What I Read 2019

Hi All,

Hope everyone enjoyed the holidays! Time to nurse your hangovers and peruse Bob’s Books from 2019. We have 30+ books for the year.

This year I’ve grouped the list into the following categories: 

  • Self-Improvement
  • Biographies
  • Sales, Marketing, Speaking
  • Health
  • Consciousness
  • Perennial rereads

I’ve ordered the books in each category from best to worst in my opinion.

All of these books were recommended by top performers (chess masters, political strategists, hedge fund managers, CEO’s, polymaths, etc.) as must reads.

If this was helpful, check out my lists from 2018, and 2017.



2019 Top Picks: 

(Scroll down for full list)

Self Improvement:

Atomic Habits – James Clear (320 pages) – I love books that are “How did it,” rather than “How to do it.” In high school, James suffered a severe brain injury during baseball practice when he was hit in the head by a bat. This nearly killed him. From there he was able to completely rebuild his mind and his body through the development of individual habits, going on to play college baseball, being selected as the top male athlete at Denison University, named to the ESPN Academic All-America Team (bestowed upon only 33 students nationwide), and receiving the President’s Medal – the university’s highest academic honor. James became an expert in the science of habit creation and elimination (in the case of bad habits). This book is the step-by-step guide to creating better habits. My favorite example from the book was the turn around of the British Cycling team. This team was SO bad for SO long that bike manufacturers would not let this national program use their products, as it would negatively impact sales… Woof. Yet during the ten-year span from 2007 to 2017, British cyclists won 178 world championships and 66 Olympic or Paralympic gold medals and captured 5 Tour de France victories in what is widely regarded as the most successful run in cycling history, while implementing these tactics.

Range – David Epstein (352 pages) – The subtitle says it all – “Why Generalists Outperform Specialists.” For years the gold standard for exceptional performance in any field was thought to be, “early and often.” The sooner we could throw kids into specialized training in a particular skill (golf, trumpet, math, etc.) the more likely they are to become exceptional. The best example of this is Tiger Woods. Tiger started swinging a golf club when he was 1 year old, broke 70 on a golf course at age 12, and the rest is history. Yet, as the book points out, this is the exception, not the rule. In fact, a number of studies illustrated that specialization, or the absence of varied experiences physically inhibits people’s perceptions and physical abilities. The first example it cites is a young man who played a number of different sports growing up, showing only a general adeptness at any particular one. He didn’t begin to focus on tennis specifically until high school. That man is Roger Federer, regarded as the greatest tennis player in history (20 Grand Slams and counting…).  This book breaks down the science behind the benefits of generalizing—collecting different experiences and skills from across broader modalities—to disrupt a given field and rise to the top.

Coach Wooden’s Pyramid of Success – John Wooden (160 pages) – John Wooden is likely the greatest basketball coach to ever live. Wooden coached UCLA to 10 NCAA championships in 13 seasons. Here he breaks down his pillars for success in any field. What I love about Wooden is his attention to detail – he teaches his player how to put their socks on because, “Incorrect socks cause blisters, blisters cause missed shots, missed shots lose championships.” Disclaimer: 50% of this book is focuses on religion and faith. That said, it’s still behooves everyone to pick this up.  

Digital Minimalism – Cal Newport (304 pages) – Cal does an excellent job of exposing how truly detrimental our phones, and social media are. It’s really astounding how optimized these systems are for keeping you glued to them.  It’s the second half of this book that I had trouble with. Cal works to outline how we can unglue ourselves from these time-suck traps. The problem is, Cal admits that he already lives off the grid and has never struggled with tech addiction. So many of his proposed tools and tactics are a bit academic and don’t seem easily implementable for the average person (they fail to utilize many of the tactics outlined in Atomic Habits). For those interested, I highly suggest reading the beginning of this book to understand what you’re up against, and then utilize the tools from Atomic Habits to combat big-data’s stronghold on us.


When I Stop Talking You’ll Know I’m Dead – Jerry Weintraub (304 pages) – This was my FAVORITE book of 2019. I listened to it on Audio and bought the hard cover version. I enjoyed it so much that upon completing it, I immediately listened to it again (and contemplated re-listening a 3rd time). Weintraub was one of the original Hollywood Power Players. He managed musical legends like Presley, Sinatra and John Denver. He produced plays, TV shows, movies (from Nashville to the Ocean’s 11 franchise). In his own words, “When I believe in something, it’s going to get done.” He once closed a deal by faking a heart attack. He won the respect of one of Chicago’s most powerful men, Arthur Wirtz, when he cursed Wirtz out for making him wait (Wirtz would go on to become one of Weintraub’s mentors). This book is the selective history of an exceptional story teller, showman, and businessman. It highlights what can be accomplished with the right amount of focus, determination, and creativity. I’ll be reading this again in 2020.

