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11 Best Books to Gift Entrepreneurs During the Holidays

6 Mins read

Here are 11 answers to the question, “What is one of the best books to gift entrepreneurs during the holidays? “

  1. Never Split the Difference by Chris Voss
  2. Clockwork by Mike Michalowicz
  3. The 7 Habits of Highly Effective People by Stephen R. Covey
  4. The Lean Startup by Eric Ries
  5. Shoe Dog: a Memoir by the Creator of Nike by Phil Knight
  6. The Happiness Advantage by Shawn Acor
  7. Poke the Box by Seth Godin
  8. Start With Why by Simon Sinek
  9. Rework by Jason Fried and David Heinemeier Hansson
  10. Bad Blood by John Carreyrou
  11. Powerful by Patty McCord

Never Split the Difference by Chris Voss

Effective marketing is centered on the ability to be persuasive, and this is the focus of Chris Voss’s book Never Split the Difference, making it the perfect gift for any entrepreneur during the holiday season. 

Marketers continually try to influence their audience to take actions that will lead them into the sales funnel, but success is not dependent on a product or the quality of service, but being able to convince the customer of their need for them.

Voss deftly explains the techniques of FBI negotiators and then creatively applies them to the world of business relations, marketing, and operations. He carefully segments each component in its simplest form, so it can apply to almost any endeavor. 

Never Split the Difference is at the heart of all marketing, and its techniques and methodologies make it the ideal gift for any entrepreneur.

Greg Gillman, Chief Revenue Officer, MuteSix

Clockwork by Mike Michalowicz

The book provides an excellent framework for creating a profitable business that runs by itself. 

It walks readers through the three essential steps for building a self-running business: hiring the right people, systems, and processes, and getting out of the way. Hiring is often one of the most challenging tasks for entrepreneurs. Many entrepreneurs find themselves so bogged down in the day-to-day details of running their business that they only sometimes get to step back and work on their business instead of in it. 

This can be a difficult transition for many entrepreneurs, but it’s essential if they want to create a genuinely self-running business.

Michael Sena, Founder & CEO, Senacea

The 7 Habits of Highly Effective People by Stephen R. Covey

The Seven Habits of Highly Effective People by Stephen R. Covey is one of my all-time favorite business books, and its lessons have been coming to mind more and more as we approach the end of the year. 

It offers insightful direction on making impactful personal changes. Among other lessons, this book inspired me to become more proactive, set clear goals, and make time for refreshing activities and self-care. Every time I hire a new employee at my medical practice, I give them a hard copy of this book.

Jae Pak, MD, Jae Pak MD Medical

The Lean Startup by Eric Ries

The Lean Startup: How Constant Innovation Creates Radically Successful Businesses by Eric Ries is an excellent choice for entrepreneurs. 

This book provides a scientific approach to creating and managing startups and can help readers understand running a successful business. It covers topics such as understanding customer development, establishing metrics, setting up experiments, testing hypotheses, and using validated learning to make decisions. 

It is also full of useful advice and strategies on how to create a successful business, manage risk, and maintain agility. The Lean Startup is a must-read for any entrepreneur looking to take their business idea to the next level.

Amira Irfan, Founder & CEO, A Self Guru

Shoe Dog: A Memoir by the Creator of Nike by Phil Knight

Today, even the most remote markets in the world know of Nike as a globally renowned brand, but very few know of the struggles that Phil Knight went through in making his brand the success it is today. 

Going up against the giants in the business and winning one entrepreneurial battle after another is no easy feat, and Knight shares his journey with lessons that every entrepreneur can put to use in their own entrepreneurial skirmishes. 

A book that even Bill Gates termed an “amazing tale,” this one is just the inspiration entrepreneurs need to transform their struggles into success.

Kris Harris, Owner, Nootka Saunas

The Happiness Advantage by Shawn Acor

Too often as an entrepreneur, it’s easy to love work but not be truly happy there. The Happiness Advantage: How a Positive Brain Fuels Success in Work and Life by Shawn Acor brings happiness back to the forefront of your time at the office and in life itself.  

It provides a construct for how to reframe your thinking to be happy, not just for a day, but as a lifestyle. An entrepreneur learning this lesson can then teach it to their employees for joyful company culture. 

Happiness is increasingly seen as a science, and this book is a professor of it. The Happiness Advantage is a great holiday gift for an entrepreneur who could use a little boost.

Temoer Terry, Partner, Mommy Care Kit

Poke the Box by Seth Godin

The holiday season marks the end of the year and the beginning of a new one—making it a great time to set new goals and some renewed motivation. 

This is why the book Poke the Box is the perfect gift. It takes on an encouraging and passionate voice and asks you to stop waiting to go after those goals you had set early on. Seth Godin encourages you to get curious, try something new and truly go all in with your passions.

Asma Hafejee, Sr. Marketing Executive, CMR Surgical

Start With Why by Simon Sinek

In my opinion, entrepreneurship involves selling your idea and your concept of a product or service to your customers. This requires leadership. The best book to inspire leaders is Start with Why by Simon Sinek. 

Most people and businesses know what to do and how to do it. However, very few of them can articulate “why” they do what they do: think, act, and communicate in a way that gives not only them a sense of purpose and a greater drive to succeed.

This also is at the forefront with their customers and followers. Businesses with a greater and more loyal customer base understand people won’t buy their product, service, or idea until they understand the why behind it.

Alan Carr, Director, Webpop Design

Rework by Jason Fried and David Heinemeier Hansson

The end of the year and holiday season call for a push into a new perspective with entrepreneurship. 

A profoundly practical approach to making it on your own can give someone exactly the perspective they need to get started. The book strips everything down to its bare essentials and shows the reader that you don’t need more to achieve more. 

You can close this book with a feeling of renewed motivation and a clearer idea about how you can achieve your goals.

Larissa Pickens, Owner, Repeat Replay

Bad Blood by John Carreyrou

There are so many books out there that provide detailed accounts of some of the greatest entrepreneurial success stories in U.S. history. But there was one book that came out during the past few years that really did a thorough analysis of one of the worst entrepreneurial endeavors of all time. 

Bad Blood: Secrets and Lies in a Silicon Valley Startup should go down as one of the best books about entrepreneurship ever written. John Carreyrou wrote it like a thriller. It’s a literal page-turner. And it’s about the fall of an ambitious woman who thought she could revolutionize how diseases are diagnosed.

People paid a significant price for her hubris and lies. And it’s a timely book, too, considering the recent prison sentence handed down for the woman (Elizabeth Holmes) who is the centerpiece of the book. There’s no better book out there that outlines what not to do if you’re an entrepreneur.

Emily Saunders, Chief Revenue Officer, eLuxury

Powerful by Patty McCord

Patty McCord’s book Powerful is a must-read this holiday season for every entrepreneur trying to expand their firm. And it is a former Netflix human resources executive.

Besides, she also appears on the TED stage. This book explains how she converted Netflix from the most despised corporation to one of the most appreciated. Patty goes into great depth in this book on how she transformed the firm’s culture and maintained a pleasing workplace.

What’s fantastic about this book is that it’s really easy to read and has many personal experiences. This book is for anyone searching for a decent read about the corporate world.

Khanh Tran, Growth Manager, Villa Finder


Brett Farmiloe is the founder of Terkel, a Q&A platform that connects brands with expert insights.

Gift book stock image by Hafiez Razali/Shutterstock

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