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Advice / Career Paths / Training & Development

5 Books Every Aspiring Entrepreneur Should Read

I'm working on launching a small business, and I’m learning quickly that a business education circa 2012 doesn’t always start in the classroom nor end with an MBA. These days, more and more of us with the entrepreneurial itch are turning to a more grassroots approach, gleaning wisdom from the words of those who have been down the path before.

These five books are the entrepreneurial know-how that's really spoken to me. Best of all, they're not stand-alone entities—they're the launching pad for (or result of) online communities built around successful business owners sharing insights on what's worked for them.

1. The 4-Hour Workweek by Timothy Ferriss

I dare you to read this and not get a little fired up and action-ready. The latest edition of this groundbreaker has even more tools and up-to-date content to help you create and automate an income-generator (a.k.a. your “muse”), leaving you free to pursue your passions: other business plans, travel, whatever. Ferriss blows old assumptions about business wide open, from the basic (the “bank hours” we all tend to keep are not the most productive) to the more intricate (he presents a plan to make an Aston Martin DB9 affordable with his Dreamline tool).

Favorite Takeaway: Ferriss argues, “…you are the average of the five people you associate with most, so do not underestimate the effects of your pessimistic, unambitious, or disorganized friends. If someone isn’t making you stronger, they’re making you weaker.” Tough to hear? Yes, but consider the truth to this. If you want to become a better runner, you run with a group that pushes you to go further faster, right? If you want to become the most buoyant, determined, and ordered version of yourself, surround yourself with great examples.

2. The Fire Starter Sessions by Danielle LaPorte

If you’ve been waiting for the go-ahead to pursue your next project, your red-hot permission slip just got delivered. LaPorte doles out 16 beautifully designed sessions chock-full of motivated goodness. Nothing preachy or perfectionist about it, but don’t be fooled: Her passion will grab you by the shoulders and shake action out of you. Personal tales give the sessions texture and make LaPorte seem so relatable you’ll forget you’re not actually friends. Self-help meets marketing ninja, this is definitely one to read and re-read.

Favorite Takeaway: Okay, it was hard to pick a favorite—the whole book is a takeaway. But, generosity is where it’s at: “Make generosity part of your growth strategy. Don’t wait. Don’t wait until your stuff is selling or you’ve got enough of a cushion in your bank account. Don’t wait until you’ve got more time. Give now.”

3. The $100 Startup by Chris Guillebeau

As it turns out, you don’t have to be a trust-fund baby, on the hook for a business loan, or just plain old lucky to start your very own enterprise (there goes that excuse). Guillebeau gives rousing examples of somewhat-accidental entrepreneurs making success out of strife, opportunity, and circumstances—mostly by turning a passion or hobby into something that can be profitable, and always by starting for less than most of us invested in lattes in the past year. He doesn’t necessarily encourage every knitter to open a yarn store, but he does promote creative thinking about how you can leverage a natural talent or long-loved activity into a business model.

Favorite Takeaway: Old-fashioned demographics are dead. As Guillebeau says, “Who are your people? You don’t necessarily have to think of them in categories such as age, race, and gender. Instead, you can of them in terms of shared beliefs and values.” Think of the customers for an organic, vegan bakery that specializes in gluten-free products. Everyone who walks through the door may not be a single white female, but you can bet they will all be interested in health, wellness, and delicious breads and pastries.

4. Enchantment by Guy Kawasaki

What’s the difference between spending your money on something that immediately gives you buyer’s remorse and the angels-are-singing delight that comes with a real treasure? Enchantment. Guy Kawasaki unpacks this concept in a way that leaves you nodding along with his suggestions. As an entrepreneur, you’ll find more than a few gems in this to get you thinking about how to really take care of your customers. As a customer, you’ll be looking for businesses that employ this kind of caretaking so you can support them further.

Favorite Takeaway: Kawasaki redefined competition and market share for me. As he puts it, “There are two kinds of people and organizations in the world: eaters and bakers. Eaters want a bigger slice of an existing pie; bakers want to make a bigger pie.” In a world where entrepreneurs sometimes look around and think, “but it’s all been done before,” this statement makes you rethink the limits you’re setting on yourself and your business.

5. Finding Your Way in a Wild New World by Martha Beck

Now, bear with me: Although not directly business-related, Oprah’s life coach, Martha Beck, provides some crazy-challenging personal inquiry in her latest book that will speak directly to your inner entrepreneur. If you approach this with the idea of outing your real and passionate business self, you’re going to get rather serious rather quickly about what you’d actually like to do to make money. If you’re a somewhat New-Agey-hippie masquerading as a yuppie, so much the better: The spiritual and self-help aspects of this book will speak directly to your soul. If you’re not, give it a try anyway—you may be surprised how pragmatic these tools are.

Favorite Takeaway: Beck continuously revisits the questions, “How the hell did I get here? What the hell should I do now?” throughout this book. If you’ve ever asked yourself some variation of these questions, you’ll get to dig deeper by trekking with her through Londolozi (the African game reserve where Nelson Mandela stayed upon his release from jail over 20 years ago) on a miraculous quest for inspiration and change.