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After earning an M.B.A. at Kent State University and working for International Business Machines Corp., Umang Gupta was tempted to return to his native India and start his own company. He went home for an extended visit in late 1977. Then he was lured back by two things, a girlfriend and a sense that Silicon Valley was his best career bet.

He married the young woman, Ruth Pike, in 1980 and raised a family with her. He signed on as employee No. 17 at what became the software giant Oracle Corp. He launched his own software company, Gupta Technologies Inc., in 1984. Initially successful, that business floundered in the mid-1990s as Oracle and Microsoft Corp. muscled into its niche.

“For the first time in my life I felt like a failure," Mr. Gupta wrote later.

He got another chance in January 1998 when he was named chief executive officer of Keynote Systems Inc. A pioneer in selling software as a subscription service, Keynote gave companies a way to measure the performance of their websites. Mr. Gupta expanded the company and sold it in 2013 to Thoma Bravo LLC for about $395 million.

In recent years, Mr. Gupta assembled a team to develop a free application called Reading Racer to help children learn to read.

Mr. Gupta died April 19. He was 72 and had been under treatment for cancer for 2½ years. He told friends that, faced with severe pain and bleak survival prospects, he was ending his life under a California law allowing doctors to prescribe an aid-in-dying drug.

Umang Pavel Gupta was born Aug. 23, 1949, in Patiala, in the northern Indian state of Punjab. His father was a civil servant in the labor ministry. His mother was a left-wing activist whose causes included organizing miners. His parents separated, and young Umang attended boarding schools before enrolling at the Indian Institute of Technology in Kanpur, where he earned a chemical engineering degree in 1971.

He chose Kent State in Ohio for his M.B.A. studies largely because he could support himself by working as a teaching assistant there. He then worked briefly at Copperweld Steel Co. before jumping to IBM. While working for IBM in Ohio, he spotted his future wife at a bar and asked her to dance. Raised near London, she was an immigrant too. They began dating, but Mr. Gupta felt the pull of his homeland.

“It was either Ruth or India," he wrote later in the New York Times. “I went back to India in order to make a decision." He returned to the U.S. in mid-1978 and tried to start a company. After failing to interest venture capitalists, he joined Larry Ellison’s Relational Software, later known as Oracle, where he helped write a business plan and became a vice president.

In 1984, Mr. Gupta left Oracle to found Gupta Technologies, later called Gupta Corp., which offered a new type of database software for personal-computer networks. The company went public in 1993 and soared to a market value of around $400 million, then plunged. Mr. Gupta told The Wall Street Journal he had a net worth of nearly $100 million for a few days.

Oracle considered acquiring Mr. Gupta’s company in 1994, but he couldn’t bear the idea of selling what he called his baby—a decision he later regretted. In 1996, he resigned as chief executive and left the company.

“My dad once told me, ‘No victory is final, and no defeat is fatal,’" he said. “I hadn’t paid attention."

Stung by what he saw as a failure, he traveled with his family across America—he was particularly entranced by a history museum in Deadwood, S.D.—and read a book a day for months. “I started to think of all the things I should have done to make the company outlast me," he said.

One of his conclusions was that he should have hired people willing to challenge his ideas. “Decisions can’t be based just on what the founder knows or his gut feels," he said.

He joined the board of Keynote Systems in 1997 and was named CEO a few months later. The company had a successful initial public offering in 1999 and then raised additional capital, helping it survive the dot.com bust.

While running that company, he encouraged board members to give him critical feedback, said Raymond L. Ocampo Jr., who was a Keynote director. “He didn’t want yes people," Mr. Ocampo said.

Mr. Gupta is survived by his wife, Ruth Gupta, along with two children, three grandchildren and two sisters. His philanthropy included donations to the Indian Institute of Technology and to a gallery on immigrants at the San Mateo County History Museum in Redwood City, Calif. The Guptas also funded Raji House in Burlingame, Calif., to provide services for children with developmental disabilities. It is named for their son Raji, who died at age 2.

Shortly before dying, Mr. Gupta set up a foundation to continue support of the Reading Racer app, which he developed with a team including Melanie Lam and Rodrigo Cano, both graduates of Carnegie Mellon University.

During his treatment for cancer, one of his small pleasures was rinsing his blue Mercedes CL600 at Ducky’s carwash in San Mateo, Calif. He assured friends that, given his thrifty nature and uncertain prognosis, he was being careful not to buy too many carwash coupons.

 

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