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 racer How he went from teaching to the U.S. Army Rangers How the Jay Treaty of 1794 played a role in his path to the U.S. military What Ranger training taught him about leadership How he helped get a new high school for his community How whitewater rafting and cliff jumping in New Zealand led to a career-changing decision How he handled tough conversations and angry town halls Why Manitoba needs to take more risks when it comes to innovation The 5000 / 50 / 5 goals he sets at RRC Polytech Jamie 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 reenactment Why he left criminal law after the biggest win of his career What 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 struggles Why fans wanted legroom, bathrooms, concessions and a better game-day experience Getting cut out of his stadium deal after investing more than $6 million — while in Churchill watching polar bears with his wife and no cell service Why 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 success From 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 leads Why she had to learn to lead herself first How achievement became tied to her identity How a startup and layoff changed her career The “will vs. skill” question she uses with underperformance Why leaders can’t create motivation in others How she turned her personality down from a 10 to a 4 Why psychological safety comes before high performance Why 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 decide The 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 legacy Why “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 line What drives a multiple — and why American strategic buyers often pay the most Because 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 manufacturer Why paint companies can't make their own paint chips Why he left and what brought him back The mistake that taught him the most Duha's unique employee training system Why "Ready. Fire. Aim." became the company's mindset What it took to buy their biggest competitor Why he believes AI will create better quality jobs, not eliminate them How did the son who couldn't wait to leave the family paint business become the 11th Duha to run it?

Kyle Romaniuk is a serial entrepreneur who started selling T-shirts on consignment at just 10 years old before launching his own design agency straight out of Red River College. That agency grew into Cocoon Branding, where he worked with brands like Red Bull and GoodLife Fitness. When COVID wiped out 80% of his agency's revenue, Kyle changed direction and launched FRAKXION. In this episode of Careers Under Construction, Kyle shares: How he started his first business at age 10 and built a successful design agency. Why losing 80% of his revenue during COVID led him to start FRAKXION. What "operational quicksand" is, and why so many business owners become the biggest roadblock in their own companies. How surviving childhood cancer led to a full-circle moment with the organization that granted his childhood wish. Kyle is also the author of Embark , a book about helping leaders build stronger teams and better workplaces. Grab a copy of Embark , learn more about FRAKXION by hitting play.

In 2018, 20-year-old Hailey Dugay was sitting in the back seat of her boyfriend's truck, heading home with friends. Earlier that night, Jesse Paluk had been involved in an altercation at a bar near Fraserwood. Later, when three vehicles approached on a gravel road, Paluk stood in the road holding a rifle and told William Comber to have his back. What no one inside the truck could see was Comber standing off to the side. As Hailey's boyfriend drove away, several shots were fired. A bullet from Comber's hunting rifle struck the truck and hit Hailey. Her boyfriend rushed her to the hospital, but she did not make it. It took almost a year for Dana to learn who fired the shot that took her daughter's life. Years later, Manitoba's highest court reduced Comber's second-degree murder conviction to manslaughter. The court found there wasn't enough evidence to prove he intended to harm someone inside the truck rather than damage the vehicle. In this episode of Careers Under Construction, Dana shares what happened that night and why it took nearly a year to learn the truth, how a jury ended up being selected from a Walmart parking lot and how Hailey's Way has supported more than 100 youth across the Interlake. To support youth programs in Hailey's memory, follow Hailey's Way on Facebook and Instagram.

Dale Weise was cut multiple times during junior hockey before going on to play 513 regular-season NHL games. Today, he buys and grows established businesses in Winnipeg. In this episode of Careers Under Construction, Dale shares: How getting cut built his determination The time he thought he made the Rangers, only to be cut two days before opening night How he recorded the fastest Gordie Howe hat trick in Philadelphia Flyers history Why signing a four-year, $9.4 million contract with Philadelphia didn’t go as planned Getting traded while his wife was eight months pregnant with twins Why a business he opened in March 2020 became one of his biggest lessons How looking at approximately 1,000 businesses led him to buy established companies instead of starting from scratch Watch the full episode to hear Dale’s journey from the NHL to business ownership.

