While the benefits of AI can reduce costs, improve efficiency, and enhance accuracy, many AI tools lack transparency and have inherent biases. Business leaders today must evaluate these opportunities and risks and perhaps rely on experts around them to provide most of the perspective on the situation. In an attempt to bridge the worlds that collide around digital transformation, we asked experts in several fields to share their thoughts on AI, ethics, and the implications for business decision-makers. Summit 2019 explored this topic from the perspectives of a philosopher, an attorney, and an entrepreneur, taking attendees on a journey from outside consultant, to inside general counsel, and into the CEO's office.