10 Books Every Entrepreneur Should Read

10 Books Every Entrepreneur Should Read

In this post, I’m going to introduce you to the list of 10 books every entrepreneur should read. I’d also recommend them to any small business owner, sole proprietor, or even manager at a larger company. These are all books that I’ve personally read and found to be helpful in my journey as a small business owner.



The Transition

There may come a time when you’re thinking of starting your own company.  In my case it was creating websites and exploring other web technologies.  These books are helpful when you’re at this stage.


The Principles of Successful Freelancing

Admittedly, it’s been a while since I’ve read this book.  If you’re in the very beginning stages of thinking about starting your own business, this book is general enough and gives you some things to think about, from the business process, to handling money, charging clients, etc.  It was written in 2008, but I think it’s general enough you can trigger ideas in your mind and get some clarity from the thought of owning your own business to actually starting it.


Starting Your Career as a Freelance Web Designer

This book is more focused towards running a web business.  I personally hate to call myself a Web Designer…I feel I’m more of a developer since I lack some creative thinking when looking at a blank slate to call myself a designer, though I do design and make design recommendations regularly with my business.  Don’t let the title trip you up.  This book was written in 2011, and if you’re in the web industry, you know that’s a LONG time ago.  Things change so rapidly.  However, I was able to grab some ideas, similar to the book above, about running my business.  From financing, testing a website, how to approach a client, creating a proposal, project management, creating a niche, to talk about taxes – the business side of web development / design business.  I found that there were elements of the sales cycle I wasn’t aware of.  There’s no checklist saying “do your taxes like this”, “write your proposal like this” (kind of, though), “write your business processes like this”.  I’ve come up with my own solutions, like putting 30% of all income aside, business processes where I write the processes in Google Docs, etc.  I’m focusing on a market of business where I’m basically a contractor for other companies.  The sales cycle isn’t something I’m that great at, and it takes a lot of time.  I would suggest this book to get you thinking about actually running the business, and I think you can grab a lot even if you’re not going to run a web design business.



Actively in Business

When you’re actively in business, there will be good times and bad times.  I really think businesses close because you fall out of love with what you’re doing.  It can be overwhelming, and sometimes you just need to be inspired.  I’m recommending these books, most of them inspirational books, and a marketing book.


Guerilla Marketing

Jay Conrad Levinson has been writing these books for a while and there are a few editions.  The book does go from topic to topic rather quickly, but there are PLENTY of cheap and free marketing ideas that are creative and can help set your business apart.  These are great for those who are just starting and have less capital to spend.


The Millionaire Fastlane

To be honest, I thought this book would be a little fantasy.  Not like a Lord of the Rings book, but fantasy as in the thought that I can never be a millionaire.  The verdict is still out on that.  The author, MJ DeMarco, talks about how it happened for him.  To be honest, and I think he talks in this direction too, he was in the right place at the right time.  He started a business and got into making websites when they were really just starting to make money for normal people, not just news outlets and eBay – it was in the 1990s, the dot com boom.  I really wish I had the skills I have now back then because it seems like he priced (and people were fine with paying) the same prices I’m charging today.  There was a lot less actual work to do than there is now – clients expect so much more.  Anyway, back to the book.  He’s down to earth and I felt like I could relate to him a lot.  He tried many different jobs, all over the place, not really sure what he wanted to do, and the business kind of fell in his lap.  The smart and hard part was doing it right and maintaining and growing the business.  I’m going to go back through some of my notes on this book and update this post.  This book really had a TON of very inspirational thoughts that excited me.  Life isn’t all about money, but if you’re going to work, you might as well have your money work for you so you’re not working forever – so you can have that work-life balance.  That’s what I got out of this book, and again, I’m going to update this post to include some examples!



I remember starting this book on a plane ride from Raleigh, NC to Rochester, NY, where I grew up.  I felt very excited to read on the 2 plane rides, and I couldn’t wait to continue reading.  The author, Jon Acuff, has an interesting theory about the stages of your career, and if you think about it, he’s right on…I’ve just never thought about it before reading this book.  He says in your 20s you’re in the Learning phase, in your 30s you’re Editing what you’ve learned, and so on.  You’ll have to read the book to find out the other stages.  He talks about removing the decades of your life from the stages and accelerating them.  He asks questions so you can gauge yourself, which I thought was helpful.  One thing about this book that’s more about my personal situation running a web development business – I hate when people get the idea that making a website is so “easy”, like he and his friend did.  They went and charged an absurd amount of money that their client agreed to.  I guess there I go again being sour because I haven’t reached that in my business, and I think it has to do with sales.  I already understand and know there are plenty of clients with large pockets, but to close the deal and get the income is what I’m failing at right now.  Long story short, he got in over his head and returned the money to that client.


