Kolokotrones founded Castle Knoll Investments LLC, a financial services firm, in 2007. He co-founded Knight and Bishop, L.P., a venture capital firm, in 2013. He currently serves on the board of Perfect Price, an artificial intelligence price management platform, and Share Magnet, an e-Commerce marketing company that connects brands with their customers.

Kolokotrones graduated from Harvard College with a degree in economics in 2003. He then worked at the Union Station Foundation, a nonprofit organization dedicated to helping the homeless rebuild their lives, and studied computer science at the University of Southern California.