Caddyswag was formed after a hot tub party and the legendary Puma Open golf tournament in Chicago, circa 2006. After a few months of some research and development Caddyswag placed its first trial order. Stocked with 1,000 units for November in Minnesota, Caddyswag was able to sell them all prior to Christmas and the ball was rolling. Since then Caddyswag has been credited with many gorilla style appearances like driving golf carts from Chicago to Minneapolis to raise money for charity to Celebrity events both on and off the golf course and even an unintentional bomb scare at the Merchandise Mart.

Caddyswag's most notable appearance came in 2011 on Season 2 of the ABC hit series Shark Tank. The Sharks did not take the bait, but they did shine a bright light on Caddyswag's very practical money saving idea for all golfers: the Par-6, an ice-less cooler that fits inside any golf bag and stays cold for 18 holes.

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