David Siegel is the CEO of Meetup, the largest platform for finding and building local community. He has over 20 years of experience as a technology and digital media executive leading organizations through innovative product development, rapid revenue growth, and digital traffic acceleration. Prior to joining Meetup, David was CEO of Investopedia and before that, President of Seeking Alpha. David’s book, Decide and Conquer: 44 Decisions that will Make or Break All Leaders lays out the framework for decision-making that leaders can use to ensure organizational and personal success. In our conversation we talk about David’s approach to failing, learning, and the art of the pivot, how to stand the inevitable tensions with doing things on the edge, and how to create a winning culture.