Good Reads

My favorite book on strategy so far. Long and dense, but worth it. Goes through a historical overview of business, military and political history, and how strategy has evolved over time. One of those books that adds 10 new books to your reading list, because so many chapters reference source material that you’ll want to read in full.

So the realm of strategy is one of bargaining and persuasion as well as threats and pressure, psychological as well as physical effects, and words as well as deeds. This is why strategy is the central political art. It is about getting more out of a situation than the starting balance of power would suggest. It is the art of creating power.

The challenge for the intelligent strategist was to anticipate both the enemy and all those elements of friction and chance that got in the way. The correct approach was not to give up and assume that chaos and unpredictability would mock all plans and overwhelm best efforts but rather to prepare for such eventualities in advance.

As with all metaphors, warfare could be illuminating for business so long as it was not mistaken for the real thing.

Very dense with actionable information, to the point where it can be hard to keep up with all the content that you want to remember. Lots of insight on managing yourself and your teams in a proactive, honest and objective way to consistently get results. Especially enjoyed the section on managing companies or divisions as machines, but there are so many good sections that it’s hard to summarize.

When I started out, each and every twist and turn I encountered, whether in the markets or in my life in general, looked really big and dramatic up close, like unique life-or-death experiences that were coming at me fast. With time and experience, I came to see each encounter as “another one of those” that I could approach more calmly and analytically, like a biologist might approach an encounter with a threatening creature in the jungle: first identifying its species and then, drawing on his prior knowledge about its expected behaviors, reacting appropriately.

In gaining this perspective, I began to experience painful moments in a radically different way. Instead of feeling frustrated or overwhelmed, I saw pain as nature’s reminder that there is something important for me to learn. Encountering pains and figuring out the lessons they were trying to give me became sort of a game to me. The more I played it, the better I got at it, the less painful those situations became, and the more rewarding the process of reflecting, developing principles, and then getting rewards for using those principles became.

The Obstacle Is the Way is a book full of modern applications of all the principles outlined in Meditations (above) and other classic stoic philosophy books. It’s probably my favorite out of all the Ryan Holiday books, and one I think about frequently whenever I’m in a high-stress situation.

The more you accomplish, the more things will stand in your way. There are always more obstacles, bigger challenges. You’re always fighting uphill. Get used to it and train accordingly.

The only guarantee, ever, is that things will go wrong. The only thing we can use to mitigate this is anticipation.

In Ego Is The Enemy, Ryan Holiday takes concepts from Aurelius, Seneca and other stoic philosophers and relates them to modern examples of success. It served as a much needed reality check on my own ego.

The ambition that fueled your effort? These begin as earnest drives but left unchecked become hubris and entitlement. The same goes for the instinct to take charge; now you’re addicted to control.

At any given time in the circle of life, we may be aspiring, succeeding, or failing—though right now we’re failing. With wisdom, we understand that these positions are transitory, not statements about your value as a human being.

Picked up after seeing it recommended in a few podcasts by Alex Danco @ Social Capital. Dense, but very interesting book on the interactions between innovation in the market, financial speculation and government intervention. A lot of interesting ideas:

• It’s hard if not impossible to estimate the long-term impact and use cases for tech innovation on the scale of electricity or the internet, so most innovation at that scale is funded with no rational ROI in mind
• One way is through speculation (i.e. bubbles), with the subsequent crash/waste produced is all part of the process of innovation
• The other way is government, who plays a much larger role in innovation than we like to give it credit for, through both direct investment (especially defense departments), and dampening the crashes that speculative investment cause

Also lots of interesting lessons on company building, VC and strategy throughout the book. It’s focused really on long-term, high-level, structural aspects of business more than any specific tactics.

First, financial bubbles have been the vehicle for mobilizing capital at the scale required in the face of fundamental, intractable uncertainty. Second, the post-World War II American state, extending a diverse history of underwriting economic and financial uncertainty in pursuit of national goals, built the technological platforms on which I and my fellow venture capitalists have danced for a long generation.

