Entrepreneur’s Reading List

I read a lot of books – particularly on the topics of business, entrepreneurship, economics, leadership, and psychology. This is a short list of those that I find myself most frequently recommending to entrepreneurs, with a few of my comments about each.  Enjoy!  

– Kris

The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It – Michael E. Gerber

A classic overview of the typical entrepreneurial journey and the pitfalls to avoid. This should be required reading before starting any business.

Traction: Get a Grip on Your Business – Gino Wickman

An engaging read that outlines a comprehensive system known as EOS – the Entrepreneur’s Operating System. This book identifies the six key areas of your business that must be improved, and lays out a process for everything from establishing clear goals to running effective meetings.

Simple Numbers, Straight Talk, Big Profits!: 4 Keys to Unlock Your Business Potential – Greg Crabtree

This is by far the best book on business finance I’ve ever read – has some good ideas and models for pay, hiring, profit sharing, etc.

Building A Story Brand: Clarify Your Message So Customers Will Listen – Donald Miller

This book will change the way you think about messaging what you do for your customer, and why they should care.  Do not write one line of copy, or create a single web page, until you have read this book!

Getting Naked: A Business Fable About Shedding the Three Fears That Sabotage Client Loyalty – Patrick Lencioni

This is an absolute must read for anyone in the consulting / professional services business.  It describes pretty accurately the culture I worked to create during the early years of The Kelso Group.

The Great Game of Business: The Only Sensible Way to Run a Company – Jack Stack

An Excellent book based on a real-world success story. Great lessons about open-book management and engaging employees in growing your company.

How the Mighty Fall: And Why Some Companies Never Give In – Jim Collins

This book is lesser known than many of Jim Collins’ others (Good to Great, etc.) but it is possibly his best work.

Give and Take: Why Helping Others Drives Our Success – Adam Grant

Really insightful book from Wharton professor Adam Grant about the psychology of reciprocity styles. After the first chapter, I began to see business relationships differently.

How to Become a Rainmaker – Jeffrey J. Fox

Every entrepreneur has to be a salesperson at some point. This book provides great, practical tips and approaches. Each chapter is only a few pages, so the book is easily digested at once or a little at a time.

The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses – Eric Ries

Taking from the groundbreaking teachings of Steve Blank at Stanford University, Eric Ries has created the manual for startups that is taught at entrepreneur centers and incubator / accelerator programs across the U.S. 

Predictably Irrational: The Hidden Forces That Shape Our Decisions– Dan Ariely

A Fascinating look at the psychology of decision making – particularly purchasing decisions.  Ariely basically invented the study of behavioral enonomics.

How Will You Measure Your Life? – Clayton M. Christensen

Clayton Christensen, one of the great researchers and authors of our time, takes many of his great business concepts (disruption, the “job to be done” theory), and applies them to other areas of our lives, to uncover the things that really matter. Highly recommended!

Strengths Finder 2.0 – Tom Rath

One of the most thoroughly and well-reasearched “personality profiles” in existence – great for team building and helping people to understand one another.

Home Run, A Pro’s Guide To Selling Your Business: 7 Principles To Make Your Company Irresistible – Jim Cumbee

Even if you’re not planning to sell your business any time soon, this book will give you plenty of insights on how to make your business really valuable. The same principles that make a business easy to sell also make a business a pleasure to own! This is an easy, enjoyable read, and it’s packed full of great stories and great lessons.

If You Plan to Raise Money…

If you plan to raise money from investors, there are two other books that should definitely be on your list:

Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist– Brad Feld and Jason Mendelson

An absolute must-read for anyone raising money from investors. It’s not only a strategy guide, but a handbook on all the terms you need to know.

Zero to One: Notes on Startups, or How to Build the Future – Peter Thiel

Great thoughts on the difference between growing an existing business and creating one from scratch. Very helpful for both entrepreneurs and investors.


Here are a handful of articles that I often reference in talks that I give and during coaching sessions:

The Psychological Price of Entrepreneurship – Jessica Bruder

DIY vs. Delgate – Fred Wilson

What Do Entrepreneurs Struggle With Most? – Kris Kelso


I also listen to a lot of podcasts – pretty much any time I’m alone in the car, this is what I’m doing.  Here’s a portion of my playlist:

The Startup Podcast
This is a great podcast where they reveal what it’s really like to start a business, and particularly what it’s like to raise money.  Think of it as therapy for startup founders :).  I’d recommend you go all the way back to the beginning and listen to the first season.  Warning – contains some profanity (it’s raw conversations).

Entrepreneurial Thought Leaders
A podcast of a lecture series from Stanford University.  Useful lessons in every episode.

Open for Business
Great basic lessons on starting and running a business.  A lot of it is fundamentals, not earth shattering, but some good stories.

Planet Money
If you are interested in economics in general, this is a very interesting and diverse podcast.

HBR Ideacast
Nuggets from Harvard Business Review.  Quality / engagement of the content is admittedly mixed, but there’s some really good stuff in there.