Books
Required Reading for Entrepreneurs and CEOs Running Small and Medium Sized Businesses
The books that I profile below are the ones that I think are likely to be most impactful in improving some aspect of either your personal or professional life. I have read each of them personally, and have profiled only those books that I’ve rated a minimum score of 4/5. The focus here is on quality, not quantity. If you’re interested in other book ratings and reviews (including those with a rating of <4/5), you can follow my Goodreads page here.
Hover over each book (single-click on mobile) below for a brief summary and a link to purchase it on Amazon.
MANAGING YOURSELF
A very interesting and highly readable study into the idea of human happiness, a subject that impacts us all. It addresses the question of what things produce genuine and long-lasting feelings of happiness, and, just as importantly, what things do not. You are likely to learn at least a few key lessons from this book that represent things that you can quickly begin to incorporate into both your personal and professional lives.
Of any book on leadership or entrepreneurship that I've ever read, this one paints the most realistic picture of what it's truly like to lead a high growth, entrepreneurial business where easy answers are hard to come by. It is short on cliches typical of many other management books, and is written in a very direct, straight-forward, and highly readable style. This book is also a potentially great read for the spouse/friend/family member of a CEO, as it may provide them a more realistic understanding of the things that their loved one may be dealing with as a leader/entrepreneur.
THE book to read to learn more about the cognitive biases that shape our decision making processes as human beings. These (often subconscious) biases have had a very real impact on every single decision you've ever made, both personally and professionally. The best way to combat the potentially unwanted effects of these natural tendencies is to be systematically aware of them, and this is the book to read if you're looking to do so.
This highly readable book discusses the ways in which stress can be either an incredibly helpful or an incredibly destructive thing, depending on how it's approached. The book reviews both overall philosophies and tactical tools that entrepreneurs and CEOs can use to harness the power of stress while limiting its potential negative health consequences. Much of it revolves around the central concept of Stress + Rest = Growth (In short: Alternating between periods of high exertion and deliberate rest is ultimately what produces the greatest degree of both physical and intellectual growth.
Written by the Roman Emperor Marcus Aurelius, this is one of the founding books of the philosophy of Stoicism, the fundamental ideas of which remain true today, thousands of years after being originally documented. Among other things, stoics controlling their perceptions of (and reactions to) external events, avoid thoughts of the past and future in favor of the present, are part of a broader inter-connected whole, and value their own opinion over those of others. Given that the book was written around 161 to 180 AD, it requires some translation: This translation by Gregory Hayes, is by far the most digestible.
Daily meditation has grown to become perhaps THE most important and useful tool for me in managing my own psychology. The science behind the benefits of regular meditation is now very well established, and as a result, it's becoming increasingly difficult to find elite athletes, CEOs, and other higher performers who DON'T regularly meditate. This book, written by Andy Puddicome (founder of the popular meditation App Headspace - which I also use daily), is a very approachable introduction to the subject, and contains everything that you'll need to know to establish your own daily practice.
Victor Frankl, a Psychotherapist and Holocaust survivor, wrote what is among the most important books ever written in the realm of human psychology. It includes a recollection of his experience in a concentration camp, including how he and other prisoners were able to find sources of meaning and direction in an otherwise unfathomably horrible situation. Though it goes without saying that few experiences can compare to that of a prisoner in a concentration camp, this book may help you find meaning within the struggle that you're currently dealing with.
An oldie but a goodie, this book has become a timeless classic for a reason. Though we as a society and as a species have evolved technologically by orders of magnitude over the past 100+ years, psychologically we remain largely the same over that same period. In this book, Dale shares timeless lessons on how to best deal with other people to form genuine and lasting bonds. During his time earning his MBA at Columbia's Business School, Warren Buffet took Dale Carnegie's course, and to this day still refers to it as the best personal investment that he's ever made.