I have learned that the ability of any player in the game to hedge against what cannot be anticipated – to hedge against crisis – is a joint function of assured access to cash and sufficient control of circumstances. Cash buys time to find out what is going on; control permits the player to use that time to shift the parameters of the problem.

Picked up after seeing Patrick Collison recommend it in a few reading lists. Tells the history of airlines, from when they were first created to the late 90s. Especially interesting if you work in travel, but it’s a good lessons in competition in general.

With such intense competition, interesting to see all the different ways airlines competed: focusing on cost reduction, operational efficiency, investing heavily in their brand, M&A to consolidate competition, lobbying, building a better flying experience, building new distribution channels, etc. All the major airlines had a mix of these that they were particularly good at.

Sabre was not only a way of making fees, of course, but also a distribution system for American’s own flights. Although agents could book flights on nearly any airline through Sabre, Crandall began enticing agents to skew their bookings toward American with an addictive new financial arrangement. The greater the dollar value of an agency’s business with American, the greater the percentage the agency received on the entire sum.

More wisdom than advice. Written by the president of Pixar and Disney animation, you can tell the insights in the book come from decades of experience.

When faced with a challenge, get smarter.

If we think data alone provides answers, then we have misapplied the tools. A large portion of what we manage can’t be measured, and not realizing this has unintended consequences. Measure what you can, evaluate what you can measure, and appreciate that you can’t measure the vast majority of what you do.

Two main themes I enjoyed in this biography:

1. Despite his public speaking/writing on humility, he consistently struggles between his desire for acclaim and his desire to stay humble, something you don’t see in most writing about him
2. From his scientific experiments to his political career, there is a constant focus on pragmatism over theory, which I admire

Lots of good lessons on strategy in the chapters about his time in Paris as well.

Franklin, not understanding the exhortation, bumped his head on a low beam. As was his wont, Mather turned it into a homily: “Let this be a caution to you not always to hold your head so high. Stoop, young man, stoop—as you go through this world—and you’ll miss many hard thumps.”

But just as he was not a profound religious or scientific theorist—no Aquinas or Newton—neither was he a profound political philosopher on the order of a Locke or even a Jefferson. His strength as a political thinker, as in other fields, was more practical than abstract.

It’s impressive just how thought out Peter Thiel’s strategy to take down Gawker was, and how patient he was throughout the process. It’s a great look into how Thiel thinks, but my main takeaway was the level of coordination and patience it takes to pull off a plan of this magnitude. Although the theme is conspiracy, there are a lot of lessons on strategy in general.

When you ask yourself, “Why can I not just catch a fucking break?” It is the nature of conspiracy. If it was easy, everyone would do it. Fate rarely conspired to help conspirators—and if it was on their side, why were they forced to do all this sneaking around then? No, fate sends to the conspirators of the world the best of its Murphy’s Law and entropy and crises of confidence.

Clausewitz warned generals about the “culminating point of victory.” A point where, if blindly ridden past, flush with the momentum of winning and strength, you imperil everything you have achieved.

A great book for dealing with adversity, and definitely one of the most accessible stoic books I’ve read. It’s remarkable to think that these were just the journal writings of one of the most powerful men in the world at the time. Despite its age, the issues Aurelius writes to himself about are still very relatable today.

Everything that happens is either endurable or not. If it is, stop complaining. If it isn’t, your destruction will mean its end as well so stop complaining.

Do less, better. Ask yourself at every moment, “is this necessary?”

One of the best books to read when things are not going well in a company. The theme of The Struggle is something I regularly revisit, and it’s always comforting to see just how bad it got for Horowitz before his success. Even if things are bad, at least I don’t have to IPO a dying company as the only means of survival.

