Gordon identifies fear as the most significant practical obstacle between aspiring entrepreneurs and starting. And he makes a specific observation about the nature of that fear: it is almost always about assumptions, not facts. Most of the fears that prevent people from starting are structured like this: 'If I try this, then X bad thing will happen.' But the second half of the sentence, the X bad thing, is rarely examined. People treat the feared consequence as a given when it is actually a hypothesis. And most hypotheses about worst-case outcomes turn out to be wrong in important ways. Gordon distinguishes between two types of fear. Fear of failure: the belief that the business will not succeed. This fear is widespread and, on its own terms, statistically grounded: most new businesses do fail within their first few years. But the conclusion most people draw from this is wrong. Failure does not mean catastrophe. Most business failures produce learning, connections, and skills that make subsequent attempts significantly more likely to succeed. The cost of failure is lower than the fear of failure suggests. Fear of judgement: the belief that attempting and failing will cause others to think worse of you. Gordon argues this is the more paralysing fear and the less rational one. People who attempt things, even when they fail, are generally viewed more positively than people who never try. The judgement feared is usually a projection of the entrepreneur's own inner critic, not an accurate prediction of how others actually think. Gordon's practical prescription is to test the fear specifically: name the feared consequence precisely, estimate its actual probability, and estimate how you would actually respond if it occurred. The specificity almost always reduces the fear.