In this episode of the Metrics that Measure Up podcast - Court Lorenzini, Founding CEO at DocuSign discusses his journey to co-Founding DocuSign and then his decision to leave after five years to found two more companies. During our conversation, Court shared his unique path to DocuSign, including his father's legacy as a founding father of Silicon Valley and his habit of recording his observations of how people managed difficult situations starting at the age of 13. Court  shares his belief that most CEO's are strongest or prefer one of the three stages that every start-up moves through including: 1) Napkin to Product-Market Fit; 2) Rapid Growth and; 3) Profitability.  Court loves, and used the term "Fills my Cup"  when discussing the joy he finds from starting companies and achieving Product-Market Fit. Court also shares his two key pieces of advice for aspiring entrepreneurs including: 1) Pressure test your idea rigorously to the point of trying to kill it early and often and; 2) Learn from predecessors who have attempted to blaze a similar path in your same market previously. Finally, Court shares his premise that founders created 70% of Terminal Value in the first five years of a companies life.  So, if your cup is filled by creating and establishing product-market fit, and you believe in statistical probability, it may serve founders better to repeat the company creation process multiple times to optimize the probability of great success.