When Vasilios first arrived in the US, he was amazed by the general wealth in America. He also didn't speak any English and was a generally shy person. The first place he lived was Watertown, where his uncle was located. To initially support himself, he worked in restaurants as a waiter or busboy. There was a big Greek community in Watertown, including many of his relatives, so he had support in his acclimation to American life.

On a whim, Vasilios and a few of his relatives decided to move out to Chicago. He still spoke very little English, but he was able to get a job at a restaurant where they dressed up as Indians. This place has not stood the test of time, as you can probably imagine. In the 1950s, however, it provided a stable job for Vasilios as he explored a different region of America.

Vasilios returned to Massachusetts and opened up a restaurant called the Town Grill in Needham. Vasilios and two of his cousins owned and operated the restaurant. This was his first major business venture, and although the restaurant tragically burned down, Vasilios learned a lot about the business world and the food service industry. The fire forced Vasilios to go back to Watertown to return to his extended family.

When Vasilios returned to Watertown, he was much more Americanized, which he quickly used to his advantage. He began working in more high-class restaurants, such as Anthony's pier 4, a world-renowned restaurant in South Boston. He also logged some hours at the Half-Shell, a sports bar in Boston. These jobs, combined with his experience in America, made Vasilios an established community member. During this time period, he made enough money to begin investing for the future.