Zach Holman, one of the early engineers at GitHub, shares valuable lessons on scaling culture and the importance of shipping early. He emphasizes the significance of being proactive when scaling a company, constantly evaluating processes, seeking feedback, and making adjustments before problems escalate. The unique shipping culture at GitHub, which emphasized autonomy, ownership, and a friendly competitive spirit, allowed for rapid growth and development. However, as the company grew, maintaining this culture became more challenging, and implementing processes and adding managers was necessary. Zach stresses the importance of shipping early and often, embracing discomfort, and taking risks to seize opportunities. He also discusses common challenges in scaling culture, such as reacting to problems instead of being proactive, and advises startups on finding the right balance between short-term and long-term thinking. Overall, Zach's insights provide a wealth of knowledge and inspiration for building a strong shipping culture and avoiding the pitfalls of reactive decision-making.