Trillion Dollar Coach – Eric Schmidt, Jonathan Rosenberg, and Alan Eagle (240 pages) – Bill Campbell helped to build some of Silicon Valley’s greatest companies (Google, Apple, and Intuit) and to create over a trillion dollars in market value. Bill mentored visionaries such as Steve Jobs, Larry Page, and Eric Schmidt, and coached dozens of leaders that shaped the world as we know it. I love this book. Bill’s a hard nosed, no nonsense, team-first coach who had the EQ of Opra and Tony Robbins combined.  One of Bill’s most notable quotes was, “I don’t take stock, I don’t take cash and I don’t take shit!” That’s right, he didn’t accept compensation for any of his advisory work with these visionaries or their companies. He felt it was his way of giving back to the community. It also allowed him to avoid politics and provide unvarnished feedback to anyone and everyone.  This book directs Bill’s principles and illustrates them with stories from the great companies and people with whom he worked and played. The result is a blueprint for forward-thinking business leaders and managers that will help them create higher-performing and faster-moving teams and companies.

The Education of a Coach – David Halberstam (288 pages) – Includes first 3 Super Bowls with Pats and appearances as Giants coordinator.

12: The Inside Story of Tom Brady’s Fight for Redemption – Casey Sherman (320 pages) – Includes first 7 of 9 Super Bowls Tom and Bill have been to.

Belichick – Ian O’Connor (512 pages) – Includes 8 out of 9 Super Bowls.

Grouping these 3 together. I’ve long been fascinated by one team’s utter dominance over the better part of two decades in the free agency, salary-capped, and parity-based NFL. What was most amazing is that each of these books hail Bill Belichick as the greatest coach in NFL history (and Tom as the best player), and yet none of them include ALL of the Super Bowls these guys appeared in! I loved reading about the habits and tools that these guys (including Robert Kraft) developed over the years to refine their excellence. Even better was learning about the failures, setbacks and blunders that they suffered on their incredible journey’s. I’ve ranked them in order of my favorites above.

Born to Run – Bruce Springsteen (528 pages) – Prior to this book all I knew about Bruce was the 2 or 3 songs I had of his on my Spotify. I got a further taste while watching The Defiant Ones on HBO. Bruce appeared to be complete obsessed with making exceptional music. This book did not disappoint. It reads as rich, rough, and poetic as a Springsteen song. This book was recommended as being similar to Steve Martin’s Born Standing Up, and Phil Knight’s Shoe Dog, in that it focused a lot on the early days of Bruce’s childhood. Like many of the greats I’ve studied, Bruce was commitment to excellence in everything he did. He began as a lackluster guitarist who plugged away ad nauseam until he became elite. He then looked at the market for music and determined that his niche could be powerful lyrics. So he devoted himself to creating powerful and potent lyrics. Bruce, like the other great’s I’ve read about, didn’t care about the money. He was simply obsessed with producing great music for his fan’s. Ten years after Born to Run released he still only had $20k to his name. For the better part of two decades, he devoted himself tirelessly to his craft before making any real money. It was never about the money or the fame. He just wanted to be heard, and to touch people’s souls with his music. Whether it was 100 people or millions, the number didn’t matter, as long as he was connecting with his fans.

Tiger Woods – (512 pages) – After reading Steve Williams memoir, and Range, I felt it was time I do a deep dive into Tiger Woods. This book goes deep. You quickly understand the full scope of Tiger’s intense upbringing. How both his parents pushed him to the limits physically and mentally to become, in his mom’s terms, a “cold-blooded assassin” on the course. It’s no surprise why he quickly became a machine in the golf world, and why he unraveled the way that he did. Throughout this book you swing between admiration, awe, and disgust. At the end I was unsure how to feel about Tiger. But, I still find myself rooting for him on the course as he, at age 43, continues to electrify the field and the sport. To examine it further might be too much to ask of him.

Sales, Marketing, Speaking:


To Sell Is Human – Daniel Pink (272 pages) – This is a re-read from 2018. In my opinion, it’s the best book on modern selling I’ve ever read. That said, this is not just for salesman. Each of us sells. Anytime you are looking to persuade, convince or otherwise influence someone’s actions, you are selling. Formerly, salesmen had all the info and disseminated it to the prospective client in a way that led the client to their product. This could be deceptive due to the asymmetry of the informational ownership (hence the ‘sleazy salesman’). Today with the internet everyone has access to the same info (generally speaking), so that asymmetry is gone! So why do we need salesmen? We need people who understand others’ perspectives, make messages clearer, and build lasting relationships. This book looks at the science of selling, which is really the science of human behavior and interaction. As we learned in Sapiens, storytelling and persuasion is what allowed humans to conquer the earth. So best learn how to do it right.

