Best Books I Read in 2019

One of the less-talked about benefits of reading is being able to “humble brag” about all the books you’ve read.

On a completely unrelated note, here are the best Books I read in 2019.

If one of your goals is to read more in the new year, you should start with these books.

(note: There are typos in this post. Consider this my personal rough draft that I am sharing for public knowledge. For posts like these, the marginal value of fixing typos, is less than the marginal time spent fixing typos.)

You can also read all my book notes and reviews.

How to Fail at Everything and Still Win Big (buy on Amazon)

Basically a self-help book that is actually different from any other self-help book I’ve ever seen.

I don’t think I’ve ever read a self-help book cover to cover because those aren’t my type of books but Scott Adams has a remarkable ability to explain concepts in an extrememy concise, pithy, funny and memorable way. He is also extremely practical and tangible with a lot of his advice. I think engineers and people in STEM will like this book because it’s written in a very pragmatic way he is also super contrarian so a lot of things he says are not things you have heard before.

This is probably the best book I read in 2019. If you want a very practical, no BS book on how to be more successful, I strongly recommend you read this book.

Tangentially, Scott Adams himself is also an exceptionally persuasive writer. I’ve read a lot of good books, by a lot of great authors,authors that could be described as smart or articulate but I don’t think any of them are as persuasive as Scott Adams.

I really wish I started taking book notes earlier, so I could have notes for this book to refer back to, it’s so full of practical advice. Here are the highlights. Quoted directly from page 3:

  1. Goals are for losers.
  2. Your mind isn’t magic. It’s a moist computer you can program
  3. The most important metric to track is your personal energy
  4. Every skill you acquire double your odds of success
  5. Happinesses is health plus freedom
  6. Luck can be managed, sort of.
  7. Conquer shyness by being a phoney (in a good way).
  8. Fitness is the lever that moves the world.
  9. Simplicity transforms ordinary into amazing

other notes

  • often we just need permission from someone, anyone, to initate a change in our life [49]

His important patterns for sucess, which he stresses is purely anecdotal and excludes the ones that are 100 percent genetic

  1. Lack of fear of embarassment
  2. Education (the right kind)
  3. Exercise

The Amazon links are affiliate links.

Thinking in Bets (full notesbuy on Amazon)

Thinking in Bets is a book about how to make better decisions when you don’t have all the facts. People often say life is like chess but really it’s more like Poker because there is information asymmetry and luck. Lots of good insights in this book and I would strongly recommend following Annie Duke on Twitter and me @tomiwa1a.

She does such a good job of explaining human behavior using data, stories and humor. My favorite part of the book is that she doesn’t just explain human behavior she also offers practical solutions on how to make better decisions and improve your behavior pattern as you will see in my notes below. I think she could write a really good book on relationships/dating/marriage and it would be popular with both men and women.

  • “Resulting”: Judging a decision based on the result instead on if the process you followed was right. For example, Pete Carrol’s decision to pass the ball in 2016 Super Bowl [5]
  • Ask For Temporary Agreement in Truth-Seeking: If someone is emotionally offloading to us, ask if they just want to vent or are looking for advice for what to do next. She suggests the phrase. “Do you want to just let it all out [and talk about it] or are you looking for what to do next?” [174]
  • Very profound quote on how we should think about happiness as a long term stock that steadily rises and pay less attention to the day-to-day fluctuations. Very cool graph of Berkshire long-term vs short-term stock price to illustrate this [192].

The Organized Mind (full notesbuy on Amazon)

In a world with so much information how do you sort through all the noise and make sense of what actually matters?

Quick highlights

  • “AI/social media/ the internet is ruining everything”, they said the same thing about books and the printing press [14]
  • How to teach children to thrive in an information society
  • The role of doctors in modern medicine, why some doctors justify lying to their patients and why most doctors may end up getting replaced by machine learning algorithms [249]
  • How to organize your digital files: Make search a forethought, how will I look for this when I need it [320]
  • Sleeping more efficiently with bimodal sleep [189]

Lebron Inc. (full notesbuy on Amazon)

Lebron Inc. by Brian Windhorst is about how Lebron has built his business empire from his Freshman year in St. Vincent St. Mary’s in Akron in 2001 (tk verify Lebron high school freshman year) to his new team Los Angeles Lakers in 2019. Brian Windhorst has been following Lebron since 1999 so he is one of the few well known sports media people that has been following Lebron literally his entire career, and even before that.

Lebron is my favorite athlete and one of the most influential people on modern culture. I have a lot of respect for all of the things he does off the court, from I-Promise schools to Uninterrupted, to how he posts on Instagram #tacotuesday, I am totally here to #WitnessGreatness. I am also super observant about how aware he is both on the court and off the court.

  • Lebron grew up extremely poor, the neighborhood he grew up in was actually at the bottom of a hill and they called it “the bottom”

-In 2006, record industry was being disrupted by streaming and Jimmy Iovine and Dr. Dre were loking for ways to make money [121]

  • Dr. Dre suggested shoes, Iovine suggested speakers, they settled on headphones (Beats by Dre)
  • The 2008 summer olympics, Lebron encouraged the US mens’ basketball team to wear the headphones and they invited other athletes to wear it
  • Brian points out that when Lebron said “taking my talents to South Beach” that’s exactly what Kobe said (taking my talents to) in 1996 when he was announcing that he was going straight from high school to the NBA [157]

But What If We’re Wrong (full notesbuy on Amazon)

Contrarianism is cool right now. But What If We’re Wrong by Chuck Klosterman is one of the best books that I’ve read on how to be a contrarian thinker (tied with Nassim Taleb’s Antifragile).

