George Washington was among the most successful businessmen of his day. Raised in a single-parent home and bereft of formal education, he nevertheless parleyed a modest inheritance into what was by the time of his death one of the grandest estates in North America. The odds were against him. Washington came of age under an oppressive colonial system that discouraged entrepreneurship and fostered debt. His increasingly passionate belief in economic freedom motivated his efforts to break free of this system, both personally and as an American patriot. Guiding his country through eight years of debilitating war followed by a lengthy period of economic instability, Washington managed simultaneously to set the United States on the road to prosperity and ensure that Mount Vernon became a center of agricultural and technological innovation. Five principles that inspired his accomplishments may still serve to guide entrepreneurs in the twenty-first century: Decisiveness. As a young entrepreneur in the 1760s Washington recognized that the colonial tobacco economy, which had been in place for over a century but operated on credit, stifled innovation and reduced Americans to debt slavery. After careful research, he moved decisively to abandon tobacco and change over his estate to the cultivation of wheat. The gamble paid off, not only making Mount Vernon self-sufficient but transforming it into a regional center of production. Innovation. Technology fascinated Washington. He tinkered ceaselessly but never aimlessly. A firm believer in experimentation, he tested tools with a view to their capacity to save labor and boost productivity. Among other cutting-edge technologies, he installed at Mount Vernon an advanced gristmill that allowed him to produce high-quality “G. Washington” brand flour and even market it overseas. Communication. After the Revolutionary War ended in 1783, Washington recognized that Great Britain—then in the early stages of the Industrial Revolution—was on the cusp of becoming a global economic powerhouse. He not only read the works of visionaries like Adam Smith, but fostered personal relationships with pioneering British innovators such as Arthur Young. Washington became a hero of the British manufacturing community as he worked to disseminate knowledge and promote trade. Calculated Risk-Taking. Martha quickly cured her husband of his youthful affinity for gambling at cards and billiards, but his entrepreneurial mind remained attuned to the thrill of the dice. Shortly after his retirement Washington’s Scottish farm manager James Anderson approached him with the seemingly reckless proposal to build a whiskey distillery at Mount Vernon. Previously ignorant of the industry, Washington researched it carefully and decided to risk a significant investment. The distillery quickly became one of his most profitable enterprises. Attention to Detail. Washington kept astonishingly meticulous accounts. He also insisted on understanding personally how every operation on his estate worked from bottom to top. At any given moment, thanks to his demands for detailed reports and his frequent rides around Mount Vernon, he intimately understood every aspect of his diverse and far-flung enterprise. This attention to fundamentals was a bedrock of his success. Edward G. Lengel is the author of First Entrepreneur: How George Washington Built His—and the Nation’s—Prosperity (Da Capo Press).