Startup Strategies and the Casino Floor

I’m embarking on teaching a new course this fall called “Ready, Set, Fail”.  It’s a course about entrepreneurial failure, but what it’s really about is how to learn from failure and how to use risk mitigation strategies to reduce the likelihood of startup failure.
While doing some research for the course, I came across Diana Kander’s book “All In Startup – Launching a New Idea When Everything Is on the Line“.  It’s a unique entrepreneurship book in that it’s written as a fictional narrative.  The setting is Las Vegas, the action is a poker tournament, and the main characters are entrepreneurs. Owen’s startup is failing, and successful serial entrepreneur Samantha helps him by educating him on a variety of entrepreneurship lessons straight out of Lean Startup methodologies. There’s even a little bit of sexual tension and an angry wife. There are many analogies along the way that relate gambling and entrepreneurial risk. Good stuff!
All of this got me thinking about how gambling and entrepreneurship can be kindred spirits at times. They both involve investment, time, and of course, heavy risk.
Too often as entrepreneurs we embark on an entrepreneurial journey without clear goals in mind. How much of our own (or other people’s) money are we willing to invest? How much time are we going to commit? What is our risk mitigation strategy? Are we going all-in or are we going to hedge against the all-too-many risks facing us? How do we know when to stop because we’re out of time and money or know when we’ve been successful enough to stop?
These are probably the same questions that a gambler should ask themselves before hitting the casino floor. Maybe by answering these questions we entrepreneurs (and gamblers) can develop a better startup strategy – one that is goal oriented, one that defines the parameters of the commitment, and one that has at least some semblance of strategizing around the high risk stakes.
Maybe none of this will eliminate failure but maybe we can make the startup game more fun and give ourselves more time to find a way to win. Are you all in?




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