Super Upside Factor

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A01=Daniel Kang
A01=Daniel S. Kang
asymmetric outcomes
Author_Daniel Kang
Author_Daniel S. Kang
business consulting
career advice
Category=KJMB
Category=VSC
entrepreneurship
eq_bestseller
eq_business-finance-law
eq_isMigrated=1
eq_isMigrated=2
eq_nobargain
eq_non-fiction
eq_self-help
maximizing luck
non-linear
personal development
probability theory
professional development
self development
self help
startups
statistics
success
Venture capital

Product details

  • ISBN 9781394254910
  • Weight: 431g
  • Dimensions: 163 x 229mm
  • Publication Date: 24 Mar 2025
  • Publisher: John Wiley & Sons Inc
  • Publication City/Country: US
  • Product Form: Hardback
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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.

DANIEL SHIN UN KANG is a start-up founder who raised millions from investors including Y-Combinator. Previously, he was on the other side of the table as a venture capitalist at SoftBank Vision Fund, investing in tech companies and formally advising on boards. He studied finance at McGill University and policy at the University of Oxford.

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