RESIDENT EXPERT
EXPERT & Expert
WILLOWS: From Lemonade to Legacy ENTREPRENEURSHIP CHOSE HIM
Led by his entrepreneurial spirit, Willows began working on his first “real” business when he was 18 years old, along with his business partner and class- mate Zach Isaacs. In 2014, the duo set their sights on developing an alcohol company that opened to the public in early 2017. Shrugging Doctor Beverage Company, Manitoba’s first-ever commercial wine vineyard, continues to grow from the young entrepre- neurs’ initial $50 investment. Willows and Zach grow specially engineered hybrid wine grapes that survive Manitoba’s cold winters at their Pembina Valley vineyard. From there, they use these grapes to make wine at their winery in Winnipeg, along with wine from other Prairie fruits. Adding to their offerings, they make cider from local apples and mead from local honey. They also create sangria and wine coolers, which they serve from their restaurant and wine bar in sunny St. James. In 2023, Willows used his business experience and accumulated capital from the successful wine project to begin acquiring and operating more businesses. To start, he acquired Winnipeg’s Maple Leaf Rubber Stamp, a manufacturer of rubber stamps and other engraved items. The owners of the long-standing company, which was founded in 1932, were ready to retire and wanted to pass the torch. In 2025, Willows acquired 114-year-old CanMark Industries, which is another custom engraver and stamp-maker. Willows is not yet 30 and runs all three companies — and since business is his ultimate passion, he plans to continue acquiring, running and growing businesses for the rest of his life.
WILLOWS IN 2025
W illows Christopher, often referred to interest in business sparked at a young age — he launched a lemonade stand at age five and ran it for many summers before beginning a freelance vide- ography business at just 13 years old. He was never interested in formal education and graduated high school with a 48 per cent average that the administra- tion rounded up to a 50 per cent passing grade so they “wouldn’t have to see him again.” mononymously as “Willows,” is a lifelong entrepreneur based out of Winnipeg. His
SOCIALS: • Willows’ Winery: ShrugDoc.com | @ShrugDoc • Willows’ Stampery : MapleLeafRubberStamp.ca | @MapleLeafRubberStamp • Willows’ Engraver: CanMarkIndustries.com | @CanadianMarking • Willows’ personal social media: @VoteWillows • Willows’ finance brand: @DrunkDividends
SAVOUR MANITOBA | SPRING 2026 | 5
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