Hillbilly Elegy: Not a Book Review (Some Thoughts on Empathy)

With eight flight segments and plenty of downtime over spring break (last one ever!), I was able to crush through some of my reading list, and Hillbilly Elegy by J.D. Vance was at the top.  It’s become very trendy for my more liberal friends (and media) to drop this into conversations as an explanation for how and why Donald Trump has somehow become President of the United States of America, and based on some brief web searching, there are plenty of opinions both ways on Mr. Vance, his book, and what it all means – but that’s not what I’m here for.

For those of you who don’t know, “Hillbilly Elegy is a passionate and personal analysis of a culture in crisis—that of white working-class Americans” – full synopsis here.

I didn’t really have a goal in reading the book, other than to see what everyone was talking about – but I quickly found myself reacting to almost every story in one of two ways; (1) unintentionally condescending (“yep that’s what I’d expect from a redneck”), or (2) viscerally empathetic (“holy shit, I think I might sort of get this”).  I’m sure people across the spectrum would react to each piece of this book differently – but I grew up neither rich, nor poor, and I increasingly have a difficult time relating to those who religiously (small “r”) regurgitate Bill O’Reilly or Rachel Maddow’s talking points.  What struck me the most about those moments of empathy (not sympathy) were that they were orders of magnitude more intense than those things that I found disturbing about Mr. Vance’s upbringing.

Two episodes particularly struck a chord:

In his younger years, J.D. took it upon himself to sucker punch a bully, and though he feared the worst, in the aftermath he sensed a “hint of approval” from his teacher who gave him a token punishment and a seal of approval from his grandmother who told him, “sometimes, honey, you have to fight… it’s just the right thing to do”.

For three years in elementary school I was mercilessly tortured by a classmate (let’s call him Brian).  Unlike Middletown, Ohio (as I imagine it), Milton, MA does not condone playground justice in any way – but after yearof guidance counselor sessions and “friendship meetings”, nothing changed and I was miserable every day at school.  Then, on my first day of fourth grade we had a little scuffle that resulted in another parent conference, in which the guidance counselor suggested that I switch classes to fix the problem.  I was not in this meeting, but it is my understanding that my father (who was quite a large man and happened to have been drafted by the Dallas Cowboys in 1971) called the counselor (who was rotund and whose name was Peggy) “Ms. Piggy” and told her that moving forward “my son has explicit permission to punch this kid in the face the next time he lays a finger on him”.  Well, about 15 hours later, Brian tried to physically remove me from a chair he deemed to be his, and he ended up with a bloody nose amidst a pile of overturned desks and chairs.  I ended up in the principal’s office, listening to how my parents were “promoting violence in the school system”, and much like young J.D. was pretty sure I was going to be in a lot of trouble.  Brian never picked on me again, and the only further mention of the incident in our house was that there was a difference between what I did and starting a fight – and that I was never to do the latter.

In reading his story, I could feel the helplessness of a young boy in a school system that couldn’t/wouldn’t help in the face of bullying, and I can remember the soft approval from family that I knew would have my back, regardless of what else I’d have to face out in the real world.

Fast forward to Yale Law School, and J.D. is at a recruiting event for a prestigious law firm (just think Leo at that dinner on the Titanic).  Not knowing what to say, how to say it, or what fork to eat with (even though he looked the part of a typical white dude), he was flustered and barely keeping above water.

I, weirdly, didn’t own a suit until I was a junior in college (what’s wrong with khackis and a blazer?) – and I remember throwing it on for one of my first big recruiting events at an investment bank, for which I had made it to the in person phase of the interview process (they even paid for my train to NY!).  I believe my discomfort was probably 1/100th of what J.D. felt, but I remember feeling “less than”, and I remember resenting 75% of the people in the room, with their scripted Ivy League recruiting pitches and refined demeanor.  Due to generous financial aid and family that stretched their limits, I was lucky enough to have gone to school with people like this for years – but this was different and I was in over my head.  This was a playing field that I was ill equipped for, and I could feel it (I was also not qualified for the job, which I did not get).

For some reason, both those stories really hit home for me, bringing back memories and emotions that I hadn’t honed in on in a long time.

I started this post by thinking of how to tie this into VC and startups – “you are not always the target customer”, “don’t assume you’re the smartest person in the room”, “figure out why they think this is something to dedicate their lives to”, “diversity is not only right, but it can be profitable”.

