Hollenbach received his Bachelor of Arts from the University of Kentucky at Lexington in 1982 and his Juris Doctor from University of Louisville School of Law in 1985. He is a graduate of Trinity High School, an all-male Catholic high school in Louisville, Kentucky.
A Democrat, he was elected as treasurer in 2007 and re-elected in 2011. Hollenbach was an attorney in private practice from 1985 until his 2007 election as Treasurer. Hollenbach was also commissioner of the Kentucky Commission on Human Rights from 1999 to 2007.
In 2011, he successfully ran for a second term as treasurer against Republican K. C. Crosbie and Libertarian Ken Moellman.
During the lead-up to the 2015 elections, he said that he might run for another office but did not immediately target which office. Because the incumbent had resigned after the filing deadline for the primary election and had drawn no primary opposition, a total of twenty-one candidates contested the seat.
Runoff elections are not held in Kentucky in such cases. Plurality prevails.
Because of term limits, Hollenbach was ineligible to run for a third term as treasurer in 2015 and instead won election to a vacant seat on the Jefferson County, Kentucky District Court in 2015. Hollenbach won his initial election as treasurer against Melinda L. Wheeler in a landslide election in 2007 and took office as the 37th Treasurer in January 2008. In the 2015 general election, Hollenbach won election to a vacant seat on the Jefferson County District Court. Hollenbach won with just over 19 percent of the vote. The runner-up with 11.6 percent of the ballots cast was the Republican Bob Heleringer, a former state representative from Louisville.
He was also a member of the bi-partisan Blue Ribbon Commission investigating the Merit Hiring System.
