Konesky was born and raised in Columbus, Ohio, where he performed in a band with friend John Spiker. Through a mutual friend, he and Spiker met Tenacious D guitarist Kyle Gass, who was recruiting musicians for his Trainwreck side-project. In 2003, Konesky and Spiker would both re-locate to Los Angeles and become the electric guitarist and bassist for Trainwreck. In 2005, Konesky and Spiker performed on the second Tenacious D album "The Pick of Destiny" and would then perform live on "The Pick of Destiny Tour", making them (alongside drummer Brooks Wackerman) additional live members of Tenacious D. In 2010, Trainwreck split up, which lead him and Gass to form Kyle Gass Band. In 2009, Konesky and Gass also worked on "Guitarings", their own YouTube channel. In 2012, Konesky formed Wynchester alongside Kyle Gass Band frontman Mike Bray. Konesky would also continue to record on the third and fourth Tenacious D records - "Rize of the Fenix" (2012) and "Post-Apocalypto" (2018). In 2015, Konesky won a Grammy for his recording of Tenacious D's recording of "The Last in Line" for a Ronnie James Dio tribute album. Konesky would also reprise his role in Trainwreck when they re-assembled in 2018.