Blaine is the founder of Immeasurable, an investment team based in Los Angeles. Blaine uses his twenty years of experience as an entrepreneur to support fellow entrepreneurs in their journeys.

Prior to focusing on Immeasurable full-time, Blaine was the CEO and chairman of Student Brands, an edtech holding company that he co-founded as a college freshman in 1999. He and his co-founders bootstrapped Student Brands for eighteen years and it was acquired for $58.5 million by Barnes and Noble Education (NYSE: BNED) in August 2017. Blaine was also the CEO and co-founder of Solve, a service that helped people quickly get through immigration and customs when traveling overseas. Solve was in Y Combinator's summer 2017 batch and it was acquired by Blacklane later that year.

Outside of work, Blaine helps North Korean defectors build new lives alongside Liberty in North Korea. He also helps founders and venture capitalists build meaningful and accountable commitments to philanthropy.