The Top 12 Books Every Entrepreneur Should Read This Year

One book for each month, customized for the seasons

January 13, 2021

One book for each month, customized for the seasons

As a full-time author, filmmaker, and blogger, I spend a huge amount of time reading every day. Rather than watch shows on the weekend, my wife and I actually set aside Sunday afternoons for hardcore binge-reading by the fire.

What follows is 12 of my favorite books of all time. It’s probably not your standard list for marketers, but each book will be hugely beneficial to you if you’re a marketer, creative, entrepreneur, or maker. Zero Amazon affiliate links here — just a dozen great books to read this year, suited for each month and season. Have fun exploring!

January

On the Shortness of Life by Lucius Annaeus Seneca

The word January comes from the ancient two-headed god Janus, who’s often depicted with one head looking back and one head looking forward. It’s a good posture for us to take in this first month of the new year, to stop and reflect on what’s truly important in life.

Ease into the new year with a tiny book with a profound message: Time is short, and you shouldn’t waste another second of it.

The best marketers are those who know their priorities and devote themselves to a just few great endeavors. Think of Elon Musk, Steve Jobs, P. T. Barnum.

Purposely building awareness of life’s shortness creates a time pressure that propels many leaders to make every day count. That’s why I re-read this wonderful and gorgeous pocket-sized book every single year.

February

The days are short and the snow is deep— will it ever end? Make it through the depths of winter with a book filled with upbeat stories and a timeless message: The best way to market anything is to tell a great story.

Guber’s the real deal and marketers should pay attention. As the former chairman of Sony Pictures and current CEO of Mandalay Entertainment Group, he produced Rain Man, Batman, Flashdance, and dozens more, amassing $3+ billion at the box office and 50 Academy Award nominations. (He also co-owns four professional sports teams.) His secret? Tell to win.

“Historically, stories have always been igniters of action, moving people to do things. But only recently has it become clear that purposeful stories — those created with a specific mission in mind — are absolutely essential in persuading others to support a vision, dream or cause.” — Peter Guber

March

32 Ways to Be a Champion in Business by Earvin “Magic” Johnson

I adored this book, despite the cheesy title. As March shakes off winter and green things start to re-emerge, this excellent memoir will serve as a source of creative inspiration in your own life.

It’s rare for professional athletes to remain financially successful when the gravy train stops rolling, but Magic has proved just as exceptional off the court as on it, amassing a net worth north of $600 million. Magic Johnson Enterprises specifically focuses its investments in underprivileged areas and even loaned $100 million to minority- and women-owned businesses that were excluded from PPP loans.

Magic is a born marketer, and 32 Ways is a masterclass in selling with style. Some of his stories are wild, like the time an inner-city gang threatened him… and he hired them instead.

April

The War of Art by Steven Pressfield

Like gardening in springtime or tackling your house/garage/minivan for a deep spring cleaning, creating great work is hard work, and the tendency is to procrastinate and delay until it’s too late. Pressfield lays out the path to make it through the minefields that stand between the initial idea and the marketable finished product.

“Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it.” — Steven Pressfield

May

Let Your Life Speak by Parker Palmer

Now that the flowers are starting to bloom and everything is bursting into life, now’s the time to see the life that’s growing in you.

“Before you tell your life what you intend to do with it, listen for what it intends to do with you. Before you tell your life what truths and values you have decided to live up to, let your life tell you what truths you embody, what values you represent… Before I can tell my life what I want to do with it, I must listen to my life telling me who I am.” — Parker Palmer

The best marketers are the honest ones. The funny ones. The authentic ones. They’re real people, not personality-less pitchmen, the human equivalent of a stock photo. Let Your Life Speak is a winsome book about listening for the voice of vocation. This book was very helpful on my journey towards personal fulfillment in my work — highly recommended.

June

Start With Why by Simon Sinek

I don’t know about you, but sometime around June, I start to lose the plot. My New Year’s resolutions tail off, my plans by now have either succeeded or failed, and I’m tempted to just coast through the summer.

Great leaders inspire others to take action, and it starts with understanding their own inner motivations. Why do we do what we do? As the weather warms and we head towards vacation-time, this is the perfect time to ask the hard questions, remind ourselves, and get back to our core motivations for marketing and selling in the first place.

