Beyond mastering the helping relationship, proficient coaches also need to manage the commercial and financial aspects of the coaching relationship. In this chapter, through two cases, we explore the issue of money in coaching. First, we examine the challenges faced by coaches when they are getting established as independent coaches. Second, we look at the consequences that coaches must deal with when the financial aspects of the contract have been neglected. We show that money matters in coaching can be closely linked to and impacted by the financial value of coaching, as perceived by the different stakeholders, and by the reputational concerns that the coach may have.