Jay graduated from Randolph-Macon College on Sunday, May 30, 1993 in Richmond, Virginia. (Jenn continued and graduated in May 1996.) Jay and Jenn traveled to Freeport on Monday and on Tuesday, June 1, 1993, they began operation of one hot dog stand in Freeport beside the notable Polo/Ralph Lauren Building on Main Street. Together with Jenn, they began a transformation over the years from a hot dog stand with a few items to a food vending business with multiple Freeport locations selling regular and veggie hot dogs, sausage, grilled chicken bombs, lobster and crab rolls, burgers, homemade (by Jenn) cookies and rice krispie treats, and chips on the streets of Freeport. Their beverage menu has also grown from soda. In addition to lemonade, the stands now offer limeade, orangeade, strawberry lemonade and limeade, iced cappuccino, fresh brewed iced tea, strawberry iced tea, assorted fruit juices, sodas and Maine micro-brewed root beer.
In 2006 Jay and Jenn implemented a program to donate $.25 from the sales of spring water bottles to The Freeport Rotary Club for use in it's Water Filter Program in Santa Barbara, Honduras as well as other local charitable causes. To date over $7000 has been donated.