Since then, he's devoted most of his efforts toward making the locally based consumer-ratings firm Angie's List into a fast-growing success. Oesterle's idea of a break? He took time off in 2004 to lead Gov. Mitch Daniels' first election campaign.
For several years, Oesterle, Angie's List CEO, also has been quietly attempting to revitalize the near-east side.
Since Angie's List moved its headquarters to 1030 E. Washington St. in 2001, its sister company Henry Amalgamated LLC has acquired 22 dilapidated houses, empty lots and other properties in the Holy Cross neighborhood.
Oesterle expects to double its holdings there by 2013. The city of Indianapolis is on board with Oesterle's revitalization vision. This year, it removed the highway ramp that had split the Holy Cross neighborhood for years.
Meanwhile, Angie's List continues growing at a torrid rate. The firm raised $53 million in venture capital in 2008 and plans to double its 400-person work force within five years.
Oesterle also made news in the Meridian-Kessler neighborhood in 2008. In July, he paid nearly $1.5 million to buy Holy Trinity Greek Orthodox Church. Oesterle is renting the place to the Indianapolis Opera to use as a multi-function center providing rehearsal space, classes and small performances. He plans to turn ownership over to the opera eventually.
"I would have been hard-pressed to tell you much about the Indianapolis Opera before all of this," Oesterle told IBJ. "But I think they'll be great neighbors."
Oesterle lives on Washington Boulevard, directly north of the church parking lot. Neighbors had been concerned about who would move into the church since 2005, when leaders of the Greek congregation announced plans to build a new facility in Carmel.