My favorite books of 2018

Over the past year I spent a lot of time on the subway reading books. Here’s my year-end list of favorites. If you want a look at what else I read in 2018, you can check out my reading log here.

Have any recommendations or books I missed on this list? Please give me a shout in the comments section or shoot me a note.

Enjoy the list and see you in 2019!

General non-fiction

  • The Literary Churchill. My first Churchill biography. The Literary Churchill takes an interesting approach to its subject, trying to explain his life not through his actions or his policies, but through his reading material. This book will teach you about Churchill and about how what we read defines us.  

  • Seven Brief Lessons on Physics. An enlightening little book on physics. Carlo Rovelli first published these seven essays as a Sunday series in his local newspaper. The result is an Italian stroll through the principles that govern our world. A great read over coffee on a weekend morning.

  • Bad Blood. You’ve already heard about this book and about how you have to read it. The movie should be fun.

  • Educated. A memoir about finding knowledge for yourself. “In retrospect, I see that this was my education, the one that would matter: the hours I spent sitting at a borrowed desk, struggling to parse narrow strands of Mormon doctrine in mimicry of a brother who’d deserted me. The skill I was learning was a crucial one, the patience to read things I could not yet understand.” This book will remind you what it is you love about learning and reading.

  • Red Notice. Probably the closest look you can get at the wave of capitalism that broke across Russia in the 1990s and the pool of corruption it left behind in its wake.

  • Barbarians at the Gate. This book details one of the all-time great bidding wars in the history of Wall Street. A fantastic piece of journalism that provides a detailed view of how deal-making actually happens in the upper echelon of buyouts.

  • How to Change Your Mind. A book about the emerging science of psychedelic-aided therapy. I didn’t love this book, but it did make me think about how our minds work and how we can strive to stay open-minded as we age. Once you start this book, you’ll find yourself bringing it up in conversation constantly.

Business non-fiction

  • 7 Powers. Operational excellence does not equal long-term sustainable value. Instead, it’s using that operational excellence to build an unassailable advantage that creates the long-term value that comes from high market share and high defensible margins. With 7 Powers, Hamilton Helmer takes the best insights from Porter’s theory of competitive strategy and turns it into a digestible reference to use during points of flux in a company’s trajectory. Highly recommended for product people.

  • The Score Takes Care of Itself. Do the little things right and the score will take care of itself. Bill Walsh’s treatise on leadership after a career in which he took the Niners to three super bowl championships.

  • The Phoenix Project. All of the groan-inducing, cringe-worthy business fiction of Eli Goldratt’s The Goal is back and better than ever in The Phoenix Project. A great, fun read for anyone working within a product organization.

  • Beyond Entrepreneurship. I watched a Reed Hastings lecture. He mentioned he tries to read the first 80 pages of this book once a year. So now I do, too. A good refresher on what great leadership looks like and the importance of setting a vision within a company.  

  • The Hard Thing About Hard Things. A book of “most important rules” and hip-hop epigraphs. Though tailored for the founder or CEO, The Hard Thing About Hard Things is a great read for anyone who knows how difficult startups can be (no matter the role) and wants well-worn advice on how to survive.


  • Stoner. “Sometimes, immersed in his books, there would come to him the awareness of all that he did not know, of all that he had not read; and the serenity for which he labored was shattered as he realized the little time he had in life to read so much, to learn what he had to know.” This novel is one of the better works of American literature I’ve read in a long time. The book’s protagonist, William Stoner, comes of age on the barren soil of a Missouri farm before attending the local university for agriculture school. There, amidst the trappings of chinch bugs and manganese, Stoner takes a required course in English literature. In the hazy afternoon of that classroom, the words of Shakespeare’s Sonnet #73—”this thou perceivest, which makes thy love more strong, To love that well which thou must leave ere long”—set him in reverie. When he awakens, his life has found a new path: teaching. A great campus read on finding your own purpose and happiness in life.

  • The Moon and Sixpence. I first read the name Somerset Maugham in the byline of an epigraph. It was a suitable introduction. Maugham’s writing—tight, dry, British—lends itself to quotation with ease. He’s also very funny. The Moon and Sixpence, Maugham’s novel based on the life of painter Paul Gauguin, lends itself both to its author’s quiet humor, and to his meditations on work and purpose. For Maugham’s painter protagonist, it isn’t fame or acclaim or success that he chases. It’s beauty. Beauty, and what it means to find it in life, emerges as the dominant theme of this book. It shows itself most in the protagonist’s monastic pursuit—his paintings, and the dark shroud of understanding contained within them, are its explicit manifestation. But beauty reveals itself in other, subtler ways throughout the novel. There are characters who find beauty in quiet, apartment-bound relationships, characters who find beauty in the families they build. It’s a nudge from Maugham. Create something. Make it beautiful. Be at peace. — Great book.