A great introduction to stoic philosophy written by Ryan Holiday, who is (rightly) credited with reintroducing it into the modern day. It features 365 quotes (or meditations) that are meant to be read once daily (with each quote/meditation including modern context/translation by Ryan). I'm too impatient to read 1/day, so I'd read anywhere between 5-10/day. This book can be read in bits and pieces without the loss of context, and will almost surely provide you with a few nuggets of useful stoic wisdom
The author (a gerontologist) interviewed thousands of 70, 80, and 90+ year old Americans, and recorded their most frequently cited lessons, regrets, reflections, and mistakes spanning their entire lives. The 30 most common responses were then classified into categories such as career, family, parenting, growing older, and others. Age seems to bring about a sense of wisdom, clarity and perspective that is nearly impossible to replicate, but this book does a great job at attempting to do so
Though I'm an avid reader, this is the first book that I have ever started and finished in a single day. Written by a neurosurgeon recently diagnosed with cancer (I suggest reading this with a box of tissues handy), this book explores what is truly meaningful in life, and why it's important not to defer your dreams and values to some point in the future, but instead to live them right now. Though this is the furthest thing I can imagine from a business book, everybody can benefit from the lessons contained within
Though this book has Time Management within the sub-title, it is the furthest things from the time management books that you may be used to. Instead of focusing on how to tick one more item off of your To Do list, the author uses a mix of psychology, philosophy and logic to discuss the ways in which we can make the most out of our limited time on earth (if you live to the age of 80, you have only 4,000 weeks in your entire life). This book has been among my most enjoyable reads over the past few years
As an almanack (essentially a collection of transcriptions from podcast interviews, tweets, blog posts, and other disparate sources) this admittedly is unlikely to win a Pulitzer for writing, but the wisdom contained within makes this book worthy of a read (likely several re-reads). Though Naval Ravikant is known for being a successful entrepreneur, CEO, and angel investor, he is arguably better known for his philosophies on life, wealth, happiness and success
If one were to implement an "operating system" to govern the actions, decisions, and interpretations that govern their lives, they could do a lot worse than implementing the stoic philosophy. Though author Ryan Holiday is rightly credited for re-introducing stoicism into the modern age, I found that author William Irvine did a great job communicating the basics of stoicism in this highly digestible book.
One of the foundational books behind the now widely practiced Cognitive Behavioural Therapy (CBT), this book contains more tactical tools than any other that I've read, specifically for those who experience anxiety. Though it sounds odd to compliment a book by suggesting that it reads like a textbook, this does, though in the best possible way. But this is no light bedtime read: Get the pens and highlighters ready, as it's heavy on exercises.
MANAGING YOUR BUSINESS
This book is all about sales, and specifically around how to optimally structure a sales team across the various functions (new accounts, existing customers, lead generation, incoming leads, sales ops, etc.). Most of what it preaches has grown to become widely adopted for good reason. This is a quick and easy read, and gets quite tactical in the best possible way. Specifically if you're building out a sales function from a relatively nascent state, this is a book you'll want to check out.
I love this book. It is about as practical and useful as a business book gets, and unsurprisingly, it was written by a SMB CEO. It covers a wide array of topics from cash management, to personnel management, to profit optimization strategies, and everything in between. This book scores a 0/10 on useless theory (in this case, 0/10 is a good score), and a 10/10 on specific, practical, tactical tools and strategies that you'll be able to implement in your own business a few days after you finish reading it. I wish more business books were written like this!
This is the best book ever written on the subject of technological disruption. Indeed, this is the book that coined the term 'disruption', which unfortunately is often used today well outside of its original meaning. Whether you're facing a competitive threat to your own business, or are looking to become a competitive threat for an incumbent provider, this book is required reading.
If you have an otherwise talented and motivated group of people who are not working well together as a team, then this book is a must-read. Patrick Lencioni is one of the few authors of which I'm aware who manages to make a business book read like an entertaining work of fiction (he calls this distinctive style a "leadership fable"). The result is a quick and easy read that is BIG on impact. He discusses the primary reasons why teams sometimes fail, starting at the root problems and working his way up to more symptomatic issues.
