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10 Startup Founder Books Worth Re-Reading Every Year

All Founders

Books worth revisiting annually as you grow your startup. The emotional reality of building companies, decision-making under uncertainty, and operational fundamentals that hit differently at each stage. You absorb different lessons when you're managing 20 people versus raising your Series A. Pick 2-3 per quarter—don't try to read all 10 in January.

10 books in this collection
1

Building a business when there are no easy answers. Horowitz shares the brutal, honest reality of running a startup—the struggles, the tough calls, and how to survive them.

2

A practical guide to talking to customers without getting lied to. Fitzpatrick shows how to ask questions that reveal honest feedback instead of polite encouragement, helping you validate ideas before building.

3

Former Intel CEO Andy Grove shares practical wisdom on running teams and organizations. This management classic covers leverage, meetings, performance reviews, and output-focused leadership.

4

Thiel argues that the most valuable companies create something entirely new rather than competing in existing markets. This contrarian guide challenges conventional thinking about competition, monopoly, and innovation.

5

The difference and why it matters. Rumelt cuts through the fluff to show what real strategy looks like: a clear diagnosis, guiding policy, and coherent actions.

6

The A method for hiring. Smart and Street present a systematic approach to hiring that helps you avoid costly mistakes and find the right people for your team.

7

Timeless lessons on wealth, greed, and happiness. Housel explores the strange ways people think about money and how behavior matters more than knowledge.

8

A practical guide to decision-making under uncertainty from poker champion Annie Duke. Learn to embrace probabilistic thinking and make better choices when you don't have all the facts.

9

Collection of interviews with founders of famous technology companies about their earliest days. Jessica Livingston reveals what really happened at Apple, PayPal, Flickr, and more.

10

The definitive guide to building startups using validated learning, rapid experimentation, and iterative product releases. Ries introduces the Build-Measure-Learn feedback loop that has become the foundation of modern startup methodology.

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