Apptio co-founder and CEO Sunny Gupta has recently sold his software-as-a-service (SaaS) company to IBM for a reported sum of USD 4.6 billion. Following the acquisition, Sunny Gupta will be returning to IBM, where he initially began his career back in 1992.

Sunny Gupta, a 53-year-old entrepreneur based in Silicon Valley, has a track record of launching four successful startups. Originally from Chandigarh, India, Sunny Gupta’s father served as an IAS officer. With an early passion for entrepreneurship, Sunny Gupta and his two brothers ventured into running their own prosperous companies at a young age.

In 1989, Sunny Gupta arrived in the United States with a mere USD 2,000 to pursue his studies at the University of South Carolina. He shared in an interview with the New York Times that he felt compelled to come to the US due to the prevailing belief that “you can start from nothing and create something.” While he managed to secure a partial scholarship, Sunny Gupta also undertook odd jobs, such as dishwashing and working as a mover, to support himself until he obtained a full scholarship.

In 1992, Sunny Gupta joined IBM as a software developer. However, after a few years, he decided to venture into entrepreneurship, fueled by his belief that he could excel at higher positions within the company. “I really felt that I could do my boss’s boss’s job. Yes, you don’t know what you don’t know, but I just had this strong conviction within me,” he explained.

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In 1996, Sunny Gupta launched his first startup, Vigor Technology, which he later sold to Rational Software for a sum estimated between $3-4 million. His second startup, Performant, was subsequently acquired by the software company Mercury. In 2005, Sunny Gupta embarked on his third venture, iConclude, and successfully sold it to Opsware in 2007.

After the sale of iConclude, Sunny Gupta co-founded Apptio alongside Kurt Shintaffer. Apptio, a company with over 1,400 employees worldwide, including in India, specializes in providing software-as-a-service solutions.

The recent acquisition of Apptio by IBM marks a significant milestone in Sunny Gupta’s entrepreneurial journey, bringing him full circle back to the company where he initially launched his illustrious career.