Karl Hughes

Karl Hughes

12 Entrepreneurship Books That Impacted Me the Most

12 Entrepreneurship Books That Impacted Me the Most

A lot of new entrepreneurs ask me what books they should read (or which ones I like), and I find this question surprisingly hard to answer.

The problem is that the impact of a book is dependent on your current situation and challenges. The books that impact me most now probably wouldn’t have been helpful earlier in my journey, and the ones I read when I was first starting out probably wouldn’t be as impactful to me personally anymore.

I also read a lot, and many of the books that have impacted my entrepreneurial journey the most aren’t typical business books.

Classics like Good to Great and Measure What Matters are great all-purpose business books and will help you be a better manager, but I find their application to entrepreneurship pretty weak.

With those caveats aside, I thought it would be interesting to share the 12 books that have had the biggest impact on my entrepreneurial journey. I’ve organized this list chronologically, so I’ll explain each book in the context of its impact on my life at the time.

Hopefully, some of these will hit you at just the right time in your entrepreneurial journey to make a big impact too.

1. The Four Hour Workweek by Timothy Ferriss

Unlimited Power book cover

After I graduated from college, I spent 6 months living in a tent and touring the Eastern half of the United States. During this period, I had a job with a small startup where - for the first time - my income was removed from my hours. I was paid for producing results, and I typically didn’t have to work many hours each day to hit my numbers.

Needless to say, The Four Hour Workweek appealed to me, but it also made me realize that reaching your goals as an entrepreneur doesn’t have to be tied to working more hours.

This was a pretty new concept to me because most small business owners I knew at the time worked much harder for much less money than I wanted. Reading The Four Hour Workweek gave me permission to work smarter, and helped me realize that by leveraging people and processes, I could maximize my impact while minimizing my time spent actually “working.” It also turned me onto the idea of tracking my time so I could understand what I was actually doing and critically evaluating whether I needed to be the one doing it.

I re-read this book in 2022, and while I still like it, I realize how outdated some of the tactical advice it offers is. That said, I’d still recommend the first half of the book. If you’re interested in how the book has held up, there’s a good episode of Tropical MBA that goes into more detail.

2. How to Win Friends and Influence People by Dale Carnegie

As I was traversing the country in my car, I happened to read another book that I continue to reference and reflect on today: How to Win Friends and Influence People.

While the title sounds cheesy (and honestly, the book is pretty cheesy), I took away more from this book than any other business advice book I had read before. Little things like, “a person’s name is to that person, the sweetest, most important sound in any language” and “the man you are talking to is a hundred times more interested in himself and his wants and his problems than he is in you and your problems” ring through my head every time I have a conversation with a new person.

The bigger my companies and my role has gotten, the more I come back to this book’s advice. So much of my day-to-day now is sales and subtle influence that it’s critical not to loose sight of this book’s basic wisdom.

If you can accept that this nearly 100-year old book uses outdated style and language, you’re in for some of the most important lessons anyone can learn.

3. The Mom Test by Rob Fitzpatrick

Unlimited Power book cover

After my 6-month stint living in campsites, I spent 10 years working as a software engineer at various early-stage startups. During that time, I read more about engineering and management, but in 2020, I started thinking about leaving my day job to start my own business.

I had seen many startups build products and services that nobody really needed, so as I began to evaluate business ideas, I knew I had to avoid the same mistake.

My good friend, Tony Chan was a few years ahead of me in running his own business and he recommended The Mom Test. This short, pithy book gave me one key takeaway that I continue to use whenever we launch new products and services:

Don’t ask customers what they would pay for. Ask them how much they currently pay to solve their problem and what’s wrong with the solution they’re using.

Getting someone to open up their wallet and spend money on something they haven’t spent it on before is incredibly difficult and it’s the reason most startups never get off the ground. Nobody really needs you to solve the problem, and if they did, they’d be spending money on solving it already.

Shut up and take my money

Instead, try to find a business model that solves an existing problem - with a dedicated budget - better, faster, smarter, etc. It sounds simple, but this advice is rarely followed.

