The Alchemy of Us – Ainissa Ramirez

The Alchemy of Us – by Ainissa Ramirez
Recommendation: 8/10. Date read: 12/22/20.

Details eight inventions—clocks, steel rails, copper communication cables, photographic film, light bulbs, hard disks, scientific labware, and silicon chips—and ties together not only how the invention came about, but how each invention came to shape humanity and culture. It’s an interesting examination of how technology is both a reflection of the environment it was born in and how it can alter the ways we think about and interact with the world for generations. Ramirez breathes life into each invention with stories from interesting figures throughout history—if you enjoy Bill Bryson, you’ll enjoy this. It’s also a sobering reminder of ethical considerations and responsibilities that those building technology have in our society.

See my notes below or Amazon for details and reviews.

My Notes:

Technology shapes us for generations:
Prose was shortened by the telegraph—removed all unnecessary words avoided flowery language and adjectives. Shaped American English. At a telegrapher’s office when news broke, there was a 15-minute limit and messages had to be brief (you were also charged per word). Led to code language in newsrooms (POTUS, SCOTUS, OK). 

Technology reflects biases of the time:
Early film was only developed to properly capture the characteristics and features of white individuals. Pictures of blacks were always underexposed and lost features of their faces/turned them into ink blots. 

“Technologies we make are not innocuous and their use is not always for the greater good. Technologies, such as photographic film, also capture the issues and beliefs and values of the times.” AR

“These devices capture the biases that exist in our world and, in turn, speak to whom a culture values. As our technologies become more pervasive in our lives, whom they were built for and optimized for will be an important discussion.” AR

Depth:
“If we were to read a book, we would be fully submerged in the details and nuance of another world and swim in the deep end. The internet, however, is a worldwide wading pool. We slosh in the superficial because we have reached a critical point for what our brains can hold.” AR

Creativity:
“Creativity is not just the warehousing of ideas, but a process of giving the brain time to simmer on these ideas. Creativity requires preparation, but it also needs incubation.” AR

Creativity requires you to be exposed to and absorb the world. But it also requires time alone so you’re able to achieve a state of relaxed concentration and give yourself the cycles to examine and reassemble the fragments in your own way. 

The way most use the internet hinders deep thinking: “Our hunting and gathering minds exist in an age where there is nothing to physically hunt or gather, so our brains get trapped in the cycle of hunting and gathering ‘follows’ and ‘likes’ on social media.”

Digital Minimalism – Cal Newport

Digital Minimalism – by Cal Newport
Recommendation 6/10. Date read: 12/3/20.

I read this because I needed a reminder to check myself and eliminate distractions. Newport emphasizes the principles of digital minimalism—mainly cutting back on incessant stimulation—including why clutter is costly, how important it is to optimize fewer things, and how intentionality adds meaning. Really it’s a book about thoughtfulness and being present. It could have been an essay, rather than a book. But helpful nonetheless.

See my notes below or Amazon for details and reviews.

My Notes:

Principles of Digital Minimalism:

  • Clutter is costly

  • Optimization is important (think carefully about how)

  • Intentionality is satisfying (adds meaning)

Be Thoughtful:
“Part of what makes this philosophy so effective is that the very act of being selective about your tools will bring you satisfaction, typically much more than what is lost from the tools you decide to avoid.” CN

Solitude:
“Conversation enriches the understanding, but solitude is the school of genius.” Edward Gibbon

Cites Descartes, Newton, Locke, Pascal, Spinoza, Kant, Leibniz, Schopenhauer, Nietzsche, Kierkegaard, and Wittgenstein as examples of men who never had families or fostered close personal ties, yet still managed to lead remarkable lives.

The Almanack of Naval Ravikant – Eric Jorgenson

The Almanack of Naval Ravikant – by Eric Jorgenson
Recommendation: 9/10. Date read: 11/6/20.

A collection of wisdom from entrepreneur and investor, Naval Ravikant. Jorgenson has consolidated years worth of interviews, podcasts, articles, tweets, and speeches from Ravikant. And he’s assembled the content in a way that’s intuitive, easy to follow, and genuinely helpful in highlighting Naval’s principles for building wealth and long-term happiness. Sections I found particularly insightful focused on Naval’s thoughts on habits, identity, moving with purpose, leveraging meaning as a force multiplier, and the importance of building specific knowledge.

See my notes below or Amazon for details and reviews.

My Notes:

Move with purpose:
Step one, you must know what you’re working towards or you’ll never get there: “Yes, hard work matters, and you can’t skimp on it. But it has to be directed in the right way. If you don’t know yet what you should work on, the most important thing is to figure it out.” Naval Ravikant

“Spend more time making the big decisions. There are basically three really big decisions you make in your early life: where you live, who you’re with, and what you do.” NR

“Choosing what city to live in can almost completely determine the trajectory of your life.” NR

Specific knowledge is key:
Specific knowledge is the key: “Arm yourself with specific knowledge, accountability, and leverage. Specific knowledge is knowledge you cannot be trained for. If society can train you, it can train someone else and replace you. Specific knowledge is found by pursuing your genuine curiosity and passion rather than whatever is hot right now. Build specific knowledge will feel like play to you but will look like work to others. When specific knowledge is taught, it’s through apprenticeships, not schools. Specific knowledge is often highly technical or creative.” NR

Meaning is a force multiplier:
“If you’re not 100 percent into it, somebody else who is 100 percent into it will outperform you. And they won’t just outperform you by a little bit—they’ll outperform you by a lot.” NR

“The way to get out of the competition trap is to be authentic, to find the thing you know how to do better than anybody. You know how to do it better because you love it, and no one can compete with you.” NR

“No one in the world is going to beat you at being you.” NR

“I’m always ‘working.’ It looks like work to others, but it feels like play to me. And that’s how I know no one can compete with me on it. Because I’m just playing, for sixteen hours a day. If others want to compete with me, they’re going to work, and they’re going to lose because they’re not going to do it for sixteen hours a day, seven days a week.” NR

“Look at the kids who are born rich—they have no meaning to their lives.” NR

Ethics:
“Intentions don’t matter. Actions do. That’s why being ethical is hard.” NR

Patience:
“Great people have great outcomes. You just have to be patient.” NR

“Your real resume is just a catalog of all your suffering…the sacrifices you made, the hard things you did.” NR

Simplicity:
“‘Clear thinker’ is a better compliment than ‘smart.’” NR

“When it comes to medicine and nutrition, subtract before you add.” NR

Habits:
“You absolutely need habits to function. You cannot solve every problem in life as if it is the first time it’s thrown at you.” NR

“It’s really important to be able to uncondition yourself, to be able to take your habits apart and say, ‘Okay, this is a habit I probably picked up when I was a toddler trying to get my parent’s attention. Now I’ve reinforced it and reinforced it, and I call it a part of my identity. Does it still serve me?’” NR

“The genuine love for reading itself, when cultivated, is a superpower.” NR

“The number of books completed is a vanity metric. As you know more, you leave more books unfinished. Focus on new concepts with predictive power.” NR

“A calm mind, a fit body, and a house of love. These things cannot be bought. They must be earned.” NR

“Easy choices, hard life. Hard choices, easy life.” Jerzy Gregorek

Identity:
Danger of ideologies: “Any belief you took in a package (ex. Democrat, Catholic, American) is suspect and should be re-evaluated from base principles.” NR

Allow yourself to evolve: “Facebook redesigns. Twitter redesigns. Personalities, careers, and teams also need redesigns. There are no permanent solutions in a dynamic system.” NR

“The fundamental delusion: There is something out there that will make me happy and fulfilled forever.” NR

Sustainability: “Don’t hang around people who constantly engage in conflict. I’m not interested in anything unsustainable or even hard to sustain, including difficult relationships.” NR

Impermanence: “Everything is more beautiful because we’re doomed. You will never be lovelier than you are now, and we will never be here again.” Homer, The Iliad

The Psychology of Money – Morgan Housel

The Psychology of Money – by Morgan Housel
Recommendation: 8/10. Date read: 10/27/20.

Wonderful read from one of the best writers in personal finance and investing. Housel breaks the book up into 19 short stories on how we think about money and the role it plays in our lives. He hits on the usual themes of wealth, greed, and happiness. And he dives deeper into exploring the importance of perspective, the role of luck, how we define success, coming to terms with the fact that wealth is what’s hidden, and why it’s important to embrace the reality of change as we look ahead in our lives.

See my notes below or Amazon for details and reviews.

My Notes:

Perspective:
“We all think we know how the world works. But we’ve all only experienced a tiny sliver of it.” MH

Role of luck:
“But realize that not all success is due to hard work, and not all poverty is due to laziness. Keep this in mind when judging people, including yourself.” MH

Success:
“Success is a lousy teacher. It seduces smart people into thinking they can’t lose.” Bill Gates

In victory learn when to stop: “The hardest financial skill is getting the goalpost to stop moving.” MH

Align yourself with situations which have high upside, limited downside and even if you’re wrong half the time, you can still make a fortune: “It’s not whether you’re right or wrong that’s important, but how much money you make when you’re right and how much you lose when you’re wrong.” George Soros

“If respect and admiration are your goal, be careful how you seek it. Humility, kindness, and empathy will bring you far more respect than horsepower ever will.” MH

Wealth is hidden:
“Someone driving a $100,000 car might be wealthy. But the only data point you have about their wealth is that they have $100,00 less than they did before they bought the car.” MH

“The world is filled with people who look modest but are actually wealthy and people who look rich who live at the razor’s edge of insolvency.” MH

“Savings can be created by spending less. You can spend less if you desire less. And you will desire less if you care less about what others think of you.” MH

Accept the reality of change:
Humans change their minds. If you don’t allow yourself to grow, you’re attempting to stay frozen in time. 