Jenna was studying to become a dentist when she watched an episode of Cake Boss and decided to make a cake just for fun. She made it in the tiny apartment she shared with her twin sister Ashley. She was hooked right away. Then a competitor called the city on her. That push forced her to turn a hobby into a real business. Today Jenna and Ashley run Jenna Rae Cakes: 4 locations and around 40 employees, heading into their 12th year Grew from Jenna's solo custom cake business into a full lifestyle brand with two national bestselling cookbooks Plus their Dazzle Dust edible glitter and Liquid Flavours product lines Jenna stepped away from a path toward dentistry and a hockey career at the University of Manitoba to chase cakes Ashley is a graphic designer who built the logo, website and visual brand and was named a 2025 WXN Top 100 Award winner Featured as judges on Wall of Bakers on Food Network Have collaborated with brands like Coach, Mercedes-Benz and Smirnoff Ice, partnered with Loacker for its 100th anniversary, and worked as food stylists on a Hallmark movie

Jaime Mann believes one thing above all else: connection isn't soft, it's strategic. As a keynote speaker, leadership coach and partner in a construction company, she blends psychology, leadership and a little sass to help people lead with more clarity, courage and confidence. In this episode of Careers Under Construction , Jaime shares: Why connection is one of the most overlooked leadership skills What years of anxiety, loss and perfectionism taught her about looking fine versus actually being fine The two-word email that made her realize how much perfectionism was quietly stealing from her Why beating yourself up never works and what the science says to do instead• How to befriend your inner bully instead of letting it run your life Why she decided to go back for her master's degree at 47

In 2019, Jason Tyler McLean put a brand new gun in his mouth and pulled the trigger. It jammed. The odds of that happening are one in millions. He woke up the next day, wrote himself a letter and made a promise he has kept ever since. Long before he became a coach, Jason was just trying to make it through each day. Drugs at 13. The streets of Winnipeg at 15. Gangs. A sales career that brought financial success, but not peace. Then a two-year battle with depression brought everything to a breaking point. After his attempt, he taught himself how to heal and that work became his first book, One Drop of Water. Today he is a 3x author, runs men’s mental health retreats and coaches people out of the darkest places he once lived in. In this episode of Careers Under Construction, Jason shares: Why he never joined a recovery program and built his own roadmap instead How drugs at 13 and life on the streets of Winnipeg at 15 shaped who he became The motorcycle crash that nearly killed him Losing his dad to cancer How writing One Drop of Water became part of his healing How his biggest failures became the reason people trust and work with him today The message he wrote to himself the morning after his suicide attempt How he's helped people in suicidal crisis make it to the next day What happens when men finally open up “It takes a very strong man to embrace your feelings and your emotions, and to go against the grain of society.”

When Todd Burns took over his dad’s company in 2011, it was a one-man operation running out of a basement. Today, Cypher Environmental sells green infrastructure products in more than 50 countries and Todd is on a mission to replace toxic road salts with better alternatives. In this episode of Careers Under Construction, Todd shares: Why he refused to compete on price and focused on building better products How he spent seven or eight years grinding before his breakthrough around 2019 Why he stopped chasing the public sector and focused on mining and forestry The project that saved nearly $6 million and 934 million litres of water How a competitor who bragged about putting another company out of business indirectly helped Cypher gain market share in Chile Why Cypher donates up to 5% of project value back to local communities through its Green Roads program Because sometimes the breakthrough comes right before you're ready to fold.

Amanda Fiebelkorn didn't know what she wanted to do after high school, so she flew to Tahiti. After six months of nannying and teaching English, she came home with a new mindset and a new direction. Today, Amanda is the founder of The Social Manor, working with brands like Canon, Popeye's Supplements, Melted, Don's Photo and other local favourites. In this episode, Amanda shares: Why she didn't wait for years of experience before starting her own business How she hired her first employees out of her own marketing class How she landed her first client at $10 a post and what it took to raise her prices The Canon campaign that became her biggest break Why she uses Claude over ChatGPT What most businesses still get wrong about social media Watch the full episode to hear how Amanda turned a side hustle into a growing agency!

Three weeks after Nicole Dubé left CTV Morning Live, the role she had just left was eliminated. She didn't know it was coming. She just knew it was time. After 20 years in broadcast journalism, Nicole bet on herself and launched DUBÉ MEDIA, where she helps leaders communicate with clarity, whether it's on stage, on camera or in the conversations that matter most. In this episode, Nicole shares: • How “embarrassment resiliency” as a kid shaped her career • What it took to leave Hamilton and build a career in Winnipeg • Why she walked away from a job she loved • How she built a business despite having no sales background • Why communication skills will become even more valuable in an AI-driven world Sometimes the right time to leave isn't the time that makes the most sense on paper.