Another gem from Patrick Lencioni, and another "leadership fable" that will ensure that you're as entertained as you are educated. One of the biggest challenges that many CEOs face is deciding how and where to best spend their time. In this book, Patrick argues that there are four critical areas that each represent the highest and best use of a CEO's time. If you're wondering whether or not you're expending your resources in the most efficient way possible, this book will provide you with the clarity that you seek
It would be no exaggeration to say that this book changed both myself and my company more than any other book that I've ever read. In "Traction", Gino Wickman walks through an "Operating System" that SMBs can employ to guide the planning, execution, and measurement that's required to run a high performing SMB. Even if you choose not to implement the operating system that he discusses within, it is impossible to read this book and not come away with hugely meaningful insights. 10/10 on practicality, usefulness, and specificity. No fluff or filler here.
This book is all about the CEO as chief capital allocator. Among other things, it presents a strong case around why and how capital allocation is among the CEO's most important skills and duties, and does so through 8 unique case studies. This book takes a close look at each potential use of capital, and evaluates how 8 high performing CEOs have used these tools with a level of mastery that continues to be unsurpassed by their peers. It's been said that the CEO's three main duties are 1) Culture; 2) Vision, Mission & Strategy; & 3) Capital Allocation. This is the book to read if you're looking to master critical skill #3.
Similar in spirit to "Traction" by Gino Wickman, The Rockefeller Habits by Verne Harnish is an incredible book dedicated specifically towards SMB CEOs. Like Traction, it advocates for the use of a formal "Operating System" to guide the planning, execution, communication and measurement necessary to successfully run a high-growth SMB. In addition to being a leading author, Verne is also the founder of EO, one of the world's largest peer networks for SMB CEOs. If you like this book, check out his other book called "Scaling Up".
This is THE book on effective hiring processes. Whether you are hiring 1 person or 100 people this year, you must read this book. The authors introduce, among other things, the "Topgrading interview", a very specific interview style and format that produced very effective results for me (among countless others) when I used it during my own CEO tenure. It is very practical, and introduces several tools that you can implement in your own business shortly after reading it. If you read just one book on hiring, make sure it's this one.
The Four Disciplines of Execution (or 4DX) is the best book on corporate goal setting and execution that I've ever come across. We implemented their program within our own business, and I would happily do the same if given another opportunity to do so. For those who are so inclined, they also offer trained personnel who can work with your company to actually implement these best practices alongside your management team and employees. We also utilized this service, and again, I would personally recommend it.
Though this book is written about what is now one of the world's largest companies (Amazon), contained within are countless valuable lessons and tools that SMB CEOs can implement within their own businesses. Among particular interest to me were the concepts of "single threaded leadership", the "six pager", "Measuring inputs, not outputs", and "starting with the end customer experience in mind". This book is as entertaining as it is informative
This book is a classic for a reason. While it is slightly more academic and slightly less tactical than many of the other books that I profile on this page, it is a must-read nonetheless. 10+ years after initially reading it, I still find myself referencing concepts that I first learned in this book, including "The Flywheel", "The Level 5 Leader", and "First Who, Then What".
Though this book is all about the dynamics between startup founders and their Venture Capital backers, many (though not all) of the concepts and debates contained within can also apply to the relationships between searchers and their investors. More specifically, the importance of selecting your investors carefully, the value of long-term personal relationships, the essential nature of trust, and the importance of the various legal terms governing the relationship. Most importantly though, it's just a very fun and entertaining read!
OTHER
Though the books in this category tend to offer fewer tactical tools and practices to implement within your own life or business, I’ve thoroughly enjoyed each of them nonetheless. Some for pure entertainment value, others for the broader, thematic lessons that I’ve been able to extract.
