Many retirees today, struggle with transitions to successful business. Most retirees are never ready to take risks especially in business but still most of them think that retirement is a ticket to business. It is clear that even with the best of intentions; success in business is not a matter of chance, it must be made to happen. Traditional approaches to business startups must be revised to realize success. This book, therefore, examines the factors that interplay to influence the outcome of retirees’ businesses. These include financial stability, the present physical and mental strength, entrepreneurial skills and family base of the retirees. The context of business in Kenya will also dictate the ability of the retirees to embrace business ideas. The book also highlights the fact that the concept of retirement and planning in Kenya and most African countries is yet to be made more formal and gives very useful legislative insight for policy makers as well as contributing to scholarly knowledge. The analysis in this book will be useful in rejuvenating more energy towards this very exciting field that has enormous development potential.