Bolli started playing on the Nationwide Tour (now Web.com Tour) full-time in 2004 and moved up to the PGA Tour in 2005. In his rookie season on the PGA Tour, he only made 9 of 24 cuts with his best finish being tied for 17th at the Southern Farm Bureau Classic. He moved back to the Nationwide Tour in 2006. He finished in 8th place on the Nationwide Tour's money list in 2007 to earn his PGA Tour card for 2008. He was not able to retain his PGA Tour card in 2008 and returned to the Nationwide Tour in 2009. He won the Price Cutter Charity Championship in August 2009, his third victory on the Nationwide Tour. He finished 11th on the money list to earn his 2010 PGA Tour card.
Bolli lost his Tour card in 2010 after only making 4 cuts in 23 events. He played on the Web.com Tour for two years and was 44th on the 2012 money list going into the season finale. Bolli won the final event, moved up to ninth, and regained a PGA Tour card.
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