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Insights for Entrepreneurs

7 Unconventional Books for Entrepreneurs


A startup is a special kind of business. It’s chaotic, energy-charged, and moving at a million miles an hour. That’s why creating and managing a startup can be an incredible (and exhausting) experience.

The old fashioned and standard business books aren’t going to cut it. Sure, The Lean Startup is a must, but the following books can give you unique insights that go beyond the average book for entrepreneurs.

Unconventional startup books can teach, inspire, and get you going. Here are seven awesome reads:

1. The Tipping Point – Malcolm Gladwell

Any Gladwell book could make this list– you’d get something out of all of them– but The Tipping Point feels like it was written for entrepreneurs.

The Tipping Point by Malcolm GladwellIn it, Gladwell explores that unique moment when an idea becomes a movement, when potential becomes reality. It applies to everything – from changes in crimes rates to booms in fashion trends – but it has particularly valuable insights into why people buy what they buy, and how small, almost imperceptible actions can create the tipping point a startup needs to succeed.

You’ll learn about:

2. The 4 Hour Work Week – Tim Ferriss

Ferriss has an extreme personality and it shows in all of his books. There are some real gems in here that apply directly to how a successful business can operate with fewer people.

The 4 Hour Work Week by Tim FerrissStartups are small and grow quickly, so they need to be lean and mean. Using the same strategies Ferriss uses to work only 4 hours a week, you can run your startup on a skeleton crew until it’s ready to scale.

You’ll learn about:

3. To Sell is Human – Daniel Pink

All the flashy widgets and features in the world don’t mean a thing if you can’t sell them. Pink’s book isn’t so much about how to sell as the phenomenon of selling in general.

To Sell is Human by Daniel PinkTo Sell is Human: The Surprising Truth About Moving Others is a fascinating look at the human urge to share, the most effective selling strategies we use on a daily basis already, and how things like social proof and word of mouth can amplify your efforts in ways that advertising can’t.

You’ll learn about:

4. The Power of Habit – Charles Duhigg

This book should be required reading on the first day of college – it is that important. While Duhigg doesn’t uncover anything that’s new to science, he presents the nature of habit in such a simple, easy-to-follow way that you can’t help but see exactly how it can affect your business.

The Power of Habit by Charles Duhigg Creating the right habits, removing the bad ones, and building keystone initiatives that enable a successful organization – this is just some of the stuff Duhigg talks about.

You’ll learn about:

5. The Autobiography of Benjamin Franklin – Benjamin Franklin

Inventor, business owner, diplomat, writer, and revolutionary – Benjamin Franklin did it all, and then he wrote about it. In his autobiography he shares amazing ideas about organization, talking to people, generating trust, and building an audience.

The Autobiography of Benjamin Franklin - Benjamin FranklinWho else to learn about organization and adoption techniques from than a man who helped America organize before and during the Revolutionary War, founded the Post Office, and invented dozens of gadgets we still use today?

You’ll learn about

6. The Art of War – Sun Tzu

The Art of War is something of a business cliche. Business schools assign it, entrepreneurs carry it around, and CEOs have annotated copies on their shelves.

The Art of War by Sun Tzu Yes, it’s about war, but it’s also about managing people, understanding the opposition, and organizing a diverse set of systems to move toward a singular goal. All vital tasks for a startup entrepreneur.

You’ll learn about:

7. The Wisdom of Crowds – James Surowiecki

The Wisdom of Crowds by James SurowieckiIn the eight years since Surowiecki wrote his ode to group-think, the world has changed. Startups flourish on sites like Kickstarter and Indiegogo. Businesses manage staff through Elance and Amazon Mechanical Turk. Products are developed in the wild, almost constantly in beta instead of closed door labs.

Did Surowieki have prescience or a keen sense of observation? Either way, he saw the writing on the wall when he declared that crowds are better than individuals at solving problems, predicting actions, and innovating. As a startup, this should speak directly to the development of your product.

You’ll learn about:

If you’ve read any of the books above, please share what you gained. If you haven’t but recently read a book that you think should be on this list, please share in the comments below!

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  • Jeremy Kersten

    Sounds like a wonderful list. I will definately be checking those out.

    • Emma Siemasko

      Awesome, Jeremy. I’m a huge fan of Ben Franklin’s Autobiography and all of his other writings- he’s so industrious. Let us know if you read a book you like!


  • Darren Scott Monroe

    YO!! you guys didn’t mention Seth Godin

    He wrote not THE book but several books on “unconventional” Did one of the largest crowdfunded books to date

    Plus my favorite is We Are All Weird!
    (non affiliate link below)

    • Emma Siemasko

      Hi Darren,

      Thanks so much for pointing out these awesome books by Seth Godin. Hopefully some of our readers can pick them up. There’s a few other unconventional books that could’ve made this list. I’m reading “Rework” by Jason Fried of 37Signals right now. I think it’s excellent.


  • Allison Graham

    Hey – these are great – but think it’s a stretch to call them “unconventional” books – these are the same books everyone recommends!! Yes they are excellent, but they are recycled. Makes it hard for the little guys – with great material to get noticed. Why not suggest some that aren’t on everyone’s automatic most recommended list? When I read your title, I clicked over excited to read something “new and unconventional” I’ve got about 300 biz books on my shelf – none of which will ever get the same exposure, but that have made significantly more valuable impact – or at least as much – than the standard fare! Just sayin’ Maybe I’m just sensitive to it as I’m an author (fortunately get recommended and have done quite well with my book) but hear from others who have amazing content and just don’t break through cause the big guys dominate. :)

    • Emma Siemasko

      Hey Allison,

      Thanks for your insightful comment about truly unconventional books. You’re right- these aren’t out of the ball-park weird when it comes to business books, although I do think reading books like Ben Franklin’s Autobiography aren’t standard fare. I’m really curious about what little guys you’d recommend, as I think all our readers can benefit from getting more exposure to other books and new ideas. Personally, I want to know what’s awesome on your book shelf! Feel free to share in the comments, but you can also shoot me an email at esiemasko at to talk about these reads. Thanks again for your comment!


  • Allison Graham

    Hi Emma,
    Thanks for responding, I’ll definitely send you an email. It’s funny, cause when I look at my book shelf, it’s hard to narrow to the best. My view on books is you can never read enough! So you soak up all the info and then figure out which bits make the most sense for one’s own application. I haven’t read Ben Franklin’s bio – so will do that! I love reading Winston Churchill’s musings as well. Lots of great advice. Sometimes reading outside of the biz box can have the most impact on business success.

    • Emma Siemasko


      So glad you got back to me. It’s so hard to choose the best books off of my shelf, too. I’ve got a bunch of buzz marketing books on my desk right now.

      I’m a fiction reader myself and whenever I talk about a book I love, I end up saying, “well, I also love this book and this one and this one and this one!”

      Looking forward to connecting to talk about some truly unconventional business books. You think there are any poetry collections we can add in there? I’ll be waiting for your email.


  • Mark

    Allison, I’d also be interested in your list of recommended reading.

    • Emma Siemasko

      Hi Mark,

      Thanks for the comment. I’ll be sure to let you know if we stumble upon any other great books.

      Any unconventional books you’d add to the list? I’d love if you emailed me your list, too: esiemasko at


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