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George Washington, Founding CEO

May 2024
7min read

Sharp business skills ensured the first president’s phenomenal success

America’s greatest leader was its first—George Washington. He ran two start-ups, the army and the presidency, and chaired the most important committee meeting in U.S. history, the Constitutional Convention. His agribusiness and real estate portfolio made him America’s richest man. He was as well known as any actress, rapper, or athlete. Men followed him into battle; women longed to dance with him; famous men, almost as great as he was, some of them smarter or better spoken, did what he told them to do. He was the Founding CEO.

Even at a time when entertainers and freaks commandeer so much of our attention, the most important men and women in society are its leaders, whether in politics, business, or war. In politics, the buck stops at their desks; in business, they are responsible for bringing in the bucks; in war, they plan the operations and command the troops. That is why it is always important to know how a great leader of the past navigated his life, and what a leader or aspiring leader of today can learn from him.

When George Washington died, one of his mourners called him “first in war.” He got his first taste of the military at age 21, when his in-laws got him a commission in the colonial militia. His superiors found him a bit of a pain in the neck; his junior officers adored him, calling him an “excellent commander,” a “sincere friend,” and an “affable” companion. He saw two debacles, in which hundreds of his comrades were killed, and one great victory in which not a shot was fired; he was assigned to defend an undefendable frontier. When he was 26, he resigned, went home, and got married.

When Washington was 43, he got a harder assignment. Congress named him commander in chief in June 1775; he had angled for the job by showing up to the sessions of Congress in his old uniform. The American Revolution had barely begun. The troops he was assigned to command were local militias that had been renamed the Continental Army; turning them into an actual army would be one of his many tasks. During his time on the job, he fought 10 battles in five states and oversaw operations from Canada to Georgia to Indiana (then the Wild West). Between battles, he solved a range of problems from smallpox to treason. Since there was not yet any such thing as a president, secretary of defense, or secretary of state—the government consisted only of Congress—his job as commander in chief embraced some of the functions of these jobs as well: negotiating with Indians and Frenchmen, buying shoes and food. Although Congress had picked him unanimously, and backed him throughout the war, there were times when individual members schemed to replace him and when Congress as a whole simply couldn’t help him; he had to deal with that too. In December 1783, after the last skirmish had been fought and the last negotiations concluded, Washington resigned in a simple ceremony. “The spectators all wept,” wrote one of them, “and there was hardly a member of Congress who did not drop tears.” Washington went home for Christmas—the first he had celebrated there in nine years.

His eulogist also called him “first in peace.” He left home in 1787 to attend a convention of delegates from across the country that had been called in Philadelphia to revise the form of government. He showed up when he was supposed to, though there were not enough fellow delegates for a quorum (“these delays,” he wrote, “. . . sour the temper of the punctual members”). On the first day of business, in late May, he was chosen to chair the meeting. The convention met every day, except Sundays and a 10-day break in late summer, for nearly four months. Washington attended every session. Fifty-four other delegates attended at various times, of whom perhaps 20 did most of the heavy arguing and heavy lifting. The result was that the United States got a brand-new constitution, including a chief executive (“The executive Power shall be vested in a President of the United States of America”—Article II, Section 1).

Washington got that job, too, in the spring of 1789. Many private organizations had presidents, including fire companies and cricket clubs, as Vice President John Adams remarked. But no country in the world then, and very few in history, had been ruled by such a figure; everything Washington did was, in a sense, being done for the first time. He had more free time in this job than he had enjoyed as commander in chief, and he was able to spend his summers at home. But while he was in the nation’s capital, he met regularly with his cabinet and greeted the public at weekly receptions. He also made a point of visiting every state, at a time when travel was not routine (his Air Force One was a carriage). He performed some tasks that the old national government had performed, such as waging war and negotiating peace; other tasks—suppressing a rebellion, collecting taxes, paying debts—were novelties in American history. “Few,” he wrote circumspectly, “can realize the difficult and delicate part which a man in my situation had to act.” Chateaubriand, the French poet and diplomat, was more effusive: What did Washington leave as his legacy in “the unknown forests” of America? “Tombs? No, a world!”

