What are the biggest challenges to coaching entrepreneurs?

Two sides of the challenges. The entrepreneurs not knowing how to best work with a coach, know what they need help with, and understand how to apply what the coach is guiding them in.  It is also the case that many people are willing the help but have little to no training as a coach and often may not have experience as an entrepreneur.  The coaches and entrepreneur may confuse the difference between coaching versus mentoring and might seep into it being a training or teaching engagement.  Training is not the same as teaching, training being focused on skills and teaching on understanding foundational concepts.  Coaching is focused on performance while mentoring is guiding the direction.  These are simplistic description but it shows that understanding these distinctions require some study from both parties.  I address this in the chapter Coaching versus Mentoring in the book Startup SOAR Coaching.  In that chapter I explain how these notions overlap and how they are different.  I have found that in coaching executives to use coaching as a management style they can benefit from understanding the boundaries.  The entrepreneurs are much better at asking for the kind of help they can use and from the people who can take the role that they need.

Coaching entrepreneurs in the US versus Italy is a much longer topic than I can answer in a Q&A since it requires some background on the differences between the US and Italian economy and how people progress through the educational systems.  The simplistic statement is that in Italy the notion of an entrepreneur is very much connected to a family dynamic whereas in the US it is viewed as a heroic journey.  Both markets are advanced economies therefore for the majority of people, getting a job is the first choice, the easy road, but this is now changing with the shifts in the global economy.