Careers Under Construction

Early in his career, Cole Akerstream was working in commercial real estate on 100% commission, waiting months for deals to close.Today, Cole is Vice President of Facilities and Store Development at The North West Company, a 360+ year old Canadian company with roughly 230 stores across northern Canada, Alaska, the Caribbean and the South Pacific.In this episode of Careers Under Construction, Cole shares:What playing junior hockey, going to university and selling TVs at Future Shop taught him about closing and relationshipsWhat the financial uncertainty of his early commission years really looked likeWhy he walked away from commission sales and took a pay cutHow a failed Giant Tiger deal ended up changing the course of his careerHow he built the kind of trust that opens doors in remote communitiesWhy chiefs and community leaders sometimes skip the chain and call him directlyThe night he had nowhere to sleep in Old Crow and an elder took him inThe young boy in Alaska who had never seen an orange beforeWhy he believes you should write your goals down and keep them to yourself

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.