4-5. The War of Art by Steven Pressfield and Big Magic by Elizabeth Gilbert

My first business was a technical writing company, and in the early days, I did just about everything myself; I was essentially a freelance writer.

This got me on track to read a bunch of books about freelancing, writing, and creative pursuits, including The War of Art and Big Magic. I grouped these books together because I took very similar messages from both:

Success is a function of doing work, overcoming fear, and persisting in the face of apparent failure.

Both Pressfield and Gilbert spent decades as struggling writers, churning out content that nobody would read or recognize. Both of them mention the fear they had and saw others succumb to along the way. Fear that they were wasting their lives; that they would never figure out how to create something people wanted.

As an entrepreneur, this message still resonates with me.

Most entrepreneurs I know aren’t any smarter than other ambitious people. They don’t necessarily work more hours or have special skills either. The constant thread I see in entrepreneurs is that they overcame fear and kept going despite apparent failure.

I reference Gilbert’s poem to fear all the time, so I’ll quote it here as well:

“Dearest Fear: Creativity and I are about to go on a road trip together. I understand you’ll be joining us, because you always do. I do acknowledge that you believe you have an important job to do in my life, and that your take your job seriously. Apparently your job is to induce complete panic whenever I’m about to do anything interesting – and, may I say, you are superb at your job. So by all means, keep doing your job, if you feel you must. But I will also be doing my job on this road trip, which is to work hard and stay focused. And Creativity will be doing its job, which is to remain stimulating and inspiring. There’s plenty of room in this vehicle for all of us, so make yourself at home, but understand this: Creativity and I are the only ones who will be making any decisions along the way. I recognize and respect that you are part of this family, and I will never exclude you from our activities, but still – your suggestions will never be followed. You’re allowed to have a seat, and you’re allowed to have a voice, but you are not allowed to have a vote. You’re not allowed to touch the road maps; you’re not allowed to suggest detours; you’re not allowed to fiddle with the temperature. Dude, you’re not even allowed to touch the radio. But above all else, my dear old familiar friend, you are absolutely forbidden to drive.”

If you’re on the fence between these two books, Big Magic is probably the better choice because Pressfield goes into some magical stuff at the end that I’m not really a fan of. That said, if you read one and like it, definitely pick up the other one too.

6. The E-Myth Revisited by Michael E. Gerber

As my business grew and I started hiring people, someone recommended The E-Myth to me.

I knew that I didn’t want to own a business that relied on me forever, but I also had the impression that service businesses were impossible for founders to get out of. I kind of assumed that I’d have to start a SaaS if I ever wanted to run a business that didn’t need me.

Gerber’s book gave me another path: the “franchise prototype.”

The Emyth encouraged me to think of my business as a system and to work on each part of it individually, finding people to fulfill specific roles rather than people who could do everything I could do.

By putting repeatable systems in place, I was able to scale my business very quickly ($0 to $2.5mm in revenue in just two years) while taking a month off completely when my second son was born.

7. The Obstacle Is the Way by Ryan Holiday

“Failure really can be an asset if what you’re trying to do is improve, learn, or do something new.” - Ryan Holiday

It’s easy to look back at my first three years of entrepreneurship now and see that things went remarkably well, but in the moment, it has rarely felt like that.

Entrepreneurship is full of rollercoaster ups and downs. I kept thinking that if I can just get over this next hill, it’ll all be easy, but that never seemed to be the case.

The Obstacle Is the Way is a reminder that every great success story follows this arc of apparent repeated failure and an eventual apparent success. People on the outside don’t see the struggles that got you through every day, they just see the end result, but when you’re living the challenges, they feel more real than anything else.

That said, facing hard things is the only way to grow.

Quitting when things get tough is a surefire path to mediocrity. Quitting is the easy way; it’s what most people do. Being exceptional requires failure and the temporary pain that comes with it.

Even if you don’t typically like motivational books, this one is worth a read.

8. How Will You Measure Your Life? by Clayton Christensen

As my business started to take off and I got myself out of much of the day-to-day, the next question I had to ask was, “Why am I doing this?”

