8 Must Read Books:
Title: Hot Seat: The Startup CEO Guidebook
Author: Dan Shapiro
Description: Shapiro mixes first-hand Startup CEO experiences with the experiences of other Startup CEOs he has interviewed. He created a masterfully crafted and very practical book that every Startup CEO should read. He covers almost all the topics you would want insights on: decision-making, delegation, raising money, and more.
Why you should read this book: I like it because it is an easy read and very practical. You won’t find fluff or bloviating or puffed up personal drama. It’s a straight forward book that packs a lot of learning. I recommend it to everyone.
Title: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
Author: Ben Horowitz
Description: Horowitz is well known as one of the leaders of VC firm Andreessen Horowitz. He chronicles his leadership lessons from the many high profile companies he led. MANY of the Founding CEOs that I have interviewed have read the book. The reason? It’s an unvarnished, in-your-face account of entrepreneurial leadership that really makes you question whether or not you should take the leap. It’s that good. 🙂
Why you should read this book: If you want an account of what struggle looks like, you should read this book. Ben seems to have experienced almost everything a Startup CEO can experience. But, it’s his personal feelings about the ups and downs and the practical advice he shares that makes this book a must read.
The Stages of Your Development
Title: Leading at the Speed of Growth: Journey from Entrepreneur to CEO
Authors: Katherine Catlin, Jana Matthews
Description: Catlin and Matthews wrote an immensely helpful book that helps you predict the issues your business faces and the changes you should consider as you and the company grow.
Why you should read this book: This is basically a leadership development plan written specifically for Startup CEOs and leaders of fast-growth companies. It’s practical and will help you anticipate the somewhat predictable pitfalls and opportunities you will face as a growth company leader. Plus, you’ll love the vignettes that will have you saying to yourself, “Hey, I though the same thing” or “that happened to me.”
Title: The Founder’s Dilemmas: Anticipating and Avoiding the Pitfalls That Can Sink a Startup
Author: Noam Wasserman
Description: This research based book captures many of the common dilemmas that Founding CEOs encounter as their journey to CEO. Noam Wasserman reveals these common pitfalls and decision points in a way that is easy to read and relatable in many ways.
Why you should read this book: I like Noam’s book because he has condensed his research into a practical flow chart of issues that most Founding CEOs face. You can literally keep it on your book shelf and refer to it every other month and find your next dilemma and advice on how to navigate the dilemma. Several of my coaching clients have read it and attest to its profound impact on their lives – most through better, more informed decisions.
Title: Startup CEO: A Field Guide to Scaling Up Your Business
Author: Matt Blumberg
Description: Blumberg has created one of the most detailed reference guides on Founding CEO leadership on the market. He covers more topics than any of the other books. He offers valuable insights into how the CEO sets the overall vision and strategy of the company and communicates it to all stakeholders. He discusses how to build a company’s human capital by recruiting, hiring, and retaining the very best talent. He examines how a CEO must align available resources with the company’s strategy in order to ensure success. And, there is a lot more than these topics.
Why you should read this book: This is not necessarily the type of book that you read cover to cover in one sitting. It is rich, dense, and packed full of very specific tips on an array of topics. My guess it that would be a great reference guide when you are struggling with a certain topic. Pull it off your shelf and chances are Matt has some great advice for you.
Title: Startup Leadership: How Savvy Entrepreneurs Turn Their Ideas Into Successful Enterprises
Author: Derek Lidow
Description: Lidow’s experience as a Startup CEO and his time as a Princeton University professor combine to create a wonderful resource. The best part of the book are the actions he believes you should take at the key developmental phases of your business. It’s heavy on processes and light on sentiment. But, he clearly delineates what you need to do as a leader during each phase your business goes through. I think this aspect of the book is very insightful and helpful.
Why you should read this book: If you have no idea how you should be spending your time, this is a great book for you as a Founding CEO. Derek breaks it down very clearly and I believe makes a great case for understanding the processes inherent in Startup CEO leadership.
Title: The CEO Tightrope: How to Master the Balancing Act of a Successful CEO
Author: Joel Trammel
Description: Joel has an amazing track record of success as a Founding CEO. His analogy of a tightrope that a CEO must balance on is a great image to keep in mind. He covers many topics and angles that are not often covered. For example, I like his chapters on decision making and how it relates to building consensus.
Why you should read this book: It’s a well written book with some unique angles on Founding CEO leadership that you will appreciate. I also think his style of writing is well suited for a weekend read or a flight across the country.