Street Smarts

I read the revised version of this book, released in 2010.  It’s written by 2 people from NY and I could sense the arrogance in some places in the book – I think even at one point they talk about being hot headed, especially when they were younger.  I wasn’t clear who was talking when, it’s written more like a one author book, but it’s labeled with 2 authors.  Anyway, the book is about how he ran a document storage business.  He goes through ups and down, he does seem ahead of the curve all throughout his career – at one point, in the 1980s I think, he invests in a state-of-the-art tracking system that he had custom programmed.  Though I’m not in the storage business, I still found this book very inspiring, and it unlocked some thoughts in my head for if I ever do have employees of my own.


The Entrepreneur Roller Coaster

My wife just got this book for me for Christmas.  I’m really loving it so far.  I can’t write about the whole book yet, but I like how the book takes quotes from famous people and incorporates part of a chapter into expanding on that thought.  He writes some thoughts on how to find what you’re passionate about and the way the author, Darren Hardy, writes, it makes you really feel in the thought of what the chapter or section is about.  He talks about how NOW is the time to do what you want to do and I just got through the section where he talks about hugely famous names and their backgrounds – like not finishing college, and humble beginnings.  I’m at the section where he was doing really well in his career and he wanted to impress his dad by showing him the dream house he just bought, but all his dad could notice is a water stain in the ceiling.  I feel bad for him, his dad sounds like a real jerk – but he takes that situation and discusses how YOU define what success means to you, and that was part of his (emotional) roller coaster.  I’ll update this post as I get further through the book!



Lower Priority

These are books that get a lot of press, but aren’t necessarily the best out there, in my opinion.


Double Your Freelancing Rate

I think it was 2011 or 2012 when the first version of DYFR came out.  I was really excited, because I was working full time at a social media company, and I really wanted to get out and do my own thing.  I was freelancing on the side, but I had no confidence in what to charge my clients.  I was in a total employee mindset.  This was the first book I read when I was starting my journey.  Though I did get some tips to gain some confidence and I do think overall it’s a good book, at the end I felt like I didn’t get as much value as I was expecting.  When version 2 came out, I was hyped up and bought it immediately too.  Again, it was a short read, said about the same thing as the first version, and I was about another $50 or so.  It’s really hard to find this book on discount.  If you haven’t been able to figure it out, I’m saying it’s a good book, but it’s priced too high.  I respect what Brennan Dunn does in terms of giving tips and being apart of a community.  Maybe I’m just sour and a little jealous that I’m not in his position.  Either way, if you’ve got the money you can read it, but it is a little expensive for an ebook.


The Blueprint

Lesser known of Brennan Dunn’s 2 books, I did do the DIY version of the book.  There is (or was) a plan where he would sit with you and/or provide feedback – like a mentor.  You could see it as a cheap mentor in the long run, and I can’t speak to that area since I elected not to pay for that.  I do know that he’s actively built and maintained a community and at one point we exchanged emails, his response was quick.  Like DYFR, I just felt like it was priced high and didn’t get the value at the end.  I had questions that I wish the book would have explained (though I’d have to re-read it to tell you a specific situation).  I didn’t want to go to the community or email to get those answers, I wanted the book to go into more depth.  He did have a nice drip system set up after I purchased this ebook, though, and he sent out goals and other emails, which helps keep you in line with your dream of owning a business.  Same as Double Your Freelancing Rate – if you’ve got the money, it’s worth a read.


The 4 Hour Work Week

I love the idea of working 4 hours a week.  However, I was really disappointed with this book.  Without giving away too much, it basically is about running a “business” of outsourcing everything.  Your work week is maintaining the outsourced work.  That’s not really a business, at least in my eyes.  And I really feel like even if that’s what you do, you’d have to spend more than 4 hours a week.  Quick response is a huge factor that my clients love about working with me – and if I was only available 4 hours a week, my response rate would be really slow (what I feel is bad customer service), and my inbox would be smashed with tickets, emails, etc, that I have to put in order and actually process – since I don’t outsource my work.


Did I miss any great books that are helpful for entrepreneurs? I’d love to hear your recommendations!