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From moving out of the house when she was 14 to the top of the corporate ladder, Heather’s story teaches us to always focus on what you have and not what you don’t.  She was in the thick of things in tech world during early 90’s, selling some of the most disruptive technologies to hit the mass market. After starting her own business and scaling it she is now focused on helping other women entrepreneurs do the exact same thing.

You may not know Murray Foster by name but if you’ve listened to the radio in Canada at any point since 1989 you know his work.  In the early 90’s Moxie Fruvous were the darlings of the Canadian music scene, that is until Nirvana released Nevermind.  Murray talks about how the band went from headliner to “butt of the joke” literally overnight.  And just when he thought his career in music was over, a phone call from Great Big Sea took him on another decade-long run, this time as a hired gun.  He’s a musician, he’s a filmmaker, a songwriter and is currently working on his own musical.  

Jay Onrait is a Gemini Award-winning sportscaster for his work on TSN’s Sportscentre.  Thanks to their unique personalities and style, he and his co-anchor landed their own show on Fox Sports in Los Angeles (which as you will hear didn’t go exactly as planned) and now they are back north of the border as the undisputed kings of Canadian sports television.  Jay didn’t become a Canadian broadcasting icon overnight though and actually, he almost became a pharmacist, more on that in a few minutes.   From Athabasca Alberta to Los Angeles and everywhere in between, find out how a stroke of luck and a “right place at the right time” moment led to the break that jump-started his career.

Jane Roos is the founder of CANFUND, a charity that raises money support Canadian Olympic Athletes.  As a teenager, she had it all.  She was a rising track superstar, she was a model, she had an amazing family and great friends.  But as you will hear, one snowy night between Ottawa and Montreal everything changed a blink of an eye.   Jane’s story is real, it’s raw and it’s inspiring. Hear how she has taken a tragedy that would crush so many people and used the lesson life has given her to dedicate her life to helping others fulfill their dreams.

Saul Colt is the world's best word-of-mouth marketer. He is the driving force in Canada behind brands like ZipCar and Freshbooks.  He built and sold his own comic book company all while running his family business for years. Saul has not had a traditional path to success as you will hear, but the lessons he has learned along the way about himself are extremely impactful.  He tells us the story of how he went from making himself almost impossible to hire, to having companies apply to him for his services. He now runs an idea company and works with some of the worlds biggest brands, but as you will hear, it’s a long way from his family’s corrugated box company to being written about in New York Times best sellers.

Matt Basile is a chef, an entrepreneur, and a big-time personality.  He is the star of “Rebel Without a Kitchen” on Netflix and his best selling cookbook “Street food Diaries” is available on Amazon.  His restaurant Lisa Marie is a critically acclaimed mainstay in the Toronto food scene and he was a pioneer with his first venture Fidel Gastros. Matt talks candidly about the ups and downs of the food business and how he has carved out his brand to where it is today.  He’ll educate us about the time he got fired and how it was probably the luckiest thing that’s ever happened to him. And we’ll talk about how to build a business when the banks say no and your best friend tells you, with love, there’s not a chance your plan can possibly work. What I love about the path Matt has carved to success is the fact he’s done it in a field he himself created. There wasn’t such a thing as a pop-up restaurant in Toronto with a Chef who entertained you as well as made great food. There wasn’t a model for Fidel Gastro’s to follow until he created the model himself.

Dr. Sean Wise comes with a list of titles and accomplishments including lawyer, author, professor, investor, mentor and the list goes on. Today he’s most well known as a leader in the Canadian Start-up community as the National Fellow for Startup Canada’s Startup Communities. Over the next hour you’ll hear how he has had to overcome a learning disability and how he was able to prove everyone wrong on his way to success. Sean’s story is remarkable and sheds light on some very big topics from mental health to building on lessons of the past to power through the troubles of today. Sean gives some behind the scenes stories from the early days of Dragon’s Den where he was an advisor and we dig into Sean’s book “Startup Opportunities” where he and fellow investor Brad Feld talk to startups about how, when and what to pitch.

“The land of misfit toys,” is how Michael Wekerle describes the small group of friends he partnered with to create GMP Securities, a Toronto-based boutique investment firm. Although the cynics had their doubts, within a short period, the firm became a trading powerhouse. Its legacy includes some landmark capital-raising campaigns including Sherritt International and Research in Motion, which GMP took public in 1997. In Canada, Wekerle “Wek” is a bit of a celebrity. In the 80s and 90s, he earned a reputation as the greatest trader on Bay Street with elephant-like memory. Later, he leveraged his Bay Street smarts to foray into a few new ventures. Today, he’s a Dragon investor on the hit CBC show Dragons’ Den. In our inaugural podcast with Randy Cass, Michael speaks candidly about what drives him to succeed, overcome struggles and become a better person. Know the rules The core secret to Wekerle’s success is simple. He takes the time to understand the rules of engagement. “You can’t do anything unless you know the rules.” In 1986, when Sherritt International, a Toronto-based mining company with operations in Cuba, was looking for a partner to help it raise capital, no one wanted to get involved because of the sticky Cuban issue. But Wekerle and his GMP team took a closer look at the U.S. economic embargo that banned companies with ties to Cuba from doing business in the United States. This extra due diligence helped them understand how they could work around this issue. As a result, their alliance with Sherritt International became one of the biggest deals in Canadian history. Make Money Slow “It takes five years to build a business and another five to create a brand,” is something Wekerle often repeats. This perspective helps temper his expectations and prevents him from giving up quickly on new ventures. In 2012, when he founded Difference Capital, a merchant bank that invests in technology, media, and healthcare companies, the first few years were hard. Wekerle believed this was because the Canadian market was not ready to invest in start-ups. And in turn, the company’s stocks were unfairly punished. But never one to believe in overnight success stories, he remains optimistic that over time he and his management have been able to develop better execution plans that will put the company on a steady growth trajectory. Have a heart As Difference Capital struggled, Wekerle was also mourning the loss of his wife. It was during this dark period that he realized some people would only stick around when things were good. This lesson taught him to be a better person in life and business. It reinforced his core values of empathy and reciprocity: “Always treat people the way you want to be treated.” But it also reminded him not to be complacent, “When things are going well, start taking defensive action, put more capital in the bank for your company….” Spot the trends Over the years, Wekerle has worn many different hats― astute trader, successful entrepreneur, maverick television personality. Some of the career pivots were by design, others just happened. The Dragons Den opportunity, he admits, came out of left field. But, this role opened his eyes to the trends in Canada and around the world and fed his proclivity for technology. His recent ventures reflect his vision of the future. He is in the midst of converting El Mocambo, a famous Toronto music club, into a world-class recording studio that produces content for streaming. In recent years, he also acquired some former Blackberry buildings in Waterloo and transformed them into an innovation hub for starter technology companies. Like his role in Dragons Den, Wekerle plans to support and nurture some of these companies. “It’s about making a difference and changing the way we do things .”