The Digital Skeptic: The Web as Founded by George Washington

NEW YORK ( TheStreet) -- Let's all bow down and thank our lucky stars we had George Washington and the founding fathers first -- and Tim Berners-Lee and the founding fathers of the Internet second.

Because if our digital-age leaders tried their hand at spinning up these United States, as Washington did, we'd almost certainly be spending this Fourth of July still coughing up tax dollars to Queen Elizabeth.

Go ahead. Name a single 21st century Information Age leader who had anything close to the vision, gumption and guts of this country's 18th century executives.

George Washington, just as Google's ( GOOG) Larry Page or Amazon's ( AMZN) Jeff Bezos, started out as high-tech surveyor and land speculator. The man went on to be part of the team that created the algorithm of checks and balances that defined our national government. And if that's not enough, our first president gave Alexander Hamilton the means to invent our free-market economy.

Like our digital-age founding fathers, Washington was far from perfect. Ron Charnow won a Pulitzer Prize for rendering our first president's battle to overcome a nasty temper and deep inner doubts in his great biography, Washington: A Life.

"People felt the inner force of his nature," Charnow wrote, "Even if they didn't exactly hear it or see it."

The sense of the pure power of George Washington, though, is best rendered in David McCullough's also Pulitzer Prize-winning classic, 1776. In spite of being beaten on the field over and over by superior British and German forces, as general of the Continental Army Washington elects to attack Trenton on Christmas Day. And like many a night fight before, it all goes wrong. Ice and wind lock two of his three units on the wrong side of the Delaware. Somehow, Washington and his tiny force make it across, but it takes way too much time and any chance of a safe retreat is lost.

"I knew well I could not reach Trenton before day was fairly broke, but as I was certain that there was no making a retreat, I determined to push on at all events," Washington would later write to John Hancock.

Facing what any sane man would consider near certain defeat and probable death, Washington marches on to surprise and prevail over King George's Hessian mercenaries and notch a critical early win in the American war for independence.

Now, our digital-age leaders are smart enough, I suppose. But do any of them have that kind of guts? I doubt it

Washington's letter to investors
What's deflating about Washington is that his place in history is muted mostly because he's viewed as an intellectual second-rower when compared with America's other top chief executives, such as Lincoln or Franklin Roosevelt. But if investors actually take the time to read Washington's words, they'll find some of the most literate, compassionate and downright useful thinking produced by any U.S. leader.

I am particularly stirred by Washington's Circular to the States, written June 8, 1783, just days after the English capitulation. "When we consider the magnitude of the prize we contended for, the doubtful nature of the contest and the favorable manner in which it has terminated," he wrote, "We shall find the greatest possible reason for gratitude and rejoicing."

This letter -- almost St. Paul-like -- goes on to dive deeply into the opportunities and challenges that lay ahead for a young and still vulnerable country.

"It appears to me there is an option still left to the United States of America, that it is in their choice, and depends upon their conduct, whether they will be respectable and prosperous, or contemptible and miserable as a Nation," he wrote.

Washington then breaks the task ahead into four simple steps -- to have a union of states under one federal head; a sacred regard for justice; the adoption of a proper peace establishment; and, finally:

Among the people of the United States, there must be a means to "induce them to forget their local prejudices and policies, to make those mutual concessions which are requisite to the general prosperity," Washington wrote. "And in some instances, to sacrifice their individual advantages to the interest of the Community."

The letter leads investors to an interesting set of ideas: What if a smart, capable and deeply good man such as Washington had the same hand in creating the Web that he had in creating our country? Chances are the complexities we now struggle with online of balancing our freedom with the needs of private property, security and profit would not be afterthoughts.

They'd be core values.

To these tired eyes, the Web Washington would have built would have been like the America he did build: a beacon of prosperity to the world. Not the lawless Sierra Leone we currently hustle around in. A land where the few enrich themselves and most go hungry.

A country can only be lucky every so often, I suppose.

This commentary comes from an independent investor or market observer as part of TheStreet guest contributor program. The views expressed are those of the author and do not necessarily represent the views of TheStreet or its management.

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