Randy Nicolau built and sold companies before becoming an investor, founding Demdex, the first online data management platform, later launching and selling the office brand Poppin, and even serving as a former president of Playboy—a mix of backgrounds that's rare for someone in venture capital. He also has distinctive, hands-on habits, like preferring open floor plans to stay close to his team, screening senior hires by asking about the career moment they're most proud of, and tracing his entrepreneurial drive back to childhood, when he resold cheap sunglasses from Chinatown at school for a profit.