One thing that Adam Grant writes about in his book, "Originals", is how it's a bit of a fallacy that founders often dive head first and risk it all when starting their companies. Could be somewhat of a confirmation bias but he gives some great examples of how risk averse many founders actually are when starting their companies (Warby Parker was the main example if I remember correctly).
I came to say just this! He goes on to say that the great startup risk takers are confused with great "risk mitigators" who often hedge these risky bets. One example he gave was Woz who was working with HP when focusing with the creation of Apple.
http://www.adamgrant.net/originals