“Some of the most miserable workers I’ve met are people who stay loyal to a career only because it’s the field they picked when deciding on a college major at age 18. When you accept the End of History Illusion, you realize that the odds of picking a job when you’re not old enough to drink that you will still enjoy when you’re old enough to qualify for Social Security are low.” MH

The End of History Illusion: tendency for people to be aware of how much they’ve changed in past but underestimate how much they will change (personalities, desires, goals) in the future.

Goal is independence:
“I did not intend to get rich. I just wanted to get independent.” Charlie Munger

Lessons in Stoicism – John Sellars

Lessons in Stoicism – by John Sellars
Recommendation: 8/10. Date read: 10/9/20.

Short guide on Stoicism that can serve either as a good refresher for those familiar with the philosophy or an easy entry point for those looking for a lightweight introduction. Emphasizes living thoughtfully and hits on all the key concepts inherent to stoicism in less than 100 pages—emotion, judgement, adversity, nature, control, and impermanence.

See my notes below or Amazon for details and reviews.

My Notes:

Judgements:
Focus attention on things within our control, forget about those you can’t control. This requires directing all your attention to your judgements. If you stop observing these or relax for even an instant, you run risk of falling into old habits and compromising your peace of mind.

“No thought is wasted on what others may say or think of him or practice against him; two things alone suffice him, justice in his daily dealings and contentment with all fate’s apportioning.” Marcus Aurelius

Anger:
“Seneca likens being angry to having been thrown off the top of a building and hurtling towards the ground, completely out of control. Once anger takes over, it compromises the whole mind.” JS

“Anger, like all emotions, is the product of a judgement made in the mind.” JS

Adversity:
From Seneca: Adversity falls hardest on those who don’t expect it. But it’s much easier to cope with for those prepared for it.

First Break All the Rules – Gallup Press

First, Break All the Rules – by Gallup Press
Recommendation: 7/10. Date read: 10/3/20.

A solid introduction to management and how to better develop your team. I found it particularly useful as someone who is currently trying to build this skill and help others grow in their careers. The book centers on four key elements: 1) When selecting someone for a role, select for talent. Not simply experience, intelligence, or determination. Gallup emphasizes, “As a manager, your job is not to teach people talent. Your job is to help them earn the accolade ‘talented’ by matching their talent to the role.” 2) When setting expectations, define the right outcomes, don’t prescribe the right steps. 3) When motivating someone, focus on their strengths, not their weaknesses. 4) When developing someone, help them find the right fit, not blindly moving them up to the next rung. Basic, but fundamental concepts that are worth digging into.

See my notes below or Amazon for details and reviews.

My Notes:

The focus of great managers:

  • I know what is expected of me

  • I have the materials and equipment I need to do my work right

  • At work, I have the opportunity to do what I do best every day

  • In the last seven days, I have received recognition or praise for doing good work

  • My supervisor, or someone at work, seems to care about me as a person

  • There is someone at work who encourages my development

Select a person, set expectations, motivate the person and develop the person:

  • When selecting someone, select for talent (not simply experience, intelligence, or determination).

  • When setting expectations, define the right outcomes (not the right steps).

  • When motivating someone, focus on strengths (not weaknesses).

  • When developing someone, help them find the right fit (not the next rung).

Talent:
“A love of precision is not a skill. Nor is it a knowledge. It is a talent. If you don’t possess it, you will never excel as an accountant. If someone does not have this talent as part of his filter, there is very little a manager can do to inject it.” Alex: talent in product is a love to create/build.

Three kinds of talent: striving = why of a person, thinking = how/decision making, relating = who of person. 

The talent alone isn’t special, you must match it with the right role. For example the relating talent of empathy with nursing. 

“As a manager, your job is not to teach people talent. Your job is to help them earn the accolade ‘talented’ by matching their talent to the role.”

“A broker with lots of desire and focus is not necessarily a better broker than one with lots of achiever and discipline. But she would certainly fit better in the entrepreneurial company, just as the broker blessed with achiever and discipline would be better cast in the more structured company.”

Focus on strengths:
“You succeed by finding ways to capitalize on who you are, not by trying to fix who you aren’t. If you are blunt in one or two important areas, try to find a partner whose peaks match your valleys. Balance by this partner, you are then free to hone your talent to a sharper point.”

Interviewing:
Past behavior is a good predictor of future behavior, but only give credit to the person’s top of mind response. If the behavior is consistent, a response will come to mind will a single prompt. If they need two or three probes to describe an example, they likely haven’t faced that scenario with any sort of regular frequency.

A person’s source of satisfaction are clues to his talent. Ask what their greatest personal satisfaction is, what kind of situations give them strength, what they find fulfilling. 

Performance Management:
Foundation = simplicity, frequent interaction, focus on the future, and self-tracking.

This Is Water – David Foster Wallace

This Is Water – by David Foster Wallace
Recommendation: 7/10. Date read: 8/30/20.

Essay from David Foster Wallace inspired by a commencement speech he gave at Kenyon College in 2005. Short read but thought provoking as he examines meaning, awareness, discipline, and learning how to think. You can likely find the transcript online, though I enjoyed having a copy I could mark up of my own.

See my notes below or Amazon for details and reviews.

My Notes:

“As if how we construct meaning were not actually a matter of personal, intentional choice, of conscious decision.”

“There is no such thing as not worshipping. The only choice we get is what to worship.”

Learning how to think: “It means being conscious and aware enough to choose what you pay attention to and to choose how you construct meaning from experience. Because if you cannot or will not exercise this kind of choice in adult life, you will be totally hosed.” 

“Look, the insidious thing about these forms of worship is not that they’re evil or sinful; it is that they are unconscious. They are default settings.”

“The really important kind of freedom involves attention, and awareness, and discipline, and effort, and being able to truly care about other people and to sacrifice for them, over and over, in myriad petty little unsexy ways, every day.”

How Innovation Works – Matt Ridley

How Innovation Works – by Matt Ridley
Recommendation: 8/10. Date read: 9/17/20.

Examines the role of innovation—an often misunderstood concept—in the modern age. He discusses the environmental conditions that promote innovation, how it differs from “invention,” and how our idea of a single moment of brilliance as the key to technological advances is flat out wrong. For those in technology who are on the ground floor doing the work, the message will be refreshing. Ridley emphasizes how iteration is the key to innovation—you have to get as many reps in as possible to turn an invention into something that’s both practical and affordable for widespread use. The story of innovation is one of incremental improvements and the freedom to exchange, experiment, imagine, invest, and fail.

See my notes below or Amazon for details and reviews.

My Notes:

Simultaneous Invention:
“Again and again, simultaneous invention marks the progress of technology as if there is something ripe about the moment. It does not necessarily imply plagiarism. In this case, the combination of better metalworking, more interest in mining and a scientific fascination with vacuums had come together in north-western Europe to make a rudimentary steam engine almost inevitable.”

“It was impossible for search engines not to be invented in the 1990s, and impossible for light bulbs not to be invented in the 1870s. They were inevitable. The state of the underlying technologies had reached the point where they would be bound to appear, no matter who was around.”

Brilliance vs. Hard Work:
“Vanity: people prefer to be thought brilliant rather than mere hard-working.”

Ingredients of Innovation:
Tolerance of error is critical: “Innovation is itself a product, the manufacturing of which is a team effort requiring trial and error.”

“The main ingredient in the secret sauce that leads to innovation is freedom. Freedom to exchange, experiment, imagine, invest and fail; freedom from the expropriation or restriction by chiefs, priests and thieves.” 

Revolution vs. Evolution:
Gradual improvements = key to iteration. “The history of turbines and electricity is profoundly gradual not marked by any sudden step changes…It was an evolution, not a series of revolutions. The key inventions along the way each built upon the previous one and made the next one possible.”

Innovation is the “product of incremental tinkering and trial and error by several people, not of brilliant leaps if imagination by a genius.” 

“Innovation is not an individual phenomenon, but a collective, incremental and messy network phenomenon.”

“The idea of a single moment of inspiration, of the apple landing on young Isaac Newton’s head, stirs the soul, even if it turns out to be apocryphal. In contrast, the idea that innovation occurs in fits and starts, with one person adapting a concept already in use and another figuring out how to make a profit from it, has little appeal.” Marc Levinson

“There is no day when you can say: computers did not exist the day before and did the day after, any more than you could say that one ape-person was an ape and her daughter was a person.”

The Arch of Innovation:
“The story of the internal-combustion engine displays the usual feature of an innovation: a long and deep prehistory characterized by failure; a shorter period marked by an improvement in affordability characterized by simultaneous patenting and rivalries; and a subsequent story of evolutionary improvement by trial and error.” 

“The simplest ingredients—which had always been there—can produce the most improbable outcome if combined in ingenious ways…just through the rearrangement of molecules and atoms in patterns far from thermodynamic equilibrium.” 

Opposition to Innovation:
“Big companies are bad at innovating, because they are too bureaucratic, have too big a vested interest in the status quo and stop paying attention to the interests, actual and potential, of their customers. Thus for innovation to flourish it is vital to have an economy that encourages or at least allows outsiders, challengers and disruptors to get a foothold. This means openness to competition, which historically is a surprisingly rare feature of most societies.”

Other characteristics that are in opposition to innovation: an appeal to safety, a degree of self-interest among vested interests, paranoia among the powerful.

