CHESSWOOD GROUP LIMITED TO ACQUIRE WAYPOINT INVESTMENT PARTNERS INC.

TORONTO, March 15, 2022 – Chesswood Group Limited (TSX: CHW) (“Chesswood”), a publicly traded North American specialty finance company, and Waypoint Investment Partners Inc. (“Waypoint”), a Toronto based investment fund and private client investment manager, are pleased to announce that Chesswood and its wholly-owned subsidiary, Chesswood Capital Management Inc. (“CCM”), have entered into a definitive agreement to acquire Waypoint.

“The acquisition of Waypoint is an important step in building an integrated asset management platform within the Chesswood Group of Companies,” said Ryan Marr, CEO Chesswood Group.
The acquisition of Waypoint provides CCM with an integrated platform to structure and distribute private credit solutions to Canadian investors alongside Waypoint’s growing suite of alternative investment funds.

“The team at CCM is excited to work with the management of Waypoint to offer Canadian investors access to Chesswood’s diversified loan portfolio in formats designed to offer attractive risk-adjusted returns,” said Jeff Fields, CEO of CCM. “The acquisition of Waypoint will provide Chesswood with additional capabilities as we expand our institutional forward flow partnerships and private credit investment offerings,” added Fields.

“The Waypoint team is excited to be joining CCM and we look forward to providing Canadian investors with best-in-class private credit solutions in addition to our existing alternative equity offerings,” said Max Torokvei, CEO of Waypoint.

The consideration for the acquisition will be the payment of approximately $1.6 million and the issue of 150,983 Chesswood common shares. The acquisition of Waypoint is expected to close in Q2 2022 following receipt of regulatory approval (including the approval of the Ontario Securities Commission for Chesswood to acquire ownership of a registrant and the approval of the Toronto Stock Exchange for the issue and listing of the Chesswood common shares to be issued).

Ryan Marr, a director and the President and CEO of Chesswood, has a small minority shareholder interest (less than 8%) in Waypoint. As a result, the proposed acquisition of Mr. Marr’s interest as part of the proposed acquisition of Waypoint is a related party transaction for purposes of Multilateral Instrument 61-101 Protection of Minority Securityholders in Special Transactions. The proposed acquisition is exempt from the formal valuation and minority shareholder approval requirements of such Multilateral Instrument because the value of the transaction and transaction consideration in respect of Mr. Marr are below 25% of Chesswood’s market capitalization (in fact, below 0.2% of Chesswood’s market capitalization). The proposed acquisition was unanimously recommended by a special committee of independent directors and unanimously approved by each of Chesswood’s directors (other than Mr. Marr, who did not take part in the deliberations by Chesswood’s board of directors).

ABOUT WAYPOINT INVESTMENT PARTNERS INC.
Waypoint Investment Partners Inc. is a Toronto-based investment manager that services high net worth individuals, family offices, investment advisors, foundations and institutional clients. With a team of 12 experienced industry professionals, Waypoint delivers proprietary products and services. Waypoint is a member of the Portfolio Management Association of Canada and is registered as an Investment Fund Manager, Portfolio Manager and Exempt Market Dealer in several Canadian provinces. To learn more, visit www.waypointinvestmentpartners.com.

ABOUT CHESSWOOD GROUP LIMITED
Through three wholly owned subsidiaries in the United States and five subsidiaries in Canada, two of which are wholly owned, Chesswood Group Limited is a North American specialty finance company publicly traded on the Toronto Stock Exchange. Colorado-based Pawnee Leasing Corporation, founded in 1982, finances a highly diversified portfolio of commercial equipment leases and loans through relationships with over 600 brokers in the United States. Tandem Finance Inc. provides financing in the U.S. through the equipment vendor channel. In Canada, Blue Chip Leasing Corporation has been originating and servicing commercial equipment leases and loans since 1996, and today operates through a nationwide network of more than 50 brokers. Vault Credit Corporation specializes in equipment leases and commercial loans across Canada, allowing for customizable financing solutions while catering to a wide spectrum of credit tiers, equipment types and sectors by offering industry-leading service levels, experienced underwriters, and account administrators. Vault Home was acquired in September 2021 and focuses on providing home improvement and other consumer financing solutions in Canada. Rifco Inc. is focused on being the best alternative auto finance company, with the mission to help Canadians own automobiles. Rifco seeks to create sustainable long-term competitive advantages through personalized partnerships with dealers, innovative products, the use of industry-leading data and analytics, and leading collections practices. Chesswood Capital Management will provide private credit alternatives to investors seeking exposure to loan receivables, including those originated by Chesswood subsidiaries.

Based in Toronto, Canada, Chesswood Group Limited’s shares trade on the TSX under the symbol CHW.

To learn more about Chesswood Group Limited, visit www.ChesswoodGroup.com.

The websites of Chesswood Group Limited’s operating businesses are:
www.PawneeLeasing.com www.BlueChipLeasing.com
www.TandemFinance.com www.VaultCredit.com www.VaultPay.com www.Rifco.net

Contact
Investor Relations: Phone: 416-386-3099 Email: investorrelations@chesswoodgroup.com
Media Inquiries: Ryan Marr, Chief Executive Officer, 416-386-3099, rmarr@chesswoodgroup.com
NO STOCK EXCHANGE, SECURITIES COMMISSION OR OTHER REGULATORY AUTHORITY HAS APPROVED OR DISAPPROVED THE INFORMATION CONTAINED HEREIN.