Through his importing business, von Mandl saved up enough money to buy his first vineyard, Mission Hill, at 31.

Von Mandl said in 2003 that, at the time, he wondered "if I had made the biggest mistake of my life" in buying the winery, Bloomberg reported.

Von Mandl also starting selling hard cider that he described as "awful" to help cover the cost of operating the winery, according to Business in Vancouver. Unlike other Canadian breweries, von Mandl did not reuse the glass bottles the cider was sold in and relied on other businesses' buyback programs to help his company meet national waste regulations. When breweries that previously used the same bottles as von Mandl stopped buying back the cider bottles, the Canadian government fined the business "several million dollars," Business in Vancouver reported.

The financial strain of the bottle fiasco led von Mandl to start brewing a beer called Clark's Great Canadian Beer, according to Business in Vancouver. Von Mandl also opened another business on Annacis Island in British Columbia focused on sustainability called Turning Point Brewery.