The Go-Giver – Bob Burg (176 pages) – This is a heartfelt story that demonstrates the power of interpersonal relationships, service, and paying it forward. The lessons in this book should be studied by everyone living in the modern, “me-first” world. Salespeople and Markers should always operate from these first principles. It’s no shock that this is a National Best Seller.

The Lost Art of Closing – Anthony Iannarino (240 pages) – Anthony is a sales genius. Every sales manager should have their team complete Anthony’s online course, and read this book. Like Nihill for speaking, Anthony has distilled the counterintuitive tools from every great book on sales and interpersonal relationships. Everything from pipeline creation, moving prospects through the sales funnel, down to time management is broken down in detail. This should be waiting on the desk of every new salesperson who joins your organization.

Never Split the Difference – Chris Voss (288 pages) – Chris was the FBI’s lead international kidnapping negotiator. Here he breaks down his tools and tactics for negotiation when lives hang in the balance you can’t afford to split the difference.  In his words, splitting the difference is like wearing one black shoe and one brown shoe. This book has the perfect balance of stories from the field and dissecting the principles of negotiation used in each scenario. This is the only book you need on this topic.

Influence – Robert Cialdini (336 pages) – This is one of those books on persuasion that everyone recommends (like How to Win Friends and Influence People). I’m not sure why it took me so long to read it (I had accidentally purchased it 3 separate times…). Cialdini does a nice job of walking through the behavioral principles behind persuasion like social proof, reciprocity, scarcity, and others. It’s no wonder everyone loves this book. That said, having previously read many other books on the topic, I didn’t find many new insights here. You could certainly save a lot of time by starting with this book or Never Split the Difference.

Let’s Get Rreal, or Let’s Not Play – Mahan Khalsa and Randy Illig (288 pages) – This is a great book on sales. But boy is it dense and technical. I underlined huge swaths of this one, but it’s not light reading. This is the text book for sales. That said, The Lost Art of ClosingTo Sell is Human, and Anthony Iannarino’s online course hit all the same info and are more approachable.

The First 90 Days – Michael Watkins (304 pages) – Several executives have told me they re-read this book each time they begin at a new organization. Given my recent career change, I felt I should crack this open. This book is mostly written for managers or folks entering into leadership roles (which mine was not). So large chunks of this book were less applicable to me. That said, there were plenty of helpful nuggets for integrating into a new organization – understanding the culture, learning how goals get set, and how to strategically execute on your initiatives. Solid read for anyone changing jobs.


Made to Stick – Dan and Chip Heath (291 pages) – While there’s more than 1 way to skin a cat, there’s really only a few ways to do it best. When it came to assessing advertisements, 89% of award winning ads fell into 6 basic categories/templates. This book breaks them down, highlights why they work, and outlines how to employ them in your marketing. Dan and Chip are some of my favorite writers. After devouring The Power of Moments last year, I had to burn through their other NYT Best Seller.

The 22 Immutable Laws of Marketing – Al Ries and Jack Trout (143 pages) – This was a re-read from 2017. It’s a quick read and a staple for anyone in sales, marketing or copy writing. These are the fundamentals that all the greats know by heart. Whether marketing your brand or selling yourself, these apply.

Talk Triggers – Jay Baer (271 pages) – Talk triggers is an element of marketing where customers can’t help but talk about something your organization does—e.g. Cheesecake Factory’s Menu size, Double Tree’s chocolate chip cookie at check-in, etc. This is a brilliant concept that every brand should seek to employ. The book reviews a number of case studies of organizations doing this well, and highlights how it can go wrong. These are not gimmicks or one-off ploys. A talk trigger must be directly in line with what the company does, and must be reproducible for every customer. I’d recommend this book to every marketing person.

Tribes – Seth Godin (160 pages) – I normally love Seth’s material (The DipPurple CowSeth’s Blog), but this one didn’t seem to strike a chord. The core premise is the need for leadership, and what Seth calls heretic-like thinking to break through norms and create tribes. The book doesn’t have chapters, and reads more like a series of semi-related blog posts stitched together. Seth is a great writer and an exceptional marketer. Any of these individual “blog posts” would have been nice in isolation, but stacked on top of each other felt a bit redundant.