In March 1797, after serving two four-year terms, Washington went home for good. Home had never been far from his thoughts, for Washington was first in business, and his corporate headquarters was Mount Vernon, his Virginia plantation. Washington’s family was prosperous, if not wealthy; his father had owned 10,000 acres, most of it undeveloped, and a share in an iron mine, and had sent his two oldest sons to England to be educated. But he had died when George was 11; instead of going to England, the boy would have to go to work. The same in-laws who would later put him in uniform hired him to survey their property, which was as big as New Jersey. The money he saved from his surveying and from his militia service became his stake. When he was 29, his older half-brothers having died, he inherited Mount Vernon, the family’s main property, a 2,500-acre tract on the Potomac (marrying a rich widow helped him improve it). Over the next four decades, he added 60,000 more acres in New York, Pennsylvania, Maryland, West Virginia, Kentucky, and Ohio. Most of this real estate was held as an investment; he hoped to flip it at a profit to other investors or lease it to tenants. Mount Vernon, however, was a working farm that was more like a little country: in the 1790s over 300 people lived on it, more than worked for the State Department or served in Congress. Washington Inc., or WashCorp, was a complex enterprise that included farming, food processing, and speculation. Its CEO had to cope with overseas customers, changing markets, and deteriorating natural resources. Although Washington was often strapped for cash, by the end of his life he was able to leave legacies to 23 heirs and free the labor force, his slaves. He did better than many of his wealthy peers: his friend, Philadelphia merchant Robert Morris, died in debt, and one fellow planter and president, Thomas Jefferson, died bankrupt.

At the climax of his life, Washington had fame and respect, power and honor, wealth and a good conscience. His long career had its share of disappointments and outright smashups, from lost battles to lost friendships, and Washington tended to focus on these shadows more than the average person for, as Jefferson put it, he was “inclined to gloomy apprehensions” (one of the subjects which made him apprehensive was Thomas Jefferson). But Jefferson also said, in his final judgment of the man, that “his character was, in its mass, perfect, in nothing bad, in few points indifferent.” How did he get to be this way? How did he learn to do all the things he did? How did he become such a leader?

No one is a born leader. George Washington had a long learning curve that began in his teens and stretched well into middle age. He learned from problems: from situations that he mastered or that mastered him. They came in every shape and degree of difficulty. On one disastrous day during the Revolution, he watched helplessly as the enemy captured 2,800 of his troops, which made him weep “with the tenderness of a child.” On a potentially more disastrous day, he had to talk his own officers down from a mutiny. “On other occasions,” wrote one of the officers who watched him do it, “he has been supported by the exertions of an army . . . but in this he stood single and alone.” As a political leader, he had to sit through six-hour-long speeches and tiny points of order. “Mr. Madison,” wrote James Madison in his notes on the Constitutional Convention, “moved to insert between ‘after’ and ‘it’ in Sect. 7 Art. I the words ‘the day on which’. . . . A number of members [became] very impatient & call[ed] for the question.” As a farmer, Washington had to oversee men and beasts. “Such a pen as I saw yesterday,” he wrote testily to one of his employees, “would, if the cattle were kept in it one week, destroy the whole of them. They would be infinitely more comfortable . . . in the open fields.” It was the last letter he wrote in his life; how many hundreds—thousands—had preceded it? He had to learn things he didn’t know, do things he didn’t do well, and learn not to attempt things he couldn’t do at all. He had to face unpleasant surprises and conundrums that squatted, toadlike, in his path for years.

He learned from people: people he worked for and with, and people who worked for him, including family and in-laws, comrades and colleagues, neighbors and strangers. He learned from a German who couldn’t speak English, a whippersnapper from the West Indies, and the planter down the road. Unlike Benjamin Franklin the cosmopolite, he never went abroad, except for a youthful trip to Barbados accompanying a half-brother who hoped the climate would be good for his health, so he had almost no opportunity to learn from foreigners in their own culture. To compensate, he met many foreigners in America—tourists, diplomats, officers (both friendly and hostile) who came here to fight in two world wars; his best male friend was a Frenchman. Other people of foreign culture lived right here: he met his first Native Americans when he was 16 and kept meeting with them into his 60s. There was no person who was the sole model for Washington’s life, but he spent decades picking up what he needed from whomever he could.

And, despite the fact that his own formal education stopped before what we would call middle school, he read: rules of etiquette, books on farming, generalship, politics, and history. Although he never read a book on leadership, early in his life he read a book on how to be a good man, by the Roman philosopher Seneca. His better-educated friends read the Renaissance political scientist, Machiavelli, who had written a book on leadership— The Prince —that is the model for many leadership books today. He learned from Seneca but was very different from Machiavelli and his modern descendants. He wanted to know how he should behave and how other men had behaved in positions of power and times of stress.

Action and reflection helped Washington in the most difficult subject of all, learning from himself: what he had, what he lacked, what he might acquire. Everyone makes mistakes; mistakes happen. It requires effort such as Washington’s to turn them into useful experience.

From the book George Washington on Leadership by Richard Brookhiser ©2008. Reprinted by arrangement with Basic Books, a member of the Perseus Books Group. This excerpt may not be reprinted without permission from Perseus Books Group and American Heritage Publishing.

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