As a first-time founder or CEO, you’re bound to make mistakes. A lot of them (at least, I did). It’s crucial to learn fast, minimize mistakes and look around corners.
Great books, podcasts and youtube channels can help you do exactly that. In this post, I’ll share some of the resources I used as CEO of DataCamp to learn faster and avoid making some of the most basic mistakes. Almost all of them are beginner friendly, while most are still useful for more experienced folks.
In the past 2 years, I learned the most by reading books (or typically, by listening to them through audible). Here’s my full reading list from 2018-2019.
#1 book that helped me think about how to be a better CEO and founder
The Hard Thing About Hard Things
by Ben Horowitz
In contrast to many business books, this book is brutally honest about the hardest challenges you face when running a company. Ben Horowitz speaks both from his own experience as a CEO as well as from his extensive experience as a partner at Andreessen Horowitz (a16z), one of the most respected venture capital firms in Silicon Valley. I will continue to reread this book regularly.
You should also check out his talk on a key management concept that a lot of folks get wrong.
A close second in this area is Peter Thiel's book Zero to One. As a co-founder of Paypal, first investor in Facebook, etc. Thiel barely needs an introduction. In Zero to One, he shares his unique and sometimes contrarian perspective on innovation and how to build lasting companies. The book is based on the lectures he gave at Stanford University in 2012.
#1 book that helped me think about company culture better
Principles: Life and Work by Ray Dalio
This book synthesizes the learnings of Ray Dalio, the legendary founder and CEO of Bridgewater Associates, one of the most successful hedge funds in the world.
Especially part 3 of this book is relevant for entrepreneurs. Ray thinks about organizations as made up of culture and people. He describes the culture that he created at Bridgewater. While Bridgewater's culture is unique, it's exceptionally useful to understand how Ray thinks about culture and its components. It will help you to define your company culture as well as help you understand the importance of clearly defining company culture early on in a company's life span.
#1 book that helped me think about company goals and efficiency
Measure What Matters
by John Doerr
This book explains the goal-setting system of Objectives and Key Results (OKRs). OKRs have helped many prominent tech companies achieve explosive growth. Poorly done OKRs are a waste of time, an empty management gesture. Well done OKRs are a motivational management tool that helps make it clear to teams what’s important, what to optimize, and what tradeoffs to make during their day-to-day work. Writing good OKRs isn’t easy, but it’s not impossible, either. This book will help you get it right.
#1 book that helped me raise VC capital
Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson
This book is extremely useful for entrepreneurs looking to raise capital from angel investors or venture capital firms. It helps you understand the key elements of a fund raising negotiation from both a legal as well as business point of view.
#1 book that helped me become a better negotiator
Never Split the Difference: Negotiating as if Your Life Depended on It by Chris Voss and Tahl Raz
Hands down the best book on negotiation I've read. Chris Voss was the FBI’s lead international kidnapping negotiator. In this book, he shares fascinating stories to illustrate nine principles you can use to become a better negotiator in business and life in general.
In addition to the books mentioned above, I highly recommend the following resources to first-time founders/CEOs:
This week in startups I grew up in Belgium, not exactly surrounded by (technology) entrepreneurship. I started learning about tech entrepreneurship by watching this show from Jason Calacanis. He now has interviewed close to 1,000 tech entrepreneurs and investors. Some of the best episodes include: Chris Sacca, Anne Wojcicki, Travis Kalanick, David H. Hansson, Chamath Palihapitiya, ...
Saastr Saastr has an incredible collection of interviews and talks of top entrepreneurs and founders. You'll find that they are focused on scaling SAAS (Software As A Service) companies and their content is especially useful for later stage companies. Their goal is to help everyone get from $0 to $100m ARR (Annualized Recurring Revenue) with less stress and more success.