Jon Montgomery, Canadian Olympic skeleton champion and beer-chugging Games charmer, held hands with a mother and son he’d agreed to meet at a downtown Toronto restaurant. It was spring 2015.Pat Macdonald and her elder son, Ian, had co-founded a new craft beer business called Old Tomorrow. A nod to the nickname of Canada’s first prime minister, Sir John A. Macdonald — no relation, but a soul who also enjoyed lifting a glass or two.Pat had a test batch bottle of their new rye-infused, oak-aged beer in her purse. Montgomery drank the smuggled brew. The Macdonalds hoped their celebrity guest — whom they’d pitched via Twitter, fingers crossed that he’d respond — would endorse an ale they created for him. For the newbie brewers, Montgomery personified Canadian pride and spirit.“It was a crazy idea,” said Ian, 32, of pursuing the Olympian who, after the 2010 Vancouver Winter Games, became host of The Amazing Race Canada.“Obviously we’re proud to be Canadian. That’s why we started this company.”The Macdonalds — Ontario’s only mother-and-son craft beer co-founders — left successful customer-centric careers to pursue an interest in beermaking. They entered the crowded craft landscape in 2014 when Pat, off work with a broken ankle, accepted Ian’s suggestion to build a family company from scratch. The original idea: it was something they could have fun with in their spare time. And oh, they’d need to put up $40,000 each as seed money. Now, they were banking on Montgomery’s star power to distinguish their suds from everyone else’s.Montgomery liked the product. He liked the Macdonalds. “The beer was delicious and Ian and his mum were bright, eager, and checked all the boxes for the type of people you’d want to work with,” Montgomery said.Hands were clasped, a gesture of faith, in lieu of a contract. Time was too short for a formal deal, not ...
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