Sam Pessin grew up all over the world with his family. His father was a foreign correspondent and because of this, Sam lived in Beijing, Jerusalem, London, and the U.S. Sam went to University of Michigan for undergrad, and then worked at Bain & Co for three years. Similar to his father, Sam sought out international experiences, and took the opportunity to transfer to Bain's Mumbai office for six months. About a year later, Sam started Remote Year with one of his best friends, and has been focused on that ever since.

He has been working remotely and has traveled to about 25 countries in the last few years.