9 Books Every Aspiring Entrepreneur Should Read

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Many people dream of downing tools and saying ‘goodbye’ to the weekly grind, yet few ever make the successful transition from corporate servitude to entrepreneurial freedom. For every breakthrough startup that disrupts, changes and ripples, there are hundreds of thousands more that barely make it past inception; so, what’s the difference between those that make it and those that don’t?

In many cases, the answer is fairly obvious: there is a noticeable lack of preparation. But that doesn’t necessarily mean a failure to understand various business, financial or marketing concepts. Rather, it means that many aspiring entrepreneurs don’t comprehend the mindset and philosophy of what it takes to go it alone.

Luckily, there are literally thousands of books on this very subject, designed to prepare and inform before you take the dreaded plunge, and we’ve conveniently cut the list down to nine of the most important.

So, if you’re a total beginner, prepare to start your learning journey: these are the nine best books of all time that every aspiring entrepreneur should read.

1. The 4-Hour Workweek (Tim Ferriss)

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Any self-respecting entrepreneur’s bookshelf contains a copy of The 4-Hour Workweek, Tim Ferriss’s seminal and best-selling introduction to the modern concept of being your own boss. Originally published in 2007 and accompanied by a loyally-followed (and still active) blog, it is based on Ferriss’s own experiences of running a sports nutrition company while on sabbatical and advocates a form of antidote to the workaholic lifestyle.

Although the intricacies of entrepreneurism have undoubtedly evolved since, The 4-Hour Workweek remains a notable starting point in why so many of us seek to escape the constraints of the rat race. The 1.35 million people who have since bought a copy clearly agree.

2. The New Business Road Test (John Mullins)

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Newly updated for 2018, The New Business Road Test is exactly what it says on the tin: an exploration of whether or not that lightbulb above your head can translate into a viable and profitable business model. Written by Stanford MBA graduate John Mullins, the message is less ‘you can do it!’ and more ‘should you do it?’, a sentiment that represents an important reality check in a motivation-heavy market.

Meanwhile, Pat Flynn’s Will it Fly? offers an alternative take on the same theme; as the author himself states: ‘a lack of proper validation kills more businesses than anything else’. If you want to avoid the same fate, these are good places to start.

3. When to Jump (Mike Lewis)

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On the surface of it, the primary appeal of When to Jump might lie in the identity of its foreword contributor, Facebook COO Sheryl Sandberg. The meat on the bones, though, is the variety of characters and stories that appear along the way, as Lewis – a former Bain consultant turned professional squash player – provides the testimonies of over 40 ‘average Joes’ who all ‘jumped’ at one point or another.

For those who would class themselves at the ‘considering it’ stage of the entrepreneurial process, this is not just inspired reading, but essential, too.

4. The $100 Startup (Chris Guillebeau)

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Another title that can be considered required reading for beginners everywhere, The $100 Startup emphasises that, in the digital age, creativity is a far more important tool than finance. The real crux of its success, though (to date, it’s sold over 300,000 copies), is in its practicality. Guillebeau provides an actionable and easy-to-follow roadmap of how to start a business from scratch, armed only with a positive attitude and the aforementioned eponymous $100.

He isn’t the only one downplaying the importance of finance, either; if you require further reading, Daymond John’s The Power of Broke offers numerous tips on how to proceed with your business idea when purse strings are tight.

5. The Hard Thing about Hard Things (Ben Horowitz)

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When a book about entrepreneurism is being read and actively endorsed by Mark Zuckerberg and Larry Page, then it’s probably a good idea to see what all the fuss is about. Enter Ben Horowitz, a fellow Silicon Valley CEO who is keen to remind everyone that after the initial excitement of setting up your business comes a process that is far more difficult and demanding: actually running it.

This means learning how to overcome office politics, finetuning your recruitment policy and, yes, firing people that you like – tasks, as the title suggests, that are not particularly fun. Readers will have a hugely resourceful reference point, though; The Hard Thing about Hard Things is honest to the point of brutal, and it’s all the more valuable for it.

6. Rework (Jason Fried and David Heinemeier Hansson)

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Conventional wisdom suggests that, before starting a business, you should research your competitors, study the market conditions and construct an actionable and in-depth business plan. Jason Fried and David Heinemeier Hansson, on the other hand, suggest that all of these activities are simply a waste of time.

Indeed, in his attempt to ‘rework’ the tried-and-trusted, Fried and Heinemeier Hansson instead argue that it’s more productive to ‘stop talking and start working’, advocating positive actionable steps during the early stages. The bulk of Rework is aimed at showing budding entrepreneurs how to do just that. It’s endorsed by all the right people, too, from Seth Godin to Mark Cuban. If you’re the type to scorn tradition for an alternative way of doing things, then this could be the book for you.

7. Tools of Titans (Tim Ferriss)

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Following on from the success of The 4-Hour Workweek, Ferriss has carved himself a highly profitable niche as a blogger, author and podcaster. Tools of Titans is largely a product of the latter, with the former Princeton alumnus drawing on hundreds of interviews with celebrities, entrepreneurs and business magnates to discover what makes them tick.

The result is a series of common themes that seem to interweave between his subjects, suggesting that while people may find success in different fields and in different ways, their qualities, routines and characteristics are essentially the same. Tools of Titans won’t teach you how to start or run a business, but it will show you what it requires to be successful.

8. Like a Virgin (Richard Branson)

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It can be easy to forget just what Richard Branson and Virgin have achieved in business; no other company has been so successful in such a wide range of industries, after all.

Therefore, there is a lot of wisdom on offer in Like a Virgin, especially when you consider that this collection of entrepreneurial advice, business lessons and leadership tips come from a man who eschewed business school in favour of doing things his own way. With an estimated personal fortune of over $5 billion (£3.7 billion), he might just be worth listening to, as well.

9. The Discoverers (Daniel J Boorstin)

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Written all the way back in 1985, The Discoverers – a near 800-page musing on man’s historical interpretation of the world – may seem like a strange selection, but according to Thomas Hellmann of Oxford Saïd Business School, it’s essential reading for any aspiring entrepreneur.

Highlighting the section on Christopher Columbus’s discovery of the Americas (an event he describes as a ‘beautiful analogy’ of the entrepreneurial process), Hellman argues that the real value in The Discoverers is in dissecting our relationship with innovation and our uncertainty over the directions that we choose to take. These are issues that every business owner – small or large – will encounter at some point; and while it might be heavy going at times, there are few works out there that tackle such insightful questions with such depth.

Ultimately, there is no defined path or curriculum to starting your own business, so books like these are a hugely valuable means of understanding what it takes to be a successful and committed entrepreneur. If you pay close enough attention, it could even be you writing the next top best-seller.

What life-changing entrepreneur books do you recommend? Let us know in the comments below!