1. The Founders: The Story of PayPal and the Entrepreneurs Who Shaped Silicon Valley
If you want to understand Ken Howery, you have to start at the beginning. Jimmy Soni’s ‘The Founders’ is the definitive account of PayPal's chaotic and brilliant origins, and Howery is a central character. He was the company's first CFO, joining his Stanford
classmate Peter Thiel at what was then a fledgling startup called Confinity. The book details Howery's critical role in fundraising, navigating the merger with Elon Musk's X.com, and managing the financial strategy that led to PayPal's $1.5 billion sale to eBay. It isn't a book about Howery, but it's the closest thing to a biography that exists, painting a vivid picture of his early tenacity, diplomatic skills, and financial acumen in the trenches of a world-changing startup.
2. Zero to One: Notes on Startups, or How to Build the Future
This book isn't about Ken Howery, but it's the key to understanding the intellectual framework that has guided his career. Written by his long-time collaborator Peter Thiel (with Blake Masters), 'Zero to One' is the philosophical bible of the 'PayPal Mafia'. It argues for building completely new things (going from 0 to 1) rather than just iterating on what already exists. After PayPal, Howery co-founded the venture capital firm Founders Fund with Thiel and Luke Nosek, putting these exact principles into practice by making bold, contrarian bets on companies like Facebook and SpaceX. Reading 'Zero to One' is like getting a direct look at the investment thesis and worldview that Howery and his partners have used to shape the tech landscape for decades.
3. The PayPal Wars: Battles with eBay, the Media, and the Rest of Planet Earth
Written by another early PayPal employee, Eric M. Jackson, 'The PayPal Wars' offers a grittier, more insider perspective on the company's tumultuous early days. While 'The Founders' is a comprehensive historical account, this book reads more like a battle journal. It captures the intense pressure, competitive threats, and internal power struggles that defined the company culture. Howery was at the center of this, not just as CFO but as a key part of the core team that held the company together. For anyone curious about the environment that forged the tight-knit, resilient group of entrepreneurs known as the 'PayPal Mafia,' this book provides essential, ground-level context that helps explain their subsequent success and loyalty to one another.
4. The Contrarian's Guide to Leadership
This is the only book on the list that directly features Howery's own writing, though it is not a book by him. The main author, former USC President Steven B. Sample, lays out his principles for unconventional leadership. The updated edition includes a new chapter penned by Howery himself, where he applies Sample's contrarian principles to the world of venture capital and startups. It offers a rare, first-person glimpse into his thought process and how he identifies and nurtures groundbreaking companies. It bridges the gap between the theoretical ideas in a book like 'Zero to One' and the practical application required to succeed as an investor and mentor to the next generation of founders.
