In 1994, Nitin Rai needed an eye checkup. To his surprise, his ophthalmologist used a Macintosh to check his history. “No one was talking about electronic medical records at the time,” Rai recalls. The then-29-year-old programmer—New Delhi native, schooled in Canada, veteran of the Bay Area tech scene and Oregon’s Mentor Graphics—launched a software start-up tailored for eye specialists. 

Two decades later, Rai still leads First Insight and its 100 employees. But after shepherding the firm through several tech bubbles, he also understands the entrepreneurial soul: why people start companies, and how they succeed or fail.

“Entrepreneurs get caught up in their own technology,” he says, offering one pitfall. “They get stuck in ‘creation’ mode forever.”

Today, Rai helps guide other new ventures as president of the Oregon chapter of the Indus Entrepreneurs (TIE). This global nonprofit started as a network of Indian and Pakistani tech pioneers who united to advise start-ups in the early ’90s. TIE now includes about 2,500 members. The Portland-based chapter (which will open a second incubator space in the Pearl this spring) has 40 “charter” members including established CEOs, investors, and attorneys, among them Greg Rau of Upstart Labs and Diane Fraiman of Voyager Capital.

“It’s really a give-back opportunity,” Rai says. “We have some experience to offer, and maybe some money.

As its acronym suggests, TIE laces together start-ups with money. TIE-connected investors joined other venture players to fund Chirpify, which lets people and companies buy and sell stuff via Facebook and Twitter, with $1.3 million last spring. In 2011, members steered $300,000 to Geoloqi, an app that meshes mobile users’ location with the other apps they’re using; the start-up sold to a much larger firm last year for an undisclosed amount.

In the case of a start-up called GlobeSherpa, Rai started with a reality check. “I was banging my head against the wall, trying to get funding,” recalls Nat Parker, who developed an app that lets mobile phone users buy transit tickets. “My partner and I were working 9 to 5, then being GlobeSherpa from 6 to midnight. The first thing Nitin told me is, ‘Look, you’ve got to quit your job, or no one will take you seriously.’” Parker followed the advice—and TIE members then led a $500,000 fundraising round to launch the company.

“Mentorship is great,” Rai says. “But in the end it’s advice plus money that makes a difference.”