American Nations - Colin Woodard

American Nations: A History of the Eleven Rival Regional Cultures of North America – by Colin Woodard
Recommendation: 8/10. Date read: 7/28/20.

Challenges the perspective that the Americans are living through a uniquely divisive moment in time. Instead, Woodard suggests Americans have been deeply divided since the days of Jamestown and Plymouth. The original North American colonies were settled by people from distinct regions with unique religious, political, and ethnographic characteristics. Since the colonial period, the eleven rival regional cultures in North America have regarded one another as competitors for land, settlers, and capital. Woodard offers insight into why specific regions hold a particular set of beliefs, the power of early influence, and the dangers in blindly adopting ideologies. It’s a powerful book and source of perspective to help you navigate current events without getting trapped into a tribe mentality.

See my notes below or Amazon for details and reviews.


My Notes:

Illusion of Unity:
Americans have been deeply divided for centuries—original North American colonies were settlement by people from British Islands, France, the Netherlands, Spain. Each with distinct religious, political, and ethnographic characteristics. Saw the other as competition for land, settlers, and capital. 

“American’s most essential and abiding division are not between red and blue states…the United States is a federation comprised of the whole or part of eleven regional nations, so of which truly do not see eye to eye with one another.” CW

The 11 rival regional cultures: Yankeedom, Tidewater, Greater Appalachia, The Deep South, New Netherland, New France, The Midlands, First Nation, El Norte, The Far West, The Left Coast.

These regional cultures have been fundamental in shaping the way we think, as well as North American history, politics, and governance.

Power of Early Influence:
“Thus, in terms of lasting impact, the activities of a few hundred, or even a few score, initial colonizers can mean much more for the cultural geography of a place than the contributions of tens of thousands of new immigrants of a few generations later.” Wilbur Zelinsky

Goals in each region:
Early Yankeedom and Midlands—building a religious utopia.

New Netherland—individual freedoms of conscience, speech, religion, assembly.

New France—complex network of Indian alliances.

Chesapeake colonies (Tidewater)—recreate the genteel manor life of rural England in the New World.

Greater Appalachia—warrior culture, self-reliant, suspicious of outside authority, valued individual liberty and personal honor above all else.

Tidewater:
“Tidewater’s semifeudal model required a vast and permanent underclass to play the role of serfs, on whose toil the entire system depended. But from the 1670s onward, the gentry had an increasingly difficult time finding enough poor Englishmen willing to take on this role.” Slave traders offered a solution. Slave caste grew from 10% of Tidewater’s population in 1700 to 40% in 1760. 

“The south was not founded to create slavery; slavery was recruited to perpetuate the South.”

In the early years, Tidewater was settled largely by young, unskilled male servants.

Yankeedom:
Central myth of American history is that founders of Yankeedom were champions of religious freedom, fleeing religious persecution. Only true of a few hundred pilgrims (English Calvinists) in Cape Cod in 1620. Vast majority were Puritans who “forbade anyone to settle in their colony who failed to pass a test of religious conformity.”

“Early Yankeedom was less tolerant of moral or religious deviance than the England its settlers had left behind.”

Expectation that everyone should read the Bible required everyone to be literate. This led to a proliferation of schoolhouses and requirement that all children be sent to school. 

New Englanders always intended to rule themselves so they were never beholden to nobles or corporations. 

New England’s colonists were skilled craftsmen, lawyer, doctors. Came over as families. Gave them more of a normal distribution of age and gender ratios than other regions. Allowed their population to grow faster. 1660, Yankeedom population was around 60k (twice Tidewater). 

Deep South:
“From the outset, Deep Southern culture was based on radical disparities in wealth and power, with a tiny elite commanding total obedience and enforcing it with state-sponsored terror.” CW

“Most of the other nations were societies with slaves, not slave societies per se. Only in Tidewater and the Deep South did slavery become the central organizing principle of the economy and culture. “ CW

Civil War: If not for Deep Southerners attacks on federal post offices, mints, arsenals, and military bases in 1861, they might have negotiated a peaceful secession. Prior to South Carolina’s militia assault on Fort Sumter, Yankeedom lacked allies in its desire for force. This proved to be the catalyst that mobilized other regions who were previously disinterested coming to the aid of the North. 

Greater Appalachia:
Embraced a self-sufficient way of life, living off the land and moving every few years. Life in Britain taught them not to invest too much time and wealth in fixed property which was easily destroyed in time of war. 

“When they did need cash, they distilled corn into a more portable, storable, and valuable product: whiskey, which would remain the de facto currency of Appalachia for the next two centuries.” CW

“‘Hoosier’—a Southern slang term for a frontier hick—was adopted as a badge of honor by the Appalachian people of Indiana. 

A Common Struggle:
What brought these rival cultures was an effort to preserve their respective, culture, character, and power structure. “They were joined in a temporary partnership against a common thread: the British establishment’s ham-fisted attempt to assimilate them into a homogenous empire central controlled from London.” 

By the time England tried to impose uniformity and centralization of power, many of the regions were several generations old and had their own traditions, values, and interests. 

Articles of Confederation created more of a political entity (like the EU) that was a voluntary alliance of sovereign states. Not a nation state.

The Left Coast:
Gold rush, 1848: “In what was one of the largest spontaneous migrations in human history to that point, 300,000 arrived in California in just five years, increasing the new American territory’s non-Indian population twentyfold. Within twenty-four months San Francisco grew from a village of 800 to a city of 20,000.”

WW2:
Pearl Harbor united the regions together like never before. Borderlanders fought to avenge attack, Tidewater and Depp South wished to uphold national honor and defend Anglo-Norman brethren, Midlanders backed the war as a struggle against military despotism, Yankees/New Netherlanders/Left Coasters emphasize the anti-authoritarian aspect of the struggle. El Norte and the Far West embraced war which brought resources and investment to their long-neglected regions.

Hitler and Hirohito did more for the development of the Far West and El Norte than any other agent in their histories. Previously they were exploited as internal colonies. But during war were given industrial bases, shipyards, naval bases, aircraft plants, steel mills, nuclear weapons labs, test sites. 

Modern Day:
Nations of the Dixie bloc create policies to ensure they remain low-wage resource colonies controlled by a one-party political system which serves interests of a wealth elite. To keep wages low, make it difficult to organize unions. Taxes kept too low to support public schools, urban planning, land-use zoning. 

Foreign policy: Yankees = anti-interventionist, anti-imperial, idealistic, intellectual, seek foreign policies that will civilize the world, so they dominate Foreign Affairs Committee. Dixie-bloc = martial and honor bound, aim to dominate and focus on power, so they dominate the Armed Services Committee. 

Divergent approaches to economic development, tax policy, and social spending only increase tensions between the cultural blocs. 

A Wealth of Common Sense – Ben Carlson

A Wealth of Common Sense – by Ben Carlson
Recommendation: 9/10. Date read: 7/21/20.

One of the best investment books that I’ve read in years. Carlson is one of my favorite minds in finance and he also hosts one of my favorite podcasts. In this book he emphasizes how simplicity beats complexity in most investment plans. Many of the complex investment strategies in finance only serve to create the illusion of intelligence and control. Carlson discusses the value of long-term thinking, market myths, diversification, and the importance of self-awareness. As he explains, “Less is always more and trying to implement a more interesting or clever portfolio strategy is akin to threading the needle. Sure, it can work, but trying harder and increasing the number of decisions you make only increases the odds that you’ll make a mistake.” If I had to gift a single book on investing for someone to start off with or to help remind you to maintain perspective and patience in your investments, this would be the one.

See my notes below or Amazon for details and reviews.

My Notes:

Perspective:
“How you frame the world around you determines how certain events will affect your reactions to outside factors than can impact your financial decisions.” BC

Perspective allows you to ignore headlines, gurus, and acting on impulsive emotions that hinder good decision-making. 

Reduce external pressure: “Investing doesn’t have to be about beating others or beating the market. It’s about not beating yourself.” BC

Patience:
“Speculation is an effort, probably unsuccessful to turn a little money into a lot. Investment is an effort, which should be successful, to prevent a lot of money from becoming a little.” Fred Schwed

If you want to be a successful investor, learn how to harness the power of long-term thinking, cut down on unforced errors by reducing complexity), and find the patience to allow compound interest to run its course.

One of the biggest advantages individuals have over professional investors is the ability to be patient. There’s no one to impress and no one’s judging you against your peers. 

“Having the correct temperament is far more important than intellect over time.” BC

“Charlie and I always knew we would become very wealthy, but we weren’t in a hurry. Even if you’re a slightly above average investor who spends less than you earn, over a lifetime you cannot help but get very wealthy—if you’re patient.” Warren Buffett

Emotions drive the stock market over days, weeks, years. Fundamentals drive the stock market over decades. 

Complexity versus simplicity:
“Less is always more and trying to implement a more interesting or clever portfolio strategy is akin to threading the needle. Sure, it can work, but trying harder and increasing the number of decisions you make only increases the odds that you’ll make a mistake.” BC

Best answer to a complex system is not necessarily a complex response. In portfolio management, best method is based on simplicity, transparency, and reduced level of activities. 

Fragmentation benefits players in archaic industries who seek sophistication to justify their existence (see Nassim Taleb, Antifragile). Similar concept applies to the real estate industry. 

