While it may seem counter-intuitive that Lin-Manuel Miranda chose to portray the life of one of America’s most patrician Founding Fathers via hip-hop, it shouldn’t.  This descendant of a Scottish laird had words.  Lots of words.

He wrote poetry as a young boy clerking for a merchant in his native Caribbean.  He wrote his first political tracts as a student at King’s College before the Revolution and the institution’s name-change to Columbia.  He wrote dispatches after dispatches as an aide-de-camp to General George Washington.  Most significantly, he helped write the United States Constitution and, most importantly for us marketers, the first great piece of content marketing in the new republic, the Federalist Papers.

While the Federalist Papers represent content marketing at its best, other Hamilton publications show content marketing at its worst.  These extremes serve as good guideposts for modern content marketers.

I can’t recommend reading this 832-page doorstop (seriously, Mr. Miranda deserves a Nobel Prize for turning Ron Chernow’s hot-and-heavy love letter to Hamilton into entertainment), but I can attest to his meticulousness in explaining how Hamilton’s words both built a nation and destroyed his career.

Hi, I’m Al Hamilton.  And these are just some of my many, many fine words!

First, the good: those Federalist Papers.

For those of you who don’t remember your early American history, please recall that while we Americans revere our peerless-yet-imperfect Constitution, it did not enjoy universal approbation at birth. The political figures who would coalesce into Jefferson’s Republican party harbored strong suspicions of a centralized government dating back to their disagreements with that other fellow named George (as in King, III).  On the other hand, the Federalists-to-be recognized the Articles of Confederation as an ineffective way to organize the 13 states that emerged from the Revolution.  Oh, and then there was that little matter of whether it was OK to own other human beings.

Hamilton had a grand vision of a truly United States with strong credit, good relations with its former enemy and an economy with vibrant industry and banking.  Together with future President James Madison and future Chief Justice John Jay, he wrote series of essays designed to persuade lawmakers and their supporters to ratify the Constitution.  Hamilton brought together some key elements to ensure success:

• Understanding the audience.  Although he could write for crowds, Hamilton didn’t write the Federalist Papers for them.  He wrote a sophisticated set of political arguments for lawyers and other educated men.  Hamilton used great works of economics, philosophy and political science–the stuff then-rare college graduates–to support his arguments.
• Smart use of guest content.  Hamilton wrote 51 of the 85 essays by himself and assigned another 26 to Madison and 5 to Jay.  He also wrote 3 with Madison.  Since the essays appeared without a byline, he didn’t do this to share credit.  Rather, he depended on Madison’s expertise in government and Jay’s expertise in foreign policy.
• Working his ass off.  Did we mention that Hamilton wrote 60% of the essays?  He also served as editor and publisher.  As a later statesman, Riley B. (BB) King said, “you gotta pay the cost to be the boss.“

Effective content marketers follow these rules today.

Unfortunately, Hamilton also made some of the worst mistakes a content marketer could make.  He published, under his own name, a rigorous criticism of his boss, President John Adams and a defense of an extramarital affair.

The latter pamphlet requires a little explanation.  While Treasury Secretary, Hamilton undertook two endeavors that raised eyebrows: he founded the central bank and ran around on his wife.  While seemingly exclusive, these two things became enmeshed in a series of coincidences worthy of a 1960s French sex farce.

Contemporary political opponents believed that Hamilton had used his position as Secretary to enrich himself via speculation on bonds, which he had not.  However, he had paid hush money to his paramour, Maria Reynolds, and her dirtbag husband James.  Political opponents learned of the hush money and assumed that it had something to do with his alleged speculation.  In his mind, Hamilton felt  he could wriggle out of the situation by copping to the lesser of two evils, zipper trouble.  Thus, he produced the Reynolds Pamphlet outing himself as nothing more than a common philanderer.

The Reynolds Pamphlet failed as content marketing for two key reasons:

• Too much information.  Yes, your audiences want to know what makes your brand different, but they don’t want to know that much.
• If dig yourself into a hole, remember to stop digging.  Granted, “not making things worse” sounds like a good rule for any kind of marketing, but it goes double for content marketing.  By its free-form nature, content marketing excels at explaining things, such as how a product works or why you need it.  However, even two centuries before mansplaining, the Reynolds Pamphlet shows how keeping your mouth shut might work better than trying to explain your position.

I doubt that any marketer will ever employ content for something as important as rallying support for the Constitution.  Yet even for the day-in, day-out needs of commerce, Hamilton’s wisdom still has a lot to offer.

Oh, one more thing to learn from Hamilton: know when to duck.