In May 2023, when the sultry afternoon had settled down, Bijan Dam, a first-generation entrepreneur and a septuagenarian, was in a pensive mood. Introspecting life events, he ruminated that if he could rewind the tape of life, go back in space and time, would things be different. “I wish life gave me a second chance,” he lamented! Perhaps he could have planned better. Since founding the printing business in 1985, Ruby Art Press had scaled up significantly from letter press to full-fledged computer printing technology unit. The press had made inroads in job orders, government contracts and screen printing. Its client base was large. It also attracted repeat clients from adjoining states. With a successful business history of three and half decades, he had assumed the business would thrive perpetually. Today the business he had built, sustained and raised was practically gone. Why had he not anticipated the future potential of the business? Why had he not dwelled upon the successful business progression? Regardless of impeccable client service and personalized vendor management, what were the missing cues in the business? Deep agony and heavy burden of remorse were mentally excruciating. This had pestering effect on his health condition. Given these challenges, how could Dam ensure business continuity?