All the mental energy you use to elaborate your misery would be far better used trying to find the one seemingly impossible way out of your current mess. Spend zero time on what you could have done, and devote all of your time on what you might do. Because in the end, nobody cares; just run your company.

Even if you know what you are doing, things go wrong. Things go wrong because building a multifaceted human organization to compete and win in a dynamic, highly competitive market turns out to be really hard.

I don’t follow the steps outlined in the book exactly, but it made me slow down my reading to make sure I was fully understanding each book I read. Also, really liked the concept of syntopical reading, which made me more deliberate about the order in which I read books.

When reading syntopically, the reader reads many books, not just one, and places them in relation to one another and to a subject about which they all revolve. With the help of the books read, the syntopical reader is able to construct an analysis of the subject that may not be in any of the books.

Every book, no matter how difficult, contains interstitial material that can be and should be read quickly; and every good book also contains matter that is difficult and should be read very slowly.

A great book on how to cultivate virality and word of mouth. Berger breaks down the main elements of what makes people share a product – social currency, triggers, emotion, public visibility, practical value, and stories.

What people talk about also affects what others think of them. Telling a funny joke at a party makes people think we’re witty. Knowing all the info about last night’s big game or celebrity dance-off makes us seem cool or in the know. So, not surprisingly, people prefer sharing things that make them seem entertaining rather than boring, clever rather than dumb, and hip rather than dull.

When trying to use emotions to drive sharing, remember to pick ones that kindle the fire: select high-arousal emotions that drive people to action. On the positive side, excite people or inspire them by showing them how they can make a difference. On the negative side, make people mad, not sad.

Very practical and dense with actionable tips. Especially enjoyed the sections on managing employees and executives while you scale, as it helped me become a better team member during growth phases.

Some early employees will stick with a breakout company for decades and their personal story arc mirrors that of the company. These employees tend to be hungry to learn from others, understand that the company, their role, and its culture will inevitably evolve, and are open to change. A common sign that an old-timer will work out is their eventual acceptance that their role and influence at the company will shrink in the short- to medium-term as the team scales, but that it will expand with time as they continue to learn and the company continues to scale.

The hard part of being a good CEO is that you have to be willing to let some things fall apart. You don’t have enough time to do everything well. And in practice, what that means is that there are some urgent things that you just don’t do. Getting comfortable with that takes a long time. It’s hard.

I reluctantly bought this book to learn more about data visualization while working at Plotly, and it ended up becoming one of my favorite books. It covers the fundamentals of data visualization, but the design concepts in the book are applicable to all types of graphic design. Only downside is that you’ll start over-analyzing every graph you see once you’ve read this.

It is all right to decorate construction but never construct decoration.

Graphical elegance is often found in the simplicity of design and complexity of data.

You kind of get the point pretty early in the book, but still an entertaining read. It’s impressive how far Elizabeth Holmes was able to get considering how blatantly she was lying and how early people within the organization started to realize it.

The image on the computer screen showing the blood flowing through the cartridge and settling into the little wells was real. But you never knew whether you were going to get a result or not. So they’d recorded a result from one of the times it worked. It was that recorded result that was displayed at the end of each demo.

People in her entourage like Channing Robertson and Don Lucas were beginning to compare her to Steve Jobs. If so, she should dress the part, she told her. Elizabeth took the suggestion to heart. From that point on, she came to work in a black turtleneck and black slacks most days.

A great book on decision making in situations with incomplete information, which in practice represents most decisions you have to make. Thinking in bets allows you to look at decisions more honestly, forces you to take into account luck and uncertainty, but also helps separate the result of the decision from the quality of the decision making process.

Chess contains no hidden information and very little luck. 
Poker, in contrast, is a game of incomplete information. It is a game of decision-making under conditions of uncertainty over time. Valuable information remains hidden. There is also an element of luck in any outcome. You could make the best possible decision at every point and still lose the hand, because you don’t know what new cards will be dealt and revealed. Once the game is finished and you try to learn from the results, separating the quality of your decisions from the influence of luck is difficult.

