Umang Gupta, a Silicon Valley executive who helped drive two trends in business software while blazing a trail for Indian-born entrepreneurs, died on Tuesday at his home in San Mateo, Calif. He was 73.
More than two years after learning he had terminal cancer, Mr. Gupta opted to take his own life using prescribed medication as allowed under California law, as he wrote in a farewell letter to friends and family that was shared with The New York Times.
Mr. Gupta arrived in Silicon Valley in 1978, a time when computing chores were typically carried out on large machines running programs supplied by the manufacturers. He was part of a new breed of entrepreneurs, like Microsoft’s Bill Gates and Oracle’s Larry Ellison, who helped build an independent software industry.
That industry expanded with the emergence of personal computers in the late 1970s and early ’80s. PCs gradually took over many business tasks, exchanging files over networks with larger machines in an industry trend called client-server computing.
Mr. Gupta had a ringside seat as one of Oracle’s early employees, taking credit for writing the company’s first formal business plan in 1981. In 1984, he left to start a competing company, Gupta Technologies, which offered one of the first databases for PCs and programming tools that allowed companies to write applications to run their businesses in a client-server style.
“Umang was a real pioneer in the client-server world,” said Mitchell Kertzman, a former rival who is a managing director at Hummer Winblad Venture Partners, a venture capital firm.
In 1993, Mr. Gupta took his company public, a breakthrough for a software concern led by an Indian executive. Many of his compatriots would play major roles in starting and leading tech companies.
But Gupta Technologies ran into increasingly stiff competition from Oracle, Microsoft and Mr. Kertzman’s Powersoft, and the company ultimately faltered. Mr. Gupta left the company in 1996. It later changed its name and passed through several owners before fading from prominence.
In a recent interview, he called his departure “just the hardest thing I ever did.”
But Mr. Gupta reinvented himself just in time to catch the next major wave in technology: the rise of the internet. In 1997, he invested in and later became chief executive of Keynote Systems, which developed software that companies used to monitor the efficiency of their websites.
Unlike most other companies of the era, he chose to run the software online and sell it as a subscription service, a business model that now dominates enterprise computing.
“He was ahead of his time in thinking about where things are going and what’s going to happen next,” said Mohan Gyani, a longtime Keynote board member and friend.
Mr. Gupta took Keynote public in September 1999. In early 2000, he raised $350 million more in a secondary offering, which helped Keynote ride out the tech bust that soon followed.
In 2013, he sold Keynote for $395 million to the private equity firm Thoma Bravo and retired from business software. But he kept a high profile as a philanthropist and by working with a group that represented alumni of the Indian Institutes of Technology (he had attended the campus in Kanpur), said Kanwal Rekhi, a veteran Silicon Valley tech executive and investor who served on the board of Gupta Technologies.
Members of the I.I.T. group included figures from industry, academia and the investment community who could often strongly disagree with one another on a range of topics, said Gunjan Bagla, the chief executive of the consultancy Amritt, who helped lead the group with Mr. Gupta.
“Umang was an exceptional leader who could bring a group from chaos to calmness,” he said.
Umang Gupta was born on Aug. 3, 1949, in Patiala, in the northern Indian state of Punjab, to Ved Prakash Gupta, who worked at India’s labor ministry, and Ramnika Gupta, a politician. Umang’s parents were socialists from different castes who met at the funeral of Mohandas Gandhi, a departure from a traditional arranged marriage.
The couple later separated, and Umang was raised with the help of grandparents.
He spent four years at a military boarding school and was expected to join the National Defense Academy, a tradition in his mother’s family. Instead, he chose I.I.T. Kanpur, where he earned a bachelor’s degree in chemical engineering in 1971. The campus had some of the first IBM computers in India, and Mr. Gupta gained programming skills there as well.
He then went to the United States to earn an M.B.A. at Kent State University — the only place, he said, to offer him a position as a teaching assistant. After earning that degree in 1972, he worked for a steel company and then as a salesman for IBM.
Mr. Gupta considered returning to India. But in 1975 he met Ruth Pike, a Briton who became his wife. He decided to move to Silicon Valley, where he briefly worked for an IBM competitor called Magnuson Computer Systems and unsuccessfully tried to raise money for his own company. He joined Oracle in 1981.
His wife survives him, as do a daughter, Anjali Clare Gupta; and a son, Kashi Christian Gupta. Another son, Raji Gupta, died at an early age. In his honor, Umang and Ruth Gupta helped found Raji House, a weekend respite home for developmentally disabled children that is associated with the organization Partners & Advocates for Remarkable Children & Adults.
Over the years, Mr. Gupta encouraged his colleagues to challenge his thinking, said Raymond Ocampo, another former Keynote board member. And he blended leadership traditions of India and the U.S.
“The way he led people was based on fundamental Indian family business values, which are rooted around loyalty,” said Vik Chaudhary, a director of product management at Meta who competed against Gupta Technologies at Oracle before joining that company and later Keynote. “But the way he conducted business was about fierceness and competition.”
Even after he was mostly retired in 2013, Mr. Gupta helped develop a free smartphone app called Reading Racer, which uses speech recognition technology to help children improve their ability to read out loud.
In his farewell letter to friends and relatives, Mr. Gupta said medication had allowed him to live fairly comfortably for more than two years after his cancer diagnosis. But the pain ultimately became severe.
“Why should I not go out with dignity,” he wrote, “when I can still stand on my own two feet, although barely?”