The Best Entrepreneurship Books To Grow Your Business

I’ve read a lot - I mean a lot - of business books. From classics like Think and Grow Rich, to all the Gary Vee books. From methodical and straightforward to thought-provoking and woo-woo.

There are books I love so much I’ve re-read them multiple times, and ones that I never finish because they just don’t speak to me. Confession: I used to finish books based on the mere principle of checking it off as complete - mama doesn’t have time for that anymore.

I know there’s a big market out there specifically for the “girlboss” or “boss babe” type. These books are usually marketed with shades of pink and gold foil. That’s cool, but it’s not a determining factor in if I choose to read a book or not.

Inevitably, the typical “girlboss” books end up falling flat with me. Unpopular opinion alert: I couldn’t finish Girl Wash Your Face. I like Rachel Hollis but the book landed for me as repetitive and the lessons were ones I’d learned long ago.

I find the books that spark my interest, motivate me, and make me think in new ways are usually more about practical advice and implementation, with a dose of mindset awareness.

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The following books have been the most influential business books for me over the course of my entrepreneurship journey.

They are the top of the list for those that have helped me grow the most - personally and professionally - in the most profound ways.

You can click the red hyperlinked booked titles to shop directly on Amazon, or click on the gallery images at the end of this post.*

The Big Leap

The Big Leap sparked the biggest, most pivotal moment in my business. It made me realize that my zone of genius is TEACHING.

Yes, I love my clients and I find so much satisfaction in helping their businesses grow, but what really - really - lights me up is when I get to teach other entrepreneurs how amazing using Pinterest for their business marketing can be. Those lightbulb moments are why I do what I do.

Vulnerable confession moment: My sister and I do not get along. We’ve never gotten along and our relationship has always been a struggle. When I was little, I remember thinking I wanted to be a teacher. Then she became an elementary school teacher (she’s older and went to college first), and I felt like that wasn’t an option for me anymore - like that role had been filled. My biggest pet peeve was ever, ever being compared to her and so that door was closed.

It was the same situation with thinking I was “uncreative”. She is a naturally-talented artist, and I was not. I remember clearly trying to draw an elephant at some zoo summer art camp when we were kids and she told me it was terrible. In that singular moment I labeled myself and “uncreative” and not an artist.

It took me 30 years to allow myself to step into the fact that I am not only a gifted and talented teacher, but I’m incredibly creative as well. The Big Leap played a major role in that realization.

If you are struggling to break through to the next level of your business, or need some clarification on what it is that really lights you up, read this book!


Surge is the first of 3 books by Mike Michalowicz on this list. It is a unique take on spotting trends before they’re over-saturated. Mike uses a metaphor to illustrate the concept - in this case, it’s riding a wave and using Ugg (the company) as a case-study.

This book planted the seed for creating Pinterest PowerUp as a membership community. I knew that the online entrepreneur space was over-saturated with Pinterest courses. I had heard so much feedback about courses that were crappy and didn’t teach beyond top-level concepts, and ones that were ok, but already outdated.

I knew 2 things:

  1. My zone of genius is teaching, and

  2. There had to be a way to really dig into teaching people the whole picture of using Pinterest for their digital marketing strategy, while staying up-to-date with the constant changes.

Pinterest PowerUp is the first Pinterest marketing membership designed for online entrepreneurs. We not only teach the foundational best practices of Pinterest for business, but we deep dive into collateral subjects like analytics, graphic design, and email marketing.

Because getting traffic from Pinterest is great...but what do you DO with that traffic to make a difference in your business and income?

We launched in December 2018 and have been building raving fans and a community of support ever since. I’m sure it won’t be long before other Pinterest marketers spot the wave of how much a membership community makes sense to teach Pinterest and will copy my model. That’s business right?

Surge is a great read if you’re ready to think about your industry and your business differently to stand out from the pack.

The Pumpkin Plan

The Pumpkin Plan was the first of several Mike Michalowicz books I’ve read that has made me a better small business owner. Mike writes with an incredible, sarcastic sense of humor that actually makes me laugh out loud. A business book that makes me laugh and teaches at the same time? Yes please!

The Pumpkin Plan is all about choosing how to niche your business. It teaches how to think, analyze, and tweak your business services and products to be more profitable.

