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.

On the Self-Importance of MBAs

Kelly Fee, a Booth alum, recently posted A Call to Re-brand for MBAs (specifically in tech).  It relates to a lot of conversations that I’ve had about the value of an MBA – I’ve seen many fellow students post that they agree and are happy that someone has expressed what they haven’t been able to say.  I’m all for MBAs representing themselves well out there, but I disagree with the crux of her post.

My reaction to Kelly’s “Three petitions for MBAs in tech”:

Please stop belittling the MBA. You make yourself look bad.

“If you got nothing out of your MBA experience intellectually, it’s your own fault” – I agree with this on the surface.  Business school is an awesome place to explore new interests (academic, experiential, etc.), and I’ve viewed it as a sandbox in which to try new things.  Personally, I de-emphasize class/grades, and I spend a ton of time working for free for super smart people in spaces in which I’m interested – this is one of the biggest benefits of Booth.

You can learn cool shit in business school – no argument there – but that is not where the differentiated value is (remember Matt Damon in that Harvard bar?).  The two main things business school does for people (like it or not) are:

  1. Brand you – It’s hard to get in, and top schools do the hard work of vetting out prospective students.  By getting into school, you place yourself in “elite” company and will reap the benefits of this in the eyes of employers who want to hire smart, driven people.
  2. Give you a network – Call it a “2-year ‘break'” if you want, but that’s what it is, and that is OK.  I’ve met incredibly smart, interesting, genuine people during my time at Booth, and the deepest connections that I’ve made have nothing to do with “school”.  Early morning stumbles down 6th street after Austin City Limits, 3am post-TNDC (Thursday Night Drinking Club) tacos with my buddies, watching I Love You, Man four times since September – those are what make school worth it. Business school is awesome and fun, and that is OK – I don’t feel the need to apologize for it.

This is not to discount the knowledge that you can gain, but I can Google how to unlever beta.  You can learn the nuts and bolts of business anywhere – but branding and networks are more elusive, and those are the real competitive advantages that you enjoy as an MBA.  If you think otherwise, I’d be curious as to why you’re a better candidate for a position at Google than the person who has worked there for six years.

I don’t belittle my MBA, but I do have an opinion on what it is (and what it isn’t).  I love school, and I would do it all over again – but don’t tell me what business schools means to me and how I should represent it.

Please own your secretly intense side

“Please be authentic in speaking about your B school experience and stop being a punk” – what does this even mean?

Some people study a ton for the GMAT and some don’t have to (I did); some people freak out during recruiting and some don’t (I didn’t).  Kelly says that “the journey of personal and professional self-discovery accelerates in business school and the majority of people leave changed” – uhh, I guess?

Getting into school is hard.  Getting a job can, of course, be stressful – but it’s easier to do in business school than it is almost anywhere else.  Successfully graduating from business school is a joke.

I don’t understand the plea, so it’s hard for me to take action.

Be honest. Be humble

100% agree.  Kelly correctly says “they care about your value add, so let’s roll up our sleeves do our core jobs well, eh?”, which doesn’t really jive with her apparent disappointment at being asked about powerpoint presentations.

I actually think this is the single biggest reason employers (or other employees), at times, don’t like MBAs.  The impression is that MBAs think they are better than other people; if you want people to respect you (especially in a results-oriented environment like Silicon Valley), do a good job – it doesn’t matter where you went to school.

I recently worked on a project for a startup with someone who said “I’m an MBA student; I’m not here to do grunt work.”  That is fucking insane.

A big part of the reason MBAs get discounted is that people would rather work with people who are cheaper, more humble, and who have been actually working for the past two years.

If I had a plea to business school students, it would be to remember that you’re not that special, so enjoy what you’ve achieved and been given, and recognize that that degree doesn’t mean shit when it comes to winning a deal or getting that new product to market… though that classmate of yours on the customer’s procurement team may be a good first phone call.

Venture Capital & Tech Readings

This year at Booth, I’m serving in a Career Advisor role for the venture capital group, and I’ve been asked quite a bit about what people who are interested in the industry should be reading.  There is a ton of stuff out there, and it can be overwhelming, so I tried to put together a page of interesting stuff that would help people get started.

I’ve published the list here, where I’ll periodically make updates.  If you think I’ve missed something important, please let me know and I’ll add!


Four Pillars of Execution

I’ve asked many people a version of the question – “what makes a person successful in this role”, and the answers are pretty standard.  Recently however, I asked this question of someone who was to become a mentor, and he gave an answer that was both concise and comprehensive:

Be humble.  Be aggressive.  Be proactive.  Be precise.

As I’ve begun executing by these principals, I have been able to trace every single error or failure on my part to a violation of one of these pillars.

