The Startup Lottery

Your Guide To Navigating Risk And Reward

You’re excited to join a startup. You’re making one of the biggest decisions of your life–where to spend your career.

But what do you really know about the opportunity? Do you understand the risks and how to manage them?



The Startup Lottery Will Help You to:

  • Decide whether, when, and why working in a startup is right for you

  • Apply the Proof Continuum to understand startup stages and their relative risks

  • Use the Employee Due Diligence Checklist to evaluate the viability of startups

  • Negotiate for more salary and equity using the Job Offer Checklist

  • Know if your startup is in trouble and when it’s time to move on

About the Author

Gus Bessalel is a Harvard MBA, Inc. 500 CEO, and former management consultant who founded his first company at age 29.

Over a 30-year entrepreneurial career, he has managed, invested in, and advised over a dozen startups and helped his companies raise over $100 million in capital.

Praise for The Startup Lottery from Business Leaders


Kristen Fitzpatrick

Managing Director, Career and Professional Development Harvard Business School

The Startup Lottery is a quick and enjoyable read for entrepreneurs, potential investors, and joiners alike! It is especially useful for people thinking about joining a startup."


Ariel Eckstein

Vice President, Talent Solutions, LinkedIn

“ I have had the privilege of coaching and advising many young people contemplating start-up life. Going forward, for anyone considering such a move, my first piece of counsel will be ‘Read The Startup Lottery’.”


Stephen Kaufer

Co-Founder and former CEO, Tripadvisor

The Startup Lottery offers core lessons for surviving and thriving in startup life. The insights in this book will help you evaluate opportunities, embrace change, and manage risk. It’s not enough to work hard. You need a good navigation system to reach your destination."

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