Mike compares how to grow prize-winning pumpkins to how to grow a more profitable business - and it’s a kind of silly metaphor that totally works.

This is the book I was reading when I went on our first family vacation ever and decided to completely change the direction of my business.

Read: Why Choosing To Niche My Services Was The Best Decision Ever

If you’re struggling with what to offer your clients or customers, and you feel like a “jack-of-all-trades”, this book will help.

The Mindful Entrepreneur

The Mindful Entrepreneur was a random book that I read for free as part of my Kindle Unlimited subscription, and turned out to be one of the best books I’ve read for understanding how to structure my business and set myself up to build a team.

As a previous solopreneur, I know it’s easy to ignore the essential roles and responsibilities in your business when you’re “wearing all the hats”. You’re so busy in the day-to-day grind of pumping out the work, that you can’t see your business as a CEO.

In other words, you’re so busy working IN your business, that you’re not working ON your business.

Joel overlays a story onto a business owner’s journey from being at the breaking point with his business to growing and expanding.

In particular, I found “Chapter 9: Going Into Training” to be super practical and valuable to lay out the structure of the different roles in my business. I re-created the example organizational chart for my own business, and it’s now one of the first things in the Chace Digital Handbook.

If you need to break out of the daily grind of working IN your business, this is the book to read.

Profit First

Profit First is another of Mike’s books and maybe his most well-known (I swear I’m not the President of the Mike fan club). The principle of this book is teaching entrepreneurs how to pay themselves first. This is the basis of his whole mission - to teach entrepreneurs and small business owners how to stop being broke.

While I don’t follow his exact profit and account methods, it established the foundation of my own system and yes, I do pay myself first.

I do believe there tends to be a societal conversation about women “not being good” with money. There is a shocking lack of financial education in our public school system, but that is a whole other conversation.

If you’re feeling like you don’t quite have your head wrapped around how to handle your business finances - this is the book to start with.

You Are A Badass At Making Money

You Are A Badass At Making Money is the follow up book to Jen Sincero’s “You Are A Badass” - which I also loved. This book makes the list, however, because it truly knocked my socks off in the most uncomfortable gut-wrenching way.

There are very few books, let alone business books, that have made me angry and cry.

I was so angry I put it down for weeks.

Looking back, I don’t think there was a particular moment or point in the book that made me angry, it was more when you have that awful inkling that maybe the filter with which you see yourself for your own protection is no longer serving you.

Yeah, that kind of uncomfortable, hand-wringing, I don’t know whether to nap or go for a walk, kind of feeling.

After considering throwing it in the trash or burning it for a few weeks, I made myself pick it back up and finish it. This was not the situation where I finished it to check a box. I finished it because it made me so uncomfortable with my own money mindset that I knew I had to break through to fix it and grow.

I finished it, then I promptly read it again while taking action and notes. I rarely read a book again twice (first for overview, then again for action) - but this was one.

If you have some old story bullshit to work through around money - read this book. Twice.

Pro Tip

I find personal development and business books that are practical and thought-provoking to be mentally exhausting if read them back-to-back. It’s still work - even if you’re reading in bed and you feel like you’re taking a break.

I like to switch up my business books with fiction that I can lose myself in (my favorite genre is historical fiction). Fiction truly gives my brain a break and I can go back to a business book feeling like I can take it all in and absorb the concepts.

Got any must-read business books on your list that have helped you grow?

Join Pinterest Rockstars and let us know!

Why Join A Pinterest Marketing Membership?

Why join a membership specifically focused on Pinterest marketing, instead of a broad-based social media marketing program?

The reason I decided to niche from Social Media marketing into Pinterest marketing was I was a “Jack of all trades, and master of none”. Once I realized what Pinterest was doing to drive my sales and leads funnel - it was a no-brainer.

Instead of barely maintaining your workflow and knowledge about a handful of platforms, you’ll get in-depth training, community, and support for the platform that gives your business the best return on investment.

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Hey hey, I'm Cara - the CEO of Chace Digital, a Pinterest marketing agency, and the Founder of Pinterest PowerUp, the first Pinterest marketing membership community designed for entrepreneurs. I love nothing more than seeing those light bulb moments with clients and members when they see how Pinterest builds their businesses... except for maybe a good book and another cup of coffee.

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