10 Books Every Founder Should Read

It seems like every blog has a top-10 list of books that founders absolutely, positively must read. So why should I be any different? 😂

All jokes aside, I’ve found that many book lists for founders over-index on biographies of “famous” founders and investors. While reading about Steve Job, Jeff Besos, Ben Horowitz or Elon Musk can provide plenty of motivation, your mileage as a reader definitely varies.

So I’ve put together a list of books that, I believe, are valuable for all founders to read, regardless of your personality, approach or experience. The book list below includes three categories:

• Understanding the Market and Opportunity

• How to “Startup”

• Founder Mental Health

Without further ado, here are 10 books (and one bonus book) that all founders should read:

Understanding the Market and Opportunity

1. Crossing the Chasm

Let’s start with one of the most foundational startup books ever: Crossing the Chasm. Originally published in 1991, Crossing the Chasm was one of the first mainstream business books to focus on the different stages of technology product adoption. The book is based on the technology adoption lifecycle, a model that describes the adoption or acceptance of a new product or innovation by different segments of the market. Its particular focus is on the “chasm” that exists between early adopters of a new innovation and the majority of the market. While the original edition of Crossing the Chasm is more than 30 years old, its framework is as relevant today as when it was first published.

2. The Innovators Dilemma

The Innovator’s Dilemma is another classic business book that every founder should read. First published in 1997, the book focuses on why incumbent companies consistently struggle to adapt to distributive technologies. Through a detailed study of multiple industries across several decades, Christensen unpacks the structural factors that prevent incumbents from reacting to disruption. For any founder who’s ever been asked “What if Google builds this?” (or who wants to better understand how their ‘David’ can conquer ‘Goliath’), this book is a must-read.

3. The Mom Test

When I teach entrepreneurship at the Beedie School of Business, The Mom Test is required reading for all students. This is by far the best book I’ve read when it comes to learning how to validate market opportunities when most people aren’t inclined to give you honest feedback. The book goes into detail about all of the ways people “lie” to you about your idea and strategies for getting effective market and product feedback.

How to “Startup”

4. The Lean Startup

Very few people can claim to have started a genuine movement, but Eric' Ries did just that with The Lean Startup. The basis of The Lean Startup is both simple and powerful: startups should iterate rapidly in order to make progress while course correcting early. Prior to the lean startup movement, software development typically followed a “waterfall model”, which involved significant design work up front and an implicit assumption that you could “think” your way through product design. In contrast, The Lean Startup emphasized repetitive cycles of learning, building and measuring results.

While most founders today implement some form of lean startup methodology in their companies, if you haven’t read the foundation within The Lean Startup, it’s worth the time.

5. The Cold Start Problem

Founders often hear about “network effects” when reseaching startups or talking to investors, but how do you actually create them? Andrew Chen is a General Partner at a16z and, prior to that, led rider growth at Uber. His book focuses on the “cold start problem” - aka how do you bootstrap the network effects necessary for two-sided marketplaces and other similar businesses to succeed. Through case studies including Uber, Tinder, Dropbox, Zoom and Airbnb, The Cold Start Problem presents a framework for testing and building network effects in a focused, iterative way.

While The Cold Startup is targeted at founders of two-sided marketplaces and other startups with network effects, the structured way in which Andrew presents his approach to go-to-market makes this a worthwhile read for every founder.

6. Venture Deals

Historically, the power and information dynamics between founders and investors has always been in favor of VCs. Brad Feld and Jason Mendelson, two of the co-founders of Foundry Group, sought to change that when they published Venture Deals in 2012 (sadly, the book came out 6 months after DataHero raised its Pre-Seed round from Foundry Group, so I didn’t have the benefit of this tome). The book’s subtitle, Be Smarter than your Lawyer and Venture Capitalist, is a tongue-in-cheek nod to both Brad and Jason’s roles as VCs and Jason’s status as a former lawyer.

Venture Deals provides an introduction to many of the key terms that appear in startup investment agreements and walks readers through the significance of each term, what the implications are and why investors ask for them. A particularly helpful aspect of the book is that it includes founder call outs throughout, in order to provide perspectives from actual founders.

7. Startup Communities / The Startup Community Way

2012 was a busy year for Brad Feld as an author, as he also published the book Startup Communities that year. The book talks about how to build entrepreneurial ecosystems, using the town of Boulder, CO as an example (Brad and his cofounders relocated to Boulder to form Foundry Group. He also co-founded Techstars there). 10 years later, Brad teamed up with Ian Hathaway to publish The Startup Community Way, a follow-up book that looked back on the lessons of Startup Communities while overlaying the experience of Boulder with those of emerging ecosystems around the world.

While Startup Communities and The Startup Community Way are both ostensibly targeted at stakeholders in emerging startup ecosystems, these books can be incredibly helpful for founders to better understand the resources available to them, particularly if they’re based in smaller or emerging tech hubs.

Founder Mental Health

8. Reboot

Jerry Colonna is a former VC-turned-executive coach, who for many years has run transformational founder and executive bootcamps. His 2019 book, Reboot, is equal parts a leadership book, a compilation of case studies and a shockingly vulnerable autobiography that looks back at Jerry’s own childhood and his struggles with mental health. While this is very much a book about leadership, the degree to which it focuses on the impact that our childhood experiences have on our ability to lead makes it stick out from the thousands of cookie-cutter management books that are published each year.

9. Lost and Founder

I’ve written previously about my friend Rand Fishkin’s book, Lost and Founder, in discussing founder mental health. Unlike most founder autobiographies, this one hits hard. Rand opens up about the rise and fall of both his company and his status within it, while unpacking countless aspects of the founder experience that are far more common than the “up-and-to-the-right” narrative that the media would have you believe. I highly recommend this book for any founder starting (or thinking about starting) an entrepreneurial journey.

10. Quit

Former professional poker player and current advisor-to-founders, Annie Duke, published an excellent study on the importance of quitting late last year, appropriately called Quit. I previously wrote a detailed review of this book (go read it now!). Suffice to say, I think that this is an incredibly important book and one that all founders should read.

Bonus: Coming Soon

11. Founder vs Investor

This September, renowned angel investor Jerry Neumann and former founder Elizabeth Zalman are publishing a new book called Founder vs. Investor: The Honest Truth About Venture Capital from Startup to IPO. The book covers a litany of topics related to the founder-investor relationship, which as any founder (or investor) can tell you is rife with conflicting motivations. I was lucky enough to read some early drafts and this looks to be an important addition to founder libraries.

The book will be released on Sept. 12, 2023 and can be pre-ordered on Amazon.