Careers Under Construction

Some of the hardest conversations Jamie Wilson has walked into have started with people yelling at him. His approach? Listen, understand where people are coming from, and find common ground.He started his career as a teacher before becoming a U.S. Army Ranger, Treaty Commissioner, Deputy Minister, and eventually the first Indigenous Chair of the Manitoba Hydro board. Today, he serves as VP of Indigenous Strategy, Research & Business Development at RRC Polytech.In this episode of Careers Under Construction, Jamie shares:How he got into BMX racing and became a professional racerHow he went from teaching to the U.S. Army RangersHow the Jay Treaty of 1794 played a role in his path to the U.S. militaryWhat Ranger training taught him about leadershipHow he helped get a new high school for his communityHow whitewater rafting and cliff jumping in New Zealand led to a career-changing decisionHow he handled tough conversations and angry town hallsWhy Manitoba needs to take more risks when it comes to innovationThe 5000 / 50 / 5 goals he sets at RRC PolytechJamie says he often questioned whether he was ready for bigger leadership roles. Watch the full episode to hear how he learned to believe in himself.

Three days after David Asper started practising criminal defence in Winnipeg, he was pulled into his boss’s office. Joyce Milgaard was sitting there. Her son David had already spent 17 years in prison for a murder he said he didn’t commit.A six-year fight followed, culminating in an April 1992 Supreme Court of Canada decision. Later DNA testing confirmed another man was responsible.After helping win Milgaard’s freedom, David walked away from criminal law.In this episode of Careers Under Construction, David shares:How he challenged the Crown’s version of the Milgaard murder using a camcorder and crime scene reenactmentWhy he left criminal law after the biggest win of his careerWhat really happened at Canwest Global and his dad’s warning: “Never build empires, because empires never survive”Becoming chair of the Blue Bombers during years of financial and operational strugglesWhy fans wanted legroom, bathrooms, concessions and a better game-day experienceGetting cut out of his stadium deal after investing more than $6 million — while in Churchill watching polar bears with his wife and no cell serviceWhy he reconsidered retirement and started a professional basketball team after meeting immigrant families across the country• The double meaning behind the Sea Bears logo — “I’m back”Why he believes failure teaches more than successFrom freeing David Milgaard to building businesses and bringing pro basketball back to Winnipeg, David Asper has left his mark on the city.

Krystyn MacKinnon started her career in banking at 19 and became an assistant branch manager a year later.She went on to help launch a title insurance startup across Western Canada, lead 100% commission sales teams, and is now Principal at Colliers Project Leaders—with no technical background in engineering or project management.In this episode of Careers Under Construction, Krystyn shares:The feedback that changed how she leadsWhy she had to learn to lead herself firstHow achievement became tied to her identityHow a startup and layoff changed her careerThe “will vs. skill” question she uses with underperformanceWhy leaders can’t create motivation in othersHow she turned her personality down from a 10 to a 4Why psychological safety comes before high performanceWhy she never wants to be the subject matter expert#CareersUnderConstruction #Leadership #Winnipeg #PsychologicalSafety

Catch Fire Group helps mid-sized business owners sell the companies they’ve spent a lifetime building. Gary Brownstone’s job is to help owners see their business the way a buyer does.Sellers look back at the sacrifices, risks and legacy they’ve built. Buyers look at cash flow, growth and what happens when the founder leaves.In this episode of Careers Under Construction, Gary shares:Why he never puts a price on a business and lets the market decideThe question every owner should ask: “If I disappeared for 30 days, what would break?”Why one seller accepted $1.5 million less to protect his employees and legacyWhy “sellers look back, buyers look forward”Why Gary tells owners “their baby is ugly”Why recurring revenue can be worth more than a bigger top lineWhat drives a multiple — and why American strategic buyers often pay the mostBecause for most owners, the number Gary gets them isn’t just a payout — it’s the rest of their life.

Those little paint colour cards you flip through at the hardware store? There's a good chance they were made by one family right here in Winnipeg. The Duha Family.Rick's first job in the family business was screwing posts into paint fan decks.Now, a robot does it.Rick isn't buying robots to replace his team. He's buying them to replace the repetitive tasks.That's where people get AI wrong. It's not about replacing people — it's about making time for the tasks that keep getting pushed down your to-do list.At 16, Rick wanted out. The Duha Group, the family paint-chip business, seemed boring. When he came back, he realized he'd been looking at it all wrong. Today, Duha is the world's leading paint-chip manufacturer.In this episode of Careers Under Construction, Rick shares:How a Winnipeg garage became the world's leading paint-chip manufacturerWhy paint companies can't make their own paint chipsWhy he left and what brought him backThe mistake that taught him the mostDuha's unique employee training systemWhy "Ready. Fire. Aim." became the company's mindsetWhat it took to buy their biggest competitorWhy he believes AI will create better quality jobs, not eliminate themHow did the son who couldn't wait to leave the family paint business become the 11th Duha to run it?