement (as defined below) and a Public
Financing (as defined below), and as Private Placement Additional Consideration (as defined below), as well as any previous issuance of
Class A Common Stock or Common Stock Equivalents (as defined in the Original Securities Purchase Agreement), do not trigger, and cannot
be deemed to have triggered, any anti-dilution adjustments in the Securities.
In order to tender Assumed
Warrants in the Exchange Offer, holders were required to consent to the Amendment and Restatement and a general release (the “Exchange
Offer General Release Agreement”). Holders who tendered their Assumed Warrants in the Exchange Offer were deemed to have authorized,
approved, consented to and executed the Amendment and Restatement and the Exchange Offer General Release Agreement.
The
consummation of the Exchange Offer was conditioned upon, among other things, stockholder approval of the issuance of Class A Common Stock
as required by NYSE American Company Guide Section 713, and that Assumed Warrants, the holders of which purchased at least 50.01%
in interest of the Original Debentures based on the initial Subscription Amounts (as defined in the Original
Securities Purchase Agreement) thereof (which is the minimum amount required to amend the
Original Securities Purchase Agreement), are tendered in the Exchange Offer.
Pursuant to the Exchange Offer, an aggregate of 1,647,201 Assumed Warrants
were tendered, the holders of which purchased at least 50.01% in interest of the Original Debentures based on the initial Subscription
Amounts thereof. As disclosed in Item 5.07 of this Current Report on Form 8-K, the Company’s
stockholders approved the issuance of Class A Common Stock in connection with the Exchange Offer at the Company’s 2023 Annual
Meeting of Stockholders held on May 26, 2023 (the “Annual Meeting”). We issued an aggregate of 7,955,948 shares of Class A
Common Stock to the holders of Assumed Warrants who participated in the Exchange Offer, on the terms and subject to the conditions of
the Exchange Offer. The Amendment and Restatement and the Exchange Offer General Release Agreement are each effective as the Exchange
Offer Expiration Date.
Pursuant to the PIK Note Offer
to Amend, the Company solicited approval from holders of PIK Notes to amend the PIK Note Purchase Agreement to permit the following issuances
by the Company of Class A Common Stock and Common Stock Equivalents (as defined in the PIK Note Purchase Agreement), without prepaying
the PIK Notes: (i) the issuance of shares of Class A Common Stock in connection with the PIK Offer Note Offer to Amend, (ii) the issuance
of shares of Class A Common Stock in connection with the Exchange Offer, (iii) the issuance of shares of Class A Common Stock or Common
Stock Equivalents (as defined in the PIK Note Purchase Agreement) in connection with the 2022 Debenture Release (as defined below), (iv)
the issuance of shares of Class A Common Stock or Common Stock Equivalents (as defined in the PIK Note Purchase Agreement) in (a) a private
placement of the Company’s equity, equity-linked or debt securities resulting in gross proceeds to the Company no greater than $5
million (a “Private Placement”) and/or (b) a registered offering of the Company’s equity, equity-linked or debt securities
resulting in gross proceeds to the Company no greater than $20 million (a “Public Financing”); provided that (A) the proceeds
of a Private Placement resulting in gross proceeds to the Company of at least $2 million are used by the Company to prepay not less than
25% of the Outstanding Principal Balance (as defined in the PIK Notes) as of the date of prepayment on a pro rata basis upon the closing
of such Private Placement, and (B) the proceeds of a Public Financing resulting in gross proceeds to the Company of at least $10 million
are used by the Company to prepay all of the Outstanding Principal Balance as of the date of prepayment upon the closing of such Public
Financing, and (v) the issuance of shares of Class A Common Stock or Common Stock Equivalents (as defined in the PIK Note Purchase
Agreement) as Private Placement Additional Consideration (as defined below) (collectively, the “PIK Note Amendment”).
In order to participate in
the PIK Note Offer to Amend, in addition to consenting to the PIK Note Amendment, holders of PIK Notes were required to consent to a general
release (the “PIK Note Offer to Amend General Release Agreement”). Holders who participated in the PIK Note Offer to
Amend were deemed to have authorized, approved, consented to and executed the PIK Note Amendment and the PIK Note Offer to Amend General
Release Agreement.
The
consummation of the PIK Note Offer to Amend was conditioned upon, among other things, stockholder
approval of the issuance of Class A Common Stock as required by NYSE American Company Guide Section 713, and the receipt of consent of
holders that purchased at least 50.01% in interest of the aggregate principal balance of the PIK Notes (which is the minimum amount required
to amend the PIK Note Purchase Agreement) (the “Majority Consent”).
Pursuant to the PIK Note Offer
to Amend, all PIK Note holders participated in the PIK Note Offer to Amend, and therefore Majority Consent was obtained. As
disclosed in Item 5.07 of this Current Report on Form 8-K, the Company’s stockholders approved the issuance of Class A Common
Stock in connection with the PIK Note Offer to Amend at the Annual Meeting. We issued
an aggregate of 4,321,875 shares of Class A Common Stock on a pro rata basis to the PIK Note holders who participated in the PIK Note
Offer to Amend, on the terms and subject to the conditions of the PIK Note Offer to Amend. The PIK Note Amendment and the PIK Note Offer
to Amend General Release Agreement are each effective as of the PIK Note Offer to Amend Expiration Date.
Because the PIK Note Amendment
was approved, if the Company conducts a Private Placement, each investor who participates in the
Private Placement who was a holder of Assumed Warrants or PIK Notes as of the commencement of the Exchange Offer or the PIK Note Offer
to Amend, as applicable, and each former holder of 2022 Debentures (as defined below), may receive additional shares of Class A Common
Stock or Common Stock Equivalents (as defined in the Original Securities Purchase Agreement or the PIK Note Purchase Agreement, as applicable)
in addition to the other terms of such Private Placement offered to all investors, whether or not such holder participated in the Exchange
Offer or the PIK Note Offer to Amend, as applicable (the “Private Placement Additional Consideration”).
The Company’s Board
of Directors (the “Board”) has also authorized the Company to offer Class A Common Stock or Common Stock Equivalents (as defined
in the Original Securities Purchase Agreement or the PIK Note Purchase Agreement, as applicable) in exchange for a general release by
the former holders of 10% Original Issue Discount Convertible Debentures issued in 2022 by Legacy FOXO (the “2022 Debentures”),
which 2022 Debentures were automatically converted into Class A common stock of Legacy FOXO and exchanged by the Company for Class A
Common Stock in connection with the Business Combination, subject to stockholder approval and other conditions to be determined by the
Company, at a future date to be determined by the Company (the “2022 Debenture Release”). As currently contemplated, and subject
to change, each former holder of the 2022 Debentures that executes such general release would receive approximately 0.67 shares of Class
A Common Stock for every $1.00 of original principal amount of its 2022 Debentures, and if all former holders of 2022 Debentures execute
such general release, up to 18,760,000 shares of Class A Common Stock would be issued by the Company to such former holders of the 2022
Debentures.
The foregoing description
of the Amendment and Restatement, the Exchange Offer General Release Agreement, the PIK Note Amendment and the PIK Note Offer to Amend
General Release Agreement does not purport to be complete and is qualified in its entirety by reference to the full text of the Amendment
and Restatement, the Exchange Offer General Release Agreement, the PIK Note Amendment and the PIK Note Offer to Amend General Release
Agreement, copies of which are filed as Exhibits 10.1, 10.2, 10.3 and 10.4, respectively, to this
Current Report on Form 8-K, and are incorporated herein by reference.