Five Must Read Books On Entrepreneurship

“If I read a book that cost me $20 and I get one good idea, I’ve gotten one of the greatest bargains of all time.”  – Tom Peters

I am a sucker for cheesy and motivational business books and you can usually find me reading one (even on the beach). If I had to whittle my list of favorite business books down to just five selections that I would recommend to someone who is thinking about going out on their own and starting a business – these would hands down be the books that would make the cut. Warning – these books may make you want to quit your day job!! (The titles are affiliate hyperlinks if you want to check out their Amazon pages)

The Four Hour Work Week

The oddly titled book by controversial Silicon Valley personality Tim Ferriss (check out his blog here for some pretty interesting reading) is probably one of my favorite books of all time. I would say this book factored tremendously not only in my decision to ultimately leave my Wall Street job for more entrepreneurial pursuits but also in my own decision to write a book.  That said, take this book with a grain of salt. I think the message of the book is amazing – some of the concrete tips that Tim offers in the book are not entirely practical – but the framework that Tim uses to think about business and life is tremendously useful.

Tim’s biggest strength is his ability to think outside of the box. He really has an ability to see through all the preconceived notions and ideas that many people take for granted and turn them completely on their head.  Start with this book because it will get you fired up to really do something awesome – but after that are you going to need a little bit more substance.

The Personal MBA

This book is the meat and potatoes you’re gonna want after reading 4HWW.  Josh Kaufman absolutely crushes the fundamentals of business. Designed to be concise and information packed – this book tackles nearly every aspect of starting and running a business with amazing clarity. Josh read over 100 contemporary business books and synthesized them all into The Personal MBA. If you know nothing about business or think you know everything – I guarantee you will learn a tremendous amount from reading this.

This is the kind of book that you will want to keep in your bag because you keep taking it out and referencing different sections. This book focuses on teaching what Charlie Munger calls “mental models” – or “useful ways of thinking about the world that you can use to your advantage in a wide variety of situations” – giving you an arsenal of tools to tackle many different entrepreneurial problems.

The E-Myth Revisited

Michael Gerber draws on many of the themes from Personal MBA but really ties together the core of systematizing and documenting your business. The book is very straightforward and easy to follow because the core lessons follow the narrative of a fictional pie shop’s journey from disorganization to success. I’ve personally used dozens of the specific examples and lessons from this book to organize and streamline the operations of a mismanaged business. E-Myth combined with Personal MBA will give you a great foundation of business and operational knowledge to get you going.


Mindset is the kind of book that will get you fired up to do absolutely anything. The crux of the book is that people fall into two camps – “fixed mindset” and “growth mindset” – and if you happen to be a fixed mindset thinker (I was in a lot of ways) – switching to the growth mindset can open up huge amount of opportunity for you. Mrs. Dweck delves pretty deep into the psychological foundation for which mindset you might find yourself in – but to sum up the basic tenants of the book:

“In the world of fixed traits – success is about proving you’re smart or talented. Validating yourself. In the [world of growth] – the world of changing qualities – it’s about stretching yourself to learn something new.”

Not trying to go quote crazy here but (I should probably write a whole post on this…) this quote defines how I thought about risk, success, and failure in many areas of my life before I read this book.

“Everything I was going through boiled down to fear. Fear of trying and failing… Nothing is harder than saying ‘I gave it my all and it wasn’t good enough.’ The idea of trying and still failing – of leaving yourself without excuses is the worst fear within the fixed mindset.”

“Instead of trying to learn from and repair their failures people with the fixed mindset may simply try to repair their self esteem… by assigning blame or making excuses.”

It’s impossible to learn from your mistakes if you deny them by blaming something else.

I will say – the one drawbook of this book is that it gets pretty repetitive towards the end – repeating the same lesson in several different contexts (business, parenting, sports etc) but the message is so powerful in my opinion that it outweighs the repetitiveness.

The Monk and The Riddle

“Imagine I have an Egg” – Mr Wizdom cups an imaginary egg in his hand –“and I want to drop this egg three feet without breaking it. How would I do that?”

If one book will push you over the edge and really give you the drive to strike out on your own – it would be this. A great (and quick) read about leadership, success, business, and life – this book is eerily timely in today’s technology world. Written and set in a pre dotcom bubble Silicon Valley – this book follows the fictional journey of and the not-so-fictional life of its author Randy Komisar.

“Instead of managing business risk to minimize or avoid failure, the focus here is on maximizing success… failure is an unavoidable part of the search for success. Silicon Valley does not punish business failure. It punishes stupidity, laziness, and dishonesty. Failure is inevitable if you are trying to invent the future.”

It’s really a book that makes you ask – “What do I want to do with my life?” – and forces you to think long and hard about the answer. This book is 90% inspiration 10% information – but it will fill you with the fire to take a risk, take charge of your life – and make it what you want it to be.  The quote I put at the beginning is the riddle – don’t try to answer it now. You have to sit with the riddle for a while and the answer will simply come to you.

Fail Better

I recently read The Four Hour Work Week by Tim Ferriss and the book really opened my eyes. I’ve always been interested in entrepreneurship and the idea of founding my own business. Tim’s book really takes these ideas to the next level and provides concrete and actionable steps to do exactly that.

So I have decided to stop sitting on the couch and floating the vague concept of “I want to found a business” and doing something real. What’s the worst case scenario? Failure? If there’s one thing I’ve learned from reading the books and blogs of successful business people and entrepreneurs it’s that failure is inevitable and nothing to be afraid of. At the end of the day – failure is nothing more than a learning experience.

I read an awesome quote yesterday that sums this logic up perfectly. Adam Horowitz is an 18 year kid old who made $1.5 million within the first three day of launching his product Mobile Monopoly. His outlook on failure“I’ve failed at least 30 times with different websites and stuff… But, if I hadn’t failed all of those times, I wouldn’t be where I’m at now.”

With the ease of web design, online advertising, and micro-testing, it costs very little to float my ideas and products out there to see if any of them will succeed, but the upside is massive.  I am determined to develop a successful web-based product, not only for the supplemental income, but also to prove to myself that I can do it. Here’s to failure.