Five Books Every Entrepreneur Should Read

Read ‘em and succeed (or listen, as you prefer). These are my top five go-to — and go back to — books for all things entrepreneurial.

The Hard Thing about Hard Things by Ben Horowitz

You know a book hits home when you buy it three times. Ebook, print, or audio, Ben Horowitz’ The Hard Thing about Hard Things is at the top of my list of entrepreneurial must-reads. 

This is the playbook for entrepreneurs, written by the larger than life persona behind Andreason Horowitz, one of the most notable VCs of our era. Ben Horowitz has 20+ years of experience in the startup field and he brings it all to the table: the challenges, the hard knocks, the victories, and the defeats. It’s a practical guide to all of the ins and outs of the startup world, but reads more like a memoir, as Horowitz takes the reader through his experiences and shares all his tips and tricks about hiring, firing, acquiring, etc.

The thing I love most about this book is how Horowitz’ personality comes through the pages — he’s an extremely charismatic guy with a penchant for loud rap music, and eminently relatable. 

TBH just waiting for this to come out as a graphic novel so I can add that to the collection. 

Favorite Takeaway: The importance of monthly 1:1s. 

The Culture Code by Daniel Coyle

The Culture Code is a great read for anyone who is part of a team or planning to scale a team — so, everyone (except for superheroes of course, who, as everyone knows, work alone). 

Coyle ventures into fields as diverse as education and food service to explore the nature of group culture: how to build it and how to maintain it. Through a seemingly exhaustive survey of highly performing teams, from the Navy Seals to Pixar, he distills their successes to three common principles — I could tell you what they are, but that would be spoiling it. 

If you love evidence-based studies and inductive reasoning, this is your book. 

Favorite Takeaway: Create a safe space for failure. Oh, and be vulnerable (too hard to choose just one from this book).

Measure What Matters by John Doerr

This great read adds another VC legend to my top five. John Doerr landed a job at Intel in the 1970s from a cold call, and from there he’s gone on to become one of the foremost investors in tech innovators and disruptors — so yeah, he knows what he’s talking about.

Doerr told an interviewer once that entrepreneurs should be missionaries, not mercenaries. In Measure What Matters, he’s spreading the gospel of those missionaries — the gospel of Andy Grove’s OKR framework (Objectives and Key Results). 

This was my first introduction to the concept of OKRs and now I’m a true disciple. As a system for measuring goals, Grove’s OKR framework — reimagined for the 21st century by Doerr — is an incredibly powerful tool for aligning a team and manifesting shared goals. 

Favorite Takeaway: The OKR framework itself, which I’ve implemented at Babyscripts.

The Creative Destruction of Medicine by Eric Topol, MD.

As the founder of a healthcare startup, Dr. Eric Topol’s book on disrupting medicine is a top five no-brainer. Topol was the first to put pen to paper to really dissect the importance of innovation in healthcare, and as a clinician at the top of his field his perspective is invaluable.

Topol takes a deep dive into the unique challenges of democratizing healthcare and innovating in the space. He outlines the barriers of a conservative medical community and challenges the consumer to advocate for change. 

His follow-up book Deep Medicine follows the progress of AI in disrupting healthcare, and it’s another must read for any tech entrepreneur trying to make inroads in the medical space. 

Favorite Takeaway: Fun fact, I actually used Topol’s algorithm for creative destruction in one of my very first presentations to investors. So I guess I owe him a little credit. 

The Phoenix Project by Gene Kim, Kevin Behr, and George Spafford 

This book holds the distinction of being the sole work of fiction in my top five, which makes it kind of a big deal. 

There’s a saying that fiction is often truer than reality, and this book follows through on that. The story follows an IT manager as he’s given the responsibility of transitioning his manufacturing company to an ecommerce model, and along the way it provides a lot of real-world insight into IT methodologies. 

Under the guise of an honestly pretty entertaining narrative (nerd alert), The Phoenix Project delivers extremely helpful examples for companies going through a digital transformation. As Bill (our hero) runs into issues, the authors (three whiz kids from the DevOps space) offer the reader a playbook for successful execution — things like process optimization, scaling engineering and operations, and dealing with software.

Favorite Takeaway: Best practice methodologies for IT. 

That wraps up the top five, but because I always have to up the ante (I’m an entrepreneur after all), here’s a couple bonus titles to close:

Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle

Talking to Strangers by Malcom Gladwell