Best Ecommerce Books for Business Leaders (Hint: They’re Not Necessarily About Ecommerce)


“Books,” wrote Charles William Eliot, “are the quietest and most constant of friends; they are the most accessible and wisest of counselors, and the most patient of teachers.”

At the risk of contradicting Harvard’s most distinguished president, I’d like to add a caveat: Certainly, books are friends, counselors, and teachers.

However, books—particularly the best books for leaders—are anything but quiet. At least, they shouldn’t be.

Getting books to speak up takes effort. As my friend Jesse Wisnewski recently noted in The Observer:

“Reading isn’t the same as having a face-to-face conversation with someone you want to learn from.

“But if you want to learn lessons from the books you read, then you must become an active reader: someone who is ready to ask questions, review their notes, and then take action. This shift in the way you approach what you read will help you to treat books like your best mentors.”

To that end, we reached out to 10 of the best mentors in the ecommerce space and asked them for the best ecommerce books leaders should read, along with the best lessons and quotes from that book.

But, don’t be fooled. These aren’t books about ecommerce—not all of them anyway. Nor are they a round-up of last year’s most famous titles.

Instead, these books, lessons, and quotes span the worlds of business, sociology, history, psychology, and customer service. So, let’s explore.

1. Shoe Dog by Phil Knight

Shoe Dog - Phil Knight book cover

Recommended by Tobias Lütke, Shopify’s Chief Executive Officer

From Phil Knight’s humble origins—selling $8,000 his first year from the trunk of a Plymouth Valiant—to topping $30 billion at the time of publication, Shoe Dog: A Memoir by the Creator of Nike offers an autobiographical account of one of the world’s most recognizable brands. 

Best leadership lesson:

“War is the most extreme of conditions. But business has its warlike parallels. Someone somewhere once said that business is war without bullets, and I tended to agree.

“One lesson I took from all my home-schooling about heroes was that they didn’t say much. None was a blabbermouth. None micromanaged.

2. The Obstacle Is the Way by Ryan Holiday

The Obstacle is the Way - Ryan Holiday book cover

Recommended by Harley Finkelstein, Shopify’s Chief Operating Officer

Drawing inspiration from Marcus Aurelius’ 2,000-year-old quote, “The impediment to action advances action. What stands in the way becomes the way.” The Obstacle Is the Way leads modern readers into the ancient Greek philosophy of stoicism. “The Stoic,” Holiday says, “doesn’t look out at the world and try to change it; they try to change themselves—to orient themselves to be the best person they can in that world.” 

Best leadership lesson:

“Failure really can be an asset if what you’re trying to do is improve, learn, or do something new. It’s the preceding feature of nearly all successes.

“There’s nothing shameful about being wrong, about changing course. Each time it happens we have new options. Problems become opportunities. And that means changing the relationship with failure. It means iterating, failing, and improving.

3. The Subtle Art of Not Giving a F*ck by Mark Manson

The Subtle Art of Not Giving a F*ck - Mark Manson

Recommended by Brittany Forsyth, Senior VP of Human Resources at Shopify

Mark Manson’s 2016 best-seller, The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life, is a generation-defining antidote to popular wisdom on positive thinking. Dripping with raw honesty and an indomitable spirit, the book deserves a place not only on every leader’s shelf but also within their hearts and minds. 

Best leadership lesson:

“Everything worthwhile in life is won through surmounting the associated negative experience. Any attempt to escape the negative, to avoid it or quash it or silence it, only backfires.

“The avoidance of suffering is a form of suffering. The avoidance of struggle is a struggle. The denial of failure is a failure. Hiding what is shameful is itself a form of shame.

“Pain is an inextricable thread in the fabric of life, and to tear it out is not only impossible, but destructive: attempting to tear it out unravels everything else with it.

4. Sapiens by Yuval Harari

Sapiens - Yuval Noah Harari

Recommended by Loren Padelford, General Manager of Shopify Plus

Few books contain as grand a scope as Sapiens: A Brief History of Humankind. Dr. Yuval Harari’s sweeping narrative begins roughly 70,000 years in the past with “the appearance of modern cognition” and unfolds as a metanarrative merging science, geopolitical economics, religion, and philosophy.

Best leadership lesson:

“Findings demonstrate that happiness is not the surplus of pleasant over unpleasant moments. Rather, happiness consists in seeing one’s life in its entirety as meaningful and worthwhile. There is an important cognitive and ethical component to happiness.

“Our values make all the difference to whether we see ourselves as ‘miserable slaves to a baby dictator’ or as ‘lovingly nurturing a new life.’ As Nietzsche put it, if you have a why to live, you can bear almost any how.

5. Originals by Adam Grant

Originals- Adam Grant book cover

Recommended by Hana Abaza, Head of Marketing at Shopify Plus

Where do new products, policies, and ideas come from? How do they take root? Why do some survive, while others fall by the wayside? And what does it mean to be “original”? With more accolades and awards than can be mentioned, in Originals: How Non-Conformists Move the World Adam Grant answers all these questions with a mix of narratives and quantitative studies.

