SimonDelivers had launched as a online grocery delivery business in 1999 at the height of the Dot.com boom. By 2001 many of their competitors had imploded in the Dot.com bust. Miraculously SimonDelivers had managed to be one of the few that weathered the storm only to be later caught up in the real estate bust of 2008. Often times we can learn more from failures of others than from their successes. This story is a glimpse into the lessons learned from the failure of SimonDelivers.