Running a company is a deep adventure. In the contemporary entrepreneurial world great opportunity meets big expectations. At one moment funding can come through and a celebration is in order. In the next, the demands to grow and scale an organization creates demands on the leadership team to expand their skills at an equally rapid pace. Coaching is an opportunity to develop the skills in emotional presence, relational clarity, and communicative precision that are necessary to succeed at this level. To anchor this work at the deepest level it is vital to move freely between the personal and the professional, the past and the future. Authenticity and integrity are the foundation of true confidence.