He attended Connecticut College, and competed on their varsity sailing team. In 2007, he took time off of school to compete full time for the 2008 Olympics. His coach, who had coached him for nearly a year, began competing against him 3 months prior to the trials. Bob placed 3rd at the 2008 trials (only one goes).
Upon graduating in December of 2009, Bob decided to devote the next two years towards qualifying for the Olympic Games. 2010, was a difficult year for him. He didn't have great results and significantly trailed 2008 Olympian Ben Barger in the rankings. However, in 2011 Bob had a breakout performance at the 2011 Rolex Miami OCR in January. He was the top American qualifying himself for the 2011 Pan American Games in addition to the top spot on the US Sailing Team. He linked up with some great training partners, spent in 2 months in New Zealand and continued to carry the momentum forward. He had a solid performance at the 2011 Sail For Gold Regatta in Weymouth UK and secured a 14 point lead in the Olympic selection process. Finishing off the year, Bob performed at his best and placed 38th out of 90 at the 2011 World Championships in Perth and secured his spot on the US Olympic by more than 50 points - a significant margin.
Bob defeated 2008 Olympian, Ben Barger, who had 8+ years of experience on him. Bob will be the only US Olympic Windsurfing representative in history that hasn't been from California or Florida. Furthermore, Bob will be the youngest US Olympic Windsurfing Representative since Olympic Silver Medalist Mike Gebhardt in 1988. Windsurfing has been an Olympic sport since 1984.