Humility – This has, admittedly, not always been a strength of mine, but the more I learn and pay attention, the more I think about how wise Plato’s Socrates was when, in The Apology, he said:

For my part, as I went away, I reasoned with regard to myself: “I am wiser than this human being. For probably neither of us knows anything noble and good, but he supposes he knows something when he does not know, while I, just as I do not know, do not even suppose that I do. I am likely to be a little bit wiser than he in this very thing: that whatever I do not know, I do not even suppose I know.”

Most people I know are and should be proud of their accomplishments – but it those who have accomplished great things and who continue to believe that there is so much else out there to learn that impress me the most.  As hubris and arrogance become part of someone’s persona, the absolute value of their contributions as a leader and/or contributor diminish.  People can, of course, get away with this lack of humility, but that does not mask the fact that it is a net negative in the aggregate over the long run; pride and confidence are important (I would argue critical) traits, but when unchecked by humility, they lead to a lack of awareness and limit the ceiling of one’s success.

Aggressiveness – This is something that I had always considered a strength, but by raising the bar and treating tasks as absolutely critical, I can now see that I was not properly calibrated for what it takes to aggressively execute in a startup environment.

An example:

12pm.  We have a mission critical legal document that needs to be proofed and executed by 9am tomorrow to secure financing (though we don’t technically need to send out until 1pm).  I send an email to the lawyer with a note that this is super important and needs to be done by midnight (9 hours early!).

2pm – He responds saying that he will get to it ASAP.

7pm – I follow-up via email just to be sure we are on track (he said we were good, so I’m really being extra diligent on this one).

11pm – I follow-up again via email, a little worried, but I built out that awesome cushion, so shouldn’t be a big deal.

1am – He responds via email – day was crazy and wasn’t able to get to it; will get someone on it first thing in the morning.

1:05am – I thank him via email and say by 8am is fine.

7:30am – I email him with a message of urgency.

9am – Miss deadline.  I fucked up.

This is just one example, but it’s one I lived through, and when that deadline hits, there is only one person responsible here – me.  At each point on the timeline, I made a critical error in aggressively ensuring that we met our goal.  Phone calls are generally more effective than emails, and to make sure that a lawyer (with many clients) has this top of mind, I need to be all over this.  If he can’t promise delivery, he needs to find someone else at his firm to bang it out; if he can’t, there are plenty of law firms out there, and I’m likely no more than a 2nd degree LinkedIn connection away from most.  It doesn’t matter that I prioritized the ask or that I built in wiggle room ahead of the deadline or that I pinged him five times letting him know we need this.  If anything, it shows that I was aware of the importance of the issue, but still failed to find a way to make it happen because email is easier, and I didn’t have his number, and that 9am deadline was a little arbitrary anyways, and he said it would be all set, and “I did my job”.  My job was to get the document executed, thus I did not do my job.

Being aggressive doesn’t mean being a jerk, but you can bet if some other MBA intern called up the lawyer at 1pm with a critical ask and ensured delivery with an explicit set of asks and deadlines, that was getting done ahead of my nice emails sent at socially acceptable intervals.

Pairing humility with aggressiveness is generally a recipe for success.

Pro-activeness – a little more generic, but important to both a company and to personal growth.  Thinking strategically while executing on the ground level can be difficult, but the benefits of looking ahead, both for disasters to avoid and for opportunities to exploit, can be a game changer.  When you have downtime, refresh yourself with a context switch and find a place to add value; maybe it’s a customer in the pipeline where you have the right inroads, maybe it’s a potential advisor that you could catch up with for 15 minutes to give an update, maybe it’s looking at the calendar for a meeting that could use extra prep work.  Don’t wait for someone to tell you what your next task is; find a task that excites you, and do it.

I often hear people complain about stagnation in their role.  In a startup environment, if you feel this way, you’re probably right.  And it’s probably your fault.  I’ve found that there is a lot of correlation between being proactive and being aggressive – but I think the difference is worth calling out.

Precision – While the other three pillars are more character/personality based, this is one that stands a bit on it’s own – delivering good work through attention to detail and precise execution.

This doesn’t need a lot of expounding, but I do think that being aware of the process through which you deliver your most precise work is important.  Some people work better when procrastinating, while others needs to plan well in advance; some like to work alone and finish a project in one go, while others prefer to iterate and get feedback along the way from others.  Regardless, precision is one thing that you absolutely cannot succeed without (especially when you are in more junior positions where granular analysis is so critical).

I recently helped conduct an interview, where each of the other three boxes was checked with ease, and it looked like we had a deal.  When an exercise (sent as a baseline test for competency) was turned in that fell short of the level of precision expected, the process was stopped dead in its tracks.  Non starter.

This isn’t a scientific analysis; others will have opinions on the nuances of the above, and on the weighted importance of each.  For me, I make a concerted effort to align my work with these four pillars, and by tying my failures back to each of them, I have tangibly improved my execution.