In 1982 ex-Braniff Airlines pilots and executives tapped Mr. Daly to lead them through the process of forming a new Minneapolis based charter airline called Sun Country.
Robert assisted the group in obtaining its operating certificate from the Civil Aeronautics Board and held an equity interest in the airline until it was sold in 1988.  In 2001, Sun Country was forced into bankruptcy after the 9/11 impact on the airline industry.  The Sun Country executive team once again called upon Robert to put an investor group together and negotiate a purchase of all critical Sun Country assets out of bankruptcy.  This time around Mr. Daly served as Chairman of the Board and led the company from bankruptcy into record profitability until it was sold in 2006.

Robert began practicing law in Dakota County, MN in 1960 and continued his general practice through 1993 specializing in residential and commercial real estate.  Mr. Daly transitioned from practicing attorney to real estate developer specializing in single and multifamily housing, and commercial developments.

Robert has helped take small businesses public, worked on international power plant projects, and invested in and served as a trusted advisor for numerous other businesses including restaurants, automotive businesses, and gas stations to name a few.
In addition to practicing law, developing real estate, and running an airline, Robert ventured into the gaming industry in the early 90’s. Hired by former Green Bay Packer great Max McGee, Mr. Daly financed, built, and managed two casinos for the HoChunk Nation in Wisconsin (formerly the Wisconsin Winnebago). He later joined with his son, Matt, to pursue and develop additional gaming projects on the West Coast throughout the 90’s and early 2000’s.