But fuck it.  My takeaway is that I am going to try to bring more empathy into my decision making processes, in general.  I could have talked about Mr. Vance’s recollections of attempted murder, abusive relationships and drug-fueled destructive behavior – but for me, in this case, it’s the similarities that I’ll focus on, when comparing my experience to those of someone whose life has been so very different from mine.

The more we can do that, the better conversations we can have, and the more productive we can be in our relationships and in/across our communities.  We normally don’t have the luxury of reading someone’s memoir to hash these things out, but with a little effort, it can be done.

The Need for Authoritarian Leaders

On a bit of a 6+ week adventure (SF -> Boston -> Maine -> Greece -> Croatia/Bosnia -> Doha -> India), I’ve been able to make quite a dent in my to-read list; near the top of that list was Nathaniel Philbrick’s excellent In The Heart of The Sea.  It’s the story that inspired Moby Dick, and a bad movie (I’m told) of the same name was recently made.  The book is great; I recommend it.

After feeling a bit like I myself had survived a harrowing expedition through storms and disaster across the Pacific, There was a line towards the end that shook me back to my current context:

“Modern survival psychologists have determined that this “social”—as opposed to “authoritarian”—form of leadership is ill suited to the early stages of a disaster, when decisions must be made quickly and firmly. Only later, as the ordeal drags on and it is necessary to maintain morale, do social leadership skills become important.”

Analysis of leadership is not hard to come by (sand:beach :: leadership discussion:business school), but the balance between social and authoritarian leadership styles is one that I spend a great deal of time thinking about, both on a personal level and in evaluating early stage teams.

The whaleship Essex, while not a startup (it was actually quite a seasoned vessel), encountered great disasters that required decisive action on the part of it’s leader; Philbrick (along with cabin boy Thomas Nickerson, from whose notes Philbrick draws much of his story) contends that Captain George Pollard’s democratic approach to decision making and deferral to his officers played a large role in the ultimate fate of the crew.

While I haven’t heard of a sinking startup that resorted to cannibalism, the path along which startups grow is treacherous, and the authoritarian leadership required to steady the ship amidst the storm (see what I did there?) is certainly a prerequisite for a strong CEO.   Beyond that, however, the dynamic of the company will inevitably change as it goes from a few people in a garage (did you know that’s how some companies start?!) to a larger, more stable (hopefully) company, and as this happens, the skills associate with social leadership will become more important.

Scaling a company, and building a healthy corporate atmosphere is a complicated topic, and there are many schools of thought and accompanying examples of the “best” methods.  As I discussed in Hercules v. Theseus, brilliance and force are best when paired with empathy and humility, but at the earliest stages of a startup, an authoritarian style is a better indicator of a leader’s ability to build a truly great company from scratch.

In his must-read book, Originals, Adam Grant talks about forming coalitions, and the personalities required to get a cause of the ground compared to those required to scale it to a place where it has great impact (great ideas do not equate to success; great execution does).  Using the women’s suffrage movement as an example, he discusses how the original members of a group are generally the most radical, but once momentum is gained,  tempered leaders are more effective in forming coalitions that are required to foster a culture that allows the movement to reach scale.  There is a parallel here (albeit not perfect) where early company leaders must be fanatical about their company, and must be willing to confidently make difficult decisions and execute aggressively in order to get to a point where they can afford to focus more on morale and less on keeping the company alive.

As I think back to some of the deals that I’ve evaluated, the area where I’ve become the most cynical (e.g. where I’ve improved the most) when looking at deals, is team.  There are a lot of great ideas out there, but the number of people capable of executing on these ideas is much smaller; a passionate, authoritarian leader who can get shit done and knows how to coax the same out of others is so critical that when you hear someone say “I’d back her without even hearing the idea”, it’s barely an exaggeration (and it makes a lot of sense).

Bold decision-making does not mean recklessness, and it also doesn’t mean ignoring all advice or being a complete asshole all the time; it is, of course, not that black and white.  Captain Pollard may have been well liked, and he may have been a fine captain under certain circumstances, but he goes down in a storm 10 times out of 10 (in fact, he managed to go down twice before forced retirement), but in industries where storms are frequent (whaling and startups), the leader who, with the appropriate experience and wealth of knowledge, can command the respect of her team through bold decision making and ownership of responsibility, is a ship’s only chance.

Hercules v. Theseus

After an incredibly rewarding/challenging summer working for the venture capital firm, Data Collective (dcvc.com), I took a planned hiatus – some much needed family time up in Maine, along with the more stereotypical MBA summer travels to Greece and Croatia.

