Finding that perfect gift for your loved ones is a Herculean task during the holidays. Bombarded with endless sales and "best of" lists, it's hard to know where to start. I won't pretend to be able to help you with what to buy for your sister-in-law's cousin who's joining the family this year, but I can help if there are any entrepreneurs in your life. 

Entrepreneurs tend to be lifelong learners with an unquenchable thirst for information. They're always pushing themselves to grow, expanding the limits of what's possible, and challenging the status quo. The mental fortitude required to build something bigger than yourself can be isolating and difficult, which is why many entrepreneurs find solace in books

If you need a gift for the entrepreneur in your life, here are seven books that will make you look like the best gift-giver of all time. 

1. Ogilvy on Advertising by David Ogilvy (1985)

This book is a semester on advertising, business, and selling from the real-life Don Draper. It goes into excruciatingly wonderful detail on what works and what doesn't when it comes to advertising that sells - with lots of examples (and pictures).

The best part is Ogilvy is an insufferably arrogant British Man and the result is absolutely hilarious. "Any fool can fool can write a bad advertisement, but it takes a genius to take his hands off a good one. (p.67)." There's enough in here to keep you in business for 100 years. 

2. My Life In Advertising by Claude Hopkins (1927)

My Life In Advertising is like stepping into a time machine to the turn of the century where you get to walk around and feel what it was like to do business in the early 1900's. The irony is that not much has changed. Hopkins details timeless truths about human nature that are relevant to business today.

Not only is this a fantastic can't-put-it-down read, it's full of lessons that go far beyond advertising. Hopkins' genius was in how he saw the world, not the specific tactics he employed. Though, those were noteworthy as well: He pioneered in-store sampling, using ads to secure distribution, and using scarcity to manufacture demand. Household brands like Palmolive, Pepsodent, and Goodyear are only "household brands" because of him.

3. Scientific Advertising by Claude Hopkins (1923)

David Ogilvy said that "Nobody should be allowed to anything to do with advertising until he has read this book seven times." And I am inclined to agree. Scientific Advertising is a deceptively quick read is packed with insights that will change your business forever.

This book (and the ones above) purport to be about "advertising," but they're really about understanding people. Hopkins distills his decades of experience into this tiny book about the immutable laws of marketing. Despite being written in 1923, this book is as true today as it was back then.

Where most people gift the "latest" book that brings you "up-to-date" on trends, this book brings you back to the fundamentals. It grounds you in principles, instead of distracting you with the latest shiny object. Hopkins is concerned with one thing only: sales.

In a world that rewards vanity metrics, it's a refreshing reminder of what really matters for your business at the end of the day. 

4. War of Art by Steven Pressfield (2002)

If there is someone "creative" in your life who is ready to turn pro, buy. them. this. book.

Pressfield doesn't hold back in this honest peek into what it takes to be successful. The secret: Get your buns in that chair and get to work. Stop waiting for "inspiration" and take yourself, your work, and your craft seriously. 

Uplifting, but sobering, this book will transform how you approach your craft, your career, and yourself. Whether your "art" is software development, engineering, math, design, or writing - this book will be the catalyst that takes you from amateur to professional.

5. Small Giants by Bo Burlingham (2005)

Small Giants is a daring look at the companies that made the bold decision not to grow, expand, sell, or go public. This book challenges conventional notions of business success and showcases companies that value being exceptional, providing great service to customers, making contributions to their communities, having wonderful relationships with their suppliers, and choosing - above all - to stay small.

If you are looking to invent the future of business by staying privately owned, refusing to compromise on quality in exchange for scale, and instilling a sense of purpose and direction into your company - you won't be able to put this book down.

This book emancipated a generation of entrepreneurs from the restrictive "grow or die" mantra that has historically defined business success. If you have no interest in going public but aren't sure what options you have - this book will tell you.

6. Daring Greatly by Brene Brown (2012)

Another book that reads as smoothly as fiction, despite being about psychology, research, and data. You'd never know it. Brown is hilarious and honest in this in-depth look on her work on shame, vulnerability, and courage.

I know, you're thinking "cheesy. Pass." But you shouldn't. There's not a human on the planet who can't relate to this book (Daniel Pink, Simon Sinek, Seth Godin, and Oprah are among some of her famous fans). 

One thing entrepreneurs know for sure is that if they don't get their inner world together, their outer-world will be a mess. The two are connected. To be better at business (and life), you have to understand Brown's core message: vulnerability is the gateway to courage. Without courage, you cannot build a business (or, frankly, anything).

7. Anything You Want by Derek Sivers (2011)

Another short, but powerful book. Anything You Want is how Derek Sivers accidentally grew CD Baby to $22 million. Siver's philosophy is a manifesto for the next generation of entrepreneurs who see business as a way to help others and add value to the world. 

Siver's outlines non-intuitive business principles that define a new kind of entrepreneur, including, "Confidently exclude people," and "Don't try and make money." This book is responsible for inspiring a generation of entrepreneurs to care about their customers and be in business for the right reasons.

Buy Them Something They Won't Buy Themselves 

Many entrepreneurs are voracious readers making it hard to know what books they've already read. I've chosen books that are less well-known (and certainly, older) for that reason.

You can assume your gift recipient has read The Lean Startup, Good To Great, How To Win Friends and Influence People, Influence, and Built to Last. But it's unlikely they've read the books on this list. And in the rare case that they have, they'll be glad to have a second copy. 

Happy Holidays.

Published on: Dec 13, 2017
The opinions expressed here by columnists are their own, not those of