As you can see, one of my longest book reviews yet. An extremely fascinating and insightful book. The kind of book where you read certain parts and you will pause and find yourself thinking, “that can’t possible be true… but what if it is…”. If you want to become a more creative thinker or think about things from a perspective you haven’t considered before I strongly recommend But What If We’re Wrong.

Peter Thiel says that it’s not enough to be contrarian, you have to be contrarian and right. I don’t know if Klosterman is necessarily “right” (and to be fair, he’s not suggesting a lot of the ideas in the book as being “right”) but I think he does an excellent job of creating a new lens on how to think about popular ideas or what I call, “generally accepted stories we tell ourselves”.

“But I know these imperative perspectives have no origin in my own brain. The first time I ever heard Frank Lloyd Wright’s name, I was being told he was brilliant, which means the first time I looked at a building he designed, I thought either, “That is what brilliance looks like,” or “This is what everyone else recognizes as brilliance… [91]

  • Interviews Neil DeGrasse Tyson: “I will add that in 1603 the microscope was invented, and in 1609 the telescope was invented. So these things gave us tools to replace our own senses, because our own senses are quite feeble when it comes to recording objective reality…I can establish an objective truth that’s not a function of my state of mind, and you can do a different experiment and come up with the same result” [100]
  • Funny story about two people having a “beer conversation” about the meaning of life and if God exists. A 3rd person walks in says they are both wrong. That “It turns out our moral compass comes from neither God nor ourselves. It comes from Brenda. Brenda is a middle-aged computer engineer living in the year 2750, and she designed the simulation that currentl contains all three of their prefab lives”[127]

Dataclysm (full notesbuy on Amazon)

Dataclysm is a book by Christian Ruder, the founder of OkCupid, a dating site. The book is about the site’s data can tell us about relationships and human behaviour. If you are interested in learning more about dating habits in society and more broadly, what people say they like versus what they actually like, I would recommend you read this book.

  • One of my favorite meta takeaways from this book is that directly observing people’s behaviours is much more effective than asking them due to the Hawthorne effect
  • Essentially, if you ask someone on the phone, “Would you date someone from a different race than you?” some people may lie and say yes because it’s the socially desirable thing to say, even though they would only date people of the same race.
  • However, if you just observed their behaviour on a dating site and tracked how often they messaged people of opposing races, that would be a lot more instructive
  • “men and women experience beauty unequally” [128]

How to be a Capitalist without Any Capital (full notesbuy on Amazon)

How to be a Capitalist without Any Capital by Nathan Latka is a book about how to start building wealth when you don’t have any money.

Very tactical and highly actionable, though I occasionally got a bit of salesy, used-car salesman, penny-pinching, vibes and there are some micro-optimizations and “hacks” that I feel may not even make a meaningful impact on building long-term wealth.

However, I would remind readers that the best way to build long-term wealth, in my opinion is to make something people want. Give people value in order to get what you want.

  • One thing I really admire about him is his transparency and he shows his numbers of how much money he makes and spends, more personal finance writers should do this

Shows a picture of his tax return [6]

  • Offers a lot of interesting insights on how to watch your competitors are doing and how to learn from them (similar web, todoist, ahrefs, semrush, siftery) [214]
  • I found it very interesting how he alludes to Software Private equity being his next big move [249]
  • I am also bullish on technology/software private equity, I actually took a private equity course in business school (course review of the private equity class is coming soon, subscribe to my blog to get notified when it comes out)
  • I remember reading a stat somewhere that the best performing private equity firms were technology/software focused: Vista Equity partners led the group (maybe this is cyclical) but there’s a lot of untapped opportunity in software still. It feels like we are at peak SAAS but sometimes it seems like we have barely even scratched surface.

Win Bigly (buy on Amazon)

Scott Adams explains the different tactics and persuasion moves that Donald Trump used to win the 2016 US Elections. Most people were surprised by Trump’s win but he was on of the few people that predicted his win.

He references Robert Cialdini’s book, Influence a lot. I’ve read both and would recommend both books as they teach a lot about human behaviour but Scott Adams’ humorous writing style makes Win Bigly an easier, and very enjoyable read. Though, some of the conclusions are slightly depressing at first when the book makes you realize how irrational we humans can be, but then you feel liberated and happier because you have a better toolbox for understanding how the world works.

Even the book title is funny: “Win Bigly: Persuasion in a World Where Facts Don’t Matter”

The Soul of Basketball (full notesbuy on Amazon)

The Soul of Basketball is about the 2010-11 NBA season from the perspective of Lebron James in Miami Heat, Doc Rivers coaching the Boston Celtics, Kobe Bryant in the Los Angeles Lakers and Dirk Nowitzki with the Dallas Mavericks.

I find the NBA to be such a fascinating league. I have recently become very interested in media, culture and where humans are spending the most attention. The NBA has done such an impressive job of innovating to stay culturally relevant and creating a platform for NBA players to be the most culturally relevant athletes with the most leverage in the modern era.

  • Biggest takeaway from this book is the idea of leverage and the “player empowerment” movement in the NBA
  • Lebron’s generation was the “AAU” generation: players who were told they were great and already had a platform in high school BEFORE they played an NBA game [12, 26 74,]
  • NBA talent like most social things in life follow a power law distribution
  • In simplest terms: the best 20 players in the NBA probably have 80% of the market value or 80% of the “championship winning talent”
  • A lot of very interesting anecdotes on how Mark Cuban “disrupted” the NBA in terms of bringing more transparency to NBA officiating, and marketing as owner of Dallas Mavericks [96].