Hamilton and Hierarchies

In celebration of my move to King’s College (Loyalists like myself still call it King’s, while traitors to the Crown call it Columbia), I’ve just finished Ron Chernow’s behemoth biography on Alexander Hamilton, a thoroughly amazing if not demanding experience.

I’m an avid reader of biographies, from Steve Jobs to Elon Musk to Oppenheimer to Howard Hughes, and this is one of the most well-researched, comprehensive, and gripping narratives I’ve read to date. Chernow is able to weave an expansive array of personal and political histories across the Revolution, from Hamilton to Washington to Jefferson to Adams to Burr.

My only gripe with the book is that the rights were sold for a play that tells the story from Burr’s perspective (Burr, in my opinion, being one of the least interesting characters of the Hamilton saga). Albeit a very good play, Hamilton’s story deserved a Ridley Scott-esque historical epic to give us the definitive film on the American Revolution. There are so many amusing Hamilton anecdotes that paint a very charming, folk-hero picture of the man that I would’ve loved to see on-screen: a young Hamilton dragging artillery from The Battery as the British pound southern Manhattan with cannons, or waking (and thus saving) his Tory headmaster at King’s as a patriotic mob descends upon the campus in the middle of the night; the veteran politician Hamilton, while quashing the Whiskey Rebellion, catching and scolding a sleeping sentry, wrathfully relieving the guard of his post and taking his place, marching around camp all night with a musket on his shoulder.

But the main reason of this post isn’t to sing Chernow’s or Hamilton’s praises, but moreso to examine the principles behind the accumulation of power and influence that Hamilton garnered despite his grim origins and relatively short lifespan of 49 years. I wouldn’t hesitate to call the present age a soft pre-revolution, not in the sense that power is shifting around much (it seems to be more concentrated than ever), but given that we are designing an entirely new Digital Society, there is potential for some radical, new vision to win out. I won’t speculate on what that vision is, or if anything will even change. Still, anyone that wishes to engage in those debates needs a seat at the table, and gaining that seat is precisely what I’m concerned with here. Hamilton, obviously, was a masterclass in this acquisition.

The 18th and 19th centuries are a Goldilocks zone of history to examine the actions and the thoughts of a man, not too far gone to accurately examine (or even find) ample documentation and reliable eyewitness accounts, but just far enough in the past that communication was still restricted to letters. Just as interesting as Chernow’s biography is Joanne Freeman’s collection of the works of Hamilton, a book I was able to find due to a rather serendipitous visit to Yorktown and Williamsburg over Memorial Day Weekend. Hamilton was a prolific writer, often drowning his opponents with words: there are 27 volumes of Hamilton literature in Columbia’s collection, and who knows what else was lost to time. Though his public articles (The Federalist Papers, etc.) are numerous and well-studied, Freeman’s book also compiles intimate letters to friends and family, revealing a complete portrait of this brilliant, volatile, principled Revolutionary.

The benefit of time also aids our ability to study the acquisition of power, or how one moves up in a position to enact their desires. Jobs and Musk, for example, got to tell their stories while still alive, which gives us reason to be skeptical of their ongoing stories though they are (obviously) much closer to the Digital Society than Hamilton was. Every man has an incentive to paint his successes as his own, to make the ascent that much steeper and more treacherous. This isn’t so much a deceitful or conniving trait as it is the basic human tendency to wrap a clean narrative over what is often a weird, somewhat random collection of events that we call our personal history.

Whether it’s Jobs, Musk, or Hamilton, however, the players of the games don’t seem to change much. At the two extremes of the spectrum, I posit that there are two fundamental power roles: arbitrageurs and builders. Though I believe that all players have a “fundamental baseline” to snap back to based on nebulous personality traits, people can certainly oscillate between arbitraging and building roles given that power itself is a fluctuating quantity. Though people might overall be either role in sum/expectation, of course there is a multidimensional aspect to each: one can be a political builder and an economic arbitrageur, for example (placing greater weights on either the political or economic power). Mathematically, a politician may be an economic non-player, a builder in the political arena and an arbitrageur economically: call it a 90-10 identity split and a 70-30 power split for a 0.9 x 0.7 + 0.1 x 0.3 = 0.66, or a weaker builder. People may even have sympathies for one type of role, but act almost entirely in the opposite without even realizing as such. I would argue that Steve Jobs was an example of this contradiction, a man who saw his role as that of a pure, scrappy builder but who more often thrived and innovated in the Old Money worlds of marketing, media, and managerial design.

