8 Books That Helped Me Become an Entrepreneur

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Before I took the leap from full-time employee to an entrepreneur, as a founder and CEO of my own company, I read a lot of books. Mostly because I LOVE to read, but also because books provide invaluable glimpses into the minds of the wise who are willing to share their experiences and lessons.

While I’ve read many great books, I’ve also read many mediocre books. Here are my recommendations for my favorite or most influential books that helped to shape who I am as a professional, and who I want to aspire to be.

I have both the business-type books AND personal development, because the way I perceive the world, my time left, the way I want to live my life, and the impact I want to have on the world requires me to grow both as a human being and as a business woman. To me, I wouldn’t be where I am, doing what I love, living out my dreams if both parts were not inspired.

So if you are looking to freelance, start a side hustle, or perhaps even quit your job and become self-employed, check out some of my recommendations!

Marketing/Entrepreneurship/Management

Side Hustle: From Idea to Income in 27 Days

Side Hustle (Chris Guillebeau) provides a step-by-step guide for anyone to start and grow their own profitable side project in just a month. He helps you create a side hustle, which brings you money without the risk to your stability that head-long entrepreneurship has, which will help you evaluate whether your idea really is viable and worth quitting your full-time job for.

I love Chris’ books, and have read all of them. He writes for readers who don’t have full-blown technical skills that could help expedite their profitable businesses, like a coding or marketing or business degree. He explains how to build a business without any technical expertise, with hundreds of sometimes extremely strange examples of how people make $500/mo or more while keeping their full-time job.

The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future

The $100 Startup is another one of Chris’ books, and in this book, he’s identified 50 case studies of interesting side hustling stories to feature. These side hustlers have no special skills, but found very interesting and original aspects of their passions that could be monetized, and have found fulfillment and freedom.

When someone is looking to start a side hustle, or wondering how they could earn some extra cash, I always refer them to Chris’ podcast, called Side Hustle School. They’re super short (10 minutes?) daily episodes that highlight one side hustler and their business that makes them at least $500/month, which they do on the side of their full-time job. He goes into detail on what resources they used, how much the start up costs were, and how they managed to scale.

Cashvertising: How to Use Secrets of Ad-Agency Psychology to Sell Anything to Anyone

Ca$hvertising (Drew Eric Whitman) is a classic book for beginner and advanced marketers. If you are going to sell anything, whether it be your services or products, you should check out this quick read.

He gives real-life examples with every point he gives, and as the cover suggests, he gives out “over 100 secrets” on how to grab the prospect’s heart… And wallets.

While some of the points are a little over the top, there are A LOT of very important nuggets of information in this book, so I recommend getting a paper copy to highlight and take notes on! You’re bound to learn at least ONE new thing a chapter that will help you more effectively pitch and sell.

Start with Why: How Great Leaders Inspire Everyone to Take Action

Start with Why (Simon Sinek) talks about why some managers are effective, while others aren’t. Why some organizations thrive while others harbor toxic cultures. We all know the manager we dislike, and most of us quit our jobs over managers, rather than the job itself.

The difference between effective and innovative organization and people is starting with the WHY, according to Simon. Powerful leaders all think, act, and communicate in the exact same way, which he says is complete opposite of what everyone else does. He calls this The Golden Circle.

This book is a great resource both as an entrepreneur and as someone who might some day become a manager. And to be quite honest, just being an effective member of society. Why people follow certain leaders, but not others. Because they start with the WHY.

Personal Development

Give and Take: Why Helping Others Drives Our Success

Give and Take: Why Helping Others Drives Our Success (Adam Grant) talks about 3 types of people: Givers, Takers, and Matchers. They can be perceived as types of people, or “life philosophies.” Givers help whenever they can to benefit others, regardless of their own personal cost. Matchers aim to find an equal balance of giving and receiving, always keeping track of the “score.” Takers help only when the benefits exceed their personal costs, and will only engage in giving when it benefits them in the transaction.

As a natural Giver, who have too often been taken advantage of, this book helped me realize that it’s not a “bad thing” to be a Giver, even as an entrepreneur who wants to grow her business, and that there are effective and ineffective ways to share my resources in time so that I can net positive in the long run.

How to Be Everything: A Guide for Those Who (Still) Don’t Know What They Want to Be When They Grow Up

I learned what the word “Multipotentialite” means from How to Be Everything (Emilie Wapnick). Well, that makes sense, because she made that word up! You might know the concept as… a polymath, “renaissance man,” generalize, multipod… etc. Emilie defines Multipotentialite as someone with many interests and creative pursuits.

Finally, someone was telling me that it’s ok to have multiple passions and creative outlets. That it’s ok I’m flitting from obsession to obsession, creating massive amounts of resources in my wake everywhere I go. I don’t have to “pick one,” and “settle.” I can continue working the way I work best… Because I’m just me! And that’s quite alright!

You can check out her TED talk: Why Some of us Don’t have One True Calling:

I have a “Why” that all of my seemingly scattered projects and passions revolve around. As long as I have the core Why intact, I can stick my paw into many different fields, occupations, and interests, and still come out strong.

The Four Tendencies: The Indispensable Personality Profiles that Reveal how to Make Your Life Better

It’s not an overstatement to say The Four Tendencies (Gretchen Rubin) changed my life. It’s a book, but it’s also a sociological concept that Gretchen came up with, where she breaks down “tendencies” of all people into four groups: Upholder, Questioner, Obliger, and Rebel.

I know, I know. You’re probably thinking, “Hiro! I took you to be a logical, science-based lady!” I am! But hear me out. The best part about this theory is that you are one (or multiple) of these tendencies, and knowing which tendency you have allows you to “hack” your personality and your natural responses to situations to be more productive, develop habits, and generally improve your life.

Better than Before: What I learned about Making and Breaking Habits

From reading this book, and especially Better than Before (same author, and also highly recommend!), I learned that it’s ok to need external accountability to get things done. That I might need “help” from having someone check in on me to see if I’ve finished my project quota in order to get it done. Or to schedule my meetings at 11am on Mondays so I would be forced to be up and ready for a video call at least by that time, because otherwise I might stay in bed until 3pm. Regardless of the WAY it got done, if it got done, then I win!

This was a huge relief and revelation to me, because I’ve always been someone who needs external motivation. I am the one that announces she’s going to do something, because just deciding for myself won’t help me accomplish anything, but telling the world makes me feel obligated to do it, and I do it. I can’t get myself to go to the gym even once every 3 months, but I can lose 20 lbs and run 4 times a week when I have a running buddy. I can stay away from bad food if I’m doing a “challenge” with someone else, who will judge me (rightly) for breaking my diet.

But as an Obliger, I am much more bound to my words when I think I’m letting someone else down than myself, so I need external accountability to get things done. And, as these books told me, that’s 100% ok! Use whatever I need to get things done!

Curious? You can take a quick The Four Tendencies Quiz to get a pretty good grasp on which of the four you are!

Books Help Me Grow

People always asked me, especially when I was working a full-time job and juggling multiple side hustles, how I did it all. These books helped open my eyes to different ways of using time, resources, and my energy to be more productive and focus on things that are really important.

And I have to say, I’m pretty pleased with the results!

Let me know if you’ve read any of the recommendations, or if you have any books of your own to recommend! I’m always on a hunt for a good book to help me in my business or personal growth journey!

This post may contain affiliate links and I may be compensated if you make a purchase after clicking through my links. I only recommend products or services that I 100% believe in, or created myself!

Hiro is CEO of 24 Villages, and Technical Instructor LinkedIn Learning. She writes to introduce Cloud Computing and AWS to beginners at Intro to AWS and various client blogs.

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