The Top 5 Books Every Startup Owner Approaching 50 Should Read

The Top 5 Books Every Startup Owner Approaching 50 Should Read. I have read a lot of books while setting up my own business as a man approaching fifty. I like to read (almost as much as I love to write) and the best business books can help to think about your business in a different way. In my opinion, business books can all have lessons for the budding startup – they don’t have to be specifically aimed at the startup market to be relevant. If you know your business (and who else knows it better?) then you can see ideas in loads of different place that will help you to formulate plans for your own business. Here is my guide to the top 5 books every startup owner should read –

The Cluetrain Manifesto

This book is several years old now, but I love the tone that it creates and the way that it looks at business as something that can be collaborated on and developed.[( The Cluetrain Manifesto: The End of Business as Usual (Tenth Anniversary) By Levine, Rick ( Author ) Paperback Apr – 2011)] Paperback is something that all startup owners should read because it helps you to understand the way that business is done in the modern day, even though the book itself is fast heading for its 20th anniversary

Some ideas in business never go offside. I will admit that some of the ideas in this book didn’t even get off the ground, but the sentiment in there in every successful business. You come away from reading this book with a smile on your face and a spring on your step.

The Top 5 Books Every Startup Owner Approaching 50 Should Read

The Starfish and the Spider

This is another book that has a few miles under its belt. But will help you to look at your business in a completely different way. It helps you to understand the power of the consumer. And to think about your target market. are you selling them something that can be easily undermined by another offer? The Starfish and the Spider: The Unstoppable Power of Leaderless Organizations is another book that makes you think about the world your startup lives in and how you can make the most of opportunities.


This book is easy to read, gives great advice and keeps it light. The whole ethos of the book is to make things as easy as possible for you to run a business. Think about cutting out all the unnecessary stuff that doesn’t add value to you and your startup. You don’t need to surround yourself with more and more feed tape. One of the benefits of being a startup is that you are light and agile – don’t throw that advantage away. ReWork: Change the Way You Work Forever lets you think about your startup and become leaner. It is set out in small chapters, that are easy to digest and each contain something interesting and thought-provoking. I love this book!

Brilliant Freelancer

I have read a few of the ‘Brilliant…’ series of books and I always enjoy the way that they pull together the necessary information about their topic. I am a freelancer – that is my business, so I found this essential reading in my quest to become better at what I do. As you break down the chapters and read through, the book gives you action points and areas to concentrate on. I even used many of the ideas from this book in one of my own, which is called
Brilliant Freelancer: Discover the power of your own success (Freelance/Freelancing) (Brilliant Business)


This is an ideal starting point for any freelance startup owner. It lets you develop your own ideas in a constructive way.

Permission Marketing

This book switched me on to Seth Godin and his ideas about the world. Marketing is a necessary part of any startup business, so you have to understand it well and get it right. I would say that this book has spawned thousands of new businesses on the basis of the way they market. The guy knows business inside out and can be followed on his blog and social media too.

I recommend that you probably work your way up to Permission Marketing: Turning Strangers Into Friends And Friends Into Customers after reading some of the others on this list. This isn’t because it is more developed. But because it will put all the others in a different light. This is my idea of the top 5 books every startup owner approaching 50 should read, but I’m sure you have your own. Let me know in the comments box what your favourite business books as a startup owner are. It would be great to hear from you.

Tags: ,
Reaching the ripe old age of 44 has got me thinking about the next milestone birthday - the Big Five-O! I share with you my experiences of what these years mean to me. Thanks for stopping by!

Related Article