“The interesting thing about very intelligent and successful people is that they’re usually the ones who have figured out that making things simple is the correct path to success. Because they understand how things work, they are able to appreciate and utilize simplicity.” BC

Self-awareness:
“When ‘dumb’ money acknowledges its limitations, it ceases to be dumb.” Warren Buffett

“If you can get good at destroying your own wrong ideas, that is a great gift.” Charlie Munger

Also applies to product: “Most people will get much more out of destroying their own wrong ideas than trying to come up with new ones all the time.” BC

“There are many ways to make money, but when it really comes down to it, the easiest way to lose money is because of psychological and behavioral issues.” BC

Strategy:
“Low-cost passive strategies suit the overwhelming number of individual and institutional investors without the time, resources, and ability to make high-quality decisions.” David Swensen

The point of dollar cost averaging is admitting you don’t have the ability or emotional control to time the market. 

Low-quality companies can become bargains. High-quality companies can become overpriced. Great companies don’t always make for great stocks. Terrible companies can become solid investments at the right price point. Value stocks outperform the market (historically) between 2-5%. 

Chances of picking an individual winning stock is small while your odds of picking a loser are huge. Survivor bias leads us to think otherwise. 

“Instead of concentrating on the central issue of creating sensible long-term asset allocation targets, investors too frequently focus on the unproductive divisions of security selection and market timing.” David Swensen

Asset allocation accounts for 90% of a portfolio’s long-term gains. Market timing and ability to select individual securities account for only 10%. 

Diversification allows you to hedge against ‘what if I’m wrong?’

“Remember, there is nothing special about index funds. The biggest advantage they have over the majority of active mutual funds is the fact that they are disciplined.” BC

“Have a plan. Follow the plan, and you’ll be surprised how successful you can be. Most people don’t have a plan. That’s why it’s easy to beat most folks.” Bear Bryant

Tax inefficient assets (bonds, REITs, high dividend-paying stocks) should go in tax-deferred retirement accounts. Stock index funds and ETFs are more tax efficient and make more sense to include in taxable accounts. 

Conscientiousness:
Great investors are conscientious: “Conscientious-minded people tend to save more money because they don’t make impulse purchases or spend too much money on things they don’t need. In fact, those who exhibit this trait tend to accumulate more wealth than less conscientious people, even after accounting for things like education, income, and cognitive abilities.” BC

“Investment philosophy is really about temperament, not raw intellect. In fact, proper temperament will beat high IQ all day.” Michael Mauboussin

Top priority is to become a diligent saver. Save more than you make. 

Factors that lead to poor decision making:

  1. Complex problem

  2. Incomplete information or information changes

  3. Goals change or compete with one another

  4. High stress or high stakes

  5. High interaction with others to make a decision

Timing the market:
Peter Lynch studied 30-year period from 1965 to 1995…

  • If you invested every single year at the lowest day in the market, your return would have been 11.7% annually

  • If you invested every single year at the highest day in the market, your return would have been 10.6%

  • If you invested every single year on the first day of the year, your return would have been 11.0%. 

  • Dollar cost averaging with a long time horizon is much less stressful and generates solid returns.

Generally stocks are up 3 out of every 4 years. In five years, it jumps to 90%. In 20 years, US stocks have shown positive returns of all 20-year periods in history.

“Investment wisdom begins with the realization that long-term returns are the only ones that matter.” William Bernstein

Passages – Gail Sheehy

Passages – by Gail Sheehy
Date read: 7/3/20. Recommendation: 8/10

Some might say this book is a bit outdated (1976), but as much as we might like to think we’re different than previous generations, our behaviors and thought patterns remain unchanged. Passages is organized around the stages of life. I found it insightful to reflect upon decades of life that I’ve already worked my way through and look ahead to the challenges many have faced in the ones ahead. Sheehy draws upon real stories to breathe life into each decade and highlights key lessons in personal development, finding yourself, relationships, parenting, and allowing yourself to evolve. As she emphasizes, “The work of adult life is not easy…each step presents not only new tasks of development but requires a letting go of the techniques that worked before.”

See my notes below or Amazon for details and reviews.

My Notes:

Development:
“The work of adult life is not easy…each step presents not only new tasks of development but requires a letting go of the techniques that worked before.” GS

“We must be willing to change chairs if we want to grow. There is no permanent compatibility between a chair and a person.” GS

False fear in 20s is that choices are irrevocable. Two impulses at work during this period…Merger Self is to create safe structure and make strong commitments without much self-examination, taken to an extreme creates a locked-in feeling. Seeker Self favors urge to explore and experiment, limiting commitments and structure, taken to an extreme leads to flaky mindset bouncing from one job or relationship to the next. Balance determines how you exit your 20s. 

“Resolving the issues of one passage does not insulate us forever. There will be other tricky channels ahead, and we learn by moving through them. If we pretend the crises of development don’t exist, not only will they rise up later and hit with a greater wallop, but in the meantime we don’t grow. We’re captives. If the growth work has been done on the developmental tasks of one passage, it bodes well for meeting the challenges of the next one.”

Timing your leaps and the sigmoid curve: 
“Events that demand a leap of action before we’re ready often have the happy effect of boosting us on to the next stage of development in spite of ourselves.”

“Working toward a degree is something young people already know how to do. It postpones having to prove oneself in the bigger, bullying arena.” GS

Finding yourself:
Prioritizing, searching for, and finding a work experience that resonates with you is the first step towards resolving conflicts of dependency and creating an independent identity.

“Somewhere along the line of development we discover what we really are, and then we make our real decision for which we are responsible. Make that decision primarily for yourself because you can never really live anyone else’s life, not even your own child’s. The influence you exert is through your own life and what you become yourself.” Eleanor Roosevelt

Parenting: 
The best parents don’t shield us from problems of security, acceptance, control, jealousy, rivalry. For a child to truly know themselves, they must come to terms with all these parts. 

Relationships:
“Oh, what tears and rejection await the girl who imbues her first delicate match with fantasies of permanence, expecting that he at this gelatinous stage will fit with her in a finished puzzle for all the days” GS

Allow yourself to evolve: 
Those who reach mid-life (50s) and are still trying to find meaning in the same place as previous decades, doing the same things, end up stuck through their attempts to cling to the familiar. Your interests, your sense of meaning, and your own authenticity should evolve through each chapter of life. 

A deeper investment in the choices of your early years makes possible the enrichment of your middle years, and so on. 

Be brave enough to confront each of life’s passages. You can’t skip chapter if you want sustainable personal growth and to develop into the best version of yourself. 

“The willingness to move through each passage is the equivalent to the willingness to live abundantly. If we don’t change, we don’t grow.” GS

“Growth demands a temporary surrender of security. It may mean a giving up of familiar but limiting patterns, safe but unrewarding work, values no longer believed in, relationships that have lost their meaning.” GS

“The power to animate all of life’s seasons is a power that resides within us.” GS

Prisoners of Geography – Tim Marshall

Prisoners of Geography – by Tim Marshall
Date read: 6/3/20. Recommendation: 8/10.

To understand the world—our past, present, and future—we must understand the role that location plays in shaping the strengths and vulnerabilities of different countries. Each chapter tracks a different region, as indicated by the subtitle Ten Maps That Explain Everything About the World. Fascinating read for those who enjoy geography and maps. Marshall gives a compelling introduction to the world of geopolitics and how people, power, ideas, and movements are shaped by their surrounding geography.

See my notes below or Amazon for details and reviews.

My Notes:

To understand the world and our future, we must understand the role of geography:
“The land on which we live has always shaped us. It has shaped the wars, the power, politics, and social development of the peoples that now inhabit nearly every part of the earth.” TM

Russia:
Lack of a warm-water port which allows direct access to the ocean has always placed Russian at a significant disadvantage. Largest Russian port on the Pacific is ice-locked for one third of the year. Only reason they aren’t much weaker is because of natural resources (oil and gas).

China:
To understand China, you must take into account massive cultural differences that value the collective above the individual (what we’re familiar with in the West). 

Unity and economic progress are the top priority, not democratic principles. 

Reason that the massive powers that are China and India haven’t clashed in the past is because the highest mountain range in the world separates the two.

United States:
“For thirty years it has been fashionable to predict the imminent or ongoing decline of the United States. This is as wrong now as it was in the past. The planet’s most successful country is about to become self-sufficient in energy, it remains the preeminent economic power, and it spends more on research and development for its military than the overall military budget of all other NATO countries combined.” TM

Expanding territory in key regions during early development allowed US to achieve status as two-ocean superpower. 

Africa:
Limiting factor is the lack of navigable rivers to connect regions and easily transport goods and ideas over greater distances (unlike the geography of Europe or North America which facilitated this). Rivers in Africa with their rapids and waterfalls make them impossible to use as trade routes. This stunted economic development and hindered large coordinated trade across regions. 

In the modern world, many Africans are still navigating the disaster of the political geography that Europeans made.

Egypt might have become a greater power, as it’s protected by deserts on three sides. But their major flaw was a lack of trees. And without trees you can’t build a strong navy—the key to projecting and sustaining power time and time again on the world stage. 

The Laws of Wealth – Daniel Crosby

The Laws of Wealth – by Daniel Crosby
Date read: 5/19/20. Recommendation: 8/10.

If you’re looking for a book on finance or investing (especially in today’s market), you could do worse than picking this one up. Crosby gives an accessible overview of behavioral finance and offers principles for managing your own investing process and behavior. I always find books like this incredibly insightful and an important reminder that developing greater self-awareness and managing behavioral risk is the best chance you have to avoid falling victim to irrational or emotional financial decisions. Crosby emphasizes that investor behavior—rather than fund selection or market timing—is the best predictor of wealth creation. And patience levels the playing field.

See my notes below or Amazon for details and reviews.

