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Diana Stirling

Founder, OnTrack Media and Insider Trading GroupOwner, LocoLanding Adventure Park
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, Diana Stirling

Two hours after the birth of her first child and still in her hospital bed, Diana Stirling signed papers to incorporate a second business.

“At that point we just didn’t believe that anything stopped for business,” said Stirling of her entrepreneurial ventures with business partner Shannon Ward.

It was 2006. Already Stirling had helped grow the duo’s first business – marketing and design company OnTrack Media – to 13 employees and over $1 million in annual revenues. The incorporation documents would launch a second company: Insider Trading Group, which provides affinity programs.

But while Stirling had planned her trajectory carefully, with an earlier sales and marketing career driving her entrepreneurial success, she became dissatisfied with traditional business success in 2007 – as did Ward.

“It was basically making us miserable at that point.”

Both pregnant, the duo invented their own triple bottom line: finances, freedom and fulfilment. They applied the concept to their businesses, honing in on their most profitable revenue streams, moving to contractors for more accountable labour and creating a virtual office through early forms of cloud-computing technology.

“We completely tore down that business and rebuilt it based on a different model,” Stirling said.

After rebuilding the businesses through the recession, Stirling said they’re now back up to their former strength – but built on a model that has created more time and flexibility. The business partners call the concept “pretirement living” and now run a blog and do speaking engagements on the topic.

Stirling said her two ventures, along with family business LocoLanding Adventure Park in the Okanagan, now have 35 staff and revenues of “over seven figures.”

“I’m loving what I’m doing,” she said. “I’m loving building businesses, but I’m building them in a way that gives me and my family freedom and fulfilment and the ability to do things that really seemed impossible before.” •