 Hollins began business as a marine insurance broker, and became a banker in 1888.At one time he was a partner of Fernando Yznaga whose sister Consuelo Yznaga was the Dowager Duchess of Manchester In fact, he was along with close friend William K. Vanderbilt, the executors of Yznaga's will Along with Eugene Zimmerman of Cincinnati, Ohio, the father of the Duchess of Manchester, had owned an interest in a number of properties in the Midwest.These properties included Superior Colliery Company and Superior Development Company.