Read mostly for entertainment value, but contained within are some lessons around a) the power of competition in soliciting bids; b) the costs of greed and hubris; c) the realities of using too much leverage; d) when anchoring, emotions, sunk cost fallacy, commitment bias, and other psychological biases overtake economic realities as the primary reasons for action
Read mostly for entertainment value, but contained within are some lessons around a) The danger of "unknown unknowns", b) the dangers of excessive greed, hubris, and leverage; c) the power of telling a good story; d) how economic shocks can come at any time and for any reason; e) when practice differs substantially from theory
Alongside "Security Analysis", The Intelligent Investor is essentially seen as the bible of value investors (in fact, they are jokingly referred to as the old testament and new testaments, respectively. Though it's written largely in the context of investing in public equities, countless principles contained within can also be applied to investing in substantially any company, be it public or private.
One of the business leaders for whom I have the most admiration and respect is Jamie Dimon of JPMorgan Chase. Not only is he incredibly intelligent, articulate, dedicated, and thoughtful, but he takes his responsibilities as a leader very seriously. As far as I'm aware, this is the best biography on him that's available.
You probably don't need me to tell you that this is one of the most infamous and most widely read biographies of a CEO and Entrepreneur that has ever been written. In many respects, Steve Jobs was in a league of his own, and today continues to be revered by technologists, historians, entrepreneurs, journalists, and CEOs alike across the globe. This is the definitive biography of this complicated, creative, and relentlessly driven man.
The public's fascination with Elon Musk seems to know no end, and for good reason. Though much (perhaps too much?) has been written about his tweets, product announcements, and public disputes (not to mention the stock price of his car company), this biography is the best one available for the thoughtful reader who wants to go beyond the clickbait headlines to learn more about what makes this incredible entrepreneur tick.
In addition to simply being very well written, Bob Iger's book provided an interesting window into how problems and opportunities facing companies as large as Disney are, in many respects, the same problems and opportunities that face companies a fraction of its size: Culture, focus, strategy, incentives, communication, and negotiations (among others) indeed transcend companies of all shapes and sizes.
Ray Kroc's story demonstrates the simple values of passion, enthusiasm and hustle, more than most others of which I'm aware. It may be of particular interest to later-career entrepreneurs/CEOs, as Ray Kroc's journey as the man who went on to build McDonalds started at the age of 52. Moreover, it may be of interest to entrepreneurs with sales backgrounds, as Ray spent the majority of his career prior to McDonalds as, of all things, a Milkshake salesman.
Many people are familiar with Warren Buffet's story, given his standing as one of the greatest investors and business builders of all time. However, of all accounts of his life and career, in my opinion this one is the best. It's a long read, but worth the time. Perhaps more than any other lesson, this book left me with a simple truth: Do what you love. Everything else will likely follow.
This book holds its own on pure entertainment value alone, though also serves as a cautionary tale for investors about the importance of independent thinking and investing within one's sphere of competence, and avoiding the temptation to follow the heard. It also challenges entrepreneurs to consider the cost of untethered levels of vision and ambition. Lastly, it acts as a cautionary corporate governance tale: You won't believe what Board's let founders get away with in markets in which attracting great founders has become increasingly competitive.
The money management book for people who hate money management books. This eminently readable book takes an otherwise dry topic and brings it to life through the use of stories, psychology, philosophy, and real-world personal experience. This book is less about investing and more about our broader relationship with money, including how we earn it, spend it, save it, and invest it. Those with and without formal training and financing and investing will enjoy this book all the same.
This was a fantastic book that documented the rise and fall of BlackBerry, the company that effectively invented the smartphone. In addition to being simply entertaining and well written, within the book are countless lessons related to technology, hubris, partnership dynamics, competitive threats, and the personal and professional realities of being an entrepreneur, among many other things.
An incredibly well-written book on the virtues and vices of arguably the most important entrepreneur of the 21st century. The very things that haunt him also appear to be the same things that drive him. This is one of a very small number of books that actually ought to be 600+ pages. Both his supporters and detractors would be well-served by reading this.