SMU graduate Adrian Cheng cold-called more than 10 Silicon Valley start-ups last year, asking to intern with them during his summer break between May and August.
When he finally found one which matched his aspirations, he bought a $2,000 plane ticket and flew to the San Francisco Bay area on his own.
"As a person, it is important to stretch yourself," said the 25-year-old, who graduated from the School of Information Systems with a high grade point average of 3.74.
"I didn't think much about failure, because I would get to learn from the best there."
He spent just over two months with application developer Tiny Post, which had a staff strength of four full-timers.
During that time, he went on to develop an application that became South Korea's top-ranking featured app in the Apple App Store.
Named Tiny Post, it enables people to take pictures, write captions over them, and share them on Facebook, Twitter and Tumblr.
"In Korea, pop culture is strong, and girls like to beautify their photos," he said.
The son of an entrepreneur and a housewife will be flying off to the United States on Sunday to begin his full-time job as an engineer with Trip Advisor. The travel website acquired Tiny Post and its staff last year. The self-professed "heartland boy", who lives in a five-room HDB flat in Toa Payoh, said his priority is to see the world.
"Young people in Singapore grow up in a system where everything is laid out nicely," he said. "But this prevents us from noticing tons of opportunities out there in the world."