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Top 5 Underrated Books Every Entrepreneur Should Check Out?

Over my many years in business, I’ve read A LOT of books.

Personal growth books, productivity books, business strategy books, historical books, innovative marketing books, books about finance, books from the biggest titans in our industry…

I’ve learned A LOT about starting, building and scaling a business from books! 

And 99% of the books I’ve read have NOT had the impact that these 5 underrated books have.

For each book I share, I’ll give you actionable takeaways you can use to grow your business…

So, let’s get to it!

The E-Myth Revisited

First, we have The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It by Michael E. Gerber. 

This one’s a classic.

It had a major resurgence during the Pandemic when many people chose to leave their 9-to-5 life to strike out on their own.

The journey into entrepreneurship often starts with what Gerber calls an “entrepreneurial seizure.” It’s that moment when a Technician — someone skilled in a particular craft — decides they no longer want to work for someone else. 

But here’s the twist: 

This desire to ditch the 9-to-5, while powerful, often overlooks the complexities of running a business. 

It’s not just about being great at your craft — it’s about understanding and managing the entire business system.

This leads to what Gerber terms the “fatal assumption” — the belief that if you know how to do the technical work of your business, you’ll understand a business that does that technical work. 

In other words, because you’ve mastered your craft, you’ll naturally succeed in business…

When real business success comes down to a mindset shift — from a Technician to an Entrepreneur.

Because business success requires a different set of skills — like leadership, marketing, sales and finance… and the fatal assumption that once you’ve mastered the technical side of your business — you’ll automatically succeed — is why many businesses struggle or fail, especially in the first five years.

You need to build systems and processes that reflect your values and standards and produce consistent results. 

As an entrepreneur, you work ON your business, not just in it. 

This shift allows you to focus on growth, strategy and innovation rather than getting bogged down in day-to-day tasks.

You see, going into business isn’t just about doing what you love… it’s about creating a structure that allows your business to grow and thrive — WITHOUT being solely dependent on you…

This is why The E-Myth Revisited is a book you NEED on your shelf.

Deep Work

Next up, we have this absolute game-changer, Deep Work by Cal Newport…

I first read this one in April 2022 at one of the lowest points in my business. 

My attention was being splintered in a thousand different directions — constant pings and dings from this guy — Slack, social media, email, you name it…

I wasn’t able to get in and stay in my zone of genius…  

And I had had enough!

I even considered an offer to buy my company, Live Your Message…

But then something amazing happened…

I picked up Deep Work.

And since reading it, I’ve reclaimed my ability to experience levels of concentration SO DEEP that I’m able to create the work I’m meant to share with the world — ON DEMAND…

And I want that for you too!

What I love about Newport is he doesn’t believe in a one-size-fits-all approach. 

In Deep Work, he outlines four strategies for diving deep:

The Monastic Approach: Think of monks in a monastery. It’s about isolating yourself completely to focus… 

    Imagine retreating to a cabin in the woods to write that novel without any distractions whatsoever.

    Now the next Deep Work Strategy is the Bimodal Approach: This is where you split your schedule according to the depth of work.

    This is where you plan large, uninterrupted blocks of deep work time — where you work in a monastic style. Then, when you’re done, you move on to more shallow work. 

    To make this approach work, you have to dedicate enough time to reach maximum cognitive intensity so you can really go deep. 

    Newport recommends allocating AT LEAST one full day each week for the Bimodal Approach to really work. 

    Now, the third Deep Work Strategy is the Rhythmic Approach. This is what I primarily practice and the easiest way to start dropping into deep work sessions. 

    Consistency is key here. 

    You want to schedule daily 3-4 hour deep work sessions and get them on the calendar. I don’t take meetings before 1pm so every morning is dedicated to deep work. 

    And, lastly, there’s the Journalistic Approach. This is perfect for those with busy schedules.

    It’s about seizing any unexpected free time and dedicating it to deep work. This strategy requires you to change from low-intensity tasks to Deep Work on a dime.

    Don’t be afraid to mix approaches! 

    The key is to be intentional and track your habits to find what works best FOR YOU.

    She Means Business

    Next up, we have a book for EVERY entrepreneur who’s let fears and doubt hold them back — which is all of us, to be honest!

    In She Means Business: Turn Your Ideas Into Reality and Become a Wildly Successful Entrepreneur, Carrie Green really pulls back the curtain to show just how much fear and vulnerability even the most successful small business owners carry.

    No matter where you are on your entrepreneurial journey, we all carry our inadequacies and worries with us…

    We’re afraid we’re not good enough or that we’ll disappoint people. 

    We’re terrified we’ll fail and waste the time and money we’ve poured into our business.

