Many have watched the HBO comedy series “Silicon Valley,” but in Nitin Rai’s own words, he lived that life. After college, he moved to the tech capital of the world, sleeping on couches with $50 in his pocket. Years later, Rai remains the CEO of First Insight, the company he started in 1994, as well as a major figure in Oregon’s investment landscape; as the President of TiE Oregon and a Founding Partner of Elevate Capital, Rai is one of the first people Oregon startups look to for getting their big ideas off the ground. In this episode, Rai recalls his rags-to-riches story, how his opinion of angel investing changed over time, and how being a person of color affected his ability to rise through the ranks of corporate America.