My Notes:

Patience:
“Individuals have to understand that no matter what innovations we see in the financial industry, patience will always be the great equalizer in financial markets. There’s no way to arbitrage good behavior over a long time horizon. In fact, one of the biggest advantages individuals have over the pros is the ability to be patient.” Ben Carlson

What’s within your control?
“The investor’s chief problem—and even his worst enemy—is likely to be himself.” Benjamin Graham

Investor behavior is a better predictor of wealth creation than fund selection or market timing.

“Emotions are the enemy of good investment decisions.” Ben Carlson

“Investors who own their mediocrity are able to rely on rules and systems—they do what works and reap the rewards. Investors mired in a need to be better than average insist on flaunting the rules in favor of their own ideas and pay a steep price for their arrogance.” DC

“Investing isn’t about beating others at their game. It’s about controlling yourself at your own game.” Jason Zweig

Complexity is far easier than simplicity. Simplicity demands discipline, first principles thinking, and a deep understanding of the biases that you might be prone to.

Financial advisors:
Chief benefit to most people is not that of an asset manager, but as a behavioral coach. 

Value investing:
“Paying an appropriate price is the single greatest thing that you can do to ensure appropriate returns and manage risk.” DC

Two ways to profit from variability in stock prices—1) timing the market or 2) pricing. 

“The riskiness of an asset can never be divorced from the price that you pay for it; paying a fair price is the best friend of the risk-averse investor.” DC

“Value investing makes you rich over time, but growth investing can make you rich overnight.” DC

“Value investing requires us to overcome our fundamental tendency to attribute greater quality to things that are more expensively priced. Value investing requires us to sacrifice short-term opportunities at fantastic wealth for longer-term consistency of returns. Being a value investor requires us to ignore the positive stories surrounding glamour stocks.” DC

Avoid expensive stocks. 

Successful investing:
“Successful investing relies heavily on buying socks that have good prospects, but for which investors currently have low expectations.” James O’Shaughnessy

Average investors conduct postmortems to understand what went wrong and leverage those lessons in the future. Create investors conduct pre-mortem to challenge assumptions, anticipate gaps in logic, and make adjustments.

“Indeed, I have found that a large percentage of my winning trades begin with a rehearsal of negative, what-if scenarios in which I mentally invoke my stop strategy. Conversely, I have found that my worst trades begin with an estimate of my potential profits.” Brett Steenbarger

Leadership in Turbulent Times – Doris Kearns Goodwin

Leadership in Turbulent Times – by Doris Kearns Goodwin
Date read: 4/25/20. Recommendation: 10/10.

This was one of the best books, if not the best, that I’ve read in the past twelve months. Goodwin highlights lessons in leadership demonstrated by four US Presidents: Abraham Lincoln, Theodore Roosevelt, Franklin Roosevelt, and Lyndon Johnson. Goodwin explores how each president came from a very different upbringing and the role that played in their leadership style. She also looks at how each man responded to extreme hardship during the bleakest moments of their lives—three of the four emerged from catastrophic turns of fortune with an enlarged capacity for leadership. Each president demonstrated their own unique capacity for transformational, crisis, turnaround, and visionary leadership. Goodwin structures the book in an accessible way that proves to be a great jumping-off point to explore both the lives and the leadership principles that helped guide a few of our best presidents.

See my notes below or Amazon for details and reviews.


My Notes:

Formative Years:
“Privilege can stunt ambition, just as the lack of privilege can fire ambition.” DKG

“Temperament is the great separator.” Richard Neustadt

Lincoln: 
Incredible motivation and willpower to develop every talent to the fullest.

Lincoln’s hallmark: the philosophical and poetic depths of his mind.

Honed a clear and inquisitive mind through hard work. He would rewrite passages that stuck him and keep them in a scrapbook. “I am slow to learn and slow to forget what I have learned.” Lincoln

“While his mind was neither quick nor facile, young Lincoln possessed singular powers of reasoning and comprehension, unflagging curiosity, and a fierce, almost irresistible, compulsion to understand the meaning of what he heard, read, or was taught.” DKG

Formal education ended at the age of nine, after that he had to educate himself. He was voracious reader, scoured the countryside to borrow books and read every volume. 

Of the four presidents in this book, “Only Abraham Lincoln, who had actually endured physical danger and the bitter hardships of wilderness life, never romanticized his family’s past.” DKG

Teddy Roosevelt: 
“His ability to concentrate was such that the house might fall about his head and we would not be diverted.”

Teddy’s hallmark: his scintillating breadth of intelligence. 

Franklin Roosevelt: 
Optimistic spirit and expectation that things would turn out for the best were a testament to the self-confidence he developed during the peacefulness and regularity of his childhood days.

FDR’s hallmark: “An uncommon intuitive capacity and interpersonal intelligence allowed him as a child to read the intentions and desires of his parents, to react appropriately to shifting household moods—gifts that he would nurture and develop in the years ahead. While he did not learn as a felling academic often does—by mastering vast reading material and applying analytical skills—he possessed an incredibly shrewd, complicated, problem-solving intelligence.” DKG

His ability in later years to adapt to changing circumstances also proved vital to his leadership success. Adaptability was forced upon him at the age of eight when his father suffered a heart attack. “The need to navigate the altered dynamic of Springwood required new measures of secrecy, duplicity, and manipulation—qualities that would later prove troubling but were at this juncture benign, designed only to protect a loved one from harm.”

After his father’s heart attack, FDR spent more time in the house (rather than sledding, horseback riding, fishing, which he and his father did daily in his early years). Here he began to build collections of stamps, maps, model ships, etc.

Collecting is a way of ordering a disordered world. It holds a special meaning for children, offering a small corner of the world where the child is in charge, experiencing the “thrill of acquisition.” (Summarizing Walter Benjamin)

Test and learn: “He would fling things agains the wall, seeing if they would stick; if they didn’t, he would acknowledge his mistake and try something else.” DKG

Hobbies and Meditative Space:

  • Lincoln was able to relax with poetry and theater.

  • Teddy was interested in birds, exploration, and the latest novels.

  • FDR spent hours away sailing, playing with stamps, enjoying poker and social chatter.

  • LBJ, in contrast, could never unwind and let go for a few hours.

“Roosevelt’s childhood hobbies (mainly sorting and arranging his stamp collection) would serve in later years as invaluable tools in nourishing his leadership—providing a meditative state, a space which he could turn things over in his mind, the means by which he could relax and replenish his energy.” DKG

Adversity and Growth:
Growth in the face of frustration and extracting wisdom from experience: “Some people lose their bearings; their lives are forever stunted. Others resume their normal behaviors after a period of time. Still others, through reflection and adaptive capacity, are able to transcend their ordeal, armed with a greater resolve and purpose.” DKG

“Each of these three men (Lincoln, Teddy, FDR) emerged from a catastrophic turn of fortune with an enlarged capacity for leadership.” DKG

Lincoln: 
Alive time vs. dead time (see Robert Greene): The half-decade after Lincoln’s unhappy tenure in Congress was anything but a passive time. “It was, on the contrary, and intense period of personal, intellectual, moral and professional growth, for during these years he learned to position himself as a lawyer and leader able to cope with the tremors that were beginning to rack the country.” 

“What fired in Lincoln in this furious and fertile time of self-improvement? The answer lay in his readiness to gaze in the mirror and soberly scrutinize himself.” DKG

“Leave nothing for tomorrow that can be done today.” Lincoln

One of the key’s to Lincoln’s success was his ability to break complex problems into their simplest elements.

Teddy Roosevelt: 
After his wife and mother died just hours apart in 1884, Teddy set off for the North Dakota where he would remain for two years, working on a cattle ranch and learning how heal, grow, and move past the trauma. He’d later regard this as “the most important educational asset” of his entire life. He built grit and cultivated his new identity as “a hybrid of the cultivated easterner and the hard-bitten westerner.” 

Franklin Roosevelt: 
Trial and error was fundamental to his leadership style. “In the Navy Department, he had flung ideas against the wall to see which ones might stick; during the New Deal he would experiment with one program after another, swiftly changing course if the present one proved ineffective.” DKG

Lessons in Leadership:

Lincoln: 
Team of rivals: Unlike James Buchanan who had chosen a cabinet of like-minded men who wouldn’t question his authority, Lincoln actively sought the opposite. “Lincoln created a team of independent, strong-minded men, all of whom were more experienced in public life, better educated, and more celebrated than he. In the top three positions, at the State Department, the Treasury, and the Justice Department, he placed his three chief rivals—William Seward, Salmon Chase, and Edward Bates—each of whom thought he should be president instead of the prairie lawyer from Illinois.” Lincoln did this because he knew the country was in peril and these were the strongest men he knew. 

“Lincoln possessed a deep-rooted integrity and humility combined with an ever-growing confidence in his capacity to lead. Most of all, he brought a mind tempered by failure, a mind able to fashion the appalling suffering ahead into a narrative that would give direction, purpose, and lasting inspiration.” DKG

Control anger: When angry at a colleague, Lincoln would write out a letter with all his frustrations and gripes, then put the letter aside until he calmed down and could review what he had written. The act of talking through his frustrations with himself was always enough and he never sent the vast majority of these. 

Other key transformational leadership lessons from Lincoln:

  • Gather firsthand information, ask questions.

  • Find time and space in which to think.

  • Assume full responsibility for a pivotal decision.

  • Understand the emotional needs of each member of the team.

  • Refuse to let past resentments fester; transcend personal vendettas.

  • Shield colleagues from blame and don’t allow subordinates to take the blame.

Lincoln was a master of combining transactional and transformational leadership. He knew how to combine an appeal to self-interest to influence behavior of others while layering on an inspiring vision so people could also identify with something larger than themselves. 