Having decompressed a bit, I found myself procrastinating – “this isn’t a travel blog, so I’m not going to post pictures of Santorini and rave about the local wines”, “this isn’t a book review blog, so I’m not going to talk about Edith Hamilton’s Mythology, and how it provided a streamlined escape through the annals of Greek Mythology, while I wandered around Athens”, etc.

I hate excuses, and I dislike inaction – so this should be the beginning of a more consistent cadence of posts – most will loosely tie into the world of startups – technology, markets, trends, leadership, legislation, companies, people, etc.

So – some thoughts on idols and leadership vis a vis Hercules.

When downloading the aforementioned Mythology, I was excited to dive into stories of the gods and heroes, the basics of which I had vague outlines of in my head (either Perseus or Theseus killed Medusa… and the other killed the Minotaur… and someone’s dad jumped off a cliff because of a white sail… the gods were all assholes…)

The Greek hero of whom we hear the most is generally Hercules; the last Hollywood stab at Greek mythology that I saw was The Rock’s excellent confidence man portrayal of the legend in Hercules – though I admit I can not be unbiased when it comes to The Great One.  Hercules is so amazing because (due to his half-divine background) he could do things that no one else could; the tales are too numerous to recount, but he slayed things like this, this, and these as part of his 12 labors; he played life on hard mode, and generally could not be stopped.

The problem with Hercules is that he was also incredibly unhinged, and other suffered.  Among his indiscretions, he killed his music teacher (by accident) because he didn’t like the material, and he murdered his entire family (influenced by Hera; the catalyst for the 12 labors).

Despite the decidedly murky other side of the coin above, Hercules was the revered as the greatest hero of Greece.  In Athens, however, things have been viewed a bit differently.  As Edith Hamilton notes:

The greatest hero of Greece was Hercules. He was a personage of quite another order from the great hero of Athens, Theseus. He was what all Greece except Athens most admired. The Athenians were different from the other Greeks and their hero therefore was different. Theseus was, of course, bravest of the brave as all heroes are, but unlike other heroes he was as compassionate as he was brave and a man of great intellect as well as great bodily strength. It was natural that the Athenians should have such a hero because they valued thought and ideas as no other part of the country did.

Theseus’ accomplishments were also many; he had some labors of his own – none of which were motivated by domestic violence – and he killed The Minotaur.  He also talked Hercules out of suicide after the whole murdering his family thing.  It’s not these feats that distinguish Theseus, however – it’s what he did not do that was so impressive.

His humility especially shines through in two of my favorite stories.

First, upon becoming king of Athens, he relinquished his power to the people in what was a very out of character move for power hungry, *narcissistic* characters of Greek mythology:

So Theseus became King of Athens, a most wise and disinterested king. He declared to the people that he did not wish to rule over them: he wanted a people’s government where all would be equal. He resigned his royal power and organized a commonwealth, building a council hall where the citizens should gather and vote.

As someone who gets chills thinking about George Washington, in the style Cinncinatus, relinquishing the opportunity to run the show as a military dictator, I’m surprised I had never heard (or hadn’t remembered) this version of Athenian democracy’s birth.

My favorite story, however, was his attack of Thebes (something he did not want to do, but did out of a moral obligation).  He marches in and conquers (as one does), but once his objective is complete (allowing the survivors of a previous battle to bury their dead) he leaves.  Again, not a typical move for a victorious Greek.

I see many (mostly good) articles on what makes a good leader today, mainly as it relates to building and running technology companies.  Empathy and team building are always emphasized as top priorities, but oftentimes the people that rise to celebrity status (e.g. Steve Jobs and Elon Musk) seem more like Hercules than Theseus.  It is, of course, not black and white, but the general portrayal of both Jobs and Musk is one of brilliant innovator with disregard for the human beings within his sphere.

While they are surely the exception rather than the rule, I find it interesting that we worship these Herculean figures (who we no doubt need to move mountains), when it is far more impressive to accomplish these massive feats of (innovative/intellectual) strength while remaining humble and empathetic.

When evaluating teams, I have found that there are plenty of smart people out there, but at a certain part, IQ is pretty binary, and in the world of early stage technology, there are diminishing marginal returns.  Very rarely do I come out of a meeting with a company and think “wow, we just met an idiot”, but it’s not uncommon to think something like “smart person… and she knows it – seems to lack self awareness and I worry about her ability to attract good people and overcome the inevitable speed bumps ahead”.

Bring me a true Hercules and I’ll get on board, but for my money, I’d prefer to back, help and commit to a Theseus 11 times out of 10.