A good outcome could signal that we made a good decision. It could also mean that we got lucky, in which case we would be making a mistake to use that outcome as a signal to repeat that decision in the future

I bought this book when I started to feel that my attention span and ability to focus was decreasing. There’s 2 key lessons I got:

1. The ability to focus for long periods of time is getting more and more rare and having that ability is a competitive advantage.
2. Distracting yourself and switching tasks constantly not only hurt your focus in the moment, but reduce your brain’s ability to focus over time.

In the absence of clear indicators of what it means to be productive and valuable in their jobs, many knowledge workers turn back toward an industrial indicator of productivity: doing lots of stuff in a visible manner.

If every moment of potential boredom in your life—say, having to wait five minutes in line or sit alone in a restaurant until a friend arrives—is relieved with a quick glance at your smartphone, then your brain has likely been rewired to a point where  it’s not ready for deep work—even if you regularly schedule time to practice this concentration.

Scott Adams is known for being the creator of Dilbert, but it turns out he went through a million other things before succeeding as a comic strip writer. Although the book gets a little weird at times (hypnosis, affirmations), there’s useful advice from career and fitness to storytelling and conversation. Just don’t read his Twitter because it will ruin your perception of him.

The system-versus-goals model can be applied to most human endeavors. In the world of dieting, losing twenty pounds is a goal, but eating right is a system. In the exercise realm, running a marathon in under four hours is a goal, but exercising daily is a system. In business, making a million dollars is a goal, but being a serial entrepreneur is a system.

Once you optimize your personal energy, all you need for success is luck. You can’t directly control luck, but you can move from strategies with bad odds to strategies with good odds.

I’ve noticed there’s a tendency in digital marketing to look down on classic advertising, as if it’s an old, inefficient way of promoting a product and we’ve now found a better way to do it. The reality is that a lot of the principles in this book still hold true, and if they’re relevant 30 years after publishing they’ll probably still be relevant 30 years from now.

In the past, just about every advertiser has assumed that in order to sell his goods he has to convince consumers that his product is superior to his competitor’s. ‘This may not be necessary. It may be sufficient to convince consumers that your product is positively good. If the consumer feels certain that your product is good and feels uncertain about your competitor’s, he will buy yours.

When I write an advertisement, I don’t want you to tell me that you find it ‘creative.’ I want you to find it so interesting that you buy the product. When Aeschines spoke, they said, ‘How well he speaks.’ But when Demosthenes spoke, they said, ‘Let us march against Philip.’

I have yet to meet a person who read this book and didn’t like it. By going through an overview of human history, the book provides a lot of context to the way we think about society, government and how that could change in the future.

Any large-scale human cooperation – whether a modern state, a medieval church, an ancient city or an archaic tribe – is rooted in common myths that exist only in peoples collective imagination.

But the most important finding of all is that happiness does not really depend on objective conditions of either wealth, health or even community. Rather, it depends on the correlation between objective conditions and subjective expectations.

Didn’t enjoy it as much as some of the people who recommended this to me did, but interesting book nonetheless. It’s a smooth read and entertaining more than anything, although there are some good lessons on how a lot of useful insight can come from experimentation for the sake of experimentation.

When you have a very wide range of people who contribute without looking carefully at it, you don’t improve your knowledge of the situation by averaging.

The first principle is that you must not fool yourself—and you are the easiest person to fool. So you have to be very careful about that. After you’ve not fooled yourself, it’s easy not to fool other scientists. You just have to be honest in a conventional way after that.

A pretty quick read but lots of useful insight. Main thing I got out of this book is that becoming a star performer requires doubling down on strengths instead of trying to overcome weaknesses. It changed the way I tend to prioritize the skills I’m trying to develop.

