Pete Smaluck is the founder and CEO of props.cash, a research platform that gives sports fans and gamblers an edge in the sector, which has grown exponentially since the 2021 legalization of single-game bets in Canada. A trained teacher, Pete originally developed his software to teach middle-schoolers math through NBA stats. But he couldn’t convince school boards in Ontario to pay for the software, so he found a new approach to make his tool valuable. Three years in, props.cash now has tens of thousands of users across 30 countries. It’s also one of the highest-grossing sports apps on the Apple App Store. In this episode, Pete discusses how he was able to redirect his user base from kids to adults, why simple design is so difficult to achieve, and what he thinks about the stigma around sports gambling.

Emily O’Brien is the founder of Comeback Snacks, a gourmet popcorn company designed to give former convicts a second chance. After a series of bad judgment calls that landed Emily in jail, she learned firsthand about the challenges she and her fellow inmates would face in gaining employment once they were released. In this episode, Emily talks about the riveting origin story of her business, and the uphill battles she faced trying to scale it — fresh out of prison.

 Joanna Griffiths is the founder of Knix, the popular underwear and apparel brand, which she started in 2013. The company made a name for itself by focusing on leakproof underwear and talking openly about the reality of women’s bodies — a very different approach from industry titans like Victoria’s Secret. Knix is a booming business with profits of more than $130-million. But like most good ideas, the road to success hasn’t always been straightforward. In this episode, Joanna shares how a key moment of rejection from a previous employer forever changed her career trajectory, how she fought for people to see the value of her vision, and when she last had what she calls “failure champagne.”  

Ten years ago, the idea of being the CEO of her own company wasn’t something even remotely on Jenn Harper’s radar. But several personal struggles and tragedies changed the path of her life and inspired her to found Cheekbone Beauty — Canada’s first Indigenous-owned and founded cosmetics company. Now, the company has its products on shelves in stores across Canada. It didn’t come easy, though. From being rejected on Dragons Den to being initially turned down by Sephora, Jenn has had her fair share of rejection. In this episode, she talks about how Cheekbone was born out of grief, why inexperience can be an asset, and the struggles Indigenous entrepreneurs face in building and growing a business.

Bruce Linton was the founder and co-CEO of Canopy Growth, the first publicly traded cannabis company in North America. When weed first became legal in Canada, Bruce was riding the high. Under his leadership, Canopy grew into a company valued at around $18-billion. Bruce, in many ways, became the face of the cannabis boom. But things ended badly between Bruce and the company he created.  Cannabis sales failed to meet the hype and in 2019, he was fired by the board. So what led to one of the most public business failures in recent memory? Bruce talks about how he got fired, why the cannabis sector hasn’t delivered on its colossal promise and what’s next for him.