Do You Talk Funny – David Nihill (208 pages) – This is, hands down, the best book on speaking and storytelling I’ve ever read. It the perfect highlight reel of every great book on the topic. In this book, David sets out to conquer his fear of public speaking via the Tim Ferriss method of full emersion + 80/20 optimization. David creates a faux website for a comedian named “Irish Dave.” With this as his “credibility” he spends a year booking paid comedy gigs, and performing at open mic’s, all the while making every mistake in the book as he learns the craft of comedy and public speaking. The book finishes with David making it to the finals of the Moth Story Telling competition in San Francisco. There, on stage in front of 4,000 people, his hilarious story earns him 2nd place. He would later meet the 1st place winner and asked her what her secret was (she had just beat out several professional comedians to earn the title). When she cited a blog post she’d read about the keys to storytelling, David was stunned. It was his blog post!! Whether you’re planning to hop on stage as a comedian, presenting in a business setting, or simply telling stories at the bar, you NEED to read this book. Can’t read? Check out David’s course on CreativeLive.

Talk Like TED – Carmine Gallo (288 pages) – This book distills what makes the best TED talks great, into 9 elements. It then further refines how to do each of these. It does a nice job of simplifying an esoteric concept like presentations. A lot of the book is dedicated to describing each TED Talk discussed for those who haven’t seen them. While the 9 elements were nice to see, and there was some helpful commentary, you get all of this info and more in Nihill’s, “Do You Talk Funny.”


10% Human – Alanna Collen (336 Pages) – This was a reread from 2018. It continues to be the best book I’ve read on the microbiome.  In terms of first principles for wellness, Collen nails it. 50% of Americans have allergies. The explosion of autism, diabetes, obesity, metabolic disease (cancer) and autoimmune disorders in recent history is unprecedented. But this isn’t happening everywhere. This explosion is contained in developed countries. More interesting, American children living in poverty are historically less likely to suffer food allergies and asthma than their wealthier counterparts. All of these illnesses seem to be growing fastest with the wealthiest groups of people. This book builds a strong case that our new lifestyle is impacting our microbiome and subsequently causing this outburst of disease. Collen also provides a solution. She shares study after study that indicate how repairing the microbiome (through probiotics or Fecal Microbial Transplants) has the capacity to improve or even reverse everything from autism to MS to diabetes. What I liked about Collen’s argument is that it doesn’t just site correlations. She’s very transparent about how the data and studies are interpreted. Everyone should read this. 

Missing Microbes – Dr. Martin Blaser (288 pages) – This book provides a crash course in the gut microbiome, digestive tract, and how both interact with our health. Despite being very thorough, it’s incredibly digestible (pun intended) for the average person. Blaser begins with the history of microbes – how the earth and all of its inhabitants evolved in conjunction with microbes. Every plant and animal at some level has chosen to skip the tiresome process of evolution for developing certain traits, and instead outsourced those jobs (e.g. digesting dairy) to microbes. Blaser then walks through how this system impacts our health and why it’s so critical. This is a great first read for anyone interested in the microbiome.

Your Brain on Porn – Gary Wilson (224 pages) – This is a great example of a book which would have been better as a blog post or magazine article.  That said, this book had 3 fascinating points: 1. Dopamine is not triggered by rewards. It’s actually triggered by the anticipation of satisfaction. Additionally, this dopamine cycle creates tolerance (you need a greater stimulus each subsequent time to elicit the same dopamine release). That’s why addicts can never get enough. 2. Neuroplasticity is the brains ability to rewire its response network based on different stimulus patterns – think Pavlov’s dogs. And 3. Human’s are pretty simplistic. Porn exploits all 3 of these points, rewiring our brains (yes, our – don’t pretend you’re innocent), and shift our reward feedback loop. My favorite study from the book was that monkeys, when given the choice, would pass on food in favor of viewing more pictures of monkey butts. (That’s us, folks…). Modern porn plays on these feedback loops and finds ways to provide greater and more extreme stimulus, ultimately diminishing our normal baseline responses and leading to depression and, lack of connection.

The Whole-Body Microbiome – Brett and Jessica Finlay (304 pages) – I picked this up after Naveen Jain recommended it. This book breaks down the different microbial systems for each area of our body (i.e. oral, heart, lung, etc.) and how our microbes dictate functionality of each organ. While the science was a bit out dated (in relative terms, it’s only a few years old), my core take aways were two fold: 1. The study and manipulation of microbes will play a major role in healthcare and disease prevention in the future, and 2. There will be a flood of consumer products launched that utilize microbes (you’re already seeing this with probiotics and skincare products). 