Discover where your intellectual arrogance is causing disabling ignorance and overcome it. Far too many people—especially people with great expertise in one area—are contemptuous of knowledge in other areas or believe that being bright is a substitute for knowledge.

Successful careers are not planned. They develop when people are prepared for opportunities because they know their strengths, their method of work, and their values. Knowing where one belongs can transform an ordinary person—hardworking and competent but otherwise mediocre—into an outstanding performer.

Picked this up because I was a big fan of McCord’s famous Netflix culture deck. The book is basically the background on how the principles of the deck were thought out and actually applied at Netflix, including the challenges they came across along the way to make them work. Not life-changing but a good practical book on actually implementing the values and culture you design for a company.

When engineers start to whine about a process you’re trying to implement, you want to really dig into what’s bothering them, because they hate senseless bureaucracy and stupid process. But they don’t mind discipline at all.

They were all built upon the realization that the most important job of management is to focus really intently on the building of great teams. If you hire the talented people you need, and you provide them with the tools and information they need to get you where you need to go, they will want nothing more than to do stellar work for you and keep you limber.

Frankl goes through his time at Auschwitz, and the way he was able to find meaning and hope in his life despite the horror of his circumstance. Very well-written and a guide to finding meaning even in the worst of times, by focusing on the control we have of our own attitude towards the situation and the meaning we can draw from it.

As each situation in life represent a challenge to man and presents a problem for him to solve, the question of the meaning of life may actually be reversed. Ultimately, man should not ask what the meaning of his life is, but rather he must recognize that he is who is being asked. We needed to stop asking about the meaning of life, and instead to think of ourselves as those who were being questioned by life–daily and hourly. Our answer must consist, not in talk and meditation, but in right action and in right conduct.

The experiences of camp life show that man does have a choice of action. There were enough examples, often of a heroic nature, which proved that apathy could be overcome, irritability suppressed. Man can preserve a vestige of spiritual freedom, of independence of mind, even in such terrible conditions of psychic and physical stress.

This book is popular enough that a lot of the lessons have been distributed into all kinds of content you’ve already read online, so there are a lot of sections that can be skimmed through. Thought the chapters on variable rewards and investment into a product were particularly interesting though.

Without variability we are like children in that once we figure out what will happen next, we become less excited by the experience.

The more effort we put into something, the more likely we are to value it; we are more likely to be consistent with our past behaviors; and finally, we change our preferences to avoid cognitive dissonance.

There were a lot of parallels in this book to The Obstacle Is the Way (above). The main message Manson gives in this book is that the less you care about unimportant, trivial matters, the more you can care about what will bring you success/happiness.

There is a simple realization from which all personal improvement and growth emerges. This is the realization that we, individually, are responsible for everything in our lives, no matter the external circumstances. We don’t always control what happens to us. But we always control how we interpret what happens to us, as well as how we respond.

A question that most people never consider, is, “What pain do you want in your life? What are you willing to struggle for?”

Doesn’t go very deep but a good overview of different irrational factors that influence people’s decisions. Found it more useful as a list of pitfalls to avoid rather than a list of tactics to use.

Although consistency is generally good, even vital, there is a foolish, rigid variety to be shunned. It is this tendency to be automatically and unthinkingly consistent that Emerson referred to. And it is this tendency that we must be wary of, for it lays us open to the maneuvers of those who want to exploit the mechanical commitment consistency sequence for profit.

People seem to be more motivated by the thought of losing something than by the thought of gaining something of equal value.

This book reads like a modernized version of The Elements of Style, and provides very specific advice on how to improve your writing both technically and artistically. Surprisingly fun to read as well.

The secret of writing is so strip every sentence to its cleanest components. Every word that serves no function, every long word that could be short, every adverb that carries the same meaning as the verb, every passive construction that leaves the reader unsure of who is doing what.

If what you write is ornate, pompous, or fuzzy, that’s how you’ll be perceived. Be yourself when you write. You will stand out as a real person among the robots.