Title: Lost and Founder: A Painfully Honest Field Guide to the Startup World
Author: Rand Fishkin
Description: Rand details his very personal journey from Founder to CEO while also weaving in his hard earned wisdom about being a Founder and Leader.
Why you should read this book: This is an intensely personal book. Rand writes candidly about his financial struggles, his health struggles, his family health struggles, and his leadership struggles. And, we don’t often hear Founders talk about the details of why they stepped down as CEO or why they may have left the company they founded. Rand even shares about this with grace. You will learn a lot about how to handle the inevitable challenges of being a founder. But, you will also learn how to be a better person.
4 More Great Books:
Title: Virtual Freedom: How to Work with Virtual Staff to Buy More Time, Become More Productive, and Build Your Dream Business
Author: Chris Ducker
Description: Ducker does a great job helping every leader learn how achieve virtual freedom by sharing the secrets of using a virtual assistant. He should know. He founded and leads Virtual Staff Finder, the number one provider of dedicated, experienced, Filipino virtual assistants.
Why you should read this book: One of the top issues I hear from Founding CEOs is delegation. How can you leverage yourself more effectively? Chris Ducker maps the ins and outs of working with a virtual assistant with skill and ease. He covers it all in this book. If you really want to grow the company you founded, Chris’ book will help you understand what successful leaders have done for quite some time. Delegate the things that others are more suited to care of.
Title: A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas
Author: Warren Berger
Description: Berger nicely mixes history, psychology, education, and practical business research and stories to convince the reader that we don’t effectively use the single biggest impetus to change: better questions. He writes about the impact of questions, why we slowly stop asking questions, a template for innovative questioning, and using effective questions in business.
Why you should read this book: As a Co-founder & CEO I have learned that many of us struggle with using the power of questions to enhance our effectiveness as CEO. This book is important as a mindset shaping tool. After reading it, you will be convinced that asking better and “more beautiful” questions is the single biggest action you can take to enhance the success of your organization. In fact, as an executive coach to Founder & CEOs, I spend most of my time helping CEOs simply to shift from spending their days making statements to asking questions. NOTE: if you don’t have time to read the entire book, skip to Chapter 4 and read “Questioning in Business.”
Title: The Five Temptations of a CEO, Anniversary Edition: A Leadership Fable
Author: Patrick Lencioni
Description: This is a business fable book, which makes it a quick read. But, don’t be fooled by its simplicity. Lencioni focuses on five “traps” that he (and I) often see CEOs descend into. In fact, these five areas come up frequently in my executive coaching practice. Yet, Lencioni just doesn’t talk about what to avoid, through the interesting story, he also shows you what a CEO should focus on and how these five focus areas connect to each other.
Why you should read this book: This is a my go-to book for new CEOs to build a quick foundation of key thoughts about their leadership as CEO. There are hundreds of leadership books on the market. But, I keep coming back to this one for new StartUp CEOs because it is a fast way to question yourself about who you are as a leader and decide if you are well positioned to build on your early successes.
Back To Basics
Title: The SPEED of Trust: The One Thing That Changes Everything
Authors: Stephen R. Covey and Rebecca R. Merrill
Description: Stephen R. Covey is the son of the very well known Stephen M. Covey who wrote the book “The Seven Habits of Highly Effective People.” “The Speed of Trust” makes it VERY practical for you to consider whether or not you know how to build trust with the people in your company. The authors use the metaphor of a tree to break down trust into easily understandable parts that will help you take the often amorphous and intangible topic of trust and turn it into action.
Why you should read this book: You should definitely read this book if you struggle with wrapping your arms around just what trust is all about and how it affects the success of your business (and certainly your life). But, I think there is a much more practical use of this book. I use it with clients to help them immediately assess their “trust meter” with the people on their team. Using a scale of 1-5, when you rate team members, for example, on Integrity, Intent, Capabilities, and Results, you get an instant insight into your perceptions about the capacity of your team members to positively influence the success of the company you founded or co-founded. My clients tell me all the time that they love the book, this assessment exercise, and the model that Covey and Merrill use.
Disclosure: Please note that some of the links on this page are affiliate links, and at no additional cost to you, I will earn a commission if you decide to make a purchase. Please understand that I have experience with all of these resources, and I recommend them because they are helpful and useful, not because of the small commissions I make if you decide to buy something. Please do not spend any money on these resources unless you feel you need them or that they will help you achieve your goals.