Losing Everything and Rebuilding as a Founder with John Rampton

From eight-figure exit to nearly $1 million in debt in less than a year! Serial entrepreneur John Rampton joins Stuart Draper on Startups with Stu to share his journey from childhood candy stand owner to multi-million dollar success. John reveals how writing for major publications like Forbes and Entrepreneur helped launch his businesses, and details the painful collapse of his company organize.com after Amazon shut them down and left him financially devastated. After hitting rock bottom—begging for gas money and facing eviction—John's fortunes turned when a random connection from his past led to work that sustained him while rebuilding. Through personal stories, including losing 65 pounds through a monk's unconventional four-year plan, John emphasizes the importance of taking care of yourself first before helping others in your "circles of influence." His current venture, Calendar.com, handles scheduling for major healthcare providers worldwide with just eight employees, demonstrating his ability to build efficient, profitable businesses.