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The Super Upside Factor. Asymmetric Principles that Will 10X Your Life. Edition No. 1

  • Book

  • 240 Pages
  • March 2025
  • John Wiley and Sons Ltd
  • ID: 6018409

A practical playbook to maximize luck in life and career

Venture capitalists manage to raise and invest trillions of dollars despite being wrong most of time through asymmetric bets - where a few big wins outsize losses by factors of 1,000x.

In The Super Upside Factor, Daniel Kang draws on his experience as a venture capitalist at Softbank Vision Fund and a Y Combinator-backed founder to adapt asymmetric principles for personal and professional life. He offers a clear framework for maximizing luck and generating outsized returns - what he calls Super Upsides. Through vivid, real-life experiments, Kang demonstrates how he put these principles into practice - from securing a book deal writing just 15 minutes a day; to recovering from a spiralling plane as a pilot; to raising millions by betting on pivotal career shift. 

This book draws upon the author’s firsthand experience going from no money, network, or looks to a highly successful career in entrepreneurship and venture capitalism. In this book, readers will find discussion on: 

  • Core concepts like the multiplier effect and black swans 
  • Probabilities, biases, and luck, and how to make them work for you, not against you 
  • Tools and first steps to create a “life portfolio” of uncapped upsides and unlimited opportunity 


Backed by decision science research and personal experimentations, the book strikes a balance between theory and practical advice, guiding readers to identify and optimize skewed life bets. Beyond the tactical elements, Kang explores the human side of applying these principles, including discussions on mental health, emotional struggles, and even tactically quitting.

The Super Upside Factor will inspire readers - even the most risk averse - to realize they are only a few Super Upsides away from extraordinary success and provide precise asymmetric principles needed to stack the odds in their favor.

Table of Contents

Part I Asymmetric Principles 1

Chapter 1 The Few Right Things 3

Chapter 2 Defining Asymmetric Principles 11

Chapter 3 Dogfooding in Public 27

Chapter 4 Staying Alive 49

Part II the Practical Guide 63

Chapter 5 Choosing the Right Games to Play 65

Chapter 6 Everything Is a Hypothesis 79

Chapter 7 Scaling with Momentum and Leverage 107

Chapter 8 Thinking in Portfolios 129

Part III When Rubber Meets the Road 153

Chapter 9 Avoiding the Single Point of Failure 155

Chapter 10 How to Quit 169

Chapter 11 The Super Upside Hypothesis 187

Notes 197

Acknowledgments 213

About the Author 217

Index 219

Authors

Daniel S. Kang