At some point, every entrepreneur will have to answer this question, but most of them try to put this off for a long time. They might chase short-term goals like increasing revenue or profit, but these pursuits don’t answer the real question: why are you doing this?

I reference Christensen’s other book, The Innovator’s Dilemma, all the time, so when someone recommended How Will You Measure Your Life, I was excited to try it.

The book is much different from his other books; it’s essentially a series of lectures Christensen gave towards the end of his life about success and the meaning of life as he sees it. For me, it was especially interesting to hear how a man whose professional work I respected so much sees the real point of what he’s done.

Ultimately, this book led me on a search for something bigger, which took me on the first steps toward defining my big vision.

9. Buy Then Build by Walker Deibel

I was first exposed to “entrepreneurship through acquisition” a few years ago when I started guest lecturing at Northwestern’s Kellogg School of Business. A few of the students I met were running search funds with the intention of buying a small business that they could then run.

In 2022, as I started to define some bigger goals for myself, I came back to the topic, and decided that acquiring another business would be a faster and more certain way to grow than starting another business from scratch.

Deibel’s book basically lays out the playbook for acquisition entrepreneurship and is especially relevant if you’re looking to buy a service business like I was. It gave us a template that we could apply to our first acquisition and it’s still the book I recommend most when people ask about buying or selling a small business.

10. Unlimited Power by Tony Robbins

Unlimited Power book cover

Tony Robbins is a polarizing figure. On one hand, he’s incredibly successful, a gifted speaker, and a great storyteller. On the other, it’s easy to poke holes in his logic, he’s a bit verbose, and he’s given some questionable advice along the way (he was onced hospitalized for mercury poisoning because he ate so much tuna).

That said, many of the principles he talks about in Unlimited Power have impacted my operating system as a human. One idea that stands out to me most is the belief, action, results cycle.

While Robbins uses different words, I will try to summarize my takeaway:

  1. In order to achieve big things, you must believe that it is possible to achieve them. Without belief, you won’t take the next step…
  2. Massive action is required to achieve big things. Action is hard, so it requires belief, but if you take massive action, you will see…
  3. Outsized results that lead you closer to your big goals.

I want this cycle on a poster because I think about it every day.

11. The Gap and the Gain by Dan Sullivan and Dr. Benjamin Hardy

I’ve always been a high achiever, and like many acheivers, I don’t like to fail or miss my goals. This tends to lead me to setting goals that aren’t ambitious enough as a way to shield my ego.

While I’m still working on this, The Gap and the Gain helped me shift my perspective. The takeaway for me was that if you set a big goal and don’t reach it you have two options:

  1. See it as a failure by measuring how far off you were from the goal OR
  2. See it as a success by measuring how far you came from your starting point.

Seeing the gap without seeing the gain will lead you to constantly chase more and never be happy. Appreciating the progress you make will allow you to enjoy the journey much more.

12. The Alchemist by Paulo Coelho

I love a good allegory, so while friends have been recommending this book to me for years, I finally got around to it in 2023.

The Alchemist is the story of a young shepherd’s journey to find his “personal legend,” a great treasure that is revealed to him in a dream. Along the way, he meets others on the search for their personal legends and learns some universal truths about belief, fear, and having your own great pursuits.

As I’ve been on a journey to define my big vision this year, the book hit me at just the right time.

Some of my takeaways from the book include:

“People are capable, at any time in their lives, of doing what they dream of.”

“When you want something, all the universe conspires in helping you to achieve it.”

“There is only one thing that makes a dream impossible to achieve: the fear of failure.”

“Everyone seems to have a clear idea of how other people should lead their lives, but none about his or her own.”

“There is only one way to learn… It’s through action. Everything you need to know you have learned through your journey.”

If you like this kind of inspirational advice in story form, The Alchemist needs to be next on your list.

What’s Next?

I’ve always got a full backlog of books that people recommend to me, but I’m also always keeping an ear out for others. Find me on Twitter if you have your own suggestions or you liked this list.

Read more like this in Entrepreneurship, Books