What kind of books are most beneficial to an entrepreneur?

That was my question at the midway point this year, when my answer favored imagination and storytelling over operational practices.

That's still true. Now, however, with the perspective of a full year's worth of book under my belt, I can see the pattern of three specific categories of books that are most useful to entrepreneurs on our journey.

  1. First there are business-oriented books about the nuts and bolts of being an entrepreneur. These deliver the actual how-to, by explaining the mechanics of fundamental things like legal structure, marketing and sales. They may not be the sexiest thing you'll read this year, but they'll get the job done.
  2. The second category is about inspiration. I find that if I don't have at least one book from this category going, there's less juice flowing, creatively speaking. Books that inspire me also deliver a motivational shot in the arm, either by flip-flopping my perspective or by reminding me to get back to the "why" of doing what I do in the first place.
  3. The third category casts a vote for non-work pursuits. Naturally it's about trying to balance our work and home lives but it's also about using another part of our brains and, often, another part of our bodies as well. The point is to take us out of our heads and out of our seats in front of the computer.

Here were my top picks in each category this year, along with a few additional recommendations to boot.

Business and How-To

If you're in business, you're a salesperson. If you're an entrepreneur, you're most likely your startup's Salesperson Number One. No sales? No startup. No pressure. Right?

When we started Enolytics I had no idea how to be a salesperson and, like most salespeople I know, I had to get used to identifying as one. Which mostly meant overcoming the cartoon imagery of slick, fast-talking, say-anything-for-the-commission reputation that hounds the profession.

Certainly there are tactics to successful sales but here's what more important: the relationship matters more than the thing we sell. (I wrote an article on this topic, inspired by Selling Boldly, earlier this year.) I didn't know how to be a salesperson but I do know how to have relationships, and how to build and maintain them over time. That's the bridge I keep returning to, that helps me to cross into the "salesperson comfort zone."

Also highly recommended: Measure What Matters by John Doerr and The 5 Second Rule by Mel Robbins.


The truth is that I don't watch much television but even I have heard of Shonda Rhimes, the writer/creator behind Grey's Anatomy, Scandal and How to Get Away with Murder. I can relate to Rhimes as a writer, and I wanted to learn how she leveraged that skill in order to build the storytelling force and production company that is Shondaland.

I listened to Year of Yes as an audiobook which Rhimes herself narrated, and it made the world of difference to hear her in my ears: the benefit of her voice made me feel like I was in on her cheeky jokes and the hot-mess sass that's built her empire. It's Rhimes' candor that distinguishes this book as a must-read for entrepreneurs, particularly on tough, touchy topics like body image, prioritizing work over marriage, and the mechanics of how to tell a d*mn fine story that "lays track" for your own path forward.

Also highly recommended: Creative Visualization by Shakti Gawain and Tribes by Seth Godin.

Non-Work Pursuits

The irony of this book, and its title, is that as an entrepreneur I leave home all the time, often for extended periods to far-off places. Yet the travel part of my life reinforces the need for a comfortable place to land when I return.

In this book Gaines keeps the text tight and the images lush, showing by example and illustration projects that feel doable. Bonus? Rearranging furniture you already have amounts to a shift in perspective without an extravagant spend.

The shift in perspective is the common ground in each of these three categories of books, which is ultimately what's most beneficial to an entrepreneur.

Also highly recommended: Save the Cat! by Blake Snyder and Women's Power to Heal by Maya Tiwari.