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The 5 books every business owner needs to read

Reading. That either sounds like fun to you or homework.

I get it. You only have so many hours in the day. Why spend them NOT working on your business?

Well, here’s my answer: The right kind of reading is the ultimate form of working on your business.

Like many business owners, I’ve felt overwhelmed and unsure about what direction to take. I read about a book a week. I’ve read through a mountain of shitty books to get to a handful of exception ones that changed my entire perspective and helped me change everything in my life and business.

Here are those books:

1) Pitch Anything by Oren Klaff

Oren Klaff is an investment banker. He pitches deals all the time, and in the financial world, it can sometimes be tough to differentiate your deal and make it riveting.

That’s why Oren is a beast at pitching. His book walks you through a way to tell a story when you pitch, how to really connect with someone emotionally so they are actually engaged.

He also devotes a ton of time to managing the power dynamics of pitching. We’ve all been there before – with our hat in our hands, acting like we’re pleading with someone to buy from us. Have you noticed how those pitches usually bomb? Oren goes over why that happens and breaks down how to manage those power dynamics so you’re on equal footing.

When you’re selling, it’s important to remember that you’re there because you have some valuable, too.

2) Start With Why by Simon Sinek

OK, so for this one, you could probably just get by watching Simon’s TED Talk, which he absolutely crushed:

But, if you got through that and are wanting more, check out his book.

He breaks down how leaders of causes and leaders of industry talk one way – and the rest of the world talks exactly the opposite way. One group stands out and connects. One blends in and does not.

It starts with thinking about “why” you exist. It starts with talking about your values, your dreams, your beliefs. Everyone else leads with “what” they’re selling, and it often doesn’t land because we’ve heard it all before.

Rarely do organizations, politicians, and leaders truly speak from their heart. This book is key to understanding branding, leadership, and speaking.

3) 4-Hour Work Week by Tim Ferriss

Super popular for a reason. Tim Ferriss is definitely a cocky dude, and I’m not so sure I’d be his friend if I met him, but God damn it, the guy has some amazing ideas.

As you may guess, he shows you how you can work a tenth of what you normally work and produce the same results. He focuses on the concept of “lifestyle design,” in which your work fits into the lifestyle of your choice.

Maybe you want to travel. Maybe you want to spend more time with your family. Maybe you just want to watch the New York Mets get crushed everyday. Fitting in those wants starts with intentionally designing your work life so your work doesn’t design your life for you. There’s a lot of hands-on, practical advice in here that you can apply immediately, which I especially like.

While I work a hell of a lot more than four hours in a week, this book really helped me achieve a little more work-life balance so that I was living a complete life.

4) The E-Myth Revisited By Michael E. Gerber

When you roll up with a headline of “Why most small businesses don’t work and what you can do about it,” you know this guy is going hard in the paint.

And he does. The first chapter, I was legit offended. The guy is telling you why your business doesn’t run right. I spent most of the time thinking, “Nah, this guy is way off,” but eventually, I got over myself and realized that he was 100% right.

The concept is this:

  • When you start a small business, it’s usually because you’re competent in some technical skill, not because you’re some swashbuckling Richard Branson who sets up a team.

  • You usually don’t have a ton of experience managing or delegating, so you wind up doing a ton of work yourself – and the work you do delegate, you either micromanage or completely ignore.

  • There is no set process for how to do many things, which leads to inconsistent results that people struggle with.

I’m very lucky I read this book early on, when I was just starting to hire folks, because this saved me big time. I came up with rigorous systems and training videos for just about every process in the business – and I IMMEDIATELY saw the changes. More consistency, less confusion, less stress.

Too often, it’s easy to assume that people understand you or your ideas. Usually not the case. In fact, usually you did a poor job communicating your idea and made many assumptions. By really systematizing everything you do, you’ll better communicate with people, and you’ll discover better ways to do everything.

5) Growth Hacker Marketing by Ryan Holiday

This is one of those books where it puts words to something I’ve long believed and preached myself.

Sorry, Don Draper, but advertising your way is dead.

It’s true, though. In my opinion, and as Growth Hacker Marketing asserts, the key to marketing these days is in finding efficient ways to acquire users/customers/leads. It isn’t coming up with a slick ad in a smoky boardroom and pumping it out across the airwaves.

Having something like “Sent from my iPhone” on all your mobile emails – that’s a better piece of marketing than any TV commercial. Stories still work. Flashy creative still works. But, there’s a lot more to it. With all the data we now have, we can do a lot better than we could before.

This book is all about helping you understand the power of digital, the power thinking small to get big results, and how we’ve gotten so good at measuring results that we need to be equal parts scientist and artist when it comes to marketing and advertising.

BONUS: Get Overdrive

How do you read books? I read them the old-fashioned way sometimes, but I’m a huge fan of audiobooks. You can read while you’re driving or working out, so you can get the most of out your time.

I used to rack up some serious charges on Audible, which is great, until I found out about Overdrive. With Overdrive, you use your library card to get access to tons and tons of audiobooks for free from your local library.

Just a heads up on that because it really changed my monthly book budget.

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