Nine business books that will change the way you think

Colm Larkin

November 12, 2015

Hightail recommends business books

With so many ways to sharpen your business brain just a click away, business books can seem archaic when compared to blog posts, webinars and Ted Talk videos.

But we tend to consume digital content in bite-sizes before jumping back into our next task or meeting. Spending time with a book allows you to immerse yourself fully in its concepts, tactics and strategies and provides more mental space for thinking about how new ideas could translate to your business.

That’s why we asked nine Hightail employees to recommend their favorite business book and explain how it made them think differently about the way they work. Read on…

Presentation Zen by Garr Reynolds Presentation Zen by Garr Reynolds
Recommended by Ranjith Kumaran – CEO

RK: I was doing a lot of public speaking a few years ago about starting companies and came across this book. Reynolds breaks down how people process visual information and I immediately started applying the concepts. Not only did my sessions stand out more, I found that it was a fun process to build the materials. Here’s the first set of slides I created incorporating techniques from the book. 

Biggest take-away: without the speaker present a slide deck should not make any sense, those are called handouts and should be prepared separately.

Zero to One by Peter Thiel Zero to One by Peter Thiel (with Blake Masters)
Recommended by Mike Trigg – Chief Operating Officer

MT: Peter Thiel is the co-founder/CEO of PayPal and Palantir and VC investor in Founders Fund. I like his approach to building companies that have huge market power (think Google or Facebook) and become incredibly fast growing, profitable and valuable. The four keys he identifies to achieving that kind of monopoly-esque power are:

1. Technical innovation: usually 10X better than existing alternatives
2. Network effect: use of your product drives viral adoption by more new users and increases the value to all users
3. Scalability: to keep up with skyrocketing demand
4. Brand

These factors are important for businesses of any size and have influenced my thinking about what we’re doing at Hightail.

The Hard Thing about Hard Things by Ben HorowitzThe Hard Thing about Hard Things by Ben Horowitz
Recommended by Britt Montalvo – VP of Marketing

BM: This book shows the unique challenges faced by tech entrepreneur and investor Ben Horowitz when running various companies and how he and his team managed their way out of them. It also gives great insight into the types of people you need for companies in good and bad times. Horowitz is an incredibly smart and down to earth writer, which makes for a captivating and inspiring book.

The Design of Everyday Things by Don NormanThe Design of Everyday Things by Don Norman
Recommended by David Louie – UX Designer

DL: I read this book more than 10 years ago, when I was a front-end web developer with an interest in how people used the web sites we were building. Because it’s focus is on ‘how things work’ and not ‘how they look’ the book allowed me to imagine myself becoming a Designer. It was a gateway into new worlds of user experience and human-centered design. Because the case studies are everyday objects, the book also illuminates how every human made object in the world is ‘designed’, but some with more attention to human needs and capabilities.

Whenever I meet people that are interested in design, but don’t imagine themselves as ‘artistic’ I recommend this book.

The Boys in the Boat by Daniel James Brown The Boys in the Boat by Daniel James Brown
Recommended by David Beckwith – VP, Business and Corporate Development

DB: It isn’t a business book, but the real-life quest of a US rowing team to compete at the 1936 Berlin Olympics is an inspiring story that involves team effort, hard work, long odds and finding motivation in unusual places. It reminds me to be open to inspiration and learnings from others, often from those you least expect. It’s also beautifully written and I am a fan of finding just the right words (written or spoken) for important situations, particularly in business.

Lean In by Sheryl SandbergLean In by Sheryl Sandberg
Recommended by Sherrie Stifter – Senior Recruiter

SS: What I found really inspiring about this book was Sheryl Sandberg’s belief that though you may not be the CEO of your company, you should still act like one. I have found this to be true over and over in my professional life. It requires the ability to focus on what’s next in your career (notice I didn’t say “job”); what’s next in your role at work, what’s next in my department, etc. Asking these statement-type questions helps you to “lean in” to management and “lean in” to your career, because at the end of the day, you’re investing in YOU.

Freakonomics by Stephen D. Levitt and Stephen J. DubnerFreakonomics by Steven D. Levitt and Stephen J. Dubner
Recommended by Matt Miles – Finance Manager

MM: While it may not be the most traditional business book, I am a big fan of Freakonomics (and its follow-ups Freakonomics, Superfreakonomics, Think Like a Freak and even the podcast). The book is filled with true stories about data analysis that question conventional wisdom. For me, it highlights the value of asking the right questions when making decisions and the importance of understanding what data you’re analyzing and how you’re measuring it. This is helpful in my day-to-day job of analyzing data sets, where I’m asking questions to find causation vs. correlation. But it’s also equally helpful at the macro level: am I asking the right questions to support the strategy of the company?

Universal Methods of Design by Bella Martin and Bruce HaningtonUniversal Methods of Design by Bella Martin and Bruce Hanington
Recommended by Kiersten Lammerding – Principal UX Designer

KL: I wish someone had given me this book when I graduated from college. It offers a collection of design methods that can be applied to one of five generalized design phases. These are quick and digestible methods that individuals or teams can use to attack problems from start to finish. Many of the methods are applicable not to just design problem solving, but useful for engineering and business as well and allow you to move quicker and attack problems from more angles than traditional user research.

Start With Why by Simon Sinek Start With Why by Simon Sinek
Recommended by Scott Moe – Senior Director, Marketing

SM: This book is more interesting and inspiring than most business books I have read. Simon Sinek spoke at a leadership conference at one of my past companies and one of the things I found intriguing was his use of non-business examples (Sir Ernest Shackleton, Dr. Martin Luther King Jr., the Wright brothers) to demonstrate his theories. Being clear in your purpose and knowing why you are doing what you are doing allows everyone to understand. People will work harder, be more passionate and ultimately drive your success if they are able to connect with you on a more emotional level. It’s a good lesson and one I try to factor into my decision making process regularly to make sure I am doing things I am passionate about.

Which business books have changed the way you think? We’d love to hear your recommendations in the comments below.


  1. Joel Badie

    3 years ago

    Great post!

  2. Pherry C Mwiinga

    3 years ago

    I am excited about these books! What does it take to get them??

  3. kavik

    3 years ago

    So nice

  4. Victor

    3 years ago

    Interesting, but they’re mostly books in Hightail’s own internet/tech field and not really business as a whole as the title of the article implies. As with most companies, you live in your own little world and what’s relevant to you and the guy down the hall. I will say, however, that your site is much more user friendly and customer friendly than most IT companies.

  5. Colm Larkin

    3 years ago

    Hey Victor. Thanks for your nice comments about our site. I’m surprised you find our list to be tech-centric – after all, one of the books is about a rowing team from the 1930s – but glad you found it interesting.

  6. stan adler

    3 years ago

    If there are copies available used or otherwise on Amazon,, and other commercial book sites, buy a copy of The Zen of Selling by Stan Adler. It’s a book of stories that will illustrate the essential things you need to know to sell goods or ideas.

  7. Nayaz

    3 years ago

    We are all so busy in our own industries that we fail to notice what’s going on around us in other industries. And there is a lot we can learn from applying techniques used in industries different from ours.
    Thank you for this list of books. There is always something new we can try to improve our businesses and hopefully we can get some ideas by reading these books.

  8. Jodi

    3 years ago

    Well, after reading this I have so far bought three books out of the list! I’ll save the links and probably the buy the rest at a later stage, but this should keep me going for a bit. These are really interesting suggestions and I can see how, even from this brief overview, there is much to learn.

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