Blaine founded what's now known as Student Brands in 1999 as a freshman in college. He didn't raise any money and Barnes and Noble Education (NYSE:BNED) bought it for $58.5 million in August 2017. Blaine enjoys investing in for-profit and nonprofit organizations, especially when his experience is helpful to the founders. He's acquired about ten businesses as well. Blaine has also co-created a couple of television shows and has produced some films. He's particularly interested in investing in meaningful documentaries and scripted films.