In 1980, Jay started kindergarten as a charter student in the first class at Chesapeake Academy, which is now Severn’s Lower School, but at the time was temporarily located in an old converted beauty salon on Richie Highway. At an early age, Jay began showing signs of an entrepreneurial spirit, from the proverbial lemonade stand, to reselling golf balls he had found in the woods, to recycling aluminum cans for profit, and even creating a festival for neighborhood kids.
Starting in middle school, Jay enrolled at Severn where he was a dedicated scholar and athlete. In high school, he competed on both the soccer and tennis teams, but his true love was baseball where he played in city leagues because, in spite of his active advocacy for it, Severn did not yet field a baseball team. His true talent, however, was in wrestling where he was a four year starter, captain of the team his junior and senior years, and a key member of Severn’s first wrestling conference championship, the banner of which still hangs in the school’s gymnasium today. Jay was also a leader in several organizations including the National Honor Society, math team, ping-pong club, and the school newspaper.
After graduating from Severn in 1992, Jay attended the University of North Carolina at Chapel Hill. Hailing from a family of doctors, Jay initially thought he would follow in his father’s footsteps by taking a pre-medical curriculum which led to dual degrees in chemistry and philosophy. Jay also worked as an emergency medical technician and with the American Red Cross while in college to gain experience in the healthcare field. But by this time, after perfecting the art of selling Tarheel basketball tickets on the early internet, the seeds of entrepreneurship had taken ahold of him, and he decided to bypass medical school and instead further his business education. To that end, Jay earned a Master in Accounting from UNC Chapel Hill, followed by a C.P.A. and his first real job as a tax consultant with Arthur Anderson in Atlanta, Georgia in 1998.
In Atlanta, Jay’s career steadily advanced up the corporate ladder. But the politics and lack of freedom in corporate America was slowly wearing away at his spirit. When the Enron scandal took down Arthur Anderson, Jay had had enough and headed to Austin in 2002 to pursue an MBA in finance and entrepreneurship at the University of Texas, with the goal of starting a business.
As luck would have it, on the first day of class, Jay sat next to two strangers who would soon become the future co-founders of his first and most successful tech startup, uShip. After graduating from business school in 2004, Jay spent the next ten years with them building uShip into the world’s largest peer-to-peer global shipping marketplace. Regularly winning the best place to work in Austin, uShip’s unusually sized shipments were so interesting that they made a major reality TV show about it, dubbed “Shipping Wars”, which aired for over 7 seasons and 100 episodes on A&E and is still seen in syndication around the world. In 2012, Jay co-founded the non-profit Startup Games, an intense but tongue-in-cheek one-day “Olympic” style competition between dozens of startups where the “sports” are typical startup pastimes such as ping-pong, darts, and Connect Four. The annual event has raised over half a million dollars for local charities, and is now replicated in four cities nationally. In 2013, the Austin Business Journal awarded Jay the honor of being named “Austin’s best CFO”. In 2014, after growing uShip to over 300 employees and millions of shipments, Jay decided to leave and start all over again. That year was a busy one, as he co-founded three more companies that are still active today: Everfest, the world’s largest festival discovery site; Roverpass, the leading RV campground booking site; and the Vulcan Gas Company, Austin’s first award-winning electronic focused live music venue.
Last year, Jay decided to get back to his transportation roots and co-founded Hitch, an app that aims to take excess cars off the road by letting customers book shared car rides between major cities, such as Austin and Houston, as easily as an Uber. Over his career, Jay has helped raise over $50 million dollars for companies he has co-founded, while personally investing in or actively advising dozens of other young entrepreneurs around the country.