  • The Shining. A happy story for winter in the mountains. A fun way to dive deeper into the mythology of the movie while you test the heart rate monitor on your Apple watch.

Remembering Jest

Last week my dad and a few friends sent me Thomas Bissell’s essay on David Foster Wallace’s epic Infinite Jest. The novel turns twenty this year and is getting the new edition treatment, which includes the aforementioned essay (foreward) by Bissell.

In reading Bissell’s essay and leafing through my own marked up copy of Wallace’s hefty tome, I was reminded of what initially brought me to IJ and what I ultimately left it with.

If I’m being honest with my 22-year old self, I first picked up IJ because it was a book that I associated with intelligence. I’d heard it was the book of our generation, and an intimidating and difficult read. To finish IJ was to self-inflict upon oneself that badge of stoic pursuit, 1150+ pages of high intellectualism, a lift into that stratum of people who discuss critical theory at parties.

Of course, as I learned in reading IJ, those people who discuss critical theory at parties are the bane of Wallace. The book itself, despite everything within its pages that might label it as a work that aspires towards genius -- the endnotes, the deep tangents into mathematics, the lexicon -- is a plea to cast aside the highbrow, the ironic, and the cynical. It is a book about compassion for others. A book about “what it means to be a human being.”

This theme, casting aside irony for the pursuit of real connection with others, is all over the place in IJ, but manifests itself primarily in Hal, the precocious tennis prodigy of Enfield who “does things like get in a taxi and say, "The library, and step on it.””

“Hal, who’s empty but not dumb, theorizes privately that what passes for hip cynical transcendence of sentiment is really some kind of fear of being really human, since to be really human (at least as he conceptualizes it) is probably to be unavoidably sentimental and naive and goo-prone.”

For me, to read IJ was to follow the same arc as Hal, coming in with expectations of “hip cynical transcendence” and finding instead the “sentimental and naive and goo-prone.” In a way, I suppose it’s what it would have felt like to meet Wallace, or to take one of his classes at Pomona. Walk in on the first day of class, looking for one of the greatest minds of the 21st century, and find Dave, resplendent in Star Wars sweatshirt and bandana. Here's an except from a great Quora answer on what it was like to take Wallace's class:

“On the first day of class, Dave wore a cut-off Star Wars sweatshirt and a bandana to tie back his greasy hair. His spectacles gleamed. If I had been expecting the wunderkind of Infinite Jest, my idealized visions crumbled as I watched him spit a stream of black tobacco spittle into a Slurpee cup.”

Dave, proclaimed by critics as the literary genius of his generation, who wrote sentences like this:

“...the air over the table like the sparkling space just above a fresh-poured seltzer.”

And sentences like this:

“I like the fans’ sound at night. Do you? It’s like somebody big far away goes like: it’sOKit’sOKit’sOKit’sOK, over and over. From very far away.”

Top 5 Years of All Time: 2015, A Year in Review

In 2015, I set out to read 25 books. The goal for 2016 is 52 blog posts - one a week. I’ll be using this site as a notepad for ideas - a place to jot down what’s on my mind concerning technology, books, and anything that else that catches my interest.

With 2015 wrapped up, I wanted to reflect on the year through a list of my favorite reads and listens from the past twelve months. In deference to one of my favorite movies ever, High Fidelity, I’m taking a Top Five Records approach to the list.

For those who haven’t seen High Fidelity, its characters spend the movie lounging around a record store, coming up with top 5 lists. My brother and I have since adopted the habit, drafting top 5 lists for music, movies, ideas, cities to live in abroad, etc. It’s an effective way to structure opinion on both the abstract and the pragmatic.

A quick note on the structure of the top 5 list: its contents are in no way listed by priority or rank. The contents of a Top 5 list need no rank, for they have made it to the Top 5, and that is achievement enough. Here we go.