Rob Tetrault spent over a decade chasing one number: $1 billion in assets under management. When he finally hit it, he sat at his desk and felt nothing. No confetti. Just the realization that the goal he'd sacrificed so much for didn't change much. Today, Rob is the founder of Tetrault Wealth Advisory Group, overseeing more than $1.2 billion in assets with a team of 16. But the story he shares in this episode is about much more than business success. Rob shares: Why he walked away from a law career to start cold-calling 200 people a day The Ironman journey that helped him quit drinking and the four years of sobriety since Why he was one of the first in wealth management to embrace YouTube, webinars and digital marketing The story behind founding the Run With Rob movement How one diagnosis revealed a hidden problem: hardly anyone knew about CMV, the most common congenital infection and the leading non-genetic cause of hearing loss in children Why he ran across Manitoba, New Brunswick and PEI to raise hundreds of thousands of dollars for charity Because sometimes the goals that seem the biggest end up meaning the least and purpose is found where you least expect it.

It started with a beer ad during a Jets game. Taiv co-founder & CEO Noah Palansky was at a bar when he noticed the TV was advertising a competitor’s cheaper pint. He realized restaurants had zero control over the screens on their own walls — and built a solution to fix it. A few years later, Taiv is in over 5,000 locations across North America, with around 100 employees and more than $20 million USD raised. Noah made the call to build it all from Winnipeg — turning down repeated pressure to move to Silicon Valley. In this episode of Careers Under Construction, Noah shares: The bar idea that turned into a North America-wide business Why he moved to Miami for nine months to land his first customers What it really took to get into Y Combinator and raise $20 million+ Why he stayed in Winnipeg when everyone told him to leave His goal to build Winnipeg’s first billion-dollar tech company

Sandy Shindleman started with nothing and built one of Manitoba's largest privately-held real estate companies. Today, Shindico Realty manages close to 200 properties and $3 billion in assets across Canada and the United States. In this episode of Careers Under Construction, Sandy shares: The roles he played in the early days vs now Why he looks at how much he can lose, not how much he can make The 2019 stroke that forced him to rebuild the entire company How a dentist became his very first business partner The rule most entrepreneurs ignore 🎙️ Watch the full episode on YouTube, Spotify & Apple Podcasts.

Most people don't bet their career on a city.Jim Ludlow did.As President of True North Real Estate Development, Jim has helped shape downtown Winnipeg — the MTS Centre, the return of the NHL, True North Square, and now the $1 billion redevelopment of Portage Place and the Bay.In this episode of Careers Under Construction, Jim shares: What it really meant to be "the first hire" at True North The Phoenix deal that almost happened and why Atlanta turned into the Jets How True North ended up taking on Portage Place when no one else would Why he believes Winnipeg is undersold and underestimated What it really takes to rebuild a downtown It's about playing the long game — one inch at a time.🎙️ Watch the full episode on YouTube, Spotify & Apple Podcasts.

Élise Page and Teri-Lynn Friesen met teaching at a local dance studio. One random conversation changed everything. Now they run Fête Ice Cream & Coffee, one of Winnipeg's most loved scratch-made ice cream shops.In this episode of Careers Under Construction, Élise and Teri-Lynn share: What Covid did to their numbers and their biggest lessons learned Getting into retail stores like VitaHealth The hardest parts of being young mothers and business owners How they complement each other as a duo They thought everybody made their own ice cream. Turns out, almost nobody makes their own base. But these two business owners with zero culinary experience are doing it right here in Winnipeg.

He started a landscaping company in his early 20s. One year later, he was diagnosed with stage three melanoma. Matt Bell is the founder of Gellers — a luxury design-build landscaping company in Winnipeg — and co-owner of Shelmerdine Garden Centre. In this episode, Matt opens up about: Going from mowing lawns to running a 200-person company Being diagnosed with cancer at 25 Beating stage four melanoma and having a son, doctors said would never exist Why he acquired Shelmerdine Garden Centre His people-first culture and why a 97% staff retention rate is no accident How clinical trials literally saved his life and why giving back is non-negotiable What started as $15 lawn cuts is now a 200-person operation. But the business story isn't the only story here. Matt shouldn't be alive. His son shouldn't exist. And somehow, through all of it, he built a company where his people come first, every single time.