    One of the biggest takeaways from She Means Business is Green’s focus on overcoming this fear and self-doubt. She shares her own struggles and how she pushed past them. 

    The key? 

    Embrace your fears, acknowledge them, and then take action DESPITE THEM. 

    Courage ISN’T the absence of fear but the decision to move forward even when you’re scared…

    Because that great idea living in your head… is meaningless if you don’t take action on it!

    So, break your goals into small, manageable steps and start tackling them — one by one — it’s these consistent actions that build momentum and lead to success.

    The Lean Startup

    Knowing you want to grow your business is one thing, but knowing HOW to keep it manageable is another… which leads me to my 4th book… and this one’s a classic!

    The Lean Startup is the ultimate rule book on HOW to grow your business steadily and manageably.

    This book has stood the test of time as one of THE definitive pieces on trimming the excess weight off a business.

    At its core, the Lean Startup methodology advocates for a systematic, scientific approach to creating and managing successful startups. Ries’s perspective is that startups should focus on learning WHAT their customers really want and then iterate their product quickly based on feedback… rather than spending years perfecting a product without understanding market needs.

    The Lean Startup approach has been a game-changer for us at Live Your Message!

    The Psychology of Money

    Quick riddle for you:

    This is something EVERY business needs to survive and thrive, but for many entrepreneurs, even the mere mention of it causes anxiety…

    Or simply ISN’T motivating. 

    If you said: MONEY… you’re spot on…

    Here’s the thing…

    According to Noam Wasserman, there are 13 specific motivations that drive us in our businesses… Altruism, Autonomy, Financial Gain, Lifestyle, Managing People, Positioning, Prestige, Recognition, Security, Variety, Power & Influence, Intellectual Challenge and Affiliation…

    And understanding your hidden motivations or WHY you do what you do makes growing your business SO much easier…

    Now, financial gain ISN’T one of the top motivations for many entrepreneurs — I know it’s not for me — but money IS vital to growing your business. 


    But so many entrepreneurs are completely turned off OR overwhelmed when the topic of money comes up.

    It doesn’t help that financial advice is often very technical. So it seems like money is ALL about spreadsheets and numbers…

    We know we should be saving in case an emergency comes up…

    We know we should have a retirement fund… 

    And yadda yadda yadda…

    So, what IF there were a BETTER way to look at money and finances? 

    There is!

    In The Psychology of Money, Morgan Housel points out that financial decisions can’t always be made with calculators, spreadsheets, and graphs…

    We make decisions with our heads.

    But you could know ALL the tips and tricks to become financially successful… but if your behavior doesn’t gel with what you know, you’ll NEVER succeed.

    This isn’t just true when it comes to your finances… it’s true in EVERY aspect of your business.

    As our income increases, we have this amazing ability to allow our expenses to increase — right along with them… am I right?

    And I’m not just talking about business expenses here… 

    As we start making money… we’re tempted to try to “keep up with the Joneses” — meaning bigger houses, better cars and “first-class” vacations…

    And, before you realize it, you’re on this hamster wheel of more money and more stuff…

    But, somewhere along the way, most entrepreneurs realize that their happiness is NOT tied to the accumulation of MORE…

    It’s tied to making a real impact on this world! 

    So, if you want money to fuel the impact you want to make, you can’t miss The Psychology of Money.

    There you have it — the 5 underrated books that’ll make a REAL, LEGIT impact on your business…

    Go ahead and drop me a comment with 2 things — which of these 5 books you’re reading FIRST AND an underrated read you recommend…

    Now, if you’re keen to grow and scale a business that allows you to make a potentially unlimited amount of money and impact…

    Check out my yearlong business accelerator — Momentum!

    Here’s the thing: usually, when it comes to the support you need to take your business to the next level, you’re forced to choose between: 

    • Private Coaching…
    • A Small Group Mastermind… 
    • Or Live Events & Workshops…

    And — while each one of these things is awesome… they’re NOT enough to guarantee the business results you’re after…


    With Private Coaching… you’re missing the perspective that comes from community…

    With Small Group Masterminds… you’re lacking the depth and accountability of having that private coach…

    And with Live Events & Workshops, you get pumped, but then the excitement fades and you fall back into procrastination and overwhelm…

    That’s why I’ve created ONE cohesive program that gives you ALL 3. I like to call it a best of ALL worlds program!

    You get Private Concierge Coaching, Small Group Masterminds and Live Trainings and Quarterly Events. 

    Yes, ALL 3 in one value-packed program! 

    So, if you’re excited to learn more about how me and my team can support you in realizing your biggest business goals this year… schedule a no-pressure Call with a Program Specialist

    So, schedule that call and I hope to see you inside Momentum!

    Now, go out there and Live Your Message! 

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