2018 Year In Review

Dec 31 2018

To paraphrase my son Joey’s favorite Dr. Seuss book “One Fish Two Fish Red Fish Blue Fish”, “2018 is gone. 2018 was fun. 2019 is another one.”. It was quite the eventful year. We welcomed our third son Jack into the world. My hometown Eagles won their first Super Bowl in ridiculous and improbable fashion. I took on a new role as CTO of a local real estate data startup. Never a dull moment!

Reflecting on 2018, I see a clear trend in my overall desire to think and operate at higher levels of “the stack”. I’ve grown from wanting to learn how to scale software/systems to wanting to learn how to scale teams/companies. I’ve increasingly started wrestling with more global ideas and concerns, as I’m hoping my blog will show over the coming months. And I’ve tried to do all this while supporting a growing family, and as such have sought ways to remove the non-essential, e.g. goodbye fantasy football (though I hope my friends still invite me to the draft party).

I’ve also realized that it’s helpful to pair aggressive “goals” with a strong vision and mental model of the world. There are inherent peaks and valleys to life (which startups tend to amplify) so it’s important for your own sanity to understand why you’re doing what you’re doing, compare it to “reality”, and make sure these things are consistent with what you want out of this all-too-short life.

So to close out 2018, here are a few of the more interesting things I’ve read or seen over the past year. Enjoy!


The Start-Up of You by Reid Hoffman

A book I wish I had when starting my career. I especially gravitate toward the ideas of competitive advantage as an interplay of “1) your assets, 2) your aspirations/values and 3) market realities”. It puts to rest all of those debates about following your passion (2). Passion is just one component, you need a more holistic and pragmatic approach grounded in reality.

Principles: Life and Work by Ray Dalio

I’ve been a big fan of Ray Dalio ever since coming across the PDF version of Principles years ago. This fully-fleshed out book gives more of Ray’s personal backstory and provides a nice reference for all of his principles. Required reading for anyone who wants to do serious work!

Seveneves by Neal Stephenson

Yes, the plot tends to drag on at times and there really isn’t much to speak of as far as a story arc or climax is concerned, however the sheer scope of the ideas presented here is really amazing and is just a generally entertaining piece of science fiction.

On Intelligence by Jeff Hawkins

This book more than anything has caused me to question to current ideas around A.I. and seems very promising in its potential to lead to a more comprehensive approach to intelligence that goes beyond mere pattern recognition.

Batman: White Knight by Sean Murphy Gordon

I was surprised by how entertaining this story was. I don’t have a ton of exposure to the comics but being so familiar with the TV/film plot lines of the Batman universe, it was really refreshing to see a story that paints a recovering Joker (Jack Napier) as the hero trying to clean up Gotham while casting doubt on the methods and motivation of the Caped Crusader.

Boyd: The Fighter Pilot Who Changed the Art of War by Robert Coram

This might end up being one of my favorite books of all-time. I’ve always been interested in military history, but it was so compelling to read about a man who was so intense, so uncompromising, and so obsessive about his ideas. The sheer impact he had on this world (both directly and indirectly via his Acolytes) is unparalleled. Coram also does a good job to not over-romanticize Boyd’s life, casting reasonable doubt on dubious claims made by Boyd and fairly articulating how his obsessions led to his wife and kids being largely ignored. The latter never sat well with me, and it certainly taints his legacy. However, his intellectual integrity and passion are a model to strive for.


The Killing of a Sacred Deer

I enjoyed Yorgos Lanthimos’ previous film The Lobster, but the absurdity of that premise (people turning into animals if they don’t find mates) was fairly constant, and kept me from getting too engrossed into the story. The Killing of a Sacred Deer feels like it’s set in roughly the same absurd world, yet it feels much more grounded. The characters are mostly odd but when thrust into the circumstances that drive the plot, their behavior feels much deeper due to its plain blunt horror. The climatic scene is a great example of this, the protagonist performing a ritual both grotesque yet highly logical.

This movie is one of many films (Minority Report being another poignant example) that now take on a different meaning for me now that I’m a father. I’d definitely have trouble watching either film again, but am glad for having seen it once.

Three Bilboards Outside Ebbing, Missouri

While I only saw this recently and still need to re-watch it, I’m a die-hard fan of anything the McDonagh’s produce (both films and plays) and this movie ranks at the top of the list. This also felt more grounded and grittier than Martin’s past works with a much more personal and heart-breaking premise. He still maintains his trademark dark humor as well (which was at its best in In Bruges).

Captain Fantastic

I’ll always have a soft spot for stories about rebels who reject the status quo and strike their own path (a la Into The Wild). Captain Fantastic was no exception. Viggo Mortensen plays uncompromising better than most, and his kids in the movie all seem perfectly cast to both challenge and mirror him. The conclusion feels satisfying yet well-earned.


I feel like I need a few posts just to properly unpack the ideas in this series. Beautifully acted, superbly written, the second season managed to handle the requisite world-building of a second act while keeping a focus on the implications of androids becoming sentient.

Other Good Stuff

Mapping and Strategy by Simon Wardley

As I begun to transition to a more strategic role I found early on that I could use all the help I could get. Reading about Wardley’s experience helped give me ideas on how to use maps and visualizations to help me think at more strategic levels.

How to get Rich (without getting lucky) by Naval Ravikant

Bill Simmons likes to joke in non-sports contexts of certain things having high efficiency. For example, we’d consider actors like Daniel Day-Lewis and John Cazale to be highly efficient as they almost always turned in excellent performances. This tweetstorm is another example of an extremely efficient work. There’s roughly twenty tweets here and offer invaluable advice for work and life.

Barry Diller on Masters of Scale - part 1 and part 2

Really engaging profile about Diller. His ideas about learning seemed to keep “cropping up” over the course of the year. The podcast in general has awesome advice, even so these pods stand out as the cream of the crop.

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