One of our favorite parts of writing Unlikely Entrepreneurs was that it gave us a reason to catch up on our reading.
We read, and re-read, dozens of books over the course of our research.
The list below includes our favorite titles for entrepreneurs and would make great gifts for this holiday season—even a gift for yourself!
Some of the books are timeless startup classics. Others are not “entrepreneurship” books at all, but highlight the character and grit required to succeed in business.
We also include titles that focus on specific aspects of business, such as strategy, sales, and product. Some titles on this list will encourage you to think differently - a crucial skill for business owners.
Of course, we want to also share our upcoming book: Unlikely Entrepreneurs, coming out February 3.
If you pre-order the book, send us your receipt and shipping address via email, and we will send you a gift!
Now, onto the list:
1. Unlikely Entrepreneurs: Wins, Losses, and Crucial Lessons for Building Great Companies
by Lou Shipley and Patricia Favreau
This book challenges the myth of the “born entrepreneur” by spotlighting founders who succeeded through persistence, learning, and disciplined execution—not pedigree or luck. Blending real-world stories with research from MIT and Harvard, it’s both an inspiration and a practical guide for anyone who wants to build something on their own terms.
2. Aligning Strategy and Sales: The Choices, Systems, and Behaviors that Drive Effective Selling
by Frank V. Cespedes
A must-read for founders who realize too late that “great strategy” means nothing if it doesn’t translate into revenue. Cespedes shows how sales execution, incentives, and systems are inseparable from real strategy.
3. Competing Against Luck: The Story of Innovation and Customer Choice
by Clayton Christensen
This book teaches entrepreneurs how to understand why customers buy—not through demographics, but through the Jobs to Be Done framework. It’s essential for founders trying to build something people will actually pay for.
4. Disciplined Entrepreneurship: 24 Steps to a Successful Startup
by Bill Aulet
A practical, step-by-step guide for turning an idea into a real company without skipping the hard parts. Ideal for entrepreneurs who want structure, rigor, and fewer costly leaps of faith.
5. Dream Big and Win: Translating Passion into Purpose and Creating a Billion Dollar Business
by Liz Elting
A candid, operator-level look at building a billion-dollar business from first principles. Elting’s story is especially powerful for founders navigating sales, culture, and scale without a traditional Silicon Valley playbook.
Liz is also featured in Unlikely Entrepreneurs!
6. The Entrepreneur Mind: 100 Essential Beliefs, Characteristics, and Habits of Elite Entrepreneurs
by Kevin D. Johnson
A fast-moving collection of mental models and habits that shape how successful entrepreneurs think. Great for founders who want perspective and pattern recognition rather than tactics alone.
7. Entrepreneurship: Choice and Strategy
by Joshua Gans and Erin Scott
This book reframes entrepreneurship as a series of deliberate strategic choices, not heroic improvisation. It’s particularly useful for founders deciding what not to do as much as what to pursue.
8. The Experimentation Machine: Finding Product-Market Fit in the Age of AI
by Jeffrey J. Bussgang
A modern take on finding product-market fit through rapid testing, iteration, and learning—now amplified by AI. Perfect for founders who want to reduce risk before committing serious capital or headcount.
9. Going There
by Katie Couric
Not a startup manual, but a powerful reminder that reinvention often comes later in life—and after success. Entrepreneurs will relate to the personal courage required to start something new when the stakes are already high.
10. The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses
by Eric Ries
A classic for a reason: it taught a generation of founders how to test assumptions before scaling. Still essential reading for anyone tempted to build first and ask questions later.
11. The Media Training Bible: 101 Things You Absolutely, Positively Need to Know Before Your Next Interview
by Brad Phillips
Entrepreneurs are often their company’s chief spokesperson whether they want to be or not. This book teaches founders how to communicate clearly, avoid unforced errors, and build credibility under pressure.
12. MIT Sloan’s Ideas Made to Matter
A curated collection of research-backed insights on innovation, leadership, and growth. Ideal for entrepreneurs who want evidence-based thinking, not just anecdotes.
13. The Mom Test: How to Talk to Customers & Learn If Your Business Is a Good Idea When Everyone Is Lying To You
by Rob Fitzpatrick
A practical guide to customer conversations that actually reveal the truth. If a founder reads only one book on customer discovery, it should be this one.
14. Sailing True North: Ten Admirals and the Voyage of Character
by Admiral James Stavridis
A leadership book rooted in character, decision-making, and long-term judgment. Entrepreneurs facing uncertainty will appreciate its emphasis on values over tactics.
15. Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go From $0 to $100 million
by Mark Roberge
A blueprint for building a scalable, data-driven sales organization—starting with founder-led selling. Essential for entrepreneurs who want to grow revenue without chaos.
16. Think Again: The Power of Knowing What You Don’t Know
by Adam Grant
Entrepreneurship rewards those willing to update their beliefs quickly. This book helps founders recognize when persistence becomes stubbornness—and when rethinking is the real advantage.
17. Why Startups Fail: A New Roadmap for Entrepreneurial Success
by Tom Eisenmann
An honest examination of the most common failure modes founders don’t like to talk about. A valuable gift for entrepreneurs who want to avoid predictable mistakes rather than glamorize risk.
18. Zero to One: Notes on Startups, or How to Build the Future
by Peter Thiel
A contrarian take on building companies that create something truly new. Best for entrepreneurs thinking deeply about differentiation, monopolies, and long-term advantage.
by Sam Walker
Wondering what truly sets the best teams apart? It’s not talent, coaching or payroll. The answer is surprising, making this book a must read for founders and leaders.
That’s it for our list. What books would you add? Reply to let us know!
Happy Holidays and we will see you in the new year.
All the best,
Lou and Trish