I wouldn’t say this was a fun read but I use what I learned in this book almost every day at work. Understanding how to setup and leverage analytics is so important for digital marketing that I don’t know how I got by before reading this.

Leading metrics give you a predictive understanding of the future; lagging metrics explain the past. Leading metrics are better because you still have time to act on them — the horse hasn’t left the barn yet.

Don’t just look at the “obvious” flaws of the incumbents (like an outdated design) and assume that’s what needs fixing. You’ll have to dig far deeper in order to find the real customer pain points and make sure you address them quickly and successfully.

I read this on a plane to Europe where I would spend the next 4 months, and I thought about it a lot while there. There is a lot of expectation (and even pressure) to have the most fun possible while traveling. This book looks at why it doesn’t always live up to expectations, and what to do about it.

It is easy for us to forget ourselves when we contemplate pictorial and verbal descriptions of places. At home, as my eyes had panned over photographs of Barbados, there were no reminders that those eyes were intimately tied to a body and mind that would travel with me wherever I went and that might, over time, assert their presence in ways that would threaten or even negate the purpose of what the eyes had come there to see.

Although the title makes it sound like something you’d buy from an infomercial, the Four-Hour Work Week is probably the book that really got me into reading non-fiction in the first place. So much quality advice, but it also serves as an intro to Tim Ferriss’ blog and podcast, which have some of the best content I’ve found online. My close friends can attest to how obsessed I am with Tim Ferriss.

Focus on being productive instead of busy.

The fishing is best where the fewest go and the collective insecurity of the world makes it easy for people to hit home runs while everyone is aiming for base hits.

I really think everyone should read this book at least once in their lives. The concepts are so simple but make such a big difference in the way you interact with people. There’s a reason it’s been popular for 75+ years.

You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.

Any fool can criticize, complain, and condemn—and most fools do. But it takes character and self-control to be understanding and forgiving.

I’ve used the lessons from this book a lot when building Movekit. Although some of the details are dated, the core lessons are still very relevant today. I recommend this one a lot to friends who haven’t gone through business school and who want to start a business.

The Fatal Assumption: if you understand the technical work of a business, you understand a business that does that technical work

Every extraordinary business knows that when you intentionally build your business around the skills of ordinary people, you will be forced to ask the difficult questions about how to produce a result without the extraordinary ones.

This book documents the rise of Zappos with a very personal perspective from the founder/CEO. Although it has a lot of lessons related to building a business, the biggest takeaway I got from this book is just how much grit, passion and luck it takes to make a business succeed.

We must all learn not only to not fear change, but to embrace it enthusiastically and, perhaps even more important, encourage and drive it.

My advice is to stop trying to “network” in the traditional business sense, and instead just try to build up the number and depth of your friendships, where the friendship itself is its own reward.

The cover/title make it look cheesy, but I’ve learned a lot from this book. As a chess master/Tai Chi world champion, Josh Waitzkin outlines the techniques and processes he used to become world-class at two very different skills.

There will be nothing learned from any challenge in which we don’t try our hardest. Growth comes at the point of resistance.

Use your passion to your advantage. The best competitors are so far beyond shakable that opponents, instead of playing mental games, cower for fear of inspiring them. 

Very good advice on making career decisions and building valuable skills. Focuses on the idea that 20-somethings should build valuable skills that will allow them to get the jobs they want, rather than blindly doing things to “follow your passion”.

The craftsman mindset focuses on what you can offer the world. The passion mindset focuses on what the world can offer you.

Great work is rare and valuable. If you want something that’s both rare and valuable, you need something rare and valuable to offer in return.

I picked up this book shortly after starting my work with Busbud to make me more confident stepping into partnership negotiations. It serves as a really good intro to negotiation, the biggest takeaway being that a good negotiation is collaborative more than it is adversarial.

Focus on interests, not positions: behind opposed positions lie shared interests.

Hard on the problem, soft on the people.