Capture the Flag is a genre of hacking competitions that turn vulnerability research into a real-time multiplayer game between teams of experts. Competing in a CTF is extremely challenging and demanding, and organizing one immediately presents a greater challenge: how do you run a competition for clever and creative computer hackers that love nothing more than breaking rules, voiding assumptions, and infiltrating infrastructure? It's complicated. This talk explores what it takes to build a team, design principles for a fun contest, the art of starting on time, and keeping momentum for successive contests. We'll also be looking at the differences between CTF organizing teams, CTF competing teams, and modern commercial devops teams, and some of the common ways all these teams mature, grow, and change over time.