Franklin Roosevelt: 
Make yourself appear confident in order to become more confident: “The remarkable thing about him (FDR) was his readiness to assume responsibility and his taking that responsibility with a smile.” FDR

Fireside chats: Communicated challenges facing the country by translating stories in a way that could be better understood by himself and the average citizen, rather than in highly specialized language of the legal and banking worlds. Used simple, direct communication and identified the questions people asked themselves so he could answer them. 

“Roosevelt’s gift of communication prove the vital instrument of his success in developing a common mission, clarifying problems, mobilizing action, and earning people’s trust.” DKG

Be open to experiment: “Roosevelt stressed the improvisational, experimental nature of the New Deal.” He was adaptable, willing to shift ground, revise, and accommodate changing circumstances, due to the entirely new problems the country faced.

Bias for action: “Do the very best you can in making up your mind, but once your mind is made up go ahead.” FDR

In victory know when to stop:
Theodore Roosevelt announced he would not run for a third term and instead backed William Howard Taft and set sail for a year-long safari. But when he returned he decided he wanted to challenge Taft for the nomination after all and lost. Later Roosevelt decided to run as a third party candidate and allowed Woodrow Wilson to win the election, hurting the progressive cause he stood for. 

The Practicing Stoic – Ward Farnsworth

The Practicing Stoic – by Ward Farnsworth
Date read: 4/11/20. Recommendation: 9/10.

One of the best modern overviews of Stoicism that I’ve read. Farnsworth sets out to organize the ideas of the Stoic philosophers in a logical manner with foundational principles first, followed by their practical applications. He synthesizes the most important points made by different Stoics about each subject. One thing that makes this book particularly unique and resonated with me was the fact that he sprinkles in parallel ideas from other contemporary thinkers and philosophers, like Montaigne, Samuel Johnson, and Arthur Schopenhauer.

See my notes below or Amazon for details and reviews.

My Notes:

Judgment:
“We react to our judgments and opinions—to our thoughts about things, not to things themselves.” WF

Event > judgment/opinion > reaction. Your job is to begin recognizing the middle step. 

“Men are disturbed not by the things that happen but by their opinions about those things” Epictetus

“It is not what things are objective and in themselves, but what they are for us, in our way of looking at them, that makes us happy or the reverse.” Schopenhauer

“We can choose to have no opinion about a thing and not to be trouble by it; for things themselves have no power of their own to affect our judgments.” Marcus Aurelius

“It takes greatness of mind to judge great matters; otherwise they will seem to have defects that in truth belong to us. In the same way, certain objects that are perfectly straight will, when sunk in the water, appear to the onlooker as bent or broken off. It is not so much what you see but how you see it that matters. When it comes to perceiving reality, our minds are in a fog.” Seneca

“The work of philosophy is to take responsibility for our own thinking, and in doing so to liberate ourselves from the attachments and misjudgments that otherwise dictate our experience.” WF

Externals:
“There is only one road to happiness—let this rule be at hand morning, noon, and night: stay detached from things that are not up to you.” Epictetus

“Not being able to govern events, I govern myself, and if they will not adapt to me, I adapt to them.” Montaigne

Make sure your center of gravity stays within, that way the foundation of your happiness never gets destroyed through loss or disappointment due to things beyond your control. (summarizing Schopenhauer)

Perspective:
“The long view is good for morale. If it is an affront to the ego, it is also an antidote to vanity, ambition, and greed.” WF

“Imagine the vast abyss of time, and think of the entire universe; then compare what we call a human lifetime to that immensity. You will see how tiny a thing it is that we wish for and seek to prolong.” Seneca

“We believe these affairs of ours are greater because we are small.” Seneca

Death:
For the Stoics, meditation on death is a tool to promote humility, fearlessness, moderation, and other virtues.

“Only fools are attached to their bodies by a fear of death rather than a love of life.” Montaigne

“You are mistaken if you think that only on an ocean voyage is there a very slight space between life and death. No, the distance between is just as narrow everywhere.” Seneca

“We must make it our aim to have already lived long enough.” Seneca

Desire:
“You will learn the truth by experience: the things that people value highly and try hardest to get do them no good once they have them.” Epictetus

“We go panting after things unknown and things to come, because the things that are present are never enough. It is not, in my view, that they lack what it takes to satisfy us, but rather that we hold them in an unhealthy and immoderate grip.” Montaigne

“The measure of what is necessary is what is useful.” Seneca

“Natural desires are finite; those born of false opinion have no place to stop.” Seneca

“The desires that have limits come from Nature. The ones that run away from us and never have an end are our own. Poverty in material things is easy to cure; poverty of the soul, impossible.” Montaigne

“Do you not realize that all things lose their force because of familiarity?” Seneca

“We value nothing more highly than a benefit when we are seeking it, and nothing less highly once we obtain it.” Seneca

“That man will never be happy whom the sight of a happier man will torment.” Seneca

“When any calamity has been suffered, the first thing to be remembered is how much has been escaped.” Samuel Johnson

Wealth and pleasure:
“Lack of moderation is the plague of pleasure. Moderation is not the scourge of pleasure, but the seasoning of it.” Montaigne

“What it has made necessary for man, nature has not made difficult. But he desires clothing of purple steeped in rich dye, embroidered in gold, and decorated with a variety of colors and designs: it is not nature’s fault but his own that he is poor.” Seneca

“On hearing of the interesting events which have happened in the course of a man’s experience, many people will wish that similar things had happened in their lives too, completely forgetting that they should be envious rather of the mental aptitude which lent those events the significance they possess when he describes them.” Schopenhauer

What others think:
“Who does not willingly exchange health, tranquility, and life itself for reputation and glory—the most useless, worthless, and counterfeit coin that circulates among us?” Montaigne

“In all we do, almost the first thing we think about is, what will people say; and nearly half of the trouble and bothers of life may be traced to our anxiety on this score.” Schopenhauer

“Soon you will have forgotten everything; soon everything will have forgotten you.” Marcus Aurelius

“The success of the insult depends on the sensitivity and indignation of the victim.” Seneca

“Remember that you are insulted not by the person who strikes or abuses you but by your opinion that these things are insulting.” Seneca

“No one becomes a laughingstock who laughs at himself.” Seneca

“Do I deserve these things that happen to me? If I deserve them, there is no insult; it is justice. If I don’t deserve them, let the one who does the injustice blush.” Seneca

Valuation:
“This why I lost my lamp: because a thief was better than I am at staying awake. But he bought the lamp at a high price. In return he became a thief, he become untrustworthy…” Epictetus

Self-esteem is the price you pay for unethical acts.

“If you set a high value on liberty, you must set a low value on everything else.” Seneca

Emotion:
“We suffer more in conjecture than in reality…We magnify our sorrow, or we imagine it, or we get ahead of it.” Seneca

Adversity:
“It is not hardships that are desirable, but the courage by which to endure them.” Seneca

“It is the act of an ill-instructed man to blame others for his own bad condition; it is the act of one who has begun to be instructed, to lay blame on himself; and one whose instruction is complete to blame neither another nor himself.” Epictetus

“My formula for greatness in a man is amor fati: the fact that a man wishes nothing to be different, either in front of him or behind him, or for all eternity.” Nietzsche 

“Those who are without skill and sense as to how they should live, like sick people whose bodies can endure neither heat not cold, are elated by good fortune and depressed by adversity; and they are greatly disturbed by both.” Plutarch

“Fire tests gold, adversity brave men.” Seneca

“I judge you unfortunate because you have never been unfortunate: You have passed through life without an antagonist; no one will ever know what you can do, not even you yourself.” Seneca

“Pain is neither unbearable nor eternal if you consider its limits, and don’t add to it in your imagination.” Marcus Aurelius

“Pain takes up only as much space as we allow to it.” Montaigne

Virtue:
“Let nothing be done in your life that will cause you fear if it is discovered by your neighbor.” Epicurus

“It is a rare life that maintains its good order even in private. Everyone can play his role and act the honest man on the stage…” Montaigne

“Kindness is invincible, if it is genuine and not insincere or put on as an act.” Marcus Aurelius

Learning:
“No one can live happily or even tolerably without the study of wisdom. Wisdom, when achieved, produced a happy life.” Seneca

“Do you want to know why your running away doesn’t help? You take yourself along. Your mental burden must be put down before any place will satisfy you.” Seneca

“Associate with those who will improve you. Welcome those whom you yourself can improve. The process is mutual; for people learn while they teach.” Seneca

“The mind is not like a bucket that requires filling, it is like wood that needs igniting—nothing more—to produce an impulse to discovery and a longing for the truth.” Plutarch

“The last occupation of the preoccupied man is living—and there is nothing that is harder to learn.” Seneca

Stillness Is the Key – Ryan Holiday

Stillness Is the Key – by Ryan Holiday
Date read: 4/3/20. Recommendation: 9/10.

Holiday has his formula down and he nails it each time. Short, succinct chapters with relevant stories pulled throughout history to illustrate his main ideas. Busyness is a distraction we use to avoid putting in the real work that we must do in order to achieve a sense of stillness. Otherwise, we’ll always be running from something and never learn to be content with ourselves or appreciate the present moment. The ability to pause, reflect, and come back to the now is one skill that great leaders, thinkers, artists, and athletes all have in common. We could all benefit from creating more room for stillness—to limit our inputs, better appreciate the moment we’re living in right now, focus on our own character, and keep things in perspective.

See my notes below or Amazon for details and reviews.

