From September of 1972 until May of 2015, Bob owned and operated Bob’s Shoe Repair in Wayzata. He says with a smile, "I have a long history of saving soles and heeling people." In 1996 he started “Bob’s Sleepout” which began as an effort to help the needy people in Wayzata. After the first year the effort merged with Interfaith Outreach and Community partners and became a conduit to raise money, awareness, and involvement around the affordable housing and homeless issues in the eight west-metro communities that Interfaith serves.
As of December of 2019, it had raised over 30 million dollars and has prevented homelessness over 33,000 times. Bob also served as a deacon for three years at Wayzata Community Church. He especially supports NewPath's vision of removing stigmas and barriers to obtaining mental health services.