Holiday book list: 20 essential resources for entrepreneurs

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In early November, an entrepreneur asked me which books and resources that I thought would help him become a successful CEO for a large e-commerce company.

While I agree that nothing teaches like experience, failures, scars and reflection, I also truly believe that we can learn from others’ experiences and scars by reading their talks, articles and books. Below are 20 books that I think are some of the most powerful for learning how to become a business leader, at any startup. 

(Hint: they're also great gifts for entrepreneurs, and if you buy these books through, Amazon will donate to a charity of your choice when you buy qualifying items).


Developing good leadership really only happens with practice, and not by reading books, but the following books will help you reflect about the topic more deeply. (A lot of classic literature books are also great, but I will keep my recommendations to non-fiction).

1. The Essential DruckerThis is a collection of articles by Peter Drucker, the famous management consultant, on management and leadership.

2. The Art of Possibility: A gripping book about managing to everyone’s ultimate potential.

3. Mandela’s Way: Lessons on Life, Love, and Courage: fifteen crucial life lessons distilled from interviews with Nelson Mandela.

4. Leadership Without Easy Answers: Somewhat academic, but still a great read about the core of leadership.

5. Delivering Happiness: Tony Hsieh, the Founder of Zappos, is known for creating great work cultures that lead to unparalleled service.

Scaling and Iterating

It's also critical for founders to develop a good understanding of how organizations, companies and startups develop.

6. Founders at Work: A series of fascinating stories and lessons from founders of high tech startups ranging from Flickr and Craigslist, to Yahoo!, PayPal and Apple
7. The Startup Owners‘ Manual by Steve Blank offers a scientific approach to developing a business model; entrepreneurs can also take his free class on Udacity

8. Crossing the Chasm: The ultimate reference for taking a product from niche to mass market.

9. The Fifth Discipline: This book is somewhat academic as well, but it teaches you how to think about organizations as systems

10. The Innovator’s Dilemma and The Innovator’s Solution: Clayton Christensen is the definitive reference on the theory of disruption and his books help entrepreneurs understand how to take advantage of a current industry’s inability to react.

Product Design

A well-designed product is key for building great companies, and a well-designed user experience is the best way to reach customers. These books go into detail about the process of design and optimization for the user.

11. Sketching User Experiences: This book focuses on the overall design process.

12. Landing Page optimization: A how-to guide for maximizing exposure and conversion rate.

13. Conversion optimization: Both of these books go into the process of understanding how users interact with websites and how to make it easier for them to achieve what they want.

Follow the Greats

Finally, a great way to learn is to follow very smart people that understand what it takes to start and scale a tech company:

14. Bill Gurley:

15. Chris Dixon:

16. Paul Graham:

17. Fred Wilson:

18. David S. Rose: and Follow him on Quora

19. Steve Blank’s Tools for Entrepreneurs

20. Tom Eisenman’s compilation about the best posts on managing startups 

One last caveat, while reading is a great way to learn, make sure you are differentiating between the resources that are teaching you something fundamental, that perhaps comes with recommendations, and the noise, which is a core skill for a busy founder.

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