My Notes:

Being present:
“You have plenty on your plate right now. Focus on that, no matter how small or insignificant it is. Do the very best you can right now. Don’t think about what detractors may say. Don’t dwell or needlessly complicate. Be here. Be all of you.” RH

“There is no stillness for the person who cannot appreciate things as they are, particularly when that person has objectively done so much.” RH

You already matter. You don’t need to prove anything else. 

Limiting your inputs:
Success isn’t about catching everything before it falls through the cracks, it’s about knowing what to let fall through. 

“Knowing what not to think about. What to ignore and not to do. It’s your first and most important job.” RH

To reach a relaxed state of concentration where you can do your best, don’t overanalyze, just do the work: Chop wood, carry water. 

Journaling for reflection:
Journaling = spiritual windshield wipers (Julia Cameron). Demands and creates stillness. 

In victory learn when to stop:
“Eventually one has to say the e-word, enough. Or the world says it for you.” RH

Joseph Heller (Catch 22) in conversation with Kurt Vonnegut at the fancy party in New York City at some billionaire’s second home: “I’ve got something he can never have. The knowledge that I’ve got enough.”

“When you realize there is nothing lacking, the whole world belongs to you.” Lao Tzu

“More does nothing for the one who feels less than, who cannot see the wealth that was given to them at birth, that they have accumulated in their relationships and experiences.” RH

“If a man can reduce his needs to zero, he is truly free: there is nothing that can be taken from him and nothing anyone can do to hurt him.” John Boyd

The path to stillness:
Develop a strong moral compass.
Street clear of envy and jealousy and harmful desires.
Come to terms with the painful wounds of your childhood
Practice gratitude and appreciation for the world around you.
Cultivate relationships and love in your lives.
Place belief and control in the hands of something larger than themselves.

“Give more.
Give what you didn’t get.
Love more. 
Drop the old story.” RH

Character:
“We develop good character, strong epithets for ourselves, so that when it counts, we will not flinch.” RH

“Always remember, others may hate you, but those who hate you don’t win unless you hate them. And then you destroy yourself.” Nixon

Perspective:
“In the face of the Sublime, we feel a shiver…something too large for our minds to encompass. And for a moment, it shakes us out of our smugness and releases us from the deathlike grip of habit and banality.” Robert Greene

“The moon you’re looking at tonight is the same moon you looked at as a scared young boy or girl, it’s the same you’ll look at when you’re older—in moments of joy and in pain—and it’s the same that your children will look at in their own moments and their own lives.” RH

“When you step back from the enormity of your own immediate experience—whatever it is—you are able to see the experience of others and connect with them or lessen the intensity of your own pain.” RH

“Here is my secret. It is very simple: It is only with the heart that one can see rightly, what is essential is invisible to the eye.” Antoine de Saint-Exupéry, The Little Prince

High Growth Handbook – Elad Gil

High Growth Handbook – by Elad Gil
Date read: 3/21/20. Recommendation: 9/10.

There are tons of resources out there for starting a company, but this book is a resource for scaling one. Gil focuses on tactical advice for scaling a company from ten employees to thousands. He emphasizes that the advice is meant to be painfully tactical in order to avoid the platitudes from investors who have never run or scaled their own company. This book is most valuable for founders, executives, and employees who are facing hypergrowth and scaling for the first time. Gil covers everything from the role of the CEO and managing the board to recruiting, organizational structure, product management, financing, and valuation. An incredible resource filled with dozens of relevant interviews with leaders who have real experience scaling great teams and products.

See my notes below or Amazon for details and reviews.

My Notes:

Focuses on tactical advice for scaling a company from 10-20 employees to thousands. Tons of resources on starting a company, this is a book that serves as a resource for scaling one. 

Most valuable for founders, CEOs, and employees who are facing hypergrowth and scaling for the first time. 

Skin in the game: “The advice presented here is meant to be painfully tactical and to avoid the platitudes you will get from investors who have never run or scaled a company.” EG

Distribution matters:
It’s a myth that most successful tech companies are product-centric. In fact, most are distribution-centric. Startups with better products get beaten by companies with better distribution channels.

“Since focusing on product is what caused initial success, founders of breakout companies often think product development is their primary competency and asset. In reality, the distribution channel and customer base derived from their first product is now one of the biggest go-forward advantages and differentiators the company has.” EG

Viability:
Tactics to stay viable = product iteration, distribution, mergers and acquisitions, moats (defensibility). 

Moats + Pricing:
“The definition of a moat is the ability to charge more.” Marc Andreessen

“Charging more is a key lever to be able to grow. And the companies that charge more therefore tend to grow faster.” Marc Andreessen

If you charge more you can allocate more to both distribution efforts and R&D.

Higher prices = faster growth. 

Product:
“Give me a great product picker and a great architect, and I’ll give you a great product.” Marc Andreessen

Product picker/manager/originator = people who can actually conceptualize new products. Great architects = people who can actually build it. 

“Great product management organizations help set product vision and road maps, establish goals and strategy, and drive execution on each product throughout its lifecycle.” EG

“Bad product management organizations, in contrast, largely function as project management groups, running schedules and tidying up documents for engineers.” EG

Product managers are responsible for:

  1. Product strategy and vision (reflect the voice of the customer)

  2. Product prioritization and problem solving

  3. Execution (timelines, resources, and removal of obstacles)

  4. Communication and coordination

Characteristics of great product managers:

  1. Product taste

  2. Ability to prioritize

  3. Ability to execute

  4. Strategic sensibilities (how is the industry landscape evolving?)

  5. Top 10% communication skills

  6. Metrics and data-driven approach

Interviewing PMs:

  1. Product insights

  2. Contributions to past successful products

  3. Prioritization

  4. Communication and team conflicts

  5. Metrics and data

Product Management Processes:

  1. PRD templates and product roadmaps: Build agreement and clarity on what you are building. What are the requirements for the product itself? Who are you building this for? What use cases does the product meet? What does it solve for and explicitly not solve for? What are the main features and what does the product do? What are the main product dependencies? A PRD may include wireframe that roughly sketch out the product user journey.

  2. Product reviews

  3. Launch process and calendar

  4. Retrospectives

Small, self-sufficient teams:
“There are exceptions, but in most cases, you need original thinking and speed of execution, and it’s really hard to get that in anything other than a small-team format.” Marc Andreessen

Design: Usability, how do we design this? Create the optimal user experience.

Engineering: Feasibility, how can we build this? How can technical road map drive product and vice versa. 

Product: Viability, should we build this? Set product vision and road map to ensure the company builds a product that the user needs. Make trade-offs between design, engineering, and business concerns.

Traits to look for in executives:

  1. Functional area expertise: Do they understand the major issues and common failure points for their functions?

  2. Ability to build and manage a team in those functional areas: Do they know how to motivate people in their functions?

  3. Collegiality: Do they do what’s right for the company even if it’s not in their best interest? Create mutually supportive environment.

  4. Strong communication skills: Do they have cross-functional empathy?

  5. Owner mentality: Do they take ownership of their functions and make sure they are running smoothly and effectively?

  6. Smarts and strategic thinking skills: Do they think strategically and holistically about their functions? Are they first principle thinkers? Can they apply their expertise in knowledge in the context of your company, team, and product? Or do they just try to implement exactly what they did in their last role?

External hires: “The way to retain people who are performing and who you really want to retain is to hire someone that they can learn from.” Keith Rabois

Flagship offices in the era of remote work:
Onboarding at headquarters helps to build initial connections and creates significant long-term value. 

With remote teams, create a great teleconferencing setup and consider the timing of your key meetings.

Who to emulate?
“I think people should select carefully the companies they seek to emulate and learn lessons from.” Patrick Collison

With great software companies in China (JD, Tencent, Alibaba), there’s a lack of entitlement, complacency, and a determination that there’s a void of in Silicon Valley.

Interviewing (to remove unconscious bias):

  1. Articulate the relevant qualifications for every role.

  2. Designing specific questions to assess for each qualification.

  3. Limiting the domains that each interviewer has to assess. Don’t go in and try to decide “Should we hire this person?” What you want to focus on is, “Does this person meet what we need on these two things?” When you’re trying to assess people on five different areas, it’s really hard, and you start to take shortcuts/allow biases to factor in. 

  4. Create rubrics to help interviewers evaluate answers to the questions that they’re asking.

Reboot – Jerry Colonna

Reboot: Leadership and the Art of Growing Up – by Jerry Colonna
Date read: 3/4/20. Recommendation: 9/10.

This one surprised me in all of the best ways. And it was a book that I just happened to read at the right time. Reboot focuses on self-inquiry and challenges us to consider the question: “What do I believe to be true about work, leadership, and how we may live our lives?” Colonna emphasizes that better humans make better leaders. But first, you must learn to lead yourself. That means looking at the reality of all that we are–not fixing blame to ourselves, but understanding with clarity what’s really happening in our lives. Colonna discusses his ideas on personal growth, stillness, purpose, self-worth and self-inquiry. The book also includes dozens of thought-provoking journaling invitations. Pick this one up when you feel like you’re at a point where you’re ready to have difficult conversations with yourself.

See my notes below or Amazon for details and reviews.

My Notes:

Focuses on the question: “What do I believe to be true about work, leadership, and how we live our lives?” Better humans make better leaders. 

Writing:
“Write the story that you were always afraid to tell. I swear to you that there is magic in it.” Dorothy Allison

“To speak of such things without being willing to reveal your own actualization, your own journey to adulthood, would be hollow and empty.” JC

“To live well is to see wisely and to see wisely is to tell stories.” Pádraig Ó Tuama

“I am living with aliveness when I write, regardless of whether my words are published.” JC

Self-inquiry:
“Slowing down the movie of our lives, seeing the frames and how they are constructed, reveals a different way to live, a way to break old patterns, to see experiences anew through radical self-inquiry.” JC

Trace forward to reframe these beliefs. But choosing a new path forward requires an awareness and knowing. 

