Ray Hartmann, ex-owner of alternative paper the Riverfront Times and a former owner of St. Louis Magazine, has filed for bankruptcy, the St. Louis Post-Dispatch reported.

Hartmann and his wife have assets of about $65,000 and creditors who are owed more than have $1 million, according to the filing, says the paper. 

Hartmann said he made “one really big catastrophic commercial real estate investment,” the paper said.