Charles has been an active NY angel investor since the mid-2000s, has invested in more than a dozen companies, and has worked for and sat on the boards of ten more. He founded Extension Entertainment, a social music discovery platform. He is the owner of The Ineo Group LLC. Charles spent three years as the Vice President of Etsy Inc., was Vice President of Sales at Tacoda, and Executive Vice President of Corporate Development and Planning at RealMedia. Charles is located in New York City.