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Management succession is a significant issue in many businesses. You put all your energy into your business, but how much time is spent on bench strength planning? Are you ready to hand the reins over and begin a life outside the office? Have you ensured everything you've worked to create will seamlessly help support your heirs? Macon F. Brock Jr. (president and CEO of Dollar Tree Stores), his brother-in-law Doug Perry, and "almost family member" Ray Compton founded the successful Dollar Tree business in 1986. For many years, they worked hard to develop leaders within the company as an ongoing source of talent. Through their combined efforts, the business grew from a small startup to the number one company in the discount and variety retail sector, generating nearly $2 billion in sales during 2001. As the entrepreneurs thought about retiring, many questions emerged: Who was going to take over leadership of the company? Would they need more than one person? Was there an heir apparent ready to step up? How would they structure the transition? This case presents the challenges of a transition from an entrepreneurial venture to a publicly traded business with a focus on succession management.