What Matters Most – James Hollis (288 pages) – This book dissects the great existential question: “why are we here?” Hollis examines consciousness through the lens of our innate habits and behavioral patterns. These are the mental processes that meditation and psychedelics are shown to improve.   This book had so many great one liners and concepts about the self and psyche.

  • Passion (Passio = Llatin word for suffering): “Passion is something we feel so deeply, so intensely that it hurts. Yet much of worth comes from such a hurt…”
  • “If we do not create our own myth, we will be enslaved to someone else’s.”
  • Lou Gehrig  “’They were boys in mens body’s doing what we all want to do, continue the games that boys played.’”

Rereading my notes, I kept thinking, ‘I need to reread this monthly.’

Waking Up – Sam Harris (256 pages) – This is a reread from 2016. Harris is a neuroscientist, author of numerous NYT best sellers, and a public intellectual. Here he explores spirituality and the foundational elements of religion through the lens of science and neuro-processes. I love how Harris attempts to apply studies and the scientific method to unravel a complex and dogmatic arena. Ultimately, Harris argues that there is more to understanding reality than science and secular culture generally allow, and that how we pay attention to the present moment largely determines the quality of our lives. Throughout the book he dissects religion, the use of psychedelics, meditation, and the human condition. Great read.

A New Earth – Eckhart Tolle (315 pages) – This book explores the ego, its confusion with the self, and highlights how the recognition and separation of both is the key to internal peace. Tolle begins by looking at the current state of humanity (ego-centric and reactionary), and then provides an alternative to this potentially dire situation. He outlines a practical process that includes a radical inner leap from the current egoistic consciousness to an entirely new one. If you like Ego is the EnemyLetters From a Stoic, or Waking Up, you’ll enjoy this one.

What I Talk About When I Talk About Running – Murakami Haruki (194 pages) – This was a relaxing, pre-bedtime read. Haruki’s descriptions of his mental and physical states while he runs is almost meditative. He chronicles periods of his life in the context of his running. This includes his training and completion of a will-breaking 62-mile ultramarathon, and a solo re-creation of the historic first marathon in Greece.  A good chunk of this takes place in Boston, and I got extra enjoyment out of his descriptions of running up and down the Charles river or around Cambridge. Not for everyone, but a fun, stoic-esc read.

Perennial Rereads:

The 4 Hour Work Week – Tim Ferriss (416 pages) – I read this every year from cover to cover. After numerous passes, almost all of it is highlighted or notated. We can often get bogged down in the routines of traditional work environments and how the ‘world’ operates. This book is my reset to remind me to question assumptions, test the efficacy of my procedures, and to focus on effectiveness and not efficiency – just because I do something well, doesn’t make it important. I owe this book a great deal of gratitude. During a 4 year extended health crisis when I was functional for less than 1-2 hours per day, and considering leaving my job, this book gave me the tools to become more effective, leading to several promotions, and being named Internal Wholesaler of the year.

The Third Door – Alex Banayan (320 pages) – This book quickly became an annual read. At 18, Alex skips studying for his freshman biology final to instead ‘hack’ the Price Is Right. He games his way on to the show and finds a way to win the whole thing! This story alone was incredible and hilarious. But he doesn’t stop there. He takes his winnings and goes on a quest to track down Bill Gates, Lady Gaga, and dozens more of the world’s most successful people to uncover how they broke through and launched their careers. This book reminds me what it takes to accomplish big goals, make it to the top of any field and how to do what you love.

Title Defined: There’s the First Door: the main entrance, where 99 percent of people wait in line, hoping to get in. The Second Door: the VIP entrance, where the billionaires and celebrities slip through. But what no one tells you is that there is always, always . . . the Third Door. It’s the entrance where you have to jump out of line, run down the alley, bang on the door a hundred times, crack open the window, sneak through the kitchen – there’s always a way. 

Thanks 1000 – AJ Jacobs (160 pages) – “I don’t want to get to heaven (if such a thing exists) and spend my time complaining about the volume of the harp music” – Jacobs. I loved this book last year and use it to reset my focus. AJ seeks to thank everyone who helped make his morning cup of coffee a reality. As Jacobs writes, humans are programed to spot whats wrong, dangerous or going poorly. This is because our ancestors who were overly optimistic about a sabertooth tiger’s empathy didn’t pass along many genes… But just because that’s our default setting, doesn’t mean we’re doomed to be cynical Larry Davids. We can retrain our habits, change our perception, and improve our overall happiness. Jacobs is a great and funny writer. This is a must read. 

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