Top 5 Ideas I Read About in 2015

  • Aggregation Theory. How the internet enabled distribution at scale, and unlocked opportunities for new entrants to aggregate those parts of the supply chain closest to consumers. The theory does a good job of explaining the changing landscape of media, transportation, and hotels, as well as the success of Uber, WeWork, AirBnB, et al.
  • Messaging is the Future Runtime. In 2015 I became obsessed with the idea that in the mobile age, messaging apps will be where content search and discovery happen, and that they will happen contextually, not on an on-demand basis (as was the case with Google during the age of the web browser.) There was a lot of news around messaging this year. FB Messenger announced M, a semi-AI concierge that helps users find what they need (which also led to the anti-turing test.) In APAC markets, messaging apps have been the primary runtime for a number of years. Looking forward to see how this space evolves in American markets in 2016.
  • Growth v Fixed Mindset. We can always be learning and growing. I liked this read on the difference b/w those with fixed and growth mindsets, and how the latter worry not about proving themselves to third parties but about how they can constantly be challenging themselves to learn more.
  • The Evolution of Verbs in the Workplace. Benedict Evans did a good job of summarizing this idea, in which the on-premise, PC-generation of workplace tools (excel, ppt, email) are replaced by collaborative cloud solutions. These new solutions improve efficiency through the automation of manual work (e.g. data visualization tools replacing excel) or by giving users a single place to collaborate on content (e.g. users communicating on tasks in Slack/Asana/Percolate instead of through siloed email threads.) The workflows change. The output stays the same, it’s just produced faster.
  • The Tennis Ball Problem. A wry metaphor that articulates the importance of focus on a few (and not many) things.

Top 5 Stratechery Reads

2015 was the year I bit the bullet and subscribed to Ben Thompson’s daily update. It’s the best $10/month I spent all year (with the possible exception of Spotify) and how I start my morning when I get into the office. Here are some of my favorites.

  • Why Web Pages Suck. I love this post. It contains my favorite visual of 2015, the 2009-2014 comparison b/w % of consumer time spent v. % of advertising spend across digital and traditional channels (from Mary Meeker’s annual internet trends SOTU report.) The post also does a great job of explaining how programmatic advertising worked in the days of the web browser, and how the model will not transition well to mobile. In the future, native advertising (think Facebook feed and Snapchat Discover) will dominate media spend on mobile.
  • The Facebook Epoch. Facebook dominated 2015. This article explains how Facebook is winning the mobile epoch (after Google won the web/browser one) and how they’re positioning themselves to mimic the messaging platforms of APAC.
  • The AWS IPO. One of the biggest tech stories in 2015 was Amazon’s reveal of their AWS revenue numbers. Few predicted just how huge these numbers would be (~26B) or how essential AWS -- the default cloud infra provider for new companies -- would become across the internet. I like Thompson’s article as it posits just how big of a deal this is for Amazon, and what the implications are for Amazon in 5 years, when today’s startups (the majority of which use AWS) grow into massive companies.
  • Aggregation Theory. (Mentioned above in top ideas of 2015.)
  • Old-Fashioned Snapchat. I think a lot of people are still trying to get their head around Snapchat and how it will be successful long-term. “No targeting? No audience demographics? What’s the point?” This write-up is a nice outline of the brand advertising opportunity available to Snapchat, and how it’s enabled through Snapchat stories and Discover.

Top 5 Reads Directly Related to Technology/Startups

Top 5 Reads About Nothing in Particular

  • Astral Weeks, Lester Bangs. Astral Weeks was one of my favorite albums in high school. I put the title track and “Sweet Thing” on A LOT of burned CDs. This review from Lester Bangs says a lot about the album, and about human nature in general. It’s also a fascinating view into the mind of a legendary writer from the early rock scene in America -- the first exposure I had to Bangs was from Phillip Seymour Hoffman’s excellent portrayal of him in Almost Famous, so I enjoyed this deeper dive into his writing.
  • One Last Rave, Hua Hsu. This is a great profile on Jamie XX - includes a nice walkthrough on the 80s/90s dance scene in the UK and how it evolved into the music of today.
  • Hub Fans Bid Kid Adieu, John Updike. Updike takes a trip to Fenway for Ted Williams last major league baseball game. Even if you don’t like baseball, this is a must-read. At the very least, it’s a nice look into what it would be like to go to a baseball game as a literary genius. (What with the gift of perception and all.)  
  • The Five-Decade Book Party and Its Tireless Host, Warren St. John. Cool write-up on the literary parties George Plimpton used to throw.
  • Why Go Out?, Sheila Heti. I found this transcription of a Sheila Heti lecture a few years ago while living in SF, but I added it to my Pocket favorites list in 2015, so I’m tacking it on here. In today’s culture, where it’s the accepted norm to stay in and watch Netflix, to stay comfortable, this article says something interesting about why we go out and forgo this comfort.