Best leadership lesson:

“If you’re expressing a fierce conviction, you should be forthright about it— but know that your colleagues will probe the quality of your reasoning. Even then, you’re supposed to be assertive and open-minded at the same time. 

“As management scholar Karl Weick advises,

‘Argue like you’re right and listen like you’re wrong.’

6. The Hard Thing About Hard Things by Ben Horowitz


Recommended by Craig Miller, formerly Shopify’s Chief Product Officer

Originally published in 2014, The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers immediately established itself as a modern classic. Amidst our culture’s fascination with starting a business, Ben Horowitz analyzes the far more difficult issues that confront leaders running a business.

Best leadership lesson:

“Figuring out the right product is the innovator’s job, not the customer’s job. The customer only knows what she thinks she wants based on her experience with the current product.

"The innovator can take into account everything that’s possible, but often must go against what she knows to be true. As a result, innovation requires a combination of knowledge, skill, and courage."

7. Creativity Inc. by Ed Catmull

Creativity - Ed Catmull

Recommended by Lynsey Thornton, VP of User Experience

Part artist, part technologist, part entrepreneur … Ed Catmull’s presidency at both Pixar and Disney Animation Studios has amassed $11.7 billion in worldwide ticket sales. Creativity Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration leads readers through Catmull’s own counterintuitive path to success as well as their own.

Best leadership lesson:

“This principle eludes most people, but it is critical: You are not your idea, and if you identify too closely with your ideas, you will take offense when they are challenged. To set up a healthy feedback system, you must remove power dynamics from the equation—you must enable yourself, in other words, to focus on the problem, not the person.”

8. Competing Against Luck by Clayton M. Christensen

Competing against luck - Clayton Christensen

Recommended by David Moellenkamp, Director of Product at Shopify

Few names are as synonymous with innovation as Clayton Christensen. Co-author of The Innovator's Dilemma and The Innovator’s Solution, Christensen’s Competing Against Luck: The Story of Innovation and Customer Choice continues that same disruptive journey with a new twist: “our long-held maxim — that understanding the customer is the crux of innovation — is wrong.”

Best leadership lesson:

“When we buy a product, we essentially ‘hire’ something to get a job done. If it does the job well, when we are confronted with the same job, we hire that same product again. And if the product does a crummy job, we ‘fire’ it and look around for something else we might hire to solve the problem.”

9. The Best Service is No Service by Bill Price and‎ David Jaffe

The Best Service is No Service

Recommended by Gregory Ciotti, Shopify’s Content Marketing Lead

Not only does Bill Price and David Jaffe’s textbook, The Best Service is No Service: How to Liberate Your Customers from Customer Service, Keep Them Happy, and Control Costs, boasts the longest title and oldest publication date on this list, it is also a tour de force for ecommerce leaders looking to revolutionize the way their companies treat and retain customers.

Best leadership lesson:

“They would either prefer not to make contact at all or, in many situations, prefer the flexibility and convenience of well-designed self-service that they can use whenever they have the time, or of proactive alerts to them before an issue becomes serious.”

10. Mindset by Carol Dweck

The Best Service is No Service

Recommended by Katie Keita, Investor Relations at Shopify

After decades of research, Stanford University psychologist Carol Dweck’s Mindset: The New Psychology of Success created a new vocabulary for motivation, leadership, and productivity.

Best leadership lesson:

“This growth mindset is based on the belief that your basic qualities are things you can cultivate through your efforts, your strategies, and help from others … people with this mindset … believe that a person’s true potential is unknown (and unknowable).

It’s impossible to foresee what can be accomplished with years of passion, toil, and training.

Two Mindsets

What are the best ecommerce books for leaders?

  1. Shoe Dog: A Memoir by the Creator of Nike by Phil Knight
  2. The Obstacle Is the Way by Ryan Holiday
  3. The Subtle Art of Not Giving a F*ck by Mark Manson
  4. Sapiens: A Brief History of Humankind by Yuval Harari
  5. Originals: How Non-Conformists Move the World by Adam Grant
  6. The Hard Thing About Hard Things by Ben Horowitz
  7. Creativity Inc. by Ed Catmull
  8. Competing Against Luck by Clayton M. Christensen
  9. The Best Service is No Service by Bill Price and‎ David Jaffe
  10. Mindset: The New Psychology of Success by Carol Dweck

To be sure, books are friends, counselors, and teachers. But books don’t speak for themselves. Instead, as Jesse Wisnewski put it, to make even the best books our mentors, we must ask questions, take notes, and—above all—take action.

Of course, there’s always a chance we missed your best-book recommendation.

If we did, let us know in the comments, and be sure to include at least one lesson as an introduction to what might be our next great mentor.

About the author

Aaron Orendorff

Previously the Editor in Chief of Shopify Plus, Aaron Orendorff is the VP of Marketing at Common Thread Collective. Named by Forbes as one of the top 10 B2B content marketers, his work has appeared on Mashable, Entrepreneur, Business Insider, Fast Company, Inc., Success Magazine, The Next Web, Content Marketing Institute, and more.

Check out Aaron Orendorff’s work