FOXO Technologies Inc. entered into a non-binding letter of intent to acquire Delwinds Insurance Acquisition Corp. (NYSE:DWIN) from a group of shareholders for $300 million in a reverse merger transaction on August 6, 2021. FOXO Technologies Inc. executed a definitive agreement and plan of merger to acquire Delwinds Insurance Acquisition Corp. (NYSE:DWIN) from DIAC Sponsor LLC, management of Delwinds and others for $300 million in a reverse merger transaction on February 24, 2022. Consideration is inclusive of $100 million management earnout shares, subject to achievement of post-closure milestones. Approximately one-third of deal consideration is subject to management earn-out dependent on achievement of strategic milestones. 10 million of the merger consideration shares will be allocated to FOXO management pursuant to an earnout plan. As of July 6, 2022, the Management Contingent Plan was reduced from 10 million shares to 9.2 million shares. Transaction will be funded from Delwinds's cash in trust of $201 million. FOXO shareholders and management rolling 100% of their equity into the transaction. After the Closing, FOXO stockholders are expected to hold a majority of the combined company's share. Delwinds will merge with and into FOXO, with FOXO surviving the merger. As a result of the transaction, which values the combined company at an estimated enterprise value of $369 million, FOXO is expected to become publicly listed and plans to trade on the NYSE under ticker symbol ‘FOXO'. Upon the closing of the transaction, the combined company's board of directors is expected to include Illumina bioinformatics scientist Bret Barnes and health technology entrepreneur Murdoc Khaleghi, together with FOXO Founder and Chief Executive Officer Jon Sabes and Delwinds Chairman and Chief Executive Officer Andrew J. Poole. In addition, the members of FOXO's scientific advisory board, which include epigenetic scientists Peter Laired and Hui Shen from the Van Andel Institute, and data scientist and AI researcher Randall Olson from Absci are expected to continue as advisors to the Company.

The transaction is subject to the approval of the stockholders of Delwinds and FOXO, the approval by the Arkansas Department of Insurance, and other customary closing conditions. The transaction has been approved by the boards of directors of both Delwinds and FOXO. The shareholders meeting of Delwinds is scheduled on September 14, 2022. As of June 6, 2022, Delwinds stockholders approved the extending the date by which Delwinds must consummate the Initial Business Combination from June 15, 2022, to September 15, 2022. As of September 9, 2022, Delwinds Insurance Acquisition announced that its registration statement on Form S-4 was declared effective by the U.S. Securities and Exchange Commission on August 26, 2022. The definitive agreement includes no minimum cash closing requirement and is expected to close in Q2 2022. Assuming satisfaction (or waiver) of all closing conditions prior to such date, Delwinds expects to close the Business Combination on September 15, 2022. As of September 13, 2022, the transaction is expected to close on September 16, 2022. The Extension provides additional time in the event that it is needed to execute the closing. The transaction, combined with recent capital raising actions by FOXO, is expected to raise up to $224 million in total gross cash proceeds, including up to $201 million of cash held in Delwinds' trust account, assuming no redemptions by Delwinds public stockholders. Proceeds from the merger are expected to accelerate the development of FOXO's platform to offer saliva-based epigenetic biomarker underwriting technology and consumer engagement services to the global life insurance industry. Proceeds from the transaction will fund FOXO's intended launch of proprietary products and services including life insurance accompanied by the FOXO Longevity Report™ that drive its distribution and services platform to create “Life Insurance Designed to Keep you Alive.” The transaction has been approved by the shareholders of Delwinds Insurance on September 14, 2022.

Deutsche Bank Securities Inc. acted as financial advisor and Nimish Patel and Blake Baron of Mitchell Silberberg & Knupp LLP and Stinson Leonard Street LLP acted as legal advisors to FOXO Technologies Inc. RBC Capital Markets Inc. acted as financial advisor and Douglas S. Ellenoff and Stuart Neuhauser of Ellenoff Grossman & Schole LLP acted as legal advisor and due diligence provider to Delwinds Insurance Acquisition Corp. Covington & Burling LLP acted as legal advisor to Delwinds Insurance Acquisition Corp. Houlihan Lokey Capital, Inc. acted as financial advisor and fairness opinion provider to the Delwinds board of directors. Houlihan Lokey provided its opinion to the Special Committee. RBC Capital Markets Inc. and Cantor Fitzgerald acted as Capital Markets Advisors to Delwinds. Cohen & Company Capital Markets, a division of J.V.B. Financial Group, LLC acted as placement agents for the convertible debenture and redemption backstop to FOXO. Lamson, Dugan and Murray LLP acted as insurance regulatory counsel to Delwinds. Proskauer Rose LLP is serving as legal advisor to Cohen & Company Capital Markets. RBC Capital Markets Inc. will be paid a minimum financial advisory fee of $5 million and may be paid an additional financial advisory fee of up to $5 million, payable at Delwinds' sole discretion. Accordingly, if the Business Combination is not consummated by Delwinds, RBC will not receive the financial advisory fee. Joe Mills and John Ferguson of Saratoga Proxy Consulting, LLC acted as the information agents to Delwinds and have agreed to pay Saratoga a fee of $30,000 and also will reimburse Saratoga for reasonable out-of-pocket expenses and will indemnify Saratoga and its affiliates against certain claims, liabilities, losses, damages and expenses. Houlihan Lokey became entitled to an aggregate fee of $0.5 million for its services, of which $0.25 million was earned by Houlihan Lokey and payable upon the delivery of its opinion and $0.25 million was earned by Houlihan Lokey upon the delivery of its opinion and payable upon the first to occur of (x) the consummation of the transaction, (y) the consummation of another business combination involving Delwinds, and (z) the commencement of proceedings to dissolve Delwinds. Mark Zimkind of Continental Stock Transfer & Trust Company acted as transfer agent to Delwinds. Aaron Dixon of Alston & Bird LLP acted as legal advisor to Houlihan Lokey. Lamson, Dugan & Murray, LLP acted as due diligence provider to Delwinds. Cohen & Company Capital Markets, LLC acted as financial advisor to Delwinds Insurance Acquisition Corp.

FOXO Technologies Inc. completed the acquisition of Delwinds Insurance Acquisition Corp. (NYSE:DWIN) from a group of shareholders for approximately $340 million in a reverse merger transaction on September 15, 2022. The combined company will operate under the name “FOXO Technologies Inc.,” and will be led by Chief Executive Officer Jon Sabes, and will commence trading on the NYSE American exchange under the symbol “FOXO” on September 16, 2022. Upon the Closing, all outstanding shares of FOXO Class A Common Stock and FOXO Class B Common Stock were converted into 24,718,705 shares of Combine company, in addition to 10 million management earnout shares.