When Cameron Yarbrough sits across from Silicon Valley's upper echelon, he isn't thinking about their celebrity status or millions in funding. 

Instead, the 50-year-old executive coach -- who's worked with the likes of Reddit co-founder and CEO Steve Huffman, Twitch co-founder Justin Kan, and Garry Tan, president and CEO of Y Combinator -- focuses on the insecurities and pain points that plague recent college dropouts and the entrepreneurial elite alike.