July

Slipstream Time Hacking by Benjamin Hardy

Ah, that sweet, sweaty, sluggish summer. Trips to the beach, backyard barbecues, and… too many stifling afternoons where the office clock seems to be moving backward. What if there was a way to drastically speed things up? Not to race through time itself, but rather, to achieve your goals faster.

Introducing Slipstream Time Hacking. This basically-unedited self-published book with a ghastly cover is one of my favorite reads of all-time, and its topic is important: how to live more life in the small space of time we’ve been given.

Fun side fact: I interviewed Ben last year and he told me that Slipstream Time Hacking was his wife’s favorite book that he’s written!

“A person choosing to spend large portions of time in an unsatisfying job in order to make ends meet is on a fast track to his deathbed. Time will move increasingly faster as a result of his slow pace — the relativity of time.” — Benjamin Hardy

August

The Sleep Revolution by Arianna Huffington

Sleep is foundational to success. You will do your best marketing, your best writing, your best coding, your best work when you’re fully rested. International media magnate Arianna Huffington collapsed from overwork and exhaustion, but now considers it the best thing that ever happened to her. Why? Because she re-discovered the power of sleep and a holistic lifestyle to propel her work to new heights.

Side note: Though women do two-thirds of the book purchasing and out-read men nine-books-to-five on an annual basis, they’re still wildly underrepresented on the business bookshelf. I just checked Amazon’s Top 20 business titles and not one is written by a woman. This is clearly a hugely under-served market: please let us know your favorite female-written non-fiction books in the comments below.

September

A Pocket Mirror for Heroes by Baltasar Gracián

September feels like a second beginning, doesn’t it? Kids are back in school, the season starts to change, work returns to normal, and the marketing campaigns kick-off for the fall. It’s a great time to make new resolutions. How about this one? Be a hero.

September’s selection is easily the most underrated book on this list: the 17th century Jesuit philosopher known as Machiavelli’s superior shares a treasury of lessons on how to live a heroic life. He was a favorite of Nietzche, Schopenhauer, and Voltaire.

October

Rework by Jason Fried

As you enjoy the fall colors and the changing scenery, it’s a great time to release a new product or launch a new business in order to add value to our world. This book is so wonderfully simple — as is Fried’s company, Basecamp— that you can’t help but want to build a company (and life) in a minimalistic way. The key takeaway from this book is simplicity. Think of all the greatest marketing campaigns in history:

  • Just Do It

  • Think Small

  • Real Beauty

  • I Heart NYC

  • Where’s the Beef?

  • Wassup?

  • Got Milk?

Don’t over-think it.

November

How to Be Idle by Tom Hodgkinson

As you prepare for winter, it’s time to batten down the hatches and get into a routine that’s sustainable for the long, dark, cold months ahead. It’s also important, in the mad rush toward the end of Q4, to make sure you’re moving at a sustainable pace and not burning yourself out. As the Marines say: Slow is smooth, smooth is fast.

I used to oscillate between laziness and workaholism — while getting little accomplished — until I read Tom’s manifesto on slowing down in order to engineer a life you love. As you enter the holiday season, cozy up with a book that won’t make you feel guilty for doing so.

Here’s the secret: Your best marketing ideas and business plans don’t usually arrive in a manila folder that’s dropped on your desk. They come when you’re out living your life. Life builds business, not the other way around.

“In a world where you are constantly asked to be ‘committed,’ it is liberating to give yourself the license to be a dilettante. Commit to nothing. Try everything.”

— Tom Hodgkinson

December

The 22 Immutable Laws of Marketing by Al Ries and Jack Trout

As Christmas approaches, many of us re-watch holiday classics like White Christmas and It’s A Wonderful Life. This winter break is a perfect time to revisit what is perhaps the greatest marketing classic of all-time.

22 Laws has sold millions of copies, and while most marketers have read it at least once, how many laws can you name off the top of your head? How many less are you actively applying to your venture?

That’s why it’s the final recommendation for our year of marketing reading.

In Conclusion

The reality of late-stage capitalism is that almost everyone on the planet — be they a teacher, preacher, politician, startup founder, publicist, or social media manager — has become a marketer in some form or another.

Our responsibility is to offer the world excellent goods and services, to only promote things that lead to widespread flourishing, to help the planet, not hurt it. We want to save people time, to help them get healthy, to legitimately connect people to each other, to encourage the discouraged, to make the sad laugh, and to improve daily life for our global family and the planet we call home.

Once we know what we’re selling — and why we’re selling it — then it’s all about sharing our work as truthfully and creatively as possible.