Deal Maker

An awning manufacturer, a candy maker and a cruise ship company seemingly have little in common.

But in the world of David Hoffmann — his family business, Chicago-based Hoffmann Commercial Real Estate, is the largest commercial property owner in downtown Naples in terms of square feet — the tie-ups make sense.

While Greg Hoffmann, David's Hoffmann's son, handles much of the real estate investing, the elder Hoffmann runs Osprey Capital LLC. That entity, a private family office structure that's grown popular among high-net-worth individuals of late, is a $2 billion fund with worldwide holdings everywhere from oil distribution to aviation and winemaking. The Wilmette, Ill.-based fund, according to its website, aims to double its assets in the next six to eight years through organic growth and acquisitions.