Top 5 Novels Read in 2015

  • Moby Dick, Herman Melville. Everything is metaphor.
  • Crossing to Safety, Wallace Stegner. Friends are important.
  • In the Light of What We Know, Zia Haider Rahman. Two friends reunite after a long time apart and discuss mathematics, exile, and how they’ve lived their lives. This book will inspire you to think critically, and to keep a list of your favorite quotes.
  • Norweigan Wood, Haruki Murakami. I picked this up after a recommendation from a friend. Much more accessible than The Wind-up Bird Chronicle but still written in the same distant tone that is so unique to Murakami. I read this book in a weekend and then listened to Rubber Soul.
  • Emma, Jane Austen. This book just turned 200 years old. A really interesting look into a different time, in which people’s social motives were not so different than they are today. A masterpiece of character development and contrast -- every character represents a different, complex foil of Emma, the main protagonist.

Top 5 Non-Fiction Books Read in 2015

  • Astoria, Peter Stark. A must-read for any person from the Pacific Northwest. It used to take considerably longer to get from coast to coast.
  • Paid Attention, Faris Yakob. A great read on the current state of the advertising industry and its digital transformation. Outside of the marketing insight, this book has some really interesting passages on thought itself. Yakob shares wise words on how we come up with ideas through connecting stolen themes from the past, and on how the prodigious thinkers come up with the best ideas - that is, most ideas are bad, you need to get through the obvious ones before you can get to the margin and find the good stuff.
  • Give and Take, Adam Grant. A great business read about how takers, matchers, and givers match up in the corporate success ladder. In reading this, I was reminded a lot of the New Yorker feature on Reid Hoffman, the uber-networker who starts all of his conversations with a written agenda and ends them with softly asking "How can I help?" I liked this book - a good reminder of how to act in the workplace and in life.
  • The Design of Everyday Things, Don Norman. I picked this book up after an email from Noah on his required reading list for new PMs. It starts with the basic design principles of human-centered design: affordances, signifiers, constraints, mappings, and feedback. They're the most valuable piece of this book and a great model to keep in mind when designing anything that will be used by a fellow human being.
  • A Supposedly Fun Thing I’ll Never Do Again, David Foster Wallace. The title essay is one of my favorite non-fiction reads of all time, and probably the most endearing thing DFW put on paper. It is hilarious, relatable, and devastating in its sadness, all at once.

Top 5 Short Stories Read in 2015

Top 5 Albums Released in 2015

  • Art Angels, Grimes. Claire Boucher retains the same ethereal weirdness from her last release, Visions, but puts it through a mainstream pop filter. Great to have Grimes back on the scene.  
  • Poison Season, Destroyer. One of my favorite concerts of 2015. Bejar is the man, and this album was the perfect accomplice for my move to NYC this year. The sax on “Dream Lover” reminds me of early E Street Band -- undeniable.
  • In Colour, Jamie XX. Incredible sampling and production throughout this album. My favorite track is “Girl”, which takes effervescent vocals from Freeez’s “I.O.U.” and turns them into something distant and dreamy.
  • If You’re Reading This It’s Too Late, Drake. Drake had a big year.
  • Vega Intl. Night School, Neon Indian. It’s been fun to see the chillwave artists develop their sound over the last years. I really enjoyed this release from Neon Indian, which is an impressively cohesive album. My winner for best closing track of the year.      

Top 5 Old Albums Discovered in 2015

  • Bo Diddley, Bo Diddley. Rhythm and swagger well ahead of his time.
  • Homogenic, Bjork. I started exploring Bjork’s catalogue leading up to her headline at Gov Ball. Great songwriting. Complex beats. Incredible vocals.
  • Let It Be, The Replacements. Answering Machine is a great closing song.  
  • Head Hunters, Herbie Hancock. You’ve heard this album before, you just didn’t know it. The opening bass synth line is deep and slinky. Everything else that follows maintains a similar level of cool.
  • Fresh, Sly and the Family Stone. Sly’s departure from the mainstream into more complex keys and arrangements. When Miles Davis heard the opening track from this album, he forced his band to listen to it on repeat for 30 minutes. It’s that good.

And that’s it. 2015 was a great year. Looking forward to 2016; another year of reading, writing, and learning.

See you there.