“Listening opens that which pain has closed.” JC

“Listen and don’t fix.” JC

“To be free, each of us must come to understand the causes and conditions of our childhood. For these gave rise to the rules by which we, as adults, live.” JC
^Rules that kept you safe as a kid, like stay small, don’t stand out, careful now, don’t make mistakes.

Strong back, open heart:
“The back of the warrior is strengthened by knowledge of knowing the right thing to do. The soft, open heart is made resilient by remembering who you are, what you have come through, and how those things combine to make you unique as a leader.” JC

“Learning to lead yourself is hard because it requires us to look at the reality of all that we are—not to fix blame on ourselves but to understand with clarity what is really happening in our lives.” JC

“The call to lead well is a call to be brave and to say true things.” JC

Growth:
“Growth is painful; that’s why so few choose to do it.” JC

The goal is to buy low and sell high, not buy lowest and sell highest.

“We forge our truest identity by putting our heads into the mouths of the scariest demons, the realities of our lives.” JC

“When we fail to grow, we hold back others.” JC

Stillness:
“The forest knows / Where you are. You must let it find you.” David Wagoner

What are you not saying that needs to be said?

“Slow down. Stand still. Breathe. Let the first find you. Then you can begin to ask yourself the hardest questions: Who am I? What do I believe about the world? What do success and failure mean to me (and not to everyone else)?” JC

“When we stand still, we run the risk of remember who we are. When we stop the spinning, we run the risk of confronting the fears, the demos who have chased us all our lives.” JC

“You might as well show up, as you are.” 

Jerry came to this realization during a conversation with his son when his son noticed something was off. Son said, “Dad, you might as well tell me what’s going on, because if you don’t. I’m going to make shit up and it’s gonna be negative about me.”

What’s within your control?
“All beings own their own karma, their happiness or unhappiness depends on their actions, not my wishes for them.” Sharon Salzberg

The path towards purpose:
“The path to a purpose-grounded life is messy, muddy, rock-strewn, and slippery.” JC

Those in their 20s hold themselves to an unrealistic standard of a non-messy, straightforward unfolding of their lives. This is not how things play out. 

“Discovering your purpose, feeling your way into that aliveness, requires clambering up rocky cliff faces, leaping chasms, tucking oneself deep into clefts and deeper and deeper into the Earth. It demands the willingness to dip into the crack of the tree as well as the bravery to step out of it.” JC

“Aliveness comes from living a life of personal integrity in which our outer actions match our inner values, beliefs, wishes, and dreams.” JC
^Similar to Naval Ravikant’s, “Self-esteem is just the reputation that we have with ourselves.”

“I can’t think of a sadder way to die than with the knowledge that I never showed up in this world as who I really am. I can’t think of a more graced way to die than with the knowledge that I showed up here as my true self, the best I know how, able to engage life freely and lovingly because I had become fierce with reality.” Parker Palmer

The Conquest of Happiness – Bertrand Russell

The Conquest of Happiness – by Bertrand Russell
Date read: 2/23/20. Recommendation: 8/10.

An accessible introduction to the work and philosophy of Bertrand Russell. In many ways, The Conquest of Happiness is a predecessor to the self-improvement genre that exists today. The book is broken down into two main sections, causes of unhappiness and causes of happiness. I got the most out of the second section as he discusses finding in harmony the stream of life and developing a zest for life. As Russell suggests, “The secret to happiness is this: let your interests be as wide as possible, and let your reactions to the thing and persons that interest you be as far as possible friendly rather than hostile.”

See my notes below or Amazon for details and reviews.

My Notes:

Teach and be taught, rather than judge and be judged mindset:
“The secret to happiness is this: let your interests be as wide as possible, and let your reactions to the thing and persons that interest you be as far as possible friendly rather than hostile.”

Expand your interests:
“The more things a man is interested in, the more opportunities of happiness he has and the less he is at the mercy of fate, since if he loses one thing he call fall back upon another.”

Alex note: Every year that passes, life should be more enjoyable. You discover more of the things you love and are able to recognize more things that you don’t. 

Alex note: With age, there’s a diminishing preoccupation with yourself. Take yourself less seriously, get out of your own head, avoid tricking yourself into believing that you are the center of the universe, and you will be happier. 

“But the monk will not be happy until the routine of the monastery has made him forget his soul.”

Zest:
“The man who has the zest for life has the advantage over the man who has none. Even unpleasant experiences have their uses to him.”

The adventurous enjoy even the unpleasant experiences…”It gives them pleasure to have their knowledge of the world increased by this new item.”

The Stream of Life:
“To be happy in this world, especially when youth is past, it is necessary to feel oneself not merely an isolated individual whose day will soon be over, but part of the stream of life flowing on from the first germ to the remote and unknown future.” 

“The happy man feels himself a citizen of the universe, enjoying freely the spectacle that it offers and the joys that it affords, untroubled by the thought of death because he feels himself not really separate from those who will come after him. It is in such profound instinctive union with the stream of life that the greatest joy is to be found.” 

Alex note: Life is motion. The goal is to remain in harmony with that motion as best you’re able to.

“Success can only be one ingredient in happiness, and is too dearly purchased if all the other ingredients have been sacrificed to obtain it.”

Work:
“Even the dullest work is to most people less painful than idleness.”

“We are less bored than our ancestors were, but we are more afraid of boredom.”

Unhappiness:
“I believe this unhappiness to be very largely due to mistaken views of the world, mistaken ethics, mistaken habits of life, leading to destruction of that natural zest and appetite for possible things upon which all happiness, whether of men or animals, ultimately depends.” 

Shape Up – Ryan Singer

Shape Up – by Ryan Singer
Date read: 2/12/20. Recommendation: 8/10.

One of the best guides out there for modern product development and the familiar challenges that product teams face. Part one aims to provide a better language to deal with and describe risks, uncertainties, and challenges that define product development. Part two outlines processes Basecamp (where Ryan leads product) uses to make meaningful progress on their products. The book mainly focuses on the risk of getting stuck or bogged down in last quarter’s work, wasting time on unexpected problems, and not being free to do what you want tomorrow.

See my notes below or download a free copy from Basecamp.

My Notes:

Part one aims to provide a better language to deal with and describe risks, uncertainties, and challenges that define product development. Part two outlines processes Basecamp uses to make meaningful progress on their products.

Focuses on the risk of getting stuck, the risk of getting bogged down in last quarter’s work, wasting time on unexpected problems, and not being free to do what you want to do tomorrow. 

Shaping:
Be critical about the problem—what are we trying to solve, why does it matter, what counts as success, which customers are affected, what is the cost of doing this instead of something else?

To set proper boundaries, you will need a raw idea, an appetite, and a narrow problem definition.

Well-shaped work has a thin-tailed probability distribution. Removes as many unknowns and tricky problems from the project as possible. Project should have independent, well-understood parts that assemble together in known ways.

Set the appetite:
How much time and attention is the raw idea worth? Is it worth a quick fix? Is it worth an entire cycle? Would we redesign what we have to accommodate for this? Or is this only worth it if we can pull it off with a small tweak?

Set the appetite. Start with a number and end with a design. This serves as a creative constraint. Estimates are the opposite and leave too much room for error.

Estimates are only beneficial or accurate when a team has done that exact task multiple times before. They don’t account for uncertainty as you’re trying to define what you actually need to do.

You are shaping for a fixed time window. 

Not, “is it possible to do X?” But, “Is X possible in 6 weeks?”

Scope hammering:
Hammer down scope by narrowing the problem definition.

Narrow understanding of the problem by flipping the question from “what could we build?” to “what’s really going wrong?” You want to understand what’s driving this request, where the workflow is breaking down without this feature.

When you get a request to build something, focus on the when instead of why. This will provide more context. “What was this person doing when the thought occurred to ask for this?”

Be cautious of “redesigns” or “refactoring” that aren’t driven by a clear problem or a single use case.

Critically assess the nice-to-haves. Ask, would this feature still be valuable without this?

The scope is right when…

  1. You feel like you can see the whole project and nothing important that worries you is hidden down in the details.

  2. Conversations become more flowing because the scope gives you the right language.

  3. Easy to organize new tasks because you know the buckets they fit into.

“Every project is full of scope we don’t need. Every part of a product doesn’t need to be equally prominent, equally fast, and equally polished. Every use case isn’t equally common, equally critical, or equally aligned with the market we’re trying to sell to.”

Instead of trying to prevent scope from growing. Empower teams with the autonomy to cut back on scope themselves.

Good enough?
“The best is relative to your constraints.”

“We can only judge what is a ‘good’ solution in the context of how much time we want to spend and how important it is.” 

Anchor the point of comparison away from up towards the ideal and instead down towards the baseline. The baseline is the current reality for customers and how they solve this problem today. 

Seeing work in comparison to current alternative will improve morale and sense of progress made. 

Pitch:
Includes problem, appetite, solution, rabbit holes, and no-gos. See page 37 for more details.

Questions to ask at the betting table:
Does the problem matter? 

Is the appetite right?

Is the solution attractive?

What do we build first?
Start in the middle. Find something that’s 1) core to the concept, 2) small enough to complete in a few days and build momentum, 3) novel, meaning, something new that we haven’t worked on which will help eliminate uncertainty.

Choose the most important problems with the most unknowns to tackle first. This will help get you to the top of the hill. Then you can save the most routine and least worrisome items for the way down.