Given that there always exists a tension between the present and the future, the main point of distinction between the two roles is that of the empircial reality of power versus the theoretical notion of it. Arbitrageurs, often prototypical insiders, refine and exploit inefficiences of the present system for gains in power, while builders, often prototypical outsiders, cast their hopes in new institutions that may or may not usurp the old guard. I also tend to believe that the population distribution of arbitrageurs and builders are highly, highly skewed towards arbitrageurs once we surpass some basic level of competency or ability, in part due to the high death rate of new institutions. And, as I will further argue with Hamilton, I believe that although being a builder sounds much better, it is not a priori an advantage or a morally superior state in the struggle towards influence even though it often seems praised as such. Lastly, along this vein, as I hinted at using the word “innovated” while seeming to call Jobs an arbitrageur, I do not see either of these roles by themselves as synonymous with value-creation or historical importance: the most reductive example of these two roles would be to contrast a boring, Patagonia-clad Stanford MBA at some Palo Alto VC fund and the wiry, self-taught hacker or researcher. Although much of modern media has dedicated substantial attention toward the glorification of the latter, these “literal builders” are just as often arbitrageurs, supplementing their influence with large, prestigious institutions like an MIT/Harvard education and patrician heritage. One should not conflate the verb “to build” with being a builder, but rather to ask what exactly one is build-ING.

Indeed, one of the most important principles of amassing influence is to know when to oscillate between these two roles in different domains, or at least feign as such. All of the Founders were working towards some version of a new government, and thus could mostly be said to be political builders to varying degrees (obviously with some exceptions, Adams for one thinking monarchy was inevitable). However, in most domains, they were heavy arbitrageurs. Washington, a slaveholder, was tied to the agrarian South and amassed his reputation in the (British) military as many famous historical leaders have done. Jefferson, another slaveholder, serving six years in the House of Burgesses, could not have been more firmly entrenched in the Southern economic, social, and political scene. The problem with this principle is that one must have a role to oscillate between–switching often requires some cachet to spend in the first place. The domains where this cost doesn’t seem to be as important are knowledge-based mediums like writing, as Hamilton showed with his career, but I would argue today that the ubiquity of content platforms today has made this route increasingly less probable to exploit. How does one “get noticed”?

Hamilton, an orphan with zero cachet, had a knack for impressing powerful men, as he would never attend King’s or come to America in the first place without his highly popular Carribean hurricane account in his local newspaper, which circulated across the colonies like wildfire. Without any cachet, one must essentially tie one’s self to a master and hope for their competency to develop, building up social or political (but scarcely economic) credit within the institution. Hamilton’s service to Washington as an aide-de-camp during the Revolution was inarguably the most important segment of his career as it built Washington’s unlimited trust in Hamilton, and demonstrates the importance of the right pairing with said master: pure arbitrageurs and pure builders are often a potent combination. Hamilton and Washington were both beyond lucky to have each other. Without Hamilton, or if Washington’s sympathies lied more with Secretary of State Jefferson, it seems highly likely that the confederation would’ve dissolved quite rapidly: no centralized debt implies continual inflation and higher foreign interest rates on US debt. Higher variance in state economies would mean the rich get richer, and that state interests would also increasingly diverge. If Jefferson had his way, the executive branch would do nothing, and important, time-sensitive legislation would languish in the legislative. Would it be outrageous to suggest more rebellions would’ve surfaced? More interstate squabbles? Washington’s legacy would look quite different without Hamilton’s innovations. Hamilton, similarly, was able to take such drastic measures and liberties with implied powers because criticism of Washington was political suicide (and Washington, for his part, did earn this reputation as a principled decision-maker, even if he was no policy genius himself).

Another principle of heirarchy-climbing seems to be to play as many games as possible to maximize variance of experience. As Paul Graham writes “More often people who do great things have careers with the trajectory of a ping-pong ball.” Part of this was due to the nature of the Revolution, another in part due to the reality that intellectual hierarchies of the day were so less concentrated and well-defined, but pretty much all of the Founders had a vast array of interests. I’m not sure how this ports into today’s world where specialization is more necessary due to complexity of understanding. Being at the forefront of two different domains today is much greater task than it was 250 years ago even after accounting for more accessible information.

The most consistent principle I find across any personality type or skill set for wild success in any domain (besides inheritance) is simply “informed ignorance.” By this, I mean a baseline level of inherent ability paired with a total lack of insight on how difficult the task will truly be. I think that’s why success typically comes when you’re young or never. You have more ability than ever when you’re older (except if you’re an athlete), but being able to calculate the true cost of a goal is usually more than enough to discourage a rational person from even trying. So rational pursuit of worthy goals ironically requires a down payment of irrationality.

I suppose this requirement is typically why the most accomplished among us, like Hamilton, have brutal ends. Life is fairly tragic any way you cut it, but even more so for those who cherish a degree of optimistic delusion. It totally blinds you to some relevant aspect of reality. Hamilton was notoriously without emotional restraint, and his focus on honor led to his death at the ripe old age of 49.

But is it the years or the mileage? I think the reason to play any sort of game is to have fun, not live as long as you possibly can. Comfort has never been an ingredient of success. Indeed, probably the foremost definition of success is to reach your goals despite the suffering and brutality of the day. Hierarchies are becoming less detached from the physical world, but things still advance by simple elbow grease, nothing different than Hamilton’s day.