Chesswood Group Limited is engaged in financial services businesses. The Company operates through two segments: Equipment Financing-U.S. and Equipment Financing-Canada. The Equipment Financing-U.S. segment is involved in small-ticket equipment leasing and lending to small businesses. The Equipment Financing-Canada segment provides commercial equipment financing to small businesses in Canada. Through its interests in subsidiaries, the Company is engaged in providing micro and small-ticket equipment financing to small businesses; providing working capital loans to small businesses in over 30 states of the United States; providing commercial equipment financing to small and medium businesses in Canada; holding a portfolio of legal finance receivables in the United States.