After building national retail chains and venturing into agtech and cleantech, Calgary entrepreneur Darren Bondar is returning to familiar territory — the watch business.
Bondar opened The Story Shop, the first retail location for his revived watch and lifestyle brand MEDIUM, at CF Chinook Centre on October 30. It marks the 150th store of a career that includes building WATCH IT! and Spiritleaf.
Bondar, whose entrepreneurial journey has been covered previously by Calgary.tech, originally launched MEDIUM in 2016. He reacquired the brand earlier this year, with plans to rebuild it around a new identity and leverage technology to speed the rebuild.
“Watches and retail are familiar territory for me,” Bondar said. “Reacquiring MEDIUM was an opportunity to return to something I helped create and give it a clearer identity.”
A Store Built Around Stories
MEDIUM’s philosophy, Stories Worth Wearing, reflects the idea that a watch can represent meaningful moments in people’s lives, from major milestones to personal comebacks.
The new Story Shop takes that concept beyond the products themselves.
Visitors to the store can take part in a complimentary Story Studio experience, sharing a meaningful personal story, having their portrait taken, and receiving a printed keepsake. Customers can also share their stories through MEDIUM’s online Story Builder.
“AI is helping us move much faster in developing marketing content, exploring creative concepts, and refining how we tell the MEDIUM story,” said Samantha Down, who leads the company’s marketing. “The technology is there to support the customer experience, but not replace it. We’re using all the new capabilities to build a brand that remains personal, authentic, and connected to people’s lives.”
Techie Approach to Building a Business
While Bondar’s return to retail draws on decades of experience, the technology available to entrepreneurs has changed considerably.
He has made OpenAI’s ChatGPT and Anthropic’s Claude central to building MEDIUM, using the AI platforms across brand strategy, product development, website creation, marketing, hiring materials, and day-to-day operations.
The tools help him brainstorm ideas, develop content, create operating processes, and work through business decisions. AI image generation also supports the exploration of visual concepts and creative directions, while Shopify and Shopify POS power MEDIUM’s online and in-store commerce operations.
“The biggest difference is how much I can work through directly — from exploring an idea to developing copy, creative concepts, and operating materials,” Bondar said.
These technologies allow Bondar and his small team to move ideas forward more quickly and develop materials before bringing in outside resources.
His approach reflects a broader shift among small business owners. An October 2026 Goldman Sachs survey of small business owners found that 55% of respondents using AI applied it to strategy and business development.
Bondar hasn’t formally quantified the time or cost savings, however, and notes that traditional investments in inventory, a physical store, and people remain essential.
“Experience and judgment still guide the decisions. AI helps me work through ideas and get them into execution faster, giving a small team the capacity to accomplish more,” Bondar said.
For an entrepreneur who has spent decades building businesses across different industries, MEDIUM represents an opportunity to apply new technologies to a familiar challenge.
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