Recommended Books for Entrepreneurs

Our team shares very specific books and articles with the founders we advise and especially the ones that we invest in. We maintain an online library with the articles and grant access to our founders so that they can read them at their own leisure.

The books we currently recommend are listed here with a breakdown as to why we recommend them. Our team hopes that you find this useful. The first 5 books are in a specific order because we firmly believe that first a founder must have the right mindset, then have clarity of purpose, then learn to influence people to support them.

Only after that should they try to figure out what kind of organization to build. Purpose and passion is what will get you through the inevitable dips, over the humps, around the obstacles and out the other side, with enthusiasm.

Doing it only for money or fame will not work out well in the long-run. After that, you need to make a plan and know the destination. The path will change, many time, but keep your eyes on the prize. Finally, never forget the importance of family and friends. If, and when, you have a failure, they are the ones who will not look at you differently. They will still love you. Ignore everyone else because they only like you when you are up and toss you aside when you are down.

How Will You Measure Your Life

The right mindset requires that you make a conscious effort to know how you will ultimately measure your life. Do not use society’s measurements of success. Develop your own so that you will be happy with yourself.

Find Your Why

After you have the right mindset, it becomes easier to find your purpose, why you do what you do. People buy into that, not just the product or the team.

The Art of the Start and Enchantment

Guy Kawasaki’s book is the most straightforward, no bullshit book about actually starting your business and stop talking about it. Buy it, study it, keep going back to it and share it with others. Enchantment is all about delighting people, which then makes you happy and helps you to be more successful.

How To Win Friends and Influence People 

A standard issue for most successful people, almost to the point of being cliché but still a good read and valuable insights. We recommend reading the summaries before major meetings because it reminds a person about what is really important if you want to win over someone, especially a potential investor, strategic partner, customer or new advisor.

Good To Great and Built To Last 

Both these books are extremely useful to understand how to find your “Hedgehog concept” and how even successful companies fail. Learn from the mistakes of others so that you can make new mistakes, not repeat old ones. It also gets entrepreneurs to think big — Big Hairy Audacious Goals.

Blue Ocean Strategy

Competition is not a bad thing but you can learn from Nintendo choosing not to compete with Microsoft and Sony by launching the Wii. You do not have to go head-to-head but can instead think differently like Apple.

Losing My Virginity

Richard Branson has always been a rule-breaker but he has been through some very tough times. Learn from his mistakes and how he overcame them in order to know what real entrepreneurship is going to be like.

The Toilet Paper Entrepreneur and The Pumpkin Plan and Profit First

Mike Michalowicz is a close friend of mine and he asked me to endorse his first book, alongside Donny Deutsch from CNCB’s The Big Idea at the time. We brought him to Jamaica to speak and he delivered! The book had been so integral to my thinking about focusing on the destination and not obsessing over the path because it will change, tacking like a sail boat. 

The Pumpkin Plan built on those lessons by actually helping founders to plan for success. Profit First is applicable to all the companies NOT trying to follow the Silicon Valley model of high growth, profits-be-damned approach to building a business. Few companies are ideal for VC money so Profit First is the most appropriate book for founders.

Built To Sell

Your end goal may not be to sell your company but if you follow the plans in this book then you will build a company that has a solid team and solid processes. Many of the companies that make the Inc. 500 each year are following these kinds of processes and processes are framework you build a sustainable business on. Start thinking about them from early.

The New Rules of Marketing and PR

David Meerman Scott changed my life with this book because it really opened my eyes to the power of brand-building and getting media outlets to come to me instead of having to constantly pitch them.

F’d Companies

If you are running a tech company, this is a must-read, especially for those Gen Y and later entrepreneurs who were not around for the bursting of the Dot Com bubble. What’s old is new again so study history and do not repeat it.

Decoding Silicon Valley

Michelle Messina is an advisor to our fund and personal friend of mine ever since we sponsored Ingrid Riley’s Caribbean Beta event in Kingston, Jamaica many years ago and covered the costs of bringing Michelle down for the event. Her book with Jonathan Baer gives amazing insight into how the VC world works and helps founders determine if they are a good fit for that world or not, and if so, how to navigate it and what to actually expect. 

Upstarts!

Donna Fenn was a senior editor at Inc. magazine when she wrote this book. I am in the book but I was blown away with the inspirational stories of fellow Gen Y entrepreneurs who were attempting big hairy audacious goals. If you want to be inspired, read this book!

Steal Like An Artist

Research Apple and Xerox Parc, Microsoft Windows 95 and Apple’s Mac Os or look at Yahoo vs Google, Uber vs Lyft and so many more. Can you build a better mousetrap? Can you differentiate yourself?

The Subtle Art of Not Giving a F*ck

Entrepreneurship attracts haters and naysayers. You can take their criticisms under consideration but do not let them direct your plans if they are not your target market. Just dust your shoulders off like Jay-Z says.

Delivering Happiness

The culture of the company you build will either be helpful or harmful in the long-term. Read this to build the right kind of company culture.

Measure What Matters

My MBA program at the University of Miami taught me all about KPIs — Key Performance Indicators. I now know that the better focus is on OKRs — Objectives and Key Results. KPIs only form part of the picture and fit into OKRs. Learn from what Intel and Google used to get where they are.

Steve Jobs

Walter Isaacson’s book about Jobs gives such an in-depth breakdown of the decision-making process of Jobs, Apple, Pixar, his mistakes, flaws and genius. Jobs was not the ideal manager but his abrasiveness is clearly explained. Learn what to do and not to do, understand what it takes to think differently and have a global impact. Learn from his life and live your own full one, recognizing when you are straying from your own beliefs. Become a better person.

Execution

At the end of the day, ideas are with nothing. Execution is what matters. Get shit done.

The 17 Indisputable Laws of Teamwork

You cannot build a great company (or NGO) without a solid team. That means becoming a good leader. That takes deliberate effort. John C. Maxwell is certainly the king of the hill on leadership.

Screw Business Usual

Business cannot only be about profits. Branson’s approach to a different kind of capitalism, one that focuses on stakeholders and not just shareholders. We do not invest in people who do not share this triple-bottom-line approach to business.

40 Chances

Howard Buffett, son of Warren Buffett, shares the life of a farmer with 40 crops. Insightful read about the chances you will get.

These are the current books we recommend and we are reading more this year to discuss with our team, including Blitzscaling by Reid Hoffman being high priority.

We hope that this list is helpful to you.