Randy grew up in the sailing community of Newport, Rhode Island working in the rigging and hull fabrication industry. He moved to San Diego in 2004 to crew tours of the America's Cup boat Stars & Stripes USA-11 raced by Dennis Conner in his 1992 America's Cup campaign. Randy went on to specialize in digital marketing and video production, using these passions to help people realize their dreams of getting out on the water.